how was your first time getting fucked by a guy?

[Ewerton]

So...how old were you? How did it feel like? Did it happen before or after you started having sex with women and if it happened before, did it affect your attraction to women? I wanna do it..just not sure if I should before I start messing around with girls( which might as well happen in a few days, I'm trying to get one). I know a guy, pretty nice one who will top me...I just gotta let it happen...so any thoughts on it will be appreciated...thanks!!!

[sexual26]

My first time with a guy I was about 15 with a much older guy. He was amazing it started off with a little oral arousle for both of us then we moved on though he was a very gentle man and took it nice and slow it hurt a little bit at first (course I hadn't been loosening myself up before hand either) but anyway after he put it in he gave me a few minutes to relax and it still hurt just a little as he started to stroke but after the first few minutes it was amazing lasted for about a half hour was a great experience. This was long before I had any kind of a relationship with a woman now I'm married to my loving bi wife who knows I'm bi and we have three kids together. She also allows me to that special have fun when I
need to.

[Realist]

I was 14, he was 12, but knew more than I did.

He was my 3rd male encounter, but the first time I felt I was in love. I've never cared much for anal sex, particularly being on the receiving end of it. One attempt before him was a no-go!

I only allowed the 3rd guy to enter me because I loved him and wanted to please him. We mostly shared oral sex and masturbation. He had a very small cock and knew how and what to do; there was no pain and I did enjoy sharing his pleasure. He craved being taken and I enjoyed that, though.

Years later, I had another male lover in college, who I was very into. He's only the 2nd guy I received anal from. He had a very thin, but longer, cock.

In my 20s, I lived with a married couple, who both loved being entered anally, but I insured they knew I was not interested, myself.

[foreverbi]

My first time anal hurt like hell at first. I was sobbing for him to stop, but he just quit pushing & let me get used to his size. After a few minutes he started to move further into me & gawd did it ever turn from pain to the greatest feeling I had ever felt. After that first time I craved having a dick up my ass as often as I could get it, but I did learn a valuable lesson LUBE & plenty of it.:male:;):2cents:

[fredtyg]

I believe I was 21 but can't remember all the details as we were both drunk. I do know that it didn't hurt at all. I never had a problem taking a cock back then.

I had a friend that had just moved in with me. A day or so earlier I seduced him into oral sex. Then we went for anal. As best I remember, we started mutual oral again, then I had us stop for a second. I went into the bathroom and got some vasoline. I came back, put some of it on his cock, lay on my back and told him to stick his cock in me, which he did.

That's about all I remember. I don't recall him reaching orgasm or anything. I ended up having him fuck me at least every other night for the three or four months we lived together. Sadly, as with the first time, we were usually so drunk it's hard to remember the small details.

[ErosUrge]

Though I'd had lots of oral sex and mutual masturbation throughout my teen years, I never was brave enough to let anyone top me; nor was I interested in topping them. I was also enjoying girls too at the same time that I was with guys. Having fun with guys never affected my interest or desire to be with girls.

But my first experience with anal was absolutely horrible. I was with 2 guys who were much older than me; one in his 40's and the other in his 30's. I was only 19 at the time. They both were really attracted to me and their attraction made me want to please them all the more. So after oral play which didn't last long, they both wanted to fuck me. And I thought I might as well but was somewhat reluctant remembering how much I hated supositories when I was a kid. But prior to this situation, I had been curious about what it might feel like often playing with my ass by rubbing it with my fingers from time to time on the outside without ever putting a finger up me. So when they entered me they used KY jelly. This did not make it any easier for me because they were both very thick. I felt nothing but pain and no pleasure. But I wanted to please them and so endured it. Then a few months after this, I met another 40 year old man who invited me out to dinner and to spend the night at his home. At first I told him no, but finally decided, "why not?" We had dinner, went to his home, got into bath robes and drank wine. And then we headed to his bedroom. This man had the greatest patience and got me very turned on. Eventually he made it clear that he wanted to fuck me. Because of his patience and getting me so turned on, I agreed. But I was so afraid because of my previous experiences with the other two men before. As he entered me, I felt discomfort. But he was patient and told me to relax and that he wouldn't move again until I was okay...and that's how it went, little by little until he was completely in me. He waited still without moving. I was sitting on top of him so he would jack me off. When I was completely erect and turned on even more, he started to move. I felt absolutely no discomfort at all....I started to move with his thrusts and it felt so right and so good. Things didn't last long and we both came at exactly the same moment. After it was over, I couldn't believe that it had felt so good.

None of this ever affected my interests or desire for women. I was in fact more interested in women, but I always loved and still love sex with men.

[bi4asplay]

My first time was when I was 21.It was on my late wife's birthday. The only thing that she wanted was for me to promise to do everything she asked of me. I couple of years earlier she had fund out that I liked anal stimulation , by sticking a finger in me while giving me head. She then made her own dildo, as you could not buy them back then. The whole thing would take a couple of pages to put down here. This was also the first time that I ever touched another mans cock. I have never even thought about it. When the first guy( there were 3 other coup[les) pressed his cock against my ass I tensed up really tight, it hurt badly. She talked me into relaxing. He took his time and entered me very slowly. One of the other guys was face fucking me, my first taste of cock. When he hit my P spot the first time My cum almost hit the ceiling. Over the three day Memorial Day weekend that included a sail to Catalina Island from LA I got fucked 15 or more times and swallowed that many loads. I have loved it ever since. I still only play when a lady is in the mix. Though like right now I do love to ride a toy. Would love to find a couple or a lady into this kind of play.

[chepe1944]

My first time getting fucked by a guy I was 65 years old and it was a truly wonderful experience. It felt absolutely fantastic as the guys cock slid in and out of my hot and horny hole. He was rather long and large and it hurt a little at first but I had fucked my hole with a big dildo I had bought online, but the real thing was trulu great. I have been getting fucked ever since then and enjoy it every time.

[hma87]

I enjoyed my first time. It was when I was in college, 22 yo, with a grad student. We had fooled around a few times before, but didn't go beyond oral. So this time we had anal, and I was the bottom. He was patient with me and went in slowly. I had a little bit of pain at first but then relaxed and enjoyed it. I ended up cumming while he was fucking me in the missionary position.

[amorous945]

My first time being on the receiving end of anal sex took place when I was 13 or 14. It was very painful, but mainly because we were both drunk and had no idea what we were doing. The second time was much better and there was no pain. Long story short, me and my friend got together often after that and took turns fucking each other. I also ended up doing the same thing with another of my friends at the time, and also a couple of times with a friend who lived in another state. I had these experiences many years before ever having sex with a girl, but those experiences didn't diminish my desire for women at all. I've always loved anal sex, both giving and receiving, but haven't been on the receiving end of it for well over 30 years. I'm 54 now and have been married to the same woman for most of my adult life.

[bradford07]

First time was on business trip. Got talking to another guy at the hotel bar, went to leave to go for a swim in the pool, he joined me. Afterwards he invited me up to his room for a drink. Went to his room got out of the wet suit wrapped towel around myself, he came out of the bathroom totally naked, he asked if I minded, he was nicely hung. He told me if I wanted I could drop my towel, which I did, I immediately got a hard on, we played around, then got into 69. He started licking my hole, horned me out, then he fingered me, then he asked if he could fuck me, I told him I never had been fucked. He went slow and let me get adjusted to his cock and he kept pushing till he was fully inside. He rode me good. We did for the next two nights of my trip.

[oldercal]

Gosh, a nicely told story, thank you, it makes me wonder about doing it. I once was asked by a friend to kneel over him in bed, which I did to stroke our cocks together. But then I instinctively rose up a bit and felt his cock fall down below me, and when I went down a bit I discovered his cock along my crack--so I pressed down and then rubbed my crack along his cock, what a pleasure that gave--I ejaculated on his chest big time.




Though I'd had lots of oral sex and mutual masturbation throughout my teen years, I never was brave enough to let anyone top me; nor was I interested in topping them. I was also enjoying girls too at the same time that I was with guys. Having fun with guys never affected my interest or desire to be with girls.

But my first experience with anal was absolutely horrible. I was with 2 guys who were much older than me; one in his 40's and the other in his 30's. I was only 19 at the time. They both were really attracted to me and their attraction made me want to please them all the more. So after oral play which didn't last long, they both wanted to fuck me. And I thought I might as well but was somewhat reluctant remembering how much I hated supositories when I was a kid. But prior to this situation, I had been curious about what it might feel like often playing with my ass by rubbing it with my fingers from time to time on the outside without ever putting a finger up me. So when they entered me they used KY jelly. This did not make it any easier for me because they were both very thick. I felt nothing but pain and no pleasure. But I wanted to please them and so endured it. Then a few months after this, I met another 40 year old man who invited me out to dinner and to spend the night at his home. At first I told him no, but finally decided, "why not?" We had dinner, went to his home, got into bath robes and drank wine. And then we headed to his bedroom. This man had the greatest patience and got me very turned on. Eventually he made it clear that he wanted to fuck me. Because of his patience and getting me so turned on, I agreed. But I was so afraid because of my previous experiences with the other two men before. As he entered me, I felt discomfort. But he was patient and told me to relax and that he wouldn't move again until I was okay...and that's how it went, little by little until he was completely in me. He waited still without moving. I was sitting on top of him so he would jack me off. When I was completely erect and turned on even more, he started to move. I felt absolutely no discomfort at all....I started to move with his thrusts and it felt so right and so good. Things didn't last long and we both came at exactly the same moment. After it was over, I couldn't believe that it had felt so good.

None of this ever affected my interests or desire for women. I was in fact more interested in women, but I always loved and still love sex with men.

[olmizzou42]

My teenage suck buddy tried several times to fuck me, but we were just inexperienced kids with no lube and it didn't work. Lost my hetero virginity at 21 to an older woman. Married at 24 and had monogamous hetero sex for several years, producing two sons. At 30, I had sex with another guy whose cum was the first I ever swallowed. He wanted to fuck me, but a job transfer took me away before that happened. Over the years, I experimented with fingers and dildos and found that I liked the feel of having my ass filled and that nothing beats the feeling of cumming while being penetrated. I had several hetero affairs between ages 30 and 58 when I met Dick. At first, Dick professed to not be interested in anal sex. But, the third time we got together he moved from sucking my cock to licking my balls and then getting my legs up he went down on my asshole as if it were a pussy. Oh, how I loved the feeling of his tongue licking and probing followed by his fingers. He had lube and a condom handy and was soon fucking me. Fantastic! No pain, just pressure as the head of his cock passed my sphincter then the wonderful feeling of being fucked...hard. Over the years he has fucked me numerous times and I have been fucked by one other guy. I have fucked Dick once and have also fucked two other guys. I can be a top, but so much prefer the bottom. Both men that I have received anal from have relatively small dicks so having a big cock plowing my ass is on my bucket list. My favorite fantasy is being in a 69 while being fucked. My 69 partner could be female because I love eating pussy too.

[Patrick43]

First (and only) was when I was maybe 15. He was older, and it really wasn't my idea at the time.
Yesterday I met a friend and we were playing around. Ended up trying to get penetrated. Wasn't gonna happen. Evidently I am quite tight. I might try again, someday.

[jwaage1986]

I was 28 and visiting my sister in the desert SW. I had a teenage gay friend and decided to act on my urges of more than 12 years. I went to an adult book store. Hooked up quick after he slipped a note under my door and enjoyed having a nice eight or nine inch cock in my mouth. He then gave me a wonderful blowjob. The next thing I know is that I am begging for him to take my cherry ass. He went and bought some lube. I put another condom on him (have to be safe) and sucked him hard again. I then got on a bench and positioned myself. He grabbed my hips and was not gentle, thrusting it in to the hilt in one thrust. It hurt so bad I had to pull away from him. I then asked him to take it slow with my virgin ass. Martin, wow was he good, slow entered my ass and took his time. His hands were on my hips and I felt very feminine and gay; a cock in a man's ass should make you feel gay and I am a cross dresser. Martin then fucked me long and hard for about twenty minutes and I learned to push back and meet his powerful thrusts. It was a wonderful experience. If it was not for disease, I would let others fuck me more often. This was my first of only two bottom encounters in my life.

[ooooooo]

my first time was in a gay bar in the bathroom IT WAS SO BIG WAY BIGGER THEN MINE I MEAN WAY BIGGER I think it was the first time i fell in love with a man it hurt at first but then I didnt want him to stop.I noticed people were kinda trying to look in the stall and god help me i didnt care I wanted them to come in. My main fantasy is now being fucked and a dick in my mouth OMGGGGGGGGG.The last time was two weeks ago in a adult book store it was so hot. I did have fun there was a hole but i was with someone in a room was hoping a cock would appear from the whole but it didnt happen.Sometimes I feel kinda like a girl when i do this does anyone else feel this way

[Wanabee]

I was 15 and he was 40 something. It wasn't the nices experience but i remember it damn well. Back in the 70s and early 80s we have very little knowledge about anal sex. I was a girly boy and wanted to be a girl myself, i wasn't interested in girls back then. It wasn't until i was about 24 when i had my 1st sex with a female and things started to changed for me.

[Jimlikesitnow1]

The first time was today. My wife died six years ago and I never wanted to be close to any one again. I dated women a little but they were so demanding. I did not feel manly to them. I started going on porn sites. One night I ended up on a gay porn site. I was mis-directed by my search engine. I look at gay porn all night. I was married for 28 years before my wife died. I have never before today been with a man. I am white and had always heard that a black man's cock was huge. I never believed it. I advertised on a bi-male dating site. Today a really nice 40 year old man responded to my ad. He came to my house this morning. This is all true I swear.
He was a muscular black male. I am but an average middle aged while male. I live alone. He was so kind. He took off his clothes and I did the same. I panicked when I saw his cock. It was over 10 inches long and thick. I told him no way. I was a virgin. He was not all the way hard. He gently pull me to my bed. He held me. I know he was there for my ass and would not take no. He held me in bed as said we didn't have to do any thing. Then he ask me if I wanted to just hold his penis. He could tell I was fixated on it. My eyes never left this beautiful sight. Before I knew it I was kissing the thing I feared the most. After I began to suck it in earnest, without gagging it was down my throat. He fucked my face until he came down my throat. He filled my stomach with his hot juicy cum. After I took my mouth off his penis I thought I was safe. Surely it would go soft and he would be satisfied. I was wrong it was as big as it was when he started. He turned me on my side, lubed up my ass and his cock and entered me about two inches. I hurt like hell, he held me from behind and backed out. I told him I could not do it. By now I felt like he owned me. He tried again about maybe four inches in I hurt really bad. He backed out and said relax. His was so smoothing. On his third try he pushed in about five inches it hurt but not as bad. Then in an instant he drove that ten inch, thick cock all the way in. I thought he was going to kill me , then the pain just stopped. He felt me relax then he fuck me like a wild man, About 20 minutes into it I felt him come, he filled my rectum. He pulled it out with a pop and said he was coming to fuck me again. I said "Please do". His cock slid right back in. No pain. He fucked me for an hour. I lost count of the number of times he came, but I think he filled my colon. When he stopped and pulled out it was still hard. We took a shower together and told me he would be back Sunday morning. He said he wanted to fuck me all day and spend the night. This was his first time with a man. His ex wife ( a white lady) did not like his ten inch dick. And she would not let him fuck her in the ass. He told me he always want to fuck all night long so he is going to stay with me all day Sunday and Sunday night and most of the day Monday. He says his cock was going to be in my ass all night. And He and I will not sleep at all. Pray for me. I really like it.

[Swirl]

First time was in my early 20's after a few females. Was with a long time gay friend in a book store. We had never done anything, but were both horny that night and hit the hourly motel. Sadly, it was as unsatisfying as I can imagine. He was very small, which wouldn't have been so bad except he came in 3 strokes. Broke my anal cherry though. There were a few other early encounters with different guys that were clumsy affairs where I just didn't know what I was doing.

And no, this has never had any effect on my desire for women at all.

[sabbath101]

i've been humped and had oral sex with a lot of guys but still have a virgin ass. reading the stories here got me really interested as well. any ideas to how to make it easy for first timers?

[wm1809]

It was quite interesting it happened in the office of a auto parts store after hours during a conference call.It lead to many more great times with him

[Wombatso]

I think it is best that I don't say how old I was but my time experimenting with my first lover was started with my initiative. He was a few years older than me and one day he laid me on his bed and took full control instead of just swapping turns in sucking cock. After he tended to my body with kisses and licking and massaging and such, he entered my anus and fucked me in a few different positions. I loved it. It hurt at first but the pain quickly became pleasurable and I was his for the fucking. We were both laying on our sides with my back to him when he came inside me. We laid there together for a while afterwards while wrapped in his arms. It was amazing and I was eager for more.

[sailorashore]

It was 1977. I was 31 years old, my partner was 25, a young bartender I had known only a short while. I had allowed him and a very drunk female customer of his to crash at my place, across the street from the bar, as she was too drunk to drive home, ans she was his ride. She ended up in my bed, and we shared a not-very-memorable fuck, while he slept on the couch. Somewhere in the middle of it, I realized that, after years of a strictly heterosexual life, I was wishing it were he lying next to me instead of her. He was a very attractive young man, and gave off some unmistakably gay vibes. The next day, after she had gone home and he was back at work doing a day shift, I went over to the bar in the early afternoon. When there were no other customers around, I somehow found the courage to tell him about my thought the night before. My heart was pounding, I was so nervous--he just smiled, and asked me if I'd like him to come over after work. I don't know if I even spoke--I think I just nodded my head. When he got there we talked for a little, and I was so frightened I was shaking. He seemed to understand, and took over. He led me into my own bedroom, gently undressed me, stripped down himself, and lay back on my bed. I was mesmerized, and couldn't take my eyes off his beautiful naked body, and his fully erect cock. I lay next to him, and began to explore him with my hands--the first time I had touched another male since I was fourteen. I found that I was full of pent-up lust, and couldn't get enough of him, his smell, his feel, his taste. At some point I climbed up over him, took some lube from the nightstand, and lubed up my anus and his gorgeous throbbing dick. I straddled him, and gingerly settled myself onto his cock, a little at a time. Yes, at first it hurt like hell, and I had to back off a bit. After a little while, though, I began to relax a little, and soon I had him all the way up inside me. I just sat there on him for a spell, marveling at the thought that I had another man's dick in my ass, and I could feel him getting harder as he began to squirm a little and thrust upward. He asked if we could change places, and I agreed, sliding off of him. I took the opportunity to put some more lube on both of us, and when he lifted my ankles into the air and pressed the head of his cock against my rosebud, I gasped--but he slipped in easily, all the way to the hilt. "Holy crap" I thought, "that feels INCREDIBLE!" When he started to move, I thought I'd died and gone to heaven. The feelings of submission, of intense desire, and of sharing this "forbidden" experience with another male were, to say the least, overpowering.
It was ultimately frustrating though. All the while that I had been relaxing my sphincter enough to accommodate him, he had been getting more and more aroused, and closer to orgasm--he was in his twenties, remember. Just as he started to get into a powerful rhythm, plunging deep into me, and I was transported to a whole new plane of erotic experience, he stopped. I begged, "No, don't stop, PLEASE, I want you to cum in me." And he breathlessly said, "I did." I had not noticed any difference in the way he was stroking me, nor had he made any telltale sound--grunt, gasp, or whatever, right up to the moment he had stopped. I felt cheated somehow. Clearly, I had been very focused on HIS orgasm. Mine had occurred early on, he had sucked me off when we first stated to play. We did not use any condoms--this was 1977, and we hadn't yet heard of HIV.

It was so long ago, but the most intense sexual experience I had ever had, and I remember it very vividly. One thing I learned from it. To this day, if I am getting close to cumming, my partner will always know it! I make noise, and communicate what is happening. Sadly, man-to-man sex didn't happen again in my life for many years thereafter. But that's a story for another time.

[curious44]

I honestly don't remember my first time or who it was with. I do have fond memories of many encounters and one long term partner in particular. He had the perfect cock and could make me melt with his rhythmic strokes. I'd bend over my desk after hours and welcome him in. WOW!

[Cherokee_Mountaincat]

WHEW! Note to self. "I gotta quit readin this stuff from you guys. Now I need a damn cold shower!* lol
Cat, grinning.

[SweetnSpicy241]

Ditto :bowdown:

[easilyused]

my first time was in a gay bar in the bathroom IT WAS SO BIG WAY BIGGER THEN MINE I MEAN WAY BIGGER I think it was the first time i fell in love with a man it hurt at first but then I didnt want him to stop.I noticed people were kinda trying to look in the stall and god help me i didnt care I wanted them to come in. My main fantasy is now being fucked and a dick in my mouth OMGGGGGGGGG.The last time was two weeks ago in a adult book store it was so hot. I did have fun there was a hole but i was with someone in a room was hoping a cock would appear from the whole but it didnt happen.Sometimes I feel kinda like a girl when i do this does anyone else feel this way
where did this happen? I live in Illinois and want it to happen to me !

[Indywood]

Ever been to a party after the party? I was getting blown by the girl I was with and looking around seeing sex everywhere- but these were guys (and girls) having sex with each other! shortly thereafter her fingers are moving in and out of my ass while she's sucking me and I'm starting into sucking my first cock, which was the largest in the room! Not sure if it was the alcohol, the drugs, or the atmosphere but I fell into a state of "I dont care what happens, this feels so good!" I simply couldn't help myself, I fucking wanted it! I wound up getting it from 7 different guys (including the first guy I was sucking- my god he was big!), and a few different girls- not sure how many times I got fucked that night- still the hottest sexual memory I have. I had been quite sexually active for some time, and while I did wind up having sex with a lot of guys following that night (all of the guys that fucked me that night wanted more, and they all had friends) it never diminished my desire for women- although it did give me a strong desire for groups (male/female together-heaven!)

[Jimlikesitnow1]

Sorry I have not been on since Wednesday. I was wrong about my new friend coming back Sunday morning. He came back to my house Saturday morning and he just left. He came in to my house Saturday at 11:00am. He was ready for more. He took me to my bedroom, dropped his clothes and I was shock that his cock was so hard. He told me he could not wait for 24 hours to get at me. I carried me to my bed and gently laid me down. He got on top of me and feed me his cock in my mouth. I stopped gagging and just loved the feel of it going down my throat. He was so careful to give me air. I lost count of the number of times he came, but the cum was backing up my throat.
He pulled out, then he lubed my ass with cum erupting from his cock. I became afraid that I could not handle his thick cock in my ass, but he worked the cum in my ass with his large fingers. I must have relaxed at that point, cause he slipped three of his fingers in with ease.
At this point I began to moan uncontrollably . He turned me on my stomach and got on top of me. With my ass in the air he slid his cock into my ass. He went deep, far deeper than on Wednesday. He came again then he went to work . He fucked me like a wild man. I came like I never had in my life. He fucked me for about three
hours straight. He kissed me on my neck, then I went to sleep. I was exhausted.
He must have continued to fuck me in my sleep. I have never seen so much cum in my life.
I woke up about seven in the afternoon and he was sitting on the bed smiling at me. We talked for about an hour and I confessed at this point he owned me. He had some chilled wine in a glass and I drank a whole glass. This man is enormous in size, so muscular. He had ran a warm bath for me and he picked me up an took me to my tub. I was so weak. He bathed me, he lifted me out of the tub then dried me off.
Then he laid back on my bed, he had put clean sheets on the bed, I was in heaven. He brought me a lite dinner which he fixed while I was sleeping. We drank more wine.. At around nine last night we went back at it. The thing I don't understand is that my ass was not sore. He was so considerate. I don't know what time I went to sleep, but the last thing I remember is that he laid me on my side and fucked me all night. To be the first man to ever do this to me, it felt so natural. At nine this morning he woke me with breakfast in bed, He had coffee and bacon and eggs. He was fully dressed and told me to stay in bed and that he had to go home.
Then he did the most amazing thing. He told me that I had the finest ass he had ever had. He also said he would never go back to fucking a woman and that he would be back at my house, this Friday night. As he left I told him that I truly loved him. He replied, "James, I know."
All this is insane to read, but it is absolutely true.

[friesbaconnekkid]

Hi everyone, new guy here.
My first experience was when I was around 50 years old. Some friends were coming over, as the guys wife wanted to have a double penetration. As luck would have it, she had started her period that day, so that kind of put some barriers in the way.
I was horny as could be, and came right out and asked Tim if he would like to fuck me?
He was all for it, as he and his wife had anal sex a lot, and was not only experienced, but as horny as I was.
I took off my clothes, as did he. Arlene fondled my cock, getting it rock hard. Tim got on his knees, and took me in his mouth. After a few minutes, we swithed position, andI had a cock in my mouth for the first time. It was more rubbery than I expected!
After I had sucked on him for awhile, I got in doggy position, and he lubed my ass. He then gently started his cock inside of me, until the full length was imbedded. He then started slowly stroking in and out, as Arlene took pictures of us.
The sensation was fantastic, making me a fan of cocks in my ass ever since! A most enjoyable experience!

[bi4asplay]

I was 22. It was my late wife's 23 BD. Had never thought about sex with another. We had a 4 day weekend. She had invited 3 other couple to spend the weekend a sail to Catalina Island with us. She had been using a home made toy on me for some time. For her present she wanted me to suck and be fucked by all of them. Over the 4 days it happened many, many, many times. I loved it. We played with the same 3 couples for around ten years after that. She loved to be on her back under me and guide him into me and we would 69 while he fucked me. She would always cum just watching a dick pump me.

[The Jackal]

where did this happen? I live in Illinois and want it to happen to me !

No kidding me too.. I either need a shower, or need to rub one out.. maybe both at the same time.. my first time here, and now I really want this more than ever..

[Lynn731]

It was on a sleepover with my best friend. We were gonna jack off and he said lets stick it in each other ass. It hurt at first, he has 7". As he left it still for a while it began to feel good. He cummed a lot in me, I loved that. Then I fucked him slowly, I have 6". We love it, have been doing it ever since. We are both married, he has 2 grown kids. I have none.

[NjbiGuy01]

I agree with Cherokee....I'm sitting at work half-hard, horny....now I gotta try to hook up before I go home...lol.

My first time was as a teen. I'd played with a buddy and we progressed from mutual jerking off, to jerking one another off, to sucking one another, to eventually anal. We started with fingers, then toys, and advanced to him rimming me and getting me ready. For me, it takes time to get relaxed, releasing my inhibitions, and getting loose enough for penetration. The key was pushing outward to allow him to enter me (almost like you want to take a shit)....Patience and size make a big different too. My friend took his time and little by little he got deeper and deeper. The feeling went from heat and some pain, to total pleasure. My cock dripped seminal fluid as he pumped me. I was actually shocked to realize he was "balls deep in".... his balls started slapping mine and the feeling was amazing.

[guywholikesboth]

Ilost my cherry last week to a 19 year old with a small cock about 4.5 inches but he had low hanginh big balls. I loved it hurt at first but then it changed to pleasure. Now I know why my wife liked it in the ass. only wish I had done it sooner. Cant wait for the next time.

[dickhand]

First time was awkward to say the least . My cousin and I were around 12 or 13 . The second time we swiped a little margerine to ease the experience . Much smoother going after that little discovery . We did it well into our late 20s . Both married with children by then . Drifted apart after that though . :(

[BiBIKER065]

My 1st and only time was about a month ago (65 yrs. old). He didn't use enough lube and came to quick. It felt like he was ripping me open and was not a good feeling at all. I would like to try it again, but with someone that was a little more considerate.

[sunshinmeet]

My first time was 3 years ago. I laid on my back atop his desk(Office scene=hot). His dick was small, so it went in real easy, especially with the lube. Didn't feel any pain.

[striker48192]

Mine was about 4 years ago we were both dressed in drag at his house and of course one thing led to another and we were naked sucking each others cock and he ask me if i had ever been fucked and of course i had not so i said i was all for it . He fucked my ass but good took his time , it was the most wonderful sexual experience i have ever had looking forward to doing it again .

[tommyswing]

It tool me a long time to open up, didn't know how to relax. The first time I enjoyed was in a movie theater, I was wearing fuck me shorts. This guy came behind me licking my neck and rubbing his cock over my ass. He took me into the bathroom, put on a lubed condom and fucked me over the bathroom sink. I loved being taken like that so submissive. If there where any tops in south florida I would do it more often

[Ebonybifemme7]

As a bi female who has never done tha anal thing...WOW.

[BootyBuffet]

Loved it! 18 years old, with my best friend. Felt fabulous, and I especially loved the feeling of him holding my hips from behind and plunging his cock into me and spurting cum (pre-HIV). It was super hot, and made me the bottom that I am today, LOL! Luckily, my super-hot wife also loves to see me get taken by a big cock, and then fuck her. I am a very lucky guy!

[krisrryan]

Haven got the opertuniny to be fucked by a guy , but the feeling of getting a blow job while being fingered is awsome ! Anyone want some of this tight ass ?

[kinkytats]

My first time was a little weird. I've sucked cock before but that was it. Then "it" happened. Having used toys before, it wasn't painful at all until he got close to cummimg. Good Lord he damn near broke my hips. Ouch! Lol! I prefer nice and slow and long.

[Expat692]

I was 13 and he was 15, we had known each other for anumber of years and often had sleepovers at each others houses. He asked me if I would like to sleep in his bed with him rather than on the camp bed, I thought it would be nice as the camp bed was rather uncomfortable. Once in bed together he started to touch me and asked me to touch him, i was enjoying it so did not mind playing with his penis as he played with mine. After a few minutes he asked me to turn away from him and take off my pants, i could feel him pushing his penis into me and although it hurt at first i thought he must have done it before so it would be ok. I began to enjoy the feeling of him being inside me but it only lasted a few minutes before he pushed as hard as he could, held me really close and came. We continued to sleep together on our sleepovers for the next year or so until he and his family moved away. This was my first sexual experience and still one of my best sexual memories, I have no doubt that it moulded my sexuality and made me who I am today.

[amorous945]

Like many others, my first experience was painful, but only because we had no idea what we were doing. The second time was much better, and only got better with each experience.

[donlikesdicks]

After looking at the above stories I feel sorry for so many guys who had a bad experience. Mine was great, and I was 60 when it happened. The doer was a handsome Negro cop from Dallas, attending a foursome party arranged by my girlfriend. My response was, "Good God, I've been missing this for forty-eight years! What is wrong with me!" I began looking for other men to fuck me. The same guy filled my mouth with cum during that wonderful night, and so I have been a cock-hound ever since. The last time I even wanted to fuck a woman was ten years ago, and when we were saying goodbye the following morning, with her sitting in front of me naked on the bed and me patting her very wonderful pussy, I thought, "God, I wish she had a dick!"

[donttellnehismy]

my first was nice but awkward... Was when I was young and it was with my best friend... Happened on my parents bathroom floor after looking at Penthouse

[man4girlgirl4man]

I was 46. After my divorce. Got tired of only toys so went to a gay bar and picked up a really hot younger black dude - around 30 or so.

His dick was between 9 and 9.5 inches and thick. And I told him in advance he would be the first real man to ever fuck me with his real dick.

Answer to the question is this: It was great and sexually intense. When we were done he said he coudn't believe an ass virgin could take a dick as big as his (I did but slowly and softly for the first half of the fuck, and he never slammed me fast or hard because I told him not to beforehand).

Not only just took it either. I fucked him back as hard as he fucked me. I was in motion the whole time. And I was telling him to put his dick in me "more more more" the entire time - subconsciously mosty.

[Enlightned]

Last month was my first time. In fact,it was only my second time being with him. We had been sucking each others cocks on the first date and were doing the same thing this time. He started fingering my bottom while sucking my cock and I started squirming and trying to ride his two fingers inside of me. He is experienced and im not so I let him lead. he rolled me over and pulled my hips up to him so he could enter my bottom. I heard him say Oh crap ive gone limp. I told him just relax. I guess we both wanted it too badly and were too tense. I proceeded to suck his cock again ( I have discovered I am good at it and love doing it!) And started fingering his rear. He got hard as a steel rod so I just up and straddled him before any thing else could cause his hard on to go away. His cock just kind of popped in! It hurt at first but I slowly started to ride him and the pain went away. Oh my God he felt good inside of me! I think I must have rode him for about ten minutes and he started to stroke my cock. Holy moly I came like I had never done before and I guess my anal contractions caused him to cum because I could feel his cock pulsing in me and come hitting the walls of my anus. I am hooked now and hope he will let me do him also.

[nudist_60187]

my first time was probably 30 years ago or more, it happened at a bath club I think he was a little bit older than me at the time I really don't remember I do remember how we actually took time to make love to me not to have sex. there was not an inch of my body that he did did not touch lick and enjoy. when he entered me it seems so natural so good and it was very back as a matter of fact. I remember hearing someone asking him how was it and he said I was fantastic. I'll never forget that experience. The only other time was years later and that person did not take the time that he did and was not as enjoyable I hope to find somebody who will take your time again to take me because I am actually open to it thank you for sharing all your stories guys

[Cuiriousmark]

I was seduced by a porn store owner during college. It started with a bj and after awhile we ended up in his office where he took me on his desk... hurt like crazy at first, bunt after a few minutes it felt great and about 20 mins later I came from it - a very intense experience....

Cheers

[miaflyer2006]

My 1st time was when I was 50 yrs old--i guess u can say it was a mid year crisis thing. I am happily married but wanted to see how it would be with a guy a fantasy I've always had for many yrs. Anyway I found this guy on the internet and we met for a coffee and went back to his place--he was gay and had a partner who also jopind in so I was in heaven sucking and kissing and jerking and just having a great time! Soon after his partner left and I asked him if he would try anal on me--he asked if I was sure I wanted that and I said hell yea! Well he asked if I was clean there and I asked him to explain and he said did I have an enema or been cleaned out. I told him no so he set up an enema bag in the bathroom and I did my thing! Once I was clean and ready he lubed up a dildo and opened me up some--he was very gentle all the while--he then told me I was ready and wanted to know which way I wanted him! So not knowing to many positions for anal I said doggie style! So he got behind me and put his cock at my opening and slowly and gently entered me! God it hurt at 1st so he stopped and waited till I was ready--did I mention he was 8" and thick--he waited till I started to move back on him till he pushed forward--now it started to feel amazing!! He fucked me easy at first then when I urged him on he fucked my hard and steady till he filled my ass with his hot jiss! Its happened several timed dince and its always something different with them and I am so addicted I have told the wife and she understands and is very excited about it and wants to join in sometime soon.

[fused]

Good lord I hope I can experience this some day. I've done everything else with another guy, but no fucking...yet. :(

[Rod_7_5]

My first (and this far only) experience was when I was about 14 and it was comically bad. A friend from out of town was spending the night, and we stayed up late watching what Siskel & Ebert called "horny teenager" movies, then went out to the pool to skinny dip. When we went to bed, we started playing with ourselves, then each other. The next day continued our explorations. I went down on him, and he asked me if it felt good. I was a bit puzzled...did it feel good to him? Then we decided to try anal. I tried to enter him first, but either I was too big for him, he was too clenched, or a bit of both...never got in. We switched places and I *think* he got it in, but to this day, I'm not entirely sure. He was smaller than me, and it felt like something was in my ass, but if he was in, he didn't do anything...just sorta stood there. After a moment, he asked me if he was in. I answered, "Dude, I'm on my hands and knees with my ass in the air. You're the one who can look down and see if it's in. YOU tell ME."

The very end of our session really says it all: he didn't know you could cum from masturbation until he saw me blow my load; said he'd always stopped because it felt like he had to piss.

[rolled469]

I am very jealous! When we kids, 12 or 13, during out J/O sessions we slide our cocks up and down each others asses. Well on hot sweaty days the kid next door used to let the head of his slide in me, it felt amazing! But that's all the further it went. I am married, kinda straight, but i still want to see what it would feel like to go all the way in!

[NjbiGuy01]

My first experiences were with a bunch of my friends in my mid teens. We were macho jocks with girlfriends. We were just so horny that man play (jerking off anyway) was a great release. We watched porn, and jerked for hours !! One day the group was busy with other stuff and it was just me and my one friend Mike and we went further: We tried oral successfully and eventually we explored anal together. His parents were out from 8 am to 8 pm working, so we had the house (and their bed) to ourselves. We went from oral, to showering together, and eventually started fingering our asses and then sticking his moms vibrators and toys in our asses ! We evolved to "why not let me try fucking you ?", and we ended up doing that as well. A lot depends on size, shape and patience. I find long and thin better than thicker for sure. I played with a few couples and some experiences were really awesome and others not so much. Sometimes it just doesn't work. One dude kept losing his erection after he got into me. I think he wanted to please his wife, but maybe wasn't as bi as he wanted to be.....One guy (who's cock looked exactly like mine) tried fucking me a few times. I knew I could handle him (I'd handled sizes like it before), but I was so tense from the whole experience that I couldn't relax. I eventually fucked him a few times, and we discovered (one day while playing without his wife involved) that the best way for me is on my hands and knees. He tried previously with me on my back. She was sucking me and jerking him as I laid there and he tried to get in, but couldn't make it work....I could not relax my ass enough !! Once we found that secret we were golden !! Most recently, a local message therapist topped me a few times. He's a good 8", but the bone structure is thin and he knows how to take his time !! He put on a rubber glove first, lubed me slowly and gently, massaged my balls and prostate, slowly jerked my cock and eventually began rubbing his cock on my ass crack and then sliding his cock into me: He was a master ! He was as perfect as you would want a man to be. He totally took his time. First the head, then a retraction, and slightly more into me. He kept repeating this until he moaned and I reached under me to feel his balls touching mine !! I asked "you in all the way ?", he moaned "oh-yeah".... When we were both ready to come, he pulled out, I turned over, and together we glazed my belly with a big load of both our cum....There was a time I was spit-roasted by two guys on a cruise ship balcony, but that's for another time :yikes2:

[Cum1st]

In a word – messy. We met in an outdoor pickup spot. I was in my late twenties and married. All the other guys that I had picked up just wanted to 69, Which was fine with me. We almost always lay on out sides with our heads resting on the other’s leg. Cocks and balls that could be coaxed through glory holes were happy to be sucked. I’d thought about being fucked, but craved sucking cock much more even than even being sucked off. I liked (like) it so much that I didn’t (don’t) mind cumming first. (Hence the name Cum1st with men who might want to stop after they cum).

I always made sure I was clean of course, but didn’t give any thought about what might be IN my ass. He came at least twice in my mouth, and then asked to fuck me. I was up for it and don’t remember any pain. There was just a wonderful dizziness. After he came in my ass he was satisfied. I liked it! We cleaned up, and like the other hookups we never saw each other again. Sometime after that I bought a latex cock to accompany self-satisfaction. It really pumped out the pre-cum out of my stiffie. I’ve been reamed quite a few times by a steady hookup while it lasted. Each time he had sucked me off first, and didn’t last long enough to give me an anal orgasm, although I do remember having double vision and week knees as I supported myself on the back of a sofa.

Thinking about this is making me want to drag out my home made crank operated “sybian” and make some improvements so I’ll have to test it. It will run at 50 or 87 strokes per minute. The length of the stroke is adjustable. Turning the crank one way it pushes up on the in stroke, the head sweeps down, and withdraws. In the other direction it does just the opposite.

Oh yeah! I still can’t imagine why anyone wouldn’t jump at the chance to be with a woman.

[TerrorTwilight]

I was about 16, the guy was in his 50's. I had been sucking him off for a few months but nothing more, then he mentioned that he'd like to fuck me. So I ended up letting him try, got up on all 4's on his bed and he used a ton of lube, finally got it all the way in and pumped a few times but it was too big for me. Tried again a year or 2 later with a different guy but the same result. Haven't tried since.

[mudbogger69]

I have this buddy of mine I want to ask to fuck me but I'm to scared to ask we joke around bout doing it but I'm to scared to say I'm serious any suggestions

[bictguy14]

I'll add my first time story...it was about 5 years ago, I was 30 or so, knew I had a desire to be with a guy for years at that point...would finger myself, etc. Finally tried some websites, posted an ad on manhunt.com, and would chat and email guys but nothing came of it. Finally a guy that lived a mile from me, contacted me and we got to talking, it took weeks or so, before I worked up the nerve to want to take the plunge. Finally IMed each other one day, and within a few minutes I was at his house. He knew that this would be my first time, so I already told him, when I get there take charge. Take charge he did!! Within a minute of walking into his house, I was bent over getting rimmed. Holy Shit, what a great feeling. After a few minutes, we moved to his bed, and wow things just got better. I was on all fours in no time, he was still rimming me at that point until I felt him stop. I arched my head back to see that he was getting in position to finally enter me, at that point I couldnt contain myself, I was all sorts of excited but also anxious. I finally felt the head of his cock pressed agaisnt me until I felt him slowly work his way inside. What a feeling!! Thankfully he wasnt too big or too thick, and it didnt take much to get him all the way in. At that point he just went to town on my ass. Grabbing my hips and pumping until he felt himself getting close and stopping just long enough to grab a condom and finish fucking me, until he came. At that point I was in ectasy and I didnt ever come yet. Of course at that point he rolled me over to my back and gave me one of the best blowjobs I ever had. Since then we have gotten together a few more times. Now that I am married it is harder to get together with him or any other guy, but since that time I have gone from being bicurious to 100% bi sexual.

[bi4asplay]

Good lord I hope I can experience this some day. I've done everything else with another guy, but no fucking...yet. :(

I could help you with that.

[firstone]

Mine was about a year or so ago, I was with two other men and I asked one of them to fuck me. It wasn't real pleasant, I think he was trying to hard and it hurt so I asked him to stop. I would try it again, slower the next time.

[nipers]

I was 55, I had a place ,made a contack. I was so scared but also wanted to try it so much.he came over we talked then sucked , then he got me on my back and before I knew it he was in slowly fucking me. it was good but I really want to try with someone that will start slow then fuck me hard and fast

[txbiguy2791]

Crazy hawt drunk car sex with a total stranger

[HappyHedonic]

My first time was excellent. I was about 24 years old. He was well hung, but gentle and patient....he worked slowly and carefully so I didn't feel pain. He eased it in as I relaxed more and more. By the time he was all the way in I was begging him to pound me all the while I was stroking myself. I found out that orgasms while receiving anal are the most intense orgasms I can have.

It happened after I had already had sex with women and it did not change my attraction towards women at all. If you really liked chocolate ice cream and along comes a flavor that you had never tasted before, say amaretto, and you really liked that too, would you suddenly not like chocolate anymore? Of course not! Sometimes you might be in the mood for one or the other and if you are really lucky you get to mix them together and enjoy them at once.

[CowboyCowboy]

Hurt like hell. I was 16 and fucked my Mr Hector who was in his 40s. I did cum twice as he fucked me. The following times was much better. Had to get used to it.

[mtnmen2]

Painful, we first started with me laying down and him trying to put it in with nothing more than some spit but it hurt to much. He suggested that he set down on a chair and I lower myself down on him. It hurt as he first entered but as we went along it started to ease up and pretty soon I was rocking in time to him getting into it as he suddenly pushed me off of him and I watched him spew a huge geyser of cum from his cock. I was 14 at the time.

[boytoy1223]

I was 31 I think. I'd been using toys and my fingers way before that. The first time with a guy was a good friend and he was the right size. It actually felt really good cause I had warmed up and stretched with a toy. I have a gf now and she knows I like ass play but I haven't told her I'm bisexual. I really need a good fuck so I guess I'll tell her.

[gotlek]

I was 12 he was 13 first time i hsd sex and got fucked in my life, first time was little painful , my ass being small and tight, virgin. his was big and thick for his age, I just loved being fucked since then...
2880928810

[Fzmr9t]

My first and only time was when I lived in [place redacted]. It was about 10 years ago. I'd been going online and had met a few guys, but it had only been mutual oral at that point. Then I met [name redacted] during an online chat and we agreed to meet at a Wendy's close to my house. We chatted a bit, and were comfortable enough, or horny enough, with each other that he followed he to the house. There it was the same as with the others. Mutual oral (69). It was his first time w a guy, and about my 4th or 5th (or 8th or 9th, I'm not sure which). Anyway, found out that [name redacted] lived near where I worked, so we met at his house for a "nooner" a few times. Still just 69ing. Finally, [name redacted] came back over to my house and we made out (kissed, hugged, touched) and [name redacted] said "I could really use a shower", so we both got in, a first for both of us, and lathered each other up. After I rinsed him off, I went down on him in the shower, but didn't make him cum. Then he did likewise to me and I told him I'd rather continue on the bed, so we quickly troweled off and went to my bed.
we continued the kissing and fondling and sucking, and I asked him if he would try to fuck me. He pulled out a condom and I went for my ky, and I put the condom on him and we rubbed the jelly on each other. I assumed the position (head down, ass up) and he slowly started rubbing his cock around my anus. THAT WAS AWESOME! then he pushed in a bit and I felt IMMENSE pressure, to the point of pain. [name redacted] wasn't overly large (more like me, about 5" and thick), and I had played with "toys" in my ass before, but I guess I was nervous and tense. [name redacted] took his time and continued to slowly rub and prod! and I finally relaxed enough that I felt the head of his cock go in. OWWWW! He slowly pushed in deeper, and I kept relaxing and it finally eased up to the point that it was feeling WONDERFUL! after a few strokes, I felt him tense up and tighten the grip on my hips and heard a moan and a groan and he popped out of me. I rolled onto my back and took the condom off of his cock and proceeded to clean him up a bit. He was a bit tender, and was shrinking at that point so we got up and got dressed and he left. We met a few other times, but that was the only time that we fucked

[suckemall]

I was around 15 when I met an older man who took interest in me while working around him at school. He followed me to the rest room and asked me if I mind him watching. Now I had been sucking my brother's cock for a long time and playing with my older sisters pussy and tits for several years, so his interest did not surprise me. When I pulled out my cock, he grabbed it and started stroking it. Then he asked me to undo my pants so he could feel my ass. He pulled out his enormous cock and started rubbing it up and down my crack. He put the head of it against my ass hole, but could not get it into my very tight ass. He turned me around and asked if I felt like sucking his erect cock. I was amazed at the size of it since my brother's cock was longer than mine, but very thin. I took it and sucked it for a few minutes and tasted his precum. He was so horny that it did not take long for him to fill my mouth. I swallowed it and loved the taste. We met before and after school for the whole year having sex with each other. Loved every minute of the excitement in that store room with that huge cock.

[abc123jd]

that is so fucking hot, nearly came reading it, I want that cock.

[Backdoorman]

The first time getting fucked was about 90 days ago. It was a big disappointment. I was having a MMF play time. when my friend went to fuck me he shrank and was not able to finish and they then switched to a toy. I have had plenty of toys but the first experience was a bust. I will say on the other hand I was able to fuck my friend a few days before that and as always loved that play time.

[mas8092]

I was around 46 when a guy came over and I sucked my first cock. He touched my ass and I came, all over the comforter. I kept sucking that cock until he jacked it all over me. My first anal was a few months later. It felt so good. I loved, and still love, the feeling of a hard shaft in my ass. Kinda out of practice. But I now know it is the way I want to play.

[dick_pumper]

I've been fucking my ass with my fingers, dildos, vibrators , plunger handles, basically anything I could stick up there would do. I finally was fucked by a real cock about a year ago. He went in slow, he was very concerned that he wasn't hurting me, and then after I assured him I was fine and it felt great he started to fuck me. sadly he didn't last but about 4 minutes. But it was still good. My most recent cock was with a guy in a motel room and he started off doggie style then wanted me to roll over on my back with my legs up around his neck so we could look at each other. he fucked me good. Real good. He asked if he could cum in me and I said yes, but then pulled out and stuck it in my mouth and came inside my mouth so I could swallow his cum. A very tasty treat.
(He did have a condom on while fucking my ass, then pulled it off before sticking his dick in my mouth)

[sysper]

i dream of getting fucked real good like u did especially in the missionary position where we gaze into each other's eyes & loose ourselves in each other's lust

[Grub Worm]

Was 12 the guy 13, hurt like nothing else. But for some strange reason I kept going back for more. Knew it was going to hurt, but still wanted it.

[lkld71]

I was 31. He was 16. I was newly divorced and was into porn big time. This was back when chat rooms had just started. I went into a gay chat room. He found me and we started chatting. I was super nervous about it but he kept asking over several days to meet me. So, one night, I made the decision to meet and I drove out to him. We met in a secluded place. He got into my car and we talked, awkwardly. He asked if he could suck me off. I allowed him. I came in his mouth and he swallowed every drop. I was so turned on by it that I pulled his out and did the same (that was my first time sucking). We were way out in a secluded area. He asked if I wanted to fuck. I said yes. So we got out of the car and got naked. He went first. He bent over the hood of my car. I slid inside him pretty easy as I wasn't his first. I fucked him for about 20 minutes before I blew. Then it was his turn. I assumed the position. He took his time since it was my first time. The head going inside felt awesome. Finally after several minutes, he was able to get fully inside me. He fucked me for what seemed like hours until I felt him throbbing and moaning prior to cumming inside me. It was so HOT!

[pole_smoker]

I was 31. He was 16. I was newly divorced and was into porn big time. This was back when chat rooms had just started. I went into a gay chat room. He found me and we started chatting. I was super nervous about it but he kept asking over several days to meet me. So, one night, I made the decision to meet and I drove out to him. We met in a secluded place. He got into my car and we talked, awkwardly. He asked if he could suck me off. I allowed him. I came in his mouth and he swallowed every drop. I was so turned on by it that I pulled his out and did the same (that was my first time sucking). We were way out in a secluded area. He asked if I wanted to fuck. I said yes. So we got out of the car and got naked. He went first. He bent over the hood of my car. I slid inside him pretty easy as I wasn't his first. I fucked him for about 20 minutes before I blew. Then it was his turn. I assumed the position. He took his time since it was my first time. The head going inside felt awesome. Finally after several minutes, he was able to get fully inside me. He fucked me for what seemed like hours until I felt him throbbing and moaning prior to cumming inside me. It was so HOT!

That's creepy and disturbing.

[bigtime2013]

i have not yet, sure want to with this guy who has a BIG 8" COCK, CAN HARDLY TILL I DO GET TO FEEL THAT DEEPLY IN MY TIGHT ASS ! I'VE HAD A DILDO IN MY ASS AND TOTALLY ENJOYED IT, ALL 6"S. Anyone close to me care to teach how - to receive, im waiting

[Fyrfytr]

I'm looking for someone to be my first...

[Curioustotry64]

GREAT THREAD!
My first time was earlier this year (Spring 2014). I'm 49 and divorced with 2 kids. I'd had strictly oral experiences on several ocasions up until then. Prior to 4-5 years ago I was strictly hetero, but had plenty of imagination, and had been sliding things into my ass, when the mood was right, since I was young. The orgasms are much stronger with something up there. The last couple of years I been able to cum just from a dildo pumping away back there.

For my first time being fucked, I met a bi couple (both fully bi) on line. We'd gotten together once before and she had been the center of attention while he and I spent plenty of time sucking each other off. He has a very nice 8" cock that is nice and thick as well. I'm a good 7" and thick, but not as thick as him.

The second time we got together the wife couldn't make it. I went to his place and we started hugging and rubbing out cocks together then made it to the bed where we got into a nice 69. I really wanted a real cock slid in my ass so soon after I asked him to scratch my itch. I was rock had as I got on all fours while he slipped on a condom and lubbed up. He fingered me a little, but being used to toys it didn't take too much to get me ready, although I hadn't taken anything as big as him yet. He was patient and slowly worked the tip of that wonderful cock into me. At first there was a little discomfort. He pulled out and them pressed the head of his cock back against my pucker and he slid in. Once I'm opened up I love the feeling of something sliding in and this was even better! I felt completely full and immediately felt that delicious tickle and tingle with a slight needing to pee feeling as his hard cock began rubbing against my prostate! He pumped slowly at first working the head in deeper. After 4 or 5 pumps my horniness took over and I pushed back on his next thrust taking his full length into me in one push. It was incredibly erotic and an incredible feeling for me to have my ass pressed against him thinking of and feeling his entire length buried inside! Soon he was fucking away in earnest with me pushing back into every thrust, my hard cock bouncing away below! I lifted my head and upper body up and could immediately feel more of that delicious feeling of his cock working my prostate. There is nothing comparable in my experience with women. It was intense and my mind was awash with the new sensations as my orgasm built slowly from deep inside. The orgasm worked its way to a crescendo and was much longer than a normal penis centered orgasm. I looked down and below my untouched penis was a pool of cum. He pumped away and finished in the condom and withdrew. He was amazed I'd cum, as was I. It was an incredible experience.

Being fucked by a guy and having sucked has not changed my love and appreciation of women. I prefer women and still have wonderfully dirty thoughts of what I want to do with them. I have a girlfriend now, who does not know my door swings both ways yet, so I haven't been back with the bi couple. I view this part of me as liking someone and not letting their gender get in the way. It also a way to open my sexual horizons to new forms of pleasure. Society (most men that is) think it's hot when women play together! Why should they have all the fun!

[adamdawn]

we are in Illinois . ive only had my wife and her strapon in my ass but feels so good ... she want s help fucking my ass and stroking a nut off in my ass then its her turn
6185621169

[berryhard]

My cock is hard as a rock reading this ! I've had great oral experiances before but an anal virgin. I have on many occasions used a 8" realistic dildo in my ass and I cum very hard with a thick dildo "fucking" my tight ass slow deep and hard. It's an amazing feeling and I can only imagine a real cock must be even more amazing.
I am looking forward to some day soon experiencing being penetrated anally and fucked for the first time. Until then I will just have to strike my cock and fantasize how it will be....

[Tatuaje]

I was 13 my first time. He was 15.

Our moms were best friends and as children we played doctor (probably a bit more than most). They had moved away for about 4 years, but moved back after his parents divorced. Our moms, both being single, spent a lot of time together, so we did too. One night, our moms decided to go out and left us alone. We were looking at an old Playboy and he asked if I remembered playing doctor with him. Of course, I did (and had a massive crush). He asked if I wanted to play doctor again and within minutes we were naked. Our "game" was much more advanced and, in no time, I was sucking on him. He was really hard and pulled out and climbed over my back, sliding his cock up and down on my crack, dripping precum on my hole and making me slick. He pressed against my hole and pushed in slowly. It hurt a lot but I didn't want him to stop. He got inside completely and began humping quickly until he came inside me. What a rush!

Being young, he got hard again quickly and fucked me 2 more times that night. After that, we were inseparable.

[adamdawn]

haven't had a cock from a guy .. my ife has a strapon that iike a lot ... n he loves fucking with it to... se sometime gets caried away with it but it gets her off to high there.. we ae in Illinois

[mrcumsalot]

I was 13 or 14 years old my first time. While at first quite terrified it turned out pretty amazing. It was my two older brothers who introduced me to male on male sex when our parents where out of town for the weekend and they were taking care of me and my sister. They took me into my dads workshop and initiated things by making me kiss their penis and eventually putting them in my mouth. The were very aggressive and cruel with me and this is when I learned that I was a submissive. Since then I have had only male on male sex

[JackTexas94]

I was a young teenager when topped by a friend in the 70s. We used Vaseline for lube and did it bareback.

[bi4asplay]

First time was on business trip. Got talking to another guy at the hotel bar, went to leave to go for a swim in the pool, he joined me. Afterwards he invited me up to his room for a drink. Went to his room got out of the wet suit wrapped towel around myself, he came out of the bathroom totally naked, he asked if I minded, he was nicely hung. He told me if I wanted I could drop my towel, which I did, I immediately got a hard on, we played around, then got into 69. He started licking my hole, horned me out, then he fingered me, then he asked if he could fuck me, I told him I never had been fucked. He went slow and let me get adjusted to his cock and he kept pushing till he was fully inside. He rode me good. We did for the next two nights of my trip.

Very hot

[Whitetedy]

my first time was in a gay bar in the bathroom IT WAS SO BIG WAY BIGGER THEN MINE I MEAN WAY BIGGER I think it was the first time i fell in love with a man it hurt at first but then I didnt want him to stop.I noticed people were kinda trying to look in the stall and god help me i didnt care I wanted them to come in. My main fantasy is now being fucked and a dick in my mouth OMGGGGGGGGG.The last time was two weeks ago in a adult book store it was so hot. I did have fun there was a hole but i was with someone in a room was hoping a cock would appear from the whole but it didnt happen.Sometimes I feel kinda like a girl when i do this does anyone else feel this way
Yes. I feel that way too. The first time I got fucked by a guy it was sort of a surprise. I got picked up in Times Square by and older man when I was 18. He asked me up to this hotel room and I thought he wanted to suck me off which had happened a few times already. But instead he and his roommate fucked and came inside me. Then they asked me to leave without satisfying me. At first I felt frustrated and used. But as I walked home I could feel the cum inside me and I felt like a girl too. I like that feeling and I discovered liked feeling girly. I began to crave that feeling. The next time I got fucked it felt incredibly warm.

[pole_smoker]

I was 13 or 14 years old my first time. While at first quite terrified it turned out pretty amazing. It was my two older brothers who introduced me to male on male sex when our parents where out of town for the weekend and they were taking care of me and my sister. They took me into my dads workshop and initiated things by making me kiss their penis and eventually putting them in my mouth. The were very aggressive and cruel with me and this is when I learned that I was a submissive. Since then I have had only male on male sex
That's sick and fucked up that this happened to you.

[david2230]

Hi, I haven't been fucked in the ass yet, but have had a dildo up my ass. Would you fuck me with your dildo?

[david2230]

I was 12 when my older brother took my underwear off me in bed and sucked me and stuck his cock up my ass. It hurt.

[sisboy]

Actually it was quite nice.I had been fooling around with small dildos and one of my wifes friends at the time was in jail and after I had sucked his cock a few times he talked the wife into letting him fuck me in the ass.I balked at first but after a few weeks of teasing me I was ready.My wife was already a pro at taking a cock in the ass so she helped me prep for it which is a pain in itself.When the time came after a few glasses of wine and being super turned on from sucking his cock it was go time.I did exactly what she told me to do and that was just do not push back or tighten up and you will be fine.It took a bit but once all the lube got in and he was comfortable I really enjoyed it.He knew exactly where to put his cock to massage my prostate and before I knew it I was shooting probably the biggest load I ever shot in my life.My dick got hard and out shot this load without me even touching my cock.It took him a while to cum but when he did he let loose a good load too.She does not see him anymore but always kids me about him taking my cherry.He got me sucking cock and while i do enjoy sucking cock I will take a cock in my ass on special occasion.There are not too many guys around like him that knew how to use his cock in an ass.He also had a talent for sticking his whole cock down my throat without tearing me up.Miss him.I wish he would come back for a reunion.

[pole_smoker]

I was 12 when my older brother took my underwear off me in bed and sucked me and stuck his cock up my ass. It hurt.
That's creepy and disturbing that he did that to you.

[billie43]

i am 72 and found my bi side at 62 have had mmf threesomes mmmm 4somes and watched people get fucked i was and still am just oral..but like you i have a lrge dildo that i have worked with and feel i am ready for my first anal recipt...and i truly believe it's imparitive that you loosen up before first time.... i fully believe the real thing will be so much better than a stiff hard dildo...although i'm beginning to like it.. i have one friend who claims to be "straight" but wants to fuck me...his cock is nearly identical in size to my dildo... and i am pretty sure he will be taking me for my first ride...thanks for your ;little story...makes me feel much more at ease...

[Oztrich]

My first time was strange. I remember the guy telling me he wanted to fuck me, and I really did not get what he meant by "fuck." It had not occurred to me that men like to stick their dicks into other men's asses. I was willing enough, but still not understanding until we were in the bedroom and I was face down with his incredibly hard cock touching my ass. He had lubricant in a tube, which he squirted around the hole, and then he inserted the tip and squirted a lot more into me. I felt my face flushing and was terrified and excited at the same time. I don't think I have been that hard either before or since. When he started putting his cock in, he did it incredibly slowly. He kept working it until it kind of "popped" in. I came almost immediately. After that I was hooked.

[lil4in]

I was 15 the boy I was with was also 15,he was big so the
first time hurt so after that I only allowed guys who were small fuck me no pain feels good

[HighwaysandBiways]

My first time was fine. I was 15 and he was early 30s. Underage I know, but I partly initiated sex and it progressed. He didn't have any lube and used saliva, but he didn't stick it in too far so it was painless.

My next time was with another guy who had a smaller cock, but had lube and so he fucked me deeper and I was sore the next day!

[man4girlgirl4man]

It was great! We were both very hot for each other, I told him I was an ass virgin and I wanted him to be my first and that really turned him on. He had a 9.5 inch huge thick dick but I was ready for it from years of fucking myself with much bigger dildoes. My advice to you rookies out there is to be prepared before you take you first ever assfucking. Physically prepared with lots of self fucking practice. And also mentally prepared to get fucked by a man and more importantly to like it a lot if it turns out that you do.

I did!!! I loved the physical sensation. I loved the whole role reversal vibe of being the one getting fucked and not the one doing the fucking like I always had before. I loved being manhandled and feeling his hands all over me as he fucked me. We made sure to talk about our mutual limits and any dislikes or deal breakers before the sex began and I advise that you ass virgins both tell your partner of this and that you also agree on whatever you or he doesn't want to do when he fucks you. I don't do pain and I hate verbal abuse of any kind - racially based or otherwise. And since I'm a white guy and I am sexually drawn almost exclusively to very well hung black men when I'm in gay mode, I don't want any hate or abuse of any kind and unfortunately some people bring their totally non-sexually related personal hangups and baggage to the bedroom. I told him I would be into dirty talk and he could make me tell him I was his cocksucking slut white pussy boy girly bitch etc etc and that he could pull my hair and slap my ass when we were fucking doggy style and also that I was really into sex-kissing and lucky for both of us he was into that too.

Relax, demand a condom, make sure you're comfortable about the man who takes your ass for the first time in your life in every way that matters to you. And then use as much lube as you decide too. That first hard dick will either feel very very good when it's fucking your ass or it won't. But you'll never know which unless you try it at least once.

Sex is the best thing about life. So if your desires are telling you to get fucked by a man you really should try it once and then see what happens after that.

Happy fucking to you all and have lots of fun every time you fuck or get fucked!!!!

[KevsBi]

I was 21 and a guy that I had suspicion was bisexual and older than me was buying me drinks one night and we were just having a great time talking and shooting pool and at closing time he asked if I would like to go back to his place. I had been with a guy before so I knew what was about to go down. Long story short we got back to his place and as we were making love, he started massaging my anus and it felt wonderful. He asked if it would be ok to let him fuck me. He was experienced and very gentle. I took him a few minutes to get it in but patience and lots of lube led to a wonderful experience of losing my anal cherry.

[Oztrich]

Weird experience. My FWB made a run back here this morning. This is the third time! The drive is huge, so he must really want it. He called on the outskirts of town to say he was coming in, and hoped I would be available this morning. I headed directly for the shower, scrubbed like a wild thing, and waited the few minutes for his arrival.

When he got here I was dressed, but all set to go. When he came in we went right to the bedroom and undressed. After the usual 69, he wanted me on all fours, butt in the air. I felt the cool air from the a/c touch me in the right place, then felt his lubricated middle finger explore then penetrate me. His finger slid in very easily, and he pushed it in as far as it would go. The next thing I knew, I could feel the tip of his penis, and knew it was bare. He probed a little, but to my surprise, he was all the way inside in just a second. There was no discomfort at all. The tip kept hitting my prostate area, and I felt sperm leaking out of me. When he came, he pushed in really hard, harder than usual. He stayed there for awhile before pulling out. I keep asking to get pics, but he keeps refusing. He is in the shower right now, and planning to head right back home. This is nothing to do with the "first time" theme, but it surprised me a lot just how easy it becomes. It really is easy to understand why some women absolutely love anal.

[play times]

My first time was with a neighbor a few doors down, I was 14, and he was late 30's. He always talked to me when he passed by, and one day he asked me if I'd like to earn some money helping him paint a room. Being a boy of 14, I readily excepted it, at that age money was hard to come by. Saturday morning, I was at his door, ready to paint and earn some cash. He told me that he was waiting for the paint to arrive, almost one hour had passed, and no paint, but I did not care, because while we were waiting, he showed me some hard core gay porn magazine, that got very aroused and the last thing in my mind was painting. As we were looking at it, he started to stroke his cock over his pants, soon after he reached over and started to stroke mine. My heart was pumping so much, and at that time I knew I wanted to do the same to him, and in no time his massive hard cock was out of his pants throbbing and using precum. He took mine out as well, started to stroke it, and in no time he was sucking it. I was so turned on, that i almost came instantly, sensing that, he stopped and sat back. Well!! he did not have to say anything, as I took to my knees, and started to stroke and suck his massive hard cock, like a toy at X-Mas. After a while, he stopped me tuned and told me to fuck his ass, I hesitated at first, but as I watched him lube his ass, I knew it was happening. He put a condom on, and before I knew, my cock was all the way in his ass. As I pumped his ass, he asked me if I'd like to try it, at first I said I was not sure, but as I saw my cock go in and out of his ass, I grew more and more anxious to try. I came like never before, but I was still horny as hell, in no time, I was on my knees at the edge of the bed and he stood on the floor by the bed. He started to lube my ass slowly inserting a finger and moving it in a circular motion the sensation was so great, that i could not wait to have the bulging head of his cock pop my now ready anxious hole, but he took it slow witch made me relax, he started to insert another finger, each time going deeper, and rotating more getting me nice and loose. He removed his fingers, was going to put on a condom, I stopped him and said let me suck it some more. After sucking him for a while, I told him I was ready to try his massive hard cock he was a good nine inches and thick. He put on a condom, lubed my ass some more, and told me to relax. He put the head of his cock against my hole applied a bit of pressure and left it there, I started to push back slowly, and all of the sudden, it popped in. It hurt a bit, but I knew I wanted more, he started to push very slowly, allowing me to stretch to accommodate his thick cock. I squirmed both with pain and pleasure, but the pleasure was far better then the pain, slowly I took every inch of his massive cock. After I was nice and loose, he started to fuck my ass slowly at first, after a while he picked up the pace, and I would meet his every stroke by pushing back making sure his balls banged my ass with every stoke. After a while I sensed him tighten up, grabbed my hips, and with a few hard thrusts came like a mad man, I felt this hard hot gush of cum that I thought would not stop. Finally he pulled out his cock, removed his condom, and I quickly took his still hard cock in my mouth and sucked him dry. We cleaned up and not much was said, but I knew I was hooked on cock. We hooked up a few times more, but soon after he moved and I never saw him again. I'm blessed that My wife knows about my desire to have cock from time to time, but she also fucks me some times with a 12" strap on that we have, and I love every inch of it...

[jimtom56]

my first time getting fucked in the ass was 4 years ago by a fiend and 2 of his buds. i had already sucked all 3 off that day and later they wonted me to try it. my fiend was the first to do it. at first it was a little painfull going in but the more he fucked me the better it felt. being he had cum already that day it took him longer to cum in my ass but it made the other 2 easier to inter me when they fucked me took 3 loads in my mouth and 3 in my ass that day now i get fucked at least 2 times a week by them love it

[sammyazza]

It hurt. i was young, he was older. i let him do it so i cant really complain.

[pole_smoker]

My first time was with a neighbor a few doors down, I was 14, and he was late 30's. He always talked to me when he passed by, and one day he asked me if I'd like to earn some money helping him paint a room. Being a boy of 14, I readily excepted it, at that age money was hard to come by. Saturday morning, I was at his door, ready to paint and earn some cash. He told me that he was waiting for the paint to arrive, almost one hour had passed, and no paint, but I did not care, because while we were waiting, he showed me some hard core gay porn magazine, that got very aroused and the last thing in my mind was painting. As we were looking at it, he started to stroke his cock over his pants, soon after he reached over and started to stroke mine. My heart was pumping so much, and at that time I knew I wanted to do the same to him, and in no time his massive hard cock was out of his pants throbbing and using precum. He took mine out as well, started to stroke it, and in no time he was sucking it. I was so turned on, that i almost came instantly, sensing that, he stopped and sat back. Well!! he did not have to say anything, as I took to my knees, and started to stroke and suck his massive hard cock, like a toy at X-Mas. After a while, he stopped me tuned and told me to fuck his ass, I hesitated at first, but as I watched him lube his ass, I knew it was happening. He put a condom on, and before I knew, my cock was all the way in his ass. As I pumped his ass, he asked me if I'd like to try it, at first I said I was not sure, but as I saw my cock go in and out of his ass, I grew more and more anxious to try. I came like never before, but I was still horny as hell, in no time, I was on my knees at the edge of the bed and he stood on the floor by the bed. He started to lube my ass slowly inserting a finger and moving it in a circular motion the sensation was so great, that i could not wait to have the bulging head of his cock pop my now ready anxious hole, but he took it slow witch made me relax, he started to insert another finger, each time going deeper, and rotating more getting me nice and loose. He removed his fingers, was going to put on a condom, I stopped him and said let me suck it some more. After sucking him for a while, I told him I was ready to try his massive hard cock he was a good nine inches and thick. He put on a condom, lubed my ass some more, and told me to relax. He put the head of his cock against my hole applied a bit of pressure and left it there, I started to push back slowly, and all of the sudden, it popped in. It hurt a bit, but I knew I wanted more, he started to push very slowly, allowing me to stretch to accommodate his thick cock. I squirmed both with pain and pleasure, but the pleasure was far better then the pain, slowly I took every inch of his massive cock. After I was nice and loose, he started to fuck my ass slowly at first, after a while he picked up the pace, and I would meet his every stroke by pushing back making sure his balls banged my ass with every stoke. After a while I sensed him tighten up, grabbed my hips, and with a few hard thrusts came like a mad man, I felt this hard hot gush of cum that I thought would not stop. Finally he pulled out his cock, removed his condom, and I quickly took his still hard cock in my mouth and sucked him dry. We cleaned up and not much was said, but I knew I was hooked on cock. We hooked up a few times more, but soon after he moved and I never saw him again. I'm blessed that My wife knows about my desire to have cock from time to time, but she also fucks me some times with a 12" strap on that we have, and I love every inch of it...

WTF that's sick and disgusting. People like your neighbor belong in prison.

[a2smith09]

It was great! Fortunately my first was very experienced and knew what he was doing. he took his time, built me up till I wanted it, prepped me well, drove me crazy with foreplay, lubed me well, entered me slowly, and slowly fucked me till I relaxed before he fucked me hard. It was virtually painless and I had a couple of orgasms before he came. Overall it was a very good experience.

[Kev-Bi-Maine]

I was in my late teens. Met a guy in SoCal and we went to his place. He offered a massage. I took him up on it. He undressed me and massaged me.....undressing as he went. He used lotion and ran out while lubing up my asshole and his cock so there wasn't quite enough but he did it anyway. Hurt like hell the whole time, he came in me and was done. I wanted more but he was done. Got it another time in a rest area in my car in Massachusetts.....hurt but was a good hurt.

[void()]

Interesting, a new and enjoyable experience.:)

[itsnormy]

I was 11, boy same age, did it before I knew it was supposed to hurt, was MAGNIFICENT, if left to one sex act for the rest of my life, it would be anal...I envy women who have THREE holes for pleasure and we are stuck with just TWO..........*S*

[darkeyes]

Trust me.. his 1st effort wos a dismal failure and wen I relented and let him have second bite at cherry he successfully managed but it wosn't a gr8 success... ther wos no 3rd bite.... he became x....

...not kind of story u wonted 2 hear? O well...;)

[Cutiliae]

My first time getting ass fucked was back in 1998 when my married FWB was visiting me and we had some alone time. For years when we get together I give him blowjobs; sometimes 3 to 4 in a single day when we were younger. Anyway, on this visit we woke up in the morning and I started to give him a morning blow. For years I had been thinking of having him fuck my ass but I never brought it up.

As he lay there enjoying my oral skills I stopped and said that I wanted to "try something." I got out my tube of KY and started covering his cock with it. As I got up and began to straddle him he said, "what are you doing?" I didn't respond and positioned myself over his cock and lowered down and allowed his cock to enter me. It went in easily and I started moving up and down supporting myself by placing my hands on his chest. He put his hands on my waist and met my motions with his hips. After about 3 to 4 minutes he groaned and reached his crisis inside of me. We never did it again but he brings it up sometimes with a giggle and says it was the day I "molested" him.

[the_closet_case]

I was 28, and had been dealing with my bi/homosexual urges as long as I could remember. My wife was out of town, and I'd been watching gay porn, jerking off, sitting on a dildo-- and chatting online with local guys. I had been talking with one gay dude who was local pretty frequently, and the second night she was gone told him online that I was home alone. He immediately invited me over. I went back and forth but took him up on it, and drove to his place. I remember my cock being semi hard the whole time, and I was trying to talk myself out of it. Of course when I got there he was already just in a bathrobe and gay porn was playing on this huge TV. We sat on the couch and talked a bit, and within a few minutes his hand was on my crotch, fondling my cock through my pants. I was nervous, but then he pulled out his cock and put my hand on it. That was just-- wow. One thing led to another, and we sucked some (and I found out how hot sucking cock is), and then he wanted to fuck-- he started fingering my ass and I was hot for that. He knew it was my first time, but by that time I was pretty turned on. He put on a condom, lubed it up, and I sat on him.

It. felt. glorious. I swear my first thought when I bottomed out on his cock was "finally". I rode him until he was about to shoot, and then I exploded all over his chest. i felt guilty as hell for cheating on my wife, but I just couldn't deny that I wanted sex with him and that it felt really, really good. And thus my bisexual rollercoaster began. My wife still doesn't know I get turned on by men.

[void()]

Trust me.. his 1st effort wos a dismal failure and wen I relented and let him have second bite at cherry he successfully managed but it wosn't a gr8 success... ther wos no 3rd bite.... he became x....

...not kind of story u wonted 2 hear? O well...;)

* holds up a scorecard reading "9.5", sits snickering and chuckling himself out of his chair *

[darkeyes]

* holds up a scorecard reading "9.5", sits snickering and chuckling himself out of his chair *
Nope, Voidie.... even wen he did manage penetration, his scorecard (in me journal) reads nower near 9.5 and ther r far more points available than 10...

[void()]

Nope, Voidie.... even wen he did manage penetration, his scorecard (in me journal) reads nower near 9.5 and ther r far more points available than 10...

Sorry, was scoring the story. It was a bit of a chuckle for me. The guy was not the chuckle rather the story and your bit of brashness in;

...not kind of story u wonted 2 hear? O well...;).

I felt your disappointment from the experience with the guy, and then recalling it. Some people in the world seem incapable of loving. Would that not so, think we'd all be a good deal better off.

[BiJackfla]

Well don't think this is weird but my first ANAL was at 12 going on 13 back in the Late 70's older man friend of my Hippie Mom! I started sucking COCK about 10 my friends and my Older Brother I was hooked!! Well the Friend would stay over a lot over night and like most nights I was in the Bath trying to beat my dick when in walks (Friend) naked after leaving my passed out Mom again! He closes the Shower Curtain about half way (100% True Story) and stated to stave! one problem he had a raging hard on a nice curved Cock the first one I ever saw and I am Staring!!! He gets done and turns to me his COCK is now facing me and I'm still staring and he said grad it and I did!! Next thing I know I am sucking his NICE Curved Cock! Well long story short Not REALLY he lets me suck his Cock off and on and eat his CUM! Which I already had swallowed CUM at 12 before! Well I had been sticking little things up my Ass like a Hair Brush Handle and things in the bathroom and my Friend had rubbed his cock on my hole but never pushed it in! But somehow I don't remember how or when I was Sucking his cock in the Bathroom one night and ended up with the Head of the (Friend) Cock on my Hole and pushing in and out slightly! He used some lube and pushed and his HEAD popped right in my Hole and I felt some Pressure a little pain he was bigger than the Hairbrush Handle but in he went about half way and started slowly pumping! Well I just found something new I couldn't get enough of late 20's COCK for the next year! Then the Worst happened they Broke up and we moved away no more 20 Something COCK for me! But I still had a Friend once in awhile and met my Girlfriend and then I found PUSSY! But I still have one or two COCKS around I get to see once and awhile. Some may say that's fucked up but that was the 70's and that Love everyone shit!

[pole_smoker]

Well don't think this is weird but my first ANAL was at 12 going on 13 back in the Late 70's older man friend of my Hippie Mom! I started sucking COCK about 10 my friends and my Older Brother I was hooked!! Well the Friend would stay over a lot over night and like most nights I was in the Bath trying to beat my dick when in walks (Friend) naked after leaving my passed out Mom again! He closes the Shower Curtain about half way (100% True Story) and stated to stave! one problem he had a raging hard on a nice curved Cock the first one I ever saw and I am Staring!!! He gets done and turns to me his COCK is now facing me and I'm still staring and he said grad it and I did!! Next thing I know I am sucking his NICE Curved Cock! Well long story short Not REALLY he lets me suck his Cock off and on and eat his CUM! Which I already had swallowed CUM at 12 before! Well I had been sticking little things up my Ass like a Hair Brush Handle and things in the bathroom and my Friend had rubbed his cock on my hole but never pushed it in! But somehow I don't remember how or when I was Sucking his cock in the Bathroom one night and ended up with the Head of the (Friend) Cock on my Hole and pushing in and out slightly! He used some lube and pushed and his HEAD popped right in my Hole and I felt some Pressure a little pain he was bigger than the Hairbrush Handle but in he went about half way and started slowly pumping! Well I just found something new I couldn't get enough of late 20's COCK for the next year! Then the Worst happened they Broke up and we moved away no more 20 Something COCK for me! But I still had a Friend once in awhile and met my Girlfriend and then I found PUSSY! But I still have one or two COCKS around I get to see once and awhile. Some may say that's fucked up but that was the 70's and that Love everyone shit!
That's fucked up that you were sexually abused by your so called "friends" and their older brother, and that family friend. People like that are sick and belong in prison as they are into sexually abusing people.

[irishbob]

I was fucked for the first time last week. I am only 18 and it was a big event for me. It was in the home of a married bi-couple and the wife got me well prepared for taking my first cock from her husband.
I don't want to re-write the experience as it can be read on my thread "Need Older Men"
I had longed for this for some time and I have to admit that it was most enjoyable, especially having a load of cum up me.

[oliveanddark]

can't tell the age, a friend of mine and I were in a campground bathroom playing around, we started talking about what you can do to girls, then I asked him if I could try doing that to him to practice. Well, he agreed but only if I would let him do it to me also. We took our pants and undies off and his cock was way smaller than mine but uncut. I wish we had known about sucking, we did not even know about that. He got up next to the wall and bent over and I tried to get it in him, no way, I was way too big. So, he then reminded me of my agreement. I remember thinking yikes! I looked down there and touched his dick, it was rock hard, so nervously I bent over in front of the wall and put my hands up on it, he got behind me and at first it would not go in, but suddenly it did and it felt strange, but kind of good. He fucked me for awhile, I was nervous about it and it started to get a little sore feeling, so he pulled out and we got dressed,went on about our business. The next time I got it, it was an older male and a few years later although I was still young. He used Crisco and it hurt really bad, he was very wide,and rough.

[pole_smoker]

can't tell the age, a friend of mine and I were in a campground bathroom playing around, we started talking about what you can do to girls, then I asked him if I could try doing that to him to practice. Well, he agreed but only if I would let him do it to me also. We took our pants and undies off and his cock was way smaller than mine but uncut. I wish we had known about sucking, we did not even know about that. He got up next to the wall and bent over and I tried to get it in him, no way, I was way too big. So, he then reminded me of my agreement. I remember thinking yikes! I looked down there and touched his dick, it was rock hard, so nervously I bent over in front of the wall and put my hands up on it, he got behind me and at first it would not go in, but suddenly it did and it felt strange, but kind of good. He fucked me for awhile, I was nervous about it and it started to get a little sore feeling, so he pulled out and we got dressed,went on about our business. The next time I got it, it was an older male and a few years later although I was still young. He used Crisco and it hurt really bad, he was very wide,and rough.
That's fucked up that you were sexually abused by your so called "friend" and that older guy. People like that "friend" and the older guy are sick and belong in prison as they are into sexually abusing people.

[Tuffnuggies]

First attempt was with a friend at 14. Hurt too much so we stopped.
Fast forward 25 years, and I met another bimm, at a vacant aprtment I was renovating. We we supposed to have been there for mutual, but he flipped me of all fours, and began rimming me. (That was the first time for that too) I got so horny, I must have sent him a signal. Because he slipped his cock inside me, and pounded me. Once he got past my sphincter, the discomfort went away. I began ordering him to fuck me as deep as possible. I came all over the floor. Now, I want to try a long thing cock.
Once you have that first taste.. You're hooked

[oliveanddark]

The friend incident we were both kids and experimenting together and that was basically fun, so that was different, the other guy, the older one, I really considered trying to have him put in prison for rape since basically, that is what it was, but did not want to go through the hassle but I warned him to stay away from me, which after a couple of attempts to get with me again, he did. The older guy got me, a young teenager, stoned and half drunk, then stranded at his house and told me if I would play right, he would give me a ride back to my job, if not, he would make me late to work and I would get in trouble. So, I wound up on his couch with my pants down. I know, I was young, naive, and stupid. I remember wondering why he had so many cans of Crisco laying around, this was the 1970s and it was popular to use for anal by the Gay crowd. This person was the classic "ChickenHawk", and I stayed away from cocks for a long time after that incident. A guy with a cock like that, short but almost the width of a new I phone and round and fat with a big head, that took his time and was not so rough, I think today I would really enjoy in me.

[BiCuriousVAN]

My first fuck was about two months ago. I had wanted to try for a long time, but I couldn't find anybody I thought I would be comfortable with. On any dating sites, as soon as people saw anal, that was all they seemed to see, so had a lot of people who wanted to fuck me and fuck me hard. They missed the part of me being a virgin, being nervous and wanting to take it slow.

I finally posted an ad on craigslist and was very specific of what I wanted and who I would and would not respond to. While I had a few hardcore responses, I get a few that seemed to get it. I got one response from another bi guy, albeit with a bit more experience than me. We corresponded a few times and agreed to meet a few days later, which gave me a few days to get my ass ready. I have a dildo that I used to get me ass ready with of course lots of lube. We met at a coffee shop to chat. We both felt very comfortable with each other and I brought him back to my place, which was nearby. We undressed each other and started with a bit of oral. He was about 7" and average girth. He started lubing up and fingering my ass and getting me ready. He lubed up my ass some more, as I slide a condom on his cock and lubed it up. I lay on my back and put my feet in the air. He slowly slide his cock inside me. I felt a bit of pressure at first, but no pain whatsoever. I was amazed at how easily his cock slide inside me. Once he was fully inside me, he started fucking me, as he stroked my cock. He shot his load at the same time I shot mine. I was amazing and I can't wait to do it again. I would also love to top somebody. He had fucked a few men and women before and so knew what he was doing, which made it great for both of us.

I think the key for me, was finding the right person who knew how to be gentle and me doing some prep work to get my ass ready.

[Bradw]

I was 32 yes I was with girls and straight ! I met that guy online actually it was dating site he liked my pica, I texted him I'm not gay but thanks !!! He replied I like straight guys it was interesting!! He was bottom :) after few months he convinced me to meet which we did he picked me up and we went to his place !!! Ok now we are in his room ! He touched me and starts to take my pants of and he got naked and I did too the first time I touch a guys penis in my life it felt good so he gave me blowjob which was great never felt like that before I rubbed his penis then I start doing him then I stopped and asked him if he wants to do me he did but he was really bad it hurts it was doggy style then I asked him to get on his back then I ride his !!!! It felt so good inside to the point I came like crazy ,,,, it was the first and last time in my life but now I really want to do it again it felt so good

[Bradw]

You should it feels good

[DMercator]

At 56 yo I'm somewhat late cumming to the show. My first time was just this last year. I was fortunate enough to have an experienced friend who made the experience wonderful. My friend is a few years older than I am, but has a very nice body. His cock is slightly smaller and thinner than mine, probably about 5 1/2". Just about every time I've seen him it was stiff and sticking straight out from his body. If you're like me, one of the pleasures of playing with another man's cock is that it feels so different from your own. Even his stiffness feels different from my hard-on, more springy. lol.

I've been able to take him all the way down to his balls without gagging... well at least not very much. In the two times we've been together, I've gotten him off both times. He's only the second man I've had cum in my mouth and I have to say I like it a lot. It seems almost a contradiction to feel a sense of control and empowerment while you're on your knees sucking another man's cock, but there's a sense of accomplishment seeing him fall back on the bed in breathless satisfaction and knowing I did that.


My early guy-guy experiences as a teen were all on the receiving end (I always regretted not returning the favor). My later experiences guy-guy were with my wife and, while we sucked each other, our cumming was happily in, on and with her. So, as silly as it sounds at my age, I haven't fully enjoyed the pleasure of oral with another guy until just recently.

My new friend is also very experienced with anal. He isn't the least bit pushy on the topic and would probably have been perfectly content with just enjoying some mutual cock sucking, but I've known from the start that the thought of our fucking each other made him horny as hell. Frankly, I've never felt like the object of someone else's desire quite like I do with him. I've been with horny women who couldn't wait for me to fuck them and horny guys that were super turned on by my cock, but I've never had someone that couldn't wait to rip my clothes off because he couldn't wait to fuck me.


I'm not submissive or famine in any way, but for the first time in my life I had an inkling of what a women must feel like to have a man lusting after them. I'm not sure how I feel about that. Both horny and a little bit uncomfortable I guess, but mostly horny.

For my part, anal has been one of those embarrassing things I could barely admit to myself, much less to someone else. But he has a kind of easy going confidence that put me at ease. He's been an experienced friend who knows what he's doing and what it's like getting fucked for the first time.

Frankly, I couldn't I've asked for a better experience. It ended with him cumming in me (safe sex) and me shooting all over myself at the same time. While being a top isn't something that turns me on the way being a bottom now does, I've promised him the next time we were together I'd return the favor. Knowing that the mere thought of me bending him over and taking him from behind has him rock hard every time he thinks of it makes it a bit of a turn on for me as well.



All of this has made a big change in my fantasies, desires and even choice of porn. I want to be fucked and I want to see my friend writhing in pleasure on my cock. I want to be on my knees sucking my friend's cock or even my friend and another guy at the same time. I'd love to feel him cum down my throat while someone fucked him or, better yet, to be on the receiving end of that combination.


Damn I'm horny. lol

[si-cock]

I've not been fucked yet but I so want to have a guys cock in my ass, I have used dildo's and really enjoyed the feeling.

[LatinoBoyy]

I was about 18 and he was much older than me. He picked me up from my house and took me to his. I sucked him for quite a while, he had a nice thick cock. He asked me if i have ever been fucked yet and i said no. He asked me if i wantd to try and i said yes. He had me lay infront of him on my side and he lubed my asshole and put one finger in. He fingered my asshole for a couple minutes then i felt him rub his dick on my hole. He slowly started to push it in til it started to hurt. He said for me to push back when im ready. It was hurting but i wanted his cock inside me. So i slowly but surely got his cock all the way in, and damn it felt so good. He started to fuck me and i culdnt help but to moan like a girl getting fucked. I was suprised i got it in because how thick it was. He fucked me til he blew his load in me. Then he told me, congratulations, youve just been bred.

[LovingLingerie]

My first time was about a month ago. I'm in my 50's he in his 60's. He is gay and has always told me he wanted me. We are great friends and eat, drink and hot tub together. This night we were both pretty buzzed and I told him I wanted him to fuck me. We went to his place and began fooling around. He is a top and took control. I submitted to his control. He blew me and then began eating my ass. I was face down pushing back against his tongue. Oh my it felt good. He lubed me up and used a small toy on me. Then he entered me and slowly began to fuck me. The moment he entered me I was in heaven. He turned me over with force and I was his. He pushed my ankles to my shoulder and began fucking me hard. I was meeting his thrusts just as hard. Because we were both pretty buzzed he couldn't perform very well. He pulled out and used the toy on me and jacked me off until I came. It was incredible. I can't wait until next time. We both will be sober and I'm going to deep throat him until he shoots into my throat. Then, hopefully, he will take me again and fill my ass with cock and cum. I have always been the alpha-male type, but submitting to him was an amazing turn-on. I guess that makes me a bottom. I will embrace it and do anything he wants.:oh:

[sysper]

sounded like a great experiance even if drunk........imagine what it will be like sober! :oh:

[blowjober]

For the first time, it always hurts, but I really enjoy it.

[LovingLingerie]

I know, I can't wait

[Blowjob Boy]

Ive been humped by guys a bit.....I loved the feeling of a cock between my bum cheeks, but never been penetrated though. I have topped a guy, and it was fantastic...but I always wanted to experience what it feels like to have a cock sliding into me

[Mbm215]

1st time was my early 20s. Used to go to a bookstore close by and jerk off in the booths. I knew guys would watch through the holes and always found that to be a huge turn on. One day when i went into the booth i could hear the guy on the other side taking care of himself while he was watching me, he moaned and asked if i wanted to cum in his mouth. I was kinda nervous, i liked being watched by guys but never thought to get sucked off by one. My hornyness got the better of me and i stuck my dick in the hole. He was amazing! I came in under 2 minutes. Went back a few more times and always left satisfied.

[Mbm215]

I was in my early 20s. Had a girlfriend at the time and had too sneak. I met him online and we talked a while before agreeing to meet. I was SUPER nervous and bailed on the him twice. Luckily he was understanding and gave me another shot. He was amazing, sucked me nice and slow working a finger into my ass to loosen me up then he licked my ass which drove me crazy. By the time he was done that i practically dove at his dick. I never sucked a dick before but as soon as it was in my mouth i was hooked. He seemed to like it too. Finally i was ready, he put me on my stomach and held his cock up to my hole. He worked it in nice and slow, wasn't long before i was pushing back, wanting every inch of him inside me. Once i was nice and loose he turned me over and put my legs over his sholders and pounded me HARD. He slowed down and asked if he could cum inside me. I couldn't say no it felt to good. He made me cum just from penetration it was the best orgasm I've ever had. I remember the ride home, he lived about a half hour away, i felt his cum leaking out of me. I had to pull over and jerk off using his cum as lube.

[12voltyV2.0]

I was in my early to mid 20s, the other guy was a bit older--around 30. Being with him was great and from the first moment he entered me--my first time for that---other than some slight pain at first--something "clicked in" and man--I wound up loving having him inside and fucking me. We had a period of being together for less than two weeks but it was a great two weeks. The guy was a pure stud sex machine. It not only felt great physically to be with him, but great in other ways too and in the "heat" of it--I really did not question it or feel strange about it. I was just enjoying it.

After our time though, I more or less put those memories "away" for years and was not with a guy again for at least a decade and a half later. In those years, I had a series of "things" with some neat ladies that were exclusive.

The desires to be with a guy came back and they started getting more and more intense and regular till I reached the point that I decided it could not be ignored any longer, so I started getting on the internet in its early days and started a slow move back to getting with guys again.

Once I did---I had said this time "No Anal" and held to that for a time, but then I had a more or less regular thing with this one guy and he started coaxing me back to giving anal a try again---with me eventually giving in. This time--he took his time in doing things like working me with toys and such and then slowly we moved to having him try to enter me---which this time took a few tries to be successful but one day---it all clicked again and man--I was surely enjoying the feeling of once again having a hard cock inside of me.

He eventually moved due to work and it took me almost year to find another guy that I felt good about doing anal again. Eventually that ended due to him having cancer and it has been hit or miss finding someone since then.

I don't do anal all that much--surely not nearly as much as I would like---but when I do--I surely enjoy it. Of course---done SAFELY.

What would be great is to be able to find a "regular" guy to get with who we have mutual trust regarding health status and all---so yes---we could do barebacking because let us face it--if you do like to engage in anal sex, either giving or receiving--it does feel much better and is "hotter" sex to do it bareback rather than the top wearing a rubber.

I guess that when it comes to STDs--the only sure fire way to EVER be SURE that you have zero chance of picking something up-is to NEVER HAVE SEX WITH ANYONE---but how realistic is that?? My god--there are plenty of cases of supposedly monogamous spouses of both genders who "stepped outside" of their marriage who brought home some "nasty" of one kind or another, so even being with someone you have been with for years, you can never really be fully sure that they are not "playing around" on you behind your back and also can never be sure that you are both safe health wise thanks to sex. That is the hard truth of things.

[mjohn]

I was about 17 and it was amazing!!! I went to an adult book store (books and magazines only) and I kept wondering around in the gay magazine section. I ended up buying a a magazine with both genders in it. When I went up to pay. The guy at the counter (who was extremely hot) asked me that he couldn't help notice I kept going back to the gay section and if I was into that. I said it did turn me on. We probable stood there chatting for a while and then he said he got off in a few hours and if I would back to his place. I agreed and went back to hip place and WOW!!! We didn't even making it to his bedroom for the first round. But we did for the second round and that when I first experience his cock penetrate me. I don't remember if it hurt at all but I do remembered it felt awesome.

[XYa@!$445]

i just had my first time yesterday. I have this fantasies for so long and it was kind of consuming me so i got alone this week and decided to try it. I went on a date with a shemale, she was nice, kind of shy and pretty. We arrived at the hotel, i got naked first and went to meet her. I first stared carresing her face and while she looked at me i felt the urge to just kiss her, so i did, It was a great kiss, passionate like i didnt have for a long time, then after a while i took off her dress. She had small breasts but nice to suck it, and tehn i wnet for what i was desiring for so long. i got on my knees and started to feel her cock onver her pantie, it felt nice. Then i took her pantie off. it was beautifull, it was half soft but i could see it was big and fat enough for me, and it was uncut. i touched a dick for the first time, it was intereting to do it, the and just licked the tip of her cock, the i likced the shaft and finaly i started to suck it. It was nice, diferente, but i imagine i would be more aroused by that. Anyway i stared to suck it, the tip and going down on her every time a litle bit. I tried to deep throat but i gagged i feel times. I did that for a long time.
After i looked at her, and she asked me if i wanna to try it, i said yes. I gave her the lube, she wore a condom and i bend over to her, the time has arrived. She lubbed my ass and stared to push it in, it hurted a lot, her cock was really fat, i asked her to stop and then try again. We tried a few times but it was still hurting and she asked me to spoon me. I guided her cock with my hands at my hole and she started to push back in, it was still hurting but she held inside till im used to and then started to push it again, after that ther was no pain anymore, and she started to fuck me. as she was geting it faster she lifted my legs more and more fucking me deeper. And for me i was enjoying it yes, but it was not that great pleasureas i had thought, it was like when i tried a didldo one time. She came while fucking me, and then she finished me with a blowjob with me cumming in her mouth.
I must say it was fun, i had to try it but i really expected more, i thought i could cum with her fucking me, but i actually felt nothing in that way. I guess my fantasies arouses me more than actually doing it, i have to process this but i dont know yet if this is for me, or maybe i could let time show me if i want to get more sometime.

[sysper]

congratulations for ur 1st time! looks like u learned somethings but probably need to learn more. i hope u continue searching urself.

[man4girlgirl4man]

For me it was almost as good as in my hottest fantasies. And I should have done it much earlier and much more often than I really did and I really have so far. But I've been making up for lost time recently. Find a hot sexual match and all sex is great!!

[roydo]

OMG My fantasy. Sucked a lot of cocks and swallowed all their cum. MMMM Cock and cum whore. But never have had the pleasure of being Fucked. I have dildos which i truly enjoy.
None of my blow buddies want to fuck me. I feel very feminine when i suck cocks and I want the pleasure of being 'Taken"
I am so horny right now reading your stories. Thank you all for sharing

[roydo]

My ex loved anal. She orgasmed more and told me she could feel my balls slapping her pussy. Whe she came she would tighten up so much it almost hurt my cock. Hope you get to do it more and enjoy it more. I'm looking for my 1st anal experience

[melbcuteboi]

My first time was to put it politely - Terrible. Finally after always saying ill never try anal under any circumstances, here I was all of a sudden throwing caution to the wind and thinking fuck it, i might love it as much as i do sucking cock. Unfortunantly I had this breakthrough at a gay sauna while getting it on with an older guy in one of the rooms, it started out hot but once i agreed to the anal he pretty much tried stabbing me in the ass with his cock and bearly any lube like i was just a fuck hole. I stopped it straight away and told him to go jump. After this I thought i had already crossed the line so I decided should the opportunity arise again I would give it another go.

It did arise again not long after and it was nothing simply short of fucking amazing. Ive never felt such intense sensations through my body in all my life. Mnd Blowing, even made me blow wth no hands touching other then his cock in my ass. What an amazing feeling!!

[cumlayme]

My wife and I have been in the Hotwife lifestyle for about 7 years or so. She has a lover from time to time but I don't play with other women, and sometimes it feels like I'm slowly becoming a Cuckold but that's another story :). My first time being fucked by another guy was last year. My wife's lover came to stay with us for a weekend and they took over our bedroom and fucked all of Friday night and most of Saturday. We all got into the booze and my wife ended up having a little too much and fell asleep after being laid by him and we didn't want to wake her up for awhile. He came down into the kitchen wearing my wife's house coat which was funny and I ribbed him about looking so sexy lol. He said "ok now it's your turn", he took it off and said you wear it so I can see what it looks like on you. I started to put it on over my t-shirt and joggers and he said "no no, you have to be naked underneath like I was".

So I laughed and undressed and as I was stepping out of my joggers I had to bend over a bit and he commented "Holy shit dude, you have a really hot ass and don't take that as a gay thing, I mean you do have a hot ass for a guy". I laughed again and said "yeah Cathy tells me the same thing". Now by this time we both were pretty loaded up with booze and neither of us had much inhibitions. He said "look, I'm still horny as hell and Cathy is useless for awhile, would you consider letting me fuck your hot ass?" I laughed and said "yeah whatever"! He said again "no really, I'm not gay and I'm sure you aren't either but hey it's just sex and you're providing me a hole to fuck and I promise I'll go easy like I did when I fucked Cathy in the ass (which she would never let me do lol). After some constant prodding by him and a few more drinks I said "ok what the hell, lets do it".

He smiled and ran upstairs and soon returned with a bottle of lube. I asked him "where's the condom?" He said "now where the hell am I going to get one of those? I've been fucking your wife without one for almost a year and she didn't get anything from me and obviously I didn't get anything from her so it's pretty obvious we're not going to get anything from each other right?" I thought about it and said "yeah I guess you're right". Again he smiled but this time it was a really seedy look like he conquered this battle lol. He got me to lie on the table then put my knees up by my chest. Then he squirted lots of lube on my hole and proceeded to slowly work his fingers in one at a time until he got three into me which took some time and I started to enjoy it instead of the pain that it started with. Then he squirted a bit into my hole then squirted a bunch of it onto his cock and spread it well with his hand. I was nervous as he put the head of his large cock (much bigger than me which is why he's fucking my wife and I'm not lol) up to my hole and started to work it in. He was very gentle about it and there wasn't much discomfort. After he got his cock in about 3/4 of the way he said "are you ok?" and I said "yes it feels good". He said ok and started to fuck me harder and deeper.

Within about 5 minutes he was lying almost on top of me and had me pulled out so my ass was out over the table edge and he was supporting me. He began fucking me very hard and I could feel and hear his balls slapping against my cheeks. He started sucking and biting at my nipples the way he always does as he's fucking my wife and fucked me like he owned me and I have to admit at this point I didn't mind being owned lol. After about 15 or twenty minutes he started breathing really hard and said "I'm going to cum, can I cum inside of you"? At this time it felt so dammed good being fucked like a woman that I heard myself say "Yes yes, breed me like you do my wife" and thought to myself was that me that just said that? Now he was slamming into my ass real hard and I swear I could feel his cock get even bigger and I soon felt his cock throbbing as he was pumping me full of his sperm. When he was done he slowly pulled out and said "fuck man, you should rent out that pussy, it's amazingly tight" and laughed. I laughed as well and said "it should be, you're the first one in there". When he was completely out I could feel his cum running out of me (which was surprising considering how much of it he had pumped into my wife over the last day and a half) and it was then that I realized what it felt like for a woman when cum runs out of her pussy. When he started walking over to the counter to pick up his beer the first thing I saw in the doorway was my wife with a big smile on her face.

I was shocked and didn't know what to say. She started clapping her hands which made him turn to look and started laughing when he realized she saw what happened. She said "well now, that's perfect. You finally found a way to be useful at sex besides your mouth that is (I'm good at licking pussy lol). She looked at him and said "was his pussy tight?", he laughed and said "yes it was really tight but not as nice as yours babe". She smiled and said "well I guess you'll be fucking us both from now on". I was a little shocked and said "no I don't think so". She smiled and said "yes I think so and if you don't agree to it then I'm going to tell all your buddies about my lover and about how he fucked you and how much you enjoyed it".

All I could say was " shit, yeah ok fine". He patted me on the shoulder and said "don't worry, it's just between us and we'll all enjoy it". I felt a bit better when he said that, until he said "and oh yeah, when I fuck you you're going to wear Cathy's panties for me to take off". I knew I was screwed more ways than one right there and then lol. But to finish this off, I really do enjoy being fucked hard and deep by him and wouldn't think of stopping now lol. And yes I do love to look at pussy and wish my cocklet was big enough to satisfy my wife or another woman, and I would never kiss men and never look at men wanting to have sex with them. So I'm a forced bi and enjoying it :)

[DomBot61]

My first anal experience was at 40. However, I found myself a victim of date rape. Needless to say it was brutal and bloody.

[Superbtm53]

My first time I was underage (16) and it was with a friend, and it wasn't exactly consensual. A friend took advantage of me being passed out (we had gotten into some liquor at another friend's sleepover birthday party), and I didn't wake up until he was just about done. So I won't talk about that. I will however, talk about what I consider my actual first time.

It was a couple of years later and I was with a very good friend of mine. We were pretty inseparable, and pretty much did everything together. He was one of the only people who knew about my prior experience and never held it over my head (I had a lot of mixed feelings over that experience, including shame and guilt, and he actually was my biggest supporter). Well, it was a Friday night and we had just gotten back to his place after a night of hanging out in town and driving around (we lived in a small town and there wasn't a whole lot to do). We were going to play some video games and watch some movies and just hang out for the night. Nothing felt different between us, there was no sexual tension or anything like that. We were just sitting on his bed (which doubled as his couch) watching one of the Friday the 13th movies ( I think it was the one with Corey Feldman). The lights were off to enhance the atmosphere (seriously, who watches horror movies with the lights on?), and he just looked over to me and said "you can take your shoes off if you want." Which I did and leaned back against the wall to continue watching the movie, and he followed suit.

A little while later as I watched the movie, I felt his hand touch my knee. It was gentle, and could have been chalked up to an incidental brushing, not a big deal. But then it happened again, and this time the touch lingered for a moment. My stomach knotted in unanticipated excitement at his touch, and then he began to run his hand up my leg and to my inner thigh, and he began to stroke my cock from the outside of my pants. I was stunned by his advance, but really turned on. I looked at him, and he just smiled at me and said "Are you just going to sit there?" as he started to unbutton and then unzip my jeans. He got off the bed and pulled my pants off, and then my boxers followed. He took off his clothes and his cock was rock hard. He motioned for me to lay down on the bed, and took my shirt off and I obliged. He climbed up on the bed and pushed my legs apart and climbed between them. He ran his fingers over my chest, and then over my cock, and he began to lick the head, and then he took me fully in his mouth. As he sucked my cock, his fingers began to wander around my ass, and eventually one entered me. He was curling his finger around inside me, moving it around in a circular motion, and then another entered me and he began thrusting them into me while he sucked my cock.

Then he stopped sucking and pulled his hand out from between my legs. He he hooked one of my legs at the knee and pulled up up toward my chest and pushed the head of his cock against my hole, and then he slowly guided it in. At first it hurt, but he slowly and gently pushed himself into me. After a few minutes, the pain passed and I couldn't believe how good having him inside of me felt. He began thrusting, and his curved cock (later, I jokingly called it his banana dick) just seemed to hit everything just right. He lifted my other leg up and seemed to inch further and further into me. Finally, after about a half hour I felt his cock stiffen even more and then he shot his hot load shoot into me. He thrusted a few more times as he kept shooting into me and then he stopped. He laid there still inside of me for a moment and then he pulled out and his cum dripped out of me.

We just laid in bed for awhile afterward, never getting up, never getting dressed. We just laid naked until the urge overtook him and we fucked again. And again. And again.

We fucked four or five times that night, and as I ended up staying the night, twice the next morning. Our friendship had changed that day, but in a lot of ways it stayed the same. We still did just about everything together, and now we had added another aspect to our friendship.

[lnidas6699]

I messed around with a lot of guys when I was a kid. But went all the way with only one. He was staying over at my house and we got all horny like always. Then we just took it to that next step. I remember thinking, wow, this feels soo good. It felt way better than having my dick sucked. He couldnt control himswlf and then just gave it to me. It was awesome, we had one of those relstionships that we could just get up the next morning and act like nothing happened. Oh, i would love to have something like that again.

[eirepiper]

Hi...Newbie here -just had my first anal experience and can't stop thinking about it! Was Brilliant, although the bloke was rather big. We'd been messing around together at a bookstore and all of a sudden, I just had to have his cock in me. I'm basically straight, but it was all I could think about. It kind of hurt at first, so I told him to go easy. He was really cool and in a few minutes, I wanted to try again and I just squeezed and pushed back on him and it was like I was born whore.....lol
I can't wait to do it again (guess I'm "gayer" than I thought, eh?...s)
Well.....thanks for looking. Just getting excited reliving it by writing about it.
Cheers
Seamus

[BiPaoulo69]

Very nice story, I really enjoyed reading it. I wish it could happen to me.


My wife and I have been in the Hotwife lifestyle for about 7 years or so. She has a lover from time to time but I don't play with other women, and sometimes it feels like I'm slowly becoming a Cuckold but that's another story :). My first time being fucked by another guy was last year. My wife's lover came to stay with us for a weekend and they took over our bedroom and fucked all of Friday night and most of Saturday. We all got into the booze and my wife ended up having a little too much and fell asleep after being laid by him and we didn't want to wake her up for awhile. He came down into the kitchen wearing my wife's house coat which was funny and I ribbed him about looking so sexy lol. He said "ok now it's your turn", he took it off and said you wear it so I can see what it looks like on you. I started to put it on over my t-shirt and joggers and he said "no no, you have to be naked underneath like I was".

So I laughed and undressed and as I was stepping out of my joggers I had to bend over a bit and he commented "Holy shit dude, you have a really hot ass and don't take that as a gay thing, I mean you do have a hot ass for a guy". I laughed again and said "yeah Cathy tells me the same thing". Now by this time we both were pretty loaded up with booze and neither of us had much inhibitions. He said "look, I'm still horny as hell and Cathy is useless for awhile, would you consider letting me fuck your hot ass?" I laughed and said "yeah whatever"! He said again "no really, I'm not gay and I'm sure you aren't either but hey it's just sex and you're providing me a hole to fuck and I promise I'll go easy like I did when I fucked Cathy in the ass (which she would never let me do lol). After some constant prodding by him and a few more drinks I said "ok what the hell, lets do it".

He smiled and ran upstairs and soon returned with a bottle of lube. I asked him "where's the condom?" He said "now where the hell am I going to get one of those? I've been fucking your wife without one for almost a year and she didn't get anything from me and obviously I didn't get anything from her so it's pretty obvious we're not going to get anything from each other right?" I thought about it and said "yeah I guess you're right". Again he smiled but this time it was a really seedy look like he conquered this battle lol. He got me to lie on the table then put my knees up by my chest. Then he squirted lots of lube on my hole and proceeded to slowly work his fingers in one at a time until he got three into me which took some time and I started to enjoy it instead of the pain that it started with. Then he squirted a bit into my hole then squirted a bunch of it onto his cock and spread it well with his hand. I was nervous as he put the head of his large cock (much bigger than me which is why he's fucking my wife and I'm not lol) up to my hole and started to work it in. He was very gentle about it and there wasn't much discomfort. After he got his cock in about 3/4 of the way he said "are you ok?" and I said "yes it feels good". He said ok and started to fuck me harder and deeper.

Within about 5 minutes he was lying almost on top of me and had me pulled out so my ass was out over the table edge and he was supporting me. He began fucking me very hard and I could feel and hear his balls slapping against my cheeks. He started sucking and biting at my nipples the way he always does as he's fucking my wife and fucked me like he owned me and I have to admit at this point I didn't mind being owned lol. After about 15 or twenty minutes he started breathing really hard and said "I'm going to cum, can I cum inside of you"? At this time it felt so dammed good being fucked like a woman that I heard myself say "Yes yes, breed me like you do my wife" and thought to myself was that me that just said that? Now he was slamming into my ass real hard and I swear I could feel his cock get even bigger and I soon felt his cock throbbing as he was pumping me full of his sperm. When he was done he slowly pulled out and said "fuck man, you should rent out that pussy, it's amazingly tight" and laughed. I laughed as well and said "it should be, you're the first one in there". When he was completely out I could feel his cum running out of me (which was surprising considering how much of it he had pumped into my wife over the last day and a half) and it was then that I realized what it felt like for a woman when cum runs out of her pussy. When he started walking over to the counter to pick up his beer the first thing I saw in the doorway was my wife with a big smile on her face.

I was shocked and didn't know what to say. She started clapping her hands which made him turn to look and started laughing when he realized she saw what happened. She said "well now, that's perfect. You finally found a way to be useful at sex besides your mouth that is (I'm good at licking pussy lol). She looked at him and said "was his pussy tight?", he laughed and said "yes it was really tight but not as nice as yours babe". She smiled and said "well I guess you'll be fucking us both from now on". I was a little shocked and said "no I don't think so". She smiled and said "yes I think so and if you don't agree to it then I'm going to tell all your buddies about my lover and about how he fucked you and how much you enjoyed it".

All I could say was " shit, yeah ok fine". He patted me on the shoulder and said "don't worry, it's just between us and we'll all enjoy it". I felt a bit better when he said that, until he said "and oh yeah, when I fuck you you're going to wear Cathy's panties for me to take off". I knew I was screwed more ways than one right there and then lol. But to finish this off, I really do enjoy being fucked hard and deep by him and wouldn't think of stopping now lol. And yes I do love to look at pussy and wish my cocklet was big enough to satisfy my wife or another woman, and I would never kiss men and never look at men wanting to have sex with them. So I'm a forced bi and enjoying it :)

[Fzmr9t]

My 1St time was fantastic he was a newbie like me and took his time and he wasn't overly large. Once I got over the initial pain ( he did use Lube but I was still very tight) I loved it. That was about 6-7 years ago. My 2nd time was just this week and it was almost like my 1st time all over again Looking forward to my NEXT time with him

[mrcumsalot]

My first few experiences with being ass fucked were actually quite horrible. I was 14 at the time. The two males were a few years older but just as inexperienced and entered me without the aid of any lube at all. They made it inside but the pain was horrible from start to finish. Eventually ( I think around the fourth or fifth time) they used butter as a lube. Not ideal I suppose but much better than entering me dry. I learned to love being fucked and invite it frequently.

[Icebreaker]

My first time was with my best friend, we were both 14, he had a really nice cock, sort of flat and wide instead of round. At break we stayed at his brother's apartment but his brother was away most of the time (both days and nights). One night we just happened to look out the window and there was this girl undressing and since we were higher we could see pretty much everything. Since my bed was close to the window he came over to my bed and as I was on my tummy on the bed he laid right on top of me. Soon he stared to take my jammies off and I could feel he was getting excited and really wet (we were like 14-15 at the time), I could feel his head right on my hole. I started squirming and thinking he was just leaving it there, although it felt quite good. Next thing I know it slipped inside me and gosh what a feeling! He came in me and we flip flopped that night. We did it one more time after that and I left the school. I have never seen him since. I would have loved to see him again though.

[friskyous]

It was fucking amazing! It happened just today with a guy I met some time back. We started sucking and stroking each other then he fingered my asshole as he sucked me. His cock was as long as mine but nearly twice as thick. He pulled my favorite white bikini panties down and slid that big cock inside me and fucked me well. I absolutely loved it... then he ended my pulling out of me. removing the condom and cumming on my tender asshole. On my request he rubbed it up and down my crack with his cock.

[sysper]

glad u finally got to experiance it & u had a goodtime :)

[madtownbluesman]

About 4 years ago i called a friend who i have had sucking encounters with in the past and since i travel frequently i was able to visit Dallas where he now resides with his wife. I had told him i was ready to try and bottom which is something he has always wanted to do to me. So once i arrived i called him and game him my location and room number. We met downstairs and decided to have a beer at the bar before heading to my next adventure. Before leaving home i had given myself an enema to ensure i was nice and clean. Once in the room it wasn't long before i was on my knees sucking his cock, before long we were naked and 69ing and as we played he was fingering my ass. He would take the head of his dick and rub it on my tight little hole and he reached for the lube that i had brought along. I wasn't a total virgin because i had played with some dildos back home. The only way his 8 inch fat cock was going in was to get on top of him and ease it in myself. Once in it felt wonderful and i was riding it very hard. I pulled off of him and got on my back so i could watch him thrust me hard. He entered me again and the way he moved made me cum all over my chest and he took his fingers and scooped up some cum and fed it to me. It wasn't long before his intense pounding resulted in my ass being filled with hot cum and feeling his cock throbbing as it unloaded made me hard again. For me my 1st real cock was truly something i enjoyed.

[mr.beaver]

Help me get my first cock and I will tell you everything about my experience. You want to be my first. How big is your cock?

[madwolf]

So...how old were you? How did it feel like? Did it happen before or after you started having sex with women and if it happened before, did it affect your attraction to women? I wanna do it..just not sure if I should before I start messing around with girls( which might as well happen in a few days, I'm trying to get one). I know a guy, pretty nice one who will top me...I just gotta let it happen...so any thoughts on it will be appreciated...thanks!!!
it was before my first girl by 2 years. i was 11 he was 15 i started it. i am the one that wanted it. and i loved it. we tired but he couldnt get it in then we found some hand lotion and he was balls deep in me in less than a minute. it was great

[jimisbi]

It was the most wonderful feeling ever. He took his time and entered me slowly. When he was all the way in he let me get used to him before he started fucking me. Then when he started stroking in and out of me it felt so good that I didn't want him to stop. After several minutes he finally gave me his nice, hot load. From that time on I knew that I wanted to get fucked as much as possible. The only downside to my first time was that the guy fucked me only once. I would have liked for him to me at least a second time.

[Christopher South]

Mine was pretty nice.

About three weeks before I had met this guy for the first m2m sex that I ever had. We exchanged oral and mutual masturbation. He called three weeks later asking if we could get together again so I arranged to go over to his place.

We spent about 30 minutes in bed kissing, sucking each other, fondling and then I asked if he'd be willing to fuck me. He said OK, but I could tell it wasn't his thing but he obliged. While he put on a condom I lubed myself up. He got behind me, fingered me for a minute or so and then slid in. His cock was only 4.5 inches so it didn't hurt at all. He started gently fucking me and at some point in time I looked between my legs and saw a constant stream of pre-cum flowing out of my cock. I felt great. He kept going and about 10 minutes later he came.

He pulled out and lay o the bed. I cuddled next to him while he jerked me off and then we both slept for about 30 minutes before I had to leave.

[T208HUNG]

I was 17 and my step brother was 15 and we often watched porn at night and jerked off together. One night he begged to suck my cock he informed me that he had sucked alot of dick and was an expert dick sucker, he promised it would be the best head I ever had. I said ok suck it Bro and he opened his mouth and swallowed my cock whole. He was AMAZING. After that it was on I'd go down on him but mostly he had my dick in his mouth alot. Eventually we fucked each other which was ok. But being as we where brothers it was a relationship that continued until he was around 20. He was the only male I felt ok being with. We both always had GF, but brotherly love was where the hot sex was.

[pjhousbi]

First time was with a guy I had met online and had a few encounters with prior. We were mainly into sucking and jacking off. One time we were playing with sex dice, altering the actions a bit, things got real hot as we were rimming and fingering. Me mostly on the receiving end. I couldn't resist anymore and asked him to take me. He took his time. It never hurt and felt fantastic. I still gladly give up my ass to him whenever he wants.

[rbill761]

I was around 30 years old and well after I started having sex with women and in no way has it affected my attraction to women . But we are all different young man only you will know when you do it. I started sucking cock way before this and love it as well as getting fucked in the ass. If you want to do it go for it I did and loved it if you or the guy that's going to fuck you jacks you off you are going to cum very very damn hard. As far as the girl is concerned go for it

[phoseguy]

I was 15 he was 17. It was the same guy who I gave my 1st blowjob to. He asked me if I ever thought about getting fucked and I had to be honest and told him that I had. In fact I had been using the shaft of a putter to fuck my ass and really liked it. He asked if he could fuck me. I told him yes, was nervous as all hell but wanted it bad. We were already naked....he went and grabbed some lube and rubbed it on my hole and his cock. I laid on my back legs spread wide and he put his hard cock to my hole. He eased it in and when it poked inside me my god did it feel good! He eased it deeper...it hurt a bit but felt great. He started to pump me slowly and it didnt take long before he was in me deep. I love feeling him pumping me. It only took a little while before I could tell he was ready to cum. He pushed it deep, held it there and filled my ass....what a feeling!!!! After he filled me he pulled out and gave me the one and only blowjob he ever gave me. I guess he thought he should reward me. Little did he know his cock and cum in my ass is all I needed!

[bi.kenner50]

I was 53. I didn't accept my liking of gus until I ditched the Christian myth. It didn't hurt a bit and was great!

[ghw132]

It was fantastic. I was fourteen and he was 15. The moment he touched my penis i knew i was going to like it. He used baby oil to lube me and himself. I straddled him, facing him. He came really quick. Then masturbated me until i came.

[trackerone]

it was , wow, had been doing oral with this guy for some time , he had wanted me to let him have my ass a long time, but i thought he would hurt me , he was over 8in and thick , but could stay hard for a long time ,, he said he will not hurt , and will start real slow ,and open me up with a small dildo to get me used to it ,, he was right ,, when it got to the real cock going in me it was so easy , and the deeper he was the better it felt , i don t know why i waited so long , he made it feel so good

[a2smith09]

it was , wow, had been doing oral with this guy for some time , he had wanted me to let him have my ass a long time, but i thought he would hurt me , he was over 8in and thick , but could stay hard for a long time ,, he said he will not hurt , and will start real slow ,and open me up with a small dildo to get me used to it ,, he was right ,, when it got to the real cock going in me it was so easy , and the deeper he was the better it felt , i don t know why i waited so long , he made it feel so good

Yeah when done right it is amazing. Luckily my first was a very experienced ass maestro.

[walt0057]

I was 9 my uncle wanted to see how sensitive I was slid right in would cum multiple times, and he would share me sometimes.

[hung4you]

My 1st anal experience was when I was in collage in Mpls. My room mate was very Bi and back then I was straight, had a girl friend which I married 32 yrs ago and still married. Over Christmas break 2 weeks prior I was introduced to cock and cum, and once I did I had to have more. Fast forward a few months to spring break, not having much money he and I decided to stay in Mpls during break. During that time between Christmas break and spring break my room mate and I enjoyed many a night pleasing each other’s dicks.

Anyhow, he had often talked about anal and I was nervous as I thought it was dirty and painful. So one night drinking and watching porn he convinced me to try it, he taught me how to properly prepare for anal via enema and lots of lube. We spent the afternoon getting me clean and after we showered, the fireworks happened. I could not have found a better teacher, he was gentle and mindful of my apprehension but I let go and let it happen. After the initial shock of him trying to put his big cock in my ass he slid it in ever so slowly and to my surprise once in and stretched h felt awesome. He worked it like a pro and had me so relaxed that I cummed hard and shot a massive load all over my chest and face. Fucking me missionary I remember grabbing his ass cheeks and forcing him deeper which excited him to no end and he whispered I’m going to cum, his hard cock stopped moving and all I felt was his cock pulsating and him moaning. After cumming he just let it sit in me for a couple of minutes taking it all in. When he pulled out I felt his cum gushing out of me and grabbed the poloroid camera and took a picture of his cum evacuating my ass. So with all my cum on my chest and face and his cum leaking from my well fucked virgin ass I was a cum soaked mess. After taking the picture he gentle went down and licked my still semi hard cock and licked and cleaned my cum off my cock.

He smiled and said so what did you think about that? I was somewhat speechless but satisfied all at the same time. I told him we can never show that picture or tell anyone , not ever . So after 34 years we still get together once a year for an anal reunion.

[a2smith09]

I was 9 my uncle wanted to see how sensitive I was slid right in would cum multiple times, and he would share me sometimes. Yeah my ass loved getting fucked and I could cum too from anal. It's addicting

[a2smith09]

My 1st anal experience was when I was in collage in Mpls. My room mate was very Bi and back then I was straight, had a girl friend which I married 32 yrs ago and still married. Over Christmas break 2 weeks prior I was introduced to cock and cum, and once I did I had to have more. Fast forward a few months to spring break, not having much money he and I decided to stay in Mpls during break. During that time between Christmas break and spring break my room mate and I enjoyed many a night pleasing each other’s dicks.

Anyhow, he had often talked about anal and I was nervous as I thought it was dirty and painful. So one night drinking and watching porn he convinced me to try it, he taught me how to properly prepare for anal via enema and lots of lube. We spent the afternoon getting me clean and after we showered, the fireworks happened. I could not have found a better teacher, he was gentle and mindful of my apprehension but I let go and let it happen. After the initial shock of him trying to put his big cock in my ass he slid it in ever so slowly and to my surprise once in and stretched h felt awesome. He worked it like a pro and had me so relaxed that I cummed hard and shot a massive load all over my chest and face. Fucking me missionary I remember grabbing his ass cheeks and forcing him deeper which excited him to no end and he whispered I’m going to cum, his hard cock stopped moving and all I felt was his cock pulsating and him moaning. After cumming he just let it sit in me for a couple of minutes taking it all in. When he pulled out I felt his cum gushing out of me and grabbed the poloroid camera and took a picture of his cum evacuating my ass. So with all my cum on my chest and face and his cum leaking from my well fucked virgin ass I was a cum soaked mess. After taking the picture he gentle went down and licked my still semi hard cock and licked and cleaned my cum off my cock.

He smiled and said so what did you think about that? I was somewhat speechless but satisfied all at the same time. I told him we can never show that picture or tell anyone , not ever . So after 34 years we still get together once a year for an anal reunion.

Oh man how wonderful for a first. I did that with a lot of my friends too, they seemed to like it as well.

[querty]

My first time taking a cock was incredibly painful, and incredibly erotic.

I was in a Bi MMF threesome, and we had been having amazing sex in everyway you can imagine for hours, except anal for he and I. I had always fantasized about getting fucked. We were actually all done for the night having another drink when conversation tuned to 'the next level' of Bi play (this was very early on in his and mine Bi experiences) of course Anal came up, and I said I wanted to try it. The conversation made us all three horny again, and she was encouraging us to go for it. He and I were both rock hard again, so off came the clothes. I moved to the floor with my body on the couch, and he got behind me. Neither he nor I had any clue what we were doing and even with a ton of lube is hurt like crazy, but I wanted that cock in my ass. I was breathlessly saying things like, "omg that hurts, holy fuck, holy fuck, I want your cock in me, keep going, keep going" She was right next to me whispering things "take it, baby, take his cock, you know you want that cock in you"..... Finally he was inside me and it still hurt like mad but the moment was amazingly erotic. We didn't go long because it hurt to much. The next time was better because we were prepared and not in a hurry, and the next time better, etc.

PS> My favorite position is lying on my back on the edge of the bed with my legs over the guys shoulders.

[bi.kenner50]

I guess I should give a little more detail. When he started fucking me I began to feel the horniest I ever have been, so I began stroking myself. It felt like nothing I had felt before! When I came it was the greatest orgasm I had ever had!

[a2smith09]

I guess I should give a little more detail. When he started fucking me I began to feel the horniest I ever have been, so I began stroking myself. It felt like nothing I had felt before! When I came it was the greatest orgasm I had ever had!
Lol that is fairly common! Glad you enjoyed it!

[Avalokita]

I was 32-ish, newly-divorced, depressed and "self-medicating", as they say. Tequila and nose candy *will* lift your spirits, but it also made me as horny as a bull in Springtime. I always had the masturbatory habit of stuffing appropriately-shaped objects up my butt (well, at least since I was about 15, or so), but had never had even the imaginings of being with another guy.

Remember the tequila and go-fast? Yeah....it makes you creative. Very, VERY CREATIVE. And that creativity suddenly extended itself to my body. As soon as the disso was finalized, I pierced both my nipples, and my penis, and was loving my hand several times a day--waiting for the piercings to heal--and, once they did, every woman I knew, who didn't know my ex, was on the menu.

After fucking myself silly for about a year, I happened to move away from the area my ex lived in, and the sex dried-up. I was in an area that I had lived in twenty-odd years earlier, but literally knew nobody there. Since I'm not the bar and nightclub type of guy, I hit a few of the local ABSses and noticed the "lifestyle mags and personals rags" on the magazine stand (people actually read words on paper, back then).

All of the womens adverts were gals pretty-much looking for long term relationships, or demanded too much time invested in going out, and all of that. I happened to notice an advert by a guy, about 15 miles away from me, who stated that he was only interested in sucking guys off. I forgot about it until work took me into his town, on an evening call. When I was done with work, I hit a pay phone (Remember those?) and called him up. As chance would have it, he was available and accepting visitors.

I found his place (dark, isolated cul-de-sac) and just walked in through the front door (per his specific instructions) to find about 8 guys, naked, and sitting around the living room, with one guy leaning into the lap of one guy, who was leaning back on the sofa, getting sucked-off vigorously. Fascinated, I took off my clothes, and joined the other naked guys in the "action area", and watched everybody masturbating, while our host moved from hard penis to hard penis.

When my turn came, I blew a huge load, and quite loudly. As things wound-down, and guys got dressed to trickle out the front door, back to their cars, there was some low conversation going on between some of the guys, and I joined the murmur of "Hi, how are ya?s", "What's your name?", "You live around here?", and "What are you into?" I made the acquaintance of one guy who I had noticed had an unusually large penis (as thick as my favorite dildo, but not quite as long) who said that he came by every Thursday night, at 8, if I was interested in getting into some "more interesting things" in the future. He kept telling me that he liked my ass and would love to play with it. I said that I'd think about it, and hauled ass home.

Two weeks later, I showed-up on a Thursday evening, at 8:00 on the dot. The guy who had chatted me up was walking in from his car. At the door, he popped my belt buckle loose, and shoved his hand down the back of my jeans, grabbing my buns and squeezing. Following me into the house, with his hand still down my pants, he said something to the homeowner. Our host went into another room--completely naked--and brought in a cheap-looking coffee table and set it in the middle of the livingroom floor. As I was a little occupied with this guy shoving a finger up into my ass, while trying to get undressed, I really didn't notice much about the table.

Justin (the homeowner) laughingly said that the guy who was finger-fucking my hole had found his lay for tonight; and somebody voiced approval from the kitchen.

As the speaker brought in bottles of beer from the kitchen, I dropped the last of my clothes on the end table. He only said, "Hi! Nice ass!" and handed me a beer, as Justin told me to lay, face down, on the coffee table. It was then that I noticed that the coffee table was padded on the top surface, and had a hole cut into it to allow a person's penis to dangle through, if their head was at the right end of the table. As I did so, Justin plugged a cord in, that was attached to the table, and small halogen spot lamps, under the table, turned-on. Justin then plugged a cord into his entertainment center, and switched several devices on. As the big screen TV warmed up, and the picture bloomed for us all to see, there was my penis dangling through the hole in the table--as seen from underneath.

Other guys had been arriving during this time, getting naked, grabbing a beer, and sitting all over the room--usually smacking my ass on the way to wherever they had chosen to sit. Suffice it to say that, I was the evenings first butt-fuckee subject, and everything (minus faces) was being video-taped. This made me feel both uncomfortable and turned-on an just a bit slutty.

The table faced the TV, and I watched as Justin slid under the table, face up, and started sucking on my penis. One by one, some of the guys got up, and dipped a finger into a bowl on the actual livingroom coffee table, then stuck that finger between my buns. It was something like KY in the bowl, and several of the guys took it upon themselves to finger fuck me a bit--some of them quite deeply. It felt good, in all honesty.

I noticed that mine wasn't the only asshole being lubed-up, as the guys were lubing-up each other's holes, and stroking each other's cocks. Justin hollered around my penis in his mouth, for the guys to get towels to sit on, instead of getting his furniture all slicked-up with lube. By that time, my attention was focusing-in on the mouth on my penis, and the image on the TV of Justin sucking me quite expertly.

I heard the snap of latex behind me, and looked around to see the guy (I never did remember his name, though he did tell me twice) pulling a condom onto his well-lubed penis, while holding a syringe in his teeth (No needle!). He poked the syringe into my lubed hole, and pushed the plunger all the way down. (I later learned that he had pushed 10ccs of lube up inside me.) He stood over my ass, and smeared the condom with lube, and lowered his erection between my buns, pressing at my opening. I unclenched (from holding the lube inside my anus) and let him slide into me. "All the way." I told him, and he pushed steadily, spreading my ass cheeks as wide as they would part, until I could feel that he was all the way inside my ass, with his balls pressing against my perineum.

He, along with everybody else watching us, expressed amazement that I could take him in a single steady push. I said something about this being my first cock, but having practiced for years with dildos. He pulled all the way out, and sunk his erection back into my ass faster and harder. It felt good, especially with Justin sucking me to beat the band. Justin pulled my own erection out of his mouth, and told somebody to get me whatever I wanted to drink. Four fingers of tequila showed up in a highball glass, and I killed it in one swallow--spilling just a bit down my chin, into my beard.

I was in heaven. I laid there, listening to my ass getting pounded, watching my penis get sucked, and listening to the other guys in the room--some masturbating, others masturbating somebody else, and still others sucking the penis closest to them.

When I finally had my orgasm, I had a violent, protracted, very loud orgasm, with my ass squeezing the penis that was fucking my ass. Justin kept sucking me after my orgasm, and drew-out my spurtings and cumming for more than a minute; and my ass was milking the penis of the guy fucking me the entire time. As I coasted-down from my orgasm(s), and laid my head down on the table, I could feel my top's penis start to pulse, and I heard him moan as he started pounding my ass fast, hard, and as deep as he could reach inside me.

That was my introduction to having my ass fucked, and that evening lasted until about 03:00 AM the next morning; during which time, I watched guys fucking each other while Justin claimed their cum from underneath his "special table". Later, I saw Justin carrying shot glasses from underneath the table, to the kitchen. It seems that he was sucking us dry, letting us cum in his mouth, then spitting out our loads into the shot glasses. Right about then, somebody asked me if I wanted to see the video of me having my ass invaded. There was a second video camera recording the anal intercourse on the table--all night long.

I had to admit that I did enjoy seeing on video what I only felt from behind, and inside, me. Several of us sat on the floor, and masturbated each other while watching me being fucked by the biggest penis in the group.

I'm pretty sure that I had close to 8 spurting orgasms that night, before I emptied my prostate completely.

I've never had that level of interaction with other guys, since then; but would jump at the opportunity to do it again, if I could.

[DareMe]

Hot story.

[Neonaught]

Sorry I have not been on since Wednesday. I was wrong about my new friend coming back Sunday morning. He came back to my house Saturday morning and he just left. He came in to my house Saturday at 11:00am. He was ready for more. He took me to my bedroom, dropped his clothes and I was shock that his cock was so hard. He told me he could not wait for 24 hours to get at me. I carried me to my bed and gently laid me down. He got on top of me and feed me his cock in my mouth. I stopped gagging and just loved the feel of it going down my throat. He was so careful to give me air. I lost count of the number of times he came, but the cum was backing up my throat.
He pulled out, then he lubed my ass with cum erupting from his cock. I became afraid that I could not handle his thick cock in my ass, but he worked the cum in my ass with his large fingers. I must have relaxed at that point, cause he slipped three of his fingers in with ease.
At this point I began to moan uncontrollably . He turned me on my stomach and got on top of me. With my ass in the air he slid his cock into my ass. He went deep, far deeper than on Wednesday. He came again then he went to work . He fucked me like a wild man. I came like I never had in my life. He fucked me for about three
hours straight. He kissed me on my neck, then I went to sleep. I was exhausted.
He must have continued to fuck me in my sleep. I have never seen so much cum in my life.
I woke up about seven in the afternoon and he was sitting on the bed smiling at me. We talked for about an hour and I confessed at this point he owned me. He had some chilled wine in a glass and I drank a whole glass. This man is enormous in size, so muscular. He had ran a warm bath for me and he picked me up an took me to my tub. I was so weak. He bathed me, he lifted me out of the tub then dried me off.
Then he laid back on my bed, he had put clean sheets on the bed, I was in heaven. He brought me a lite dinner which he fixed while I was sleeping. We drank more wine.. At around nine last night we went back at it. The thing I don't understand is that my ass was not sore. He was so considerate. I don't know what time I went to sleep, but the last thing I remember is that he laid me on my side and fucked me all night. To be the first man to ever do this to me, it felt so natural. At nine this morning he woke me with breakfast in bed, He had coffee and bacon and eggs. He was fully dressed and told me to stay in bed and that he had to go home.
Then he did the most amazing thing. He told me that I had the finest ass he had ever had. He also said he would never go back to fucking a woman and that he would be back at my house, this Friday night. As he left I told him that I truly loved him. He replied, "James, I know."
All this is insane to read, but it is absolutely true.

What a wonderful experience!

[allanscott]

My first time hurt like hell. Took me a long time to try it again The next time was an older man he took his time really got me hot O my God I felt fantastic everything about it was great I even kcame from him fucking me

[69luvr]

a pain in the butt but I loved it!

[xp243]

My first time I was at a bar and got a phone number off the bathroom wall for a blowjob i Was drunk and called it and went to his place where he gave me a beer and he took off my pants and started blowing me next thing I know we went to his bedroom where he continued blowing me and then started licking my balls then something I never felt he was licking my crotch and my ass all while he was jerking me off. It felt amazing I was so worked then he stuck his cock in me and came and I was like wow what are doing. He was finished so I finished by jerking off. That was the only time I got fucked wish I wasn't drunk so could remember it better. I want to try it again.

[ChiefH]

My first and only time came when I was 14 and he was 13!!! He was a school friend and he had a beautiful 8.5" uncut cock!! We had been exploring our sexual feeling for about 2 years before this night happened!! He had docked my cut cock 3 or 4 times before!! This night It went even farther when I pulled out the Vaseline and smeared on my asshole!!! He gently slid his cock in me and moved in and out so very slow until I was looser!! With each push of his cock against my prostrate felt wonderful my cock was as hard as a rock and I haven't even touched it!!! This was also my first hands free orgasm!! It was a night of firsts for me and him!! But our lives changed and we both got girlfriends and married!! Would love to have him fuck me one more time!!

[DMercator]

Man this site needs a like button for some of these replies. My first time I was 50. He was older, more experienced and just good at taking the lead. He had a high 4 poster bed. He stood on the floor, put my legs over his shoulders and slowly worked his way in. I don't know if it was because he was well lubed and the fact that he wasn't overly thick, but after some initial discomfort it felt wonderful. When he finally came in my ass I shot a load all over my stomach and chest. I had no idea it would be so damn good.

[Godownonit]

I was about 16, he was 20 - something. I did not much like it, at the time. I am still not that into getting fucked, even now. I prefer oral.

[Eros35201]

I was 50, was difficult because I was so tight. Still tight and wanting it again.

[BisexualPisces3192]

It was awesome!!, I would love to do it every morning after waking up and ever night before going to bed.

[notquitewt]

4 months ago at 50yo was my first. I loved feeling him in my pounding away. Need it again lol

[Shefford]

Last week I was fucked for the first time at my local ABS. I'm a 62 year old "straight Man" who for the last two years has turned into a cock sucker having never done anything like this in the past . I'm married have children and grand kids but once I tried cock sucking on an urge I cant stop , I'm addicted. I met this guy a while back he seems to be in my age group which most guys in this place are middle aged married man. I'm big height and weight and he loves big men so every time he sees me we hang out. He is average size but has a very nice thick cock. We've sucked each other off and I mentioned his cock would be perfect to fuck (I've been thinking about it). He loves rimming my ass so one day he bends me over and says give me that ass . He starts fingering me and I'm thinking he's going to rim me when I feel the head of his cock opening my ass. I couldn't believe it. initially it burned a little but after a few strokes he was in and I couldn't believe the feeling. After a few minutes I was pushing back on him. He just gave me a taste , he didn't cum but I can't wait to continue.

[Fzmr9t]

Last week I was fucked for the first time at my local ABS. I'm a 62 year old "straight Man" who for the last two years has turned into a cock sucker having never done anything like this in the past . I'm married have children and grand kids but once I tried cock sucking on an urge I cant stop , I'm addicted. I met this guy a while back he seems to be in my age group which most guys in this place are middle aged married man. I'm big height and weight and he loves big men so every time he sees me we hang out. He is average size but has a very nice thick cock. We've sucked each other off and I mentioned his cock would be perfect to fuck (I've been thinking about it). He loves rimming my ass so one day he bends me over and says give me that ass . He starts fingering me and I'm thinking he's going to rim me when I feel the head of his cock opening my ass. I couldn't believe it. initially it burned a little but after a few strokes he was in and I couldn't believe the feeling. After a few minutes I was pushing back on him. He just gave me a taste , he didn't cum but I can't wait to continue.

its scary how addicting it is! I tried it once and was hooked! Married w a grown child here and didn’t even think this way until i was in my mid 40s! Now I crave it!

[Shelby57]

I've told this before on this forum, so I'll just give the shot version. Just a few years ago, I met a guy through a Craig's List post. We had an immediate chemistry and went back to my apartment for me to suck his cock. I had told him it would be my first time and he was honest in telling me he wasn't interested in reciprocating. I was fine with that, I was just ready to have a man in my mouth. After I sucked him for a while, he told me that he sometimes had trouble cumming from oral and even though it was not what we talked about, wanted to know if he could fuck me. I told him I had played with toys in the past and had enjoyed and I would let him try. I had actually given myself an enema hoping that it might happen. I put a condom on him and lubed his cock. and then my ass. He spread my legs and entered me very slowly. Once inside, he asked if I was OK. I told him yes and that it felt really good. He started to fuck me , slowly at first and then harder and harder. I just got more and more excited at the pleasure. About ten minutes in, he pulled out and told me the condom had broken. I told him I didn't care, just don't stop fucking me. He took the ruined condom off his cock and went back inside me; fucking me for another fifteen minutes before he exploded inside me. I could feel his cum in my ass and wanted more. He laid down next to me and I took his cock back in my mouth and sucked and licked it for a while hoping he would get hard again and we could have round two before he got up and left. It was possibly the most exquisite sex I have ever had. We met one more time and didn't even pretend. I sucked him long enough to get him good and hard, lubed up his cock and my ass and he fucked me for about 20 minutes, cumming inside me. I was hoping I could be his fuck toy but he never called again.

[Bottomboy1974]

I was 13 the first time anal sex it andwas with a family member but i was so addicted to it after that, I love the feeling of a nice size dick in me andno I still love girls and get rock hard I just love dick also...

[Twowheelfun]

It was 11 years ago with someone I met off Craigslist. I went to his house and we went upstairs to his bedroom . We started off with a 69 . He came kinda quick but he kept sucking me and finger fucking me . After 10 minutes he was putting me on my back and asking me condom or bare . I said condom and he put one on and slid his 9 inch cock up my hole . I thought it would hurt but damn it felt good . He fucked me in numerous positions for about an hour till he came . I loved every second of it as my cock was hard the whole time . I would give anything to get fucked like that again . Every guy I met since claims to have at least 5 inches but it seems more like 3-4 when I pull their cock out .dont get me wrong,I like the feel of their cocks in my ass but good lord that bic cock spoiled me

[Twowheelfun]

The last time was in July . He was smaller than he said but he made up for it the way he devoured my cock and ate my ass . I got on my knees and told him to fuck me . He was new and just tried to ram it home . I told him to stop and when he did I told him to lube his fingers and slowly finger fuck me . He did as I told him and while he fingered me I stroked my cock slowly . After a few minutes I lubed his cock,bent over and told him to fuck my ass . After a few minutes he pulled out got on his knees and said " do me" .i lubed a few fingers and played with his ass while I stroked my cock. After a few I slid my cock in his ass and slowly fucked him till I came . I then had him stand in front of me and sucked his cock.he loved it and so did I . I look forward to more flip fucking

[stick420]

I'm not sure how old I was. I remember I was pretty young. I was the young tag around boy.The boys were older than me. I used to play with their dicks to be in their tree forts. I was too young to know any better. One day my uncle spyed on me sucking though I didn't know..Uncle was staying with us having just seperated from his wife or so dad said..I remember him asking dad if he could take me fishing. A day I'll remember the rest of my life. He stopped at the bait store for worms and beer. In the car he opens himself a beer and hands me my very first telling me its our secret. I really didn't like it but he kept telling me to drink up. Before I got to the end I was feeling my first buzz.He haded me another. It would be a day of firsts. Funny how I remember little details. Down a dirt road along the river strone with bottles and junk people had dumped. A wooded spot with a clearing,rock ring where a campfire had once been along side the river. Everytime I look at a jar of Vaseline I remember him and that day. It wasn't pleasant he wasn't gental, he was drunk and horny,he held me down for what seemed like hours. I'll never forget the musky smell of his pubic hair while I struggled to breath gagging while he fucked my mouth holding me by my hair saying I know you like it boy I saw you sucking the boys in the woods. You're gonna do what I want or your daddy is going to know you are the neghborhood cock sucker. When he fucked me it hurt like hell. I remember laying on my back on the pine needle covered ground looking up through the tree tops at the blue skys seeing the fluffy white clouds drifting by me naked, legs spread, one on each side of his head, his hairy chest and belly on the backs of my legs,his strong grip on my waist pushing his dick in and out of me,his body weight holding me pinned against the ground, the burning pain in my butt deep within.Him grunting saying what a tight little ass I had , much tighter than his wifes,His heaving balls slapping my butt. I remember feeling sick to my stomach,the urge to poop,the trees spinning,I passed out. next thing I know he's pushing his soft dick between my lips telling me to suck it I know you know how. That was the first cum I'd ever choked on,first cum ever. I felt dusgusted on the way home, I could feel his cum running into the crotch of my underware. Him telling me as long as I keep it our secret he wouldn't tell my father what a little Fag I was. I remember wondering what a fag was I had no idea.He had nothing to worry about I was too ashamed to tell anyone..
The very next day at breakfast dad says I hear ya'll had a fun day fishing that you caught a big one. Ya'll have fun today ur mom and I are going to Nashville, your in good hands with Bobby.They weren't out of the drive far when his making me suck it. It was a long day...After he moved out I felt like a ton of stress gone. I didn't play with boys much until way later in life. Got married had two children and managed to keep my dick cravings at bay for many years..

[sysper]

in case it needs to be said.....what ur uncle did to u was absolutely wrong. this is nothting short of sexual abuse. i'm so sorry u exerianced this. it was absolutely not ur fault. on top of that he blackmailed u & let u feel u deserved this. his own brother's son too. what a piece of shit.

[steve2in]

The first time I was penetrated it was with another guys finger and I was quite young. After that, I experimented with my own finger, broom handles, and other foreign objects. Once I hit puberty and all through high school one of my friends fingered me on a regular basis as well as penetrated me with other objects. Several girlfriends, you fucked The fir me with a strap on an elitist to their vibrators. But the first time I got fucked by a guy I was 40 years old. I wish I had waited so long. At first, he did me from behind and it felt great. Something different about a living throbbing cock penetrating you for sure. After a while, he put me on my back on the couch and I held my legs up my head as he guided something. Every time he slid himself inside the I could feel the intense pressure building. Every time he slid himself inside of me I felt a little bit more of my manhood slipping away. I could feel the intense energy building throughout my entire body and then with one final thrust I felt him cum inside of me. My entire body seemed to explode and then I came like I never seen before. He would pull back and pump himself all the way back in again. Each time I would shoot more cum. After that, I couldn't get enough.

[mtfromlv]

I hate to say it, but I’m 60 and still waiting for my “First Time”... Can’t talk him into it, although he said he’d love to.

[Sexter 51]

Still waiting for first time, but toys are fun also

[LoveMyThongs]

I was 17 and had been wearing thongs for over a year and I got hit on at the beach by a guy in a rio style bikini. I had been wanting to be with a guy for a while but when he sat next to me and leaned back his bulge turned me on. When I get really turned on my ass pulses involuntarily and feels really good. This was really strong. He was 19 and lived in the dorms near the beach I was at in San Diego. I said we should check it out and we did. I walked up the trail in just my thong as I had this intense wave of sexuality and sensuality come over me. We got to his dorm and he kissed me and it felt so natural. He changed into a thong and from there it felt natural and I loved stroking his big dick. We started doggy style and I wasn’t nervous but I’d heard it hurt the first time. I was pulsing hard and as he slowly thrust it in me it didn’t hurt but felt so good like nothing is had with my girlfriend. I started moaning louder and louder because the harder and deeper he pushed the better it felt. I never told him that was my first time but we had a lot of sex. And I never told my gf. Since then it’s never hurt

[Zoom1969]

I was 23 and I was with a bud with benefits. We usually just messed around and just gave each other blowjobs or we would jerk off together. His wife was out of town one weekend and I went over to his house. We were watching a movie in his big king sized bed. We messed around for awhile after the movie was over. He hinted about penetrating me... This was something I never really thought about doing. Or felt like I wanted to try. We messed around a little more and I told him I would do it! I was scared but he was someone I felt really comfortable enough with to try this for the first time. I told him I didn't really feel prepared... He was reassuring and said everything would be fine. He started out slowly and then started going faster. He really gave me a good ass pounding! I don't think I have felt anything so pleasurable and painful at the same time! He wore a condom so he didn't ejaculate inside of me. We probably only did this a few more times over a year or so. One time he pounded me so hard that he made me cum hands free! This dude has such a huge cock! He is the only guy who has fucked me... I have never felt comfortable enough with anyone else to do it again!

[Spininmywheels]

It was simply AWESOME!!!!
I have been wanting this for several years and it just happened about two weeks ago.

I want more from him and often.

[guywholikesboth]

First time I was 13 he was 14 he had an 11 inch cock he rubbed petroleum jelly in my ass and spread my checks he then shoved his cock in to my ass hurt like hell screamed and I made him take it out. then when I was using things in my ass for years got the courage to try it again had a 18 year old fuck me for 20 min it was fun he never came . 2 week latter at the why I had a guy fuck me and he came inside me it was great wish I hadnt waited so long

[hung4you]

I can credit my collage roommate for making me the way I am, through 4 years of collage we were roommates and after our 2nd year I knew full on he was gay and I was bi, he taught me how to swallow cum, take a good ass pounding and to this day we are still close friends who play about twice a year, only because he lives so far away.

[thickneasy]

it wasnt bad or good was kind of meh, he didnt really last long once he got in.

[Warren63]

You are very lucky, I wish I had had the nerve to get my buddy to fuck me, he had a great cock, we would jerk each other off , most times I would lay there staring at it wishing he would put it in my mouth.

[Wcbranson]

When I was a teen I would hook up with a neighborhood friend all the time. We would suck each other off and I loved swallowing his load. He would never fuck me and wouldn’t let me fuck him. I think I was in my early 30’s when I finally met someone who liked topping. I met him at a hotel and we sucked each other for about an hour before he pushed me back on the bed and pulled my legs up over his shoulders. I can remember he slid on his condom, lubed up my ass and his cock and slowly slid into me. I remember it was really painful because he got in a little, strokes back and forth a couple times and then just slid all the way in. I didn’t have time to relax when he pushed in but he did hold his cock deep in my ass and let me relax. He grabbed my legs under my knees and picked them off his shoulders then spread them wide apart and started stroking in and out of my ass. I could feel him hitting what I think was my prostate over and over. It made me feel like a had to pee but still felt incredible. After a few minutes of that I could feel myself reaching orgasm. I told him I was going to cum and he pushed my legs up more, got up above me and slowly pile drove his cock into me. I didn’t realize that he was positioning me to cum all over my own face and once I did I could feel his cock start throbbing in my ass and then he lowered me down and sucked the cum from my face and neck.

I’ve has two other experiences since then with one guy but it wasn’t as good as the first time. Primarily because the second guy was huge.

I’ve also topped a guy several times and it’s an incredible feeling. I want more of both.

I had been with women many times before I was with a man, I love women, I am not interested in sensuality with men or a relationship with men, just the raw animalistic sex that comes from being with another man.

[John1971]

Really wish I could answer this question....

[willj]

It was Amazing. He was Large very large thick and long. I took it all and loved every second of him aggressively taking my virginity. He was also quite surprised I was so opened to him taking it all. He even suggested I could not be a virgin because I was so good and He really had his way with me.

[Opportunist]

I want to add my thanks to everyone for sharing their experiences. I must have jacked off four or five times as I read about your introductions to the joys of anal sex. I also have to extend my sympathies to those who were forced by adults against their will. But it does beg the question, has that first violation ruined enjoying anal sex? Do you thinks back on it or just block it out? Did it make you submissive?

While I'm curious about anal sex, an intestinal parasite, an anal fissure and an anal fistula have left me fearful of anything more than a finger up my ass.

[crazytrain]

I absolutely love it I was about 38 my first time

[Roddmann]

I don’t remember the exact first time but I’ve always loved playing with my ass. My buddy and I would jack and suck each other since we were kids. I loved having him fuck me but he said it hurt him for me to do it. He was much bigger than me, a solid 9” and thick(awesome cock). We figured out if he rode me he could take it as slow as he wanted and that let me stroke him while he did. Loved catching his load on my face and chest. Damn I miss that!

[OpenBineapple]

My first time getting fucked was amazing. There were about 15 people in the room watching us. I was fucking a chick missionary while her husband plunged his thick 8” cock in my ass. Our audience was impressed.

[dowmass]

As a bi female who has never done tha anal thing...WOW.

"Not doing the anal thing" - is that because you never had the chance, or is it because you don't prefer that?

[JeffT]

First time was a bit awkward but really liked it.

[Sundazzled]

My first time wasn’t terribly pleasant. We were both anal nubies, and really didn’t know what we were doing. I allowed my buddy, Dave, to enter me from the rear— doggie style. Despite copious amounts of Astroglide slathered on his amply sized cock, and an equally generous amount in and around my opening, he was able to penetrate only two or three inches — and it hurt like heck!

I wanted him to stop, but I was eager to fulfill Dave’s fantasy. After maybe 10 minutes of trying, he put me on my back, and I draped my knees over Dave’s shoulders. In that position, he was able to work his cock past my sphincter and eventually, a quarter-inch at a time, all the way inside me!

As he began sawing his cock in and out, his blissful expression and gentle, contented moans left little doubt he was thoroughly enjoying his first anal sex. Down below, my only sensation was a slightly uncomfortable feeling of pressure and fullness. Perhaps for Dave’s benefit, I pretended to enjoy being fucked. I wriggled my hips, urged him to “fuck me harder” and begged him to “fill me with your cum!” I even tugged sensuously at my own cock as by middle aged fuck buddy pounded away, but truthfully, I wasn’t really all that aroused, and never got more than semi-erect.

Okay, there was some satisfaction in knowing I could cross bottoming for another guy off my sexual bucket list, and I truly did enjoy feeling Dave’s cock spasming and throbbing as he orgasmed inside me. I’ll concede I was also strangely aroused by the feeling of Dave’s semen trickling out of me after he withdrew. But being fucked for the first time wasn’t quite the the fulfilling, erotic experience I’d imagined it might be. If there was any payoff, it was the unusually intense orgasm I had when Dave finally brought me off by hand.

I bottomed for Dave five or six more times that summer in a variety of different positions and I’m pleased to say our subsequent experiences were significantly more enjoyable, and that I occasionally long to explore that again.

[Sundazzled]

My first time wasn’t terribly pleasant. We were both anal nubies, and really didn’t know what we were doing. I allowed my buddy, Dave, to enter me from the rear— doggie style. Despite copious amounts of Astroglide slathered on his amply sized cock, and an equally generous amount in and around my opening, he was able to penetrate only two or three inches — and it hurt like heck!

I wanted him to stop, but I was eager to fulfill Dave’s fantasy. After maybe 10 minutes of trying, he put me on my back, and I draped my knees over Dave’s shoulders. In that position, he was able to work his cock past my sphincter and eventually, a quarter-inch at a time, all the way inside me!

As he began sawing his cock in and out, his blissful expression and gentle, contented moans left little doubt he was thoroughly enjoying his first anal sex. Down below, my only sensation was a slightly uncomfortable feeling of pressure and fullness. Perhaps for Dave’s benefit, I pretended to enjoy being fucked. I wriggled my hips, urged him to “fuck me harder” and begged him to “fill me with your cum!” I even tugged sensuously at my own cock as by middle aged fuck buddy pounded away, but truthfully, I wasn’t really all that aroused, and never got more than semi-erect.

Okay, there was some satisfaction in knowing I could cross bottoming for another guy off my sexual bucket list, and I truly did enjoy feeling Dave’s cock spasming and throbbing as he orgasmed inside me. I’ll concede I was also strangely aroused by the feeling of Dave’s semen trickling out of me after he withdrew. But being fucked for the first time wasn’t quite the the fulfilling, erotic experience I’d imagined it might be. If there was any payoff, it was the unusually intense orgasm I had when Dave finally brought me off by hand.

I bottomed for Dave five or six more times that summer in a variety of different positions and I’m pleased to say our subsequent experiences were significantly more enjoyable, and that I occasionally long to explore that again.

[oldoralman]

The first time I received anal was absolutely fantastic. It felt so good. My wife had used a dildo on my ass a few times and also the guy's cock was well lubed as was myasshole.

[gotoguy]

I was 48 when i had the courage to reply to a CL ad, and went to his house and right away he could tell i was nervous. so we had a couple of shots and he helped undress me while he kept his T-shirt and sweatpants on, and me in my birthday suit. He only had intentions of giving me oral as we planned. He sat me on his couch while he knelt and i was like this is it!! he would suck me for 10 minutes at a time then would slap his forehead with my dick and it made me laugh! he knew how to calm me down! Felt sooo good!!

[imariver]

Can't really remember HOW it was, but I do remember the first guy that fucked me. Being my first time, I'm pretty sure that it didn't feel too good, BUT . . . . the idea that some guy was actually fucking me was a rush in itself. Up until then my mind-set was, "fucking was what a man did to a woman". but here I was on all fours with some guy kneeling behind me fucking away like there was no tomorrow. So, mentally ans emotionally, it was the greatest feeling in the world, physically, it must have been good cause here I am today still doing it. BTW, I still to this day have a pic, that my wife took. This is it, a 30 something year old pic that my wife took of me getting fucked for the very first time.........(by a guy)54032

[marine20]

actually my first time was pretty good. years ago , before aids, i went to an abs to get a blowjob, maybe even give one. a guy came in my booth, and we sucked each others cock. then he wanted to fuck my ass . i never did this before , but i said what the hell , i wanted to try everything. so he lubed up my ass and his cock , and preceded to fuck me. as i recall , i didn't feel much pain ,and i liked the idea of being somebody's bitch. being bent over and being fucked like a cheap whore, by a stranger felt so dirty and erotic at the same time. he didn't fuck long before he said , '' your ass is so hot'' , and then came in my pussy. i felt like a sexy whore with a strangers cum in me. on the way home i felt his cum leaking out of me , and i thought , this must be what other whores feel like after they fuck. it was a sensual experience to feel like a female slut !

[gotoguy]

Nice!! Wish i was there

[Imboggs]

My first time was in a hotel in NYC. If felt so good, but the guy came after about 4 strokes. Disappointing. I’ve bottomed somewhat regularly and really enjoy it. Last guy I bottomed for is really, really thick. I absolutely loved it, once it opened up. A little pain @ the beginning, but he was gentle and patient. Unfortunately I up getting hemorrhoids and have had some bleeding too. Sucks as I REALLY, REALLY like this guy. But not sure I can do it again. No bottoming for 2 months now & I definitely miss it!

[allmyassbelongtocock]

When I was 24, I visited my cousin in NYC while I was driving to Chicago. She told me I could stay at her place for a while if I wanted, since she was leaving for a few days for work. We ate dinner at a restaurant, and she gave me the keys to her apartment. What I didn't know, was that she had a gay roommate. They were around 27 or 28 years old at the time. He was at the restaurant with us, and was hitting on me all night, saying how pretty my lips were going to look around his cock, and how much he was going to ravage my ass so much that I wouldn't be able to walk. I was blushing, but laughed it off. My cousin said he was harmless.

My cousin left to go to the airport, and I went to the apartment to get some sleep. I found her room, and crashed on her bed. Her roommate came home maybe an hour or two later, and knocked on the bedroom door. I answered it, and he apologized about his behavior earlier, and asked if I wanted to drink with him while watching a movie. I said sure. He made us a cocktail, and we sat on the sofa while the TV was on. He asked what movie I wanted to watch, and he started to list some out. They were all gay porn movies. I told him I wasn't interested, but he picked one out, anyways. He asked if I ever watched gay porn, and I said, no. He said to at least give it a try. I laughed, so I said sure, whatever.

As were we watching, he asked what I thought. I said it wasn't really my thing, I preferred women. He then asked if I wanted to watch straight or lesbian porn. He was so straightforward about his sexual advances and watching porn, at that point I was like, well, I watched gay porn with this guy, might as well watch porn I liked. I said straight porn was fine. While we were watching, he sat closer to me, asking me if I liked anal. I said I did. He asked me if I ever played with my ass. I told him, yeah. He asked me if I ever wanted to suck cock, and I told him, yeah. He put his hand on my hand, and put it on his cock, which was getting hard. He said that if I wanted to suck cock, tonight was my chance.

He unbuttoned and unzipped his jeans, and pulled his pants and underwear down. His cock was pretty huge, but at that moment, it was still not fully erect, just semi-hard and flaccid. I was just staring at it. When I looked at him, he said to just start kissing it, so I did. Then I started licking it, and then putting it in my mouth. I was thinking how wonderful it was, having another man's cock in my mouth. His cock started to get bigger and harder, and I'd say it was close to 8 inches, and it had some girth. I was only able to put half of it in my mouth. He told me to open my mouth as wide as I could, and to relax my neck. Slowly, he pushed my head down. I gagged a few times, and tears were coming out of my eyes. I was getting closer to putting all of his cock in my mouth and throat. He asked me if I wanted to keep sucking on his cock, or if I wanted to get fucked in my ass. I told him that I wanted to get fucked in my ass.

He started to take my clothes off, and then his clothes. He told me to turn around. I asked if if he could put on a condom, but he said that he didn't have one, but he was safe. I was naive and dumb at the time, so I said that it was okay. Luckily, it was true (I got tested a couple of times afterward). He rimmed my ass for a while, and then put his cock inside me. It was nice and slow. When he felt my legs and butt tightening up, he'd slap my ass and told me to relax. He got deeper and deeper inside me until he had his entire cock up my ass. He reached around and stroked my cock while he fucked me from behind. I was moaning with every stroke of his cock. Unfortunately, he didn't last long, he came inside my ass, and I immediately came as I felt his cock throbbing in my ass.

That was just the beginning. We showered together, and slept in his bed. He woke me up later that night and we had sex again, then we slept some more. In the morning, we ate some bagels and fruit, and then fucked some more. He had some weed that we smoked, and although I don't remember much, I remember that we fucked a lot, and he had recorded some of it. There's a sextape of me somewhere, sucking on his cock while he was cumming. Of me getting fucked from behind, and then turning around to suck on his cock after. For some reason, I didn't seem to care. I was turned on by how uninhibited I was. I have an inkling that he showed my cousin the sextape, but she hasn't said anything about it to this day.

[Neonaught]

As first experiences go that one strikes me as pretty good. It is good you were able to be so uninhibited and enjoy yourself!

[Robin Black]

I was 13 my first time. He was 15.

Our moms were best friends and as children we played doctor (probably a bit more than most). They had moved away for about 4 years, but moved back after his parents divorced. Our moms, both being single, spent a lot of time together, so we did too. One night, our moms decided to go out and left us alone. We were looking at an old Playboy and he asked if I remembered playing doctor with him. Of course, I did (and had a massive crush). He asked if I wanted to play doctor again and within minutes we were naked. Our "game" was much more advanced and, in no time, I was sucking on him. He was really hard and pulled out and climbed over my back, sliding his cock up and down on my crack, dripping precum on my hole and making me slick. He pressed against my hole and pushed in slowly. It hurt a lot but I didn't want him to stop. He got inside completely and began humping quickly until he came inside me. What a rush!

Being young, he got hard again quickly and fucked me 2 more times that night. After that, we were inseparable.

My first time was when we were almost that same age (actually, I did not have pubic hair yet). We had been playing various games that included sucking and fingering and even some spanking, and then one afternoon, in our secret "hideout: in the woods, he asked me if he could fuck me. We had found an old automobile bench seat that had somehow been discarded and hid it in our hideout, so I took off my blue jeans and pulled down my briefs and laid on it on my stomach. I think he must have used spit to lube my little hole, but I remember it wasn't uncomfortable at all when he started entering me. To tell the truth, our penises were still pretty small at that point, even when they were erect, so that probably accounts for his ease in entering and my immediate feeling of enjoyment. We were both really aroused, so it didn't take long before he climaxed inside me. Even after he came, his penis stayed hard and he continued to fuck me for several minutes. It really felt wonderful. He was sort of hugging me, and it just felt great being that close. I was very relaxed in one way, but my own little penis was rigid! He had only recently been producing semen, so after he finally pulled his penis out, I could feel the cum running down my balls.

[grover]

The first time I had sex with a man. I met him in an adult theatre and never got his name. I told him I'd never been with a man and he told me he understood. We went back to his place and got naked. He was a very good teacher. It helped that he had a 7 inch cock. He would do something like rim my ass to me then let me do the same thing to him. When he stuck his dick up my ass I almost came. When he did shoot his load into me I all but started purring. I have loved anal ever since.

[Tarz1986]

I was 45 years old. He was the first dick I had in my mouth. After our 3rd time together.l asked him to fuck me. I had been using a dildo between the sessions to loosen up. He fucked me bare back. I felt great and no pain.

[Tarz1986]

I was 45 years old. He was the first dick I had in my mouth. After our 3rd time together.l asked him to fuck me. I had been using a dildo between the sessions to loosen up. He fucked me bare back. I felt great and no pain.

[BigAlNYC]

I was 21 and had been thinking about it and fantasizing about it for so long. There was an old vibrator of my sister's that I had swiped and was increasingly using for practice. I had a van (it was the '70s after all) where I had had a bunch of sexual adventures with both sexes. One night in a parking lot near a favorite cruising park I was starting to suck and older man (30s, I think) off when he stuck his hands down my jeans and began playing with my ass. When his fingers made it through to my hole and he began pushing them in I sort of involuntarily pushed back to take them. He then commented that I seemed hungry for penetration and did I want him to fuck me? Well, I didn't have to be asked twice, and quickly down came the pants. I had some vaseline in the van and he began to work it into me (again, it was the '70s) which felt great. Taking his cock though was strange and a bit awkward and it took me a few minutes to get used to his hardness pressing inside me and relax.

But soon enough he had me on my stomach and was fucking me hard like a man who hadn't had any hole in a while. He was grunting hard against my neck and into my ear with every stroke, which I found very hot. Then he thrusted and bit harder and a bit faster and grunted a bit louder and I could feel liquid spurting into my ass. When he pulled out he unexpectedly pulled my head towards his and kissed me hard (I had never been kissed by a man before, it was strange but fitting). He then asked me if I was OK, I said yes, and if I came too, and I said no. But later when I got up there was a big glob of semen on the floor and my cock was dripping, so I guess maybe I did. Even so, after he left and I drove a bit I could feel his cum leaking out into my underwear which made me so horny that I had to stop somewhere dark and use some of it to jerk off my now hard cock, and I came very hard. I also instantly knew that I wanted to be fucked again asap.

[Tight1-4u]

As I have related here before,, I was 12-13 he was 19 just out of high school.. my cousin.. I was sent to spend the summer on their farm.. I shared his bed.. first we slept naked then started hj.. then he sucked me and fingered me.. then was fingering me a lot.. I liked it.. then about a week later started humping my ass crack.. a couple nights later I was on my stomach and he had been fingering me for a good while and had three fingers in me.. he climbed on top of me holding me in place.. I felt him pour a lot of oil in my ass and then felt his cock in my crack.. nothing new he had done it a few times before.. but this time his cock found my pussy hole and I felt pressure agents it.. he said he was going to open my pussy with his cock and to relax like I did when he fingered me.. so I did.. little by little he opened my pussy.. then pushed the head of his cock in me.. he was big and thick.. it never really hurt all that much.. do to all the fingering.. I felt my pussy stretch to fit his cock.. then he slowly lowered himself down on to me driving his cock into me.. once balls deep inside me hi posed for a couple minutes to slow me to get relaxed with him inside me.. then he started fucking me.. slow at first.. the more relaxed I got the harder he fucked me.. soon I was moaning getting louder and louder.. the harder and faster he fucked me., soon he was pounding away at me.. then he stoped and rolled me over.. put my legs in his elbows and climbed on and in me again.. he went in me way deeper this way.. it felt so good I was moaning loudly.. he fucked me pretty hard and blew his cum deep inside of my pussy.. he woke me early the next morning and fucked me again.. I was his and his three friends cum dump that summer.. I grew to need it want it go looking for it..

[grover]

After being stalked and beaten to a pulp on a regular basis by the school bullies, there was no way I was not going to experiment when I got on my own. They (the school bullies) might think I was gay, but I had to know. So, after having sex with several women and throughly enjoying myself, I went to the gay section of a local movie palace turned porn theater, and let myself get picked up. I told the man I had never been with another man and he said he understood. He was an excellent teacher. He would do something to me then have me do it to him, like rim. I had never thought of that before. Ass fingered and toys yes, but tongue? But Oh it felt so good. When it came to anal sex, he was very gentle and fucked me till he came, then he let me fuck him. I was quite pleased with myself. It's still true that whenever somebody fucks me and cums. I want to purr.

[Fiddlestyx]

The first time I had anal sex with a guy was in my mid-30s during a brief period between relationships with women. I'd long been curious what sex was like from the woman's perspective, had lovers who really seemed to enjoy sucking my cock and anal sex. So I decided that given I was at that moment without a female to concern myself with and wasn't having sex it would be a good time to find out if ever I were going to. I answered an ad in 'Pennysaver' (no internet back then) from a married bi-guy who was 46, eleven years older. We talked a bit on the phone about my thoughts on it all and a few days later he came over to my house for some fun.

I'd decided going in that I wasn't going to hold back in any aspect - not just dabble with sucking or something, but kissing, nipple play, mutual sucking, anal; the whole range. So that gent arrives and the first thing I notice is that at 6'4" he's way taller than my 5'7". He asked if that was going to be a problem for me and of course I said "no". I've dated women as tall as 6'1" so height is of no great importance to me.

We touched and hugged a bit and then I just leaned over and kissed him full-mouth. He was a bit surprised as he expected me to be a bit hesitant, it being my first time. Then he just went with it. Clothes vanished, we were stroking each other, frotted a bit and then I took his cock into my mouth, licked it up and down, around the head, licked and sucked his balls, all the best things I'd liked that women had done for me as best I could (he still says I suck cock better than anyone he's met). Having a hard cock in my mouth turned out to be even more enjoyable then I'd imagined! Then he had a turn and we ended up in 69 for a long time, both leaking plenty of pre-cum in the process.

Finally I told him I really wanted to feel his cock in my ass and to get fucked. So I kneeled down with my butt in the air, he lubed my hole and his cock and gradually worked his way in. I was (and still always am) a bit tight but there was only a bit of mild discomfort before things got accommodating and he fucked me pretty thoroughly, with me moving and pushing back against his movement. I loved the feeling of fullness, his cock hitting my prostrate and the feeling of my cock and balls hanging down and swinging around (I've always found that to be sexy, both from my own standpoint and the feeling of the guy I'm fucking). After a while he asked if I'd like to return the favour because he couldn't hold off cumming much longer and of course I took him up on the offer. After some time I felt the need to have his cock in me again and we got into missionary with my legs up and his arms holding them, bending over and kissing deeply from time to time. Whoohoo, that was great as well! Eventually he pulled out, removed his condom and shot a load on my chest. We switched positions and I fucked him until I pulled out and did the same - we kinda rubbed the cum between our chests for a time while kissing and then went for a shower. And that was my first time...

In the three decades since we've had sex many times and in many places. My friend isn't "exclusive" to me and plays with other guys, but only bottoms with me (and I with him). I haven't had sex with other guys solo much, but we've had many threesomes, always with a bottom where we take turns at either end. Somehow it always seems to be my job to get the "third" off, but I love making people cum so...

The sad thing with ageing is that we're generally no longer "all we once were" and while my friend still gets hard enough for a most enjoyable suck the last couple of times he hasn't been able to get hard enough to get into my ass. I guess we just have to take things as they come and enjoy what we have while we have it.

More than you wanted to know perhaps, but there it is.

[oldoralman]

It was a great experience. He used a well lubed condom and my wife had previously used a dildo on me some. It was so great. I yelled for him to pump harder and harder. Unfortunately it was several years ago and I haven't repeated lf. I sure hope I can soon' I want it so much.

[Modude]

Can't really remember HOW it was, but I do remember the first guy that fucked me. Being my first time, I'm pretty sure that it didn't feel too good, BUT . . . . the idea that some guy was actually fucking me was a rush in itself. Up until then my mind-set was, "fucking was what a man did to a woman". but here I was on all fours with some guy kneeling behind me fucking away like there was no tomorrow. So, mentally ans emotionally, it was the greatest feeling in the world, physically, it must have been good cause here I am today still doing it. BTW, I still to this day have a pic, that my wife took. This is it, a 30 something year old pic that my wife took of me getting fucked for the very first time.........(by a guy)54032

Wow, such a hot pic !!!!...made me hard...

[Modude]

Wow, such a hot pic !!!!...made me hard...

Wish I was the bottom.....

[Modude]

It was a great experience. He used a well lubed condom and my wife had previously used a dildo on me some. It was so great. I yelled for him to pump harder and harder. Unfortunately it was several years ago and I haven't repeated lf. I sure hope I can soon' I want it so much.

Mmmm sounds fantastic, I think I'd be the same way.....

[mrheem]

My Story...

https://literotica.com/s/true-first-time-with-a-man

[Dlgrayguy]

My first time I was a little drunk but it was awesome he was a tall muscular black guy he pounded the hell out of me my shoulder was bruised from hitting the wall he came twice it was great ! He was at least 8-9 inches i walked funny for two days

[Dlgrayguy]

Lucky guy that your wife is into it my ex would never but at least she fucked the hell,out me with her strap ons

[Gregshaw]

My very first time getting my ass fucked was by a contractor who was doing a job where I worked. I was 19 & he was probably 30. I accidentally heard him fucking one of the company reps in a locked storeroom late one night when everyone else had gone home. It was electrifying to see him banging away at another guy who was bare ass & bent over. I couldn't get out outta my head but eventually I knew that I had to get the same.

I managed to get to work with him, he was kinda blue collar scruffy & loud but he was alright to work with & I suggested going out for a few drinks on his last day once he'd finished his instalation. Since he liked me he agreed & yeah I lied about my age but back then some bars weren't as thoro in checking IDs.

I was terrified but managed to mention what I'd seen & he was silent at first but I gained his trust because he realized that I'd not said anything. Anyways he took me back to his hotel & eventually I plucked up enough courage to actually touch him coz he wouldn't do anything until I'd shown him I was serious. My hands shook like crazy but eventually I was able to run my hands down to his crotch & touch my first cock. I though i was making a mess of it but I was amazed when he started to get hard & make little groans of pleasure. Eventually we got down to it in bed.

He was VERY careful & took his time loosening me up & backing off when it was too much but eventually I was face down on the bed, legs spread my bare ass feeling his groin bump against me & it felt AMAZING to have his hard cock moving in & out of my ass. It didn't hurt at all. When he came inside me he thrust harder & harder making my cock rub on the towel we'd out on the bed & I ended up shooting my own load in a way i'd never known was possible.

I stayed the night & he had my ass again in the morning with me on the bed my back & ankles on his shoulders & him kneeling by the edge. If last night felt amazing this time felt even better & it has stayed as my favorite position but after that he moved outta state to another job & I never saw him again

[ImBiVersatile]

One of the hottest threads ever!

[bnicks122016]

My first time I was 21 and in college. To that point I had only been with women. I had been doing a bit of nude modeling that turned into some gay modeling. This was back in the 80s, so pretty taboo at the time. It had been mostly been me and mother nude guy that had progressed int o some oral. Which to my surprise I enjoyed.
I have never been sure of the entire situation. The man who hired me was also the photographer, and I had suspected he was just a guy with money who liked guys. And what proceeded to happen pretty much convinced me.
I had just done a solo shoot for him and when it was finished I was extremely horny. It had lasted a couple of hours and for most of it he had me fondling myself etc. So I was ready to get home no jerk off.
The guy was in his 40s, good looking and in good shape, but had never made a pass of any kind at me before this. As we were finishing up and getting ready to go he made a comment about how much I seemed to enjoy the session. I was still nude and pretty hard. I kind of laughed and said that I had and would need to take care of things later.
He said he understood, and at that point asked if I would like some help. I was a little stunned to be honest. The only gay I had done to that point was for pay and never to organize. He walked over to me and put my hand on his crotch. He was very hard and said he would like to help with my problem.
The next thing I know we were in a deep kiss and he had his hand on my very hard cock. We laid on the bed I had been modeling on and nature took over. I unzipped his pants and released a very hard 7? cock. We were making out and stroking each other when he whispered to me to suck his cock like I knew I wanted to. He pushed my head down with very little resistance and I was soon bobbing up and down on his hard cock. He started taking dirty calling me a slut, his good little cocksucker etc. That turned me on even more nd he knew it. I was so hard!
He had maneuvered me into a 69 position and started fingering and licking my ass. That was a first for me and I was ready to explode. When he stopped I literally groaned in agony. He laughed and said he had something I would really enjoy.
I knew what he wanted and he knew what I wanted. He put me on my back and told me to tell him what I wanted. I was so worked up, I told him I wanted him to fuck me. He smiled and lubed up. He was very patient and over the next 10 minutes he was fully inside me. He knew how to fuck a man and over the next 20 minutes made me feel things I never thought I?d feel. After the initial pain I couldn?t get enough. When I came it was the most intense orgasm I had ever had. Shortly father he came inside me and whispered I was his now.
over the next 18 months I had the most amazing sex with him I have had with anyone

[park ave]

I can sum up my first time getting fucked by a guy in two words: it hurt. And the second time it hurt too. A lot. It wasn't until the third third time when I finally got a handle on things that I understood it for the first time.

When I was a teen, I was seeing an older married man, who was, as they say, on the 'down low.' Our usual activity was me blowing him. Weather permitting we would go somewhere deserted (a nearby beach was a favorite destination), although on occasion he'd spring for an inexpensive motel room, and I'd suck him off.

Even when we were outdoors he liked both of us to be naked when I blew him, as he liked me to kiss and lick my way down his body to his cock, and also so that while I was sucking him he could stroke my cock (he had told me more than once that I sucked better when I was horny). At some point, in addition to stroking my cock he started playing with my balls and then lightly fingering my asshole, and that became part of our usual routine while I blew him.

Well one night we're at the beach and I'm sucking him, and, as I realized later, he had squirted a bit of lube onto his finger, which he started to gently work into my asshole. I was slightly startled, but he had me keep doing what I was doing (sucking his cock, that is), and, I have to say that after the initial surprise wore off, his finger moving in and out of my ass actually felt good. Plus it felt sexy to have his finger moving in my ass, with me lying naked across him and sucking his adult cock.

But I was unacquainted with anal sex at the time, so I did not expect what came next. He said something like, 'Here, stay like this,' meaning on all fours, and he moved around behind me, put some more lube directly on my ass, and, taking me by my hips, began to work his (rather large) cockhead into my asshole.

Well. I was, as you may imagine, very familiar with that cock. It was maybe 6 or 6.5 inches, but it was quite thick. It was tough enough getting my mouth around it, and the thought of it in my ass was scary. I tried to relax and follow his instructions, but he wasn't particularly patient and continued to push his cock in. Additionally, our sessions together had always been more about his pleasure than mine. So I gritted my teeth and tried to get past the pain. It felt as if he got most if not all of his cock in my ass. He pumped quickly until he had a moaning orgasm and came inside me. But it had really hurt.

The second time was no better. We followed the same plan, a deserted beach, at night, both of us getting naked, and me thinking I'd just be giving him a blowjob. But he maneuvers around behind me, and despite my misgivings and him urging me to relax, plus him assuring me that it will get better, it didn't. He fucked my ass with that thick cock of his again. Mercifully, he came relatively quickly, but frankly I wasn't loving it.

The third time was actually different. He had gotten us a room, which he didn't often do, perhaps because I had been visibly unhappy the last two times out. This time, however, rather than waiting for him to direct me into doggie position (as I later learned it was called), I decided to take the initiative and, while I was blowing him, suggest fucking while he lay flat on the bed. He lubed my ass and I lubed his hard cock (which was actually fun to do), and, straddling him, I was able to ease myself down onto his cock at my own pace. The pain was still there but considerably lessened, and I was much more aware this time of the fullness of his cock inside me and my ass moving against it.

He was a big man and I was a slim teen, so this position was easy for us to maintain. He held my upper arms and my hands were on his chest so I was able to ease my ass up and down against his thrusts. As my ass moved on his cock, things got heated, and for the first time I was able to feel what it was like to have a man's cock swell inside me and pump cum in my ass as he came. Notwithstanding the first two sessions, it was, I felt, the first time I had really been fucked.

After he had cum and while I was still straddling him and his cock was still in my ass, I could imagine how my girlfriends had felt when we fucked and I had cum in them and my cock still pulsed inside them. It was terribly intimate and sexy. I would have lain down on his sweaty chest and kissed him long and deep, but he never liked to kiss, so I think I just rolled off him. Sex with him was always primarily about him getting his rocks off.

Just as an afterword, I didn't entirely 'get' anal sex until my second lover, who was much more patient. Plus our relationship was reciprocal, whereas with the first I was more of a boytoy. And additionally his cock was less thick (and actually quite gorgeous). Even though our sex was primarily oral, anal sex was with us an act of incredible sexiness and physical intimacy. I'm just glad I had the opportunity to explore unprotected anal sex with him back in the 70s before it became a worry.

[heisaflirt]

I was around 50 yrs old, wife knew I was bisexual and we had met a couple who the male wanted to experiment, they were into the Hotwife cuck scene like ourselves, both of them were really hot and after our first meet we decided to all meet again. He and I texted a bit and talked about each of us being virgins, and we both wanted to experiment farther than just sucking which we had both had experience doing at that point. We decided to meet, him come to our house, and my wife suggested that she leave, I kind of wanted her to stay to watch them a bit, but I really thought it was hot just the two of us so I would not have any inhibitions. I thought that whole week it wouldn't really happen but each day came and then it was "tomorrow" and I knew I had better eat right, douche,,,, research it. My wife had her thoughts as well and she shaved me completely the night before. the day of I was pretty nervous but also excited, when I got home from work my wife was getting dressed to got out to a restaurant by herself that had a busy bar as well. She teased me a bit and then... I was on my own and it was really happening,, He had texted saying he was on his way. I showered, douched again, got out a medium sized dildo and tried to get myself ready. I was very nervous but also feeling pretty dirty as well. we had texted about kissing and we were both turned on by it. when he pulled up I opened the door and just grabbed him on the front porch and made out with him. I thought that was pretty hot that the neighbors may see. We didn't spend a lot of time talking, I had thought we might get in the hot tub, but we decided to go right to the bedroom. The best part of the story is when he layed down and I started making out with him and grabbing his dick,, then I worked my way down and pulled his pants off and... by god after swinging 25 years and seeing a few big dicks and maybe 3 really really big dicks he had one of those 3 holy cow big dicks for real. I had seen a picture next to a beer can but didn't really realize it was literally that big..... I sucked him for a while and then I straddled him and worked his dick in my ass it really went in pretty easy,, I guess I am a dildo slut. I remember thinking I am really getting fucked for real now. He bent me over the bed and started fuckiing me, I remember him saying his wife couldn't take his whole dick in her ass. He fucked me hard and rough until I had to stop. we tried a few other positions I didn't cum while he fucked me but I did leak on the bed. It was maybe the best sex ever in some ways.. a great first time for sure...

[joseluis]

excellent story

[joseluis]

excellent story

[mrheem]

My first time was in college. A friend was over drinking and smoking pot. He should not have been driving so I told him he could crash at my place. He was sleeping on the floor in a sleeping bag. It was cold in the apartment so I told him he could sleep in my bed with me. He got in bed with me and pretty soon I could feel his hard cock on my back. I rolled over and we started kissing and then 69-ing. Eventually I told him I wanted him to fuck me. It took some time to take him, but after that initial "uncomfortable" stage it felt amazing. I came without touching my cock and came right after I did. It was so nice.

[ilovetowatchcs]

My first time was with a married neighbor. I had blown him a few times, and one day I asked him to fuck me. Because I had done it wih dildos and liked the feeling. And he did it slow, then a little faster - then came in my ass. And unless you have been fucked in the ass, but by the right guy and cock, you will never know how sexually exciting it is.

[Sundazzled]

I'll concede that I don't have much experience in this department, but four years ago did find myself playing with, Dave, a 63 year old retired dentist who was separated from his wife and very eager to explore his bisexual side.

Because Dave lived on a secluded 20 acre property in rural Delafield, much of our sex play took place outdoors in Dave's hot tub or on the big redwood deck surrounding it. For the first few months, our encounters typically revolved around mutual masturbation, cock-to-cock play and giving Dave oral. I really had no ambition to explore other activities, but one July evening we were lounging around nude on the deck drinking tequila shots and cooling down between dips in the hot tub when Dave turned to me and out of the blue asked "Would you ever consider letting me fuck you?"

I don't know; maybe it was the tequila talking. Maybe it was a suppressed fantasy to try something new and decidedly taboo. Maybe I just wanted to help a friend fulfill one of the fantasies on his rather large bucket list. Whatever the reason, I found myself saying yes, and the next thing I knew the two of us were boundingbbare-assed up to Dave's bedroom!

We were both anal newbies at this point, and really didn't know what we were doing. I'd been pegged a few times with a dildo during threesome play, but had never experienced the real deal. I got down the the doggie position as Dave applied Astrolube to my backside and to his penis. Since Dave had never been with another man, I agreed to let him fuck me bareback. He was strangely insistent about that. He placed his cockhead against my hole, pushed forward, and went in no more than an inch or two before I began to experience a lot of pain, pressure and an uncomfortable sense of fullness. Dave paused for a few moments, grabbed my hips, and pushed forward again eliciting a yelp of pain.

It was apparent Dave wasn't going to penetrate me in this position, so we tried again with me on my back, Dave kneeling between my legs and my knees draped over his shoulders. He applied more lube, and resumed his assault on my anal virginity. Again, he got only his cock head inside me before I begged him to stop again.

We tried for the next 40 minutes in probably six different positions to get Dave's cock fully inside me, and I dare say he was determined to make it happen. We tried with me bent over, resting my torso on the bed and Dave standing behind me. We tried lying on our sides, we tried with Dave lon his back and me straddling his cock. Ad soon as he attempted to drive his cock home, I felt bright pain and an uncomfortable sense of fullness and pressure. Ultimately, we abandoned the effort.

Over the next week, I had lunch with a gay friend, TJ, who I figured would have some expertise in matters of anal sex. After he got over the shock of learning that I was actively bisexual, I told him about my disappointing first try at bottoming for Dave. TJ explained that successful anal penetration can't be rushed and requires several steps. First he recommended an enema with warm, soapy water to clean the anal cavity. Then he recommended having Dave insert one or two fingers to stretch my opening. Then TJ recommended having David work a dildo or butt plug into my anus before attempting penetration with his own cock. He cautioned that anal sex requires oceans of lubricant, and recommended buying a syringe for putting lube inside my anal cavity. Last, my gay friend advised that first timers generally find it easier to be on top "cowboy style" and lower themselves onto the penetrating partner. This, he said, puts everything at the correct anatomical angle and gives the partner bring penetrated control over the speed and depth of penetration.

Following a shopping trip to Walgreen's and the the local sex shop, I phoned Dave and offered him another go at my virgin ass, and he invited me to come out to his place the following weekend.

Long story made short, we followed TJ's instructions to the letter. I actually sort of enjoyed having Dave administer the warm water enema, and the feeling as he inserted one, then two lubed fingers into my opening. After about 15 minutes of fingering, I asked Dave to lube up my pretty, pink dildo.nI tried to relax as he worked it inside me with minimal resistance. There was lots of pressure and an odd sense of needing to poop. But there was no pain this time -- just mild discomfort when he pushed the thing past my sphincter. Dave worked the dildo rhythmically in and out of my backdoor for probably 10 minutes. Then he applied a virtual flood of Astrolabe and told me I was about to receive a good fucking.


Now lying on his back, I straddled Dave, reached behind, positioned his cockhead against my opening and bore down firmly. As before, he went in maybe two inches. I breathed deeply, then bore down again, and to my astonishment, Dave's cock went right in -- right to the hilt!

I began bouncing up and down on Dave's penis, occasionally reaching back to fondle his balls. Beong fucked wasn't particularly pleasant for me, but looking into Dave's eyes, I could see he was in ecstacy. After about five or six minutes, I could tell Dave was getting close. His breathing became ragged, his ball sac was drawn up tight, his nipples were erect. All the signs were there... and then I felt this cock go absolutely rigid inside me. It twitched and throbbed, and Dave groaned loudly, "Oh, fuck,yeah!" I knew I was receiving a load of his cum deep inside me ... and the thought of it strangely thrilled me.

We lay together in a post-orgasmic heap until Dave's erection subsided and his spent pecker fell out, causing a trickle of fresh semen to flow out of me and down onto my balls ... proof positive that I had actually been fucked by another man.