First anal

[Robin Black]

Just curious: how old were you the first time you took a cock anally? I was 11 and so was my friend.

[NJwood]

60. I never had any interest. After years of getting rimmed by wives (not together!), and a decline in my wife’s sex drive, I was desiring different ways to stimulate myself. That led to curiosity about being fucked. The first time did not go far as he was in just too much of a hurry to get his dick in me. No lube so I shut it down. The next time was much better and had me willing to go again. Since then I’ve only had a range of dildos to play with. As that has been getting easier I’m really looking forward to getting fucked again.

[Tight1-4u]

​I was 11-12 he was 19 and is friends were 19 as well

[Bi_bayarea]

Early 30's, it was a great first time. I've taken many since then as well.

[Jozyxt]

Never.

But I've thought about it a lot since I started sucking cocks. I have realy enjoyed several differn sized didloes and vibrators, so I can't imagine that a cock attached to a real man who is also getting pleasure from my ass could feel anything but great. We will have to see.

[lust2021]

not so long ago 27 now i am 28 but i have experimenting with dildos for years so it went smoothly and the cock was very good but i didnt get an anal orgasm, my third one though was with a very thick cock and a guy with endrurance and he gave me the best handsfree multi orgasms...trying anal with a real dick have changed something in me i cant put my finger on but something have changed especially after my frist time getting bred

[Opportunist]

I have topped a few husband but never taken a dick in my ass. A couple of anal fissures due to tropical parasites and a fistula have made me wary; but sometimes I masturbate thinking of getting fucked or spit roasted by a pair of guys or well hung trannies from Buenos Aires and taking a big raw load in my ass. So some day. Maybe.

[tongueteaser]

MMMM WOW. I have not yet. Main reason I am smaller there and tight. I had my girlfriend put a finger in me and surprised me as she was jerking or sucking me and I about came all over right away. She is very petite and could barely get two fingers in me and I was being stretched. I have always dreamt about the same guy I sucked on also fucked me. Just that one and only cock use my ass after I sucked him. Love to be slowly fucked bent over and cummed in a few times.

[NEWTOOTHIS]

I was 13 and so was my friend I was really nervous at first but really liked it afterwards especially him cumming inside me we fucked each other for that whole summer in different places then he moved and I haven't done it since but think about it a lot !!!

[DMercator]

I was in my 50's. It took a long time for me to admit to myself that I liked my ass being played with and longer still to move from toys to wanting to be fucked by a man. I was fortunate in that my first was gentle, experienced, patient and not too large. I was also fortunate in that he treated me like a lover rather than a hook up. He laid me on his big 4-poster bed, put my legs over his shoulders and fucked me until I came all over myself. I never had a desire to kiss a man, but when he was done and leaned down to kiss me with his cock still in my ass, it was pretty damn nice. A thoroughly enjoyable first. My only regret was that I waited so long and that I haven't had more opportunities since.

[John1971]

Haven't yet, but would love to have it happen.

[Neonaught]

I have always been a total tp man but decided to try the bottom for the first time. My top had no idea what he was doing and just shoved his cock in to the balls in one go. It hurt like hell and by the time the pain eased he was done. Not a good first experience. Since then I just topped. Not long ago, my favorite bottom guy complained about his girl not putting out so I let him fuck me. He was very careful and it felt nice. The act didn't really do much for me but I love him so much I really enjoyed seeing how much pleasure I was giving him. Now every time we get naked we flip fuck and we're both loving it!

[BackyardShaman]

I was 12 with a friend the same age, we were curious about girls and sex, had some time alone together and decided to try it, no lube, I couldn’t penetrate him he was too tight, but he got his dick in me. I remember thinking it felt weird but I kind of liked it, he was hard but not very big, when I got sore he pulled out.

[MontyinHamilton]

50, I could barely feel his cock inside me, I liked playing with thick 8" or larger toys for yrs and he wasn't as endowed sadly for me, he came in a minute or 2 so it's all good for him, maybe next time lol.

[Christopher South]

I was 53. I had been playing with my ass on my own since I was 12 so was used to it. The first guy was only about 4.5" and it was good for my first "real" anal. Have enjoyed it since but I'm finding guys my age prefer to bottom so I haven't been topped in about 7 years.

[hung4you]

I was a 19 yr old collage student, Didn't know it at the time but I had 2 gay roommates who introduced me to this lifestyle. My 1st anal was incredible and do it as often as I can even to present day. Lucky for me I have a regular who fulfills my naughty side often.

[dlutzka]

I was 27 was like oh wow not bad at all he was 57 so much fun big cock at a gay bar bathroom I couldn't resist.

[centillini]

I still haven't had my first real cock in ass Yet. But when 40 gf turned my interest by having me suck her strap on and fucked me many times. Guess I
need not be so picky, lol.

[RisingBi]

Not yet, but my recently ex-girlfriend fucked me in the ass a bunch of times with her strap-on 8" dildo, and before that I fucked myself missionary and cowgirl many times with my dildos. But whether it was my girlfriend's "cock" or my dildos, all I wished while getting ploughed was that it was a real man with his real cock fucking me. I've had many of the out of this world, mind blowing prostate orgasms fucking my dildos. But unfortunately with my girlfriend it never happened: I think that the fact that she was a woman kind of interfered with my whole fantasy and imagination of the whole gayness of a man and me having intercourse and the orgasms his cock brings me, which is so arousing.

Now that I broke up with my girlfriend just before the pandemic hit, I'm actively looking to lose my bottom virginity with a real man, and fulfil my destiny. But it's been challenging during this pandemic, and the fact that most guys are bottoms, which of course I also love, since my tongue and cock just love so much to be deep inside other guys, doesn't make it any easier. Whatever way you slice it, gay fucking us just such beautiful intimacy!

[jargon]

I was fourteen and it was with a younger boy, about eleven. It started with him wanting to feel my cock through my pants and I let him. Then I felt his cock. This progressed to both of us showing our erect cocks to each other and touching them. One day, when we were both alone at his house, he asked if I had ever had a penis up my butt and he offered to do it to me. I loved it, though it was more or less like feeling a finger in my ass and did not last long. But it opened up a whole new world for me. Soon, I was sticking my finger in my asshole whenever i had the opportunity. This led, throughout the years to many other phallic objects and eventually dildos. My wife (I am now a widower) used to peg me with a strap-on which I took great delight in. But I have never had another cock up my ass since that first time when I was a kid.

[csreef]

I tried Anal (receiving) a few years ago. . .It didn't go so well. . .

[wb4all]

I was about 5 when my friend and I tried it on each other but nether of us could get it in, we also tried it on our other friend a girl who oddly enough didn’t get a cock (lol) we were all same age. Never again until I was in my late 50s had been using a few dildos and other odd assort items but my first real man fucking me was so amazing and unbelievably better than I’d ever Amgened.

[Jozyxt]

I tried Anal (receiving) a few years ago. . .It didn't go so well. . .

Can you elaborate?

[ScottSwallows]

19.
I was nervous and couldn’t relax so it hurt a little.

[Kysquire]

not so long ago 27 now i am 28 but i have experimenting with dildos for years so it went smoothly and the cock was very good but i didnt get an anal orgasm, my third one though was with a very thick cock and a guy with endrurance and he gave me the best handsfree multi orgasms...trying anal with a real dick have changed something in me i cant put my finger on but something have changed especially after my frist time getting bred
Very interesting. I have been fucked a couple of times. Maybe there is hope yet.

[Fzmr9t]

My first time was with another married guy. He was in his 30?s I was in my 50?s we used lube and a condom and he wasn?t huge so it went right in and I felt pressure but don?t recall any pain

im hoping to have another experience this evening

[csreef]

I tried Anal (receiving) a few years ago. . .It didn't go so well. . .

I tried Anal with a guy, and I was very tight...He tried some toys on me and when things didn't go in, he got more angry by the second. When he got off the bed and clenched his fist and looked like he was going to hit me, I left. End of story.

[Jozyxt]

I don't remember if I posted this her or not. My first and only time penetrating a guy was when a regular cocksucker set up a glory hole. At first he started sucking. then took a short break and inserted my cock in his ass. I noticed the coldness of the lube and the looseness of his ass compared to his mouth. I pulled out, let him blow me, then left.

I had previously told him no penetration without condoms. Way too risky for me.


It was too bad because up to that point I had enjoyed our occasional explorations in pushing my MM experiences and he had given me some wonderful orgasms. I think about getting back, but any guy that does that is too big of a health risk for me.

[Nocockyet]

Wow, so many similar stories. Especially the ones where they've been playing with dildos since teenage years but still haven't gotten with a lover yet. I'm 51, enjoy anal with my dildos and butt plugs at least 5 days a week. I didn't start thinking about having the real thing until a coupl,e of years ago. Probably right around the time my wife's heath went downhill and our sex life ended. Something shifted, I was getting bored of regular Porn and thought I might as well take a look at gay Porn since I'm always playing with cock. My mindset started to change, and I started fantasizing about giving someone pleasure with my man pussy. I'm now at the point where I know exactly what I want, but have no clue how to get it. I am so afraid of just meeting on a app and going to some strangers house. I'm really discouraged hearing that tops are few and far between. What's the best way to break that barrier?

[Blmbiguy]

I was 14, he was my best friends older brother who was 16. My best friend and I were sleeping outa in a tent one night. His older brother came home from seeing his girl friend. He was horny because she didn’t let him fuck her that night. He came in our tent, and layed down with us. We started talking about sex stuff. He started rubbing my cock, then started sucking me, I sucked on his cock,(first time for me to suck cock to), he was about 8” and thick. He decided he wanted to fuck me, so I agreed. We didn’t have any lube except spit. I remember it hurting like hell. I eventually made him stop, and ended up stroking his cock until he blew a huge load. A couple of night later we got together again, this time with lube. We sucked each other, he fucked me and filled me with a huge load, then I fucked him too. We fucked each other on a regular basis for several years.

[Bi-Rõnin]

37. After my 1st divorce. A guy from an online add, we met outdoors in the nearby desert late at night, he bent me over my tailgate and took my virginity

[Shelby57]

Five years ago. I've been playing with toys for a long time and finally decided to go for it. Of all things it was a CragisList ad. Met the guy at a restaurant near my apartment. We decided we like each other and headed to my place. We made out for a bit, then I sucked him for a while. He complained that he had a hard time getting off from oral and asked if he could fuck me. I said yes. It was some of the best sex I ever had.
We were being safe, using a condom but it broke, so I got bred my first time, too. Have to admit, I liked the way it felt when he came inside me.
Saw him once more and then he ghosted me.

He's still the only one to have me.
If he called me today, I'd say yes. He was that good.

[mwm60fr]

Robin Black: Did you enjoy getting fucked for the first time? Where were you and how did you decide you wanted to be fucked?

[Fzmr9t]

I was in my early 50s in San Antonio it was with another married guy that I met online and had been with a couple of times enjoying each other?s cocks (69) I mentioned to him that I wanted him to fuck me, do recall if I was that forward about it, but he got the idea because the next time he brought a condom. I had some lube and we lubed generously I got on my hands and knees and with a lot of pushing and a little pressure, I felt him ?pop? inside of me. I really enjoyed the feeling of him moving in and out of my ass. I hadn?t thought about being ?cleaned up? beforehand, but fortunately there wasn?t a mess! Afterwards when he came out he pulled off the condom and I cleaned him up with my mouth. Sure miss that guy!

[mwm60fr]

We were probably in the 6th or 7th grade and was still maybe a year before puberty. We had been jacking each other and sucking each other for several years but without being able to cum yet. But it still felt good and was was fun to be naked and rub naked bodies against each other. Our playground were the woods by our houses. One day while in the woods for some reason and it's been too long ago to remember but we decided I would fuck him. We had tree houses we slept over in during warm weather and were we went to get naked and suck and jack each other. He got on his stomach and I spit into his hole and slowly penetrated him. It was the most incredible feeling I had ever experienced at the time even without humming it was great. I have that memory burned into my head and it will never go away nor do I want it to go away. He has and still has to this day one very sexy ass that is still fun to bury my face in between those cheeks. He was my best friend and I still consider him my best friend. You have very few friends that you can tell them anything and they won't judge you. Just wish we lived closer and could get together as often as we would want.

[SEMichiganman517]

The first time I topped another man was pure amazement. We had messed around through out high school and were hanging out in our mid 20s. Came home from the bar and immediately went to sucking each other off on the couch. He was quite drunk and begged me to put it in his ass. My 7.5 cut cock was throbbing so hard that I did not object. His asshole did tho and we had a hard time getting my cock inside him. Finally after lots of lube and stretching his hole I was able to pop my pulsing head inside. It was all over after that, it felt SO good that I immediately plunged balls deep and got on my tip toes to go as deep as I could. I came exactly three pumps later he was begging me to keep going but he was so tight, that I popped out as soon as I came. I have yet to feel that amazing since then.

[Cdnbi]

First time I was 28 just experimenting met a guy he wasn’t huge like maybe 5” uncut but a great starting point. After that point it was hooked. I also have 0
desire to do anything but be a bottom when I’m with a guy.