how was your first time getting fucked by a guy?

[Secretcumlover]

I played around with a friend when I was around 12. I remember spreading my ass cheeks while he pressed the head against my asshole..but we never got it inside. We knew nothing about lube at that age..decades before the internet was born.
In my 40s I met u with a guy on CL and we hooked up a couple times . It was mainly oral but on the second trip he straddled my cock and rode it. You could see the pain and pleasure in his face and moans. Without much lube I was getting sore so had him stop. I asked if he had any lube and had him lube up my ass while I laid on my back, legs in the air and stroking my cock. He got me lubed up and soon felt the head of his small cock pushing inside me. He was only around 3" and pretty thin so it wasn't too bad and felt fucking amazing. I lifted my hips towards him to help him fuck me.. I remember moaning in pleasure amd telling him to fuck me harder. I think he got about 3 pumps in before he shot his load and stopped. I was so bummed it ended so quickly. I still hope to find a guy with a decent sized cock to fuck me someday.

[Neonaught]

My first attempt at bottoming didn't go well. He didn't know what he was doing and just shoved his cock in me and it hurt like hell. To add insult to the injury, he came in about 6 strokes and it was over before the pain passed. After that, I'm all top.

[smallandbi]

I was 21 and a guy in his late 50s was hitting onto me in a bar. He knew I was a virgin and boasted that he had a big fat cock, and he could break in me. I was excited and went back to his flat. I was drunkenly trying to fondle him through his pants. I could not really feel anything though. He pulled his pants down and freed his cock. It was no more than 2 inches at best and totally soft and very slender. I thought my cock was small, but this thing was miniature. He made me get undressed and down on all fours and smeared loads of KY jelly into and around my hole. He was franticly rubbing his cock trying to get it hard. He was struggling to get even semi hard, and could not penetrate me at all. His cock just kept bending with every attempt to fuck me. Then without any warning he came all over my bottom. Not shooting but it just oozed out and kept oozing. He apologized and said he suffered from ED and not had sex for nearly 25 years and simply got over excited. We had some more beer. We watched some gay porn, and we tried again after an hour. I sucked his old and now very shrivelled cock like a limpet. It stayed completely soft, but oddly he groaned a lot. When I flicked my tongue under the tip of his helmet, he kept saying he was about to cum again. He never did and his cock seemed to get smaller. I finally deemed it a lost cause and gave up. I made my excuses, cleaned myself up, dressed and left. I was thoroughly disappointed.

[Spininmywheels]

Spinin, the fun is in the details! You really should share.

OK by~his~side if you must.
I met a couple a while back on line and after several weeks of messaging each other we all decided to meet.
They invited me over to their home and they were the sweetest down to earth people you?d ever want to meet. When I got there we sat around taking and the wife (Jane) offered me some snacks and a beverage. During our conversations we discussed what we liked and disliked, Jane said that she doesn?t usually join in but love to watch and assist if necessary. Not long afterwards the husband (Joe) were in the living room playing with each others cocks and then proceeded to suck each other. At one point I was sitting on the edge of the couch while Joe was sucking me very nicely, I was enjoying it immensely and I leaned back on the couch with my eyes closed and enjoying the bj. As I was blissfully relaxing Jane leaned over me and placed her nipple against my lips, I opened my mouth and proceeded to suck on her tits.
Not long after that Jane suggested we move into the bedroom where we would be more comfortable. One there Joe and I continued enjoying each other as Jane watched. After a little more time Jane asked if I?ve ever been fucked by a guy? I replied no. She the asked would you like to? I without hesitation replied Yes I would.
They were both happy to here that.
I proceed to get on all fours and Joe started lubing my as up and playing with it for a while loosening it up for his entry. In the meantime Jane is talking to me and encouraging me and coaching me as things developed.
Then the time came. Joe asked if I was ready and I replied yes. He then slowly, carefully and patiently worked his hard cock into my awaiting ass. After a few minutes he was deep inside of me and now fucking in a nice rhythm. I was enjoying the hell out of it. And then when I didn?t think things could get any better the unthinkable happened. Jane knelt alongside me and started to stroke my cock.
Now I?m being fucked by a guy for the first time and being milked by his wonderful wife.
Joe continued fucking me an then blew his hot load into my Virgin ass. After Joe shot his load Jane continued milking me until I blew my load and then collapsed on the bed.
Afterwards we all laid there with great big smiles on our faces.
It was a great time. We did get together several times after that. We are still in touch but has been years since we got together. I miss them and the times we had together.

So bi~his~side, is that detailed enough? I enjoyed telling it and sort of reliving it.