First time doing anal

[johnjacobs]

What was your first time having anal sex like? When I first came up with the idea of posting this I was strictly thinking from a bottoms perspective of taking the big cock for the first time. But instead I'd like to know all experiences, recipient and giver of penises and strap ons of all size!

 

[mikeinsocal]

My first experience was with a guy that had a very thick cock. It was spontaneous, so we didn't have a lot of foreplay. I took off my pants and underwear and was watching him get undressed...at this point, I had already committed to letting him inside me. I could see his fat head through his briefs and it scared me. I was on my hands and knees bent over when he started to play with my hole. I remember his finger feeling really uncomfortable at first, but then felt good. He ran his cock along my hole and I was anxious about what it would feel like. He eased it in me, and before long he was deep inside. Yes, it hurt like hell, but he kept telling me to relax and to let him in. I eventually relaxed enough that it started to feel good. I was amazed that he was so hard and actually inside me. Hearing him moan was awesome, and he kept saying "you're so tight". When he finally came, I was enjoying the feeling.

I kept his underwear as as souveneir. Lol.

 

[lycanross]

My first experience was with a guy that had a very fat long cock, he was good at foreplay and we had fun, then when he fucked me he made me cum without touching it, i felt on top of the world and he was moaning so loud and his load shot all over me when he finished.

 

[deano-uk]

My first time was with a younger guy than me, I had been chatting to him for ages and got so hard just talking to him or thinking about him.
I drove to his place and started with kissed him pushed up against the wall, then opened his bulging jeans and sucked his cock, then we went into the bedroom, kissing him on the bed and feeling his body.. I said to him, I want you to fuck me, I want that big cock of yours inside me, I started by trying to sit on his cock, but my arse was too tight.. I remember saying it will never go in its too big. He told me, it will, and I will be gentle and as slow as you like...
He tryed but it hurt and was too tight so he rimmed me for about 5 minutes or so and then lubed me up and slowly pushed in, I felt a bit of pain, but loved the feeling of him inside me. After him pushing slowly for a while I said I'm not sure it will all go in, he said here feel and he guided my hand to his balls which where right up tight to my hole. I smiled and kissed him and said well babe, go for it, but start slowly and he gently trust in and out of my tight hole.. OMG it felt so good, why had I waiting so long to experience this pleasure.. - I told him to go as fast as he like and he started slamming me and it was soooo fantastic - i'd never felt so good .. as his breathing got shorter I knew he was going to cum, and I could feel his big hard cock throbbing inside me... he let out a big moan as he shot his load inside me...
We spent the night together and some of the next morning till about 10.30 and we must have tried most positions and he shot about 8 times inside me, over the whole time.. I on my drive home, it felt like he was still inside - I just wish he was...
I just knew at this point, I had to come out... yep all my suspicisioin were true I was GAY and had just been conforming all the previous years

 

[bigbrisguy]

From a tops perspective, its all about the preparation. Ive told guys who haven't taken a cock before that its best to start off with nothing too thick. For those that persist, Ive used a mix of fingers, lube and time to make it work.