I've only been f*cked twice when I was 19. and it was my first boyfriend who took my anal cherry. I met him online, we chatted a lot, hooked up, and we ended up kissing and sucking each other's cock in his pad. By then I was so horny and I wanted his cock up my ass (even though I was an anal virgin at the time). First time we tried I couldn't stand the pain, so we held back and he started licking my asshole and opened me up. The second time was the charm, and his cock ended up deep in my ass. He f*cked me till he came, and then he started jacking me off until I came.
First time anal , male or female
- Thread starter sinfulallure
- Start date
Stable_Boy
Experienced
- Joined
- Dec 8, 2006
- Posts
- 31
Toronto,Ontario
I'm still bi curious mainly because I haven't found a couple to try it with yet.Most of the bi guys I talk with are orally bi and not anally bi so its really tough finding someone to try it with.Im love ass play and have a couple of vibrators that I like to use and would even like to meet a woman with a strap-on but so far without success,so for the moment I'm still an anal virgin.
I'm still bi curious mainly because I haven't found a couple to try it with yet.Most of the bi guys I talk with are orally bi and not anally bi so its really tough finding someone to try it with.Im love ass play and have a couple of vibrators that I like to use and would even like to meet a woman with a strap-on but so far without success,so for the moment I'm still an anal virgin.
Cenobite
Really Experienced
- Joined
- Mar 13, 2004
- Posts
- 123
Well I posted about the first time I accepted anal, but not about the first time I gave anal 
Now I do have a tendency to hang out in chatrooms online, and so I was in a particular gay sex channel on IRC and managed to hook up with this one bi guy who was interested in some guy on guy fun and I figured why not.
So anyway he came over to my place, and we kept away from general other stuff as he was there for only one thing really.
Started out as general kissing, caressing, basic flesh on flesh action which later progressed to each of us taking the other in his mouth in turn.
We even got to the whole rubbing of our cocks together and jacking them off slowly (what is it with guys wanting to rub them together like that) and after a bit of that he tore open a sachet of lube and started to finger himself and loosen up, so I figured out pretty quickly what he wanted.
However what I didn't figure out was that he wouldn't give me a chance to put on a condom, he just up and mounted my cock and slowly slid down to the hilt.
Given that the first guy I'd been with hadn't manage to do that exact same thing caught me a bit off guard, and by the time I recovered it was too late and I was all the way in.
Well he began to ride me, and it was wierd feeling his cock hit me in the belly on the downstroke, but overall it all felt good. I didn't exactly cum, and he jerked off on my belly but it was generally fun.
I did feel somewhat used and soiled though that this guy had totally ignorred all precautions and I naturally urinated shortly afterwards and had a shower paying extreme attention to cleaning my foreskin and such and was quite worried for awhile afterwards.
I moved house not long afterwards into a place with a mate and thus didn't hook up with that guy again.
I would like to say that was my only situation of unprotected sex, but alas it hasn't been, I've messed up a couple of times, but have made sure to be tested regularily.
I've been lucky so far, haven't caught anything or fathered any little bastards, and each time has taught me I need to be more careful.
Now I do have a tendency to hang out in chatrooms online, and so I was in a particular gay sex channel on IRC and managed to hook up with this one bi guy who was interested in some guy on guy fun and I figured why not.
So anyway he came over to my place, and we kept away from general other stuff as he was there for only one thing really.
Started out as general kissing, caressing, basic flesh on flesh action which later progressed to each of us taking the other in his mouth in turn.
We even got to the whole rubbing of our cocks together and jacking them off slowly (what is it with guys wanting to rub them together like that
) and after a bit of that he tore open a sachet of lube and started to finger himself and loosen up, so I figured out pretty quickly what he wanted.However what I didn't figure out was that he wouldn't give me a chance to put on a condom, he just up and mounted my cock and slowly slid down to the hilt.
Given that the first guy I'd been with hadn't manage to do that exact same thing caught me a bit off guard, and by the time I recovered it was too late and I was all the way in.
Well he began to ride me, and it was wierd feeling his cock hit me in the belly on the downstroke, but overall it all felt good. I didn't exactly cum, and he jerked off on my belly but it was generally fun.
I did feel somewhat used and soiled though that this guy had totally ignorred all precautions and I naturally urinated shortly afterwards and had a shower paying extreme attention to cleaning my foreskin and such and was quite worried for awhile afterwards.
I moved house not long afterwards into a place with a mate and thus didn't hook up with that guy again.
I would like to say that was my only situation of unprotected sex, but alas it hasn't been, I've messed up a couple of times, but have made sure to be tested regularily.
I've been lucky so far, haven't caught anything or fathered any little bastards, and each time has taught me I need to be more careful.
Anal Sex, Love It
Anal sex, love it. My wife has a special vibrator that is for my ass only. I like to lay on my back with my knees pulled to my chest. She loves to see my ass and cock totally exposed for her pleasure. I masturbate while she slowly fucks me. It thrills her to watch me shoot cum onto my stomach and chest.
Anal sex, love it. My wife has a special vibrator that is for my ass only. I like to lay on my back with my knees pulled to my chest. She loves to see my ass and cock totally exposed for her pleasure. I masturbate while she slowly fucks me. It thrills her to watch me shoot cum onto my stomach and chest.
Ass made for it
First time was purely to experimant with my bi side. Met up with a man on a chat room and decided to push myself not to back down. Iwas so so nervous and it was looking like all we would do was suck each other untill I got the nerve and asked him to fuck me. He took his time to lube me and with condom on slowly entered me. Although it hurt on entery I loved it knowing he was inside, untill i was used to it he was very careful but when i told him to fuck harder he went for it. It was so good to be used like that and have my ass used so he could come!
First time was purely to experimant with my bi side. Met up with a man on a chat room and decided to push myself not to back down. Iwas so so nervous and it was looking like all we would do was suck each other untill I got the nerve and asked him to fuck me. He took his time to lube me and with condom on slowly entered me. Although it hurt on entery I loved it knowing he was inside, untill i was used to it he was very careful but when i told him to fuck harder he went for it. It was so good to be used like that and have my ass used so he could come!
blklthrjkt
Literotica Guru
- Joined
- Oct 22, 2004
- Posts
- 12,469
First time was with a friend of mine from High School. Both of us were 18, and graduating that year. We both knew we liked guys and decided to experiment. FUcked each other after long sessions of digital play. Lots of vaseline and patience and we managed to do it. It was pretty hot, even though we were both completely clueless as to how to proceed.
We fooled around a few times after that but never fucked again. He ended up marrying and moving to a rural area. He finally came out after a messy divorce.
Me, I have enjoyed anal ever since. Now mostly on the giving end, but I still enjoy playing with toys.
We fooled around a few times after that but never fucked again. He ended up marrying and moving to a rural area. He finally came out after a messy divorce.
Me, I have enjoyed anal ever since. Now mostly on the giving end, but I still enjoy playing with toys.
