When was the first time you had anal sex

[13788]

calboi:
The first time i had anal sex was when iwas 13 years old. I was over at my friend house and i didn;t know he was gay. He started to take my shirt off and kissing me. Then he took all his clothes off and i took all my clothes off. I started to touch his cock and his balls. He turned me around and started fucking me thorugh the ass. :grr: He was screaming because he got a orgasms and then i was just maiking noises becauses he was pushing it in very hard and i like that. Now I Ufck him through the ass very hard and he does the same to me. Then we give each other blowjobds. So that was my first time having anal sex.

 

[CharlieDick]

I waited a long time. Then one night I went to the hot tub and there was this big black dude there in a skimpy yellow bikini. We got to talking, and when the talk got around to jacking off, we both admitted that of course, we beat off. So he asks if we can go over to my apartment and jack off together. First I get out of the hot tub, and as I'm standing above him, he starts getting out of the tub, with his 8 inch long, very wide and black, hard dick straining out and above the line of his bikini. We go to my place, and sit on the couch jacking off. I started sucking him, and we got on the floor doing 69. I couldn't swallow 8 inches; he barely swallowed me. then he got me down on my back, jumped on top of me, put my fat cock inside of his ass, and rode me like a rider atop a horse. When he left, I kissed him on the lips. He came back the next night, and I just laid him down on the carpet on his back and fucked him good.

when was the first time I got it in the ass? Asian boy, who said he was celebrating his 18th birthday. We both got naked, I picked him up in my arms, and carried him to the bed. After a lot of sucking each other, he grabbed the condom and slowly put it on his skinny 4.5 inch cock. He took it slow, easy, and good. Many times later, I got fucked by ones that were maximum width, and the longest I've had in my ass was 7.25 inches. Now I can jack off while I'm being fucked. Like it will happen about an hour from now. time to sign off.

 

[Pene_Negro_Grande]

Never had the pleasure...I have done it once to someone - great from my point...

 

[Edmond405]

i was 20 years old
in college
with my first bf
he was my first bj
and my first fuck, too.......i liked topping more than bottoming at first.....then, after we tried different things, i like both.
the first time was after our fraternity party and we were both drunk - i've never been so hard or had such an extreme orgasm before or since.....nothing is ever like the first time

 

[tightfit]

About 12 I think (can't remember for sure).
Topped a school friend in his bedroom listening to Pink Floyd.
It was great!

 

[D_Mallaber Manynuts]

I was about 11, my friend about 12 and the son of the headmaster. He seduced me in his parent's bedroom, got all my clothes off (before he removed his!) and sucked me off. I was in heaven - he turned me over, pulled out his cock (smaller than mine) lubricated it with something to hand and, before penetration, inserted a toy sword into my anus. He pulled it out, rimmed me with his fingers, then entered. Not painful cos he wasn't big, but it started me down a bisexual line I've followed ever since...

 

[ben11]

Never did. When I was a freshman in college, a co-ed I was getting friendly with at a party mentioned how she liked anal, but when she first felt my friend start to harden up through my pants, she politely said "how about everything,but that?"

After that, I never brought it up figuring most women weren't interested.

Guys, in some threesomes and couples I've done after my wife died wanted to do anal; giving and/or receiving, but I am pretty straight and have not gone down that road. In one threesome, the woman had her boyfriend do anal on her, but she seemed to do it more for him than her.

Any women care to weigh in here? I am missing out on something?

 

[shad24]

Giving= 14 on the counter in my parents kitchen, had best friend bent over. sucked his dick afterward.
Getting= 17, camping trip with 2 others, they hog tied me. it was great specially since i had been doing them for about a year. Payback?
Girlfriend = 16. she wouldnt do anything else. wanted to remain a virgin??!!??

 

[Honey_Grrrl83]

I've never done it before,my boyfriend is 9.25 inches and he is scared to death that he will hurt me,I really want to experience it though,how do I convince him otherwise? And could he actually hurt me?

 

[B_Spladle]

This thread is so gay it hurts.

 

[larry93455]

This thread is so gay it hurts.

But does it hurt more than actually having a dick in your ass? :biggrin1:

 

[B_Spladle]

But does it hurt more than actually having a dick in your ass? :biggrin1:

I wouldn't know.

:tongue:

 

[larry93455]

I wouldn't know.

:tongue:

My ex girlfriend wanted me to find out, but all she had was the artificial kind. I rejected both it and her. I finally let a girl use a butt plug in me. It was small, but it sure hurt. How can guys or girls get a big one in them? I can understanding wanting to fuck anally, but couldn't take one in. I guess some guys are more man than I am! :biggrin1:

 

[D_Lawsonne Lackingnuts]

Anal virgin here! I wouldn't mine trying it, but it seems like it would be slightly painful.

 

[Mirai]

does pegging count?

 

[Matthew]

does pegging count?

Absolutely.

 

[jeff black]

Absolutely.

What's pegging?

 

[Matthew]

What's pegging?

When a woman straps on a dildo and fucks her boyfriend/husband.

 

[D_alex8]

When a woman straps on a dildo and fucks her boyfriend/husband.

That would explain how that phrase passed me by.

And to answer the question in the thread title: it was when I was 19, for money.

*runs off after that sordid little tidbit*

 

[scottmac]

I've never heard of "Pegging" before. Thanks for the info.