When was the first time you had anal sex

Tsk, you ask me the most romantic questions, tallguy.

Bring five-figures (US$) to the table, and we can start talking.

I was 28. Unfortunately for me I was in the closet till 26. After I came out I was too afraid to sleep around, so I just waited for the right person, I suppose. He finally came along about a year later, and after a year of dating, sucking and just playing around, he put it in, and I have to say that it was incredible. He is quite a bit bigger than me. The first time we tried he couldn't get in. A week later we tried again though, and it fit perfectly. I had to loosen myself up with a dildo first, but it was wonderful.

7 months ago I had a needle-prick at work, and swore off sex for 6 months. I just got my final test, which came back negative, and now I'm ready for some nice, big cock again! I was so used to taking him that sex was pretty easy, and now it's like starting from scratch! Nothing's been up there for 7 months and I couldn't even get my 6.5" x 5.5" dildo in there last weekend.

I can't wait to have him inside me again!!!

I was 16 and quite drunk.. altho i knew what I was doing.. just needed the drink to calm nerves..!

I did it to him an then he did it to me, but I'm not that keen on it.. still not.. but it's the whole pain thing of getting the damn thing in there... once it's in it's heaven, but it's just the start that gets me..!!!

hehe!

x

I was 16 when I first topped a guy. We did it in his hot tub. Looking back on it now, it was a pretty cheesey porno-type experience. But we thought we were very cool and grown up.

I wasn't on the receiving end until college, which was a pretty brutal experience. I've had better luck since then, though.

My first one at 17 years old, as bottom. As top whit a shemale the year following. But i don't like that much to be the top, i am born to be a bottom. Also whit well endowed shemales i prefer to be the bottom, i do the top only whit the submissive small endowed ones. Sometimes i tried the strapon whit some of my ex girlfriends, it's a very great experience... i hope to try it again and soon!

I was 15 and my best friend with a 7 inch cock rode me hard, then he sucked me for a long time. Big long cock in the ass in very nice.

Two weeks ago with my wife. I was pretty excited she wanted to try it(she's got a JUICY ass ), and I couldn't wait. After playing around, I got back there and shoved it in. Unfortunatly, it hurt her and she didn't want to continue. It was cool, though, she let me put my dick in between her asscheeks and mainly jack myself off with her ass . So that was pretty cool, obviously.

I'm a 100% bottom so I've never had a topping experience, but my first time taking...well, I don't want to bring the funny mood of the room down but I was raped.

I had just turned 18 and I was ready to see what the world of cruising was like. I went to my local porn shop that also had an arcade. The first dude I saw in there caught my attention; He was latin, muscular and stroking a fat cock through his sweats. We immediately went into a booth to hook up.

Things went super fast and the next thing I know he's trying to push his cock into me. I freaked out and tried to stop him, but when he felt my resistance, he grabbed me tight and forced through my pucker.

It hurt so fucking bad and I felt like shit the entire time (shich was really only a couple of seconds because I was so tight) and he came inside me.

I immediately ran out and cried in my car in the parking lot. I got tested later and was relieved that I was HIV/AIDS negative still, but it was the scarriest thing that ever happened to me.

I swear on everything that I didn't make that experience up...it truly happened to me. Luckily, the only side-effect to my traumatic experience is the fact that I love to have sex all the time now...which is weird, but whatever!

I consider i did not have it yet although when was having very fast doggie by "mistake" he penetrated me without not preparation whatsoever... it was just very terrible and traumatic i felt i was raped...not joking.

But i know i have sensitive anus...and one day who knows will try it when feel safe, because im very protective of anything larger than a thin tip of a finger going inside ...

When did you first have anal sex?

In my mid-teens – I used to hang out with a group of guys. We were discovering our sexuality together. We would masturbate in each others company, explore mutual masturbation and would suck each other off. I was enjoying my sexual experiences so it was no surprise that I wanted to try new experiences.

It wasn’t too long before we engaged in anal sex. One night at a party I had too much to drink and slept over at my mate’s house. I just stripped off and slipped into his bed. I felt his hand on my cock and despite feeling worse for wear I soon got aroused and had an erection. He continued to caress me and got to turn on my side. I hindsight I probably knew what he was going to do and when his cock hovered over my arse hole I just let events unfold. Being relaxed through the effects of the alcohol he was able to penetrate me without too much discomfort. I enjoyed being fucked anally and still do.

I topped at 17. Bottomed at 21.

i was 16 with my first lover, soon after we starting having sex...we wanted to try everything we'd heard..

topped at 11 (in scouts how cheesey is that). Never bottomed, had one guy try at 19 but was a bit of a schock and my head went back that fast i broke his nose Wouldnt mind trying it sometime tho xx

i have never bottomed. first time topping was at a bible school in africa. on a mountain in lesotho. it was a six month course so i had six monhs of absolute bliss.
would i like to bottom....there were a few guy friends in the past, whom i would have loved, but all were str8 and the convincing arguments tired me out!!

Technically my first time was on my 21st birthday. I picked up this hot 40 year old at a bar and we screwed around a bit. He was VERY big, though, so it hurt quite a bit.

My first time ACTUALLY having a guy cum in me was a few months later. It was really, really hot. It took a lot of lube, but I noticed that after he got the first few inches in, it didn't hurt much at all.