I was 18 when I tried it with my ex. A very painful experience seeing as he decided not to use lube both times.

the first time i was successfull was at 22 with my husband. we were both pretty waisted so its a little bit fuzzy.. it was very enjoyable thou. i remember that . but the first time i tried was maybe 18. at 18 (ggrrr f***en bastered) the only reason why he got off of me was because i started to scream at the top of my lungs. told him he was hurting me. asked him several times to get off and he would. so i started screaming. thats how he made me lose my virginity aswell. told him he was hurting me and that i wasnt at all enjoying it and he refused t get off me. i should have sceamed then too.

Solo- maybe 16 or 17. It would have been with a candle or something similar, on my own. With my girlfriend- only a few months back

Solo when I was younger, 18 maybe. With a partner a little later around 21 or 22, can't remember exactly.

I was 21.

My boyfriend at the time (now ex) and I had been talking about it for a while; he was actually leery about the idea and I spent a long time (a matter of months, probably) trying to make him feel more comfortable with it. Once it did happen, we went slow and both enjoyed it.

Never did any solo play in this area until after I figured out how much I enjoyed it. We weren't married yet and had only just recently started having sex when he asked if I thought it was something I might be interested in. I told him that I wasn't opposed to at least trying for him if he wanted to and he lit up like a candle and sprinted out the door hollering "I'll be right back... don't move!" Apparently it was something he had thought about and researched fully before asking because when he came back, he had nail clippers, my nail file, finger cots and lube! I gave him a manicure and we hopped in the shower for some foreplay. Got out and there was more foreplay before he rolled on a finger cot and lubed up. Like with most of our sex, it was fun and silly and we just had a good time with it. I took the finger like a champ and when he flipped me over, before he went any further he asked if I was still down with the idea and away we went. It's been over 10 years now and I still very much enjoy anal sex. Sometimes even prefer it or ask for it instead of vaginal sex. I have also figured out that I am a true fan of double penetration. Amazingly mind blowing orgasms.

Haha guess I was old...I was 23 the first time I tried it.

I believe I was 18 when I first tried it. Fairly young for something somewhat painful.

I voted for 16-17, because since 15 is not on there. I was 15.

My first time was on Valentine's Day with a random boy I started making out with at the club. Ooooh drunken times ^.^

I hated it. I tried it again a couple years later with a different bf (who is now my hubby). Hated it still...it was horrible. Of course we didn't have any idea what we were doing. He just went at it like you see in porn....so that explains that. I actually didn't have successful pleasurable anal till this year. And that was after a long period of warming up to the idea again and a good bout of foreplay. Now we plan on anal about once a week

It was the day after my 21st birthday and a complete accident. We were spooning and passed out from all the booze and he slid in the wrong hole. We've only been successful twice since then. I'm trying to get into it more.

I was 19, and I did not enjoy it at all. He forced me to do it, after a few years of begging, even though I kept saying no.

I was 14, and I've been having anal sex fairly regularly ever since. I was my current boyfriend's first anal sex, he was 22 at the time.

I didn't even know that heterosexual couples enjoyed anal until 2 months ago, and I'm 40!!!!! We are just beginning to explore this area... an area never before explored after almost 20 years married! I'm so excited to hopefully soon... lose my anal virginity to my husband... who unfortunately, didn't get the vaginal virginity due also to a creep of a boyfriend just before I met him. Yay for new beginnings!!!

Wanted to put my post in this new updated thread

How it was for me, plus a few of my friends who also like it, and a cousin of mine who is a total backdoor betty like me, is that the thing that seems to make the difference is attraction to the idea of anal prior to taking your first plunge. The idea of sex in my butt instead of my pussy made me very horny from the time I was in my early teens. When I'd be around a boy or man I felt an attraction to, the image in my mind was usually him giving me anal sex. Anal porn really excited me too, and I'd also been masturbating with my vibrator anally before my first time. So maybe that helped the sensation not feel so strange my first time I did it.

I was 16 when I got to where I knew I really had to try it and realized my boyfriend at the time was not the one I wanted to do it with. He seemed too---something. I loved him, just knew he wasn't the one to handle my special request. Opportunity finally knocked and out of desperation I asked a friend of my friend's older brother if he would to do it to me while we were at this wedding reception. I lost it belly down, dress up in the backseat of his car out in the parking lot. He was pretty good actually and was rougher than I expected. Not like mean. But I had asked for it, he drove it home and my rear really took it good. It hurt when he pumped deep but I liked it, and then that pressure was gone and it turned to pleasure. There is that element to it. I didn't technically orgasm but I think if we weren't all crammed into the car I would have. By the following summer began seeing an older guy who really opened me up and took it to the next level for me. To this day I still do it way more than I have vaginal sex.

I first started fingering myself around 13, and used my first toy at 16. I then first had anal sex at 19.

Hurt like hell, and I still dont like anything big going in there.

Bf and I were about 17 we actually tried anal before vaginal for fear of the whole pregnancy thing. It was nice he was patient and it was an over all good experience that we still enjoy today

I was 18 the first time i tried it. My ex and I had been partying so we were quite drunk when it happened, but I really enjoyed it. Ever since then it hasn't been the same though. Every time I try it just really hurts.

Technically speaking I was 15.

I was 18.....and was a bad experience for me. It took me forever to try it again

Just last year actually.

19 or 20.

18 it hurt like hell too!