Age When You First Had Anal?

General discussion of the anal only lifestyle. If it doesn't fit elsewhere or isn't a personal comment or question, it probably goes here.
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Re: Age When You First Had Anal?

Post by BackdoorDeliveryman3 » Mon Jan 16, 2017 9:40 am

Although I was a big fan of anal sex and never had much luck with meeting a woman who would be happy to take it in her back door until I was 29.

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Re: Age When You First Had Anal?

Post by cassandra » Sun Feb 19, 2017 6:48 am


My first time was at 14. I'd been going out with my boyfriend for almost a year. He was 19 and lived about a half hour drive away, so we rarely saw each other during the week. He took my virginity early on, and after that he wanted sex every weekend. I wasn't on the pill then so he had to wear a rubber, and sometimes I'd be on my monthly so he had to make do with me sucking him off. Then one day he said he had forgotten to buy any rubbers. I offered to go down on him but he said we could try it like gays do. I was so in love with him I would have done anything. He wasn't very gentle so it hurt like hell that first time and left me sore afterward, but once the pain had gone I started playing with my ass in the shower. Over a few weeks I learned to relax and could soon get the handle of a brush inside. I practiced with other things too and using different creams as lube. The next time he wanted to fuck me in the ass it was easier and it became a regular thing during my monthly or when he'd "forgotten" to bring a rubber. At 15 I was put on the pill to help with painful periods that were interfering with my schoolwork, but I'd grown to enjoy anal by then and would ask him for it when I was in the mood.


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Re: Age When You First Had Anal?

Post by aredeejay3001 » Tue Jan 01, 2019 8:15 pm

I was 20 when I first had anal sex, with my then girlfriend of three years. She had graduated from our college one year ahead of me and was visiting me for a weekend in the fall of my senior year, so we were eager to get down to business. While we were having sex on the first day of her visit, we tried a rear entry position where I was seated with my back against the wall and she was leaning forward while sliding up and down on me. I was semi-erect, so she was able to bend really far forward and hence it offered her ass to me. I wound up working both my thumbs into her ass as we had sex, which was a first for us.

The next day we decided to try anal and I took her from behind as she stood bent over a chair, eventually coming inside while deep in her ass. It was a great experience for both of us.

Our relationship was burning bright -- almost too bright -- and a visit to her the next month revealed that we were actually heading in different directions, and we broke up. That first anal sex experience wound up being one of the last times we had sex (if not the last time.)

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Re: Age When You First Had Anal?

Post by Hitman1386 » Wed Jan 02, 2019 8:37 am

When I was 17. My first serious girlfriend was scared of getting pregnant. She would do everything but vaginal. She was still a vaginal virgin when we broke up.

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Re: Age When You First Had Anal?

Post by Sky » Sun Jan 27, 2019 6:38 pm

Can't say that. Too young
Any how First it was weird then a small pain after that until now never felt any pain. Or uncomfortable. But never had anal if i'm not ready. I think you all know what I mean.

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Re: Age When You First Had Anal?

Post by GreenEye » Wed Jan 30, 2019 9:11 am

I was around 19 years old. I had a girlfriend that loved to have lots of sex. We were having sex one day at my parents house in my waterbed in the missionary position.We were going about it for a little while when she reached down and grabbed me penis and directed it towards her anus and then pulled me into her just using the wetness from her vagina for lubrication. I was so excited about what was taking place. I just went slow until she told me to go a little faster. I eventually came inside of her and we both just enjoyed what had just taken place. I am sure she had a lot of practice in anal sex. I might have had anal one more time with her before we parted ways.

When I was about 8-9 years old is when I became self aware of the pleasure of self anal play. I would use small household stuff lubricated with either KY or vaseline. I would just like the feeling of the fullness. When I was around 22 and in a marriage I purchased a dildo for use when I had regular vaginal sex on my wife. I found myself using the dildo more on myself than with sex with my wife. Over the years I had several different ones to include vibrators. At the age of 34 I was in a situation where I was very bi curious. I had a male instructor (it was a class for different diagnostic evaluations using ultrasound) that during some private tutoring he began complimenting me on my body. Understand that I was usually in shorts and shirtless. One day he was showing me how to trace various arteries in the legs and began his moves on me by masturbating me and doing oral. I welcomed the attention and did not stop him. We did this a few times when we met. One day he started off the same but this time he went further. I was on my back while he was pleasuring me orally and then he moved up to my chest. He was nude and then he placed his erection against my hole after putting some spit on himself. I asked him for some of the ultrasound gel and he lubed himself and me. Because of my years of self play he pushed into me without any pain. The intensity of what was happening to me was mind blowing. He was stimulating my prostate with each thrust. I began to feel this tingle in my groin and all over my body. My penis began to shoot cum as he was thrusting in me and I was having my first anal orgasm from a penis. I almost saw stars and screamed. My ass and prostate pulsing was a real pleasure for him. He then then says I am going to cum. I told him to cum in me. I could feel the flood of him deep in me, he was a very heavy cummer and had the ability to shoot his cum a great distance. I was hooked on this new pleasure. We cleaned up and finished the class. We met two other times and had bareback anal. We ended up parting ways because of his job.
A few months later I met a guy that would introduce to me to another form of anal. He was 100% bottom. He could not get an erection so our sex was AO. The change for me of being the top was wonderful. He was sexually liberating for gay sex. Being a top to a guy was a big difference than with a woman. We eventually parted ways as I wanted to explore switching roles as the bottom and top. I enjoy anal sex but also love vaginal sex as well. Anal to me will always have a place in my sexual wants. I still do some self anal play for orgasms over penile play for orgasm.

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Re: Age When You First Had Anal?

Post by amaizeg » Fri Mar 01, 2019 11:29 am

20, my girlfriend was 19. It was the first time for both of us.

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Re: Age When You First Had Anal?

Post by zarafan » Sun Mar 03, 2019 3:40 am

I was also 19 the first time I had anal, with my first serious (sexual) girlfriend; we were both at university. We had been dating for about two weeks or so, and in keeping with our age and the newness of our relationship, we were fucking like rabbits. Oh, why does sex ever have to change from that moment?! One day she dropped in at my dorm room--either from the library or from her job--not intending to do anything but say hello. To our respective delight, the hello turned into a characteristically steamy make-out session with the inevitable consequence that we both wanted to have sex instantly and infinitely! For better or worse (spoiler alert for fans of anal: for MUCH, MUCH better!!!) she had not brought her birth control device (diaphragm) and I didn't own any condoms. As luck would have it, she had a few nights earlier brought a bottle of baby oil over for an "erotic message," and she suggested we make use of it in order to have sex "the other way" (our subsequent euphemism of choice). Sex with your first partner is an experience of continuous revelation, but this was anotha' furtha!

Anal sex became a regular feature of our relationship from that point; for some reason, we stopped using the baby oil--she decided she got wet enough from our foreplay that she didn't need it--which on reflection nowadays was at least a strategic error, since for many years I would try to have anal sex with other partners without lubrication, with predictably frustrating results for me and vexing results for them. (I've since learned that lesson: sorry, partners!!) But anal sex with her was always effortless, and I remember vividly how once coming back to my room from class, where she had been studying after spending the night, I began to undress her and immediately took her ass: it was a spontaneous decision and I can't remember if it was preceded by either discussion or demands, but it's one of the most intense sexual experiences of my life.

As time went by, for reasons I can only conjecture, I began to think that the prominence I had accorded to anal sex was somehow wrong: that it was somehow exploitative of my partner, that she wasn't really enjoying it or couldn't enjoy it, that "real," adult men shouldn't desire anal sex. For many months accordingly, we settled into a horribly pedestrian routine of the most routine, formulaic, vaginal-only sex. I still don't know why I did that; certainly not at her prompting. A few magical times in the twilight of our relationship we returned to anal, and each time was better than the previous one, but as is common in experiences of first love, we had already begun drifting apart and realized our lives would head in separate directions.

I have a lot of regrets about that relationship; all of them predicated on the foolishness and blindness of a young person who didn't recognize how extraordinary it is to find a partner so sexually compatible with me: I honestly thought that every woman would be just as accommodating, energetic, and enthusiastic about sex as she was. (BIG miscalculation!!!) I hope I've grown since then, both in my understanding of sexuality and my appreciation of my partners. But if some of my other partners taught me how fraught and difficult an intimate relationship could be--and I presumably taught them the same--I can at least credit her for teaching me all that was and can be wonderful about sex, intimacy, and love.

Fast forward about twenty years and we have gotten back in touch; she's married now and living a life quite different than either of us would have expected. But I'm glad that we are friends again and we are able to share at least part of our experience of the world with one another again. And I'm grateful that I've been able to admit to her, even belatedly, that you can never be truly wise and in love at the same time. I hope she understands that as well as I do.

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Re: Age When You First Had Anal?

Post by omarp » Sun Mar 03, 2019 1:29 pm

Pretty early in secondary school. I went to a catholic school so a lot of the girls that ran in my friendship circles were all very much no PIV. So that ended up in Only anal sex.

I guess that where it stemmed from for me.

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Re: Age When You First Had Anal?

Post by reinors » Tue Mar 05, 2019 4:25 am

Ihad first anal in 19 years old. It was in massage parlor. My friend and I was in Prague in business trip. So, in free time I went to one massage parlor here where I had session of erotic massage for men. Also the great plus for visitors are opportunities to choose different types of erotic massages.

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