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.
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.)
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.
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.
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.
I guess that where it stemmed from for me.