First Anal [f/m]

This one is by request ;)

This memory is a little fuzzy (it's been a long while) but as a milestone in my sexual history most of the important snapshots are still there.

It was the summer between sophomore and junior year. (NOTE – seriously, all my BEST stories seem to take place during summer, I should wear a chastity bathing suit). I was 16 and newly single. My ex-boyfriend and I had a typical, tumultuous teenage relationship (that would go on/off again for the next 7 years or so, far too long). My friend and I went to a summer festival concert and ran into one of my ex's best friends, Benji (not his real name). Ben had just graduated and was headed off to an Ivy League school for college. He was already a cocky motherfucker but the Ivy League prestige definitely put a new spring in his step. As did his newly pierced tongue.

We chatted a bit and went our separate ways but agreed to chat later over AIM, keep in touch, etc etc. I remember my friend noting that he'd been flirting with me but I shrugged it off, reminded her that Ben flirts with everyone. I mean, the guy even had a 69 in his screenname. Later that evening though when she was sleeping over I started IMing with him and he was indeed flirting. I can't remember if we had a conversation about deference to my ex or not. If we did I'm sure Ben's answer was "fuck that" or "who cares" or at least "no one has to know." He was leaving for school anyway and we'd always had chemistry. I was curious. And honestly I was probably pissed at my ex too and saw this as an evil way to get revenge.

Ben and I continued chatting and calling over the next few days and we made plans to go to the movies one night. We'd gone out lots of times before but always with groups (including my ex) but I tried to keep it nonchalant, friendly, we were just going to hang out…

Ben picked me up and we went to the theater to get tickets. We had some free time before so we decided to go for a walk around the plaza the theater was in. This part is still very vivid in my mind (15 years later) – I must have teased him again about the tongue ring or made some curious comment about it. Before I knew it my back was pressed up against the brick of the outside theater wall and his tongue was in my mouth. I'd been with three guys up to this point – not a one with the confidence or assertiveness that Ben displayed. Clearly all I needed to flip my freak switch was a man with a plan (and the tongue piercing didn't hurt either – I'd get my own two years later). The feeling of Ben's hands roaming my body, holding me there, taking control of the moment was intoxicating. It made me feel sexy, wanted, feminine. I knew I was in for trouble.

I can't remember if we actually watched the movie or not. If we did I'm sure it was just to take advantage of each other in a dark room. After we got in his car and found a quiet, secluded spot somewhere. We clearly both had sex on the brain.

The foreplay and the initial sex are fuzzy memories to me, I just have flashes like snapshots in my mind of us sweating in the backseat of his car. Of that piercing catching my clit in just the right spot and driving me wild, making me cock hungry. I wish I had my diary from back then. I know I wrote out the whole thing in intricate detail, I remember reading it to get myself off once in a while. But I do remember feeling a sense of relief, a sense of belonging in finding someone as passionate about sex as I was, as open and aggressive and raw as I wanted to be.

Which is why while I was riding him, bouncing on his dick in the backseat of his car, mind trailing to think of how many times I'd hooked up with my ex on this same upholstery and how ridiculously naughty THAT was, I wasn't very taken aback when he asked if I wanted to try something. I was wide-eyed and lustful and down for anything he was willing to give me. His hands reached for my ass and squeezed my cheeks, lifting me up and off his dick. He spit, making sure his cock was well lubed and gently guided me back down, but at a different angle. I felt a lot of pressure and then suddenly fuller than I'd ever felt before. Stretched. Invaded – but in a good way.

In my mind I figured everything about this event was already taboo – my ex's friend, casual sex (oh no!) – that I might as well fucking go for it. As soon as I got over the initial adjustment I began riding his dick slowly with my ass, enjoying how much more I could feel each and every twitch and thrust. He reached between us and rubbed my clit which only made me want more. I remember wondering if I could cum from anal, was that possible? (oh it is dears, of course it is) though this first time I would probably have to credit his fingers for the orgasm. He came too and I admitted to him that was a first for me. If I'm not mistaken, it actually was a first for him too (though it took him 10 or 15 years to admit that to me).

This was really one of the formative events in my life – after that night I accepted that I was a sexual being and wouldn't apologize for it. Ben and I had lots of sex after that, over the years, whenever the opportunity presented itself. We're still good friends but we don't have sex anymore as we're both in relationships. He checks out my reddit posts from time to time though, so Benji my dear, if I've missed anything important, reveal yourself and let us know in the comments :)

Source: reddit.com/r/gonewildstories/comments/3b8vwf/first_anal_fm