Sex with Another Man – The Best Sex of My Life

The first porn I ever saw was when I was like 15 or so (back in the 80s). It was a VHS of some story involving a ship’s captain, etc., you know how old porn is. The ship’s captain was black, and there was a scene where he had anal sex with this blond woman, and she was really into it and it was really hot. I had been under the impression that anal sex “hurt”, but my immediate thought was, well if anal sex feels good to women, why wouldn’t it feel good to men too, it’s basically all the same down there. So, I began masturbating anally at that point, fingering myself or sometimes using objects when I masturbated.

This went on for years, and I didn’t really think much about it. A couple of my girlfriends fingered me when giving my blowjobs, which I was very into, etc.

At around 23 or so I hooked up with this older women, in her 40s, and we were together for 2 years. Her prior boyfriend was bi, she told me. She was a big slut, which I liked. We had a great relationship, but she had sex with other guys too, but told me early on that she didn’t want me to have sex with anyone else, which I was fine with. In fact we had a threesome with another guy (no guy on guy), and I watched her with another guy once, but really we were together almost every week. We considered ourselves boyfriend/girlfriend, etc. I actually moved in with her for about 9 months at one point.

Anyway, we talked about sex a lot and fantasized a lot, and the issue of me liking anal came up, and she was very into it. I won’t go into details here because it’s not the point, but we got some dildos and eventually she started fucking me with a strapon on a pretty regular basis. When I was living with her, probably 2 or 3 times a month she’d fuck me with a strapon. One time I cross dressed with her (which was also very hot, but a different story).

She would tell me how much better a real cock feels than a toy and that she’d love to watch me with another guy, etc. and we fantasized about that a lot. However, it never happened.

I eventually bought a house and moved out and we kind of broke up, basically just saying that we needed to move on and see other people because we knew, due to the age difference, it wasn’t going to go anywhere long term, etc., We still saw each other from time to time, but now I was “free” to see other people.

So, there was this black guy I ran into a lot at night clubs, my age, he looked like a GQ model. He was always very well dressed, etc., and he had kind of a “gay” vibe to him, though I often saw him with women. We made small talk a lot when we saw each other out. One night, I don’t remember exactly how, (I was drunk no doubt) we broached the topic of sexuality and he said he was bi and I said I was interested, but never done anything, etc. TMaLSS, he gave me his number and he came other one night and we made out and 69ed, and started getting into it, but he also wanted to be “on bottom”, something I hadn’t anticipated. So anyway, it kind of fizzled and we ended up just watching each other jack off.


So, after that I was horny for cock and I had kind of broken the barrier and was determined to get fucked. I went on-line (this was around 2003) and found a married back guy to hook up with. He wanted me to cross dress for him, which I was happy to do.

So I went out and got makeup and lingerie and fishnets, etc. Oh, BTW, I had (and still have) long strawberry blond hair. I shaved pretty much everything and put everything on with pigtails and looked honestly like a very hot chick and was very horny for this to happen. I was 6’0″ about 160lbs at the time (I’m about 180lbs now). It was a black lace slip, with garter belt holding up fishnet thigh highs and a black thong.

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