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.
THE GOOD PART:
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.
We made arrangements for him to come over one afternoon during the week (I was about 25 at the time and had recently quit my job to move back to my home state). I got ready again and was super anxious.
He was in his 40s, shaved head, with a mustache, about 6’3″, 225. Not toned, but a big strong guy.
I was immediately weak in the knees when I opened the door. He came in and I had my blinds all closed, etc. and he was very “affectionate” right away. He was like, “Mmmm, you are a very pretty little girl,” and he like caressed me kissed me, which took me by surprise. I dropped to my knees and started undoing his pants and pulled them down, revealing his huge cock. I had seen pictures, but in real life it was stunning. It was probably about 10″ and as thick as my wrist.
I rubbed it all over my face and began sucking it. He took off his clothes all the way and then moved to the couch. He sat down and I got on my knees between his legs and continued sucking him as he caressed me and told me I was a pretty girl, etc. Then he kind of gently motioned me up onto his lap, straddling him.
He pulled my panties to the side, revealing my cock, which was rock hard. BTW I have a large cock myself, about 8″. He was like, “Mmmmm, you’ve got a big cock for a white girl, I like that,” and smiled at me. He rubbed it a little, but then pulled his cock up behind me and positioned it on my ass. He then got some lube out of his pocket (pants were sitting on the couch) and lubed up his cock and had me sit on it again. I slowly bounced up and down on it and eventually worked it into me and began riding it up and down as he held my waist.
After a few minutes of this he had me get off and lay on the couch next to him, then he got up and spread my legs and me slid his cock into me missionary style, with him holding my legs up. This was so hot since I could see his cock fucking me. After a few minutes of that he had me get up Rocky(D)gy style on the couch and he fucked me like that for a while, talking dirty all the while.
Then I suggested we go to my bedroom, where he fucked me on my bed in about 10 different positions for 30 minutes or so. I had full length mirrored doors on the closet doors in my bedroom, kind of around a corner from my bed. He saw those and told me to get on the floor in front of them. I did, Rocky(D)gy style, and then I’ll never forget when I looked in the mirror and it was pretty shocking. I looked at myself and I was all dolled up and looking like a hot chick and I could he him behind me fucking my ass and it was so hot, I just stared at myself in the mirror and then started going crazy saying stuff like, “Oh fuck I love your cock. Oh my god you make my pussy feel so good. I love taking your big black cock. Oh fuck I love being your white whore. Oh my god I fucking love taking cock in my pussy so much, I’ll do anything for your big cock.”, etc., etc. And he was getting really into it too with dirty talk. Then he had me flip over and he pushed my knees up to my ears and started pounding the fuck out of my ass, telling me what a good whore I was and how he wanted to use me again, etc. Then he got up and I quickly got on my knees and opened my mouth and he came a bucket-load all over my face and in my mouth. I swallowed his cum, and then put his cock in my mouth and we looked into the mirror together. He was caressing my hair and I was just looking at myself with his big black cock in my mouth and cum all over my pretty face, and it was soooo fucking hot.
He went and got cleaned up and I did as well in the other bathroom, and he kissed me good by and said he wanted to do it again.
He came over again about 2 weeks later and it went much the same way. About 3 weeks after that I moved back home, and we never contacted each other again, and I’ve never done anything with another guy again. BTW, I’ve been with about 20 women in my life.
Now, I really want to tell my wife about this. I think she would be okay with it, and would think it was hot, but I’m still apprehensive, and it’s not really easy to bring up. My wife has fucked me with a dildo a few times and she’s into that, but not super into it. She’s initiated it a few times though, but we’ve only done it 4 or 5 times aver 7 years.