Well, as exar commented before, it pays to be open-minded. A perfect example was the golden opportunity I missed back in High School. That opportunity was to go all the way with my LB girlfriend…all the way inside her tight little asshole.
We were talking on the phone one night, and she told me she wanted me inside her, and by inside, she meant: her ass. This was in the days before most people had wireless phones in the house, so I was stuck talking in the kitchen, with my mom nearby cooking up some food!
Needless to say, it was difficult to talk about such things under the circumstances, but I managed to disguise my language so our subject matter would be incomprehensible.
She told me that she wanted me to fuck her in the ass, and when I hesitated, assured me that it’s no big deal, cause straight people do it too.
I remember she even told me how she heard that back in the 50′s lots of straight couples had anal sex as a method of birth control. Whether or not this is true, I can’t be sure, but somehow, that memory from our conversation sticks out in my mind.
I used the lame excuse that I didn’t want to hurt her. But I remember her describing everything in detail. She read a lot of magazines, and told me that she already had lube at the house. If we used plenty if it, it would feel good for both of us cause her asshole was tight, so the sensation would be more intense than oral sex.
Was I afraid of anal sex? Hell no. In fact, like many men, I had fantasized about it often. But my fantasies always included women, not Ladyboys. Also, my mom was pretty closed-minded when it came to gay people, so the fact we were talking about it in her presence may have added to my guilty feelings.
I guess you could say I was still a little brainwashed into thinking that somehow, if I crossed the line, and had anal sex with a guy, even if it was with a beautiful Ladyboy, that this would make me gay. Another thing I was worried about was that if I fucked her asshole, that she might want to fuck mine too, and I just wasn’t ready for that yet.
I know it sounds stupid, and some of you are probably wondering why I was willing to give and receive oral sex with her, but not do anal. Well, the answer’s quite simple really:
Because I was a closed-minded fool!!!
To this day, I still regret it because I never did get another chance to have my dick inside her cute little ass.
Continue…
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