How I missed a golden opportunity
August 8th, 2006 by acrylic
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.
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Acrylic you moron! I hope you atoned for your previous shortcomings later in life. Surprisingly few girls are up for it at that age, you had the perfect partner!
Ha ha! Trust me, I’m still kicking myself to this day over that blunder. But it felt good to get it off my chest, as I’ve never really talked about it to anybody. Hopefully, others can learn from my idiotic mistakes!
I think that I would probably have thought the same. While I would loved to give it to her in the ass, I would not even entertain the thought of her wanting to boff me in the ass, no sir. On the other hand, it is said that this goes on in prison with completely heterosexual men, and they go back to regular sex lives after their release. Maybe she only wanted you inside her, and not vice-versa. Still, I would have had to think about that one for awhile.
acrylc … You can not be too “Hard-On” yourself (Smile) afterall. You had an experience of a lifetime at a very young age with a Ladyboy. Something that some people will never experience at all.
You were very open-minded as a youngster to even try the experience. I give you a great deal of credit for that. We live and we learn … and try to enjoy ourselves along the way.
The Ice Man.