Since I have been old enough to jerk off, I have been attracted to exceptionally buff and athletic women. The first time I ejaculated, I was fourteen and I was watching women’s gymnastics in the summer Olympics on television. Since then, I have desired a non-stereotypically-feminine woman. As my sexual development progressed, I discovered that I wanted such a woman to sodomize me—to fuck me in the ass with a strap-on. I have thought long and hard about this. Buff, athletic women are the most amazing, sexy creatures on the planet.
The desire has remained totally unsatisfied throughout my life. Recently, though, I was able, through some miracle, to go on a couple of dates with this girl who is on the diving team of my university. She is my ideal woman, and I really like her, but I’m afraid if I ask her for anal sex, I will lose a relationship with the sexiest, coolest, sweetest girl I have ever had the chance to be involved with. Help! How do I find out if she would be into anal sex with me? And, if not, how in the world will I ever find another as buff and beautiful as she is that might just be into anal sex with me? This girl is amazing, and I don’t want to lose her, even if that means sticking my thumb up my ass while thinking about her, and settling for strictly vanilla sex with the girl of my dreams.
—Buff Girls Rock My World
Well, it sounds like you really like athletic, assertive, maybe even butch, heterosexual women. I commend you for figuring out the unique type of person that floats your boat (and obviously gets your dick hard). As for seeing if she’s into fucking you in the ass, well, I think you need to take the plunge and ask her. I understand that you don’t want to lose her, but you also want to have your anal desires fulfilled, and those anal desires seem pretty fucking strong to me. So, approach her honestly and in a non-confrontational way, and tell her what you want. Hopefully, she will make all your dreams come true, and strap it on.