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Unforgettable First Time

I used to visit a transsexual, who normally sees only younger guys but made an exception for me. She used to lay me on the bed and blindfold me, then tie my cock tight with a silk ribbon. She would put a small vibrator in my ass, then lightly thrash me with a soft leather whip before sticking a larger dildo in my ass and leading me up to sit on a stool. Then she would masturbate me with lube-covered hands until my cum spurted all over the floor.

I would also visit an older male, the flatmate of an ex-girlfriend. I would go over to watch a movie, get dressed up, then relax on the couch. After a while, I’d play with an anal probe until fully turned on. Then he would come over and suck me before I got him to fuck my ass with a big dildo while I slowly masturbated. Once, while I was on my knees over the couch, he actually fucked me and came in my ass. I wasn't sure what was happening because his dick isn't that big. I really let go at these sessions and moan like crazy with the thrusts of the big dildo

I still consider myself a straight man. I have never fucked a guy. And I had never been fucked by one, except for the time I just mentioned and the one I am going to tell you about.

I only once shared my fetishes with a woman - a past girlfriend. She was an older black woman, very pretty, with large tits and a cute ass. She was incredibly strong physically. Once she got to know me, I allowed her to see me dressed in lingerie. She suggested I shave my legs. So I did shave my cock, balls and legs. I remember how much better I looked in stockings with shaved legs. But I don't think it's worth the trouble to keep that look!

One day we bought me a leather cock strap, the kind that has a central bar strap to split the balls. I remember they had three sizes and I picked the middle one, although the largest size probably would have been best. Wearing it, my cock swelled like crazy with veins popping from the sides, the head swollen and shining, red with a hard ridge of dark purple. We attached a chain to it and she walked me around on all fours like a lingerie-wearing dog, kicking my ass and yanking the chain brutally. Eventually she lay me down and sucked me before I fucked her hard.

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