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This is the story of how I first became acquainted with gay sex. Although I had never thought of myself as gay, I do remember experiencing a curiosity about cross-dressing and gay sex. However, social constraints caused me to repress this for a while. Once, my whole family went out for dinner and so I was completely alone in the house for the night. I had this funny idea to dress up like a woman, to see how it felt. So I went to my sister's room, and fetched some of her underwear; tight, and a bra. Now I was short, fairly muscular, about 5'10, 120 pounds, but with an ass as firm and sexy as any female model's. My legs are also pretty long and well shaped, sexy, despite my short stature.

I took of my clothes and first tried to put on her underwear. It fit fairly well, except that it was a little tight around the ass. I then fit on her bra, but, although the straps were tight around my upper thorax, enough to leave their marks later on, there was no way I could fill those DD cups up. So I fetched a couple of balloons, which I judged were about flesh color, filled them up with water, minding that they were equally sized, and I put them into the bra. They simulated real tits fairly well. I then put a black evening dress on me, some panties, heels, a long flowing- haired wig, black, to match my hair color, and some lipstick. As soon as I looked in the mirror, I got a really hard hard-on, which combined with the tightness of the underwear around my cock and balls, started causing some weird but infinitely pleasurable sensations along my rod. I had masturbated before, but this ...

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