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When everyone was asleep I dressed in stockings, garter and my favorite panties. I pulled a t-shirt tight exposing my belly and looked at myself in the mirror. I have a thin build, long legs and kind of a perky ass. What very little hair I have I've shaved to make my dressing experiences feel more feminine. I slowly rubbed my hands on chest and ass, squeezing my cheeks and spreading them just enough to see my hole. I couldn't stop thinking about what Bob said and what this would really feel like if it were him doing this. I positioned my dildo so I could ride it watching my limp cock bounce around and then eventually becoming hard, I was whispering "yes Bob, do me" "mmmm yess baby take me" and eventually spurting all over my bedroom floor, imagining Bob cumming in me as well.A few days past, and it was Friday the company Holiday party. My sister dropped me off at the party and told me to give her a call when I needed to her to pick me up. Joey was already there with a big smile, so we. I quickly exited the bathroom. A few minutes later he came out. He appeared ashamed of what he had done and being caught. "It's nothing to be ashamed of, Jake," I told him. "I do it all the time." There was a long silece before he spoke. "Is it supposed to hurt so much when I do it?" he asked. "Have you been doing it very long?" "A couple months now, I guess." "Can I see your cock?" His eyes, which were turned shyly down to the floor, suddenly looked over at me A long whle passed before he finally pulled the draw string of his pajama pants which sent them down his legs and into a soft bundle around his feet. Instinctively his hands moved over his penis. I gently parted his hands. The penis dangled there between his legs, very red and sore looking. "Is it all right?" he asked. "Yes. You're just being a little rough on it. You have to stroke it gently. It should be a pleasurable experience--not painful. Do you come?" "Sometimes. It hurts so bad sometimes I just stop." I.
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