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So we didn’t have a great deal of time alone together. In seven weeks of “dating” we had kissed a few times and engaged in some light petting over our clothes.The week before Prom we both lost our virginity in the backseat of my Mustang. I was not expecting it. As it turned out, it was more awkward than memorable; I never did get positioned to go more than half way inside of her. But we had done the deed. She even bled, so it was “official”. I was so nervous about being caught that I didn’t even cum, and it was clear she didn’t enjoy it that much either. But we assured one another that Prom night would be better. Both our parents thought we would be at an all-night lock-in event. We had a picnic shelter area at a nearby park picked out. I planned to bring a soft blanket and some candles.Prom night came and Caitlyn looked smoking hot. The long, backless, black dress emphasized her lean body. It was slit high up one leg, where, if she moved just right, I could see her creamy thigh. It looked like it belonged on someone else's body. I admit I was curious (you wouldn't be?), but tried to be discrete and not stare. I noted that he was tan all over and thought "who wouldn't hang out at nude beaches with a dick like that?"Let me go back a little before I continue. I am a straight man, in my early thirties. Women tell me I'm good looking. I'm 6'4'', muscular, weigh 200 and work out and run very regularly to keep myself in top condition. I was a pretty good college basketball player and still compete. I travel about once every two months on my job and generally have "good luck" with women, with a couple of long-term relationships and dozens of short-term sexual adventures, including many one night romances when I am on the road. I haven't settled down yet mainly because I do still enjoy these adventures so much and I'm not ready to be tied down to one woman.That night at the O'Hare Airport Sheraton in Chicago I'd had a very routine day of meetings. I was flying out.
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