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I did as instructed even though I really wanted to stroke myself. Ann came back with an arm-full of clothes. “Put these on”. “These” were a collection of girl’s school clothes for one of the local schools. “These were mine” she said, “I think they will fit you”. In fact they were a bit on the small side but I did manage to squeeze myself into her school knickers – a dreadful green colour – and her bra. There was no suspender belt or stockings so I had to pull on some heavy woollen knee socks. Next I put on a white blouse, though as these button up on the different side from boys it was a bit of a struggle, and rather tight too. Finally I squeezed into her dark-green school skirt (which would have fitted better if I hadn’t had a massive hard-on) and some brown school shoes.Ann went out of the room and came back with a long blond wig which she proceeded to fit onto my head. She then ringed my mouth with lipstick, applied mascara to my eyes, and powdered my face.It wasn’t the first time. ”I don’t know why I thought this. I had no suspicion before this moment that Rick might be gay or bi. But something in his manner... Maybe it was the evasive way he answered my question about his porn habits.Or maybe, as they say, the wish is father to the thought. Maybe I wanted him to come on to me.Because there’s something I have omitted to tell you so far; that I am not totally unacquainted with other guy’s bodies.Like many teenage boys, I had done some experimenting, most of it when I was around sixteen, with a guy I’d known since kindergarten. We did some jacking off together, then some jacking off of each other. We were about to move on to blow jobs - which I was keenly interested in trying - when he freaked out and said he didn’t want to do it anymore.His reaction made me feel ashamed of my urges, and in the years since I’d never touched another guy. But those of you who have had such experiences know it’s hard to get that genie back in the bottle, and despite my shame, I had.
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