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My sister is away in college and the neighbor, a junior college boy Jeff, takes care of the cat and plants.I went to pay bills and caught him in my sister's room wearing her clothes, make up and wig jerking off to bikini pictures of her and her girlfriends. He was so embarrassed and afraid of being outed he offered me whatever I wanted not to tell. I told him I would not if he would do as I wished. I asked him if he thought girls and guys were attractive and he said yes. I had him lie back down on the bed, look at the pictures and start jerking off again. He was embarrassed but I told him I liked what he was doing, enjoyed his being dressed as a woman and that he was passable. I told him he really should be a she and that everyone would get excited seeing her outside and not know she was a he. He said he shaves everything and wanted to go out dressed and I said we would go out together. I told him I had fantasies about what he was doing and had worn some women’s clothes before and. More than one pair of bare feet and quiet talking. I swam madly for the side of the pool, no thought in my head but to run away. I had climbed out and was grabbing my stuff when two arms grabbed me around my chest and I froze. Those arms held me, pressing my back into a firm pair of boobs. The arms turned me around and I was looking into the face of Crystal, the head lifeguard. Crystal was only about five foot five, but had a 34c rack and always wore a too small blue Arena swimsuit with a small opening above her sternum. The tight suit always gave her an impressive camel toe. She was in her mid 20s, had shoulder length dirty blonde hair and had the natural curves of an athletic woman who is not a diet nut. Behind her was one of the junior lifeguards, Joey.The same height as Crystal, Joey was thin and lithe, but clearly not the natural athlete Crystal was. Joey was trying to hide a serious boner and seemed scared."Why did you stop him? If we just let him leave he wouldn't.
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