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She was shaking now and nearly panting with a mixture of nervousness and extreme arousal as she felt something pressing against her swollen anus. It was not his finger this time. He pushed his cockhead into her butthole now and quick probing movements. Each time he forced more of it in to her. She closed her eyes and took a deep breath trying to take it. He was forceful and pushed some of his cock into her ass. She could tell that this was a thick cock and it was not going to be easy to take it. It was increasingly uncomfortable as the stranger’s thick tool stretched her tight ass and she groaned out load but at this point she was totally powerless to stop his relentless penetration or her beleaguered asshole.He now grabbed her hips firmly and pushed his swollen cock deeply into her."OWWW!" she yelled. It hurt now as his pushed in and out entering her ass deeper with each thrust. She had experienced anal intercourse before but never with a cock as obviously thick as this one. He was. One of the girls, Nancy said, "youwould be a pretty girl, because you are a cute boy." What they saidstayed with me in my mind, I could not stop thinking about it, thethought had made me question myself, was I really more like a girl, wouldI look pretty if I dressed as a girl, I had to find out.I was going to babysit my younger step-brother and half-sister onSaturday night when my Dad and Step-mother were going out, my Step-aunthad to work, and my big brother would be hanging out with his friends.My Step-aunt was the same size as me, I put the kids to bed early and Igot dressed up in her clothes: panties, a bra which I stuffed withsocks, a dress, pantyhose and a pair of 3 inch high-heels, next came anattempt to apply make-up. I did not know what I was doing and wasguessing at what went where and how to put it on, a minimal start eyeshadow, mascara, blush and lip stick, then I saw what I needed, a fallwig and it was the same color as my hair, I took this as a sign andplaced it on.
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