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As he pushed in I yelped out in pain, and as I did other cons started cheering him on, this seemed to fire him up more and he told me to shut the fuck up or else, I had to bite my lip as it felt like he was ripping me open. I can’t really explain what was going through my mind or what I felt as I was in to much pain, his onslaught was relentless, he was going to fuck me no matter what anyway. He had a firm grip on my hips and was now building a rhythm, I thought I was going to faint, I don’t think that would have stopped him either, if nothing else this was going to make me more considerate to women when we have sex. The chants from other cells was still going on, I blanked my mind completely as he used me but I could not shut out the pain and discomfort I just wanted it over with. A few more thrust’s and he grunted, I felt him stiffen and knew he was cumin in my ass, this at least. "Okay Sissy, have you been fucked in the pussy yet?" I explained to mistress the extent of my experimenting with my anus, reminding her that I had taken big boy, only that morning. She nodded approvingly saying "well that's a start, but I think I may have to take it easy on you. Take off your dress" with that I slipped the dress over my head and hung it up. I took the opportunity to examine myself in the full-length mirror, I thought I looked beautiful, the corset with the fake breasts, the stockings and suspenders and those killer shoes. I gave myself an erection.Mistress became much more stern. "Okay choose the strap on that you want in your arse" mistress was very clever she knew that I wanted to prove what a good sissy I was, so I would choose the biggest one possible. Which is what I did. Mistress raised her eyebrows and nodded in appreciation. "Head back, and give this b**st a blowjob"I immediately tilted my head backwards and taking the strap on from her attempted to get as.
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