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She was spread far beyond what she had ever expected. It was not painful, but it was mind-blowing. She quickly came to the barrier of her hymen and stopped.Doug said, "Give yourself time to adapt to being filled and then push steadily against the barrier. It will break as it tries to stretch out of the way. It will hurt some when it breaks, but the pain will go away, quickly. When it does, just continue to ease down on my cock. Anytime if feels like you are getting dry, just pull up a little and ease back down. Before long, you will have taken me as far as you can. Don't rush, just work your way through the experience. Once I'm in all the way, the fun will begin!"Evening Star followed directions and felt the pressure against her cherry. She eased down slowly and felt it stretch. It was uncomfortable, but not painful. Suddenly, there was a sharp, tearing sensation and a jolt of pain. She grunted, but relaxed when that was the end of the pain. She paused for a few moments to regain her. Just like any whore out on the streets, a prison sissy is a slave and must obey his pimp completely.This particular sissy is named “Pretty Pinky”. That’s not his real name. His real name is Keven. But once a punk has been turned out as a sissy, his owner will give him a "street" name – a female name. And from that point on that sissy will, for all intents and purposes, be a woman. Pinky is 19, but appears to be much younger. “She” has been in prison for almost a year now. “She” has belonged to JJ for most of that time. Pinky’s smooth white skin is covered in prison tats – crude, homemade tattoos. Pinky is what is known in the joint as a “Patch Carrier”, meaning “she” sports “her” man’s name & affiliation prominently emblazoned across “her” buttocks so that there is no doubt as to whom “she” belongs to. Pinky is a particular prize in the prison subculture because “she” can literally pass as a woman – “she” looks that feminine. Until his incarceration, Keven had never engaged in.
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