1. MY GAY PRISON SISSY ****


    Date: 7/18/2016, Categories: First Time, Gay Male, Shemales, Author: cddixie, Rating: , Source: xHamster

    decided the time was ripe for me to come out of the closet and to act on my urges toward cock and not surpress them any longer. Paul helped me in part that night by giving me a pair of black fisnet thigh high nylon stockings that must have had at least a dozen long runs in them. So as we reached the strip area in front of the laundry bins, I shed my prison regulars but remained in both of those sexy black flower top fem stockings. Instantly I was the topic of interest for the other 30 plus inmates around me. Officer Goodman informed us all that it was the full time duty captains night off and instead of the usual 20 minutes of shower time, we were getting an extra 15 minutes. He also added while lewedly smiling, that he didn't want to see a single drop of cum hitting the shower room floor! Looking around, I saw that many cocks were already in full erection as Pauline and I where the last inmates to enter the steamy room! Having chosen Smiddy a well built Irishman that had been nicely buggering Pauline for months now, I sort of pranced in a exagerated feminine manner over to his far corner shower. I was quickly and closely followed by a good half dozen erect inmates as I arrived there. Smiddy was facing me now holding his long thin already erect cock in his hand wearing a big cheshire cat type smile. Looking him straight in the the eye, I asked him if he would like to be the first inmate to throw a wild fuck into my virgin ass? My mind was racing then a million miles an ...
    hour in a state of very turned on lust I had never know before. Smiddy's answer was to grab a bar of soap from his nearby wall holder and carefully drop it on the wet floor just in front of him. Never breaking eye contact, he ordered me to bend down and very very slowlypick it up. He also added that I should keep my feet well spread apart! Tightly closing the gap between us, I delibertly turned my back to him before slowly bending over. Before we had left our cell, Pauline had carefully lubed my anus with some of the her new cooking lard she stole during our supper duties. For foreplay, she had also given me a very erotic two finger assfucking so I was as slippery as a greased pig back there. I guess the sight of my exposed lubed shiny new fuck hole was too much for Smiddy to stand! Almost instantly he moved forward placing his hard cockhead against my tight anus. True to his dominant male nature, Smiddy took me fast and hard. Pauline had always been so gentle and carefull in her anal play with me, that I never dreamed that a stiff cock could or would hurt so much! I was totally unprepared for the horrible pain that felt like a red hot branding iron going deep inside of me. My instant reaction was to scream and instantly move myself away successfully manageing to escape Smiddy's punishing cock. It was then, several inmates moved in on me and I was grabbed by many sets of strong hands and f***ed to bend over again while now being securly held in place! Smiddy seemed ripshit and ...
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