1. Prison Bitch (for all my little sissy fag boys)


    Date: 11/25/2014, Categories: Anal, First Time, Gay Male, Author: plumprumpbrat, Rating: 94, Source: xHamster

    high nylon stockings that must have had at least a dozen long runs in them. So as we reached the step 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 lewdly 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 were 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 an exaggerated feminine manner over to his far corner shower. I was quickly and closely followed by a good 1/2 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 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 pick it up. He also added that I should take my sweet ass time! Tightly closing the gap between us, I deliberately turned my back to him before slowly bending over. Before we had left our cell, Pauline had carefully lubed my anus with some of 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 careful 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 managing to escape Smiddy's punishing cock. It was then that 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 securely held in place! Smiddy seemed ripshit and wasted little time lining my anus up for a second attempt. Again he greedily shoved it deep into me with the very same painful results. This time I was completely helpless to break free and escape. I began to openly weep then, while he ...
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