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Crossdressed Prison Gangbang

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2003-10-07

The usual, predictable acts performed for them, but no-one minded. There was a Johnny Cash, a terrible stand up comedian etc. . No real notice was taken until a young inmate entered the stage to do his Britney Spears rendition, dressed in a schoolgirl uniform. Wolf whistles almost drowned out his ' hit me baby. . ' . Well, he looked very convincing in his pigtailed wig, make-up, miniskirt and white knee length socks. More than a few men in the audience drooled at the sight before them as he camped it up, lifting his skirt and flashing his panties at them. The atmosphere started to get a little charged. The performance ended to loud cheers and ' Britney ' left the stage and headed back to the guards locker room where he would get changed. He shut the door behind him and let out a sigh of relief, smiling to himself at how well it had gone. He'd been very nervous about doing the act in drag as he knew there were more than a few men who wanted to fuck him anyway, let alone when he was dressed like this. Still, he wanted to do something different and it had gone down well. " That was real nice. "He span round to see two guys standing in the doorway.

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   " Err. . thanks. " he replied, nervously. " You look real pretty. " The other one said as they both slowly advanced toward him. " Now fellas, don't get any ideas. . . " he stammered. But it was in vain. The two inmates grabbed his arms and dragged him, kicking, to the shower cubicle. He screamed out for help but was pushed to the floor. The men started to undo their overalls as they stared hungrily at him, sitting on the cold concrete. All they could see in front of them was a sexy schoolgirl who needed a good fucking.

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  " Don't do this. " he pleaded. " If you struggle, we'll fucking kill you. "He knew he had to go along with it, they were serious. They would cause him serious pain if he tried to fight them off. One of the men started to wank himself as the other grabbed the collar of his school shirt and pulled him to his knees. " Suck it you little bitch. C'mon suck my dick. " The hard cock was pressed against his closed mouth, forcing it open and sliding in forcefully, inch by inch until it almost choked him. The prisoner rocked his hips slowly, fucking 'Britney's' mouth in a steady rhythm. The other man, now naked, walked round behind and pulled up the pleated miniskirt. He squatted down and grabbed the hem of the white panties and tugged them to one side revealing ' Britneys' bare ass. He was now sucking on the big guy's cock for all he was worth, wanting to get it over with, when he felt a finger slide into his asshole. He let out an involuntary whimper and felt almost turned on as the finger worked it's way in and out of him. " The liitle bitch is enjoying it.

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  " said the man behind. " Look, she's getting hard. "And to his own disgust, his cock was getting hard. He couldn't help himself and he felt ashamed. Just then he heard another voice and looked up to see three other men enter the cubicle. " Well, well, looks like we got a party going on here. " One of them said. The men started to strip, grinning at their luck. Now he was scared again. The finger slid out of him and he felt the fat tip of the prisoner's cock press against his hole. He braced himself as the head squeezed into his tightness. He tried to let out a scream but was silenced by a second erection stuck into his mouth. He was now in the middle of a circle of men wanking themselves off over him as he was being fucked in the ass. The first man let out a sigh and with a quiver of his hips, fired a jet of cum down his throat, spilling down his neck and shirt. Straight away, another cock pushed it's way into his mouth, barely giving him time to breathe.

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   He felt warm cum shoot up his ass and the man slid out, replaced by an even bigger one who was rougher and more hurried. He didn't know how much more of this he could take. Another inmate came over his face, now all smeared lipstick and sticky spunk. Maybe another twenty minutes passed as he was repeatedly screwed by the men. When they were finished with him, he lay limp on the shower room floor, too tired to even cry. He tried to get up and felt wet cum dribble from his asshole down the inside of his bare thighs. The pain was unbearable. It was a tough lesson and as he staggered to his feet and flicked the shower on he knew next year he had better learn some Johnny Cash songs. .
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