Pretty Pinky: Life of a Prison Sissy

Two inmates walk from the cellblock to where a correctional officer sits at a desk. The C.O. is a middle aged black guy. One of the inmates is a buff black guy; the other is a small slightly built, very young, Caucasian. The black inmate is dressed in standard prison garb. He has the Caucasian by the upper arm – the way a man walks a woman – and is walking him to where the C.O. sits. The Caucasian has on brown work boots with dark socks rolled just above the tops. He has a towel tied around him, chest high, the way a woman would wear a towel. He has a slave rag tied on his head. Otherwise he is naked. At first glance he looks like a woman. He is what is known as a prison “sissy”. The black inmate is the sissy’s pimp.

The black inmate walks the sissy up to the C.O. The inmate and the C.O. talk and the C.O. gets up and walks over to a cleaning supply closet just around the corner from his desk, and unlocks the door. Then he walks back to his desk & sits down to read a newspaper. The pimp walks his sissy to the cleaning closet and turns on the light. The sissy is carrying a tub of Vaseline. He sets the Vaseline on a shelf and moves a couple of mop buckets toward the rear of the closet. Then he unwraps the towel and folds it in half and lays it on the concrete floor. A closer look reveals that he is wearing red lipstick. The black pimp comes up close to the naked sissy, cupping his small heart shaped chin in his large hand and says a few words before stepping out and closing the door. It is just after 6 p.m. Between now and 10 p.m. the sissy will sexually service a steady stream of men, who will arrange payment with the sissy’s black pimp before going in to the closet. Cigarettes, candy bars, soap, toothpaste – almost any means of payment – will get a man laid, sucked off, his ass eaten out, even a chance to urinate in the sissy’s mouth – depending on how much payment is given. After each customer leaves the closet, the pimp goes in and tells the sissy what the next trick has paid for. And the sissy will comply. 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 homosexual acts, but had been secretly crossdressing since puberty. He was a small, slightly built guy, that no one looked twice at. All that changed the day he got off the bus and went into the tank with the rest of the fish. His freedom was stripped from him – not just by the justice system – but by the man who claimed him as his property, and “he” became a “she!” Keven – Miss Pinky – is as much a slave as any Negro on a plantation ever was, except in this case the slave is white and the master black. “She” was given a new name & forced to assume a female personality, & if all that weren’t enough, “she” was turned out as a prostitute – forced to suck cock and get fucked by countless men, for the benefit of the man who owned “her.”

Now Pinky is standing naked in a broom closet, facing the metal shelving, a powerfully built Mexican man covered in gang tattoos is on “her” back, his muscular arms around “her”, his erect cock buried in the “her” tight anus, & and he’s pounding the hell out of that faggot’s ass. I mean, the whole fucking shelving is bumping up against the cinder block wall, & it’s making one hell of a racket. So much so that the C.O. comes over to investigate. He looks quizzically at the pimp, who allays the guard’s concern by saying, “It’s cool. Officer, that’s just Jorge getting his freak on.”

Then the pounding stops and you can hear the sissy saying, “Did you cum yet, Papi?” A few minutes later the closet door flies open and the shave headed gangsta steps out. He sees the C.O. and puts his head down & walks briskly back to the rec room to shoot some pool.

The guard saunters over to the door, which has been left ajar, & peeks in. The queen is on “her” knees applying fresh lipstick. “She” spots the C.O. and smiles waving “her” fingers at him. The guard shakes his head and laughs. “Pink in the middle & sweet as sugar”, he says, walking back to his desk. It’s hard to tell, but he looks like he might have a bulge in his uniform trousers. Because, let’s face it, that little pink bitch look hella tasty!

Meanwhile, JJ, the pimp is negotiating with a prospective client. No goods will exchange hands here on the floor. JJ has a scrap of paper with the client’s name and what he agreed to pay. In the joint there is nowhere to hide, so if you owe a debt you generally pay it. The brief conversation over, JJ taps on the door and pokes his head in. He gives the queer the heads up on what the next trick has just paid for, then he stands aside as the trick enters the closet for a blow job.

Meanwhile a line is building up outside the closet door. JJ has the names of who is next and what they paid for on the paper. He glances up at the clock; 8:15. Less than 2 hours to go before bed time lock down. The big score will be after lockdown. Pinky has already been sold for the night to 3 El Salvadoran gangbangers. Instead of going to “her” own cell, Pretty Pinky will go to the cell of the 3 bangers who have purchased “her” ass for the night. That means little or no sleep for “her” tonight. Between lights out and lights on – approximately 8 hours – “she” will suck the men’s cock and balls, eat out their anuses, massage their naked muscles, and get fucked in the ass – several times. If “she’s” lucky “she” may get a few hours sleep between breakfast and lunch – before the relentless cycle of whoring for men begins all over again. It is rarely that Pinky spends a night in her own cell; orders for her ass are backed up for weeks in advance. This is the life of a prison sissy. Think about it before you do the crime.

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