Pretty Pinky: Life Of A Sissy In Prison free porn video

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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 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. 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 34, 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.

Which is ironic, because prior to “her’ incarceration “she” had been married for 13 years and was the father of a 12 year old daughter. All that changed the day “she” got off the bus and went into the tank with the rest of the fish. “Her” freedom was stripped from her – not just by the justice system – but by the man who claimed “her” as his property. “She” 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 mexican 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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My Sissy Life Part 3 When I got to my room I saw the Hello Kitty dry erase board on my door. There was a note from my brother that said 'Sissy, I need my jock strap clean by Friday morning.' Oh good, I get to hand wash my brothers jock strap again. Is it Christmas already? Almost every day there is a note on the board from someone telling me that they want me to do something. I walked in my room. I still can't believe how ultra girlie my...

3 years ago
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My Sissy Life Part 15

My Sissy Life Part 15 Author's Note: I started writing this because I was telling a friend about a real life sissy that I knew. He said that I should make a story out of it because people on TG story sites would like to read it. The only thing I knew about TG was that one person that this story was originally about. I never thought I'd write 15 parts. I know I have said many times that this story is not real, and that is true. But just like any other fiction story, it does have...

2 years ago
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My Sissy Life Part 5

My Sissy Life Part 5 I got into my maid's uniform, it was different from my first one. My first one was black with a white apron that tied in back in a big bow. It was off the shoulder style and only came a little higher than mid thigh. There was a little white cap that clipped in my hair also. I had two, but they weren't very well made. They were more like Halloween costumes, they started to fall apart after the first wash. That is when my mother bought me new uniforms. These...

3 years ago
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My Sissy Life Part 8

My Sissy Life Part 8 By Bobbie Doll I went to my room and saw my light pink leotard, white tights and a little light pink dance skirt on my bed. Along with my heels and leg warmers. I was thinking about my life. Most people who knew about me and my life would say ' Your brother treats you terrible.' My father not only made it clear that I am to answer to my brother and sister as I would him and my mother. But...

2 years ago
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A Little About My Sissy Faggot Life

A limp dicked cuckoldMy wife divorced me in the late 90:s. We had been married for seven years, and in this time I had not been able to fuck her properly even once. A couple of times I managed to get my little penis half erect, but I would cum as soon as it even touched my wife's pussy. My failures in bed had nothing to do with her being ugly or so, no she was really beautiful and sexy. Men would always look at her and I knew they all wanted to fuck her.After our first year my wife took a...

4 years ago
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Teaching The Sissy Maid Workshop At The MVG Chapter Two Jaime Learns About Life As A Sissy Maid

I led Jaime from the garage to my master bedroom in the back of the house and told him to get in the Waiting Position as he had done before and to remain silent until he was told he could talk.  I smiled when he nodded his head up and down for yes since he had just been denied the right of speech.  Perhaps he may just become as valuable as he appears on first glance, but that was rarely the case and each sissy was a reflection of the woman who transitioned him from his maleness.  He was merely...

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2 years ago
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Me And Pinky At The Movies

This one involves a new partner I met through Indian sex stories …Pinky with the pink pussy! I was pleasantly surprised to get a mail from her one day complimenting me on one of my stories, and before long we ended up meeting! Let me tell you about Pinky…a gorgeous fit woman with stats to feel more than measure! And I was lucky to do just that!! She has these superb tits that are firm with aerolas the size of a 2 rupee coin and dark red nipples that come out from their center just begging to...

3 years ago
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Horny Sex With Sexy Pinky

Hi guys this is Amar and this is my first post on HD. I am a very regular reader of this site and I am going to narrate my first experience with Pinky who was my classmate in Engineering. Let me first describe u Pinky she is a peculiar south Indian village girl with stats 34 28 36 and the best part in her is her Boobs. In college she had a boy friend and and they were in a relationship for more than 3 years. Recently they broke up and she is alone for some time. I never spoke to her when i was...

3 years ago
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Pinky ko pink kiya

Hi dosto ye meri 1st kahani hai isliye agar galti ho to maf kar dena, mera pahla sex anubhav mai yahan pe aap logo ke sath bant raha hun, i hope aap log pasand karenge. Baat un dino ki hai jab mai 11th class me tha, class me sabse sidha bachha jise sex ki abc nahi aati thi, Mere ghar me do kiraye dar aaye ek ka naam pinky aur dusri ka naam sweety pinky bahoot gori aur sweety sawali thi, dono hi kafi jaldi mujhse bahoot ghul mil gayin, vo log mujhse 2-3 sal hi bade the, isliye koi bhi baat...

1 year ago
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My Sissy Life Part 13

My Sissy Life Part 13 Everyone was looking at me, I hoped I could get into school without any problems. I hoped that they would think I was just another girl going to school. I hoped they didn't hear my mother say sissy. I hoped that they would just go back to talking to each other. My hopes didn't come true. A group of kids started walking toward me, there were two boys and four girls. The boy that was leading the group was named Terry Renex, everyone called him T-Rex. He was...

2 years ago
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My Sissy Life Part 12

My Sissy Life Part 12 ---Because the person that this story is loosely on has passed away from cancer, I had stopped writing. Before her death she asked me to continue the story. As for those of you who are going to get all upset that I'm keeping the story going or that this story is wrong. I say, don't read it. I don't care if you don't like it. I mean, I really don't care if you don't like it. However, I really do care if you do like it.--- With that said...here we...

1 year ago
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True Life Sissy Daddys Mad and Im in troub

Hello. I'm Tiffany. That's me in the picture, hiding in a bathroom stall, heart pounding, after being abandoned in a porn theater parking lot in just those crotchless panties. I an evolved Sissy. It was younger days I had forced feminization fantasies or got arousal telling others to call me a sissy. Now there is no forcing and I proudly call myself a a pink panty wearing sissy, because it is exactly who I am. My entire life had always been devoted to femininity to the excess. I have learned to...

2 years ago
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My Sissy Life Part 4

My Sissy Life Part 4 I started putting my clothes away. I picked up my bra and panty sets and thought to myself. Wow, I've come a long way from that first day dressing as a sissy. From being terrified about going outside in a skirt to it becoming almost normal. Who am I kidding, it is normal now. I'm a sissy, I know it, my family knows it, heck, the whole town knows it. I do what I'm told and I do it while looking as pretty as possible. The first year was the hardest....

2 years ago
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My Sissy Life Part 18

My Sissy Life Part 18 The next morning I woke up and my mother helped me out of my girlie gear. After my shower I went back to my room and found that my mother had already picked out my clothes for the day. On my bed there was a light pink t-shirt with a cartoon fairy on the front and a faded blue denim mini skirt with about 2-3 inches of pink and blue fabric and lace at the bottom. The skirt had a pink and white glitter belt with it. Along with my white ruffle top ankle socks a...

1 year ago
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My Life As A Sissy Baby

My Life As A Sissy Baby By Sissy Baby Tammy Hi there my name is Bob Young or at least it use to be. It is now sissy baby tammy. How did I come upon that name? I will tell you about that and the wonderful lady I have met Goddess Andrea. But first let me tell you a little about me. I have always been a sissy, I was small for my age, and I was always picked on by both the boys and the girls. I would cry a lot when this happened and I was always told to stop acting like a baby....

3 years ago
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My Sissy Life Part 6

My Sissy Life Part 6 As I went to my room to change into my serving uniform I realized that I was home alone. I guess I was really into my cleaning. A few years ago, if I was left home alone I would have tried to run away, but now I just keep up with my chores. It is strange how things change sometimes, besides where would I go if I did run away. I quickly got out of my cleaning uniform and went to take a shower. I knew I better hurry, I only had an hour and a half to get ready....

3 years ago
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My Sissy Life Part 11

My Sissy Life Part 11 I stood there with my nipples hooked to the wall for about five minutes, not knowing when my brother was going to come back to let me down. I heard my sister say "Oh...my... god." I could see her out of the corner of my eye. "Whatcha doin' Bobbie, hangin' around?" she laughed "Sorry, I couldn't resist. That was a dumb joke, I know." She walked over to my side, looked at my situation and said "Well, Jim is creative, that's for sure." "I love the belly...

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