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Prison

Maximum Security Prison  Sissy Sessions - Plus

Monday evening at dinner The Deacon announced to his table that the following Saturday night he would be taking Jesimae as his own prison bitch wife.  He expected her to scream and moan so loud that the entire prison would know when shed given up her anal cherry to him.  Jerrod, aka Jesimae, sat next to his cell mate looking down at the plate of cum that was his/her dinner.  She was forced to give her cell mate and future prison husband a clandestine hand job under the table so she would be able to scoop up his offering in front of his underlings proving to them that she was committed to being his bitch.  Jerrod sat in his female denim shirt, pants, white ankle socks with little yellow bows, and black Mary Jane shoes trying with all his internal might to keep from crying.  If Diego hadnt given him something to eat before he returned to his cell in preparation for the evening count and meal, hed have only The Deacons cum to fill his stomach.  All of The Deacons sycophants sat smiling and quietly congratulating him in getting Jerrod/Jesimae to actually jerk him off under the table without getting caught.

Monday night was a typical evening for the two incongruous cell mates.  The Deacon made of point of taking a healthy shit in front of Jerrod/Jesimae and instead of sitting to piss as one would when taking a shit he stood up and made Jerrod/Jesimae hold his cock as he emptied his bladder.  Then he made Jerrod/Jesimae do something short of the ultimate humiliation.  He forced Jerrod/Jesimae to clean his dirty asshole with single sheets of toilet paper.  Short of having to suffer the unimaginable consequences of not doing what his future prison husband asked, Jerrod/Jesimae knelt down behind his towering cell mate cleaned his asshole.  When he was done and The Deacon felt he had done a good enough job, he bent over and commanded Jesimae to kiss and lick his asshole.  Jerrod/Jesimae again knowing what the consequences would be if he didnt comply, leaned in and placed a gentle kiss on his cellmates anus.

Dats it swee pea!!!  Youz a learnin how to makes your man happy.  Now let me feel that swee tongue of yours lap at my man hole, moaned The Deacon as he leaned over the steel commode presenting his asshole to be licked.

Jerrod/Jesimae continued to lick on, around, and in the asshole he just cleaned, but couldnt get past the fact there was a small amount of fecal matter still remaining in the center of his asshole.  He continued to get past the taste and smell and after a good fifteen minutes of sucking The Deacons asshole, he was surprised to feel it pulse.  When he pulled back to see what had happened, The Deacon stood up and showed him the white sperm that was all over the stainless steel toilet seat.  Jerrod/Jesimae couldnt believe that The Deacon had an orgasm from him licking his asshole.  He looked up at his cell mate only to see him pointing to the white liquid that covered the seat.  Jerrod/Jesimae didnt need to be told what to do.  He/she crawled over to the commode and began licking his cellmates cooling ejaculate off the toilet seat.

The Deacon smiled to himself and praised Jesimae for her awesome display of servitude.  The rest of the night nothing special happened.  The Deacon rested on his lower bunk while Jerrod/Jesimae read about being a girl on the top bunk.  At 11:00PM when the lights went out, Jerrod/Jesimae climbed down from his/her bunk and joined The Deacon in his.  Jerrod/Jesimae was not forced to suck his future husbands cock before they fell asleep, but he knew that the coming Saturday night hed be on his stomach, ass high, and cheeks spread for the taking of his anal cherry.  As he fell into a deep sleep, the last thing he remembered was his obligation to take The Deacons morning wood into his mouth so he could either suck him off or be forced to drink his morning piss.

Much to his chagrin, Jerrod/Jesimae did not wake up before The Deacon.  He was awoken by The Deacon when he pushed him out of the lower bunk and onto the cold cement floor of their cell.  Jerrod/Jesimae scrambled to his knees facing the lower bunk and waited.  He had his fingers crossed that the only thing hed have to do this morning was swallow a large load of The Deacons ejaculate and not have to suffer the humiliation of drinking his piss.  The Deacon surprised him when he made him hold his cock as he pissed into the commode.  Jerrod/Jesimae made sure that none of the urine got on the seat as he knew The Deacon would make him clean it off with his tongue.  His second surprise was when his cellmate told him/her that he/she should just get ready to go see Mistress Dee-Dee after they return from their morning meal.  Jerrod/Jesimae got to start his day without having to suck off his cellmate.

Tuesday morning Jerrod/Jesimae learned that she would begin to take four pills every day for a month.  Then she would continue on with two a day for another sixty days and if everything was to Mistress Dee-Dees liking, Jerrod/Jesimae would have to just take one pill a day like any good female on birth control pills would.

Jerrod incredulously asked, Pills?  What kind of pills?

Oh, sweet pea, theyre birth control pills.  Theyll give you enough estrogen to soften and feminize your thin little body.  Grow you some nice little titties and shrink your all ready small penis and balls.  If everything works out, no one will know you have little boy parts between your scrawny legs.  You will look just darling in your female attire.  Even when youre wearing your denims youll look feminine.

Jerrod/Jesimae didnt have to hide his/her emotions in front of Diego and began to cry like a little girl.  Im not a fag or a guy that wants to live the rest of his life as a sissy.  Please, Diego, dont make me take those pills.  Tell The Deacon that I am and theyre not working.  Please!!!

Sorry, Jesimae  There is nothing on the face of this earth that would make me lie to The Deacon and that includes as many toothless blow jobs as you want to give me for the rest of your time here.  Best thing to do sweetie is accept your fate and be the best she-male sissy you can be.  And if we need to, Flavio or Calixto can force you to take your pills

Jerrod/Jesimae was at his/her wits end.  He took two tissues from the tissue box on Diegos counter to wipe his face and blow his nose.  I think Id rather have had the death penalty given to me.  At least, Id be on death row in a cell by myself.  I cant fuckin think about living the rest of my life as some prisoners bitch.  Im only eighteen and have, what, some sixty to seventy years in this fuck hole.  And, that is if I live that long.

Diego stood looking at his protge not being feminine at all when the idea bulb ignited in his brain.  He broke out in laughter and when he calmed down he said, Jesimae, what did you notice about all the cells on this tier?  Have you taken into that addled brain of yours the difference with this tier and the one youre on?

Jerrod/Jesimae looked at Diego with a quizzical look on his face.  Since hed only been in this one cell he really couldnt respond with a truthful answer.  Diego, excuse me, Mistress Dee-Dee since Ive only been in this cell, which I believe is yours, I cant really answer your questions.

Yes, I forgot that youve only been in this cell which is mine, but as you get more comfortable with your training over the next week youll be walking around this tier.  What you will see is something that will make you beg to be transferred here.  On this tier Miss Jesimae, there is only one prisoner to a cell and if you take the time to look around youll see that we have the ability to decorate our cells.  Look at my bunk.  What do you see?  Look, you see dust ruffles, colored sheets, blankets, and not one but three pillows.  No macho bullshit.  No suckin your cellmates cock morning, noon, and night.  No having to moan when hes fucking you so the tier will know youre his bitch.  You live here as a she-male and all you have to do is perform your womanly duties during the day and at night youre left alone to take care of yourself.  And, you can set your cell up anyway you want.  The screws will leave you alone, but of course, youll be suckin and fuckin some of their cocks as well.

But, you know that is not going to happen.  You know that cock sucking warden put me into that cell with The Deacon to see if Ill survive in this place.  And all he wants is for me to do something wrong so The Deacon will do to me what he did to the guy that bit his friends cock off, said Jerrod/Jesimae his body beginning to shake from the stress of having to become a she-male.  All he wanted was to be left alone and that is not where his life in this hell hole was headed.

Diego could see Jerrod was in a lot of turmoil over his feminization and forthcoming marriage to The Deacon.  Hed witnessed guys committing suicide just to cease their self loathing decline into their perceived depravity of feminization and homosexuality.  Diego felt a tremor of fear course up his spine as he stood in front of Jerrod/Jesimae as she tried with all her fortitude to stop what was happening to her.  Listen to me Jesimae; Ive seen guys do some stupid things because they couldnt cope with their imagined loss of virility.  You need to listen to me and if you do, in about four to six weeks youll be transferred up here with us girly bois.  See, Jesimae, the prison system frowns upon keeping girls like us with the macho hardened criminal types.  It is bad enough we have to service them and are the prostitutes of the prison, but if you play your cards right, youll live on this tier in the prisons lap of luxury.

Jerrod/Jesimae calmed down and asked, And, how do I play my cards right to end up living here instead of with The Deacon as his bitch?

First you accept your feminization.  Second, you give to The Deacon your anal cherry; I mean it is still cherry?

Yes, it is, croaked Jerrod/Jesimae.

Good, because hes going to fuck you Saturday night and then, hes going to fuck you morning and night for the week following.  Youre going to be so sore it will be hard for you to sit down.  This will be the clue to the screws to go to the warden and get you removed from his cell.  Of course, youre going to have to give yourself to the warden, but that will only be a blow job.  Then, voila, youre living here and Ill promise you that you will be in the cell right next to me.  Well have so much fun decorating your new sissy home.

What about The Deacon? asked Jerrod/Jesimae with his voice echoing his total disbelief.
Diego smiled, stepped close to Jerrod/Jesimae, took her in his arms, and whispered, Hell come here for his pound of flesh and of course hes going to whore you out to his friends, but that will only be during the day and never at night.  Then after the evening meal youll be here with us girls and we can relax and have our own fun.  Wouldnt that be nice?

Jerrod/Jesimae pushed Mistress Dee-Dees arms from his/her body and stepped away.  He looked up at the ceiling of the cell and then down to the floor.  He/she was so tense that the blood vessels on his/her neck were popping out.  He looked up and saw one of the two Mexican convict guards standing at the entrance to the cell.  He looked like he needed something from Diego.  Jerrod/Jesimae could get any words out of his/her mouth so he/she just pointed and Mistress Dee-Dee turned to see Calixto standing there.

Que pasa, dude?  What brings both of you here?  Cant you see Im busy helping Jesimae?  She has a lot to learn, although shes not being very helpful.  Diego stood waiting for the Mexican to answer.  There was the sound of someone screaming, but that wasnt an unusual occurrence for a place that held some of the states worst offenders.

Calixto related the problem, Diego, in Leticias place there is one fuckin crazy Nazi bastard.  He is threatening to beat the shit out of Leticia because shes black and hes drunk out of his skull on prison moonshine.  Listen, you can hear her screaming at him.  Flavio is all ready on his way to her cell.

Diego screamed, You fuckin idiot!!!  Go and take that white supremacist asshole by his fuckin balls and get him the fuck out of her cell.  Ill be there in just a few shakes of a lambs tail.  Calixto made a bee line to Leticias cell about halfway down the tier.  Jesimae, there is no need for you witness what is going to happen.  Just stay here and practice walking and being sexy.  Ill be back in a few.

Diego ran down to Leticias cell and arrived just as Calixto had John Walton by the throat and was pressing him up against the small column of cement that separated each of the cells.  His white face was red.  His eyes bulged out of their sockets.  Although Calixto was four inches shorter than the Nazi sympathizer, he was ten times stronger and more adept at taking idiots down to their size.  Flavio was inside the cell doing everything he could to calm Leticia down.  Leticia was not a small girl in both height and weight.  She knew when she was imprisoned that the only way she was going to survive was to prove to anyone that mattered she was one of the best cocksuckers to ever pass through the gate of this prison hell.  Her only condition for performing sexual favors was that only larger than normal black cocks would have her permission to enter her male pussy.  Leticias male pussy was bound by one of the biggest pair male pussy lips in the entire world.  She had a tremendous booty and she only gave it to black men with cocks that could penetrate her as deeply as possible.

Diego stood as Calixto continued to choke the life out of John and just when she thought the white asshole had enough she stepped up to Calixto and tapped him on his shoulder to tell him to let go of Waltons neck.  Calixto did just that but did not take a step back to let Walton know that if he made one stupid move hed be sailing over the railing and bouncing on the floor below.  John Walton was too worked up and too fuckin stupid to realize that if he made the wrong move, his life would be over.

What is wrong with you Walton?  You know that Leticia does not let white supremacist assholes fuck her.  So, get your white ass out of here and dont think Im not going to tell your goose stepping commander that youre banned from coming here, said Diego.

Walton was just a dumb mother-fucker.  He didnt reply.  He didnt calm himself down.  He made a move on Diego.  It was the wrong thing for him to do, because Calixto was ready for his stupidity.  He caught Waltons right arm just below his wrist.  He used the force of Waltons punch to sail him against the railing causing him to end up half hanging over it.  Calixto pressed Waltons neck and took him by his belt, lifted him up, and tossed him over the railing.  Walton screamed and tried to get a hold of anything, but he didnt have anything to grab onto.  His body made a thumping sound as it hit the floor thirty-six feet below.  He hit head first.  When the rest of his body hit his head was all ready split open and his brains were splattered on the floor.  Blood began to pool around his head.  Diego didnt flinch when he saw what happened.  Diego, Calixto, and Flavio made a quick exit in different directions because they knew the prison was going to be put into lock down.  They were facing murder charges because by the look of Waltons head he was dead.  Each of them had so much time to do another life sentence was not a terrible thing to face.

Diego saw Jerrod/Jesimae standing on the tier and ran up to her.  Jerrod/Jesimae had a look of total disbelief on her face.  Did he just toss that guy over the railing? asked Jerrod/Jesimae.

Listen asshole, before you say another word, you didnt see a fuckin thing.  You were in my cell putting make up on.  You even hint that you saw what happened and I promise the person who shoves a shiv in your back will be me.

Jerrod/Jesimae had to let Diego know that he was not going to say anything.  He had to prove to him that he could be trusted.  You dont have to worry about me, man.  I could care less about him or any other fuckin white supremacist asshole.  I just couldnt believe how fuckin strong those two Mexicans are.  Should I stay or go?

The klaxon began to sound notifying the screws and the warden that something terrible had happened.  Guards were mobilizing for shutting down the prison.  Before Diego could respond to Jerrod/Jesimae, three guards arrived on the third tier and pushed everyone against the wall away from the railing.  Diego stood next to Jerrod/Jesimae and just eyeballed him to be cool.  They stood as the guards began to round up the rest of the players in the murder of John Walton.  Diego, Flavio, Calixto, and Leticia were taken down to holding cells near the administration building to be interrogated.  Luckily for Jerrod he was taken back to his cell and was told that if they needed him, theyd come and get him.

When The Deacon arrived he noticed that Jesimae was still dressed in her sissy finery.  The Deacon figured correctly that his sissy bitch didnt have time to change before the screws arrived considering someone had tossed John Walton over the railings to his untimely demise.  He didnt give two shits that the white mother-fucker was tossed off the third tier to become floor pizza.  All he could see was his Jesimae dressed all pretty and lookin like she wanted some lovin.  Jerrod was actually hoping that The Deacon would let him change before anything else could happen.  The loudspeaker system though out the prison announced a forty-eight hour lockdown.  Jerrod/Jesimae looked at The Deacon questioningly.

Jesimae, guess wez stuck here for four days sweet pea.  The boyz will be bringin usn three meals a day here in our little hole in this here prison.  You aint gettin' no more sissy trainin.  And, Iz sad that Iz aint gonna see youz in youz pretty white weddin gownz.  But youz know what?  Since wez a stuck here and no screws is a gonna bother us.  Im just in the mood to take youz now.

As Jerrod/Jesimae stood in the middle of their cell, a wave of fear passed though out his body which resulted in him pissing where he stood.  He was so afraid of what The Deacon just told him that his fear just made him empty his bladder.  He did not want to feel the mans humongous cock being forced up his ass.  The Deacon broke out laughing when he saw the pool of piss forming between Jerrods legs.  He laughed so hard he had to sit down on his bunk until he could stop.  When he did he spoke, Well girl, guess youz is a gonna have to clean up youz piss.  Youz a fuckin murderer of five peoples, three of dem chiln, and youz afraid of havin my big black cock shoved up youz cherry pussy-ass!!!  Herez the deal asshole.  Get fuckin undressed.  Totally fuckin neked.  Clean up your sissy piss mess and prepare yourzself to get bitch fucked.  No matter howz you try to stop the inevitable, itz a goin to happen.  Consent or be raped.  Your choice, bitch.

Jerrod stood shaking and not listening to The Deacon.  He didnt want to get undressed or clean up the pool of piss that was between his legs.  All he wanted to do was go home.  He looked at The Deacon and said, Please, just let me suck your cock.  Cum down my throat or all over my face, but please, dont fuck me.  Youll rip me into two pieces.  I cant take your cock up my ass.  Im not big enough. Im no fag!!!  Please!!!  Jerrod realized he spoke the wrong words to his cell mate and started to move away from where The Deacon was sitting.  He also saw that his cellmate was not boiling over in a rage, but continued to sit contentedly on his bunk.  Jerrod knew something was brewing in The Deacons addled brain.

Thaddeus Washington got his nickname when he was just thirteen years old.  He was bigger than any of his friends and most of the older guys in the neighborhood.  He beat the shit out of the leader of the local street gang and dragged him go to the local Baptist church to kneel, pray aloud, and confess his sins to God and Thaddeus.  When the guy did as he was told, everyone who knew Thaddeus nicknamed him The Deacon for getting the baddest mother-fucker to kneel in church and pray.  Remembering how he got his nickname gave Thaddeus Washington enough time to plan his rape of the eighteen year old white piece-of-sissy-shit that had pissed on his cell floor.  Maybe hed just do to Jesimae what Jerrod did to the young Bonds boy.  He sat staring at the cowering teen wondering if he felt like a tough guy now.  The Deacon stood up, walked the few steps he needed to where Jesimae stood, and bitch slapped her.

Jerrod really didnt see the slap coming and the force tossed him back and into the small opening that existed between the end of the bunk beds and the back wall of the cell.  It was in that corner The Deacon beat Jerrods face against the metal bar of the bunk bed the first night they were together in the cell breaking his eye socket, nose, and crushing all but three of his teeth.  Jerrod landed against the wall and slipped down into the corner.  He was stunned and woozy from the slap.  Before he could react, The Deacon was on him.

Thaddeus Washington was one pissed off nigger.  He picked up Jesimae by placing his left hand under her chin and his fingers around her neck and lifting.  He spun her around like a rag doll.  He used his left forearm to pin her against the wall.  Jesimae was wearing a short denim miniskirt, stockings, small black leather heels, and a white cotton blouse.  The Deacon didnt care if she was wearing panties because hed just rip them off to get to her virgin pussy-ass.  Jerrod/Jesimae tried to wiggle out from behind the bunks, but didnt have the strength to overcome the powerful hold The Deacon had on him.  Jerrod heard and felt The Deacon open his belt, unbutton and unzip his pants, and drop them on the floor.  He knew that The Deacon never wore underwear.  Jerrod/Jesimae began to cry.  He pissed himself a second time.  There was nothing he could do to stop what was going to happen to him.

The act of slapping and manhandling the teenage boy was enough to get The Deacon sufficiently erect to be able to penetrate the terrified boy.  Jerrod could feel The Deacon stroking his cock and cried, Please, please Dont do it this way.  Please, Ill give it to you, but dont, please dont rape me!!!

Laughing The Deacon responded by placing the head of his uncircumcised fourteen inch cock between Jerrods tightly squeezed together ass cheeks and pushing.  No lube.  No spit.  Just the small amount of pre-cum that leaked from the tip of his broad cock head was all the lubrication Jerrod was going to get.  The Deacon squeezed Jesimaes neck a little harder stopping the flow of blood to his brain and air into his lungs.  When he felt Jesimae begin to lose her consciousness he forced his cock into the teenagers asshole.  The muscles of Jerrods ass fought the invasion, but ultimately lost.  The outer sphincter gave in first followed by the inner sphincter and when The Deacon felt the boys ass give way to his hard cock he jammed himself into the boy.  When he bottomed out, he released his hold on Jesimaes neck.  The walls of Jesimaes bowel stretched and contracted to grasp the tube of black cock that had invaded its space.  The Deacon knew he had just found one of if not the perfect male pussy to fuck for as long as the bitch could take him.
Jesimae took a deep breath and let out a blood curdling scream.  She screamed for him to take his cock out of her ass.  She begged and pleaded.  The only answer she got was a slap on the back of her head and the feeling of his cock slipping out her ass and being rammed back in.  The Deacon did not say a word as he fucked his teenage cellmate.  He didnt bend Jerrod over, but kept him straight up against the wall and used his strength to push Jerrod off his feet.  The Deacon leaned the top half of his body against the slight frame of the boy and used his cock as if it was a picture hanger to keep Jerrod/Jesimae off his feet.  It didnt take long for him to feel the dribble of blood from the boys ass.  He knew he tore his asshole and hurt him, but it didnt stop him from corn-holing the yowling teenager.

The Deacon took no solace on the boy.  He got the crying bitch into a comfortable position and just fucked the shit out of the boy.  He loved the feel of his tight asshole squeezing his powerfully hard cock as it slid in and out of the torn asshole; lubricated by the blood that was coating the inner walls of his lower bowel.  Jerrod finally gave up fighting the rape of his ass and just quietly cried as he felt The Deacons cock use his asshole and lower bowel as a pussy.  He could feel the mans cock in his belly when The Deacon was bottomed out inside him.  He had the terrible feeling of having to take a shit and couldnt get rid of it as The Deacon continued to fuck him.  The pain was not turning into pleasure as hed heard from other men who were anal fags.  Jerrod suffered emotionally, psychologically, and physically as his ass was pummeled by a seven foot three inch nigger with a fourteen inch cock.

All Jerrod could do was moan, Please  No Stop over and over again.

The Deacon tuned everything out.  All he wanted was to get his nut and deposit it in Jesimaes pussy-ass.  He fucked Jerrod/Jesimae nonstop for a good fifteen minutes before he felt his body begin to tell him he was going to pop his nut.  He didnt take long strokes but began to keep most of his cock in his bitchs ass.  He pressed hard against Jerrods/Jesimaes backside.  He didnt moan or cry out that he was going to orgasm.  He pulled about half his cock out of his cellmates ass, rammed it back in so hard Jesimae cried out in pain, and The Deacon discharged seven thick ropes of his hot man seed into the crying teenagers lower bowel.  The Deacon noticed that Jesimae did not physically react at all to feeling his cock pulse, throb, and explode inside her.  Thaddeus Washington just wanted to spend the rest of the day and night with his cock embedded in his cellmates now christened pussy-ass.  When he got his legs back he held Jesimae close to his body, his cock still hard and embedded, saddled over to the bunk bed, and without having to remove himself from the tight ass that was surrounding his cock, he placed Jesimae in the bunk on her stomach and began to fuck her again.

The only thing on The Deacons mind was how many times he could fuck Jesimae before he couldnt keep it up anymore; while the only thing Jerrod/Jesimae thought about was how he/she was going to survive four days locked in a cell with the possibility of having a fourteen inch cock up his ass the whole time.  As he lay in the lower bunk moaning in pain, The Deacon used his weight to keep him still as he ever so slowly but not gently continued to fuck his eighteen year old cell mate and new prison wife.  The only benefit to Jerrod was if he turned his head to look at the other side of the cell he could see the clock radio which displayed the date and time.  At least hed be able to count down the time until The Deacon released him from his hold and freed his now used anus from the implement of his torture.
