Prison Dolls Ch. 01

Representatives from the DoC were required to conduct site visits to the prison but the Warden was given advance notice and ensured that everything appeared hunky dory and above board. The inspectors were led around the dorms where they encountered smiling inmates, into the kitchen where sumptuous food was being prepared, into classrooms where inmates were undertaking vocational education and out to the prison farm where the prisoners worked hard but were content to do so because they were paid reasonably.

They were taken nowhere near E Wing and if questioned about it the Warden advised that E Wing was unpopulated and being surplus to requirements, remained abandoned but could be activated if required.

One might question why the inspectors, who knew that most prisons suffered from overcrowding, swallowed the Warden's story but the inspectors were incentivised not to ask too many questions. The prison was well run, the inmates were content and Wakefield Services had an exemplary record. No need to rock the boat. Discreet payoffs were being received by those who needed to be paid and those who had the occasional pang of guilt were consoled that no one was actually being hurt. What was happening inside Brentwood was victimless crime.

Robert Valentine

Robert Valentine lived in a big fancy house and he and his wife drove big fancy cars and they wore fashion-label clothes. They vacationed in Hawaii or Thailand or Bali when they went seeking the sun, or Aspen or Japan or Austria when they went seeking snow. Their daughter Charlotte attended a private college and drove a modest BMW, if there was such a thing as a modest BMW. They moved in the right circles, went to the right parties and had friends who did the same.

All that came to an abrupt end when agents from the Georgia Bureau of Investigation raided Robert's house early one Sunday morning. Thankfully Charlotte was away for the weekend with her girlfriends and didn't have to witness her father being led away in handcuffs by two brawny Georgia State Patrol Troopers who were assisting the GBI. Robert's wife Mandy did have to suffer the indignity of watching the GBI ransack their house searching for corroborative evidence to support the almost iron-clad case the GBI already had against Robert Valentine.

They found nothing. That was until one of the agents who had worked construction looked at the bookcase in Robert's home office and thought it didn't look right. The agents brought in some tools and removed the books and under the bottom shelf they found two concealed pins. After some work with a screwdriver the pins were removed and the bottom two shelves, which were hinged, were pulled loose. Behind the bookcase a treasure-trove of evidence was discovered including nearly two hundred and fifty thousand dollars in cash, three burner phones and two USBs containing documents proving Robert Valentine was guilty of fraud, insider trading and embezzlement.

Robert Valentine copped a plea and was sent to Smith State Prison. His assets seized and most of his legitimate funds used to pay for the best criminal attorneys available, the big house, flashy cars and private schools disappeared as did the Valentine's affluent and influential friends.

His lawyers earned their money and parlayed his plea bargain so that Robert spent only eighteen months in Smith State Prison before he obtained a transfer to the minimum security prison known as Brentwood Correctional Facility. In Smith Robert kept mostly to himself and was a model prisoner. By the time he arrived at Brentwood, Robert was determined to obey the rules implicitly and just do his time. Although he was mostly left alone in Smith State Prison he had witnessed brutality and debasement and had no wish to ever return.

Life at Brentwood was a breeze compared to the State Prison. It was almost a holiday camp. Brentwood housed inmates who had a minimal criminal history and inmates with no history of violence; a high percentage of the inmates had been convicted of corporate crime. As such, Brentwood was known as a 'white-collar prison' and although it was run by the State it was nicknamed 'Club Fed'.

It wasn't long after his arrival at Brentwood that Robert became aware that something wasn't quite right. Rumours circulated about some bigwig mafia types who lived in a wing that inmates had nicknamed 'Seg'. Apparently they lived in luxury and did whatever they wanted to and they really ran the facility because they had a controlling interest in the private company that operated the prison. They had bribed or blackmailed senior management in the DoC and had clout with a bunch of statesmen and judicial bigwigs.

Robert felt the whole story seemed a little farfetched but something was going on in Seg. Not that he cared. Robert just wanted to do his time and get out of jail.

But... one day he was sitting by himself in the mess hall and he was approached by Tig and introduced to Allie Katt and his life was never the same after that day.

A New Prison Doll Is Born

Everything was running smoothly until Allie's release date approached. When Allie was released from prison the crooks in Seg would be left with only Marilyn to satisfy their desires and Tig knew that was not sustainable. He needed to find another prison doll to take Allie's place.

He thought briefly about getting Allie's sentence extended but that would require Allie being found guilty of a criminal offence or committing a major infraction of the prison rules. It would be easy to set up but the consequences risked sending Allie back to a medium security facility which would be counterproductive. In the end the answer was simple. Tig told Allie to find a replacement or risk not getting released or possibly facing worse consequences on the outside. As an incentive, she was told that a very well-paid position awaited her outside the prison hosting the drag show at one of the Siceresso's nightclubs.

Allie had no choice but to find a suitable candidate. But who?

The candidate would likely have to come from D Wing because of its close proximity to Seg. Allie carefully considered each of the inmates and ruled out most of them because of their age, physical presentation or demeanour. She would not be fortunate enough to find another gay inmate who was suitable so whoever she selected would have to be coerced.

Allie settled on Robert Valentine. He was in his early thirties with brilliant green eyes and an impossibly handsome face. His hair was long and scraggly, he wore a close-cropped beard and he was a little pudgy but he was an uncut gem waiting to be turned into a valuable jewel. He was a loner who kept to himself which also made him an ideal candidate.

"Robert Valentine. Do what you have to convince him and I will turn him into a prison doll for you before I leave," Allie said to Tig.

Did Allie feel sorry for Robert? Not really. It was him or her and Allie was looking forward to release. Most drag queens, although almost exclusively gay, are not transgender women but some of them find themselves on the trans spectrum and many have transitioned. Allie had struggled with gender dysphoria and had recently made the conscious decision that she was in fact a transgender woman and intended to begin her transition on release from prison and live her life as a woman.

If that meant someone had to take her place satisfying the sexual urges of the men in Seg so be it!

Robert was sitting in the mess hall when Tig sat down beside him.

"Bus that tray and follow me," Tig growled.

Tig was six foot six inches of solid muscle with a broken nose on a hard but handsome face and presented a demeanour that he was not to be fucked with.

Robert bussed his tray and followed Tig to his room where Tig closed the door and told Robert to sit. Tig sat uncomfortably close to Robert whose head was spinning with confusion. What could Tig possibly want with him?

"Look," Tig produced a very illegal cellphone and held it up to Robert's face.

Tig began to swipe through a series of digital images: Robert's wife Mandy out front of her small rented two-roomed house with painted block walls, concrete floors and a zinc roof where she lived with their daughter Charlotte. Mandy was opening the door of her three-year-old preowned Volvo for Charlotte to climb in.

Next was a series of images of Mandy dropping Charlotte off at Middle Georgia State University. Charlotte lived with her mother because they couldn't afford the residency fees. What followed were a series of pictures of Charlotte walking down the street alone, sitting in a coffee shop with her friends, playing volleyball in her tight little shorts and crop-top, dressed in a cheap micromini dress dancing with a boy at a college mixer and finally wearing a yellow waitress uniform that clung to her figure and showed off her trim ass and long legs clad in cheap tan pantyhose. She was serving truckers at a truck stop restaurant where she worked part time to supplement her mother's meagre income. Charlotte was showing off her assets to pump up her tips.

Robert thought his heart was about to explode but then Tig showed him another series of pictures: Mandy parking her Volvo in a dark multi-story parking garage. Mandy dressed in her cheap business suit entering the elevator in the office block where she worked as a secretary. Mandy eating lunch by herself in the office block cafeteria and shockingly, a zoomed-in, up-skirt picture of her pristine white panties. The seam of her pantyhose ran down the centre of her pudenda.

"I have more but you can see where I'm going with this can't you Robert?" Tig sighed.

"I can have your wife and daughter abducted anytime I want. It would be so easy. Maybe get them when Mandy picks up Charlotte after school. Net them both together," Tig smiled evilly.

"Of course their abduction and murder will not be traced back to the Siceressos. I'll contract a couple of sicarios through my cartel contacts in Miami. Those guys are bad asses. Imagine what they will do to your beautiful wife and pretty daughter before they kill them?" Tig's smile widened.

"I'll get it on video so you can see it," Tig put the phone away and gripped Robert by the arm.

Robert thought that his heart was going crash out of his chest. His head was spinning and he could hardly breathe.

"Stay with me Robert," Tig squeezed Robert's wrist.

"None of that needs to happen, in fact you have the opportunity to provide a better standard of living for your wife and daughter," Tig let go of Robert's arm when his breathing was finally under control.

"What do you want from me?" Robert lowered his face into his hands and sobbed.

"You're not going to believe me so in a few minutes Allen Kettering is going to come into the room and I'll leave the two of you alone while all is explained," Tig stood and strode out the room and Allen Kettering entered.

"What the fuck is going on?" Robert asked Allen.

"Do you know me?" Allen replied.

"I've seen you around. I've heard rumours but I keep to myself so I don't gossip," Robert said.

"Ok. You've heard rumours. Come with me," Allen opened the door indicating for Robert to leave.

"I need to be back at work. I need to catch the bus back to the farm," Robert said with as much defiance as he could muster, which wasn't much.

"I don't know what Tig showed you and I don't want to know but Tig says you will be compliant from now on. You don't need to be anywhere except with me for the rest of the week. Your work duties are suspended for now," Allen beckoned Robert forward.

"What about my commissary? How am I going to earn?" Robert whined, which sounded self-pitying and he hated himself for it.

Allen laughed.

"You're commissary will be taken care of and starting next week a steady flow of income will be provided into a numbered account. What you do with it is up to you. Right now you need to know that Tig speaks for the Siceresso crime family and they don't make idle threats. Get your ass down to my dorm room right now," Allen spoke authoritatively and Robert complied.

"Sit down and pay attention," Allen ordered and Robert sat in the chair next to Allen's desk.

Allen closed the door then walked over to his wardrobe and opened it.

"Watch and learn," Allen said, his voice changing almost into a falsetto.

Robert sat and watched Allen, dumbfounded, fascinated and he had to admit a little excited, as Allen transformed into a woman. The transformation was amazing; not only the physical appearance but the total metamorphosis. Allie was a different person: her bearing, demeanour, her speech, her walk, her posture and mannerisms were all totally feminine.

If he didn't know better Robert would swear that the person standing before him was a beautiful, alluring woman.

He was still confused and frightened but the bizarre sorcery he had witnessed pushed the thoughts of anger, fear and desperation aside and replaced them with curiosity, bewilderment and wonder.

"Hi, I'm Allie Katt," Allie struck a pose and smiled at him.

"Pretty fucking amazing Allie, but you still haven't told me why I'm here or why Tig is threatening to have my wife and daughter raped, tortured and killed if I don't do as you say," Robert was finally able to speak.

"You're here because you are the new me. You are going to take my place," Allie winked at Robert.

"I don't know what the fuck you are talking about," Robert replied, still bamboozled.

"I'm going to turn you into a hot transvestite and you are going to, shall we just say for now, work for the Siceressos in Seg," Allie grinned at him.

"I still don't know what the fuck you're talking about," Robert slowly shook his head.

"You told me that Tig has threatened to have some people do the direst things to your wife and daughter and then kill them. Over the next week, if you ever have doubts or concerns about what we are doing, just know that those threats are real. Now strip!" Allie ordered.

"What?" Robert was still confused.

"Get undressed darling and let's see what I've got to work with," Allie strode over and pulled Robert out of his seat.

Taking for granted that everything Tig and Allie had said to him was true, Robert took off his clothes. Being in a prison with shared ablutions Robert was used to being naked in front of other inmates.

Allie cast a critical eye over Robert.

"Not bad. You're a little pudgy but you have wide hips, a nice ass and long legs and your face is amazing. I bet you've broken a few girls' hearts," Allie walked slowly around Robert considering him carefully.

Robert had broken a few girls hearts and even though he was married to Mandy women still came onto him because of his handsomeness. But right now that was moot. Robert was still trying to get his head around what Allie was saying to him.

"Put this on," Allie handed Robert a satin robe she had taken from the wardrobe.

The satin felt delightfully slinky against his bare skin but Robert didn't have time to luxuriate in it. Allie grabbed a toiletries bag and a towel and led Robert to the ablutions. Everyone else was at work and there was not a corrections officer in sight. They had D Wing to themselves.

"Shave off that fluff and then shave again; as close as you can," Allie handed Robert a razor and a can of shaving crème.

Robert complied because he had to. He changed the blades on the razor before shaving his face a second time. It was the first time he had seen his face without a beard since he had been incarcerated and he was amazed at how younger and handsomer he looked without it. Allie was impressed too. Turning this pretty boy into a pretty girl should be easy.

"You have fuck-all body hair but shave it anyway. All over, from your chest to your toes," Allie ordered and lit up an illicit cigarette while Robert complied.

"Sack and crack too. I'll give you some Veet later to depilate your perineum," Allie quipped.

"My what?" Robert asked as he carefully shaved his scrotum.

"Your perineum... your fucking taint," Allie explained.

"Is this necessary?" Robert whined.

"Is it necessary for your wife and daughter to go on breathing?" Allie replied and immediately regretted saying it.

She wondered what type of person she had become but she had her own problems and the only solution was to turn Robert into a prison doll to take her place.

When he was finished shaving, Robert stood at the sink with a hangdog expression on his face that for an instant made Allie feel sad.

"You keep yourself like this from now on. Body hair is the enemy of the female impersonator," Allie quipped and pushed Robert toward the door.

Back in her room Allie made Robert sit before the vanity mirror mounted above her desk.

"I'll get Tig to arrange to have one in put in your room tomorrow," Allie said, referring to the mirror, while she took a large cosmetic case out of her wardrobe.

She arranged the cosmetics on the desk in front of Robert.

"Watch and learn," she sighed, gathering Robert's hair into a ponytail to keep it away from his face.

She spent the next two hours applying cosmetics to Robert's face, removing the makeup and then having Robert do it repeatedly until Robert was somewhat proficient.

"You'll get better at it with practice and you will develop your own look," Allie said, standing behind Robert looking at his face in the mirror.

Robert couldn't talk. He was amazed at the transformation. He had the face of a beautiful woman. The makeup enhanced his almost perfectly symmetrical face. The eyeliner, mascara and eyeshadow embellished his large green eyes. A light coating of rouge defined his slender nose and pronounced cheekbones and the lipstick plumped his lips into a seductive bow. Allie used tweezers to shape Robert's eyebrows into soft, feminine arches.

"I'm not going to fuck with your hair today. I'll have the hairdresser cut, colour and style it tomorrow," Allie said matter-of-factly as she let out Robert's ponytail, bunched his hair and pulled a stocking cap over it to keep it in place.

She placed a raven-haired, shoulder-length bob on Robert's head, showing him how to adjust the elastic straps at the rear, set the clips in his scalp and finally she showed him how to pin it in place so it wouldn't move. She brushed it and fussed with the bangs and stood back so that Robert could see the results.

Now Robert really was dumbfounded. Staring back at him in the mirror was one of the most enchanting and vivacious women that Robert had ever seen.

"Hello Bobbie," Allie smiled.

"You're fucking gorgeous. You're going to be fucking perfect!" Allie's face was plastered with a self-satisfied grin.

"I can't believe that is me," Robert was still astounded.

"It isn't. That's Bobbie, a totally different person to Robert. You're going to not only transform your face; you're going to have to transform everything about you. You are going to have to forget about Robert when Bobbie is required. Call it a survival skill, call it evasion motivation, call it having a dual personality... call it what you will but you need to commit to being Bobbie," Allie said which Robert found daunting.

"From now on whenever you transform I am only going to call you Bobbie and you are going to call me Allie," she fussed with Bobbie's hair as she spoke.

"What do you mean, when Bobbie is required?" Bobbie asked.

Robert was trying to think of himself as Bobbie and looking in the mirror helped.

"Tig will tell you or Marilyn will. But let's not get ahead ourselves, you've a long road ahead of you," Allie helped Bobbie out of the chair and had Bobbie stand before her.

"Who is Marilyn?" Bobbie asked but she was ignored.

"Look here," Allie hiked up her pencil skirt and showed Bobbie her pudenda sheathed in silky pink satin panties.