Bobbie Valentine – Pretty Boys Make Pretty Girls

Robert Valentine awoke and opened his eyes. He stared at the ceiling. On the his first day at Brentwood Correctional Facility Robert had noticed a crack in the ceiling plaster and over the months the crack had slowly elongated, snaking its way towards the light-fitting in the centre of the ceiling. That’s how Robert imagined his life: slowly crawling towards the light… slowly crawling towards freedom. When the crack reached the light, he would be released from prison and the nightmare would end.

But the crack had a long way to go until it reached the light-fitting and today he would once again live the ambiguity that his life had become.

He got out of bed and glanced around his room. It wasn’t really a cell. It was more like a cheap motel room, inexpensively but practically furnished. There were no bars on the windows, no unannounced head counts by brutal prison guards, no fear of being beaten for committing a misdemeanour or an unintended sleight. But Brentwood was still a prison. It might be a minimum security facility but there were rules: both written and unwritten. Rules imposed and enforced by the Department of Corrections and rules imposed and enforced by some of the inmates.

Robert made his way to the ablutions where he used the toilet, shaved and showered. None of the other inmates spoke to him. Not because they were scared of him but because they were scared of who owned him.

Robert ate a frugal breakfast in the mess hall sitting across from Maurice Shrew. Nobody else sat at their table and they spoke hardly at all. Maurice and Robert had nothing in common except that they were both living the same duplicity, although Maurice seemed to like the duplicity a lot more that Robert did.

“Same time tonight. Both of you,” Tig Hansen whispered out the side of his mouth as he walked past their table.

“See you later honey. Looks like we’re both gonna be busy,” Maurice said as he stood and bussed his breakfast tray.

Robert winced. He knew what Maurice meant and Robert tried not to think about what would happen tonight… or most nights for that matter.

In the morning Robert worked in the laundry operating the industrial washers and dryers; washing, drying and folding sheets and pillowcases and prison uniforms. Maurice worked on the farm but he didn’t get his hands dirty. Maurice Shrew handled the bookkeeping and administration for Brentwood Prison Farm which propagated organic produce sold both locally and shipped interstate.

The town of Brentwood, nestled in a fertile valley in the Appalachian Mountains, was known for its pristine hills, lush forests, and beautiful parks and greenways. The temperature was mostly cooler than the humid subtropical climate in the southern parts of the state. The community prided itself on maintaining its natural beauty and preserving its rich history. The correctional facility was located in the State Park discreetly located away from the main population centre but a good many souls from Brentwood were employed by the DoC and worked at the prison.

It was easy work because the facility was minimum security, housing non-violent low-risk prisoners who pretty much ran the facility themselves with nominal supervision.

Robert sat with Maurice during lunch but didn’t eat. Neither did Maurice but attendance at the lunch-hour meal was compulsory because that was when the only head count of the day was conducted. Robert had lost twelve pounds since he came to Brentwood despite the good food. Robert maintained a strict diet and exercise regimen not by choice but because he had to.

In the afternoon he walked five miles around the running track maintaining a brisk pace. He spent some free time in the library where the prisoners had internet access but with blocking and filtering software that prevented the prisoners from accessing unapproved websites. They were allowed to maintain personal email accounts which were monitored by the DoC for content.

He emailed his wife Mandy and told her he was looking forward to her visit on Saturday and asked her to pass his love onto their teenage daughter Charlotte. Charlotte would not be visiting. Robert perused some cosmetic and lingerie sites and placed an order with Tig Hansen. He ordered a pair of high heels that he had been looking at for several days and finally decided that he wanted them. He felt wracked with guilt for doing so but he knew that one day his need for lingerie, high heels and cosmetics would be over… his release date.

Robert did not attend the evening meal as it was not compulsory to do so and many inmates ate food from the commissary in their rooms or in the common rooms while they watched television.

Robert did not eat commissary food nor watch the television. He began the ritual.

He went down to the ablutions and hung an enema bag on the shower head and cleaned himself internally, hating every second of it but knowing the necessity of it. He showered, brushed his teeth and used mouthwash and examined himself critically in the mirror. His body was slim with wide hips and long legs without a skerrick of hair below his arched eyebrows. He plucked a few rouge hairs from his legs and checked his armpits. They would last another few days before they needed to be shaved.

Robert shaved his face closely and brushed out his shoulder-length jet-black hair. During the day it was tied in a man-bun but now it was perfectly straight and centre parted with bangs. His transformation into Bobbie had begun. One door in his mind slammed shut and another opened allowing Bobbie to assume control of his psyche. Living a double-life was the only way Robert and Bobbie could survive together. They were two different people with different minds and souls but they shared the same body.

Bobbie made her way back to her room ignoring the knowing looks from some of the other inmates she passed in the corridor. They knew better than to engage with her.

Back in her room Bobbie opened a drawer in her dresser and took out her cosmetics, deodorant, perfume and other female essentials. She hung up her towel and draped herself in a silk dressing gown and began working on her face.

There is a saying in the Trans and gay community: a pretty boy makes a pretty girl. Robert was incredibly handsome and almost every day he wished that he wasn’t. His handsomeness was to a large extent responsible for the nightmare his life had become. His face was almost perfectly symmetrical with large green eyes, a slender nose, pronounced cheekbones and plump lips. His eyebrows were carefully shaped into soft, almost undefined arches.

Concealer, foundation, rouge, eyeliner, eyeshadow and finishing powder transformed Bobbie’s face from pretty to stunning. A final coat of Rouge Dior Forever Lipstick, $65 a tube thank you very much, applied to Bobbie’s full lips completed the transformation.

Bobbie fussed with her hair and makeup a little so she looked perfect and sprayed herself liberally with Dior Poison perfume. She had laid out her clothing for the evening on the bed but first she stood and winced a little as she tucked her testes up into her inguinal canals, pulled back her penis and empty scrotum and taped them along her perineum with surgical tape. When she stepped into her red satin hipster panties and smoothed them out she had a Vee between her legs that any drag queen would be proud of.

Tucking was in important part of Bobbie’s transformation. The men she would be meeting this evening would not take kindly to any imperfection that spoiled the illusion that Bobbie was anything other than a beautiful seductive woman.

She rolled a pair of fifteen-denier, flesh-toned, shimmery, hold-up stockings up her long legs and smoothed out any wrinkles, delighting in the sensation of the delicate hosiery on her shaved legs despite trying to supress the feeling. Bobbie shimmied into the brassiere that matched her panties. It was A-cup and worn more for aesthetic than function. When she first became Bobbie she was given lifelike silicone breastforms to pad her bra but her masters didn’t like them. They gave her a flattering shape but they got in the way when things heated up.

Bonnie slipped into a red low-cut, knee-length, satin sheath dress. She performed the necessary acrobatics to zip the dress closed in the back and stepped into a pair of red fuck-me pumps. She accessorised with good quality costume jewellery: two rings, matching bracelets on each wrist, earrings and a choker. Sliver set with emeralds to match her eyes.

She picked up her red leather handbag and gave herself a final onceover, set her resolve and left her room. Most of the doors to the rooms were locked but a small group of inmates were in the common room playing cards and board games and the door opened a crack and an inmate peeked out to see what Bobbie was wearing tonight. The men knew better than to make any comments or slurs. Those who did not approve of what Bobbie was doing simply kept schtum.

There was not a corrections officer in sight.

She exited the dormitory and made her way along the path to the building occupied by the men who really ran Brentwood Correctional Facility, her high heels click-clacking on the concrete path lit by LED edge lighting. She shivered a little in the cool crisp air.

She tapped a code into the numeric keypad next to the door using her French-tipped nails which she went to great pains to keep perfect by wearing gloves when she did her chores or handled chemicals. She moisturized her hands and cuticles regularly to keep them healthy and prevent lifting. She took the nails off only when Mandy came to visit.

The door opened and Bobbie entered a world unlike any other imaginable.

“Joey wants you right away,” Tig Hansen met Bobbie at the door.

Tig was the muscle and logistics guy for the men who lived in Seg.

Seg was short for Segregation which was a misnomer. There was no Seg in minimum security prisons. If you fucked up bad enough to be sent to Seg you got sent back to real prison to finish your time. Seg was the nickname given to E Wing which was the block that held the five organised crime identities who had no business being incarcerated at Brentwood Minimal Security Correctional Facility. You got into Seg by invitation only. Even the Warden called ahead before she came to visit.

Tig nodded at Bobbie and she nodded back and walked down to the second door on the right and tapped lightly.

“Come in doll,” Joey Malzone called through the door.

Bobbie entered and was greeted by Joey Malzone who was naked except for a silk dressing gown and expensive slippers. Soft classical music drifted across the room from Bang and Olufsen speakers. If Bobbie’s room resembled a cheap motel room, Joey Malzone’s room resembled a suite at the Plaza.

“Come here doll,” Joey opened his arms wide exposing an expansive hairy chest and considerable gut under which hung a substantial semi-erect penis.

Bobbie set her resolve and stepped into Joey’s outstretched arms and he pulled her into his embrace. She put her arms around him and pressed herself against his body and put her mouth on his and he kissed her passionately, his lips thick and his tongue meaty and wet. She moulded herself to him, feeling his erection pressing into her belly.

Being summoned to Joey Malzone’s room as soon as she arrived in Seg meant only one thing and Bobbie knew what to do. She kissed him with the same passion that he was expressing, sliding her tongue around his mouth and lifting one leg to rub her nylon-sheathed thigh against his thick hairy leg. She snaked a hand down his body, caressing his hairy chest, across his gut and down between his legs, cupping his scrotum; gently fondling the hairy sac.

She could feel his manhood on her wrist, already leaking warm slippery precum.

“You look gorgeous tonight, as always, and you smell wonderful,” Joey held her at arm’s length and studied her.

He pulled Bobbie close, squeezed her buttocks and grinned at her.

In her heels, Bobbie was the same height as Joey. He had a big head sitting above a bull neck. His face was dominated by large sensuous lips, a big fleshy nose and big sad brown eyes framed by bushy brows and dark curly hair. He was not unattractive in a cuddly teddy bear kind of way but this teddy bear had been a ruthless killer when he was a soldier in the Siceresso crime family before he worked his way to the top.

“And you are handsome as always,” Bobbie replied, knowing how to play the game.

She leaned in and kissed him softly on the lips and then nuzzled his thick earlobe.

“Is that Stefano Ricci you’re wearing?” she caressed his bull-neck with her lips and inhaled the expensive cologne.

“Yeah. Look doll I don’t wanna keep you from the party. You know what to do,” Joey pressed lightly but insistently on her shoulders.

Bobbie knew exactly what to do.

She slowly dropped to her knees, kissing him passionately on the lips before beginning her descent, slinking her mouth down his hairy torso, stopping briefly to circle his nipples with her tongue, nipping each of them playfully. Her fingers stroked his flesh as she lightly dragged her fingernails down his body until she was kneeling before him; his wicked manhood level with her face.

“Yes doll,” Joey sighed as she took his engorged manhood in her mouth.

He placed a hand on each side of her face but he was gentle; merely holding her still while she fellated him, pushing his thick fleshy protuberance in and out of her mouth.

Bobbie’s lips circled his shaft while the tip of her tongue lashed his glans, concentrating on his fraenulum so that he experienced maximum pleasure. Bobbie had learned how to perform fellatio and turned it into an art form. She was an expert fellatrix because she knew that if she was able to satisfy a man with her mouth he might be less likely to want to fuck her and he’d cum in her mouth instead of her ass.

She suckled Joey’s fat cock, exercising a breathing pattern she had mastered so that her subject received maximum stimulation without gagging her. She took his cock deep into her mouth, exhaling through her nose and calmly held her breath as Joey pushed his cock into her throat. As Joey began to fuck her face she breathed in and inhaled through the sides of her mouth suppressing the gag reflex.

Bobbie hated that she experienced feelings of power and exhilaration while she serviced her masters. Her body often betrayed her and she regularly felt sexually gratified while she performed the services she was obliged to provide but she had learned quickly that pleasure helped suppress revulsion. It was a mask she could put on and take off at a whim while she presented herself as Bobbie. It was a survival technique that kept her sane.

Bobbie cupped Joey’s scrotum and tickled his testes with her fingernails while her head bobbed up and down on his engorged phallus. She kept her tongue flat and used the tip of it to lash at his fraenulum as his cock slid in and out of her lipsticked lips, gliding over her tongue and into her throat. Deep throating was her specialty.

“Yes doll, yes…” Joey moaned and she felt him release.

Her mouth was suddenly filled with thick creamy semen as Joey ejaculated. His cock was no longer in her throat and she clamped her lips around the shaft and lashed at his glans with her tongue as his cock juddered and deposited his seed inside her mouth. She held onto his thigh with one hand while the other caressed his sac, encouraging him to express every drop of his load in her mouth.

Bobbie could feel her cock becoming bloated as feelings of sexual ascendency surged through her subconscious but she shook them off and concentrated on the task in hand which was providing this thug with as much sexual gratification as he could endure.

Joey held her head still and thrust his cock in and out of Bobbie’s mouth as she struggled to swallow his offering. Her mouth filled and she swallowed and then it filled again and she swallowed that. Joey had been saving his load for her.

With a final shudder and a mighty roar Joey’s climax peaked and began to subside and he ripped his cock from her mouth and pushed her face away from his groin. Bobbie suspected that Joey felt pangs of post-coital regret immediately after he orgasmed but they soon dissipated. For an instant after climax Joey probably actualised that his prison dolls, Bobbie Valentine and Marilyn Shrew, were men presenting as women but the notion passed almost instantly.

Bobbie struggled to her feet and without a word she walked over to the ensuite bathroom where she used Joey’s mouthwash to freshen her breath and dug in her purse for foundation, powder and lipstick to fix her face. She took the preloaded lube applicator from her purse, eased her panties aside and pressed the nozzle into her anus and slowly depressed the plunger. She knew that it was going to be a busy night. When she returned Joey was pouring himself a tumbler of Dalmore single malt Scotch whisky. He didn’t bother to offer her a drink. She was needed elsewhere and there would be plenty to drink there.

“Come here doll,” Joey opened his arms once again and Bobbie snuggled up to him and kissed him.

The kiss was perfunctory, his passions were sated and he wanted her gone.

“Thanks doll,” he patted her on the ass and dismissed her, gently guiding her towards the door.

One down, four to go, if all the men wanted sex tonight. Of course Marilyn would pull her weight so Bobbie wouldn’t have to service all of them she thought to herself as she stepped into the corridor and smoothed her satin dress.

There were five other identical rooms, three either side of the corridor, and four of them were as palatial as the one occupied by Joey Malzone. The sixth room was an office used by the Seg inmates where they maintained control of their criminal empire. The end of the corridor opened out into a room that was as grandiose as any first class airline lounge: a large flatscreen television dominated one wall with a state of the art sound system. The television was linked to cable, satellite and most of the pay-for-view webcast services. The furniture was modern, comfortable and expensive. Behind the lounge was an impressive well provisioned kitchen. Inmates in Seg did not eat, work or recreate with the other prisoners. They lived alone in the lap of luxury.

Adjoining the lounge was a recreation area that resembled a nightclub or sports bar that they called the playroom. There was a pool table, video games, and most forms of entertainment one would find in an upmarket tavern or country club.

Sal Siceresso, Tony Siceresso, Petey Gruffalo and Mike Giacomo occupied two overstuffed sofas sipping cocktails. Marilyn Shrew sat between Tony and Mike dressed in a black sequined cocktail dress. Her makeup and hair looked a little messy and Bobbie rightly assumed that Petey and Mike had been messing around with her. She was sipping a frozen margarita through a straw and seemed perfectly happy.

“Here’s my girl,” Sal and Petey both stood so that Bobbie could squeeze in between them.

She kissed them both on the cheek and sat down.

“Joey’s got something on this evening sweetheart so he won’t be joining us,” Sal smiled at her.

“Bobbie visited Joey in his room on the way here,” Tig Hansen piped in from the door.

Sal gave Tig an unsavoury glare and Tig wandered off to the office. Tig’s explanation was not required.

“Let me get you a drink doll. How about a margarita?” Tony, the younger of the two Siceresso brothers, asked.

“They any good?” Bobbie asked Marilyn who nodded appreciatively.

“I’ll take one sugar,” Bobbie smiled at Tony and she stroked his shoulder lovingly.

Tony went to the bar and the whirr of a blender filled the air as he made the frozen margarita.

Bobbie leaned into Sal and they kissed a little and Sal felt her up under her skirt, avoiding her crotch.

Over the last three months Bobbie had been fucked by every man in the room on numerous occasions and she knew their personalities, peccadillos and perversions. She knew how to deal with them individually and as a group and she played her role to perfection, as did Marilyn. It wasn’t that hard to do: look and present femme, dress pretty and sexy, be subservient, never deny them anything they wanted, be enthusiastic and most of all keep your mouth firmly zipped outside of Seg.

Sal wasn’t very enthusiastic which didn’t surprise Bobbie. Sal was the oldest and even though he liked sex, his appetite was waning. The other four men in Seg nailed Bobbie and Marilyn pretty much every night but Sal was about a once-a-week man.

Tony came back and offered Bobbie her drink and she gulped it down quickly, giving herself a ‘brain freeze’ which amused everyone. Sal stood up and apologised that he had things to do and he went off to the office where he was joined by Joey Malzone. They closed the door leaving Tony, Petey, and Mike to party.

Everyone drank a lot, especially Bobbie who used the alcohol to numb her senses and lift her enthusiasm for the evening ahead. They chatted about current events, sports and entertainment, everything but business or anything to do with Brentwood Correctional Facility. For the men in Seg, Brentwood might not even exist. They lived in their own world, unencumbered by their incarceration except for the fact that they couldn’t leave.

The men took turns dancing with Bobbie and Marilyn and as the booze flowed the men became more ribald, feeling up the girls and smooching with them.

She and Tony were close-dancing when Tony whispered something into her ear.

“I’m going with Marilyn tonight honey; I hope you won’t be disappointed,” he squeezed her affectionately.

Bobbie was disappointed but there was no way that she was going to show it.

Eventually Marilyn went into one of the bedrooms with Tony and Mike and Petey led Bobbie to his room.

He closed the door and closed in on Bobbie. He pulled her tightly into his arms and kissed her. Bobbie returned the kiss; driving her tongue into Petey’s mouth the way she knew he liked it. Petey liked to treat Bobbie and Marilyn like whores, which essentially they were.

“Take it out babe,” Petey whispered and guided Bobbie’s hand to the bulge in his slacks.

She obliged and unzipped him and began to stroke his cock to full tumescence while she kissed him.

“That’s it babe. You know what to do next,” Petey growled.

Bobbie did know what to do next and she dropped to her knees and began to suckle his cock, sliding her lips along the shaft while her tongue tickled his fraenulum. She swallowed the pre-ejaculate that leaked from Petey’s cock, it was sweet and viscous and not unpleasant.

She worked her mouth on Petey, quickening the pace and then slowing down. Taking his cock out of her mouth and rubbing it on cheek while she gazed up at him.

Petey liked to look at his bloated manhood resting on Bobbie’s pretty face. Sometimes he would cum this way, holding her head tight while his scalding spunk spattered across her cheeks, into her emerald green eyes and onto her glossy black mane. Feeling her squirm as the creamy dollops stung her eyes and ruined her makeup. He’d rub his ejaculating cock all over her face, shoving it into her red lipsticked lips as the final spurts erupted from his juddering cock, watching her throat work as she swallowed his offering, hearing her whimper like a teased kitty. It felt empowering.

He watched Bobbie expertly manipulate his cock and delighted in the feelings she elicited from his penis with her fingers and her mouth until he was close to orgasm.

But Petey had other plans.

Whenever Bobbie got him close to extremis he’d lift her to her feet and kiss her, slapping her hand away from his cock until he felt the need to ejaculate subside. Then he would push Bobbie to her knees and she would take up where she had left off, suckling his manhood, rubbing it on her face then engulfing it, then slavering the turgid flesh with her mouth and tongue.

Bobbie would repudiate it if anyone claimed that she found the subjugation somewhat arousing. Being used like this she felt powerless, which exonerated her from the feelings of lust that burned deep inside her. She was just a prison doll performing her duties right?

Petey dragged Bobbie to her feet again but this time he spun her around and pushed against the wall. He lifted the back of her dress out of the way and pawed at her panties, easing the gusset aside.

Bobbie took a deep breath and held it as Petey pressed his cock against her sphincter. Bobbie relaxed her anus and Petey’s cock slid into her all the way until his crotch was pressed against her buttocks. She felt full and thanked god that she had pre-lubricated herself. She let herself breathe and become comfortable with the organ that filled her void.

Petey stood still, enjoying the feel of Bobbie’s anus stretched tight around his bloated manhood. Before he was sent to prison Petey liked to fuck the whores in the Siceressos owned bordellos and he often sodomised the prostitutes because he felt it demeaned them and escalated his feelings of dominance.

Bobbie endured it. There was little pain and she knew that Petey would soon begin to thrust and she would push back just the way he liked.

Petey began to slowly withdraw his penis from Bobbie’s tight rectum and then he slid it back in just as slowly. Bobbie couldn’t help but let out a guttural moan as his glans pressed on her prostate. She felt the first dribble of precum leak from her penis and soak into her panties.

She wriggled her bottom and pressed back a little to meet his thrusts and Petey smiled. The bitch was loving it! He thrust a little harder and felt Bobbie shudder, her sphincter clamped around that base of cock and her anal muscles rippled. He fucked her a little, slowly and deeply, hearing Bobbie moan and feeling her body quiver.

His cock felt so snug in her tight anus and he felt his orgasm approaching. This time he would not stop it.

Petey hooked his arms around Bobbie’s waist and pulled her closer, he kicked her feet, splaying them so that she was bent over with her palms were pressed against the wall to keep balance.

He looked down at her long stocking-sheathed legs which were trembling. Her fine ass was swathed with those red satin hipster panties, the globes full and sensual and jiggling when he drove his cock into her, the crotch of her panties eased aside to allow his member access to her slick anus. He never for a second thought about what was in the front of those panties. In his imagination Bobbie was just another beautiful whore who needed to be fucked.

To her chagrin Bobbie couldn’t help the feelings of sexual bliss that she felt as Petey's cock massaged her prostate and sphincter. Her anus tightened around his cock and undulated, a trick that Bobbie had developed during hours of buggery. She was hypersensitive to her femininity: the scent of her perfume, the taste of her makeup, the silk, satin and nylon caressing her flesh.

She imagined what she looked like leaning against the wall, her pretty face framed by her long black locks contorted with lust, her dress hiked up, her legs spread wide sheathed in her glossy hose, her toes arched in her pumps, her panties eased aside and the bull of a man standing behind her, fucking her, holding onto her hips while he drove his cock into her tight ass while she pushed back against him appreciatively.

What a slattern she must look like.

Her cock had broken free and her testes had descended and she was hard inside her panties, the silken fabric rubbing on her penis as Petey drove his cock in and out of her anus.

Bobbie felt Petey’s fingers dig into her flesh and he pulled her back hard against him and groaned. She felt the flood of his semen filling her void and she whimpered with the lechery of it. She let herself go and creamed her panties, her orgasm trigged by Petey’s cock pressing on her prostate, the girth of it stretching her sphincter, the feel of it quivering inside her, releasing his seed deep inside her bottom.

She felt disgusted with herself but the gratification was overwhelming and beyond her control. She was a prison doll and she was doing what she meant to do. If she couldn’t control her lasciviousness it wasn’t her fault.

Petey fucked Bobbie a little more as the last of his cum erupted from his juddering organ, holding her tight and jackhammering his cock in and out of her, enjoying hearing her gasp, blather and wail. He didn’t care if her cries were pleasure or pain or a mixture of both, it was empowering.

He fell against her, spent and empty. The last vestiges of his orgasm began to recede. Petey pulled his cock out of her anus and slid her panties back into place and Bobbie clawed at the wall to keep her balance as she straightened up and pulled down the back of her dress. With as much decorum as she could muster she turned to face him.

“That was great doll, I’ll sleep like a baby tonight,” Petey chuckled, his limp cock hanging out of his flies.

He took the hem of her dress in his hand and wiped his cock, a final act of empowerment on his behalf. Bobbie just bemoaned that fact that his semen would mark the dress indelibly unless she was able to soak it before the stain set. It didn’t really matter. Tig would replace it in her next delivery of clothing.

Petey sauntered off to the bathroom and when Bobbie heard the shower begin to run she quickly opened a drawer in his bedside table. She snatched two of Petey’s Viagra and secreted them in her handbag and called out to Petey that she was leaving.

Marilyn was still busy with Tony and Mike and she heard the sounds of enthusiastic sex when she passed Mike’s bedroom. The girls never stayed overnight but they sometimes partied into the early hours of the morning if the men were in the mood.

Walking back to her block Bobbie could feel Petey’s semen leaking from her ass, soaking into her panties which were damp in the front from her own emissions. The alcohol was beginning to wear off and she became morose. In her room she shucked out of her clothes and threw them in a laundry basket inside the wardrobe where she kept all of Bobbie’s requisites. The stolen Viagra went into a drawer in the nightstand.

She sat before the mirror and used moisturiser and makeup wipes to remove the heavy makeup from her face and put her hair up in a man-bun. She took her towel and padded down to the ablutions, completely empty at this time of night. The shower washed away all vestiges of Bobbie but not the shame and guilt. That was an emotion that both Bobbie and Robert shared. One door in Bobbie’s mind slammed shut and another opened allowing Robert to assume control of their shared psyche.

Robert went back to his room, put on cotton pyjamas and ate two microwaved Lean Cuisines. He climbed into bed and stared at the crack in the ceiling, willing it ever closer to the light fitting in the centre of the ceiling. Another day of his living nightmare was over but there were still many to come.

The Siceresso Crime Family

A Google search for Sal Siceresso, Tony Siceresso, Petey Gruffalo, Joey Malzone or Mike Giacomo would produce remarkably little information. They owned or had significant interests in several legitimate businesses and had been convicted of street level felonies when they were younger but appeared to be men who had brushed up against the criminal element in their youths but had gone straight ever since. They were not known to the public as criminal masterminds and had never been mentioned in the press until their trial two years previously.

The five bosses of the Siceresso crime family had worked hard at remaining anonymous and staying below the radar of law enforcement agencies.

The Italian Mafia has long considered Atlanta and its suburbs to be ‘open territory’. Its local Italian-American population had never been old, large, or cohesive enough to field a local crime family on its own. Rather, families from other cities, such as New York's Five Families, had over the years embarked on one-off business ventures such as local restaurants, bars, and strip clubs as lucrative investments in their own right, or as front companies and mechanisms for money laundering.

Sal Siceresso and his younger brother Tony had seized the opportunity to create their own ‘family’ in Atlanta with loose ties to the New York families and to the so called Dixie Mafia. They didn’t import narcotics into the US directly but established business alliances with some of the Latina gangs based in Miami who did. They became a clearing house, funnelling drugs north for the New York families and across the south for the Dixie Mafia. They laundered money through a string of cash businesses and they had controlling interests in loansharking, gambling and prostitution operations. The family ran their more overt enterprises through intermediaries including their protection and intimidation rackets which were overseen by their henchman Tig Hansen.

The Siceressos eventually came to the attention of federal law enforcement but the FBI had bigger fish to fry and passed on any intelligence they gained to the Georgia Bureau of Investigation who began making a case against the crime family. Unfortunately the Solicitor General seized the opportunity to bring Joey Malzone, Sal Siceresso, Tony Siceresso, Petey Gruffalo and Mike Giacomo before the courts before the GBI could complete a thorough investigation that would have likely resulted in life sentences for the heads of the crime family. The Solicitor General was more interested in the publicity generated by a high profile case based on lesser charges. It was an election year and a victory in court was more important to him than waiting for the GBI to complete their investigation.

The bosses of the Siceresso crime family and their henchman Tig Hansen still received harsh sentences and were condemned to spend ten years in a high security State Prison despite pleading guilty. Their lawyers advised the men to cop a plea because once the men were incarcerated their lawyers would use the family’s contacts to ensure that the men served their time with little discomfort while their lawyers beavered away in the background making appeals against their sentences.

The result of the Solicitor General's brash and premature intervention meant that the Siceresso crime family’s businesses remained largely intact and operational. The heads of the family continued to operate their crime syndicate from prison through their trusted intermediaries on the outside.

Through those intermediaries the Siceressos acquired a controlling interest in Wakefield Services, a company that specialised in private correctional facilities management, including the provision of food services, cleaning, laundry, grounds keeping, maintenance, and custodial services. The corporation held valuable government contracts featuring minimum bed guarantees and a fixed price per-prisoner. They stocked overpriced commissaries and provided telephone services, and used prison labour in their supply chains.

The Board of Wakefield Services was only concerned with profit margins and it was easy for Siceresso’s people to infiltrate the prison management division and install a warden in Brentwood Correctional Facility who was a stooge for the crime family. They selected Bentwood because it was a remotely located minimum security institution with a wing that had been all but abandoned.

While their lawyers put pressure on people in the right places the Siceressos had the wing gutted and renovated. The contractors left the exterior looking like a rundown version the other accommodation blocks as Brentwood while the inside was converted into a five bedroom mansion.

Approving the transfer of the five felons from the high security State Prison to Brentwood Correctional Facility left a bad taste in quite a few mouths knowing that the criminals would spend the rest of their sentences living in the lap of luxury. Every effort was made to ensure the transfer was conducted with a minimum of fuss and in secrecy. Stringent caveats were put in place so that to all outward appearances it looked like the men were living under the same restrictions as the rest of prison populous: no illegal drugs or weapons were to be brought into the prison. Contraband smuggled into the prison by the Siceressos was to be for their personal use only.

Visitation and incarceration regulations were to be strictly adhered to. There would be no work-release, no visits from anyone except for the designated weekly visits by family, friends and their lawyers. Any breach of these rules by any of them would result in the five men being returned immediately to State Prison. Important people in high places were nervous and the Siceressos realised that they would be crazy to kill the goose that laid the golden egg. They were however able to wrangle the transfer of Tig Hansen to Brentwood and it suited their purpose that he live with the other inmates. He would be their conduit into the general population while they lived in glorious isolation.

Allie Katt

For Joey Malzone, Sal Siceresso, Tony Siceresso, Petey Gruffalo and Mike Giacomo their first year living in Seg was like a holiday after the short time they had spent in State Prison but as is often the case ‘good enough wasn’t good enough’. The men had the same visitation rights as the other inmates which included a once monthly conjugal visit with their wives. These were men who used to have their pick of any of the high-class hookers who worked out of their bordellos and whose power and money were an aphrodisiac for certain kinds of women. For such men once a month sex with their wives did not appease their appetites.

Putting pressure on their DoC contacts to let them bring women into their little fiefdom was greeted with a firm rebuke. The Siceresso crime family had no right being in Brentwood and anything as risky as smuggling in women or allowing the men outside the wire to satisfy their carnal urges was a sure-fire way to attract unwanted attention. The DoC had to draw the line somewhere and they were not going to let the Siceresso family turn Bentwood into an Escobar-esque La Catedral and the Siceressos were reminded that the stark alternative to the lap of luxury in which they lived was only a phone call away.

Tig Hansen listened to his bosses constant whine about the lack of sex and worked hard at coming up with a solution. He overheard a conversation one day in one of one of the common rooms that piqued his interest.

Allie Katt was a drag queen of some notoriety. She worked the drag pageants, cabarets, carnivals, and nightclubs just like the other ‘girls’ but she had a side-hustle selling cocaine. The first time she got caught dealing she was lucky enough to receive a suspended sentence but her second conviction resulted in a custodial sentence with time from her suspended sentence added for good measure.

Allie’s ‘government name’ was Allen Kettering and given his minimal criminal history and the relatively low significance of his crimes and the fact that Allen Kettering was a blatantly androgynous presenting gay man, he was sentenced to serve his time at Bentwood.

“So let me get this right. You dress up like a woman to perform and prance around the stage miming to other people’s songs and you get paid for it?” Tig Hansen asked Allen Kettering.

“How dare you!” Allen snapped back at Tig.

“Come with me you philistine!” Allen led Tig to the library, sat down at a computer and opened a web browser and pulled up images of the drag queen Allie Katt.

“Jesus! That’s you?” Tig said incredulously.

Allie Katt was stunning. Tall and curvy with long legs and a beautiful face. In some of the pictures she looked exactly like what she was: a drag queen. But in other pictures anyone would be hard pressed to think that she was anything other than a beautiful, desirable, sexy woman.

“Let me get to the point. Does Allie Katt get hit on much?” Tig asked blatantly.

“Oh honey the world is full of tranny-chasers. A lot of them are straight men too believe it or not. Of course I’ve also been known to kai-kai with other queens occasionally,” Allen batted his lashes at Tig who noticed that Allen was wearing a hint of eyeliner and mascara.

Tig didn’t ask what kai-kai meant… he could guess.

“And?” Tig raised his brows.

“Honey, if a drag queen gets caught sellin’ her ass while she’s pageanting or up in the club, her ass is grass. But what you do outside of that is your own business and some of them tranny chasers got lots of money,” Allen mimicked street talk and batted his eyelashes at Tig and smiled.

“Let me put something to you,” Tig looked around conspiratorially and began to whisper.

Tig thought long and hard about it and finally summoned up the courage to take his plan to his bosses. They sat around a laptop looking at cheesecake pictures of Allie Katt.

“That’s some fine broad… pretty face, nice long legs, nice tits, great ass but so what? Are you just trying to give me blue balls?” Sal Siceresso growled.

“What if I told you that she is here in Brentwood?” Tig grinned at his lords and masters.

“Get the fuck outta here!” Joey Malzone exclaimed.

“Wait a minute. This broad is a fanook?” Sal’s demeanour soured.

“Get the fuck outta here Tig. Anyone finds out that we’re fucking a fanook in here and our reputation is toast. That’s beside the fact that I ain’t gonna fuck some broad up the ass while her dick swings freely in the breeze,” Sal growled.

“Who’s gonna know? Allie won’t come in from outside the prison, she’s already here. You never see her except when she’s you know… Allie. She tells me the queens got this way of hiding their junk so you never see it. You guys have fucked boards up the ass before, I heard you talking about it and she tells me she can suck a tennis ball through a garden hose,” Tig shrugged his shoulders is if to say que sera, sera.

“Get the fuck outta here Tig,” Sal Siceresso growled again but Joey and Petey kept shuffling through the onscreen pictures of Allie Katt.

They cornered Tig later away from the others.

“She’s gonna look exactly like that? She’s gonna look like a woman, walk like woman, smell like a woman, talk like a woman and we aint gonna see her braciole?” Petey asked anxiously.

“Not unless you want to,” Tig smirked.

Joey grabbed Tig by his shirt collar and pushed him against the wall.

“You don’t joke about this shit! Anyone finds out Tig and it’s you who is getting his braciole chopped off,” Joey snarled.

“Absolute discretion boss. Gimme a couple of days to bring in the necessaries and I’ll bring Allie to you and Petey and you can try before you buy so to speak,” Tig eased Joey’s fingers from his collar.

“What about this Allie?” Petey asked.

“I pump up her commissary and drop a few bucks into her outside savings account as payment. I bring in everything she needs to do what she needs to do. I tell you guys, this broad is a doll, you’ve seen her pictures,” Tig said enthusiastically.

“See, we’re already calling her ‘she’ and Allie. No reason to think she’s anything other any other than a hump,” Petey agreed.

And so it was done. Allie knew her sizes and she went on an online shopping spree ordering dresses, shoes, lingerie, hosiery, cosmetics and the other essentials a ‘tranny’ needed to pass. She forwarded her shopping list to Tig who agreed to purchase half the clothes and shoes she asked for. Until his bosses told him that they were satisfied with Allie’s ‘performance’ he wasn’t obliged to invest too much money into the venture.

“These men want the full fantasy right? They want me to be as convincing as possible. Well that means you gotta front up some good quality merchandise, you get what you pay for, you know what I mean?” Allie tried to convince Tig to buy everything she had ordered but Tig told her to make do.

Three days later the goods were delivered to Allie’s room.

“Come back in two hours sugar and I’ll show you what you paid for,” Allie winked at Tig and eased him out the door.

As a drag queen Allie wore hip and buttock pads and breastforms to present an exaggerated female physique whilst performing. But she was not presenting as a drag queen she was presenting as a transvestite and the padding, prosthetics and exaggerated stage makeup would not be required.

Allie was tall, slim and hippy and could get away without a corset. She had ordered a couple of good quality wigs but for her debut she would use her natural hair which was shoulder-length brunette. Allie visited the inmate who operated the barbershop and paid him to cut her hair into a shag bob with bangs. Sitting in front of her mirror she teased it until it framed her face perfectly and then she set it. She went to work on her makeup, tucked and taped and rolled on a pair of fifteen-denier sheer to the waist pantyhose to hold everything in place and pulled her white satin panties tight over the pantyhose. She adjusted the brassiere and slipped two ‘chicken fillet’ prosthetics in the cups to give her some shape.

Tig returned at the appointed hour and knocked gently on the door and entered. What he saw took his breath away.

Allie was stunningly beautiful. Her perfectly made-up face was framed by her bangs and bob, her long elegant neck atop perfect unblemished shoulders and petite décolletage which was exposed by a low-cut emerald-green satin sheath dress. The dress was floor-length and spilt up one side to the hip. Allie stood with one leg thrust forward to show off her long shapely legs, her feet shod in green high-heeled pumps. She had accessorised with silver jewellery set with faux rubies. She was clouded in a miasma of exotic perfume.

Any man would be hard pressed to recognise Allen Kettering inside the visage which was Allie Katt.

“Fuck me!” Tig was agog.

“No honey. That’s my line,” Allie replied with a sultry feminine rasp that sent shivers down Tig’s spine.

“Wait here,” Tig left Allie’s room and walked down the corridor.

He advised every inmate he saw to keep their mouths shut if they knew what was good for them and went back to Allie’s room.

“Let’s go,” we hooked a finger at her and Allie picked up her clutch and followed him out into the hallway.

To some extent walking down the corridor reminded Allie of walking from her dressing room to the stage. To all intents and purposes she was about to give the performance of her life. She felt comfortable, feminine and desirable dressed as she was. Allie would normally be padded, corseted and be wearing stoned fishnet tights over two pairs of sheer pantyhose to keep her hip and buttock pads in place and be wearing heavy stage makeup and a big lace-front bouffant. She would be sweaty and a little uncomfortable dressed in drag but dressed as she was tonight she felt every inch a woman.

During the walk to Seg Tig gave Allie some final instructions.

“These guys won’t take any shit. They expect you to behave like the type of woman they might pick up in a nightclub; think high class hooker. You do whatever they say and under no circumstances do they want to see your dick,” Tig rattled for what must have been the twentieth time.

“I get it. Show them a good time and keep my dick tucked. It’s not like I haven’t done this before,” Allie harrumphed.

“And check the attitude. You take the PrEP?” Tig glowered.

Tig was beginning to wonder if this was such a good idea. Allie Katt was a stunner but she had a mouth that could get them both in trouble.

“Yeah, I took the PrEP. I was on it right up until I was incarcerated. You checked with medical so you know I’m HIV negative and free from STDs,” Allie snapped back.

Despite the widespread use of intravenous drugs and homosexual sex few prisons provided PrEP or condoms to the inmates. It was being considered by the DoC but the wheels were moving slowly. Wakefield Services was considering providing the service in the prisons the company managed, passing on the costs to the State of course at inflated prices.

Tig had added PrEP to the list of medications he smuggled into the prison for his bosses. He was taking no chances with Allie because Allen Kettering was gay and might have hooked up with other inmates. He also smuggled in Viagra for his bosses to take during their conjugal visits.

Joey and Petey were waiting just inside the door and when Tig punched in the code they anxiously shepherded Tig and Allie into Joey’s room and closed the door.

“The other guys are playing poker,” Petey Gruffalo said just above a whisper.

Joey said nothing. He was too taken with the stunning woman reeking of perfume standing only inches away from him. He reached out and stroked Allie’s cheek and she smiled at him seductively. Her skin was smooth and soft and Joey was already enraptured with her,

“Never mind who is doing what. Come back in a couple of hours Tig and collect Allie. Go and shoot the shit with the others. Lose some money and keep them away from my room,” Joey pushed Tig towards the door.

Tig left the room and heard the door lock behind him. He hoped he’d done the right thing. He sauntered off to lose a few hands of poker to his bosses and keep them occupied while Joey and Petey tried out Allie Katt to see if she was to their taste. He was worried that Petey and Joey were going to be aggrieved or disgusted and take out their anger on him. Also, Allie was a looker but she had a sharp mouth.

“Are you two boys going to keep staring at me or are you going to offer a girl a drink before we have a good time?” Allie said salaciously.

Tig needn’t worry. Allie’s mouth and attitude ingratiated her with two gangsters who found her brazen assertiveness charming. It helped that she looked stunning and her sultry voice was seductive. Neither of the men thought of her as a ‘fanook’. She was sexy and desirable and cheeky and all they could think about was their Viagra-assisted hardons.

Petey poured expensive scotch whiskey into crystal tumblers while Allie sidled up to Joey and pressed herself against him.

“You like what you see?” she smiled seductively at him and Joey pulled her into his arms and kissed her.

Allie kissed him back. Allen Kettering liked big powerful men and so did Allie Katt, even more so. She could feel Joey’s cock pressing into her despite his substantial gut.

“I see you’re happy to see me big boy,” Allie squeezed Joey’s cock through his pants.

“What about you there mister? You want some of this too?” Allie pirouetted out of Joey’s grasp and fell into Petey's arms.

She snuggled up to him and kissed him. Petey was instantly hard. This girl was so sexy and womanly. She was brash and lewd and totally fuckable. They both forgot that Allie was actually a resident in the same prison. All of their fantasies were being fulfilled as she flitted from one to the other, kissing, fondling and caressing Joey and Petey until the men just wanted to pounce on her.

“How’s this gonna work? You gonna do Petey first, then me?” Joey asked kicking off his shoes and tugging at his pants.

“You boys aren’t shy are you? Why don’t you do me both at the same time? I’ve got two holes,” Allie winked at them and hopped on the bed.

“It’s my room; I should go first,” Joey whined.

“Fuck that! I got seniority,” Petey growled.

“Come on boys. Don’t argue. There’s plenty of me to go around,” Allie called from the bed.

She had shucked out of her dress and was dressed only in her tight white panties, shimmering pantyhose and heels. She’d ditched the chicken fillets and her erect little nipples pushed against the sheer fabric of her transparent brassiere.

She looked coquettish with her pretty face framed by her shoulder-length brunette bangs and bob. She lay on her back kicking her legs like a showgirl, smiling at the men seductively. They both admired how the panties clung to her buttocks, the valley of her natal cleft visible through the slinky panties and super-sheer pantyhose. Most of all they admired the perfect Vee between her legs. They both knew that there was no vagina there but that was last thing on their mind.

As the two men approached the bed Allie got on her hands and knees.

“It’s simple arithmetic boys. One in front and one in back,” Alley eased aside the gusset of her panties showing off her perfect gleaming globes.

She slipped a blood-red fingernail into her ass crack and snagged a little hole in her pantyhose so that her puckered bud was visible.

Both men swallowed and leapt on the bed.

Allie had pre-lubricated and when Petey’s hard cock slid into her ass there was no resistance.

“Oh god yes honey you are tight,” Petey moaned.

Allie couldn’t answer because Joey’s cock was in her mouth and she was suckling on it like it was a lollypop. She worked her lips up and down the shaft and used her tongue on the sensitive glans, swallowing the copious amounts of precum dribbling from Joey’s cock.

He was on his knees in front of her watching her pretty mouth work his phallus while Petey fucked her from behind. Allie got into rhythm, pushing back against Petey’s thrusts while her mouth slid up and down on Joey’s quivering organ.

Petey came first, ramming his cock all the way inside Allie’s tight rectum, grinding his pubis into her pantyhosed buttocks. He held her high heels in each hand while he unloaded his issue deep inside her. Allie moaned appreciatively around Joey’s cock and slathered at the thick veiny member, feeling it judder. Then her mouth was filled with his sweet, musky spunk.

It had taken Allie less than ten minutes to make both men cum and she was feeling very self-satisfied.

The men clung to her, unwilling to let her go. She was amazing: sexy, vivacious, cheeky and seductive.

Allie looked up at Joey and smiled, his deflating lipstick-smeared penis inches from her face. He had a satisfied smile on his face.

“So you boys wanna change ends and go again?” she smirked.

Petey and Joey took a half hour break, swapped ends and came back at her again and Allie was more than ready to oblige. This time it took a little longer for the men to cum but Allie made sure that they were both satisfied. She quite enjoyed it herself but made sure that her tuck stayed put despite the pain of having her semi-erect penis taped long her perineum.

When the men were finished Allie took her dress into the bathroom, cleaned up, fixed her hair and makeup and put her dress back on. When she emerged she looked as stunning as when she had first arrived.

“How did I do boys? Did I pass the test?” Allie beamed at them.

“You sure did doll,” the men said in unison.

Joey went to find Tig while Petey kissed and canoodled with Allie for a little while, then Tig lead Allie back to D Block.

Joey and Petey got together with Sal, Tony and Mike and told them about their encounter with Allie. They told their comrades how Allie presented as a feminine, desirable, sexy woman and how she gave great head and how tight her ass was and how they hadn't seen anything that even looked like a dick. They explained how Allie was funny and engaging and good company, as well being a great hump.

Tony and Mike were keen to try her out but Sal was still sceptical.

Tig was told to bring Allie to Seg again the next night and she was everything that Tig, Joey and Petey said she was. She was engaging and cheeky and sexy and Tony and Mike became as besotted with her as Joey and Petey were and after drinks and some banter they took her away and sampled her wares and were not disappointed.

Allie became a regular fixture at Seg. Every night she would go there and entertain the men and eventually even Sal relented and took her to his room and was also not disappointed.

The five gangsters had no idea that Allie Katt was in fact Allen Kettering. Of course they knew deep down that Allie was another inmate who lived only yards away from them in another wing but they didn’t want to acknowledge that. They only ever thought of Allie as an enchanting female companion who was amazing in bed.

It soon became apparent to Allie and to Tig that Allie couldn’t keep up the demanding workload placed on her. She was in Seg almost every night and on all of those nights she was required to perform sexual congress with at least two of the men, usually more. There just wasn’t enough Allie to go around. She was a victim of her own success.

“We need another girl,” Allie confided to Tig after a few weeks.

“I can’t keep this up; my ass is going to prolapse and I’m going to get lockjaw. All joking aide, I need a partner” she sighed.

“How we gonna do that?” Tig asked.

“Leave it to me. Can I offer her the same deal?” Allie replied.

“Sure but you gotta make sure she can keep her mouth shut. No one in genpop can know what happens in Seg,” Tig warned.

“I’m on it honey. Be prepared to take another order for clothes, makeup and all that shit. I’m going to make you another girl,” Allie quipped confidently.

Maurice Shrew took little convincing. He was a gay man without a life partner who played the field. Whilst the idea of crossdressing to service five old mobsters was not that appealing, the regular stipend into his commissary and bank account was.

As it turned out Maurice was a natural and with some coaching from Allie was soon presenting as Marilyn, the femme name she chose for herself, which Allie thought showed little imagination but it didn’t matter because Marilyn was quite the dish. After a week of coaching Marilyn made her debut in Seg and was an instant hit.

Between them, sometimes singly but mostly working together, Allie and Marilyn spent most evenings in Seg entertaining the five mobsters, enjoying the opulence, the attention, the sex, and of course the money. Marilyn took to her job like a duck to water and soon came to enjoy dressing and presenting as Marilyn.

The Siceressos used the affectionate euphemism doll with Allie and Marilyn: ‘Come here doll and sit in my lap’, ‘yes doll, suck it just like that’, ‘can’t wait to get my hands on those dolls; I’m going to shove my braciole right up Allie’s ass’.

And so Allie and Marilyn became their prison dolls. It was a convenient circumlocution, not expressly gendering the ‘dolls’ as women but repudiating their true gender. The Siceresso bosses didn’t know the male identities of Allie and Marilyn nor did they ever want to. That would ruin the illusion. That was left to Tig who filled the role of their whoremaster.

Tig Hansen had done well and was rewarded by his bosses accordingly. After a while, other than ordering and paying for his ‘girls’ feminine requisites, he didn’t have much to do with them at all. The girls were given the passcode to the entrance door to Seg and came and went as they were needed.

The Warden was in the pocket of the Siceresso crime family and she made sure that what happened in Brentwood, stayed in Brentwood. The prison officers, all employees of Wakefield Services and selected personally by her, knew to keep their mouths shut and they didn’t even acknowledge that Seg existed and ensured that the existence of Allie and Marilyn remained a secret to the outside world. Tig used coercion, blackmail and bribery to keep the populous of D Wing, where Allie and Marilyn were quartered, in line.

Being a privately run prison, the DoC had little oversight into the management and day-to-day running of the Brentwood Correctional Facility. Wakefield Services met and exceeded their KPIs. There were no breakouts and few disciplinary problems and few, if any, complaints from the inmates. The Siceressos ensured that Wakefield Services kept the inmates content with good accommodation, excellent amenities and fair work practices. The inmates at Brentwood knew they had it good and made it their business to keep schtum about anything they suspected about the existence of Seg and the goings on associated with it.

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.

It looked like a perfect Vee between Allie’s legs. The same Vee that you would expect to see on a woman.

“You saw me tuck. You are going to have to do the same. This might be a little uncomfortable at first but it should not be painful,” Allie reached for Bobbie’s groin and she stepped away.

“Bobbie. You have to learn to trust me. Put everything out of your mind and learn from me,” Allie said sternly and Bobbie nodded reluctantly.

Allie used two fingers to tuck each testicle up into Bobbie’s corresponding inguinal canals. It felt weird but not painful. Allie had Bobbie do it herself a few times until she was comfortable. Then she pulled Bobbie’s penis and scrotum backwards between her legs.

“This will help keep your testicles tucked up in your inguinal canals. At this stage we can either use tucking tape or your underwear to keep everything in place. I’ll show you both methods,” Allie said quite clinically.

“Now, let’s look at your wardrobe,” Allie said gleefully.

Allie had approximated Bobbie’s sizes based on prison records which weren't much help but they did have Robert Valentine’s waist and chest measurements and importantly his shoe size which Allie was able to convert into a female size chart. She had guessed the rest by carefully but unobtrusively observing Robert on the wing.

“But first I need to get you into this,” Allie said holding up what appeared to be a band of flesh-toned spandex.

She had Bobbie step into it and pulled it up so that the top of the cincher fitted just below Bobbie’s ribcage and the top of her the hips. Bobbie now had an hourglass figure.

“You can ditch this in a few weeks when you lose the weight,” Allie commented flippantly.

“Now comes the fun part,” Allie grinned.

None of this had seemed fun to Bobbie. It was confusing and daunting but she went along with it because the alternative was not worth considering.

Allie laid out a selection of pantyhose, stockings, panties, brassieres, slips and lingerie.

“I want you to tuck and then sit down and put on these pantyhose,” Allie held out a pair of fifteen denier sheer-to-the-waist pantyhose and Bobbie took them from her.

Robert had always had a thing for women wearing nylons and he often implored Mandy to wear them for him and to occasionally wear them for him during sex. Mandy thought it strange but if it kept her man happy she was happy to comply to appease him.

Robert would never admit this to anyone, but like a lot of men, he tried on his wife’s pantyhose and panties once in while so putting the pantyhose on was not alien to Bobbie.

Bobbie sat on the bed and gathered one leg of the pantyhose to the toe and then she pointed her toe and slipped her foot inside. Gently pulling the smooth fabric up her leg, easing it carefully and slowly, making sure the fabric didn't pull or rip, she kept the hose leg centred and pulled it up until she reached her thigh. She did the same with other leg and then she stood up and pulled up the pantyhose so that the elastic at the top sat around her waist.

Bobbie had worn pantyhose a few times before but the feeling of these luxurious hose on her freshly shaved legs was amazing. She risked losing her tuck as her penis began to engorge but she remained stoic and pulled the gusset of the hose snug to keep her tuck tight. Putting on the full-cut black satin panties helped keep the tuck in place too but she shivered with delight as the sleek lacy garment slid along her gossamer pantyhose. Bobbie felt a single droplet of precum leak from the eye of her cock.

“I think you did that little too well and liked it a little too much. Have you been hiding something from me Bobbie?” Allie sniggered and gave Bobbie a knowing wink.

Bobbie blushed but said nothing.

Allie helped her put on a brassiere that matched her panties and showed her how to adjust it and placed two ‘chicken-fillet’ breast prosthesis in the cups to give them some shape.

“I’ll let you play with the slips, petticoats and lingerie later. For now I want you dressed and walking so the lessons can continue,” Allie said handing Bobbie a white satin blouse.

“Why would I want to play with the slips and lingerie and when are we breaking for dinner?” Bobbie was becoming agitated again.

“You won’t be eating dinner again for a while. You may have a light breakfast in the morning and a single lean quinine before you go to bed until you lose that belly. Also, you will soon discover that your eating habits will be dictated by things more important than hunger,” Allie snapped.

“Now put that blouse on and keep it away from your makeup and button it carefully because it buttons on the other side to a man’s shirt

The next hour or so was taken up with Bobbie trying on shoes, skirts, blouses and dresses, discarding those that didn’t fit and keeping those that did. Allie paired skirts with blouses and shoes with ensembles. When they had finished Bobbie and Allie had a small wardrobe collection laid out on the bed.

“This will do for now. You will need to add to your wardrobe anyway when you lose that gut and your size changes,” she tapped Bobbie in the stomach playfully.

“Tomorrow will be fingernails, followed by poise, walking in heels, mannerisms and speech. Get undressed, take off your makeup and wig and take the clothes, wigs shoes and this makeup case with you. Go back to your room and practice your makeup skills and tucking. If you’re up to it, try walking in those heels for a while. See you tomorrow,” Allie dismissed Bobbie.

When Robert went back to his room Allie made her way to Seg and brought Tig up to speed. It looked like Bobbie was the perfect candidate to take Allie’s place. Allie had sex with a couple of the Siceresso men as usual and returned back to her dorm and had a good night’s sleep.

Robert lay on his back unable to sleep, staring at the crack in the ceiling snaking its way towards the light fitting wondering why his life had been turned upside down. All he ever wanted was to just do his time and then go home and pick up the pieces of his life.

To be continued