Chapter 1

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.