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Home > Michele Nylons > Prison Dolls - Chapter 1

Prison Dolls - Chapter 1

Author: 

  • Michele Nylons

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Reluctant
  • Blackmail
  • Crime / Punishment

TG Elements: 

  • Bad Girls / Promiscuity
  • Corsets
  • Panties / Girdles
  • Prostitution

Permission: 

  • Posted by author(s)
Prison Dolls  Edited.jpg

Chapter One – Pretty Boys Make Pretty Girls

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

Prison Dolls - Chapter 2

Author: 

  • Michele Nylons

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Reluctant
  • Crime / Punishment
  • Proxy / Substitute / Stand-In

TG Elements: 

  • Bad Girls / Promiscuity
  • Corsets
  • Fancy Dress / Prom / Evening Gown
  • Panties / Girdles

Permission: 

  • Posted by author(s)
Prison Dolls  Edited.jpg

Chapter Two – Sometimes It’s Good To Be a Girl

Bobbie’s Debut and Allie’s Farewell

Robert knew that worst was yet to come. He was being trained to become Bobbie for only one reason and very thought of what that was reason terrified him. What was both a comfort and a concern was the ability he was already beginning to master switching his psyche between Robert and Bobbie. Thinking of Robert as: he, him and himself and thinking of Bobbie as: she, her and herself. Bobbie was a yet unformed personality. Bobbie knew about makeup, hair, shoes and clothes and she didn’t think about Mandy, Charlotte or even being in prison. She was just concerned about developing her femininity.

Robert was concerned about his wife and daughter and his feelings of helplessness at being unable to protect them other than to surrender himself to his fate and which was to let Bobbie take over his body and psyche and let Allie teach Bobbie how to become a prison doll.

He slept fitfully.

The next day Robert was told that he had been reassigned to the laundry and would only be working half days. He would miss working out in the fresh air but having the afternoons to himself was a bonus but he wasn’t stupid and knew why the change in employment had been effected.

Allie took Robert to the hairdresser.

“With that face and those green eyes I’d like to see the hair dyed jet black, perfectly straight and centre parted with bangs. What do you think?” Allie asked the hairdresser who was paid a generous stipend by the Tig to keep Allie and Marilyn's hair looking perfect.

The barber, or as he preferred to be called, the hairstylist, agreed and went to work. The hairstylist appreciated being able to actually colour, cut and style a nice head of hair rather than just perform a buzz cut, a short-back-and sides or shave a head bald, which was what most of the inmates asked for.

Back in Robert’s room a while later after fixing her makeup and dressing, Bobbie looked at her face in the mirror and hardly recognised herself. She looked stunning. Allie showed Bobbie how to attach false fingernails and how to care for them which was easy. What was not so easy was walking in high heels and adopting feminine mannerisms but Bobbie was up to the challenge.

“Don’t try to alter your voice too much because it will be too difficult to maintain,” Allie explained as she helped Bobbie cultivate a raspy but feminine sounding voice by modifying her pitch, vowel pronunciation, breathing control and resonance.

Bobbie’s voice resembled that of Kathleen Turner or Lauren Bacall.

Bobbie spent the next few days practicing how to present as a provocative, sensual and desirable woman whilst Robert continued to develop the skill to surrender his body and mind to Bobbie, who to him was a completely different person. It was a coping strategy that worked. In the dark recesses of his mind Robert wondered what would happen if he allowed Bobbie to take over completely.

As end of the week approached the daunting and dreaded subject of sex was finally raised by Allie.

“Today I’m going to teach you how to perform fellatio. As a man existing in a woman’s body you have one distinct advantage, you know exactly what men like,” Allie smiled conspiratorially.

“You’ve been blown before, right?” Allie asked facetiously.

Of course Robert had been ‘blown’ before. His first fumbling sexual encounter in high school when he had just turned eighteen was being blown by his girlfriend in the back of a car. Some girls were better at it than others; of that there was no doubt.

Robert’s wife Mandy did not like performing fellatio. She withheld the practice for special occasions like his birthday, their anniversary, Valentine’s Day or after he purchased her a particularly nice gift. The truth was, she wasn't particularly good at it but Robert never looked a gift horse in the mouth.

“I think its best that we have sex together now. I want Bobbie’s first sexual encounter to be enjoyable and to be honest, you are sexy as fuck,” Allie glowered at Bobbie as if she was something to be devoured.

“Just relax and go with it. You will enjoy it I promise,” Allie smiled and sidled up to Bobbie.

Allie embraced Bobbie. It was not the first time that Allie had been close to her of course, teaching Bobbie how to present as a woman involved plenty of touching in intimate places but this was different. Allie’s embrace was gentle and comforting, her lips were millimetres away from Bobbie’s and Bobbie gazed into Allie’s big blue eyes and saw tranquillity and trust, not raw lust.

Their skirts brushed just as their lips did the same. The flutter of the hem of their skirts against Bobbie's hosed thighs was delightful. When their lips touched there was a spark. Bobbie would be lying if she didn’t admit that she found Allie very attractive and alluring. She didn’t think what she was doing wrong because Allie was a woman right? Well that wasn’t quite right because Bobbie was cheating on Mandy but that thought flittered away. Robert tried not to think of Mandy when he was presenting as Bobbie. Another defence mechanism.

Bobbie surrendered and returned the kiss, their lips pressed together only lightly, enjoying the delicate sensuality of it, tasting Allie’s lipstick, inhaling her perfume, feeling her feminine curves pressed against Bobbie’s satin-shrouded body. The rustle of satin and lace, the hiss of a skirt skimming over nylons, the sensation of a thickening cock pressing against glossy panties. Bobbie felt Allie smile. Bobbie knew that Allie considered it a victory that Bobbie hadn't rejected her advances but Bobbie didn’t care. She was living in the moment and the moment was delightfully different to anything Bobbie had ever experienced.

The two women embraced each other tightly and their kisses became more fervid, no longer delicate, they kissed open-mouthed and used their tongues. Instinctively Bobbie’s hands explored Allie’s body: caressing her cheek, stroking her swan-like neck, lingering in the small of her back until they came to rest on Allie’s pert buttocks.

Allie slipped her hands inside Bobbie’s blouse then inside her brassiere and stroked Bobbie’s nipples. They hardened to Allie’s touch and circlets of pleasure radiated from the tender teats. Bobbie had never had her breasts manipulated like this before because it was not part of Robert and Mandy’s foreplay. It felt delightfully provocative and Bobbie imitated Allie and found Allie’s sweet nubbins and caressed them.

They didn’t break their kiss. Their tongues explored each other’s mouths as they stroked each other’s tiny breasts. Then Allie’s hand snaked down Bobbie’s body and slipped under her skirt. She found Bobbie rock hard inside her satin panties. She squeezed Bobbie’s cock gently and Bobbie sighed.

The feeling of Allie’s hand sliding under her skirt, across her stocking-clad thighs, gently caressing her cock through the silky panties was indescribably erotic.

“Oh, that feels so good,” Bobbie gasped.

“Sometimes it’s good to be girl, right Bobbie?” Allie teased and tweaked Bobbie’s penis.

Bobbie didn’t answer. She mimicked Allie and slid her hands down Allie’s torso, stopping briefly at her waist to pull her closer and kiss her and then her fingers found the hem of Allie’s skirt. She slipped her hand under and stroked Allie’s thighs and felt Allie shudder. Bobbie slid her fingernails up and down the gossamer-clad flesh, her wrist brushing on the coiled member inside Allie’s panties.

“You’re getting the hang of this,” Allie sniggered.

“Shut up,” Bobbie snuffled into Allie’s mouth, kissing her deeply.

The feel of Allie’s body against her own feminine form was delightfully different, decadent and alluring. As well as Allie’s soft curves, silky clothing, lush perfume and her soft lips, her hair brushing Bobbie’s face, Bobbie was intensely aware of her own femininity. The taste and smell of her makeup and perfume, the caress of silk, satin and nylon against her flesh. She experienced her very womanliness.

“Oh god!” Bobbie whispered as Allie began to stroke Bobbie’s hard cock through her panties.

Bobbie found Allie’s cock coiled in her panties and touched it tentatively and it sprang free; hard, warm and palpitating inside the delicate garment. Bobbie touched it again and wrapped her fingers around it and began to stroke it. She could feel the hardness and powerfulness of it through the satin panty material.

It didn’t feel wrong, it felt empowering and decadent. Bobbie felt supplicant and submissive whilst at the same time she felt assertive and controlling. Allie wanted Bobbie and Bobbie wanted to serve Allie, the dichotomy was not lost on her.

“Ok, here we go,” Allie smiled into Bobbie’s face and then she dropped to her knees.

Allie licked Bobbie’s cock through the front panel of her panties and heard Bobbie groan and felt her knees begin to buckle. She freed the appendage from Bobbie’s panties and slipped it into her mouth. Bobbie rested her fingers on Allie’s head and moaned as Allie began to fellate her.

Allie slid her lips up and down the shaft of Bobbie’s rod, tracing the veins with her tongue, fluttering the tip of her tongue against Bobbie’s fraenulum. Bobbie had never been sucked by such an accomplished cocksucker and she relished the feel of Allie’s mouth on her throbbing penis. Allie suckled Bobbie’s scrotum, taking her scrotal sack into her mouth and lashing her tongue on Bobbie’s testes while she wrapped her fingers around Bobbie’s cock and stroked it.

Bobbie’s knees buckled further and Allie felt Bobbie begin to release precum in an almost continuous stream. Allie put her mouth back on Bobbie’s penis, sensing her need. She began to fellate Bobbie earnestly, sliding her lips up and down Bobbie’s shaft and lashing her tongue on the sensitive glans.

A deep guttural moan escaped Bobbie’s lips as she felt Allie’s warm, wet mouth suck her achingly hard appendage. Bobbie felt her scrotum contract and her penis judder as her orgasm approached.

Allie sucked harder and faster and suddenly her mouth was full of hot, musky sperm. Bobbie entwined her fingers in Allie’s hair and fucked Allie’s face as an enormous orgasm overwhelmed her. Bobbie’s testes roiled, her cock quivered, and her whole body shook as Bobbie deposited her load inside Allie’s mouth.

Allie continued to suck, lap and lick Bobbie’s cock until it was drained. She let Bobbie rest her hands on her shoulders until she sensed that Bobbie was able to remain standing without assistance. Allie jumped to feet and pulled Bobbie close and kissed her deeply.

Bobbie held Allie in a warm embrace and returned the kiss feeling genuine intimacy and affinity for Allie for the first time.

They kissed and canoodled. Allie slipped Bobbie’s deflating penis back inside her panties and guided Bobbie’s hand to her own swollen member and Bobbie gasped it and stroked it and finally freed it from its silken prison.

“My turn,” Bobbie giggled and dropped to her knees.

Sucking Allie’s cock was not as disgustingly awful as Bobbie imagined it might be, in fact Bobbie had a genuine affinity for it. She mimicked everything that Allie had done to her and did some things that Allie hadn't but that Bobbie had always wanted a woman to do to her.

Bobbie was tentative at first. The tip of Allie’s cock peeked out the waistband of her panties which Bobbie found quite erotic. Bobbie licked the tip of Allie’s penis and then she put her lips around the glans. Expecting to be a little repulsed Bobbie found that the opposite was true. Allie’s penis tasted clean and the texture was interesting. Bobbie used her lips and the tip of her tongue on the spongy mass and smiled when she heard Allie moan. It was quite empowering knowing that she had caused Allie to yelp with delight.

Bobbie pushed down Allie’s panties a little to expose the full length of her tumescent protuberance. Bobbie opened her mouth a little wider and took the girth of Allie’s cock into her mouth and clamped her lips around the base and lightly used her tongue on the turgid pole. Allie gently placed her hands on Bobbie’s shoulders.

“Good girl,” Allie sighed, encouraging Bobbie.

Bobbie did not feel like a good girl. She felt like a naughty girl but she was enchanted by Allie’s response. Bobbie began to move her mouth up and down on Allie’s penis, using her lips to caress the shaft and her tongue to lap, tickle and suckle the spongy glans. Bobbie just did what she wished Mandy would do to her own cock.

“Oh my god, that is wonderful,” Allie moaned, rocking slowly back and forth on her heels, feeding her cock into Bobbie’s soft, sultry mouth.

Bobbie sensed that Allie wanted her to quicken the pace but she didn’t. She kept the same slow steady rhythm, sucking, slavering and licking Allie’s throbbing cock. She relished the sweet offering of Allie’s precum. She savoured it before swallowing it. Bobbie cupped Allie’s scrotum still encased in her slinky panties and massaged the bulging sac, feeling Allie’s testes contract signalling that she was about to ejaculate.

Then Bobbie felt the first freshet of spicy spunk on her tongue. Bobbie clamped down her lips and suckled Allie’s pulsing phallus, moving her mouth a little more quickly and lashing her tongue over the plush mass of Allie’s glans. She felt Allie’s seed spurting from the eye of her cock and Bobbie relished the taste of the creamy discharge.

When Allie finally released her load into Bobbie’s willing mouth, Bobbie swallowed every drop. It didn’t taste vile at all, in fact Allie’s semen tasted delicious. Bobbie licked Allie’s cock clean and tucked it away and Allie helped Bobbie to her feet.

Bobbie was grinning like a Cheshire cat.

“There, that wasn’t so bad was it?” Allie lightly brushed Bobbie’s bangs out of her eyes and kissed her softly.

Even though they were both wearing long-lasting lipstick most of it had come off on their respective phalluses.

“No it wasn’t Allie. But when I do that in Seg, it won’t be with a gorgeous, feminine transvestite. It will be with some brute criminal,” Bobbie felt the onrush of post-coital regret.

“You will either begin to like it or come to tolerate it. There is no escaping your fate Bobbie. And by the way… we are all criminals here in Brentwood. I don’t want to be cruel but if you weren't a criminal you wouldn’t be in this predicament,” Allie said plainly. Reality bit and Allie left Bobbie with that thought.

Robert mulled it over as he undressed and removed his makeup then headed to the shower. He noticed that the diet and exercise were already having an effect and his belly was no longer as big as it had been. He knew that sex with the men in Seg would not be restricted to masturbation and fellatio but he was just too tired and confused to think about it.

He tried to think of other things but he kept thinking about being in Allie’s embrace, kissing her, feeling her body against Bobbie’s, their stocking-clad legs rubbing together, their hands caressing hard willing flesh through slinky panties, Allie’s mouth on Bobbie’s rampant organ. Bobbie’s mouth on Allie’s sleek phallus, feeling it harden, feeling it judder when Allie expressed her seed into Bobbie’s willing mouth and hearing Allie moan with wanton lust as she orgasmed.

Robert gave up and got out of bed and retrieved a stocking from the laundry basket. He climbed back into bed and draped the stocking over his hard cock and slowly masturbated thinking about having sex with Allie.

Later he lay on his back and stared up at the crack in the ceiling until he was finally able to asleep.

The next day Robert Valentine sat in Allen Kettering’s room and stared at the blue ovoid tablet that Allen had placed before him. It was strange being alone in Allen’s room with both of them dressed as males in prison clothing. For the last week the first thing Robert and Allen did after breakfast was to transform into their femme alter egos and spend the day working on Bobbie’s feminisation. Tig had somehow got them excused from the compulsory lunchtime headcount.

“You start taking one a day from now on and you front up for an STI check every six seeks. Tig will arrange the check-up for you at the infirmary,” Allen explained.

Robert swallowed.

“What is it again?” Robert pointed at the blue pill.

“It’s a pre-exposure prophylaxis that pretty much precludes the risk of contracting HIV. Tig insists that the dolls take it and to be honest, it’s as much for your own protection as it is for the Siceressos,” Allen explained.

“Look, both Maurice and I are gay and to be honest the only people I’m having sex with are the guys in Seg. I don’t know about Maurice, he might be sexually active with other inmates. You have conjugal visits, the Siceressos have conjugal visits. Everyone is fucking everyone and although the risk is low, whenever you have unprotected sex you’re fucking every sex partner they have recently had sex with. So you take the PrEP and you get checked regularly for STIs. It protects you and everyone else,” Allen continued.

“Are you insinuating that my wife might have an STI?” Robert said angrily.

“I’m saying nothing of the sort. I’m saying Tig says we take PrEP so we take PrEP. It’s that or condoms and no one is wearing condoms,” Allen was getting a little tired of having to explain everything twice to Robert.

Allen understood why. They were about to discuss anal sex and he could see that Robert was terrified. As much as Bobbie had undoubtedly liked the oral sex Allie and Bobbie had engaged in, anal sex was a totally different conundrum.

Robert swallowed the pill, chasing it with water. He was terrified because he was dreading what was coming next.

Also laid out on the table was a black vinyl bag inside of which was a shower enema kit. Allen had explained how to use it and emphasised the need to keep flushing until the water ran clean. This was followed by taking a two Imodium tablets as extra insurance so to speak.

“Ok, let’s go,” Allen snatched up his own enema kit and his dopp kit and Robert followed suit.

Robert and Allen had the ablutions to themselves but one of the shower stalls and a wash basin showed evidence of recent use.

“Marilyn has already been in,” Allen said matter-of-factly.

Robert had come to terms with the gender switching terminology. Around the correctional facility they were Robert Valentine, Maurice Shrew and Allen Kettering. As soon as they began their transformations or when talking about their femme identities they were Bobbie, Marilyn and Allie. Collectively they were ‘the dolls’. At first it had seemed bizarre but now it was just habitual.

Robert and Allen went into separate toilet cubicles and did the necessary. Robert’s new diet was not only helping him lose weight, it changed his regularity and now he understood the effectiveness of it.

They stood side by side not saying much while they shaved, brushed their teeth and gargled and then they entered adjoining shower stalls. Robert followed the instructions he had been given and attached the enema apparatus to the shower head.

“Yuck!” Allen smiled when he heard Robert’s cry of dismay as he expelled his first douche.

“You get used to it. Keep going until the water runs clean,” Allen called out.

Back in Allen’s room they both popped two Imodium and began to transform. The metaphysical transformation occurred as soon as Robert sat down in front of the vanity mirror and Bobbie emerged and took over Robert’s mind, body and soul.

Allie had insisted that Bobbie get ready for her debut in Allie’s room so that she could ensure that Bobbie presented perfectly and also to reassure her. She couldn’t imagine how terrified Bobbie must be feeling but she was sympathetic. It was also in Allie’s best interest to ensure that Bobbie performed well because Allie’s freedom depended on it. During the week Tig had been dropping in now and then during Bobbie’s training and he was impressed by what he saw.

“Yeah, she looks the goods. She’s even more beautiful than Marilyn but it all comes down to how she performs,” Allie reminded Tig.

“Well you just better make sure she doesn’t fuck it up,” was Tig’s final say in the matter.

“Some of those boys prefer that I wear stockings and some of them prefer that I wear pantyhose. I’ll let you figure out who likes what and when,” Allie said as she leaned over Bobbie’s shoulder and fidgeted with her hair.

Allie’s sweet breath on Bobbie’s face and the smell of her perfume was comforting but referring to the five thugs who lived in Seg as ‘boys’ seemed incongruous to Bobbie. Allie had described the men in Seg to Bobbie and advised her of their differing temperaments but that did little to quell Bobbie’s fear and to be honest, Allie thought it best that Bobbie find out for herself.

“Tonight you’re going to wear pantyhose to make sure that your tuck stays in place. What’s the number one rule again?” Allie asked.

“Don’t show your dick and never break character,” Bobbie repeated for what she seemed like the thousandth time.

“You’ll do fine,” Allie kissed Bobbie’s cheek.

Bobbie finished with the hair straightener, unplugged it, and brushed her glossy black mane until she was happy with the results. Her makeup was perfect and all she had to do now was dress. She tucked and taped and took the fifteen denier, shimmery, sheer-to-the-waist pantyhose from Allie, sat down and slipped them on, delighting in the feel of the gossamer hose on her freshly shaved legs despite her trepidation.

The black satin lace-edged panties slid up her legs and coddled her pert butt. She checked her Vee in the mirror. Perfect! You would never know she had ‘boy parts’ hidden in her panties. The matching bra followed, chicken-fillet prosthesis filling the small cups to give the bra a little shape.

Allie helped her step into the navy-blue sheath gown with the plunging neckline, three-quarter lace sleeves and side split that went all the way up to her hip. Then she stepped into the matching pumps while Allie fussed with the drape of the garment so that it fitted Bobbie perfectly. Bobbie’s diminishing potbelly was flattened by the cincher and with her narrow shoulders, wide hips, hourglass figure and long legs Bobbie looked like a model.

Bobbie’s alabaster skin was flawless and her hair and makeup prefect. Allie was a little jealous although she looked nearly as stunning in the matching red gown she was wearing.

“We’ll meet Marilyn there,” Allie said as she helped Bobbie put on her costume jewellery.

The hairdresser who had cut, dyed and styled Bobbie’s hair had performed double duty and pierced Bobbie’s earlobes. They had healed to the extent that she could wear the silver drop earrings that matched her necklace and bracelets. The silver rings she was wearing were set with faux sapphires to compliment her gown.

The two gorgeous transvestites stood side by side and looked in the mirror at the perfection they were presenting.

“I won't say don’t be nervous because you will be. Just let Bobbie take over and remember what’s at stake,” Allie said reassuringly and took Bobbie’s hand in hers.

They stopped to pick up their clutch purses and Allie handed Bobbie a pair of pantyhose straight from the package and a pair of panties that matched the ones she was wearing.

“Put these in your clutch, you will probably need them,” she stuffed the garments into Bobbie’s hand and stepped into the corridor and beckoned Bobbie to follow.

It was strange walking down the corridor of D Wing presenting femme. Robert had only ever presented as Bobbie in either Allie’s or her own dorm room but Bobbie’s training was such that she walked with a feminine gait on her high heels along the carpeted corridor without thinking. Bobbie could hear the muffled voices of other inmates gathered in their dorms and common rooms. All the doors were closed although some of them opened a crack and then closed. She knew that she was being watched but no one approached them or made any comments.

Allie had explained to Bobbie that Tig was the Siceresso’s enforcer on D Wing and kept the other occupants in line using bribery and intimidation. The Warden and the COs, all employed by Wakefield Services, were in the pockets of the Siceressos and enforced the code of silence. The additional privileges the prisoners in D Wing received and the ever present threat of retribution kept them in line.

Bobbie recalled Robert’s interview with the Warden during the induction process at Brentwood and Robert’s insistence that he wanted to keep to himself and just do his time when questioned about his integrity. He had never questioned why at a certain time each evening the inmates were confined briefly behind closed doors but now he knew why. He had dismissed the rumours of a bunch of inmates living in luxury in E Wing as fanciful but now Bobbie knew the truth.

Bobbie and Allie exited D Wing and followed a path lit by LED edge lighting to E Wing, their high heels clacking on the concrete. From outside, the building looked abandoned but the lights in the windows betrayed the presence of occupancy.

“Don’t forget what I told you. Be demure. Endure everything. I know you are terrified but remember your job is to keep these men satisfied. It’s probably going to hurt a little but they are not sadists. These men want your company as much as they want sex. I know you don’t believe me but I think eventually you are going to enjoy what they do to you,” Allie whispered.

“How the fuck am I going to enjoy being sodomised!” Bobbie hissed.

“You never believed that you would enjoy sucking cock Bobbie but you can’t deny that you enjoyed our little tryst can you?” Allie replied.

Bobbie didn’t reply but she was blushing. Her anger and her inquisitiveness overrode her fear and she realised that’s exactly what Allie wanted. She wanted to ensure that Bobbie’s fear didn’t paralyse her. Bobbie knew that Allie’s freedom was dependent on Bobbie’s performance tonight.

They came to the side entrance to E Wing. Incongruent to the faded peeling paint, fitted to the door jamb was a very modern looking electronic keypad.

“If you’re accepted and once they trust you they will give you the code,” Allie said as she tapped a code into the keypad.

Allie said this as if it was some kind privilege but to Bobbie it only reinforced to her that this would become a regular occurrence.

The door opened and Bobbie stepped inside following Allie and then she stopped almost paralysed, dumbstruck by what she saw. Allie’s description of Seg could not match the visage that greeted Bobbie as she stepped through the grungy looking exterior into a world of opulence.

The doors to the rooms on either side of the corridor were closed but Bobbie heard music, laughter and the tinkling of glasses coming from the end of the corridor. It felt like a party was in full swing.

“Come on dummy,” Allie yanked on Bobbie’s wrist and pulled her along behind her.

Bobbie stood stock still and open-mouthed at the entrance to a huge lounge where modern expensive furniture was arranged around low tables. The lounges and chairs faced a wall dominated by a huge flatscreen TV which was currently blank but music was coming from a very good sound system, turned down low to permit conversation. One side of the room was dominated by an oak dining table set for six, behind which was an open kitchen that any chef would be envious of.

Five middle-aged men stood in a circle dressed casually but expensively and in the middle of the circle Marilyn Shrew, dressed in a black evening gown, was the centre of attention.

Bobbie had not seen Maurice Shrew presenting femme before but she looked gorgeous. Bobbie shouldn’t have been surprised. She had witnessed her own transformation so seeing bald-headed, slim, lanky, rather effeminate Maurice presenting as Marilyn: a tall vixen in a black satin gown with perfect makeup wearing a ‘Dolly Parton’ shoulder-length, platinum-blonde wavy-curled wig and black pumps was not as shocking as it would have been a little over a week ago.

Marilyn appraised Bobbie and at once disliked her. She had better legs, poise and grace and she was stunningly attractive. Those Bambi eyes, full of wonder and bewilderment, would attract the men like a magnet. Not that Marilyn was concerned. There were five men in Seg who needed regular servicing so Marilyn’s position was secure. For some reason she just didn’t like Bobbie.

“Hey our new doll is here,” a big headed, bull necked teddy bear of a man wearing an open-necked lounge suit exclaimed.

Everyone in the circle turned to face Bobbie and Allie and Bobbie felt the men’s eyes crawl over her.

Tig had taken pictures of Bobbie and shown them to the inmates in Seg but the pictures could not hold a candle to how Bobbie looked in real life.

“Come join us,” the most elderly of the men beckoned.

Allie gave Bobbie a light push in the back to get her moving.

Bobbie stepped into the room still amazed by the bizarre splendour of Seg, almost forgetting why she was here. The feminisation training she had endured over that last week had the desired effect and Bobbie kept her composure. She was only in the here and now and later she would admit to herself that she a little flattered to be the centre of attention.

The circle of men opened and Bobbie and Allie joined Marilyn. A drink appeared from nowhere and Bobbie took it and gulped it down, the alcohol mellowing her a little. The men were talking all at once and they closed in the girls. Bobbie found herself standing between the older man and a slightly younger man who introduced themselves as the Siceresso brothers.

The Siceresso brothers made small talk, the two men complimenting Bobbie and welcoming her to Seg. The conversation steered clear of anything to do with Brentwood, criminal activity or Bobbie’s gender. They treated her like a lady and Bobbie gratefully accepted the drinks they gave her. She figured the alcohol might make things easier but after four drinks the men cut her off. They didn’t want to have sex with a sloppy drunk.

Allie and Marilyn had drawn the attention the remaining three men who were chatting to them, occasionally squeezing their buttocks, groping them affectionately and sometimes kissing them. Allie kept her eyes on Bobbie throughout the fondling trying desperately to reassure Bobbie that everything was ok through eye contact.

Before the dolls arrived it was agreed that Sal Siceresso as the elder statesman would take Bobbie first. Sal clinked his glass with a pen he had taken from his pocket and everyone in the room went quiet.

“I’d like to welcome our new doll Bobbie to our little club. I know you gentlemen are keen to entertain our guests, especially our newest acquisition and of course to say farewell to Allie. I’m sure the partying will continue long into the evening but as you know I’m an early bird and not much for staying up late, so ladies and gentlemen, enjoy yourselves. Bobbie and I are going to get acquainted,” Sal made his little speech as if he was addressing a family gathering.

Sal tugged on Bobbie’s arm and the last thing Bobbie saw before she was led away was the look on Allie’s face which read: ‘don’t fuck this up!’

Sal led Bobbie to his bedroom which resembled a luxury hotel suite but she had little time to look around because Sal dimmed the lights and led Bobbie to the middle of the room. Bobbie was much taller than Sal especially in her heels but he clutched at her and pulled her face down to his. She dropped her clutch and let Sal kiss her.

The kiss was not as revolting as Bobbie thought it might be. Sal held her close and stroked her arms and her back; he didn’t grope her which was what she expected. He wasn’t a particularly good kisser, he kept his lips closed and stuck out his tongue now and then but Bobbie endured it and reciprocated. It wasn’t as mind-numbing as she’d imagined and she put that down to the drinks she had drunk and the fact that she was fully immersed in the persona of Bobbie. She shut out the outside world and kissed Sal and put her arms around him.

Suddenly Sal was all hands. He pawed at her dress, slipping his hands inside the low-cut bodice. He ripped the little prosthetics from her brassiere cups and began to squeeze her teensy tits and pinched her nipples.

“Ouch!” Bobbie squealed.

“Don’t wear those plastic tetas in here. I like your tiny tits,” Sal growled.

Sal had changed from a soft-spoken, hunched over little man, who Bobbie thought was very toad-like, to a demanding lecher. He slapped his lips back on Bobbie’s mouth and thrust his hands inside her dress and groped her thighs.

“Nice legs Bobbie… now let me see… oh yeah… Allie has taught you well,” Sal held Bobbie at arm’s length and opened her dress like you would open drapes.

Sal gawped at the perfect Vee between Bobbi’s legs.

“Nice panties,” Sal rubbed his fingers between Bobbie’s legs.

“Here let me…” Sal unzipped his flies and released his stubby hard cock.

What it lacked in length it made up for in girth. He pulled Bobbie close and rained slavering kisses on her lips while he thrust his cock between her legs. He liked the feel of Bobbie’s slinky panties and silky pantyhose on his flesh.

Allie had not gone into specifics as to what the men in Seg liked to do sexually, just that each man had his preferences and that Bobbie should become accustomed to them, be receptive and proactive.

Bobbie returned Sal’s sloppy kisses and stayed perfectly still while Sal humped her thighs. Bobbie couldn’t believe that she was thinking this way but she hoped that Sal would cum on her leg so that she wouldn’t have to suffer the indignity of having to fellate him… or worse.

“Ok, doll. Let’s see what else Allie had taught you,” Sal reached up and put his hands on Bobbie’s shoulders and pressed down.

Bobbie knew what he wanted and she got to her knees. In the dim light Bobbie could see that Sal’s cock was stubby and thick and leaking viscous pre-ejaculate. Part of her was revolted by it but she knew what she had to do in order for her family to survive so she reached out and stroked it.

Bobbie didn’t consider Allie a man so it was surreal touching a man’s cock for the first time. The girth of it, the smooth shaft and spongy glans coated in precum was not as repulsive as she thought it would be. For the first time since she had arrived in Seg she felt an inkling of power. She was desired, wanted, lusted after. She was a plaything for the five men in Seg. But they all coveted her and that provided a tiny scintilla of self-satisfaction.

Sal slapped her hand away and put his hands on her head and pushed her face into his groin.

He gasped as Bobbie took him her mouth and began to slide her lips along the shaft while she tickled his frenulum with the tip of her tongue. She hoped that he wouldn't last long as she worked her lips up and down his shaft. Bobbie looked up into his eyes just like Allie had taught her so that Sal could see her beautiful face as her lipsticked lips slid up and down his cock.

Sal’s wife flatly refused to fellate him, saying that only whores and goomahs lowered themselves to such a vile act. But Sal had been blown by Allie and Marilyn too many times to count and he’d been fellated by high-class hookers. But there was something about this tall, beautiful, long-legged goddess in the blue sheath gown that enthralled him. Maybe it was her beauty, maybe it was the fear he saw in her eyes, maybe it was because she was new, maybe it was because Sal knew that he was her first. Whatever it was, the experience was exhilarating.

Her mouth was warm and moist, her lips locked around his shaft and she moved her head up and down on his quivering cock, her lips were doing something to his glans that was indescribably exotic. Sal looked down into her pretty painted face, her eyes looking up adoringly under her long dark lashes, her red lipsticked lips clamped around his cock and he could feel his climax building.

Bobbie sensed it and she sucked Sal’s cock faster and lashed his glans with her tongue. Sal put his hands on her head and plunged his cock in and out of Bobbie’s mouth. He filled her mouth with his creamy issue and smiled as he saw Bobbie grimace but she swallowed his offering and kept sucking.

Bobbie nearly gagged when Sal ejaculated but she resisted the urge to spit out Sal’s penis and renewed her efforts so that she drained every last drop of his spend. Allie would have been have proud of her. She had passed her first test.

Sal pushed her away and stuffed his cock back into his pants.

“Go and re-join the party. You’ve got a big night ahead of you Bobbie,” Sal walked over to his compact bar and poured himself a drink dismissing her.

Bobbie’s mind was in turmoil. She was repulsed and sickened by what she had just done but she was also a little proud of herself. She had come through her first sexual encounter with a man unscathed. And not just any man. This man was a crime boss, a powerful oligarch. She should be disgusted with herself and she was, but she was also feeling a little smug. She stood outside Sal’s door and adjusted her dress and fixed her makeup and then she made her way along the corridor guided by the sounds of raucous laughter.

When Bobbie came back into the party room Allie was sitting in one of the men’s lap and she gave Bobbie a questioning look. Bobbie nodded curtly indicating that everything had gone well.

Bobbie didn’t get to say anything because a tall, slim, dark-haired man gripped her upper arm and led her away. He took her to one of the other bedrooms and closed and locked the door.

“Tequila time I think,” Mike Giacomo went over to the drinks cabinet and poured drinks.

“How was the boss?” he asked, turning to face her.

“When I left him he was happy. In fact he was pouring himself a drink just like you’re doing now,” Bobbie replied.

Bobbie was feeling a little more confident in herself having seen to Sal’s needs. She suppressed the conflict that was going on inside her and took the drink that Mike handed her.

“I’m Mike Giacomo. Have you heard of me?” he asked as he cast his eyes over Bobbie, appreciating what he saw.

“No I haven’t,” Bobbie replied truthfully.

“Good. I don’t want to be famous, I just want be rich,” Mike smiled at her like an alligator might smile at its prey before it struck.

Bobbie drank down the fiery liquid in one swallow.

“So you're Allie’s replacement. You're just as pretty, maybe more so. I just hope you are as good as her in bed,” Mike swallowed his drink.

“I don’t know. I’ve never done this before. Until Tig gave me to Allie I had no idea that this was even possible. I was just another inmate serving his time,” the look of rage on Mike Giacomo’s face alerted Bobbie to the fact that she broken the number one rule.

She had broken character.

Mike’s hand shot out and grabbed Allie by the throat, shocking her.

“Get this right and don’t ever forget it. Tig and Allie should have drilled this into your thick skull already,” Mike tightened his grip on Bobbie’s throat.

“We don’t want to hear anything about your life. We aren’t interested. When you walk through that door you’re Bobbie. Your job is to look beautiful and be sexy and alluring. You are here to entertain us. I know Tig will recompense you for your services and I’m sure he has a stick as well as a carrot to keep you in line, but as I said, that is not our concern. Do you understand?” Mike released his grip on Bobbie’s throat and she took in lungful's of air.

She nodded vigorously, still trying to catch her breath.

“Say it!” Mike growled.

“I understand,” Bobbie gasped.

“Good. Now get on the bed,” he growled, snatching the glass from her hand.

Bobbie walked over to the bed on shaky legs, holding her clutch tight against her belly.

“Kneel on the bed with your ass up high,” Mike demanded.

Bobbie did as she was told. She was still shaking and very frightened as she heard Mike shed his clothing behind her.

Bobbie had never felt so vulnerable, waiting like that, kneeling on the big bed with her head down and her ass lifted high in the air. She heard Mike pad across the room and open the drawer on a bedside table. He placed something on the bed near her leg then he climbed on the bed. His weight shifted as he positioned himself in front of her.

“You’re a good girl when you keep your mouth shut. You only need to open it to kiss me and take my cock,” Mike chuckled and she felt his crooked finger lift her chin so she was looking at him.

Bobbie saw Mike’s lean tanned body kneeling before her. His long slender cock jutted out from his crotch. The pose was quite erotic in a way and Bobbie swallowed hard, expecting Mike to push her face into his groin but he lifted her head higher so that she was kneeling facing him.

The kiss was hard, powerful and demanding and Bobbie was caught unaware. She automatically put her arms around Mike to keep her balance and he pulled her close and slipped his tongue into her mouth.

What was wrong with her?

Bobbie mewed and returned the kiss. There was something uniquely erotic about being held by this brusque, powerful man while he was naked and she was dressed in her evening gown, nylons and heels. Kissing Allie had been delightful in a very ‘kissed a girl’ kind of way. Kissing Sal had been like kissing an old man who had forgotten how or had never learned how to kiss properly. But kissing Mike, being held in his strong manly embrace, feeling his muscled body, feeling his soft yielding lips, feeling his hard rod pressing against her belly… this was something different and surprisingly compelling.

She felt her cock begin to tug at the cosmetic tape holding it in place as it awoke. It was so wrong and she should not be reacting this way. She should be a trembling kitten, terrified of what was happening to her but instead she was kissing this ruffian, pressing herself against him, whimpering like a schoolgirl kissing her boyfriend at the prom.

“Jesus, you are beautiful, there is no doubt about that,” Mike complimented her when he finally broke the long languid kiss.

Bobbie was breathless and she accepted the compliment graciously. She remembered what Allie had taught her and Mike had reiterated: she was here to please the men in Seg. She tentatively reached out and took Mike’s sleek manhood in her hand. She felt that surge of power return and she leaned forward and kissed Mike passionately. Bobbie could not deny that contrary to what she had expected she was feeling aroused.

Mike held her close while they kissed and she stroked his throbbing cock, extruding dewy droplets of pre-ejaculate which she worked into his flesh. She could feel her cock engorging again, pressing against the tape holding it in place. Her panties and pantyhose would keep it in place if it broke free so she wasn’t too worried. What was a little disturbing was that she was becoming aroused but that was something to worry about later.

Right now she was enjoying the feel of Mike’s hard body pressing against her silken-shrouded flesh, the feel of his lips on hers, his arms holding her close, his sighs of contentment. She had never felt more femme than she did now.

Then Mike’s Jekyll and Hyde duplicitous nature emerged and he changed from the considerate inamorato to the demanding lecher once again. He pushed Bobbie away from him and pressed her down on the bed.

“Head down, ass up lady. I haven’t got all night,” he growled.

He knee-walked around behind Bobbie and lifted her dress.

“Great ass,” she felt Mike squeeze her buttocks.

He opened her legs and settled in behind her and Bobbie felt Mike’s cock press into the crevice between her buttocks. She clenched and gritted her teeth but Mike wasn’t quite ready to fuck her yet. He held her hips and rubbed his cock on her satin-pantied globes. She could feel the girth of his phallus fretting on her bottom, her panties swishing against her pantyhose as he thrust his cock into her natal cleft.

It wasn’t an unpleasant feeling but she had lost the sense of powerfulness and fearlessness that was undercurrent when they were kissing and canoodling. She felt vulnerable, and even more so when Mike eased aside the gusset of her panties.

He pressed his cock against her sphincter, only the gossamer fabric of her pantyhose between her anus and Mike’s turgid prong. She clenched, which was exactly what she knew she shouldn’t do and she gasped when Mike hooked a fingernail in the fabric of her pantyhose and made a little hole.

This was it. This was what Bobbie had been dreading. She could fantasise all she liked about being a desirable sexy woman while she was kissing the men, she could even defend the feelings of verve and wantonness she felt when she stroked their cocks and even fellating Sal had not been the horrendous abominable act she thought it would be. But the truth was that she about to be sodomised and she was terrified.

She felt Mike’s fingers scrambling on the coverlet for the object he had placed next to her calf and in a few seconds she realised what it was.

She felt the cool salve of the emollient as Mike squeezed a gobbet of lubricant into her puckered bud. She instinctively bucked a little and Mike’s hand came down hard on her buttock. The slap resonated through the silence broken only my Mike’s heavy breathing and Bobbie’s stilted wheezing as she knelt on the bed in terror.

“Keep still doll,” Mike hissed.

Bobbie hissed as what felt like a steely hard poker slid into her anus. At first she thought Mike had begun to sodomise her but then realised it was only his finger. Her sphincter clamped around the digit as Mike eased it in and out of her anus.

“The tighter you are, the more I’m going to enjoy it but I think you better relax Bobbie or you're going to feel some real pain,” Mike grunted as he slipped another finger inside her.

Was it that Mike had called her Bobbie? Not doll, not slut or some other egregious expression. Was it that she was finally accepting her fate, the inevitability which had been unspoken? Bobbie would later realise that it was acceptance. This was her life now and there was nothing she could do about it but surrender.

Bobbie concentrated on relaxing her sphincter. She buried her head in the coverlet, gripping the fabric in her outstretched hands and kept perfectly still, her ass raised high in the air, her legs apart and prepared herself for the inevitable.

“That’s better,” Mike snickered and removed his fingers from her bottom.

She felt him edge closer to her, his thighs pressing against hers. Then she felt the protuberance of his sex nestle in her crinkled spherule.

Bobbie’s scream could be heard in the lounge room and Allie winced. In the bedroom adjoining Mike’s, Joey Malzone was balls-deep in Marilyn Shrew’s ass and she was riding him cowboy. They both laughed.

“Not so aloof and hoity-toity now is she,” Marilyn sniped and then returned to bouncing up and down on Joey’s swollen ‘braciole’ as he liked to refer to his penis.

Bobbie’s face was screwed up in pain and she entwined her fingers in the coverlet and tried her best to loosen her sphincter as Mike’s long, sleek cock distended her anus. The single scream she had been unable to suppress had earned her a vicious slap on the ass and she mewled softly and tried her hardest not to expel Mike’s cock from her asshole.

It’s strange how a person’s mind works when they are under duress. Despite the pain, all Bobbie could think about was that she grateful that she had douched because the indignity of not doing so would just consummate the degradation she was feeling. Allie would be proud of her though. Bobbie remained in control; Robert was nowhere near her consciousness. Robert would not be able to endure this.

“That’s it doll, just relax and take it,” Mike cooed.

Mike had nearly cum when his cock had slid into Bobbie’s virgin anus. Her sphincter was so tight that it gripped his flesh as he drove it into her. The spongy mass of her rectum which fit snugly around his turgid cock when he impaled her. He held her hips, lifting one hand to spank her when she screamed, returning it to her hip to hold her still.

“Just stay like that honey, don’t move,” Mike whispered.

To Bobbie this was a godsend. Mike’s bloated penis was deep inside her but he wasn’t moving it. Gradually she was able to relax her postural muscles and slacken her sphincter a little so that the searing pain subsided into a dull throb. It was bearable. She knew the worst was over. She could feel Mike’s cock throbbing inside her and sensed that he was close to extremis. He wasn’t fucking her but it wasn’t because Mike didn’t want to cause Bobbie any more discomfort by battering her tight hole, it because he didn’t want to climax too quickly.

“Ok doll, let’s do this. Let’s fuck,” Mike lifted Bobbie to her hands and knees and placed his hands on her shoulders.

He slowly began to fuck her, easing his cock almost all the way out of her ass and then sliding it all the way back inside her, relishing the tightness of her velvety tunnel.

Bobbie tolerated it. It was no longer excruciatingly painful but it was uncomfortable. She felt Mike’s cock sliding in and out of her anus, the lubricant fulfilling its purpose, easing the way for his cock. She felt his thighs pressing against hers and she felt her buttocks quiver whenever he pushed it all the way inside her. Her sphincter stretched to accommodate the invading fleshy stanchion.

Then she felt something surprising.

Bobbie felt little ringlets of pleasure begin to radiate from her prostate.

Bobbie knew that gay men enjoyed being sodomised, otherwise why else would they do it? But Allie had not told her about the deep resonance that having a cock hit that special place invoked. The pain still outweighed the pleasure but it made it more tolerable.

“That’s it babe, push back,” Mike moved his hands to her hips and held her tight and plunged his cock inside her a little faster.

Bobbie was unaware that she had started to push back against Mike’s thrusts. The thrusts were long and slow and the more accepting she became being filled by his corporeal manhood the more her pleasure centres supressed her pain receptors.

Once again she became aware of her femininity: the feel of her satin gown caressing her body, the delightful sensation of her nylons encasing her limbs, her feet shod in the high heels, the taste of her makeup and the scent of her perfume. But it was more than that. She was kneeling supplicant on the bed, a strong vibrant man holding her hips, his flesh pressed against hers, his manhood inside her, her back arched and her buttocks raised, pressing back against his groin as he drove his phallus deep into her tight clunge.

Mike became aware that Bobbie was no longer resistant and he fucked Bobbie a little faster. He admired her plump buttocks clad in the shimmering hose, her long legs, splayed just wide enough to accept him, the curve of her back, her prim waist, her glossy black mane. His wished he had rolled her over so he could look into her dazzling emerald green eyes and gaze on her pretty face and kiss those full sensuous lips while he fucked her but it was too late for that.

He felt his scrotum begin to roil as it slapped against her silken-gusseted taint and his cock began to quiver as his orgasm began to germinate.

Bobbie felt the change in Mike. He was holding her tighter, digging his fingers into her hips as he began to fuck her harder and faster. She thought this would invoke more pain but in fact the result was the opposite. Sparklets of pleasure radiated from her sphincter, her anus felt wonderfully full, luxuriant warmth emanated from the spongy mass of her rectum and the most intense carnal gratification was building in her prostate.

She could feel that her cock had broken free of the tape as Mike buggered her and it caused her pantyhose to slither back and forth along its length. It was quite painful having her cock trapped between her legs but she knew that’s where it had to stay and Bobbie endured the combined pleasure and pain gladly.

Mike pulled her back tight against him, his pelvis pressing against her buttocks, his thighs compacted against hers and Bobbie felt his cock judder and she realised that Mike was ejaculating. She could hear his ragged breathing, feel his cock fully distend and begin to pulse as he unloaded his seed deep inside her.

Bobbie pushed back obligingly and wriggled her ass. She was whore, a concubine, a slut and in the moment she relished the role. Her cock was tingling and her prostate jangling. She was nowhere near extremis but she was edging with decadent desire.

“Yes honey, yes baby, yes, yes, yes!” Mike bellowed as he slammed his cock all the way inside Bobbie and collapsed on top of her.

Her legs gave out and she lay flat on the bed with Mike’s weight on top of her, grinding his pelvis into her soft nylon-sheathed buttocks, his cock quivering as the last of issue burst forth, deep inside Bobbie’s tight anus. He kissed her neck and held her tight, delighting in the feel of her tight rectum enveloping his turgid organ.

Bobbie sighed.

It was over. She had lost her virginity. Was it as awful as she expected it to be? At first yes, then it became tolerable… after that… she didn’t want to think about the illicit enjoyment she had felt. Post coital regret washed over her.

But not Mike.

He lay on top her, nuzzling her neck, whispering that she had ‘done good’ into her ear. He let his cock slowly deflate inside her. When Mike’s breathing returned to normal and his cock was no longer turgid he climbed off Bobbie.

Hyde replaced Jekyll again.

“Get your fat ass off my bed before you stain the bedding,” Mike pulled on Bobbie’s ankles, dragging her toward the bottom of the bed.

Bobbie shimmied down the bed and got gingerly to her feet, keeping her dress raised. She could feel Mike’s goop dribbling from her ass. Mike nodded towards the ensuite and Bobbie felt like a well-used harlot as she walked gingerly to the bathroom, holding up her gown, the back of her panties becoming wetter as rivulets of Mike’s semen dribbled from her bruised sphincter.

Bobbie carefully took off her gown and then her pantyhose and panties which were wet and musky with fresh semen. She threw the tucking tape which had come undone during the sex in the trash along with the pantyhose with the hole in the crotch. She unrolled several sheets of toilet paper and wiped her ass then she took the clean pantyhose and panties from her clutch and put them on. She didn’t have any tucking tape but she knew the pantyhose and tight panties would keep her tucked.

She stepped back into her gown and struggled with the zipper but managed to close it. She straightened it. Without the ‘chicken fillet’ prosthetics her bust was negligible but she still looked attractive, especially after she freshened her makeup. She stepped into her heels and considered what to do with her cum-soaked panties and just shrugged as she jammed them in her purse. She fussed with her hair and exited the ensuite to find Mike Giacomo dressed and eager to leave.

“Let’s get back to party doll, the evening is young,” Doctor Jekyll had returned.

He even put Bobbie’s hand in the crook of his arm as he led her back to party. Allie and Marilyn were sitting side by side on a couch. There was something about their freshly applied makeup, recently brushed hair and their slightly wrinkled dresses that indicated that both of them had recently had sex. The men were at the bar pouring drinks, laughing and talking raucously. Bobbie knew that Mike was regaling them with the story of how he had just deflowered her.

“How was it?” Allie asked matter-of-factly as she drew on a cigarette.

“It was a bit rapey. Can I have one of those?” Bobbie pointed at the open packet of menthol slims on the table.

Bobbie surprised herself when she issued the curt, snappy response but Allie smiled. Her protégé was hardening up. Good.

They partied into the night but the men were sated sexually and they drank, danced and chatted as if they were in any big city nightclub. Allie, Marilyn and Bobbie left Seg around 1am and were tucked up in bed half an hour later.

Robert stared at the crack in the ceiling trying to make sense of it all. He was appalled by Bobbie’s brazen behaviour but also glad she was able to cope with what easily would be considered a nightmare by some. If he wasn’t sure before, he was now certain that becoming Bobbie, letting her exist as an entity separate to him was the only way he would survive.

The next day was Sunday, a day off for most of the inmates and they were allowed to sleep in. Robert was awakened by a rap at his door and then it opened and Allie stepped into his room. That’s right; it was Allie Katt not Allen Kettering who entered his room.

She was wearing skinny jeans and a white loose longsleeved top with big red lips logo embroidered across the front in sequins. She was in full makeup and heels, her brunette shag bob perfectly coiffed.

“I thought I would come and say goodbye,” she sat down on the edge of the bed uninvited.

“What are you doing?” Robert sat up in bed.

“I’m being processed and I’m starting my new life. I can’t hide my gender identity any longer,” Allie explained.

“You’re transitioning?” Robert was taken aback.

“Yes honey. I don’t expect you to understand but that’s ok. Bobbie did good last night. I know it’s daunting and confusing but you just do what you to do to survive honey and you deal with it any way that works. Time will pass quicker than you think,” Allie patted Robert on his upper arm.

“That’s what you did. You did what you had to in order to survive. You sold me to the Siceressos to gain your freedom,” Robert said bitterly.

“I did just that. You will too when the time comes,” Allie sighed.

Robert was about to reply when Allie cut him off.

“If I may quote Shakespeare: The lady doth protest too much, methinks,” Allie leaned down and kissed Robert’s cheek and left the room without another word.

Robert Valentine’s life had changed forever and Bobbie Valentine’s life had just begun.

Robert and Mandy – The Conjugal Visit

Robert settled into his new life, most evenings handing his consciousness over to Bobbie who served the men in Seg. It became routine and Robert endured it for the sake of his family but Bobbie became accustomed to it and Robert was a little concerned that Bobbie might even like it on certain evenings, especially when she was assigned to take care of Tony Siceresso. That was troubling. The burgeoning relationship that Bobby was developing with Tony but there was nothing Robert could do about it.

Robert had visitation rights every weekend and conjugal visits were allowed once a month for prisoners who were married or in a recognised relationship. Mandy was due to arrive Saturday afternoon and would be allowed to stay overnight with Robert in one of the ‘conjugal cottages’ set aside for such visits. Tig Hansen had approved the visit because it was important to those on the outside, including Robert’s family, that it appeared that Robert was serving his time exactly the same as the other inmates. It might be the Warden who signed off on the paperwork for the conjugal visit but Tig had the final say.

Men who were locked away from women found other ways to satisfy their sexual urges. Some inmates became ‘gay for the stay’, engaging in homosexual activity while they were incarcerated and then reverting to heterosexuality upon release. But others were more inventive.

Robert knew that one of the men who worked with him in the laundry never bitched about washing the sheets from the ‘conjugal cabins’; in fact he insisted on doing so. He was a divorced guy without conjugal privileges. He would sniff the sex stains on the sheets and if the stains were fresh enough he would lick them. The man would masturbate whilst sniffing or licking the cunny-juice stained sheets, imagining he was fucking the woman who had secreted her vaginal essences onto the white cotton sheets.

Sometimes, on a rare occasions, a pair of panties or an intimate garment may be found accidently tangled up in the sheets; a real prize for the finder. Necessity was the mother of invention after all and men deprived sex with women could imagine anything to quell their urges. Some men could even imagine that two men dressed in sexy ladies clothing, wearing makeup and high heels, shaking their asses and speaking with feminine allure were real women so long as the men never saw the women’s cocks. Of that Robert was certain because he was living proof.

At first Robert had been unable to function sexually during his wife's conjugal visits after Tig had blackmailed him into providing sexual favours for the men in Seg and Allie had turned him into Bobbie. Robert knew that the issue was mental not physical because he was regularly orgasming during sex as Bobbie. He suspected that it was a combination of guilt and shame. Shame because he was being forced to transform into Bobbie and provide sexual services to men and guilt because despite Robert’s reluctance to do so, Bobbie was increasingly enjoying doing exactly that.

Mandy had noticed the changes in her husband. He had lost weight, shaved off the raggedy beard, which she hated anyway, and had dyed his hair which to her seemed eccentric. Robert had become quiet and withdrawn and worst of all, despite her best efforts, was unable to maintain an erection.

Mandy was overjoyed when Robert was transferred to Brentwood. She knew that he hated his time spent in Smith State Prison which housed violent, repeat offenders or inmates who had exhausted all other forms of punishment. Having been convicted of a white collar crime she found it unfair that Robert was incarcerated in State Prison where he had lived in fear. She had exhausted what little money she had left to pay their lawyers to petition the State to transfer Robert to a minimum security facility which was where he rightly belonged.

Robert had not fared well in Smith. He had become lazy, gained weight and let his hair grow out and ceased shaving. When he was transferred to Brentwood his spirits had soared and he had kept the long hair and his beard but had his long hair styled and his beard trimmed. He stayed a little pudgy even though he was exercising regularly because the food was so good and there was plenty of it.

The icing on the cake was that Brentwood facilitated conjugal visits and Robert and Mandy had taken full advantage of the privilege. She had developed ‘honeymoon cystitis’ after their first conjugal visit because they had done very little other than fuck. But after a while, despite his ardour, he was unable to maintain an erection. Mandy had tried all of her feminine wiles to get her husband hard and even resorted to wearing sexy lingerie. Robert had stooped to satisfying Mandy orally which was nice but she wanted her husband inside her, holding him close as he ejaculated, triggering her own orgasm in the process.

Then suddenly Robert had recovered his sexual vitality and their sex life had blossomed again. Robert had requested that she still wear the sexy lingerie, sheer nylons and high heels when they made love and Mandy didn’t mind one little bit. If that’s what it took for him to maintain an erection then so be it.

What Mandy didn’t know was that Robert was using the Viagra that he pilfered during his visits to Seg. She would also be shocked to learn that during their vigorous fucking Robert sometimes imagined himself in Mandy’s place, dressed as Bobbie, lying on the bed wearing Mandy’s sexy underwear with her legs open being fucked by some faceless man’s big hard cock.

Mandy arrived at Brentwood on Saturday afternoon and was given a cursory search by a female corrections officer and her overnight bag was scanned for contraband. Robert would be strip-searched after the visit to ensure that Mandy had not passed him any contraband but as any infraction of the rules could result in the inmate being returned to state prison, the risk was considered low.

She was taken to one of the conjugal cabins where Robert was waiting for her. He was wearing clean, pressed khaki pants and matching shirt. His hair was tied back in a ponytail exposing his handsome face. He was lean and fit and Mandy was already hot for him.

She remembered the few occasions she had visited Robert in state prison where he had become overweight, bearded and looked despondent. Mandy was delighted when Robert lost the beard, lost weight and seemed to be his old self although she would have preferred that his hair was a little shorter and she was sure that he was dying it. Robert had always worn his hair longer, over his collar, and was proud of his black mane however there was now no hint of the odd grey hair that appeared now and then. That said; Mandy was glad that her husband was being fastidious about his appearance.

Mandy recalled the period of time when Robert had been unable to perform sexually just after he started taking care of his appearance and she put it down to anxiety or possibly depression but it didn’t last long and he was soon back to his old lubricious self and she usually went home a little sore but in a good way. At home in her empty bed she would recall their conjugal visits while she used her trusty vibrator to bring herself to climax. But it was no substitute for the real thing and she was keen to make the most of their time together.

What she didn’t know was that without the Viagra Robert was stealing from Seg, despite his ardour, he would not be able to perform.

Mandy had worn a simple shift dress and flats to the prison but she’d had her hair coiffed and her makeup was perfect because she wanted to look her best for her husband.

After a long sensual kiss they sat at the little table drinking instant coffee and discussed family matters. The sex could wait. They just wanted to be in each other’s company and pretend that they were not inside a prison. They wanted some normality in their lives.

“Are you still getting the money?” Robert asked

“Yes and I know better than to ask too many questions about where it comes from,” Mandy replied.

Mandy guessed, incorrectly, that Robert had been able to hide a lump sum of money from the investigators and had waited until he thought it was safe to trickle small amounts into Mandy’s checking account. It wasn’t a king’s ransom but it was substantial and it helped Mandy and Charlotte immensely. Mandy was careful not to splash too much of it around. Although Robert’s case was old news it might reinvigorate the GBI investigators if Mandy suddenly started spending big on luxury items.

What Mandy didn’t know was that Robert was selling his soul almost every night for the money. Tig used both blackmail and bribery to keep his prison dolls in line.

“How’s Charlotte?” Robert asked.

“She really wants to see you Robert. She misses her father,” Mandy pleaded for what must have been the hundredth time.

“The man in prison is not Charlotte’s father. I don’t want her to see me like this, trapped in a cage,” Robert sighed.

“It’s hardly a cage Robert. It’s more like a working farm,” Mandy regretted trivialising Robert’s situation as soon as she said it.

“It’s still a prison and the guys in here are criminals. I don’t want Charlotte anywhere near this place; you don’t have any idea what happens here,” Robert said bitterly.

Robert held up his hands when Mandy looked alarmed.

“Oh don’t worry Mandy. Nothing really bad happens here but it’s still a place where men are confined,” Robert tried to soothe his wife.

“Charlotte is doing well at college and she’s made new friends,” Mandy changed the subject.

Charlotte’s friends from before Robert was convicted had all abandoned her but she was resilient and had moved on. She wore the fact that her father was incarcerated as a badge of honour. It’s not like he was a murderer or a rapist. As far as Charlotte was concerned her father had swindled a bunch of rich assholes that were so rich that they didn’t even know that they were being swindled.

“She tells me that you're thinking of buying her a car,” Robert raised his brows to his wife.

The only form of communication that Robert had with his daughter was a weekly email exchange. They didn’t mention his crimes or that fact that he was incarcerated. Charlotte told him all about college, her friends and family gossip and Robert told her about working on the farm which was a fabrication now that he was working in the laundry but his wife and daughter didn’t need to know about that or the reason for it.

Mandy tensed, thinking that Robert would disapprove of her buying their daughter a car.

“Something small, unobtrusive and preowned,” Robert smiled at Mandy and she smiled back.

“Your daughter loves you and she will love you even more when she gets her car,” Mandy’s smile became a grin.

Robert couldn’t help but recall the pictures Tig had shown him of Mandy and Charlotte. The realisation that Tig could have them abducted at any time washed over him but the dark cloud passed and they discussed other family matters for a while and then Robert helped his wife to her feet and kissed her.

“You wanna watch me dress?” Mandy squeezed Robert’s cock through his trousers cheekily.

“You bet I do,” Robert grinned at her salaciously.

Robert undressed and lay on the bed and watched while his wife kicked off her flat shoes and shimmied out of the shift dress, cotton panties and brassiere and cheap tan pantyhose. She put on show for him slipping into red satin and lace panties and matching brassiere, fifteen denier tan holdup stockings, red high heeled pumps and finally a red satin chemise.

The Viagra was kicking in and Robert was rock hard. Mandy was a little shocked when Robert had asked her to shave her pubis completely. Back in the day when they were wealthy socialites Mandy had her beauty consultant maintain a ‘Brazilian’ which she had considered racy at the time but completely shaving her vulva before each conjugal visit was now just habit, as was selecting sexy lingerie and heels to wear for her husband.

She did not want Robert to become impotent again and she had to admit that shaving her pussy, wearing the sexy lingerie, nylons and fuck-me shoes made her feel a little whorish which added to the excitement, knowing that they were surrounded by virile, incarcerated men who would love to be in Robert’s place right now. Mandy and Robert did things in the conjugal cabin that they had never done at home in the bedroom.

Mandy would never tell Robert this but she sometimes imagined that several of the prisoners had climbed the fence surrounding the conjugal cabins and were peeking through the curtains, watching them fuck. And she would certainly not tell him that in her fantasies the men broke into the cabin and held her down while each man took his turn with her while she pretended to struggle but enjoyed every second of it.

Both Robert and Mandy had their secret sexual fantasies which embellished their lovemaking but neither of them would ever articulate them to the other. They were in love with each other and they loved making love with each other, the fantasies were just there to pique their imagination. Only Robert actually lived his fantasies in real life and when he did so, he did so reluctantly as Bobbie. At least that what he told himself when he was with Mandy.

Mandy joined Robert on the bed and lay down beside him. Her perfume was fresh, flowery and a little girly and Robert breathed it in and smiled. It was nice and it suited Mandy’s bubbly personality. It was nothing like the exotic Christian Dior Poison which Bobbie wore. For that Robert was grateful because he only had to whiff a scintilla of the erotically piquant fragrance and Robert ‘became’ Bobbie almost instantly. Poison parfum would forever be associated with Bobbie.

Husband and wife kissed, softly at first. There was no need to rush and they took their time exploring each other’s bodies. During their first conjugal visit at Brentwood Robert had been so impatient and sexually fuelled that as soon as they’d closed the door on the conjugal cabin he’d bent Mandy over the table, pulled down her panties and slammed his rigid cock into her clunge and filled her with a week’s worth of spunk. That was the week she spent walking bow-legged with honeymoon cystitis.

When Mandy arrived home from that first visit she had to ease herself into the lounge chair and put a pillow under her ass and Charlotte had teased her mother about it. Mandy had blushed and told Charlotte not to be so obtuse. She knew that her daughter was sexually active because they spoke honestly with each other about such matters but she also knew that her daughter was no slut.

Mandy’s hands slid across her husband’s smooth chest, along his flat belly and finally cupped his hairless scrotum. Robert had begun shaving his body at the same time that he lost weight, dyed his hair and started daily exercising. She believed then and still believed that maybe Robert was trying to recapture his youth. Once he got over his impotence she actually relished stroking, kissing and licking his smooth trim body.

Robert gasped as Mandy began to stroke and gently squeeze his scrotum as she ran her manicured fingernails across his tender flesh. He slipped his fingers inside her bra cup and hefted her bountiful breasts, feeling her nipples engorge when he circled them with the pad of his fingertip. He worked one breast then the other as they lay sideways kissing, Mandy with one stocking-sheathed leg over his body. Robert relished the feel of her nylon-clad flesh on his and kissed her deeply, pushing his tongue into her mouth and swirling it around.

Mandy released his scrotum and took Robert’s sturdy phallus in her hand. She expressed a jewel of pre-ejaculate from the eye and massaged the viscous fluid into his fraenulum and smiled when he hissed into her mouth. She grasped his manhood and began to stroke him and Robert’s hand continued its journey across Mandy’s soft belly down to her panties. His wife had developed a little potbelly while Robert was in prison but the extra weight suited her.

Robert hefted his wife’s clunge, cupping her meaty vulva and gently squeezing it. Mandy gasped and Robert traced the outline of her labia through her silky satin panties. The crotch of her panties was already damp in anticipation of what was to come. He pressed a finger between her fleshy lobes and circled her clitoral hood, sliding the gossamer panty material over her engorged clitoris.

Mandy loved the feel of it but could hardly wait for Robert to ease the gusset aside and push his fingers into her cloying crevice or better yet, roll her over on her back and thrust his engorged manhood deep into her vagina. But Robert was intent on extending the foreplay.

Mandy wriggled free of his embrace and she lowered her face to his nipples and suckled and nibbled on them while she slowly stroked his penis. Robert eased her face down his body. As much as he liked having his nipples sucked it reminded him too much of the men in Seg suckling on Bobbie’s nipples and he wanted to keep Bobbie out of his conscious thoughts for now.

Mandy worked her way down Robert’s body, her long blonde hair tickling his flesh pleasantly while the tip of her tongue left a trail down his flat belly, circled his bellybutton and finally found his penis. Robert was about to be rewarded with one of Mandy’s infrequent blowjobs.

“You don’t have to do that,” Robert murmured but Mandy ignored him and took his manhood into her mouth.

“I know you like it and I want to feel you in my mouth. I miss you and I love you,” Mandy looked up at him.

With his cock lying on her cheek, her smoky eye makeup, teased blonde hair and red lipsticked lips she looked like a porn queen. She engulfed Robert’s cock and began to suck on it.

Robert had heard the joke many times in prison: “What are four words that no man has ever uttered: ‘stop sucking my dick!’”

This was probably true but the fact was that his wife was a lousy fellatrix. Yes, it felt pleasant when she took him in her warm, wet mouth and clamped her lips around his penis. Then she would bob her head up and down on it, sucking on it like a candy cane but she had no idea how to use her tongue. Robert would dearly love to teach her some of Bobbie’s tricks but he’d put up with her mediocre fellation before he went to prison and Mandy might be more than a little suspicious as to how her husband was suddenly such an expert at cock sucking all of a sudden.

Robert laid back and enjoyed Mandy’s ministrations as best he could. She certainly wasn’t terrible; she just wasn't good. He enjoyed the feel of her lipstick-coated lips on his shaft and he liked that she gently cupped his balls but where was the tongue? On the rare occasion that she actually licked his fraenulum or his glans he moaned with delight and told her how wonderful it felt, but she just couldn’t take a hint.

Sucking his cock like that Mandy could keep him hard all day but she’d never make him cum. After a while he eased her face away from his groin and smiled down at her.

“That was wonderful but I want to make love to you darling,” he whispered knowing that the interconnection of love and sex was what Mandy adored.

Whilst Mandy tolerated Robert bending her over the table and rutting her, or pulling her ass into the air and fucking her doggy-style, her preferred coital position was missionary so that they could kiss and look into each other’s faces while they ‘made love’. Mandy detested the word ‘fucking’.

Robert rolled Mandy onto her back and lay on top of her. She locked her legs around his flanks and scissored them so that her nylons rubbed on his tender flesh. She knew that Robert loved the feel of her stockings and pantyhose. Before he was incarcerated her husband would take advantage of any situation to play with her legs whenever she wore hosiery.

Mandy took her husband’s turgid tool in her hand and guided it to her vulva. Easing aside the gusset of her panties she positioned his glans inside her labia. Robert felt the warm wetness of his wife’s quim and slowly slid the full length of his tumescence into her vagina.

Mandy sighed with contentment as her husband slotted his manhood inside her aching sheath. To her it was the ultimate expression of love between a man and woman. She was not a virgin when she married Robert but there had been only one other boy before him. Despite her fantasies she was true to her husband and adored it when he mounted her.

As Robert’s steely rod slid into Mandy she wrapped her arms around him and kissed him, holding him close, adoring the feel of his cock deep inside her. She was moist and becoming wetter. Mandy had a way of undulating her vagina so that it clung to Robert’s phallus; almost milking it as his cock slowly slid it in and out of her. She loved it when they made love this way, taking their time, extracting every scintilla of pleasure from each other’s bodies.

Robert was tempted to drive Mandy into the bed and fuck her hard and fast but he knew that she liked their first encounter to be tender and loving. The torrid, carnal, exploratory sex would come later.

Robert kissed Mandy. His tongue explored her mouth as he lay on top of her, languishing in the feel of her body swathed in the satin chemise with her legs wrapped around him clad in her slinky stockings. He barely moved but he made sure his pelvis pressed on her clitoris as he ground against her, feeling her shudder and hearing her mew into his mouth as waves of pleasure erupted from her sensitive nubbin.

Bobbie tried to enter his psyche and force him to imagine that it was Bobbie lying on the bed dressed in her finest lingerie with some faceless but undoubtedly handsome man mounting her, pressing his engorged phallus into her slick, tight anus.

Robert physically shook his head to expel Bobbie from his consciousness and he started to slowly fuck his pretty wife.

“Is anything wrong?” Mandy asked when she felt Robert flinch.

“It’s nothing darling, just a little cramp,” Robert lied and closed his mouth on Mandy’s and began to thrust his cock in and out of her tight sheath.

Mandy giggled almost like a schoolgirl and locked her arms and legs even tighter around her husband’s lean body and rose her groin up off the bed to meet his thrusts. She was well on the way to climax and she adored that Robert knew exactly when to start ploughing her fleshy slot.

“Yes honey, go harder… go faster,” Mandy nibbled Robert’s earlobe.

Robert obliged and began to drive his throbbing member in and out his wife’s slick cunt, pulling his cock almost all the way out of her then driving it back in all the way, grinding his pubis into her vulva so that he stimulated her clitoris. Mandy raked her fingernails down Robert’s back than she locked her ankles in the small of his back and moaned and shuddered as she climaxed.

Robert felt her cunt quiver and undulate, pumping his cock, milking it of his hot creamy load as he ejaculated deep inside her. He stifled her moans with his lips, driving his tongue into her mouth, wriggling his tongue, tasting her as he planted his seed deep in her womb.

His cock felt like it was being gripped by a silken glove and squeezed, his flesh tingled as Mandy’s silky negligee and gossamer hose grazed against him as he she clung to him, her body shuddering, almost convulsing.

They lay in each other’s arms and held each other in wedded bliss, thinking only of how much they loved and adored each other. Brentwood Correctional Facility was a million miles away from their thoughts but as Robert slowly began to come down from his orgasmic high Bobbie slipped into his consciousness and reminded him that she was waiting.

“Have you ever thought about taking a lover?” Robert asked as they lay on the bed in the dark just before they fell asleep.

They had made love twice again and Mandy’s vulva was puffy and her vagina a little sore. The Viagra was still working and although there was no way that Robert could climax again tonight he was still hard. If the Viagra wore off during the night he would pop another one in the morning while Mandy wasn’t looking so that he could give her their customary farewell shag.

“Why would you even ask me that?” Mandy sounded wounded and was suddenly wide awake.

“I think I would understand. You have to make the effort to visit me every week and we have conjugal visits only once a month. You are a beautiful woman in your prime and your husband is locked away in prison,” Robert sighed.

“What the fuck has brought this on?” this from a woman who seldom swore.

What had brought it was Robert’s intense guilt at living a double life. The immense guilt he felt because he had placed his wife and daughter in danger was never far from Robert’s thoughts. Ever since he had submitted to becoming Bobbie, Tig Hansen had made no further threats against Robert’s wife and daughter but Tig didn’t have to. The money that trickled into his numbered account which Robert then siphoned off to his wife in amounts that would not draw attention was both a reward and a warning: plata o plomo Silver or Lead! But before the lead ended their lives, his wife and daughter would endure atrocities he couldn’t bear to think about.

“I’m just saying that’s all. I’ve been locked up in prison for so long and I still have the rest of my sentence to serve. I’d understand if you found solace with another man,” Robert whispered.

“What the fuck Robert! What has happened to you? You haven’t found someone have you? You haven’t gone… what is it they say… prison gay?” Mandy sat up and shook Robert’s shoulder.

“No!” Robert shouted.

But the truth was far worse than being ‘prison gay’. He was a prison doll. That is to say that Bobbie was a prison doll who coexisted inside Robert and the guilt he felt when he was with Mandy was nearly overwhelming. If Mandy took a lover it might help assuage his guilt.

“Well I won’t be taking any lovers Robert, with or without your permission,” Mandy huffed angrily and rolled over on her side facing away from her husband.

“Not that I haven’t had a quite a few offers mind,” she added bitingly before she fell asleep.

Where Mandy worked as a secretary in a financial institution the dress code required suits and ties for men and the equivalent for the female staff. She thought pantsuits made her look dowdy so she wore skirt-suits, hose and heels. With her teased blonde hair, big blue eyes, pretty face, long legs, ample breasts and curvy figure, Mandy attracted attention from the office incorrigibles. They knew her husband was out of the picture and circled her like sharks.

Mandy would never admit it but she was quite flattered that men still found her attractive but she had no interest in becoming the office trope who spent evenings in seedy hotels with married or divorced men who wanted only to put another notch on their bedpost. She loved Robert and their monthly conjugal visits and the little battery operated plastic toy that she kept in her bedside table sated her desires.

But the longer Robert spent in prison the more she became uncertain about the fidelity and endurance of their marriage. She had put up with Robert's bizarre behaviour: the long dyed hair, his smoothly shaved body, fluctuating weight, his insistence that she shave her mons and wear sexy lingerie, the brief period of impotence… and now he was suggesting that she take a lover.

What the fuck was happening?

The next morning they made love one last time before Mandy left. There was no mention of the brief heated discussion they’d had the night before. Neither of them wanted to part on a sour note.

As Robert underwent the strip search before he went back to D Wing he was very conscious of the fact that Bobbie would be required in Seg that evening. But this was his life now and he’d become accustomed to it.

Tig nodded at Robert as he walked down the corridor to his room and Robert returned the nod. Nothing had to be said. Bobbie would be required in Seg that evening.

To be continued

Prison Dolls - Chapter 3

Author: 

  • Michele Nylons

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Blackmail
  • Caught with Consequences
  • Crime / Punishment
  • Fresh Start

TG Elements: 

  • Bad Girls / Promiscuity
  • Corsets
  • Panties / Girdles
  • Prostitution

Permission: 

  • Posted by author(s)
Prison Dolls  Edited.jpg

Chapter Three - Red Roses Dropped On Fresh Snow

Traitors – Time Takes Its Toll

The thing about prison is that you are seldom alone… but you always feel like you are.

Robert kept to himself and the other inmates in D Wing mostly kept away from him anyway. Most of them knew about Bobbie and Marilyn and kept their distance, especially when Tig was around because of his overt aggressiveness.

Except for when she presented as Marilyn, Maurice Shrew had little to do with Robert. Bobbie and Marilyn weren’t competitors but they just had nothing in common with each other other than being transvestites who serviced the men in Seg. There were two other openly gay men in D Wing who were friendly with Maurice and Robert suspected that Maurice was having sex with both of them. Maurice only presented femme for the money and during the day he went to work keeping book at the prison farm while Robert worked in the laundry.

After living a double life for what seemed like an eternity, Robert no longer dreaded dressing as Bobbie and carrying out her duties in Seg. In fact Robert began to look forward to it, or at least his alter ego Bobbie did. Robert was worried that Bobbie was taking over his life. She drifted in and out of his conscience so freely now.

When he laundered his and Marilyn’s ladieswear in the laundry Bobbie would remind him that he needed new lingerie or dresses or heels. She would take over his psyche when Robert placed his orders with Tig. She was reluctant to let go when Bobbie returned to her room after spending the evening in Seg. If he was honest with himself, Robert would have to admit that he was more comfortable when he was Bobbie… and that was worrying. Existing as Bobbie was an escape. An escape from prison, an escape from Robert’s bland life, an escape from Robert’s responsibilities and an escape from his family who seemed to be distancing themselves from him.

He and Mandy were drifting apart. Although they still took advantage of the monthly conjugal visits they were distant with each other. Robert suspected that Mandy was only attending the conjugal visits to perform her ‘matrimonial duties’. Except for the sex, the closeness they felt was no longer there. They were a man and woman who fucked each other out a sense of obligation. Mandy had almost ceased attending weekly visitation saying that the long drive was arduous and sitting in the prison visiting room made her depressed and Robert didn’t protest. He felt the same.

Their correspondence was rudimentary, mainly talking about finances, their daughter Charlotte who would soon be graduating, and gossip about the few relatives who had remained close. With Robert’s stipend supplementing her wages Mandy was able to pay the residency fees at Middle Georgia State University and Charlotte had moved into the college residency. Charlotte had a steady boyfriend and she visited home less frequently.

The truth of the matter was that Mandy was lonely and she had started dating a divorcee at work. At first it was just friendship, someone to go to dinner with, see a movie or go to the theatre. Then they went dancing and ate late night suppers and then they started seeing each other on the weekend and finally Mandy had ended up in his bed.

The guilt that Mandy felt was nearly as crushing as the guilt that Robert felt about keeping Bobbie’s existence a secret. They both felt like traitors. Mandy started to hint that she was friendly with a man from her office and rather than being horrified Robert was relieved. He guessed that they were fucking and Robert understood that the relief he was feeling was guilt transference. It had gotten to the point where he perceived Mandy as the guilty person in their relationship. He convinced himself that he was being forced to be Bobbie but Mandy had become an adulteress of her own free will.

To make matters worse Bobbie and Tony Siceresso were not just fucking in Seg, they had become secret lovers. Bobbie was always Tony’s favourite, he hardly ever had sex with Marilyn and he continued to do so only to avert any suspicion that Bobbie was anything other than a whore to him. Even so, Tony was teased by the others about his preference for Bobbie over Marilyn.

“She’s just a better fuck,” Tony said flippantly when questioned about it.

Their relationship had developed slowly at first. During the first few months of her existence Bobbie had dreaded visiting Seg. Eventually transforming from Robert to Bobbie had become easier and Bobbie was able to slide easily into Robert’s consciousness and take over. Bobbie actually liked being who she was. She had shed the excess pounds and she tried different makeup styles to match her moods and her outfits and tried wearing wigs of differing styles and colours. She became fashion conscious and extended her wardrobe.

But at first the sex was difficult. She realised that the men in Seg had different demands. Mike Giacomo she called Doctor Jekyll and Mister Hyde because sometimes he was affectionate and then on the turn of whim he could be cruel and demanding. Sal was a gentle old soul whose penchant for the dolls waxed and waned. He wasn’t very good at sex but he enjoyed their company. Petey Gruffalo liked sex but was prone to post-coital regret. He loved being in the company of the dolls and he liked taking them back to his room but once he had climaxed he wanted them gone. Joey Malzone also enjoyed the company of the dolls but he used them the same as he would use any of the whores that he used when he was a free man. There was little real affection.

Bobbie soon worked out how best to please the men in Seg and moderated her behaviour accordingly. She was enthusiastic and affectionate when it was called for or she just behaved like a whore when needed and sometimes she just lay on her back, knelt on the bed or stood against the wall with her skirts hiked up while she was used.

The sex was so frequent that it became tolerable. Then she began to enjoy it. Not always but on most occasions she would become sexually aroused and actively participate. She always kept her genitals covered but more often than not she would become tumescent and sometimes climax. The first time this happened was with Tony Siceresso.

Bobbie recalled the first time she and Tony Siceresso were together intimately.

Bobbie and Tony – A Blossoming Romance

The word entertain had taken on a new meaning. It meant everything from engaging in polite conversation, to dancing, to playing games with the men but mostly it meant providing sexual favours. When Tig told her at lunch that she would be required to entertain in Seg that night, it meant that she was going to be fucked or at least be used orally. When she attended Seg she was usually in the company of Marilyn but sometimes only one of the dolls was required depending on the disposition and the needs and wants of the men in Seg.

As always she took advantage of the alcohol and drank as much as she could to numb her senses. One evening a few months after her debut, she and Marilyn went to Seg as usual. Sal and Mike weren’t present and after a few drinks Joey led her to his room but he only wanted a quick blowjob and Bobbie satisfied his needs and he sent her back to the playroom. Petey Gruffalo was getting cosy with Marilyn and Tony poured Bobbie a drink and sat down beside her.

“Here, you look like you could use this,” Tony Siceresso handed Bobbie a drink and offered her a cigarette.

Georgia had banned tobacco use in all of its prisons long ago but the men in Seg weren't subject to any restrictions and some of them smoked. Robert had given up smoking in his twenties and still didn’t smoke. Bobbie had taken it up immediately as another coping mechanism along with the alcohol. It helped calm and distract her while she entertained in Seg.

Bobbie leaned forward so that Tony could light her cigarette. She absentmindedly placed her hand on his knee as she leaned in and almost and as soon as she was aware of the transgression she snapped it back. Bobbie was still uncertain about the rules. Was she supposed to be forward or was she supposed to be demure? She envied that Marilyn seemed to know exactly how to act. She seemed to know when to be flirtatious and when to be reserved, Bobbie was still feeling her way.

Tony took Bobbie’s hand and put it back on his knee.

“I like your nailpolish,” he commented looking down at her bright red fingernails.

Bobbie just nodded and gulped her drink.

“How are you settling in?” he asked.

Bobbie knew that she had to be careful. She recalled what Allie Kat had said to her: ‘What’s the number one rule - don’t show your dick and never break character.’ She also remembered what Mike Giacomo had said to her: ‘We don’t want to hear anything about your life. We aren’t interested.’

“Just fine. I enjoy the luxury of this place,” Bobbie replied coolly.

Tony chuckled.

“You are a very beautiful woman,” Tony stroked her cheek and Bobbie blushed.

She finished her drink in one gulp and crushed out the cigarette.

“Wow! You are one thirsty girl,” Tony chuckled.

“I’d like to take you back to my room so we can have a drink in private,” Tony placed his hand on top of hers.

Bobbie guessed that ‘have a drink in private’ was a euphemism for sex.

“Sure, I’d like that,” Bobbie lied.

She just wanted to get it over with so she could return to D Wing.

Tony led Bobbie to his room and closed and locked the door. Bobbie sat on the big sofa. It was a large modular ottoman that functioned as a day bed. Bobbie perched herself on the edge, her ankles crossed demurely while Tony went into the bedroom. He returned wearing a short velvet robe tied at the waist. Knowing that Tony was naked under the robe just confirmed that he wanted her for sex, not for conversation. She sat primly, resigned to her fate.

Tony poured them both a drink. This was unusual. Normally the men wanted to get right down to it but Tony didn’t seem to be in a rush. Bobbie figured that because Marilyn was entertaining Petey and the others were busy doing whatever they did in the office that Tony had decided not to rush but she knew that she would likely end up on her knees before too long.

Tony sat down beside her and gave her the drink and they talked. Tony told Bobbie that his wife had divorced him not long after he was incarcerated. Their marriage was on the rocks before he went to prison and as they had no children his wife was happy to settle for the house and a ton of cash and agree to an uncontested divorce. The men seldom discussed their personal lives and Bobbie was surprised.

“Allie sends her regards by the way,” Tony segued the conversation completely, throwing Bobbie into confusion.

Allie had told Bobbie that once she was released from Brentwood that she was to going to be rewarded for her services and had been offered a well-paid position hosting the drag show at one of the Siceresso’s nightclubs.

“She’s managing the Dream Palace nightclub in Miami and has begun transitioning,” Tony stated as if he was just talking about a mutual friend.

This surprised Bobbie. The men in Seg never acknowledged that the dolls were in fact female impersonators and seldom spoke about them outside the context of sex. Bobbie remained silent but attentive.

“I own the Dream Palace. It’s one of the many legitimate businesses that I retain in Miami,” he continued.

“Allie keeps in touch?” Bobbie ventured.

“Only with me on a personal level, not with the others,” Tony smiled and Bobbie couldn’t help but smile back.

“She was never just a doll to me. We were… intimate,” Tony surprised Bobbie yet again.

He placed his hand on hers again and intertwined his fingers in hers. It was such a gentle intimate gesture that Bobbie was taken aback. Then Tony leaned in and nuzzled Bobbie’s neck, inhaling her perfume, kissing her delicate flesh softly and tenderly. Bobbie sensed a peculiar sentiment materialise and then she realised that Tony was displaying genuine affection.

Bobbie turned to face Tony. He was handsome and faultlessly groomed. His hair was thick and black, his olive complexion and muscular body would be alluring to most women. Up until now Bobbie had not considered the handsomeness of the men in Seg. She gauged them by their temperament and their desires. They were innominate entities who treated her decently enough in the company of their compatriots but in the bedroom they were just demanding dominant men who used her for their pleasure.

Bobbie felt totally feminine when she metamorphosed but that was uniquely self-induced. She knew it was more than a survival technique but up until now she didn’t acknowledge it. She knew that the men in Seg saw her as a pretty woman but there was no element of attachment or reverence. But somehow it didn’t feel that way with Tony. Maybe she was reading too much into it?

“You were intimate?” Bobbie asked; her voice just above a whisper.

“Of course we fucked. We both liked to fuck,” Tony chuckled.

“But I felt something for her beyond lust. We connected,” Tony was suddenly serious again.

“Prison is a lonely place despite the fact that I live in a palace with four other men. The intimacy I shared with my wife had all but dissipated by the time I arrived at Brentwood. Allie and I formed a relationship that I cherished and that I would like to replicate with you,” Tony squeezed Bobbie’s fingers gently.

“She never told me. Of course she told me that I would be performing sexual favours but she never went into detail about her relationships with the men in Seg. I assumed she was just another concubine like me and Marilyn,” Bobbie replied, putting her drink down on the coffee table.

“She didn’t tell you about us because Allie could keep a secret. If the others found out that Allie and I were actually lovers and that I had genuine feelings of affection for her, that I saw her more than just a whore, there would be repercussions for us both,” Tony sighed, placing his drink down beside hers.

“I’ve told you too much too soon Bobbie but I trust you. Let’s just see what develops between us, take it as it comes so to speak. One thing Bobbie. What happens in this room stays in this room. No one can ever know,” Tony leaned in and kissed Bobbie on the mouth.

The kiss lingered and soon tongue was introduced and they lay down on the sofa and cuddled and canoodled. Bobbie lay on her back and Tony lay down beside her, kissing her, stroking her cheek and then he moved his hand down her torso to her breasts.

Bobbie was wearing a black leather miniskirt and a mauve satin blouse and Tony slowly unbuttoned it and slid his hand inside. Bobbie no longer wore breastforms so Tony was able to caress her nipples through the translucent material of her lacy brassiere.

Bobbie gasped as Tony gently caressed her tiny teats. When he lowered his face to them she guided his mouth from one nipple to the other as Tony lapped and nibbled on the sensitive buds. She was becoming tumescent and she could tell that Tony was too. She could feel the heft of his cock pressing against her belly. She instinctively reached for it knowing what was expected of her.

Tony caught her hand as it slipped inside his robe and gently removed it.

“There’s no rush Bobbie. I’ve waited quite a while for us to be able to be alone together without having to rush,” Tony smiled down at her and kissed her again.

The kiss was soft but the yearning was undercurrent. Bobbie suspected that Tony could quite easily mount her and satisfy his base urges but he was restraining himself. He was behaving more like a lover than a john.

He kissed her some more and Bobbie enjoyed every second of it. The featherlight pressure as their lips touched, the delicate way in which he slipped the tip of in tongue into her mouth. The way he was holding her like she was precious, not like some fuck puppet. His fingers played with her breasts and then slowly began the journey down her torso, down her skirt and finally came to rest on her legs.

He stroked the back of her knees, his fingers tickling the little wrinkles in her pantyhose and Bobbie shuddered with delight. Then his hand began to creep upwards, under her skirt, tracing her thighs, finally coming to rest in the crevice where her legs joined her hips. He stroked the delicate flesh there and Bobbie gasped into his mouth.

His touch was so tender and erotic. It was as if Tony was trying to seduce her. She yearned for him, searching out his manhood but once again he brushed away her hand and instead she laced her fingers behind his neck and returned his kisses, slipping her tongue into his mouth, pressing herself against him.

Tony’s fingers slid across the front of her panties and Bobbie froze. The men would often play with her ass but they never touched her pubis. She knew that the men in Seg never wanted to break the illusion that she and Marilyn were women.

Bobbie put her hand down there and gripped Tony’s wrist and looked at him with trepidation.

“What are you doing?” she whispered.

“What I’ve be aching to do honey,” Tony smiled at her and shook off her grip.

He pressed his lips to hers and drove his tongue into her mouth. His fingers continued their journey across the front of her panties. Then moved up to her waist and slipped inside the waistband of her pantyhose and continued down between her legs.

Bobbie shuddered and gasped as Tony freed her penis from between her legs. Her cock was semi-tumescent and Tony laid it flat against her belly and hitched up her panties to cover it. Bobbie’s testes descended into her scrotal sac. Tony stroked the bulge in Bobbie’s panties as he kissed her passionately and Bobbie was filled with trepidation but also lust. His fingers brushed her satin panties against the tight nylon of her pantyhose which swathed her now fully erect penis. It was heavenly.

“Do you like that Bobbie?” Tony broke the kiss and smiled at her.

Bobbie’s response was to pull Tony’s face to hers so that she could kiss him and wriggle her bottom appreciatively. She felt Tony smile around the kiss and she realised that this had been his plan all along. No wonder he had sworn her to secrecy.

Tony stroked her cock through her panties and Bobbie reached for his. This time he did not bat her hand away and she found him turgid, his glans dripping precum. His penis felt huge in her delicate fingers and she began to stroke it and was rewarded with a gasp and a shudder as Tony felt Bobbie’s fingers manipulate his throbbing manhood.

She was gentle and fondled his cock softly, sensing that Tony was in no rush to consummate their tryst. They kissed and canoodled and once again Bobbie was overcome with a feeling that she and Tony were actually making love, not just having sex. There was no urgency, no race to climax, they were tender with each other and Bobbie was surprisingly delighted.

Tony nicked a little hole in the front of Bobbie’s pantyhose and guided her penis though the hole and took it in his hand. Bobbie was at once excited and trepidatious. None of the men in Seg had ever touched her penis, not even through her panties and here was Tony stroking her naked flesh.

They fondled each other genitals, cupping scrotums, stroking shafts, tickling fraenulums, their kisses becoming progressively more passionate. They edged each other towards climax and backed off when each sensed the other was close.

“Have you done this before?” Tony asked and with some difficulty he poked Bobbie’s hard cock back the through the hole in her pantyhose and smoothed her pantyhose and panties back in place.

“Have I done what?” Bobbie whispered.

“This,” he replied and rolled on top of her and pressed his cock against hers.

Tony kissed her passionately and she put her arms around him and lifted her legs and locked them around his waist. He loved the feel of her pantyhose on his tender flesh and she loved the feel of muscled body lying on top of her. She felt feminine and appreciated and also lecherous.

His cock pressed on Bobbie’s through the fabric of her slinky panties and hose and they both enjoyed the sensation of cock rubbing on cock. Their kisses became more passionate and then frenetic as they rutted against each other. Bobbie raked her nails down Tony’s back and buffed her silky-hosed legs against Tony’s flanks; he pressed down on her, grinding his cock against hers, relishing the sensations.

“I’m going to cum,” Bobbie whispered into Tony's ear as she felt her climax welling up from deep inside her.

Her scrotum was roiling and ready to release her load. Tony’s cock was tingling with delight as he rubbed it faster against Bobbie’s panty-clad phallus. He felt his orgasm begin to build.

Tony broke the kiss and pushed himself up with his forearms so he could see their cocks frotting against each other and Bobbie shuddered and Tony smiled when he saw a globule of warm semen bubble through her panties. He rubbed his cock in the puddle of spunk and smeared it all over her panties and then he ejaculated too and his own seed comingled with hers as his orgasm washed over him.

Bobbie pulled him down and smashed her lips against his and drove her tongue into Tony’s mouth as she writhed and wriggled beneath him, pressing her cock against his as it juddered and spewed forth her creamy issue. The feel of Tony’s quivering organ spilling his seed on her pantied penis was ecstatic.

The two lovers kissed and cuddled and rutted and ground against each other, their cocks smeared with each other’s warm semen. Even after their orgasms had subsided they lay in each other’s arms and kissed and caressed each other.

“Did you like it?” Tony asked.

“I can’t believe you did that,” Bobbie gasped.

“Oh, I haven’t finished yet honey, that was just the appetiser,” Tony smiled down at her.

Bobbie was used to being dismissed once the man using her had climaxed but Tony clung to her and kissed her. They started all over again, Tony kissing and nibbling her tiny breasts, fondling each other’s cocks, urging each other on. Neither of them had become fully flaccid, they both maintained semi-erections and Bobbie felt Tony’s cock become fully engorged and to her amazement so did hers.

“Your cock is amazing,” Tony whispered as he ran his finger along the length of Bobbie’s hard phallus.

Bobbie was shocked. The men in Seg never acknowledged that their dolls had cocks. She just didn’t know how to reply because she had been conditioned never to talk about her penis while in Seg. Tony wasn’t expecting a reply anyway because he popped Bobbie’s penis out of the little hole in her cum-soaked pantyhose and began to stroke it again.

Bobbie sighed as Tony’s fingers fluttered expertly along her rod, eliciting little flowerets of pleasure. She reached for Tony’s huge cock, her fingers barely able to encircle the girth of it, and she returned the favour. They masturbated each other while they kissed, slowly building the intensity, their kisses becoming more fervid and their hands working faster, their cocks growing harder.

Tony took his hand away from Bobbie’s cock and he slipped it between her buttocks and made another hole in her pantyhose and slipped a finger into her anus. As usual she was pre-lubricated and it slid in easy so he slipped in a second finger and Bobbie gasped. But it wasn’t from pain, it was from pleasure. Tony knew what he was doing and he used the pads of his fingertips to massage Bobbie’s prostate. Her cock began to dribble precum in a continuous stream.

“Are you ready?” Tony whispered and Bobbie could only nod.

She’d never been asked that before.

Tony loomed over and lifted her legs and placed her ankles on his shoulders and he lined up his cock with her sphincter. He nudged his glans into the puckered bud and felt Bobbie tense, then she relaxed and Tony pushed the bulbous head of his cock inside the tight ring, stretching it open.

Bobbie thought her sphincter was going to tear as Tony’s bloated glans stretched her wide open. There was a slight sting and feeling of fullness but the pain was minimal.

Tony kissed her and stroked her and fondled her, just the tip of his cock inside her. He was patient and waited for Bobbie to become accustomed to the girth of it. When he felt her relax again he pushed an inch of cock inside her and Bobbie hissed so he stopped. His cock felt like it was being squeezed by a velvet glove.

“Are you ok?” Tony whispered.

“It’s big Tony but it feels wonderful,” Bobbie admitted.

She placed her lips on his and kissed him, feeling the fullness of his manhood dilating her anus. There was a deep ache but it was not unpleasant and her stretched sphincter was emitting ringlets of pleasure as the girth of Tony’s penis lit up the sensitive nerve endings.

Bobbie wriggled her bottom indicating that she was ready for more and Tony obliged, pushing in another inch or two, feeling Bobbie’s tight anus open like a tight furrow. She gasped again and mewled in his mouth but she clung to him lovingly. Then Bobbie surprised him and she wrapped her arms around his neck and used it as a fulcrum as she lifted her buttocks up off the couch and impaled herself fully on his mighty appendage.

As Tony’s big cock slid all the way inside her, Bobbie wanted to scream but the scream would have been a combination of pleasure and pain. His cock stretched her rectum until she thought it would split but under the deep ache was also a deep resonance of rapture. Her sphincter felt like it was lit up like a string of fairy lights, twinkling little sparklets of pleasure, while a deep reverberation of pleasure began to emanate all along the walls of her tight hole.

Tony took Bobbie’s cock in his hand, drove his tongue into her mouth and raised himself up and began to fuck her. Bobbie had never felt such pleasure before. Tony’s cock filled her void completely and lit up every nerve ending, the base of his cock stretched her sphincter which radiated ringlets of pleasure very time Tony thrust his huge hard cock inside her. Her prostate was stimulated to such an extent that her cock was dribbling a torrent of pre-ejaculate which Tony used to lubricate her penis as he stroked it.

Tony could feel Bobbie’s spongy mass enveloping his hard cock and it rippled and undulated as he drove his cock in and out of her, almost extruding his essence. Bobbie’s cock was throbbing in his hand as he caressed it. He alternated between softly massaging it and viciously stroking it. Their tongues were entwined and Bobbie had lowered her legs from his shoulders and locked them around his waist, drawing him into to her. He could feel her need, her wanton lechery and Tony obliged and began to jackhammer his cock in and out of her tight asshole and stroke her cock faster and harder.

This time Bobbie did scream with delight as freshets of hot spunk erupted from her cock. She pulled Tony tight and screwed her ass into his pubis, extracting every scintilla of pleasure from the monster cock that was impaling her tight anus. She felt Tony’s cock shudder and throb as Tony held her close, driving his tongue in her mouth as drove his cock all the way inside her and ejaculated.

They clung to each other, pressing themselves tight, Bobbie grinding her ass and Tony grinding his pubis as their orgasms washed over them. They squeezed very ounce of pleasure from each other until they were sated and Tony lay on top of Bobbie spent and exhausted.

Bobbie quite liked the weight of his body on top of her. It was comforting and pleasant and Tony was still kissing her but he was kissing her softly and tenderly, his needs met, their passion spent. Eventually Tony’s cock contracted to the point where it slipped from Bobbie’s anus. A flood of semen gushed from her still gaping sphincter and it was soaked up by her pantyhose and panties. It took a little while for Bobbie’s sphincter to close because Tony had stretched it so wide.

After the sex Bobbie and Tony lay in each other’s arms, caressing and kissing each other. This was divergent to what usually followed sex with the Siceressos. She was usually shown the door or escorted back to the lounge or playroom and seldom was any affection shown. Bobbie actually preferred it that way: the compliments, the interplay and the canoodling when she was in the company of the men; the rollicking sexual encounter in the bedrooms without any real attachment with the realisation that the dolls were just a convenient replacement for ‘real women’. It was another means of self-justification to Bobbie.

But this wasn’t that. Tony had shared intimate details of his personal life. He had intimated that he and Allie had a personal relationship that exceeded the bounds of sexual gratification. It seemed, at least for now, that Tony was interested in fostering a similar relationship with her.

He insisted that she take a shower and use his ensuite for as long as she liked and Bobbie enjoyed the luxury of it. She undressed and took a long hot shower and then she fixed her makeup. She took a new pair of pantyhose out of her purse and threw the ones with the holes, drenched in semen, into the little bathroom tidy. She tucked and took a fresh pair of panties from her purse and put them on, then her bra then her skirt and blouse. She stepped into her heels reapplied her makeup and brushed her hair and came out of the bathroom refreshed and smelling of Dior Poison.

“You look gorgeous as always sweetheart,” Tony greeted her; the endearment not lost on Bobbie.

He kissed her tenderly and led her back to the sofa, not to the door which was what Bobbie had expected.

Tony had made her another drink and they shared a post-coital cigarette sitting across from one and other.

“You know this has to be our secret right? It could be a matter of life and death for me,” Tony blew smoke across the room.

“It’s like the ‘Just One Goat’ joke in a way. These guys think it is ok to fuck a tranny in the ass, kiss her, have her blow them, dance with her… you know what I mean. But you touch her dick and you're a fanook forever,” Tony laughed nervously to hide the seriousness of the situation.

“Yeah. Like the other joke. ‘I’m not gay but I once fucked a guy who was,’” Bobbie regretted saying it as soon as the words come out her mouth.

“I'm sorry Tony I know you aren’t gay. I’m not gay. I'm’… I’m… I’m…” Bobbie struggled to find the words.

Tony got out of chair and sat down next to her and held Bobbie close.

“You are what you are honey. You're special to me. Let’s just keep it to ourselves shall we?” Tony leaned in and kissed her then he helped Bobbie to her feet.

He opened the door to his room escorted her to the door of E Wing like a gentleman.

“See you tomorrow.” He whispered and kissed her softly on the cheek.

Bobbie left Seg that evening more confused than ever. How could she feel affection for one of the Siceressos? She wasn’t really a woman, despite her increased feelings of femininity. She wasn’t doing this willingly. The ever present threat to Mandy and Charlotte and the monthly stipend were the only incentives that made Robert submit to handing over his mind and body to Bobbie. This was something bizarre in a situation that was already unbelievably bizarre.

Bobbie looked at the clock on the bedside table and realised that she had been back in her room for over an hour and had not surrendered her psyche back to Robert. She took off her makeup, disrobed and showered and Robert came back into the consciousness of their shared body.

Robert stared up at the crack in the ceiling and did the arithmetic, counting how many months he had left in Brentwood, converting it to weeks and then to days. He willed the crack in the ceiling to speed up its inevitable journey towards the light fitting. Then this would all be over and things would return to normal, whatever normal was.

Bobbie tried to slip into his consciousness and he pushed her down. Robert was overwhelmed by guilt.

Bobbie and Tony being secret lovers made things both better and worse for Bobbie. Bobbie cherished the time she spent alone with Tony. It wasn’t just that the sex was good, they had become connected. But it made having sex with the others feel like she was betraying him and she felt jealous when Tony had sex with Marilyn, even though he told her he was doing it only for appearance sake.

Tony had unfettered access to the outside world but Robert Valentine’s phone calls and email were subject to interdiction and censorship so Tony passed on Robert Valentine’s email address to Allie and she and Bobbie started to correspond. Bobbie’s consciousness took over whenever Robert read Allie’s emails because Allie was conversing with Bobbie not Robert.

Of course there was no mention of Seg or of prison dolls in their correspondence but Allie told Bobbie about her new life in Miami. How she felt that she was finally living the life she had meant to be living as a trans woman. Allie had found a man who loved her, who was devoted to her and she was falling in love with him. Bobbie had to admit to feeling jealous. She and Tony were lovers but they weren’t in love, at least the word love had never been uttered.

They used subtle code. ‘I hear you and Mister T are getting along. I was very friendly with him too. He really helped me get through my time while I was incarcerated,’ was an obvious reference to Bobbie’s burgeoning relationship with Tony.

Bobbie wondered exactly what Tony was telling Allie about their relationship in his private correspondence which was not subject to surveillance by the DoC. Did he share intimate details about what they did? Did he tell Allie about he really felt about Bobbie? She and Tony talked about Allie sometimes and Tony said that he was happy that Allie had found her true self and found herself a man who loved her. He said he wanted the same thing for Bobbie when she was released but Bobbie steered the conversation away from the subject. When Robert Valentine was released Bobbie would vanish forever. There would be no need for her. Would there?

What made things confusing was that Robert was slowly being subsumed by Bobbie. Robert spent little time in the consciousness of their shared body. He didn’t want to because Robert was unhappy. Things were not going well for him with his family and Bobbie coped better with her life than Robert did with his.

The inevitable happened and Mandy finally told Robert that she was having an affair, but that it was more than that. She had fallen in love with her divorcee Dale Shrivington and out of love with Robert. Robert agreed to a divorce and had no hard feelings about it.

Charlotte had moved in with her boyfriend and there were rumblings of marriage. Robert thought that Charlotte was too young for marriage and told her that he thought she was throwing away her future which had resulted in a bitter email exchange which ended up with Charlotte ghosting him.

Mandy made a final visitation to Brentwood where she told Robert that she and Charlotte had decided that it was best if they moved on with their lives without Robert. He had been out of their lives for so long now that they found his presence a distraction preventing them both from living their lives to the full.

“I don’t know what’s going on with you Robert but you have changed. It’s not just being in prison, you are seldom in the room when I visit,” Mandy whispered across the table in the visitor’s room.

“What do you mean?” Robert bristled.

“You go somewhere else. It’s like someone else has taken you over. Then you shake your head and you’re back again. Something is going on that I don’t know about and probably don’t want to know about,” Mandy sighed.

Robert silently seethed but he was also concerned. Mandy and Charlotte were still not safe. They were still subject to Tig’s retribution if Bobbie didn’t continue to toe the line and perform her duties in Seg and keep schtum about it.

Mandy slid a sheaf of legal documents across the table. She had placed little tabs where Robert needed to sign the manuscript that would end their marriage. Dale Shrivington was a director in the finance company where Mandy worked and she didn’t need anything from Robert. They would simply walk away from their marriage.

Robert stared at the documents almost unseeingly. Bobbie flew into his consciousness and appraised Mandy. Bobbie wouldn’t be caught dead in the pantsuit that Mandy was wearing. Her low heels might be expensive but they were awful. Mandy had her blonde hair styled differently and it suited her but her makeup wasn’t right and Bobbie knew how to fix it.

Bobbie would never leave her room looking anything like Mandy.

Robert shook his head, forcing Bobbie from his psyche.

“You did it again Robert. Is there something wrong with you?” Mandy asked.

“You give lousy blowjobs,” Robert blurted out.

There was a beat and then they both realised the absurdity of what Robert had just said and they burst out laughing. They stood up and held each other as they laughed and cried, realising that their marriage was over but both relieved that it was. There was no animosity. They had both been traitors to their marriage.

When Robert returned to his dorm he opened the wardrobe and cast his eyes over Bobbie’s clothing and accruements. Robert’s prison uniforms took up a tiny space at the end of the hanging rod and a single drawer. It was reflective of how much space Bobbie was taking up in his consciousness; there was barely any of Robert left.

Robert realised that if he hadn't been sent to prison he would have never have known that there was woman existing deep inside of him. His latent femininity would have been suppressed and he would have lived his life quite happily as a man. But Allie had awakened the sleeping women that had existed deep within him and once she had stirred there was no putting the genie that was Bobbie back in the bottle. Bobbie was now the dominant force in his life.

Robert took a deep breath and surrendered. Bobbie came flooding into Robert’s consciousness and took over completely. Robert’s memories remained but his willpower, his individuality, his pneuma dissipated. Bobbie was where she rightly belonged, totally in control of what had once been their shared body.

That night Bobbie lay in her bed staring at the crack in the ceiling. She was wearing men’s pyjamas and was sans makeup but she tolerated having to present male. Tomorrow she would put on Robert’s prison uniform and go to work in the laundry. She would pretend to be Robert but Robert was gone. There was no need for him any longer.

Michelle Benson - A New Prison Doll Is Born

A little over a year later, Bobbie had stopped counting the months until the day she would be released from prison because it was now only two weeks away. Bobbie had fretted that like Allie, she would have to find someone to replace her as a prison doll but fate intervened.

Michelle Benson was actually Mitchell Benson, a young gay inmate convicted of a string of solicitation offences and sentenced to two years’ incarceration. The judge ruled his time should be served in a minimum security facility and he was sent to Brentwood.

Maurice Shrew took Mitchell under his wing and with Tig’s blessing made an assessment as to whether or not Mitchell would make a good prison doll. It turned out that Mitchell had worked turning tricks as a twink and sometimes as a ‘sissy’ in a Cheshire Bridge Road establishment. Mitchell took little convincing. He looked forward to spending his evenings in the lap of luxury and if he had to present femme and suck a few old guys cocks and bend over when required so what? It wasn’t like he wasn’t doing the same thing outside of prison for less money.

Marilyn coached Michelle for a week. Michelle was already well versed in presenting femme but she needed polishing. In her previous occupation she would ‘sissify’ herself when required but there was a lot more to being a prison doll than just putting on makeup, slipping into ladies clothing and calling her paramour ‘daddy’ while they had sex. Marilyn taught Michelle how to fully immerse herself in her feminine identity.

Bobbie was pretty sure that Maurice Shrew had already seduced Mitchell Benson and made him his jailhouse lover before Tig agreed that Mitchell could replace Bobbie but that was no concern of hers. It made sense to her that they would share that special bond as prison dolls while they serviced the men in E Wing but also as homosexual lovers in D Wing. Tig too was aware of the situation and it actually made his job easier.

Bobbie lay on her bed and stared up at the crack in the ceiling wondering what the future held for her. The end of the crack was finally touching the base of the light fitting. Her release date had been confirmed.

She was wearing pink babydoll pyjamas and her long black hair was no longer worn in a man-bun. Bobbie only put up her hair and wore prison garb outside her room when she was required to present as Robert. Contrary to how things were in what felt like the distant past when Robert dreaded having to transform into Bobbie, the opposite was now true. Bobbie hated having to pretend that she was Robert.

She was both relieved and terrified. What would she do when she was released from prison? She couldn’t go back to living at Robert Valentine, he no longer existed but the problem was that Bobbie didn’t exist outside of Brentwood either, at least not legally. Bobbie almost regretted having to leave Brentwood but she couldn’t stay. As much as Bobbie adored spending time with Tony Siceresso she was still a prison doll and there were four other men in Seg that she was required to service.

As much as she become accustomed to providing sexual services to the other four crime bosses, and yes she would admit it, she often enjoyed the sex, she was a concubine, a whore, a slattern but Bobbie wanted more than that. She wondered what it would be like living full-time as a woman outside the prison. Would it even be possible?

Could Bobbie Valentine exist outside of Brentwood? Bobbie seriously hoped so because Robert was long gone. Bobbie recalled the arc of her existence. At first the forced feminisation, subjugation and conditioning, then acceptance of her fate, and finally the realisation that she had found her true identity. It had changed her from what she once was to what she believed was her essential self.

Bobbie had disclosed her desire to transform and live as a woman to Allie and Allie was at first sceptical but in their email and their telephone conversations Allie became convinced that Bobbie was genuinely gender dysphoric. She also believed that Bobbie’s gender identity had been suppressed so effectively that had Bobbie not been forced to become a prison doll, Robert Valentine would have lived his life without ever knowing about the woman that existed deep in his psyche.

Allie at first felt remorseful. She and Tig had compelled the meek, weak-willed embezzler into a life of forced feminisation but Allie also realised that in a way she was responsible for Bobbie finding her true spirit.

This must be true otherwise surely Robert Valentine would be eagerly anticipating and yearning to shed the identity of Bobbie and put behind him the years of feminine submission. Robert would be looking forward to reclaiming and repossessing his lost masculinity.

But as far as Allie could determine Robert Valentine no longer existed. Bobbie had shed Robert like a snake sheds its skin.

Bobbie’s Gotta Go

While Bobbie lay in bed considering what her life would be like once she left Brentwood the five Siceresso crime bosses and Tig Hansen were crowded into the office in Seg.

“Bobbie’s gotta go. Not while she’s in Brentwood of course but as soon as she’s out,” Sal growled around the cigar in his mouth.

“Why? We left Allie alone when she was released,” Tony asked.

“Allie was different. Tig didn’t pressure her. She became a prison doll of her own free will. She still works for us for fuck sake Tony. You know that. She manages the Dream Palace, which you own,” Sal turned to face his younger brother.

“But Bobbie? We don’t know how she really feels about all this. She might resent everything that happened to her in Brentwood. She might have a whatchamacallit… a crisis of conscience and blab when she gets out. She might go to the fuckin’ FBI… she might go to the press,” Joey put in his two cents.

“Bobbie has promised me personally that she won’t blab. She just wants to get on with her life and forget all about Brentwood,” Tony pleaded Bobbie’s case.

“Tig, you still got eyes on Bobbie’s wife and daughter right? The same threat that kept her quiet and subservient inside prison still applies when she’s outside, right?” Tony continued.

“Well the wife remarried and the daughter wants nothing to do with him. Bobbie might not give a fuck about the wife but the daughter is innocent so the threat against her is still valid but if Bobbie goes to the Feds they’ll provide security for the wife and daughter and maybe even put them in Witsec. Can you imagine what Bobbie might say if she took the stand?” Tig said to Tony.

“That’s right Tony and it aint just us. A lot of people are going down if we go down. Safer for all of us if Bobbie just disappears. Nobody outside can know about Seg” Sal grunted.

“That’s my final say. Tig, you arrange for Bobbie to disappear as soon as she gets out of Brentwood. I don’t her body to be found or anything that leads the fanook back to us. Bobbie will just be some ex-con who disappeared as soon as they were released. Won’t be the first; won’t be last. That’s all I got to say,” Sal had the final word and the meeting was adjourned.

Sal held Tony back when the others left.

“I aint stupid Tony, I know that you’re sweet on the broad. I don’t get it. She’s a fanook, a femminiello, whatever. You know you can’t save her. Try out the new doll, she aint as pretty as Bobbie but she’s still good looking and she’s younger. Just let Bobbie go,” Sal patted his brother on the shoulder.

“Ok Sal. Bobbie’s gotta go but let me take care of it. Do me this one favour brother,” Tony said; the regret in his voice evident.

“Sure Tony but if you take care of it I need proof that she’s gone. You know what I mean,” Sal reluctantly agreed.

The End Is Near

Bobbie sat nervously outside the warden’s office waiting for her interview. Her hair was down and she was wearing a little eyeliner, mascara and lip-gloss. She was dressed in her prison uniform but she had tapered the pants and shortened the cuffs a little to show her ankles. She liked to think it was a last act of defiance but she knew it was a pathetic gesture.

The use of cosmetics in Brentwood Correctional Facility my male inmates was not specifically banned but cosmetics were not sold in the commissary. Of course the prison dolls acquired everything they needed through Tig who smuggled so much contraband into Seg that it was like having an open door.

Bobbie was well aware that the warden knew what was happening on E Wing. The COs working on D Wing, all employed by Wakefield Services of course, were vetted and paid handsomely to facilitate the farce and to keep schtum.

Still, Marissa Mellowship was a little surprised when Bobbie entered her office presenting femme.

“You know the rules. You only dress openly femme when you are on your way to and from Seg,” the warden said but she said it with some amusement.

“I thought an evening gown would be a little over the top for my exit interview,” Bobbie quipped.

Marissa Mellowship glared at Bobbie. She wasn’t used to being spoken back to by inmates.

Marissa had been handpicked by the Siceressos through their stooges on the board of Wakefield Services to be the warden at Brentwood Correctional Facility. She was corrupt and malleable but she was no dummy. She ran the prison very effectively and maintained tight control over the goings-on in D and E wings. She was the buffer between Wakefield Services and the DoC. Her credentials were impeccable and her performance reviews were outstanding.

The Siceressos, the board of Wakefield Services, several high ranking politicians and officials in the DoC and the justice system relied on Marissa’s acumen and discretion. Marissa knew the consequences if word was ever to get out about how the heads of a crime family managed to live in the lap of luxury, sequestered from the dross of prison life while they were incarcerated in Brentwood.

Marissa was in her fifties and was wearing a navy-blue tailored skirt-suit, nylons and heels; her hair was coiffed and her makeup perfect. She looked like a business executive. She was attractive but she had what was colloquially known as a resting-bitch-face. In summary she looked like a woman who was not to be fucked with.

“Sit,” Marissa pointed to the chair in front of her desk.

“Robert Edward Valentine, sentenced to seven years’ incarceration having been found guilty of fraud, insider trading and embezzlement,” Marissa read from a file laid out in front of her.

“Served eighteen months in Smith State Prison then transferred to Brentwood Correctional Facility to complete his sentence and is now eligible for probationary release,” Marissa looked up from the document.

“What can I say? I’ve been a model prisoner and I have a good lawyer. In fact I learned how to be a model right here in Brentwood,” Bobbie offered a fake smile.

“You’re not free yet Robert so I’d can the sarcasm,” Marissa said through gritted teeth.

“I prefer to be called Bobbie. I’d also like to have it noted on my release documents that I intend to begin gender reassignment on my release,” Bobbie replied.

“Your councillor has made no such notation in your quarterly behavioural counselling reports,” Marissa made a show of skimming through several documents.

“I never told him and I’m pretty sure you know why,” Bobbie offered another fake smile.

“Let’s cut the crap and get this over with. You’ve completed the exit questionnaire and state that you were treated fairly and have been rehabilitated and are ready to re-enter society. You have made no complaints and no infringements have been recorded against you. As you yourself say, you have been a model prisoner,” Marissa continued.

She then went on to ask a series of proforma questions which Bobbie answered without the sarcasm. She was close to being released and Bobbie knew it was in her best interests to behave herself and appear thankful.

“Sign here. You will be processed on Wednesday. Do you have someone picking you up?” Marissa asked.

“Yes ma’am,” Bobbie finally relaxed and smiled genuinely.

But she couldn’t help one last quip.

“Those shoes don’t go with that suit. I’d have gone with the black pumps instead of the sandals,” Bobbie smirked back at Marissa from the door.

A corrections officer was waiting outside to take Bobbie back to D Wing.

As soon as Bobbie left her office Marissa Mellowship snatched up her phone and pressed a button that connected her to the Siceressos office in E Wing.

“She’s got a mouth on her. I think she’s going to be trouble,” Marissa said sternly.

“Don’t worry about it. She’s going away,” Sal grunted into the phone.

Marissa put down the handset and smiled evilly. She took the page from the file where Bobbie had insisted that the warden note down Bobbie’s intent to transition and fed it into the shredder.

“Smartass bitch,” she hissed.

But she knew that Bobbie was right about her shoes.

One Last Night

Sal made the same speech he had made the night he had welcomed Bobbie to Seg and farewelled Allie Katt except this time he was welcoming Michelle Benson and farewelling Bobbie Valentine. Sal took Michelle to his room to exert his right of ‘jus primae noctis’, Latin for the right of a feudal lord to deflower any virgin he desired.

Mike Giacomo and Petey Gruffalo waited their turn knowing that Sal wouldn’t be long with Michelle. They wanted to try out the new prison doll. Joey Malzone took Marilyn Shrew to his room. Tony Siceresso had already declared his intent to have Bobbie Valentine all to himself and no one had objected. As soon as he and Bobbie were safely locked in his room Tony undressed and stood naked before the woman he adored.

Tony kissed Bobbie softly, holding her close, feeling something he couldn’t quite explain. Bobbie had become part of his life. He looked forward to seeing her every day and was jealous when she went with the other guys in Seg. He was heartbroken that he had to be the instrument of her demise but he couldn’t leave it to Tig. Who knew what Tig’s henchmen were liable to do to Bobbie?

“I want tonight to be special Bobbie,” he whispered in her ear.

“Me too Tony. This will be our last night together,” Bobbie replied not knowing the implication of what she was saying; unaware of the fate that awaited her.

Bobbie had scoured her wardrobe, wanting Tony to remember her looking her best. She wore a red satin evening gown, split to the waist to show off her long legs clad in sheer holdup stockings and was shod in red Louboutin high heels.

As their lips touched Tony's hand went to her thigh and he stroked her skin delighting in the feel of her gossamer nylons on his fingertips. His fingers slowly climbed up her leg until he came to her tight red satin panties. Bobbie hadn't tucked. She knew that she would be spending the night with Tony and unlike the others Tony liked to touch her there.

She pressed herself against Tony’s hard body, her fingers seeking out his mighty appendage and finding it hard. She stroked him to full tumescence while Tony massaged Bobbie’s cock through her panties, sliding the satiny fabric up and down her shaft until she groaned into his mouth.

They both felt the need. They knew that they would while away the evening in Tony’s big bed making love, being tender with each other, expressing the adoration they felt for each other on their last night together. But right now their passions were raw. They wanted to slake the lust they had for each other quickly so they could enjoy the gentle lovemaking that was to follow.

Bobbie bit Tony on the earlobe and he hissed and squeezed her cock tightly in response and Bobbie clutched Tony’s cock tightly, extruding a droplet of pre-ejaculate that she massaged into his veiny rod.

“Fuck me! Fuck me now!” Bobbie gasped into Tony’s ear and bit his earlobe again.

Tony kissed her passionately, biting her lip, thrusting his tongue into her mouth, mouth-fucking her with his tongue.

Tony spun Bobbie around and slammed her into the wall and she gasped. She wanted him inside her so bad. Tony gathered the drape of her gown and raked it up her back, exposing her bountiful buttocks clad in the shiny red panties. He kicked her feet apart, forcing her against the wall with his weight, his cock pressing into her natal cleft.

“Fuck me Tony. Cum in me. Make me yours,” Bobbie groaned.

She seldom behaved like a slattern with Tony, their lovemaking was always passionate but usually gentle and prolonged but right now Bobbie wanted Tony to use her, to take her like a whore, to fuck her.

Tony pulled Bobbie’s panties halfway down her thighs and pressed his cock into her puckered bud.

“Do it!” Bobbie moaned.

Tony pushed the full length of his turgid phallus inside Bobbie’s tight anus, her sphincter stretching to accommodate him, the lubricant easing his passage, her rectum enveloping his steely organ, squeezing it. Tony let go of Bobbie’s dress and gripped her hips and began to fuck her.

“Oh god yes,” Bobbie cried.

She pressed her palms flat against the wall, her face inches from the surface as Tony began to fuck her violently. She pushed back against him wanting every millimetre of his manhood inside her pressing on her prostate and lighting up her sphincter. She felt subservient and salacious. His cock was hurting her but hurting her in ways she relished. She felt like a wanton harlot and she was enjoying every second of it as Tony thrust his cock in and out of her tight passage, his pubis slamming into her buttocks, making them quiver.

Tony looked down and watched his cock slam in and out of Bobbie’s clenched ass. He was so excited that he felt his orgasm blooming and he sensed that Bobbie was close too. She was pushing her ass out, inviting him to pillage her snug pink crevice.

He reached around and found Bobbie’s cock achingly hard, dripping a continuous stream of precum. He gripped it and stroked it as he pummelled her back passage, feeling it judder in his fingers as her issue roiled in her scrotum ready to explode.

“Yesss!” Tony hissed as he slammed his manhood all the way inside Bobbie’s tight anus and ground against her buttocks flooding her with his seed.

“Oh god!” Bobbie wailed as her cock juddered and her emissions erupted.

Bobbie’s hot musky semen burst forth, spattering against the wall as Tony yanked on her quivering tool, draining her. His cock was rock hard inside her, juddering as his spend filled her and dribbled out of her tight opening, running down her thighs, soaking into her stocking tops.

Bobbie turned her head sideways as far as she could and Tony crushed his lips against hers as the last of his issue drained from his cock buried deep in her rectum. Bobbie mewled and returned the kiss as Tony squeezed the last droplets of cum from her quivering cock.

They stayed like that. Bobbie pressed against the wall with Tony’s cock buried in her ass, Bobbie’s spunk dribbling down the wall, her cock slowly deflating in Tony’s hand, Tony’s semen running down her thighs, dampening her stockings, kissing each other deeply.

Then Tony ripped his cock from Bobbie’s battered anus and spun her around. He kissed her once and then he picked her up and carried her to the bed where they made love tenderly and lovingly into the early hours.

They lay in bed exhausted, smoking, sipping the drinks that Tony had made for them. Bobbie curled up close to Tony so she could feel the warmth of his body one last time.

“I’ve got a going away present for you,” Tony whispered.

“Good, I like presents,” Bobbie smiled and Tony felt his heart flutter.

Farewell Bobbie

On the day of her release Bobbie had packed everything she needed into one suitcase. Most of her clothes were still hanging in the wardrobe. They wouldn’t fit Michelle but they might fit Marilyn. To be honest Bobbie didn’t give a fuck what Tig did with them, she had packed enough clothing to get her through the first few days of freedom and then she could buy her own. She left the wigs, most of the fuck-me shoes and the large cosmetic case behind, packing only the cosmetics she needed into a small makeup case.

The civilian clothing she had worn to prison and the cheap suit that the DoC had provided for her to wear on her first day of freedom lay untouched on the bed.

She was wearing black spandex leggings, a pristine white loose fitting blouse, black high-heels, full makeup with her hair in a pony. She wore prosthetic breastforms in the cups of her brassiere to give her some shape but the rest was all Bobbie. Bobbie had entered the prison as Robert but she was leaving under her own terms as Bobbie despite the fact that legally she was still Robert Edward Valentine. She would start working on that as soon as she settled down.

Bobbie took one last look at the crack in the ceiling and smiled. She wheeled her suitcase down the passageway towards the exit to D Wing where two corrections officers were waiting to process her out of Brentwood. It was the middle of the afternoon and the wing was otherwise deserted, not that there was anyone she needed to say goodbye to, not even Marilyn or Michelle.

“Really?” one of the corrections said when he saw how Bobbie was dressed.

“Who gives a fuck! Let’s just get him processed and out of here,” the other corrections officer deliberately misgendered Bobbie who didn’t give a damn.

Freedom and a new life awaited her.

Processing didn’t take long at all and when a corrections officer finally led Bobbie to the pedestrian entrance to Brentwood Correctional Facility and opened the door she stepped outside and didn’t look back.

It was a bright sunny day, if a little cool, and Bobbie took in a lungful of sweet country air.

Across the road in the parking lot a black town car was parked. Allie Katt dressed tight denim jeans, a black t-shirt and a tan suede ladies Carhartt jacket leaned against the hood smoking a cigarette. She smiled and waved at Bobbie who smiled back.

Bobbie pushed the wheeled suitcase towards the town car and her smile widened as she got closer. Allie was playing it cool but she was smiling too.

When Bobbie was six feet from the car the driver’s side door opened and a man dressed in chauffeur’s livery exited the vehicle and came around the rear of the vehicle and popped the trunk.

He took a pistol out of the trunk and shot Bobbie three times in the chest.

The pain was excruciating but it only lasted a millisecond before Bobbie was engulfed in a silent, black, endless void. Three crimson florets bloomed on her pristine white blouse like red roses dropped on fresh snow. She fell to the pavement and the chauffer and Allie lifted her body into the trunk and slammed it closed. The chauffer threw Bobbie’s suitcase onto the back seat and he and Allie climbed into the car. The chauffer drove out of the parking lot at a leisurely pace.

Bobbie’s assassination had taken less than thirty seconds.

Prison Dolls - Chapter 4

Author: 

  • Michele Nylons

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • Final Chapter

Genre: 

  • Transformations

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Bad Boy to Good Girl
  • Crime / Punishment
  • Fresh Start

TG Elements: 

  • Breasts / Breast Implants
  • Identity Theft
  • Performer/Entertainer
  • Shopping

Permission: 

  • Posted by author(s)
Prison Dolls  Edited.jpg

Chapter Four - Consequences

Two corrections officers arriving early for the evening shift were leaning against their car parked in the Brentwood Correctional Facility car park smoking cigarettes. They stood there slack jawed while Bobbie was murdered right in front of them.

They regained their composure and one of them reached for his cellphone. The other CO snatched it out of his hand before he could dial 911.

“No! We go inside and tell the warden. Keep your trap shut. You tell no one,” the CO growled at his compatriot.

Later in Seg the Siceressos and Tig had gathered together and everyone was tense.

“What the fuck Tony, you had her taken down right outside the prison,” Sal Siceresso was livid.

“I knew you didn’t trust me to get the job done so I arranged to have it done in front of witnesses who I knew would report back to you through the warden. You said you wanted confirmation that it had been done,” Tony shrugged.

He turned to Tig.

“Isn’t that right Tig? Sal didn’t trust me,” Tony glared at him.

“Well yeah. I’ve called my connections in Miami and cancelled the hit that I had arranged. Bobbie is gone now and that’s all that matters,” Tig replied sheepishly.

“Yeah but you used the word witnesses,” Sal snarled.

“Two COs on the take. The warden had them mop up the blood and dispose of the shell casings so they’re now accessories to murder. They aint saying anything to anyone,” Tony shrugged a second time.

The five crime bosses and Tig were seated in the office in Seg where Sal had ordered Bobbie’s execution only a few days earlier.

“Ok. What’s done is done. Now let’s get down to business,” Sal opened a ledger in front of him.

At that moment the security door to E Wing was blown off its hinges and five Federal agents accompanied by five members of the GBI in full tactical gear entered Seg.

“FBI! FBI! Everybody get down on the ground!” the armed men called as they made their dynamic entry.

The SWAT team had been briefed that there were no weapons on the premises but they were taking no chances. Within minutes of breaking down the door the five crime bosses and Tig were handcuffed and led outside into waiting armoured transport vehicles.

At same the time as the raid on E Wing was underway two GBI Agents entered Warden Marissa Mellowship’s office and placed her under arrest. A specialist search team and CSI operatives entered the prison once it had been secured.

*****

Allie Katt had the TV tuned to WFTV Channel 9, a television station affiliated with ABC in Orlando Florida. She was watching Martha Sugalski present a breaking news story:

‘In a combined GBI and FBI operation five members of the Siceresso crime family, the Warden, several co-conspirators including several corrections officers were arrested at a Georgia minimum security correctional facility yesterday. Other state officials are under investigation in what has been described as a conspiracy of monumental proportions.’

‘The five gangsters were living in what has been described as a private prison block that would rival Pablo Escobar’s La Catedral for its opulence. The crime bosses were living in luxury and continued to maintain complete control of their criminal empire while they were imprisoned in the Brentwood Correctional Facility.’

‘The Solicitor General has been stood down following claims of incompetence during the original trial of the crime bosses while the FBI and GBI continue to investigate alleged State and Federal crimes.’

‘In other news…’ Allie Katt used the remote to turn off the television.

“Why do female news presenters always gotta have blonde hair, big tits and blowjob lips?” Allie asked rhetorically.

“So men will watch the news as well as sports,” Randy Middleton replied flippantly.

Randy was currently Allie Katt’s paramour and had driven the limousine to Brentwood Correctional Facility and fired the three rounds into Bobbie Valentine’s chest.

“Are you still sore babe?” Allie turned to Bobbie Valentine who was curled up on the sofa wearing a pair of yoga pants and a loose-fitting blouse that Allie had loaned her, reinforced nylon footlets disclosed that she wearing pantyhose under the leggings.

“Those fucking blood squibs hurt like a motherfucker when they went off,” Bobbie rubbed her chest through her blouse.

The three pyrotechnical devices and fake blood packets had been secreted in Bobbie’s breast prosthesis and were activated by a remote signal when Randy Middleton fired the three blank rounds at Bobbie’s upper body. At the same time Bobbie had activated an auto injection device sending a measured dose of propofol into her bloodstream invoking immediate unconsciousness. This was the present that Tony Siceresso had surprised her with that last night in Seg.

The shooting needed to look as realistic as possible and no chances were taken.

After the town car left the correctional facility it was driven to a parking station fifteen miles from Bentwood and Allie and Randy Middleton had carefully lifted Bobbie from the trunk and tended to her until she regained consciousness. Allie and Bobbie had transferred to Allie’s BMW and driven to Orlando where Allie had a suite booked at the Waldorf Astoria. Randy had ditched the town car at a chop shop in North Orange and taken an Uber to the hotel.

Bobbie had showered and gone straight to bed and slept for ten solid hours and awakened refreshed and joined Allie and Randy for a room service breakfast while Allie channel-surfed, looking for a news story about Brentwood.

The plan was to hole up in the hotel room until the FBI and GBI raided Brentwood Correctional Facility and took the Siceressos and Tig into custody and imprisoned them in a Federal maximum security facility until their trial.

“We can leave for Miami tomorrow,” Allie came over and sat down next to Bobbie.

She cuddled Bobbie and kissed her cheek.

“I can’t believe that you're out and free,” Allie played with Bobbie’s hair as if she was a little girl rather than a woman in her mid-thirties.

Bobbie seemed petulant. The euphoria she felt after being released and then the mock shooting in the prison parking lot had worn off and Bobbie was now faced with the reality of an uncertain future.

“Honey, can you go down to the convenience store and get me some cigarettes?” Allie asked Randy.

Randy’s brow furrowed and he gave Allie a look of displeasure.

“I thought you were quitting?” he whined.

“Ok, let me put it this way. Can you get the fuck out the hotel room for an hour or two, so I can talk to my friend in private? Go to the bar and have a drink. Maybe sit by the pool and check out the girls in their bikinis. Look, don’t touch,” Allie sidled up to Randy and kissed his cheek and squeezed his ass.

Randy had a fine ass. He was late-twenties, six-two with sun-bleached longish hair, a lean tanned body and incredibly handsome. He was also devoted to Alicia Kettering which was now Allie’s legal name.

“Ok babe,” Randy kissed Allie and snatched up his man-bag.

Randy was the kind of guy who no one was going to tease for carrying a man-bag.

He left the room and Bobbie could sense his reluctance to do so.

“You have him well trained,” Bobbie sniped.

“He’s smarter than he looks and he takes care of me. I know that at the club they call him my toy boy behind my back but I don’t care. He’s useful in all sorts of ways,” Allie grinned and sat back down next to Bobbie.

“I’ll bet he is,” Bobbie carped.

“Are you pissed at me honey?” Allie asked, stroking Bobbie’s arm.

“Why should I be pissed at you? You selected me and gave my name to Tig Hansen who blackmailed me and threatened to have my wife and daughter raped, tortured and killed if I didn’t become a prison doll,” Bobbie said bitterly.

“Then you turned me into a transvestite whore to take your place servicing those thugs in Seg,” Bobbie said through gritted teeth.

Allie alighted from the sofa and made her way over to the kitchenette and poured herself a double Jack Daniel's. She kept her back turned to Bobbie and swallowed the drink and poured herself another.

Tears were streaming down her face but she refused let Bobbie see her cry.

Then Allie felt Bobbie’s arms circle her and Bobbie rested her head on Allie’s shoulder.

“I'm sorry for being a bitch. The truth is you rescued me. I found my true self in Brentwood. I’m scared and I’m lonely and I don’t know what the future holds. You saved my life twice. Once when you released Bobbie from being trapped inside Robert Valentine and the second time when you staged my murder,” Bobbie whispered.

Allie turned around and Bobbie saw the streaks of mascara running down her cheeks.

“Stop crying, you look like a panda,” Bobbie leaned in and kissed Allie on the cheek.

Allie gave a snuffled giggle at the panda joke and Bobbie took tissues out of a box on the counter and dabbed them on Allie’s cheeks.

“I’m sorry Bobbie. I've felt guilty about it ever since I was released from Bentwood,” Allie dried her eyes with more tissues.

“You gave me to the Siceressos but you saved me from them too,” Bobbie poured herself a drink and another for Allie.

“Tony saved you. He had me assemble the prosthetics and the caverject and he had them smuggled into Brentwood without Tig knowing at great risk to himself. He planned the whole thing. I was just his conduit,” Allie took a swallow of her drink.

“Tony loves you,” Allie whispered.

“Love? Don’t make me laugh. How could he love me? I was a prison prostitute with whom he had an infatuation. I was convenient. A pretty girl with a dick that he fucked because there were no women,” Bobbie barked.

Bobbie was shocked when Allie slapped her face.

“Don’t you talk about yourself like that. You know that’s not true. You know that’s not who you are and you know that’s not how Tony sees you,” Allie gently stroked the red mark on Bobbie’s cheek where she had slapped her.

“Tony gave up everything for you. He’s the one who contacted the FBI and brokered a state’s evidence deal. Tony sold out his brother and the others because they wanted to kill you,” Allie continued.

“Do you know where he is?” Bobbie asked, knowing that Allie and Tony had been communicating extensively just prior to Bobbie’s release.

“He’s in protective custody somewhere, held incommunicado until after the trial. He’ll have to testify and then the FBI will put him in Witsec. Didn’t he explain all this to you?” Allie asked.

“He told me that they intended to kill me to keep me quiet. Of course he explained the plan you and he had hatched to fake my murder. He showed me how the prosthesis and caverject worked and how to wear them. He never told me that he was going to become a corroborating witness and turn state’s evidence and bring it all crashing down,” Bobbie admitted.

“He did all that for you,” Allie smiled at Bobbie.

“Do you think? Or was it all a contrivance to get rid of his brothers and the others and get out of prison?” Bobbie was sceptical.

“You can ask him yourself when you see him,” Allie replied, pouring more drinks.

“I’ll never see him again once he goes into Witsec. You know how that works,” Bobbie sighed.

“Look Bobbie. Don’t fret about things over which you have no control. You have a new and exciting life ahead of you. You’re coming to live with me and we have a lot to do,” Allie took Bobbie’s hand and picked up the bottle of JD and led them back to the couch.

“We need to organise your surgeries, you can’t go around looking as good as you do without any tits,” Allie laughed and poked a finger into Bobbie’s flat chest.

“A nip here, a tuck there and you will be the woman you always dreamed you could be,” Allie smirked.

“Then we need to get you some identity documents. Using Tony’s contacts we already have a birth certificate for you. Your new name is Barbara Southland. You can still go by Bobbie of course,” Allie patted Bobbie’s hand reassuringly.

“Who is the real Barbara Southland?” Bobbie asked.

“She was born around the same time as you in Cedar Key Florida. Poor kid only lasted a few days. If you want to get all sentimental about it you can imagine that she now has a life through you,” Allie tried her best to steer the subject away from being morose.

“You can’t change Robert Valentine’s name and gender by deed poll or apply for a gender recognition certificate using Robert’s identity for obvious reasons. As far the justice department is concerned Robert Valentine has violated probation and is a fugitive,” Allie explained.

“Good. Robert Valentine no longer exists. I’m Barbara Southland but you can call me Bobbie,” Bobbie giggled.

The alcohol was starting to take effect.

“Well I’m pleased to meet you Barbara,” Allie giggled too.

“I’m sorry I was such a cunt earlier,” Bobbie said.

She leaned in and was about to kiss Allie’s cheek but Allie turned to say something and the kiss caught the side of Allie’s mouth.

They both froze. The kiss was an accident but they both felt the spark. They both knew that they could just brush it off and leave it there, an awkward moment soon forgotten.

But they didn’t.

Whether it was the left over adrenaline from Bobbie’s escape or the day-drinking, their inhibitions were down.

Allie turned to Bobbie so that next kiss landed full on her mouth. The kiss was long and languid and the two women caressed each other tenderly. Then the kiss became impassioned and they used their tongues. Bobbie eased Allie down on the sofa and lay on top of her. Allie’s body felt familiar, but different somehow. Bobbie used her hands to find out why and then she found Allie’s breasts.

They were full and perky and had a heft to them that no prosthetic could imitate. Bobbie unbuttoned Allie’s blouse and slipped her hand inside and slipped the perfect globes from the cups of Allie’s brassiere. The flesh was soft and resilient and her nipples were engorged. Bobbie broke their kiss and lowered her face to the magnificent orbs. She circled the dark pink areolas with the tip of tongue and Allie put her hands on Bobbie’s head and guided her mouth from one breast to the other.

Bobbie flicked Allie’s nipples with her tongue and then nipped them gently with her teeth and Bobbie heard Allie gasp and Bobbie smiled. Allie slid her hands inside Bobbie’s loose-fitting blouse and traced her fingers across Bobbie’s flat abdomen then up to her chest and found Bobbie’s tiny breasts and she stroked them and found Bobbie’s nipples were also engorged.

Bobbie wished she had real breasts just like Allie’s but she didn’t articulate it. They both knew that if either of them spoke the spell would be broken and neither of them wanted that. Bobbie craved the comfort of someone who wasn’t just using her, of someone who genuinely loved her. Tony was far away and unattainable but it wasn’t just that. She and Allie had a special bond. Their time together had been brief and most of the time it had been adversarial but she recalled the time they had fellated each other in Allie’s dorm.

Bobbie recalled how she had surrendered. She recalled their first kiss. Their lips pressed together only lightly at first, enjoying the delicate sensuality of it, tasting Allie’s lipstick, inhaling her perfume, feeling her feminine curves pressed against Bobbie’s satin-shrouded body. The rustle of satin and lace, the hiss of a skirt skimming over nylons, the sensation of a thickening cock pressing against glossy panties.

Bobbie remembered Allie’s parting words to her: ‘The lady doth protest too much, methinks’.

Bobbie suckled Allie’s breasts and Allie stroked and tweaked Bobbie’s nipples. A warm tingle of delight spread from both of their bosoms and their breathing became heavy. Bobbie returned her mouth to Allie’s and their kisses became impassioned.

Bobbie lay on top of Allie and Allie’s legs were spread. Bobbie took advantage of the situation and slid a hand under Allie’s skirt. Allie hissed when Bobbie snaked her fingers across Allie’s thighs, her fingertips gently grazed across Allie’s pantyhosed-skin.

Allie reciprocated stroking Bobbie’s buttocks and legs clad in her tight, gauzy yoga pants. Their kisses became more impassioned and Bobbie found Allie’s penis tenting her panties. She could feel the precum oozing into the translucent fabric and she circled Allie’s glans with her fingertip and felt Allie shudder underneath her.

Allie’s hands sought out Bobbie’s crotch. Bobbie had tucked but not taped. Her pantyhose and Yoga pants kept her penis and scrotum concealed along her perineum, tucked tightly between her legs, but now Bobbie’s cock was swelling and Allie could feel the girth of it through the layers of spandex and nylon. She stroked Bobbie’s thickening appendage and Bobbie squirmed and drove her tongue deeper into Allie’s mouth.

Allie pushed her hand inside the waistband of Bobbie’s yoga pants, the elastic stretching on Allie’s forearm as she struggled to free Bobbie’s burgeoning erection. When she finally had hold of Bobbie’s cock through her pantyhose she freed it and laid it flat against her lower belly. She removed her hand from the tights and placed both of her hands on Bobbie’s ass and began to buck.

Bobbie pressed her hard cock against Allie’s, their cocks pushed together through the layers of Bobbie’s yoga pants and pantyhose and Allie’s nylon rayon panties and pantyhose. Allie lifted her legs and wrapped them around Bobbie and the girls began to hump each other.

They mutually and simultaneously stimulated each other’s genitals, the pleasurable friction against their penile shafts enhanced by the layers of diaphanous fabric. Shards of sexual delight radiated from their respective pulsing penises. They clung to each other and rutted, kissing frenetically, holding each other tight as the rubbed their crotches together.

Allie’s panties were soaked with pre-ejaculate as was the front of Bobbie’s yoga pants. They moaned into each other’s mouths as they clung to each other, pressing their cocks against each other’s, circling, gyrating and rutting. Allie tightened her legs around Bobbie’s body and thrust upward as her creamy load expressed from her trapped organ. The intensity of the delicious feelings radiating from her crotch was indescribably wonderful.

Bobbie felt Allie’s warm, slick glutinous secretions soak into her tights and she ejaculated in turn. Their two cocks were pressed tightly, juddering and pulsing as the two gorgeous women ejaculated on each other. They were both overcome with the intensity of it. They held each other tight, kissing, grinding and mewing into each other mouths as they spent themselves.

“Well that was a surprise,” Allie still had her legs wrapped around Bobbie’s waist but the frantic thrusting and ceased.

The warm, slippery wetness in their crotches felt oddly pleasant and the piquant musk of semen filled the air.

“Allie brushed Bobbie’s bangs out of her emerald green eyes and she smiled up at her and kissed her softly.

Bobbie gazed down into Allie’s big blue eyes and smiled.

“It just happened,” Bobbie blushed.

“I think it’s something we both needed,” Allie replied.

Bobbie nodded and rested her head on Allie’s shoulder seeking comfort after their frenzied frottage.

Allie wrapped her arms around Bobbie and held her close.

“I think we better get cleaned up before Randy returns from his errand,” Allie smiled and struggled to extract herself from underneath Bobbie.

Bobbie climbed off the couch, careful not to let any of the semen clinging to the front of her yoga pants drip onto the fabric. They each padded away to their respective bedrooms and cleaned up in the ensuite bathrooms. Allie changed her pantyhose and panties, mercifully her skirt had survived the tryst unscathed so she could still wear it. It might look suspicious if both she and Bobbie had both changed when Randy returned. She freshened her makeup and padded into Bobbie’s room.

Bobbie had also changed her pantyhose. She hadn't been wearing panties but her yoga pants were in no fit state to wear. Allie saw that Bobbie had rinsed out the tights and they were hanging from the pull-out clothes line over the bath. Bobbie was seated in front of the vanity fixing her makeup. She had changed into a red leather skirt and a black lace-topped tank-top.

Allie approached Bobbie and stood behind her, watching Bobbie finish her makeup and brush out her long black hair.

“Some people only change on the outside. But you’ve also changed on the inside. You gotta go through a special kind of hell or a special kind of love to change who you are on the inside,” Allie said.

“You’ve gone through both. Don’t ever forget that you are special,” Allie leaned down and kissed the top of Bobbie’s head and walked away.

Bobbie’s emotions were in turmoil but she felt better. She felt validated and she felt free. She heard the murmur of voices coming from the suite indicating that Randy had returned. Bobbie came out to join them.

“You look nice,” he commented noticing Bobbie’s change of clothes.

If Randy suspected anything he didn’t say anything.

“Bobbie and I are going out on the balcony to smoke and then we’re going shopping,” Allie snatched up the cigarettes that Randy had placed on the kitchenette counter.

“Yes ma’am. At your service. I’ll drive but I’ll wait in the car while you shop if you don’t mind,” Randy grinned.

“You normally like helping me pick out my lingerie,” Allie teased and Randy blushed.

“I’ll leave you girls to it and listen to a podcast,” Randy replied sheepishly.

To say that Bobbie was nervous was to put it mildly. During her time in Brentwood she had learned to walk and speak like a woman and used womanly gestures and mannerisms and she was virtually unclockable but she had never presented herself to the outside world.

Bobbie was excited but terrified. She knew that if she wanted to live her life how she wanted to live it she would need to get over her fear quickly.

“Everyone is looking at me,” Bobbie whispered into Allie’s ear, almost clinging to her as they stood in the middle of the galleria.

“Honey, we are two tall, stunning, beautiful women, with great hair, prefect makeup, tidy figures, great asses and we’re wearing short skirts and heels. The men are leering and the women are jealous. Take a look around,” Allie patted Bobbie’s arm and then unhooked it.

Allie was right. Most of the women their age were wearing track pants, jeans, khakis, shift dresses, very much dull and unfashionable ‘comfortable clothing’. To be fair some of the women were dressed in stylish clothing and they too attracted the roving eyes of the male mall walkers.

Bobbie took a deep breath and tried to relax.

“We need to get you a suitable wardrobe. Most of the clothing you brought from Brentwood is eveningwear and you can’t wear high heels everywhere. My treat,” Allie smiled and held out her black Visa card.

Bobbie had money in Robert Valentines account but she couldn’t touch it. Being a fugitive it was likely that Robert’s bank account was being monitored by law enforcement. Bobbie and Allie assumed that Bobbie’s so called murder had not been reported to the authorities, there was no way the Siceressos or the warden and the COs who had witnessed the crime were going to incriminate themselves. Robert was considered dead and disposed of by the Siceressos and to be a probation absconder by law enforcement.

Bobbie soon forgot about whether or not she was being stared at as she and Allie went on a shopping spree and they returned to the car with two shopping trolleys filled with clothes, shoes and accessories. Randy loaded everything into the trunk and they drove back to the Astoria with Bobbie and Allie chattering away excitedly in the back seat while Randy drove with his airbuds in place listening to his podcast.

With the Siceressos locked up they were free to leave their hotel room and the three of them ate a sumptuous meal in the restaurant then retired early for the four hour drive to Miami the next day. They arrived at the Dream Palace located on Ocean Drive, South Beach in the early afternoon.

As promised, on her release Allie had been rewarded for her services in Seg and had been installed as the host of the drag show at the Dream Palace. To her surprise she found out when she arrived that Tony had reserved one of the two top-floor apartments above the nightclub and restaurant for her. The other apartment was occupied by the manager, a cis woman named Betty Underwood who advised Allie that she was to be her understudy and when Betty was confident she was to handover her managerial duties to Allie.

Allie took some time off to undergo breast augmentation surgery and a tracheal shave and then threw herself into the job understudying Betty and performing in the drag show in the evenings as host. With Tony’s blessing Betty had handed over the managerial position to Allie after eight months and moved back to Atlanta to manage another of the Siceresso’s nightclubs.

“You have done really well for yourself,” Bobbie said as she surveyed Allie’s luxury apartment.

“I have another surprise for you. I terminated the lease on the adjoining apartment and it’s all yours,” Allie smiled at Bobbie who squealed with delight and gave Allie a hug.

Once Bobbie was installed in her apartment there was work to done establishing Barbara Southland’s identity. Bobbie met with one of Tony’s operatives who greased the wheels and accompanied Bobbie to an office of the Department of Highway Safety and Motor Vehicles out of hours where she was photographed and issued a driver’s licence in the name of Barbara Southland using the details on the birth certificate.

She asked the operative who insisted on being called ‘Mr Smith’, if he had heard anything from Tony.

“Tony arranged for this a few months ago and paid up front, all through Allie. I don’t know where he is and I don’t want to know. Take care toots and good luck,” Mr Smith said when he dropped Bobbie back at the Dream Palace.

Bobbie never saw Mr Smith again but now she had a valid birth certificate and driver’s licence. She was in the system and able to apply online for a social security number and then open a bank account. Being an excellent fraudster and embezzler in a previous life Bobbie was able to transfer all of Robert Valentine’s savings into Barbara Southland’s bank account without leaving a trace. With a substantial bank balance she was able to apply for a credit card.

During this period Bobbie checked into a private clinic and had breast augmentation surgery and a tracheal shave. She considered taking hormones but decided that it was something she might decide on later. She had very little body hair and had a series of laser treatments to permanently remove her facial hair. She was happy to just pluck any rogue hairs as they appeared and enjoyed still being able to generate a healthy turgid erection.

“Did you ever consider getting bottom surgery?” Bobbie asked Allie as they sat in the elegantly styled waiting room pending admittance for Bobbie’s breasts augmentation surgery.

“Nope, never did. I’m happy with my body as it is now and the option is always there,” Allie replied.

“Being a transgender woman is a lot of different things to different people. Not all trans women are on hormones and only a small percentage actually have bottom surgery. People can have whatever genitals regardless of their gender,” Allie continued.

“I'm a woman with a dick and I like having a dick. I don't really want a vagina. That doesn't make me less of a woman,” Allie squeezed Bobbie’s hand reassuringly.

This wasn’t the first time they had had this conversation but Allie understood where Bobbie was coming from. It had taken Bobbie quite a while until she was confident enough to go out in public on her own but Allie had watched Bobbie blossom into a beautiful, confident woman.

The only thing Bobbie was missing in her life was a partner and Bobbie pined for Tony Siceresso from whom both Allie and Bobbie had heard nothing. He was still in protective custody, securely squirreled away incommunicado while the Siceresso trial was looming. They had been following the case and it turned out that Warden Marissa Mellowship had made a plea deal and would also be testifying.

Tig Hansen had not been confined in a maximum security facility because he was not considered to be as important as the four crime bosses. He’d been assassinated in the prison shower block and there was speculation as to whether it was by the order of the Siceressos or by a rival crime organisation that was moving into the void left when the Siceressos criminal empire crumbled.

Allie employed Bobbie as the assistant manager at the Dream Palace and with her financial acumen she took over the books and advised Allie how she could make the club more profitable. Bobbie bought a nice car, decorated her apartment and settled into life in Miami and finally felt like the woman she had always wanted to be ever since she had made the decision that had altered her life so drastically. She sometimes wondered about her daughter Charlotte and occasionally about Mandy but never about Robert. After she had stripped his bank account he no longer existed as far as she was concerned.

When the Siceresso trial came to court it was all over the media. Their takeover of Wakefield Services and the building of their ‘La Catedral’ inside of Bentwood Correctional Facility were sensationalised and attracted the most coverage. The inmates in D Wing all claimed ignorance of Seg’s existence and nobody mentioned the ‘prison dolls’. It was in nobody’s interests to do so.

The FBI then presented evidence proving that the Siceressos had maintained control of their criminal empire from inside the prison. Under the RICO act all of their illegal assets had been seized and the crime bosses sold off their legal businesses to pay for their defence. The two key prosecution witnesses, Tony Siceresso and Marissa Mellowship spent days on the stand giving evidence and being grilled by the defence counsellors. Marissa Mellowship also gave up the identities of the key personnel in Wakefield Services who were complicit with the Siceressos and she also coughed up the names of her superiors in the DoC who had manipulated the system to allow the Siceressos to transfer to the minimum security facility.

Investigations were continuing into other government and judicial officials who were believed to be complicit. They were all busy covering their asses and shifting blame.

When the trial was finally over Sal Siceresso, Petey Gruffalo, Joey Malzone, and Mike Giacomo were given a life sentence without the possibility of parole to be served in the federal ‘supermax’ ADX Florence. Marissa Mellowship was put into Witsec waiting to appear in court when the cases against the other conspirators came to trial.

Tony Siceresso was offered the opportunity to join the Witness Protection Program.

All Bobbie new was that the trial was over and she hoped to hear from Tony soon but neither she nor Allie heard a thing. Tony remained incommunicado and they were both wondering if they would ever see Tony again.

Bobbie continued to help Allie manage the Dream Palace but Bobbie was becoming despondent. She wondered if she why Tony hadn't contacted her. Maybe he had entered Witsec full-time and was living far away under another name, making a new life for himself.

She envied Allie’s relationship with Randy Middleton. Randy adored Allie and he was seldom far away from her and Bobbie could tell that Allie loved Randy. Bobbie knew that being jealous was churlish but she ached for Tony. She wanted to feel what it was like to be with a man now that she had completed her transition.

Since the unexpected serendipitous encounter with Allie on the couch in Orlando, Bobbie had been celibate. She and Allie had agreed their two sexual encounters had been gratifying and that they loved each other but that they didn’t love each other in that way and having a sexual relationship as well as a friendship and a business relationship was not prudent.

In the evenings she often frequented the Dream Palace conveniently located below her apartment. It was a popular venue with the lunch and dinner crowd and after dinner it was frequented by gay men who came to see the drag show. A smattering of tourists also came for the show along with rowdy crowds of young women attending bachelorette parties. As much as Bobbie enjoyed the show and the festivities their merriment tended to remind Bobbie that she was missing physical contact.

She started drinking a little too much and one night she was approached by a handsome tourist. He was tall, lean and confident and reminded Bobbie of Tony.

“Hello pretty lady,” the man smiled at her.

His teeth seemed impossibly white on his tanned face. He slipped into the booth beside her uninvited.

It was not the first time Bobbie had been hit on and she usually sent the would be lotharios packing but Bobbie was nursing her fourth double JD of the night and was feeling exceptionally lonely despite the nightclub being crowded to overflowing.

“I’m Dale, down from New York for the long weekend,” he said by way of introduction.

“Hello Dale from New York, I’m Bobbie and this is my club,” Bobbie replied dryly.

“Your club! I’m impressed,” Dale smiled again, not taking the hint.

“Well I’m the assistant manager if you want to get technical,” Bobbie replied, spinning her glass around on the table to indicate her disinterest.

“Can I get you another?” Dale pointed at her glass, empty except for the ice cubes.

“I drink for free Dale. Like I said this is my club,” Bobbie tried to brush him off but she had to admit she admired his tenacity.

“Well why don’t you buy me one then?” Dale hailed a waiter.

In the evening the Dream Palace used gay servers who doubled as go-go dancers in the club. They were all young, fit and handsome and wore tight little shorts and sleeveless shirts worn open. They were very popular with the bachelorette brigade who tipped them handsomely to play up to the budding bride. A server who went by the name of Derek came over to the booth.

“I’ll have what she’s having,” Dale said, laughing at his quip from the film When Harry Met Sally.

“And get the lady one too,” Dale added.

“Is this guy bothering you Ms Southland?” Derek ignored the would-be lothario.

Dale sized up Derek and decided that Derek would likely kick his ass if they got into it. Dale was gym fit but Derek had the muscled tone of a dancer and fighter.

“I’m sorry Bobbie. I’ll leave you in peace,” Dale made to leave the booth but Bobbie reached out and gripped his wrist.

“It’s ok Derek. Get the man his drink and I’ll have another double,” Bobbie smiled at the server.

The servers at the club were very protective of the drag queens and of Allie and Bobbie. When the crowd got rowdy the customers sometimes overstepped the mark and while the drag queens were happy to get tipped for having their pictures taken with drunken bachelorettes and tourists they did not like to be touched. They especially did not like being groped by tranny chasers, unless of course the attraction was reciprocated.

“I’ll be right back with your drinks,” Derek smiled at Bobbie and glared at Dale.

“The staff here look after the performers and look out for each other. Derek probably thinks that you’re hitting on me,” Bobbie explained.

“How do you know I’m not hitting on you?” Dale sidled along the bench and sat closer to Bobbie.

“Oh, I know you are but I’ll be up front with you. You aren’t going to get inside my panties and if you did you would be surprised at what you found,” Bobbie said dryly.

Dale looked confused.

“I’m a transgender woman you idiot,” Bobbie sounded exasperated.

Dale looked even more confused for a second or two and then realisation crossed his face. Derek returned and placed their drinks on the table and left.

“If you use the words tranny, ladyboy, transsexual or shemale you’re going to wear that drink. If you think all trannies are cock hounds you better think again because you’re not getting lucky tonight, at least not with me. If you want to stay and watch the show and chat you’re welcome to do so,” Bobbie used the term tranny with immunity because it had been reappropriated by the trans community.

Dale settled down and watched the show. There were four drag queens performing that night and they did a cabaret act, solo performances and stand-up comedy. After the show the drag queens mingled in the crowd hunting down tips. Dale was mesmerised by the performance but he was also intrigued by Bobbie.

“How can you live in New York and have not seen a drag show or met a transgender woman?” Bobbie asked.

“I live a sheltered existence I guess,” Dale blushed and Bobbie became immediately suspicious.

“So is your wife with you here in Miami or is she back in New York?” Bobbie asked and Dale’s blush deepened.

“I can see the tan line on your finger where you’ve taken off your wedding ring,” Bobbie pointed to Dale’s left hand.

“Ok, you got me. I’m down here on business and I took the opportunity to go clubbing. I didn’t know Dream Girls was a gay nightclub,” Dale admitted.

“That guy over there at the bar, those two in the corner and that guy over there with Contessa Divine sitting in his lap are straight. Contessa’s real name is Steve and he works at a health spa during the day but the guy whose lap she’s sitting on doesn't care. To him she’s a beautiful woman who just happens to have dick,” Bobbie chuckled.

“So he’s what you call a tranny chaser?” Dale scooted even closer to Bobbie.

“Yes Dale. Are you a tranny chaser Dale?” Bobbie looked him square in the eyes.

“I don’t know. All I can say is that I find you very attractive and I’m beguiled by you,” Dale admitted.

He placed his hand on Bobbie’s leg under that table. Bobbie was wearing a sequinned cocktail dress and showing a lot of leg and décolletage. She considered removing Dale’s hand but she was more than a little intoxicated, lonely and amused by this married Lothario. She let him leave his hand there for now.

“Thanks for the compliment Dale but I’m used to being hit on by guys like you,” Bobbie replied.

“But you haven’t moved my hand,” Dale whispered in her ear.

“No I haven’t,” Bobbie dropped her hand in Dale’s crotch and was amused when he squirmed a little.

She decided to play things out and see where they went.

Dale leaned in and tried to kiss her but Bobbie shook him off.

“I don’t want my employees seeing me pick up strange men in my own club,” Bobbie said but she smiled at him and found his semi-hard cock in his pants and gave it a squeeze.

Dale slid his hand under Bobbi’s dress and stroked her thighs.

“I love a woman who wears pantyhose, my wife hardly ever wears them anymore,” Dale whispered.

“I don’t wanna hear about your wife Dale. You're convenient because you're married and from out of town so there are no complications and you’ve caught me drunk and lonely but don’t push it,” Bobbie reprimanded him.

Dale’s response was to drift his fingers further up Bobbie’s thigh and stroke the front of her panties. She saw the look of bewilderment on his face when he found that there was only a satin-shrouded Vee with no discernible lump.

“It’s tucked away you idiot. You saw the drag queens on stage. We have a magical way of making our penises disappear,” she jibed.

“I don’t get it,” Dale stroked her legs and the front panel of her panties, obviously excited because Bobbie could feel his cock harden to her touch.

“I don’t think you are going to get it Dale. I take it you’re not going to invite me back to your hotel room and I’m definitely not taking you up to my room,” Bobbie squeezed his cock to tease him.

He blushed again and looked guilty.

“I’m travelling with business colleagues and if they saw a woman entering or leaving my room I’d be fucked,” Dale admitted.

“Then it looks like you're not going to be fucked Dale,” Bobbie chuckled.

“God I want you so bad,” Dale continued to grope her under the table and Bobbie stroked his hard cock through his pants.

If Bobbie wasn’t so drunk and lonely it would have ended there. Just a bit of playful banter with a stranger but Bobbie was horny and her defences were down.

“Go for a piss Dale and when you leave the restroom turn right instead of left. Make sure no one sees you and go to the first office you come to with the sign ‘business manager’ on the door. I’ll wait for you inside,” Bobbie made her proposition and saw Dale considering the consequences of his actions if he were to take Bobbie up on her offer.

“I’ll wait for ten minutes. If you don’t come in I’ll just go upstairs to bed, no harm done. Your choice,” Bobbie gave Dale’s cock a final squeeze and extricated herself out of the booth, her dress riding up showing off her legs and ass as she did so.

The sight of those firm thighs clad in lustrous hose and her tidy ass swathed in black satin tipped the balance and Dale wondered off to find the john. Bobbie stopped at the bar briefly and said goodnight to the duty manager and popped out the back door as if she was heading up to her room.

Her head was swimming and she knew what she was doing was probably stupid but she was feeling more than a little concupiscent. Allie was out on the town with Randy and wouldn’t be back for hours so it was an opportunity for Bobbie to have a little fun without consequences.

She slipped into her office and closed the door. Her office was dark, the only light coming from the screen of her laptop on the desk. A few minutes later the door opened and Dale slipped inside. He was breathing heavily and very nervous.

“Are you in here?” Dale whispered.

“Over here near the desk,” Bobbie giggled.

What Bobbie was doing was stupid and dangerous and he knew it but it was very naughty and Bobbie was excited.

Dale stumbled around in the dark until he could make out Bobbie’s shape in the gloom. He followed the trail of Dior Poison she had left in her wake and sidled up to her. He was nervous until Bobbie pulled him into her arms and kissed him passionately.

Dale groped Bobbie, squeezing her breasts through her dress as his rained down sloppy kisses on her. He tried to get Bobbie out of her dress but Bobbie stopped him.

“We don’t have time to undress honey we need to be quick,” Bobbie gasped into Dale’s mouth.

Dale had no issue with that and slipped his hands under her dress and grabbed Bobbie’s ass and pulled her close to him and ground his cock against her. Bobbie squeezed her hand between their bodies and unzipped Dale’s pants and found him hot and hard when she freed his cock from his underpants. For a big-talker he had a disappointingly small cock but it was hard and ready and that's all Bobbie wanted right now.

“Over here,” Bobbie led Dale to her desk and dropped to her knees.

She took Dale in her mouth and found his cock pleasantly clean and leaking precum which she licked up with relish. She flicked her tongue along his shaft and circled his glans with the tip of her tongue listening to Dale moaning in the dark. Bobbie was hot too and she freed her cock from between her legs and pulled down her panties and pantyhose so could stroke it to full tumescence.

Bobbie felt like a harlot, kneeing on the carpet in her sparkly cocktail dress fellating a stranger while she stroked her hard cock. She felt Dale’s cock begin to quiver and realised that if she wasn’t careful she was about to get a mouthful of spunk.

Bobbie spat out Dale’s cock and got to her feet. She bent over the desk and wiggled her buttocks invitingly.

“What do I do?” Dale was bemused.

“Get behind me you idiot,” Bobbie was becoming frustrated with this married boob but she was horny and she wanted relief.

Dale slipped in behind her and jabbed his cock between her buttocks. The idiot was pushing his cock into the place where her cunt would be if she had one and Bobbie reached behind and steered his cock to her puckered bud.

“Just push honey,” Bobbie whispered.

Dale gripped Bobbie’s hips and did as he had been instructed. His small appendage slipped inside Bobbie’s anus right up the hilt and Bobbie breathed a sigh of gratification as his pubis slammed into her buttocks and the head of his cock just managed to press on her prostate.

“Oh Jesus!” Dale hissed as Bobbie’s tight sphincter opened and his cock was enveloped by her snug tunnel.

“Oh God!” Dale began to ejaculate almost immediately, holding Bobbie tight against him, driving his cock all the way inside her.

Bobbie pushed back against him and wriggled her buttocks appreciatively while she stroked her throbbing cock viciously, attempting to cum right along with him.

She took Dale’s hand and guided it to her erect penis but as soon as he touched it he whipped his hand away as if he had been bitten. He put it back on Bobbie’s hip and fucked her hard and fast as freshets of hot jism erupted from his juddering organ.

Bobbie felt him hammering away at her asshole and although Dale was far from the best fuck she had ever experienced he was adequate enough and he triggered her orgasm and she spattered her seed on the desk and the carpet.

It was over in a matter of minutes and Dale clung to Bobbie until he was finished cumming and then he whipped his cock out of her anus and stuffed it in his pants. He hurriedly adjusted his clothing saying nothing to Bobbie. Now that he had fucked her wanted nothing to do with her and that suited Bobbie right down to the ground. She felt the same way. She stood with her legs apart, Dale’s spend running out of her ass while Dale beat a hasty retreat.

Bobbie took a handful of tissues off the desktop dispenser and cleaned up. She warily climbed the back stairs to her apartment, ripped off her clothes and fell on the bed and was almost immediately asleep.

The next day she felt guilty and remorseful and she never said a word about the encounter to Allie. She couldn’t keep going like this. She needed to get her life in order.

*****

Bobbie was a creature of habit, conditioned during her training in Brentwood. Every morning she douched before she did her makeup and dressed although she had no intention of having sex. She guessed it was like women in a sexless marriage, or women who had given up dating who still took the pill.

Bobbie had just finished dressing for work and was brushing her hair one morning. It was nearly a year since she had been released from Brentwood. Bobbie liked to dress professionally in her role as assistant manager and was wearing a burgundy skirt-suit, a white satin blouse, tan pantyhose and black high heels.

She was in the bedroom brushing her hair in the vanity mirror when she heard the door to her apartment open and at first she thought it was Allie and was about to chide her for not knocking and then she realised that a man had entered her apartment. He had his back to her and appeared to be looking around the apartment. He was square-shouldered and had thick black hair, an olive complexion and was wearing an expensive looking suit. Not your typical burglar.

Bobbie became alarmed. Her cell phone was in the kitchen so she reached for the handset on her bedside table with the intention of dialling 911 when the man turned around to face her.

Her heart felt like it had stopped beating when she recognised the handsome man who was standing at the doorway grinning at her like cat that had ate the canary.

“You look beautiful,” Tony whispered, his eyes taking in everything about her.

He rushed into the room and took Bobbie in his arms and kissed her so passionately that Bobbie was breathless. When he finally broke the kiss Bobbie took a deep breath and spoke.

“You asshole!” she hissed.

Tony looked stunned.

“What?” he was confused by Bobbie’s reaction.

“I haven’t heard from you for nearly a year and you walk in here like nothing has happened,” Bobbie said indignantly.

“I was in Witsec. I wasn’t allowed to tell anyone where I was or even communicate. Those Feebs were up my ass and until I testified they never really trusted me,” Tony said defensively.

“I never knew if you were coming to see me. When you told me about your brother’s plan to kill me I went along with the ruse you devised to save my life but you never said what would happen to me after I was out,” Bobbie hated the whininess of her voice but she was angry.

“It was best you didn’t know. It was to protect us both. Until they put Sal, Petey, Joey and Mike behind bars permanently we would never be safe,” Tony still held Bobbie in his arms and was enraptured by her beauty.

“I made sure you would be looked after until I was free didn’t I?” Tony gave her his killer smile and Bobbie’s heart began to melt.

Tony didn’t give Bobbie time to answer. He pressed his lips to hers and pulled her tighter against him. Bobbie could feel his need, feel the passion in his kisses, feel the adoration in the way he held her tightly against him, feel the lust in the bulge in his trousers which was pressing into her belly.

Bobbie felt her lust awaken like a sleeping dragon and she pawed at Tony, ripping off his jacket and unbuttoning his shirt while he did the same to her. When Tony opened Bobbie’s blouse and discovered her creamy white bosom he was spellbound. Bobbie’s breasts were rounded, shapely and perky. She had resisted the temptation of having huge implants when she had her surgery; she did not want to look like a ‘shemale’ porn star. Her breasts were perfectly proportioned.

Tony tentatively cupped Bobbie’s breasts and she gasped when he stroked her nipples. It was the first time they had been fondled by anyone but herself and the feeling was wonderful. Her nipples hardened and she felt circlets of pleasure proliferate from her creamy globes. She pushed her hands inside Tony’s shirt raked her nails across his chest, then up to his broad burly shoulders and then she intertwined her fingers behind his neck.

Tony hefted Bobbie's breasts in his hands, amazed at their cushiony softness. He felt her nipples become erect as he teased them. At first he gently circled them with his fingertips, then he thrummed the pliable nubbins and each time he did Bobbie mewed. He began to tweak them and Bobbie purred like kitten into his mouth as their kisses became more impassioned.

The two lovers yearned for each other, foreplay could wait, they both wanted to copulate. Bobbie was becoming uncomfortably erect and she put her hand under her skirt and freed her penis from between her legs. It sprang forward, still confined by her pantyhose and panties but it tented her skirt.

Tony could feel the lump of it pressing into him just as Bobbie could feel Tony's cock pressing into her body. She squeezed Tony’s cock through his trousers and then she fumbled with his zipper and freed the turgid appendage and took it in her hand. Tony sighed and mashed his lips harder against Bobbie’s.

He slipped a hand under her skirt and squeezed Bobbie’s penis through her panties. He could feel that the front of her panties were wet with precum. Bobbie yanked at Tony’s belt and the button on the waistband of his pants and they dropped around his ankles.

Tony hiked up Bobbie’s skirt and pushed her down on the bed, their need had become raw animal lust and they pawed at each other. Bobbie gripped Tony’s throbbing phallus and yanked on it, feeling the constant dribble of precum on her fingers. Tony palmed Bobbie’s erect penis, rubbing her silky panties against the gusset of her sheer-to-the-waist pantyhose encasing her tumescent organ.

He lay on top of her and pressed his cock against hers, humping her through her panties, his hands returned to her breasts and he stroked her nipples until Bobbie screamed silently into his mouth. The feel of Tony’s hard, veiny phallus rubbing on her sensitive cock was overwhelmingly delightful, the satin and nylon eliciting scintillating sparklets of enchantment in them both.

Bobbie lifted her legs, exposing her buttocks, clinging to Tony, offering herself to him, her need a fire in her belly. She guided Tony’s engorged manhood inside her panties and nestled it in the crack of her buttocks. She was ready to be fucked and desperate for Tony to put himself inside her so that she could feel the interconnection that could only be expressed through coitus.

Tony rubbed his glans in the crease of Bobbie’s buttocks, relishing the feel of her silky pantyhose on his bloated appendage. It was like satin-winged butterflies were fluttering against his cock. Bobbie was becoming impatient and she took him in hand and guided the head of his penis into her puckered bud. His cock was leaking a continual torrent of precum and she hoped that it would be enough to ease the passage of his big cock inside her. To be honest she didn’t care. She just wanted to feel Tony’s steely rod stretch her open.

“Push goddammit!” Bobbie lifted her ass higher off the bed and locked her ankles behind Tony’s back.

Tony pushed hard, his cock stretching the gauzy fabric of Bobbie’s pantyhose until it ripped open and his cock slammed into Bobbie’s anus all the way.

Bobbie suppressed a shriek as her tight asshole was rent open by Tony’s huge, hard cock. Tony sensed Bobbie shudder and felt her gasp into his mouth and despite his need he lay still, letting her anus get used to his steely rod. He kissed her gently and stroked her cheek. The feel of her breasts against his chest was comforting and sensual; a new experience but one he was delighted with. His cock was leaking a continuous flow of pre-ejaculate which lubricated Bobbie’s tight channel.

Bobbie had forgotten what it was like to have Tony’s huge penis inside her. Her anus was like a scabbard for his sword. Her anal sheath was where his manhood belonged.

“Now,” Bobbie whispered and dug her heels into his back, encouraging Tony to fuck her.

Tony pressed his lips against Bobbie’s and slipped his tongue inside her mouth as he began to slowly fuck her. He ensured his belly pressed against her hard cock lying flat against her body shrouded in the soft, satiny fabric of her panties and pantyhose. He drove his cock all the way inside her until his scrotum slapped against her taint then he slowly withdrew and did it again.

He forgot how tight and plaint Bobbie's anus was, her rectum squeezed his turgid cock and her sphincter clenched tight around the base of it when he was fully inside her. Bobbie felt gratifyingly full as heavenly waves of carnal pleasure radiated from her anus, her cock was tingling with sublime sensations as Tony pressed his hard belly against it as he thrust in and out of her.

Tony pinned Bobbie to the bed and jackhammered his cock in out of Bobbie’s tight hole as she writhed and mewled underneath him. She bit his lip and raked her nails down his back encouraging him to go harder and faster, she drummed her heels against him, coaxing him.

Tony gripped Bobbie’s shoulders and pounded away at her, kissing her, holding her close, feeling her hard cock against his belly and her anus contracting around his cock, driving him toward climax.

They came together, Tony’s cock fully-engorged and quivering as it spewed forth his issue. His ejaculate flooded Bobbie’s anus and she screamed into his mouth as she came right along him. He felt her scalding emissions burst through the silken trap of her panties and hose and warm his belly, her hot viscous essence smearing his flesh. His cock was so hard that it was almost painful as it juddered deep inside Bobbie’s anus ejaculating stream after stream of hot glutinous semen.

They clung to each other, pressing their bodies together; their lips locked together, their tongues intertwined as they relished the carnality.

When they were finally spent Tony rolled off Bobbie and took off her heels, blouse and skirt while she took off his pants and shirt. When he was naked, Tony pulled Bobbie under the covers, leaving on her panties and pantyhose because he loved the feel of the gossamer garments against his flesh. They began to kiss and stroke at each other tenderly. Their initial need was sated but their desire for each other was still a burning a flame and this time they took their time and made love to each other rather than just fuck.

Unbeknownst to them the front door opened and Allie walked into Bobbie’s apartment. She heard movement from Bobbie’s bedroom and suspected that Bobbie had tied one on last night and was running late for work. She stuck her head around the bedroom door.

“Hey girl, are you coming to work today or… whoa! Guess I’ll come back later,” Allie caught a glimpse of Bobbie lying on her back with her feet in the air and Tony Siceresso between her legs humping away.

Bobbie and Tony lay on their backs, their desire sated. Their fingers were intertwined beneath the sheets because neither could stand not touching the other.

“What now?” Bobbie asked.

“We stay in bed all day and then we go to out to dinner tonight with Allie and her beau,” Tony reached for his pants to fish out his cigarettes and lighter.

Bobby had a thousand questions but for now she was just content to have Tony beside her in her bed.

*****

“You don’t seem surprised to see me,” Tony stood up and kissed Allie’s cheek and shook Randy Middleton’s hand and introduced himself.

They were at a very nice restaurant and Tony was behaving as if he didn’t have a care in the world.

“I saw you earlier today but I saw you were busy so I didn’t want to disturb you,” Allie gave Bobbie a knowing grin and Bobbie blushed.

Tony told them all about being sequestered in Witsec until after the trial and explained that he had some waters to smooth and arrangements to make before he could return to Miami.

“So the gist of it is I’m free and clear. The Feebs and GBI gave me a free pass and the guys in New York and the Dixie Mafia have made business arrangements with some of the old guys who used to be in the Siceresso crew. I’m out of it and I’m going legit,” Tony glanced around to make sure he wasn’t being overheard.

“I own another nightclub, two restaurants and a hotel that Feebs can’t touch because they are legitimate business and I still have the Dream Palace,” Tony explained.

“The Dream Place is yours Allie,” Tony produced a document and placed it on the table.

Allie read the deed of ownership and squealed with delight when she saw her name on it.

“And? What about us?” Bobbie nudged him.

Bobbie had been trying to get Tony to tell her what the future held for them all day but Tony refused to tell. He just teased her telling her everything would soon be revealed.

“You and I are going to live together in the penthouse suite of my hotel and you are going to help me manage my businesses,” Tony said smugly.

“And why am going to do that?” Bobbie smiled coyly.

“Because you love me, and I love you. I love you with all my heart,” Tony turned to Bobbie and kissed her.

Allie smiled and squeezed Randy’s hand.

“I love a happy ending,” Allie whispered into Randy’s ear.

Epilogue

Mandy and Charlotte sat at a table outside a trendy coffee shop in Buckhead Village. The day was bright and clear but there was a chill in the air reminding them that winters in Atlanta can be just as cold as anywhere else. They wore woollen skirts, winter tights, boots and scarves and were comfortably warm, sipping hot chocolate while they talked.

Charlotte was pregnant and most of their banter was about the new baby but they both scanned the crowd and looked up expectantly whenever a man approached the coffee shop.

Mandy had married her divorcee and was now Mandy Shrivington and lived in a nice house not far from the mall. Charlotte had married her college beau but had still completed her management degree majoring in digital marketing. Charlotte and her husband ran a small business specialising in copywriting, graphic design, and web development. The business was flourishing and Charlotte and her husband lived comfortably.

They seldom spoke about Charlotte’s father and had put that part of their lives behind them. They were both surprised when they received an email sent from Robert Valentine's old email account requesting to meet them both on neutral ground so to speak. They had debated whether or not to agree to the meeting but in the end they had acquiesced. Charlotte wanted closure and Mandy had to admit that she was curious about what had become of her former husband. Neither of them wanted him back in their lives.

A woman approached the coffee shop walking gracefully but purposely. She was wearing an expensive faux fur coat open at the front to reveal a designer burgundy silk dress cut to flaunt her figure. She was tall, narrow shouldered, small-breasted, wide-hipped with an hourglass figure and long legs clad in opaque black tights and her red-soled Louboutin heels click-clacked on the pavement. As she got closer they could see that her face was stunning, her makeup impeccably applied to a perfectly symmetrical face and accentuated her large green eyes, slender nose, pronounced cheekbones and plump lips. Her visage was framed by glossy, shoulder-length jet-black hair.

The woman looked like a mature-aged model and both Mandy and Charlotte disliked her on sight. She looked like she had stepped off the set of one of the Real Housewives franchises.

They were both surprised when the woman made a beeline toward their table and sat down across from them.

Mandy and Charlotte looked at each other quizzically then at the woman sitting across from them

“You're sitting at the wrong table,” Charlotte said making no attempt to hide her contempt for this Buckhead Betty.

“Oh, I don’t think so,” the woman smiled at them both, her voice a sultry feminine rasp.

Mandy dropped her mug on the table, hot chocolate spilling over brim.

“Robert?” she gasped.

“I used to be. Now I’m Bobbie,” the woman replied.

“Daddy?” Charlotte sat open-mouthed, staring at the woman.

Bobbie just raised her brows and smiled.

“What happened to you?” Mandy was finally able to get over the shock.

“I can’t tell you all of it but I’ll tell you what I can. I think we all deserve closure,” Bobbie hooked a red-painted fingernail towards the waitress and ordered a caffè latte and two more hot chocolates.

The End


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