Prison Dolls Ch. 03

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.