Prison Dolls Ch. 03

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.