Prison Dolls - Chapter 2

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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

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As usual always entertaining

Jill Jens's picture

I especially love the insights into Bobbie’s transition. I am always appalled at the lack of appreciation for your stories, if the number of kudos is any indication. 621 reads and only 26 kudos and only one other comment. Looking forward to the next chapter.
I will be sure to leave a few more admiring comments and hope that others will do the same. Thanks again for your efforts making this site successful.

Jill