Prison Dolls Ch. 02

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.