Prison Dolls Ch. 02

"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.