Chapter 3: Red Roses Dropped On Fresh Snow

Traitors – Time Takes Its Toll

The thing about prison is that you are seldom alone ... but you always feel like you are.

Robert kept to himself and the other inmates in D Wing mostly kept away from him anyway. Most of them knew about Bobbie and Marilyn and kept their distance, especially when Tig was around because of his overt aggressiveness.

Except for when she presented as Marilyn, Maurice Shrew had little to do with Robert. Bobbie and Marilyn weren’t competitors but they just had nothing in common with each other other than being transvestites who serviced the men in Seg. There were two other openly gay men in D Wing who were friendly with Maurice and Robert suspected that Maurice was having sex with both of them. Maurice only presented femme for the money and during the day he went to work keeping book at the prison farm while Robert worked in the laundry.

After living a double life for what seemed like an eternity, Robert no longer dreaded dressing as Bobbie and carrying out her duties in Seg. In fact Robert began to look forward to it, or at least his alter ego Bobbie did. Robert was worried that Bobbie was taking over his life. She drifted in and out of his conscience so freely now.

When he laundered his and Marilyn’s ladieswear in the laundry Bobbie would remind him that he needed new lingerie or dresses or heels. She would take over his psyche when Robert placed his orders with Tig. She was reluctant to let go when Bobbie returned to her room after spending the evening in Seg. If he was honest with himself, Robert would have to admit that he was more comfortable when he was Bobbie ... and that was worrying. Existing as Bobbie was an escape. An escape from prison, an escape from Robert’s bland life, an escape from Robert’s responsibilities and an escape from his family who seemed to be distancing themselves from him.

He and Mandy were drifting apart. Although they still took advantage of the monthly conjugal visits they were distant with each other. Robert suspected that Mandy was only attending the conjugal visits to perform her ‘matrimonial duties’. Except for the sex, the closeness they felt was no longer there. They were a man and woman who fucked each other out a sense of obligation. Mandy had almost ceased attending weekly visitation saying that the long drive was arduous and sitting in the prison visiting room made her depressed and Robert didn’t protest. He felt the same.

Their correspondence was rudimentary, mainly talking about finances, their daughter Charlotte who would soon be graduating, and gossip about the few relatives who had remained close. With Robert’s stipend supplementing her wages Mandy was able to pay the residency fees at Middle Georgia State University and Charlotte had moved into the college residency. Charlotte had a steady boyfriend and she visited home less frequently.

The truth of the matter was that Mandy was lonely and she had started dating a divorcee at work. At first it was just friendship, someone to go to dinner with, see a movie or go to the theatre. Then they went dancing and ate late night suppers and then they started seeing each other on the weekend and finally Mandy had ended up in his bed.

The guilt that Mandy felt was nearly as crushing as the guilt that Robert felt about keeping Bobbie’s existence a secret. They both felt like traitors. Mandy started to hint that she was friendly with a man from her office and rather than being horrified Robert was relieved. He guessed that they were fucking and Robert understood that the relief he was feeling was guilt transference. It had gotten to the point where he perceived Mandy as the guilty person in their relationship. He convinced himself that he was being forced to be Bobbie but Mandy had become an adulteress of her own free will.

To make matters worse Bobbie and Tony Siceresso were not just fucking in Seg, they had become secret lovers. Bobbie was always Tony’s favourite, he hardly ever had sex with Marilyn and he continued to do so only to avert any suspicion that Bobbie was anything other than a whore to him. Even so, Tony was teased by the others about his preference for Bobbie over Marilyn.

“She’s just a better fuck,” Tony said flippantly when questioned about it.

Their relationship had developed slowly at first. During the first few months of her existence Bobbie had dreaded visiting Seg. Eventually transforming from Robert to Bobbie had become easier and Bobbie was able to slide easily into Robert’s consciousness and take over. Bobbie actually liked being who she was. She had shed the excess pounds and she tried different makeup styles to match her moods and her outfits and tried wearing wigs of differing styles and colours. She became fashion conscious and extended her wardrobe.

But at first the sex was difficult. She realised that the men in Seg had different demands. Mike Giacomo she called Doctor Jekyll and Mister Hyde because sometimes he was affectionate and then on the turn of whim he could be cruel and demanding. Sal was a gentle old soul whose penchant for the dolls waxed and waned. He wasn’t very good at sex but he enjoyed their company. Petey Gruffalo liked sex but was prone to post-coital regret. He loved being in the company of the dolls and he liked taking them back to his room but once he had climaxed he wanted them gone. Joey Malzone also enjoyed the company of the dolls but he used them the same as he would use any of the whores that he used when he was a free man. There was little real affection.

Bobbie soon worked out how best to please the men in Seg and moderated her behaviour accordingly. She was enthusiastic and affectionate when it was called for or she just behaved like a whore when needed and sometimes she just lay on her back, knelt on the bed or stood against the wall with her skirts hiked up while she was used.

The sex was so frequent that it became tolerable. Then she began to enjoy it. Not always but on most occasions she would become sexually aroused and actively participate. She always kept her genitals covered but more often than not she would become tumescent and sometimes climax. The first time this happened was with Tony Siceresso.

Bobbie recalled the first time she and Tony Siceresso were together intimately.

Bobbie and Tony – A Blossoming Romance

The word entertain had taken on a new meaning. It meant everything from engaging in polite conversation, to dancing, to playing games with the men but mostly it meant providing sexual favours. When Tig told her at lunch that she would be required to entertain in Seg that night, it meant that she was going to be fucked or at least be used orally. When she attended Seg she was usually in the company of Marilyn but sometimes only one of the dolls was required depending on the disposition and the needs and wants of the men in Seg.

As always she took advantage of the alcohol and drank as much as she could to numb her senses. One evening a few months after her debut, she and Marilyn went to Seg as usual. Sal and Mike weren’t present and after a few drinks Joey led her to his room but he only wanted a quick blowjob and Bobbie satisfied his needs and he sent her back to the playroom. Petey Gruffalo was getting cosy with Marilyn and Tony poured Bobbie a drink and sat down beside her.

“Here, you look like you could use this,” Tony Siceresso handed Bobbie a drink and offered her a cigarette.

Georgia had banned tobacco use in all of its prisons long ago but the men in Seg weren’t subject to any restrictions and some of them smoked. Robert had given up smoking in his twenties and still didn’t smoke. Bobbie had taken it up immediately as another coping mechanism along with the alcohol. It helped calm and distract her while she entertained in Seg.

Bobbie leaned forward so that Tony could light her cigarette. She absentmindedly placed her hand on his knee as she leaned in and almost and as soon as she was aware of the transgression she snapped it back. Bobbie was still uncertain about the rules. Was she supposed to be forward or was she supposed to be demure? She envied that Marilyn seemed to know exactly how to act. She seemed to know when to be flirtatious and when to be reserved, Bobbie was still feeling her way.

Tony took Bobbie’s hand and put it back on his knee.

“I like your nailpolish,” he commented looking down at her bright red fingernails.

Bobbie just nodded and gulped her drink.

“How are you settling in?” he asked.

Bobbie knew that she had to be careful. She recalled what Allie Kat had said to her: ‘What’s the number one rule - don’t show your dick and never break character.’ She also remembered what Mike Giacomo had said to her: ‘We don’t want to hear anything about your life. We aren’t interested.’

“Just fine. I enjoy the luxury of this place,” Bobbie replied coolly.

Tony chuckled.

“You are a very beautiful woman,” Tony stroked her cheek and Bobbie blushed.

She finished her drink in one gulp and crushed out the cigarette.

“Wow! You are one thirsty girl,” Tony chuckled.

“I’d like to take you back to my room so we can have a drink in private,” Tony placed his hand on top of hers.

Bobbie guessed that ‘have a drink in private’ was a euphemism for sex.

“Sure, I’d like that,” Bobbie lied.

She just wanted to get it over with so she could return to D Wing.

Tony led Bobbie to his room and closed and locked the door. Bobbie sat on the big sofa. It was a large modular ottoman that functioned as a day bed. Bobbie perched herself on the edge, her ankles crossed demurely while Tony went into the bedroom. He returned wearing a short velvet robe tied at the waist. Knowing that Tony was naked under the robe just confirmed that he wanted her for sex, not for conversation. She sat primly, resigned to her fate.

Tony poured them both a drink. This was unusual. Normally the men wanted to get right down to it but Tony didn’t seem to be in a rush. Bobbie figured that because Marilyn was entertaining Petey and the others were busy doing whatever they did in the office that Tony had decided not to rush but she knew that she would likely end up on her knees before too long.

Tony sat down beside her and gave her the drink and they talked. Tony told Bobbie that his wife had divorced him not long after he was incarcerated. Their marriage was on the rocks before he went to prison and as they had no children his wife was happy to settle for the house and a ton of cash and agree to an uncontested divorce. The men seldom discussed their personal lives and Bobbie was surprised.

“Allie sends her regards by the way,” Tony segued the conversation completely, throwing Bobbie into confusion.

Allie had told Bobbie that once she was released from Brentwood that she was to going to be rewarded for her services and had been offered a well-paid position hosting the drag show at one of the Siceresso’s nightclubs.

“She’s managing the Dream Palace nightclub in Miami and has begun transitioning,” Tony stated as if he was just talking about a mutual friend.

This surprised Bobbie. The men in Seg never acknowledged that the dolls were in fact female impersonators and seldom spoke about them outside the context of sex. Bobbie remained silent but attentive.

“I own the Dream Palace. It’s one of the many legitimate businesses that I retain in Miami,” he continued.

“Allie keeps in touch?” Bobbie ventured.

“Only with me on a personal level, not with the others,” Tony smiled and Bobbie couldn’t help but smile back.

“She was never just a doll to me. We were ... intimate,” Tony surprised Bobbie yet again.

He placed his hand on hers again and intertwined his fingers in hers. It was such a gentle intimate gesture that Bobbie was taken aback. Then Tony leaned in and nuzzled Bobbie’s neck, inhaling her perfume, kissing her delicate flesh softly and tenderly. Bobbie sensed a peculiar sentiment materialise and then she realised that Tony was displaying genuine affection.

Bobbie turned to face Tony. He was handsome and faultlessly groomed. His hair was thick and black, his olive complexion and muscular body would be alluring to most women. Up until now Bobbie had not considered the handsomeness of the men in Seg. She gauged them by their temperament and their desires. They were innominate entities who treated her decently enough in the company of their compatriots but in the bedroom they were just demanding dominant men who used her for their pleasure.

Bobbie felt totally feminine when she metamorphosed but that was uniquely self-induced. She knew it was more than a survival technique but up until now she didn’t acknowledge it. She knew that the men in Seg saw her as a pretty woman but there was no element of attachment or reverence. But somehow it didn’t feel that way with Tony. Maybe she was reading too much into it?

“You were intimate?” Bobbie asked; her voice just above a whisper.

“Of course we fucked. We both liked to fuck,” Tony chuckled.

“But I felt something for her beyond lust. We connected,” Tony was suddenly serious again.

“Prison is a lonely place despite the fact that I live in a palace with four other men. The intimacy I shared with my wife had all but dissipated by the time I arrived at Brentwood. Allie and I formed a relationship that I cherished and that I would like to replicate with you,” Tony squeezed Bobbie’s fingers gently.

“She never told me. Of course she told me that I would be performing sexual favours but she never went into detail about her relationships with the men in Seg. I assumed she was just another concubine like me and Marilyn,” Bobbie replied, putting her drink down on the coffee table.

“She didn’t tell you about us because Allie could keep a secret. If the others found out that Allie and I were actually lovers and that I had genuine feelings of affection for her, that I saw her more than just a whore, there would be repercussions for us both,” Tony sighed, placing his drink down beside hers.

“I’ve told you too much too soon Bobbie but I trust you. Let’s just see what develops between us, take it as it comes so to speak. One thing Bobbie. What happens in this room stays in this room. No one can ever know,” Tony leaned in and kissed Bobbie on the mouth.

The kiss lingered and soon tongue was introduced and they lay down on the sofa and cuddled and canoodled. Bobbie lay on her back and Tony lay down beside her, kissing her, stroking her cheek and then he moved his hand down her torso to her breasts.

Bobbie was wearing a black leather miniskirt and a mauve satin blouse and Tony slowly unbuttoned it and slid his hand inside. Bobbie no longer wore breastforms so Tony was able to caress her nipples through the translucent material of her lacy brassiere.

Bobbie gasped as Tony gently caressed her tiny teats. When he lowered his face to them she guided his mouth from one nipple to the other as Tony lapped and nibbled on the sensitive buds. She was becoming tumescent and she could tell that Tony was too. She could feel the heft of his cock pressing against her belly. She instinctively reached for it knowing what was expected of her.

Tony caught her hand as it slipped inside his robe and gently removed it.

“There’s no rush Bobbie. I’ve waited quite a while for us to be able to be alone together without having to rush,” Tony smiled down at her and kissed her again.

The kiss was soft but the yearning was undercurrent. Bobbie suspected that Tony could quite easily mount her and satisfy his base urges but he was restraining himself. He was behaving more like a lover than a john.

He kissed her some more and Bobbie enjoyed every second of it. The featherlight pressure as their lips touched, the delicate way in which he slipped the tip of in tongue into her mouth. The way he was holding her like she was precious, not like some fuck puppet. His fingers played with her breasts and then slowly began the journey down her torso, down her skirt and finally came to rest on her legs.

He stroked the back of her knees, his fingers tickling the little wrinkles in her pantyhose and Bobbie shuddered with delight. Then his hand began to creep upwards, under her skirt, tracing her thighs, finally coming to rest in the crevice where her legs joined her hips. He stroked the delicate flesh there and Bobbie gasped into his mouth.

His touch was so tender and erotic. It was as if Tony was trying to seduce her. She yearned for him, searching out his manhood but once again he brushed away her hand and instead she laced her fingers behind his neck and returned his kisses, slipping her tongue into his mouth, pressing herself against him.

Tony’s fingers slid across the front of her panties and Bobbie froze. The men would often play with her ass but they never touched her pubis. She knew that the men in Seg never wanted to break the illusion that she and Marilyn were women.

Bobbie put her hand down there and gripped Tony’s wrist and looked at him with trepidation.

“What are you doing?” she whispered.

“What I’ve be aching to do honey,” Tony smiled at her and shook off her grip.

He pressed his lips to hers and drove his tongue into her mouth. His fingers continued their journey across the front of her panties. Then moved up to her waist and slipped inside the waistband of her pantyhose and continued down between her legs.

Bobbie shuddered and gasped as Tony freed her penis from between her legs. Her cock was semi-tumescent and Tony laid it flat against her belly and hitched up her panties to cover it. Bobbie’s testes descended into her scrotal sac. Tony stroked the bulge in Bobbie’s panties as he kissed her passionately and Bobbie was filled with trepidation but also lust. His fingers brushed her satin panties against the tight nylon of her pantyhose which swathed her now fully erect penis. It was heavenly.

“Do you like that Bobbie?” Tony broke the kiss and smiled at her.

Bobbie’s response was to pull Tony’s face to hers so that she could kiss him and wriggle her bottom appreciatively. She felt Tony smile around the kiss and she realised that this had been his plan all along. No wonder he had sworn her to secrecy.

Tony stroked her cock through her panties and Bobbie reached for his. This time he did not bat her hand away and she found him turgid, his glans dripping precum. His penis felt huge in her delicate fingers and she began to stroke it and was rewarded with a gasp and a shudder as Tony felt Bobbie’s fingers manipulate his throbbing manhood.

She was gentle and fondled his cock softly, sensing that Tony was in no rush to consummate their tryst. They kissed and canoodled and once again Bobbie was overcome with a feeling that she and Tony were actually making love, not just having sex. There was no urgency, no race to climax, they were tender with each other and Bobbie was surprisingly delighted.

Tony nicked a little hole in the front of Bobbie’s pantyhose and guided her penis though the hole and took it in his hand. Bobbie was at once excited and trepidatious. None of the men in Seg had ever touched her penis, not even through her panties and here was Tony stroking her naked flesh.

They fondled each other genitals, cupping scrotums, stroking shafts, tickling fraenulums, their kisses becoming progressively more passionate. They edged each other towards climax and backed off when each sensed the other was close.

“Have you done this before?” Tony asked and with some difficulty he poked Bobbie’s hard cock back the through the hole in her pantyhose and smoothed her pantyhose and panties back in place.

“Have I done what?” Bobbie whispered.

“This,” he replied and rolled on top of her and pressed his cock against hers.

Tony kissed her passionately and she put her arms around him and lifted her legs and locked them around his waist. He loved the feel of her pantyhose on his tender flesh and she loved the feel of muscled body lying on top of her. She felt feminine and appreciated and also lecherous.

His cock pressed on Bobbie’s through the fabric of her slinky panties and hose and they both enjoyed the sensation of cock rubbing on cock. Their kisses became more passionate and then frenetic as they rutted against each other. Bobbie raked her nails down Tony’s back and buffed her silky-hosed legs against Tony’s flanks; he pressed down on her, grinding his cock against hers, relishing the sensations.

“I’m going to cum,” Bobbie whispered into Tony’s ear as she felt her climax welling up from deep inside her.

Her scrotum was roiling and ready to release her load. Tony’s cock was tingling with delight as he rubbed it faster against Bobbie’s panty-clad phallus. He felt his orgasm begin to build.

Tony broke the kiss and pushed himself up with his forearms so he could see their cocks frotting against each other and Bobbie shuddered and Tony smiled when he saw a globule of warm semen bubble through her panties. He rubbed his cock in the puddle of spunk and smeared it all over her panties and then he ejaculated too and his own seed comingled with hers as his orgasm washed over him.

Bobbie pulled him down and smashed her lips against his and drove her tongue into Tony’s mouth as she writhed and wriggled beneath him, pressing her cock against his as it juddered and spewed forth her creamy issue. The feel of Tony’s quivering organ spilling his seed on her pantied penis was ecstatic.

The two lovers kissed and cuddled and rutted and ground against each other, their cocks smeared with each other’s warm semen. Even after their orgasms had subsided they lay in each other’s arms and kissed and caressed each other.

“Did you like it?” Tony asked.

“I can’t believe you did that,” Bobbie gasped.

“Oh, I haven’t finished yet honey, that was just the appetiser,” Tony smiled down at her.

Bobbie was used to being dismissed once the man using her had climaxed but Tony clung to her and kissed her. They started all over again, Tony kissing and nibbling her tiny breasts, fondling each other’s cocks, urging each other on. Neither of them had become fully flaccid, they both maintained semi-erections and Bobbie felt Tony’s cock become fully engorged and to her amazement so did hers.

“Your cock is amazing,” Tony whispered as he ran his finger along the length of Bobbie’s hard phallus.

Bobbie was shocked. The men in Seg never acknowledged that their dolls had cocks. She just didn’t know how to reply because she had been conditioned never to talk about her penis while in Seg. Tony wasn’t expecting a reply anyway because he popped Bobbie’s penis out of the little hole in her cum-soaked pantyhose and began to stroke it again.

Bobbie sighed as Tony’s fingers fluttered expertly along her rod, eliciting little flowerets of pleasure. She reached for Tony’s huge cock, her fingers barely able to encircle the girth of it, and she returned the favour. They masturbated each other while they kissed, slowly building the intensity, their kisses becoming more fervid and their hands working faster, their cocks growing harder.

Tony took his hand away from Bobbie’s cock and he slipped it between her buttocks and made another hole in her pantyhose and slipped a finger into her anus. As usual she was pre-lubricated and it slid in easy so he slipped in a second finger and Bobbie gasped. But it wasn’t from pain, it was from pleasure. Tony knew what he was doing and he used the pads of his fingertips to massage Bobbie’s prostate. Her cock began to dribble precum in a continuous stream.

“Are you ready?” Tony whispered and Bobbie could only nod.

She’d never been asked that before.

Tony loomed over and lifted her legs and placed her ankles on his shoulders and he lined up his cock with her sphincter. He nudged his glans into the puckered bud and felt Bobbie tense, then she relaxed and Tony pushed the bulbous head of his cock inside the tight ring, stretching it open.

Bobbie thought her sphincter was going to tear as Tony’s bloated glans stretched her wide open. There was a slight sting and feeling of fullness but the pain was minimal.

Tony kissed her and stroked her and fondled her, just the tip of his cock inside her. He was patient and waited for Bobbie to become accustomed to the girth of it. When he felt her relax again he pushed an inch of cock inside her and Bobbie hissed so he stopped. His cock felt like it was being squeezed by a velvet glove.

“Are you ok?” Tony whispered.

“It’s big Tony but it feels wonderful,” Bobbie admitted.

She placed her lips on his and kissed him, feeling the fullness of his manhood dilating her anus. There was a deep ache but it was not unpleasant and her stretched sphincter was emitting ringlets of pleasure as the girth of Tony’s penis lit up the sensitive nerve endings.

Bobbie wriggled her bottom indicating that she was ready for more and Tony obliged, pushing in another inch or two, feeling Bobbie’s tight anus open like a tight furrow. She gasped again and mewled in his mouth but she clung to him lovingly. Then Bobbie surprised him and she wrapped her arms around his neck and used it as a fulcrum as she lifted her buttocks up off the couch and impaled herself fully on his mighty appendage.

As Tony’s big cock slid all the way inside her, Bobbie wanted to scream but the scream would have been a combination of pleasure and pain. His cock stretched her rectum until she thought it would split but under the deep ache was also a deep resonance of rapture. Her sphincter felt like it was lit up like a string of fairy lights, twinkling little sparklets of pleasure, while a deep reverberation of pleasure began to emanate all along the walls of her tight hole.

Tony took Bobbie’s cock in his hand, drove his tongue into her mouth and raised himself up and began to fuck her. Bobbie had never felt such pleasure before. Tony’s cock filled her void completely and lit up every nerve ending, the base of his cock stretched her sphincter which radiated ringlets of pleasure very time Tony thrust his huge hard cock inside her. Her prostate was stimulated to such an extent that her cock was dribbling a torrent of pre-ejaculate which Tony used to lubricate her penis as he stroked it.

Tony could feel Bobbie’s spongy mass enveloping his hard cock and it rippled and undulated as he drove his cock in and out of her, almost extruding his essence. Bobbie’s cock was throbbing in his hand as he caressed it. He alternated between softly massaging it and viciously stroking it. Their tongues were entwined and Bobbie had lowered her legs from his shoulders and locked them around his waist, drawing him into to her. He could feel her need, her wanton lechery and Tony obliged and began to jackhammer his cock in and out of her tight asshole and stroke her cock faster and harder.

This time Bobbie did scream with delight as freshets of hot spunk erupted from her cock. She pulled Tony tight and screwed her ass into his pubis, extracting every scintilla of pleasure from the monster cock that was impaling her tight anus. She felt Tony’s cock shudder and throb as Tony held her close, driving his tongue in her mouth as drove his cock all the way inside her and ejaculated.

They clung to each other, pressing themselves tight, Bobbie grinding her ass and Tony grinding his pubis as their orgasms washed over them. They squeezed very ounce of pleasure from each other until they were sated and Tony lay on top of Bobbie spent and exhausted.

Bobbie quite liked the weight of his body on top of her. It was comforting and pleasant and Tony was still kissing her but he was kissing her softly and tenderly, his needs met, their passion spent. Eventually Tony’s cock contracted to the point where it slipped from Bobbie’s anus. A flood of semen gushed from her still gaping sphincter and it was soaked up by her pantyhose and panties. It took a little while for Bobbie’s sphincter to close because Tony had stretched it so wide.

After the sex Bobbie and Tony lay in each other’s arms, caressing and kissing each other. This was divergent to what usually followed sex with the Siceressos. She was usually shown the door or escorted back to the lounge or playroom and seldom was any affection shown. Bobbie actually preferred it that way: the compliments, the interplay and the canoodling when she was in the company of the men; the rollicking sexual encounter in the bedrooms without any real attachment with the realisation that the dolls were just a convenient replacement for ‘real women’. It was another means of self-justification to Bobbie.

But this wasn’t that. Tony had shared intimate details of his personal life. He had intimated that he and Allie had a personal relationship that exceeded the bounds of sexual gratification. It seemed, at least for now, that Tony was interested in fostering a similar relationship with her.

He insisted that she take a shower and use his ensuite for as long as she liked and Bobbie enjoyed the luxury of it. She undressed and took a long hot shower and then she fixed her makeup. She took a new pair of pantyhose out of her purse and threw the ones with the holes, drenched in semen, into the little bathroom tidy. She tucked and took a fresh pair of panties from her purse and put them on, then her bra then her skirt and blouse. She stepped into her heels reapplied her makeup and brushed her hair and came out of the bathroom refreshed and smelling of Dior Poison.