Prison Dolls Ch. 02

"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.