Prison Dolls Ch. 01

"Jesus! That's you?" Tig said incredulously.

Allie Katt was stunning. Tall and curvy with long legs and a beautiful face. In some of the pictures she looked exactly like what she was: a drag queen. But in other pictures anyone would be hard pressed to think that she was anything other than a beautiful, desirable, sexy woman.

"Let me get to the point. Does Allie Katt get hit on much?" Tig asked blatantly.

"Oh honey the world is full of tranny-chasers. A lot of them are straight men too believe it or not. Of course I've also been known to kai-kai with other queens occasionally," Allen batted his lashes at Tig who noticed that Allen was wearing a hint of eyeliner and mascara.

Tig didn't ask what kai-kai meant... he could guess.

"And?" Tig raised his brows.

"Honey, if a drag queen gets caught sellin' her ass while she's pageanting or up in the club, her ass is grass. But what you do outside of that is your own business and some of them tranny chasers got lots of money," Allen mimicked street talk and batted his eyelashes at Tig and smiled.

"Let me put something to you," Tig looked around conspiratorially and began to whisper.

Tig thought long and hard about it and finally summoned up the courage to take his plan to his bosses. They sat around a laptop looking at cheesecake pictures of Allie Katt.

"That's some fine broad... pretty face, nice long legs, nice tits, great ass but so what? Are you just trying to give me blue balls?" Sal Siceresso growled.

"What if I told you that she is here in Brentwood?" Tig grinned at his lords and masters.

"Get the fuck outta here!" Joey Malzone exclaimed.

"Wait a minute. This broad is a fanook?" Sal's demeanour soured.

"Get the fuck outta here Tig. Anyone finds out that we're fucking a fanook in here and our reputation is toast. That's beside the fact that I ain't gonna fuck some broad up the ass while her dick swings freely in the breeze," Sal growled.

"Who's gonna know? Allie won't come in from outside the prison, she's already here. You never see her except when she's you know... Allie. She tells me the queens got this way of hiding their junk so you never see it. You guys have fucked boards up the ass before, I heard you talking about it and she tells me she can suck a tennis ball through a garden hose," Tig shrugged his shoulders is if to say que sera, sera.

"Get the fuck outta here Tig," Sal Siceresso growled again but Joey and Petey kept shuffling through the onscreen pictures of Allie Katt.

They cornered Tig later away from the others.

"She's gonna look exactly like that? She's gonna look like a woman, walk like woman, smell like a woman, talk like a woman and we aint gonna see her braciole?" Petey asked anxiously.

"Not unless you want to," Tig smirked.

Joey grabbed Tig by his shirt collar and pushed him against the wall.

"You don't joke about this shit! Anyone finds out Tig and it's you who is getting his braciole chopped off," Joey snarled.

"Absolute discretion boss. Gimme a couple of days to bring in the necessaries and I'll bring Allie to you and Petey and you can try before you buy so to speak," Tig eased Joey's fingers from his collar.

"What about this Allie?" Petey asked.

"I pump up her commissary and drop a few bucks into her outside savings account as payment. I bring in everything she needs to do what she needs to do. I tell you guys, this broad is a doll, you've seen her pictures," Tig said enthusiastically.

"See, we're already calling her 'she' and Allie. No reason to think she's anything other any other than a hump," Petey agreed.

And so it was done. Allie knew her sizes and she went on an online shopping spree ordering dresses, shoes, lingerie, hosiery, cosmetics and the other essentials a 'tranny' needed to pass. She forwarded her shopping list to Tig who agreed to purchase half the clothes and shoes she asked for. Until his bosses told him that they were satisfied with Allie's 'performance' he wasn't obliged to invest too much money into the venture.

"These men want the full fantasy right? They want me to be as convincing as possible. Well that means you gotta front up some good quality merchandise, you get what you pay for, you know what I mean?" Allie tried to convince Tig to buy everything she had ordered but Tig told her to make do.

Three days later the goods were delivered to Allie's room.

"Come back in two hours sugar and I'll show you what you paid for," Allie winked at Tig and eased him out the door.

As a drag queen Allie wore hip and buttock pads and breastforms to present an exaggerated female physique whilst performing. But she was not presenting as a drag queen she was presenting as a transvestite and the padding, prosthetics and exaggerated stage makeup would not be required.

Allie was tall, slim and hippy and could get away without a corset. She had ordered a couple of good quality wigs but for her debut she would use her natural hair which was shoulder-length brunette. Allie visited the inmate who operated the barbershop and paid him to cut her hair into a shag bob with bangs. Sitting in front of her mirror she teased it until it framed her face perfectly and then she set it. She went to work on her makeup, tucked and taped and rolled on a pair of fifteen-denier sheer to the waist pantyhose to hold everything in place and pulled her white satin panties tight over the pantyhose. She adjusted the brassiere and slipped two 'chicken fillet' prosthetics in the cups to give her some shape.

Tig returned at the appointed hour and knocked gently on the door and entered. What he saw took his breath away.

Allie was stunningly beautiful. Her perfectly made-up face was framed by her bangs and bob, her long elegant neck atop perfect unblemished shoulders and petite décolletage which was exposed by a low-cut emerald-green satin sheath dress. The dress was floor-length and spilt up one side to the hip. Allie stood with one leg thrust forward to show off her long shapely legs, her feet shod in green high-heeled pumps. She had accessorised with silver jewellery set with faux rubies. She was clouded in a miasma of exotic perfume.

Any man would be hard pressed to recognise Allen Kettering inside the visage which was Allie Katt.

"Fuck me!" Tig was agog.

"No honey. That's my line," Allie replied with a sultry feminine rasp that sent shivers down Tig's spine.

"Wait here," Tig left Allie's room and walked down the corridor.

He advised every inmate he saw to keep their mouths shut if they knew what was good for them and went back to Allie's room.

"Let's go," we hooked a finger at her and Allie picked up her clutch and followed him out into the hallway.

To some extent walking down the corridor reminded Allie of walking from her dressing room to the stage. To all intents and purposes she was about to give the performance of her life. She felt comfortable, feminine and desirable dressed as she was. Allie would normally be padded, corseted and be wearing stoned fishnet tights over two pairs of sheer pantyhose to keep her hip and buttock pads in place and be wearing heavy stage makeup and a big lace-front bouffant. She would be sweaty and a little uncomfortable dressed in drag but dressed as she was tonight she felt every inch a woman.

During the walk to Seg Tig gave Allie some final instructions.

"These guys won't take any shit. They expect you to behave like the type of woman they might pick up in a nightclub; think high class hooker. You do whatever they say and under no circumstances do they want to see your dick," Tig rattled for what must have been the twentieth time.

"I get it. Show them a good time and keep my dick tucked. It's not like I haven't done this before," Allie harrumphed.

"And check the attitude. You take the PrEP?" Tig glowered.

Tig was beginning to wonder if this was such a good idea. Allie Katt was a stunner but she had a mouth that could get them both in trouble.

"Yeah, I took the PrEP. I was on it right up until I was incarcerated. You checked with medical so you know I'm HIV negative and free from STDs," Allie snapped back.

Despite the widespread use of intravenous drugs and homosexual sex few prisons provided PrEP or condoms to the inmates. It was being considered by the DoC but the wheels were moving slowly. Wakefield Services was considering providing the service in the prisons the company managed, passing on the costs to the State of course at inflated prices.

Tig had added PrEP to the list of medications he smuggled into the prison for his bosses. He was taking no chances with Allie because Allen Kettering was gay and might have hooked up with other inmates. He also smuggled in Viagra for his bosses to take during their conjugal visits.

Joey and Petey were waiting just inside the door and when Tig punched in the code they anxiously shepherded Tig and Allie into Joey's room and closed the door.

"The other guys are playing poker," Petey Gruffalo said just above a whisper.

Joey said nothing. He was too taken with the stunning woman reeking of perfume standing only inches away from him. He reached out and stroked Allie's cheek and she smiled at him seductively. Her skin was smooth and soft and Joey was already enraptured with her,

"Never mind who is doing what. Come back in a couple of hours Tig and collect Allie. Go and shoot the shit with the others. Lose some money and keep them away from my room," Joey pushed Tig towards the door.

Tig left the room and heard the door lock behind him. He hoped he'd done the right thing. He sauntered off to lose a few hands of poker to his bosses and keep them occupied while Joey and Petey tried out Allie Katt to see if she was to their taste. He was worried that Petey and Joey were going to be aggrieved or disgusted and take out their anger on him. Also, Allie was a looker but she had a sharp mouth.

"Are you two boys going to keep staring at me or are you going to offer a girl a drink before we have a good time?" Allie said salaciously.

Tig needn't worry. Allie's mouth and attitude ingratiated her with two gangsters who found her brazen assertiveness charming. It helped that she looked stunning and her sultry voice was seductive. Neither of the men thought of her as a 'fanook'. She was sexy and desirable and cheeky and all they could think about was their Viagra-assisted hardons.

Petey poured expensive scotch whiskey into crystal tumblers while Allie sidled up to Joey and pressed herself against him.

"You like what you see?" she smiled seductively at him and Joey pulled her into his arms and kissed her.

Allie kissed him back. Allen Kettering liked big powerful men and so did Allie Katt, even more so. She could feel Joey's cock pressing into her despite his substantial gut.

"I see you're happy to see me big boy," Allie squeezed Joey's cock through his pants.

"What about you there mister? You want some of this too?" Allie pirouetted out of Joey's grasp and fell into Petey's arms.

She snuggled up to him and kissed him. Petey was instantly hard. This girl was so sexy and womanly. She was brash and lewd and totally fuckable. They both forgot that Allie was actually a resident in the same prison. All of their fantasies were being fulfilled as she flitted from one to the other, kissing, fondling and caressing Joey and Petey until the men just wanted to pounce on her.

"How's this gonna work? You gonna do Petey first, then me?" Joey asked kicking off his shoes and tugging at his pants.

"You boys aren't shy are you? Why don't you do me both at the same time? I've got two holes," Allie winked at them and hopped on the bed.

"It's my room; I should go first," Joey whined.

"Fuck that! I got seniority," Petey growled.

"Come on boys. Don't argue. There's plenty of me to go around," Allie called from the bed.

She had shucked out of her dress and was dressed only in her tight white panties, shimmering pantyhose and heels. She'd ditched the chicken fillets and her erect little nipples pushed against the sheer fabric of her transparent brassiere.

She looked coquettish with her pretty face framed by her shoulder-length brunette bangs and bob. She lay on her back kicking her legs like a showgirl, smiling at the men seductively. They both admired how the panties clung to her buttocks, the valley of her natal cleft visible through the slinky panties and super-sheer pantyhose. Most of all they admired the perfect Vee between her legs. They both knew that there was no vagina there but that was last thing on their mind.

As the two men approached the bed Allie got on her hands and knees.

"It's simple arithmetic boys. One in front and one in back," Alley eased aside the gusset of her panties showing off her perfect gleaming globes.

She slipped a blood-red fingernail into her ass crack and snagged a little hole in her pantyhose so that her puckered bud was visible.

Both men swallowed and leapt on the bed.

Allie had pre-lubricated and when Petey's hard cock slid into her ass there was no resistance.

"Oh god yes honey you are tight," Petey moaned.

Allie couldn't answer because Joey's cock was in her mouth and she was suckling on it like it was a lollypop. She worked her lips up and down the shaft and used her tongue on the sensitive glans, swallowing the copious amounts of precum dribbling from Joey's cock.

He was on his knees in front of her watching her pretty mouth work his phallus while Petey fucked her from behind. Allie got into rhythm, pushing back against Petey's thrusts while her mouth slid up and down on Joey's quivering organ.

Petey came first, ramming his cock all the way inside Allie's tight rectum, grinding his pubis into her pantyhosed buttocks. He held her high heels in each hand while he unloaded his issue deep inside her. Allie moaned appreciatively around Joey's cock and slathered at the thick veiny member, feeling it judder. Then her mouth was filled with his sweet, musky spunk.

It had taken Allie less than ten minutes to make both men cum and she was feeling very self-satisfied.

The men clung to her, unwilling to let her go. She was amazing: sexy, vivacious, cheeky and seductive.

Allie looked up at Joey and smiled, his deflating lipstick-smeared penis inches from her face. He had a satisfied smile on his face.

"So you boys wanna change ends and go again?" she smirked.

Petey and Joey took a half hour break, swapped ends and came back at her again and Allie was more than ready to oblige. This time it took a little longer for the men to cum but Allie made sure that they were both satisfied. She quite enjoyed it herself but made sure that her tuck stayed put despite the pain of having her semi-erect penis taped long her perineum.

When the men were finished Allie took her dress into the bathroom, cleaned up, fixed her hair and makeup and put her dress back on. When she emerged she looked as stunning as when she had first arrived.

"How did I do boys? Did I pass the test?" Allie beamed at them.

"You sure did doll," the men said in unison.

Joey went to find Tig while Petey kissed and canoodled with Allie for a little while, then Tig lead Allie back to D Block.

Joey and Petey got together with Sal, Tony and Mike and told them about their encounter with Allie. They told their comrades how Allie presented as a feminine, desirable, sexy woman and how she gave great head and how tight her ass was and how they hadn't seen anything that even looked like a dick. They explained how Allie was funny and engaging and good company, as well being a great hump.

Tony and Mike were keen to try her out but Sal was still sceptical.

Tig was told to bring Allie to Seg again the next night and she was everything that Tig, Joey and Petey said she was. She was engaging and cheeky and sexy and Tony and Mike became as besotted with her as Joey and Petey were and after drinks and some banter they took her away and sampled her wares and were not disappointed.

Allie became a regular fixture at Seg. Every night she would go there and entertain the men and eventually even Sal relented and took her to his room and was also not disappointed.

The five gangsters had no idea that Allie Katt was in fact Allen Kettering. Of course they knew deep down that Allie was another inmate who lived only yards away from them in another wing but they didn't want to acknowledge that. They only ever thought of Allie as an enchanting female companion who was amazing in bed.

It soon became apparent to Allie and to Tig that Allie couldn't keep up the demanding workload placed on her. She was in Seg almost every night and on all of those nights she was required to perform sexual congress with at least two of the men, usually more. There just wasn't enough Allie to go around. She was a victim of her own success.

"We need another girl," Allie confided to Tig after a few weeks.

"I can't keep this up; my ass is going to prolapse and I'm going to get lockjaw. All joking aide, I need a partner" she sighed.

"How we gonna do that?" Tig asked.

"Leave it to me. Can I offer her the same deal?" Allie replied.

"Sure but you gotta make sure she can keep her mouth shut. No one in genpop can know what happens in Seg," Tig warned.

"I'm on it honey. Be prepared to take another order for clothes, makeup and all that shit. I'm going to make you another girl," Allie quipped confidently.

Maurice Shrew took little convincing. He was a gay man without a life partner who played the field. Whilst the idea of crossdressing to service five old mobsters was not that appealing, the regular stipend into his commissary and bank account was.

As it turned out Maurice was a natural and with some coaching from Allie was soon presenting as Marilyn, the femme name she chose for herself, which Allie thought showed little imagination but it didn't matter because Marilyn was quite the dish. After a week of coaching Marilyn made her debut in Seg and was an instant hit.

Between them, sometimes singly but mostly working together, Allie and Marilyn spent most evenings in Seg entertaining the five mobsters, enjoying the opulence, the attention, the sex, and of course the money. Marilyn took to her job like a duck to water and soon came to enjoy dressing and presenting as Marilyn.

The Siceressos used the affectionate euphemism doll with Allie and Marilyn: 'Come here doll and sit in my lap', 'yes doll, suck it just like that', 'can't wait to get my hands on those dolls; I'm going to shove my braciole right up Allie's ass'.

And so Allie and Marilyn became their prison dolls. It was a convenient circumlocution, not expressly gendering the 'dolls' as women but repudiating their true gender. The Siceresso bosses didn't know the male identities of Allie and Marilyn nor did they ever want to. That would ruin the illusion. That was left to Tig who filled the role of their whoremaster.

Tig Hansen had done well and was rewarded by his bosses accordingly. After a while, other than ordering and paying for his 'girls' feminine requisites, he didn't have much to do with them at all. The girls were given the passcode to the entrance door to Seg and came and went as they were needed.

The Warden was in the pocket of the Siceresso crime family and she made sure that what happened in Brentwood, stayed in Brentwood. The prison officers, all employees of Wakefield Services and selected personally by her, knew to keep their mouths shut and they didn't even acknowledge that Seg existed and ensured that the existence of Allie and Marilyn remained a secret to the outside world. Tig used coercion, blackmail and bribery to keep the populous of D Wing, where Allie and Marilyn were quartered, in line.

Being a privately run prison, the DoC had little oversight into the management and day-to-day running of the Brentwood Correctional Facility. Wakefield Services met and exceeded their KPIs. There were no breakouts and few disciplinary problems and few, if any, complaints from the inmates. The Siceressos ensured that Wakefield Services kept the inmates content with good accommodation, excellent amenities and fair work practices. The inmates at Brentwood knew they had it good and made it their business to keep schtum about anything they suspected about the existence of Seg and the goings on associated with it.