Pillow Talk
By
Michele Nylons

Chapter One – Half n’ Half

Michelle Clooney stood on the windy cold street corner; it was gloomy, with most of the streetlights either deliberately broken to mask the street crime or simply blown and not replaced by a City Council that was going broke. The flickering neon signs of the titty-bars, greasy spoons, porno palaces, and sex shops reflecting off the cold black pavement providing the only light, besides the headlamps of passing vehicles.

Michelle blew into her cupped palms and then stuck her hands back under her armpits using her short faux leopard-skin fur jacket to keep them warm. She hopped from foot to foot trying to generate some body heat even though she was wearing precariously high platform heels and it was a dangerous manoeuvre on the icy sidewalk. The sheer pantyhose, velvet hotpants, and platform sandals she was wearing did nothing to keep the cold from her legs and feet.

She heard the footprints of a man approaching and began to strut her stuff, as did the other three hookers on corner. They were all scantily and provocatively clad despite the freezing weather.

The man approached Michelle directly, ignoring the other girls.

“What can I do for you?” Michelle asked, being careful not use any form of solicitation.

“Not here,” the man nodded to the dark alley behind her.

The alley was where the cheapskates liked to do their thing. No hotel fees and it was quick and easy.

“Jesus mister wouldn’t you like to go somewhere warm?” Michelle asked.

“Fuck warm. I want quick and cheap,” the man put his hand through the crook of her arm and began to lead Michelle into the alley.

He pushed her up against the rough brickwork behind the dumpster which shielded them from the entrance to the alley.

“So what you offering?” the guy asked, all business.

“What you want?” Michelle replied.

This was standard banter between hookers and Johns in the nineteen seventies where they danced around the subject of money for sex because neither wanted to be pinched for solicitation.

“Look honey; it’s too cold to stand here and argue. You get a BJ for ten bucks, a knee trembler for twenty, and half ‘n half for twenty five,” Michelle blew warm breath into her cupped hands again.

“I’ll take half ‘n half honey; but how’s about a little foreplay first,” the man in the business suit pushed Michelle against the wall.

Michelle was caught off guard. The man looked like a skinny little mouse but he was wiry and had considerable body strength concealed under that bulky overcoat.

He pressed his lips to hers and shot his hand down inside her hotpants, trying to squeeze her cooze. The man quickly snapped his hand away and staggered backwards; shocked.

“Jesus lady you’re a fucking tranny!” he whined.

“And you’re shit out of luck Willy Loman,” Michelle opened her jacket and flashed the New York City Police badge pinned to the inside.

“This is entrapment!” the man wailed.

A cop car crept silently down the alley until it was level with the dumpster then it briefly flashed its lights and gave a quick ‘whoop’ on the siren.

“Get in the car Romeo; you’ll probably make bail before I get off this fucking corner,” Michelle griped.

“Jesus! They got tranny coppers undercover now?” the man whined as the uniformed cop placed a hand on his head and helped him into the back of the prowler.

“Hey! We got what we got ok! The mayor said to sting prostitution so we sting prostitution. To protect and serve dickhead; any way we’re told to do so. Now shut the fuck up while I Miranda your ass,” the burly cop growled.

Michelle sauntered back to her corner and nodded to the other undercover hooker, Linda Gordon, a female Police Officer from the same precinct. As Michelle stood there in the cold waiting for the next John to come along she reminisced as to how she had ended up being this street corner.

Michelle Clooney was actually Detective Third Grade Mitchell Clooney of the NYPD’s 41st precinct. He hadn’t had his gold shield for very long at all when he was swept up in an anti-corruption sting and caught taking a bribe from a narcotics distributor. Suspended without pay and ostracised by his fellow detectives, who were just as corrupt as him but shit scared they would be entangled in the same sting, he was left all alone.

New York City Mayor Abe Beame was under pressure to battle the ever rising crime rate but had no money and an ever shrinking police force as President Ford refused to help bail New York City out of its worst fiscal crisis. Prostitution was an easy target and required no extra funding so the Police Commissioner had his precinct Captains set up ‘pussy posses’ to round up as many prostitutes and Johns as possible and charge them accordingly.

Whilst the arrest figures were impressive, it was a victimless crime and perpetrators were back on the street in hours. It also sucked up police resources that could be better used elsewhere. As the precinct Captains had quotas to fill they became inventive as to how they achieved them.

Hence Detective Third Grade Mitchell Clooney was offered an undercover job working nights out of the 41st precinct. But when he turned up he was more than somewhat dismayed at what the work entailed.

“If you don’t like it you can fuck off back to purgatory Clooney; I’m doing you a favour,” Captain Barry Bayson explained.

“You do this on a Probationary Police Officer’s wage; no overtime, and I write you up a good conduct record for when you go in front of the tribunal.”

“You’ll likely walk on the corruption charges with a recommendation from your precinct Captain and I’ll also file a good conduct record signed by the Deputy Chief,” Barry put his feet up on his desk and lit a cigarette.

“But a fucking undercover tranny, Captain? Jesus!” Mitch lit his own cigarette.

“Look Clooney; I gotta quota to meet and a lot of those Johns are sweet on trannies; let’s say you’ll be offering a niche product,” Barry chuckled.

“None of the other guys will touch this detail with a fucking ten foot pole, so it’s this or you’re back being a civilian. Or worse; you’re an ex-copper in the can,” Barry blew smoke at the ceiling.

“Jesus,” Mitch shook his head resignedly.

“Besides, you got the figure, the legs and the ass for it,” Barry coughed as he broke up with laughter.

Mitch Clooney reported for his new duties three nights later. He met up with three female officers from the pussy posse. An old flame of his, Officer Linda Gordon, had taken him under her wing in the preceding days and given him a crash course in crossdressing.

Linda had sat down with Mitch and painstakingly taught him how to apply makeup. She styled and cut his long hair, which he wore centre parted, into a ‘shag’. Mitch’s lithe, feminine, figure was easy to clothe and she put together a wardrobe for him from her own clothes and some cheap lingerie from a department store.

“Tell me again why I have to wear female underwear?” he had asked.

“Well a couple of reasons honey. One is that they are foundation garments, you can’t wear boxers under a miniskirt or hotpants and we need to stuff your bra to give you tits. And two; the Johns expect their ladies to wear sexy underwear and until you can get them to actually solicit you, you can’t arrest them,” Linda explained.

Linda had made Mitch shave what little body-hair he had and then began to dress him, having him do his hair and makeup by himself until he became proficient.

First off she had helped him put on a pair of sheer pantyhose. Mitch had always had a penchant for ladies legs in nylons but was surprised at how delightful the garment felt when he put them on his freshly shaved legs. To his complete embarrassment he became erect.

“Jesus Clooney! Us gals have to wear those fucking things every day, even when we’re wearing pants on the beat. We hate the fucking things but you go and get a fucking boner!” Linda smacked her gum.

“I’ll help you with that, but only because you’re an old flame,” she smiled at him salaciously.

Linda reached out and took Mitchell’s hard cock encased in the sheer pantyhose gusset and tugged on it. Mitch gasped and felt his knees go as the intense feeling of the sheer fabric rubbing on his sensitive penis caused him to orgasm.

A gloop of white semen oozed through the nylon waistband, several globules dripped onto the floor, narrowly missing Linda’s high-heeled pumps.

“Fuck me Clooney, a girl does you a favor and you repay her by coming on her shoes,” Linda giggled.

She snatched a handful of Kleenex from the box on the dresser and held them out.

“Here wipe yourself with these sweetie and tuck that fucking thing under your crotch when it finally deflates,” she said.

Next she helped him into a pair of satin panties, keeping him tucked, and then a matching brassiere which she stuffed with balled-up pantyhose to fill the cups. She helped him in and out of various skirts and blouses, hotpants and tops and finally helped him into a pair of high-heels.

She made him walk in them until he could get around without falling over.

“Ok. Let’s see the finished product,” Linda smacked her gum.

Mitchell stood before her dressed in a black ‘leatherette’ miniskirt, a purple satin blouse, flesh-toned pantyhose, and black high heels. His hair was brushed out, heavy makeup applied, and costume jewellery including drop earrings accessorised the outfit. Underneath he was wearing a pair of full-cut black satin panties and matching bra.

“Jesus! You don’t look half-bad; you could likely pass once you work out how to walk confidently in those heels, and train your voice” she tittered.

“All you need is a female name. The most obvious of course is Michelle.”

And that was why Michelle Clooney was hooking on a cold New York street corner in the winter of 1976. She was into her third week of the month long detail and had assisted in over forty arrests.

But things were about to change; and change significantly.

Michelle was thinking of getting out of her street clothes and getting into a warm bed when a black Cadillac cruised slowly along the street and pulled up against the curb opposite her. The undercover pros were under strict instructions not to get into any vehicles because it would be too hard to follow and protect them. They were to try to get the Johns to park in the alley and bust them there or get them up to the cheap hotel room rented by the NYPD for the duration of the sting operation.

Michelle approached the car as the passenger-side power window slid down. The interior light came on as Michelle leaned in. A handsome, swarthy, well-dressed man sat behind the wheel.

“Get in sugar,” the man smiled at her.

“I don’t think so sir; why don’t you park in the alley over there and I’ll join you,” Michelle gave him a well-rehearsed smile.

The man looked over his shoulder at the dark alley and shook his head.

“I don’t do that. Get in and I’ll take you somewhere nice for the evening and I’ll make it worth your while you pretty thing you,” he grinned again and even Michelle had to admit to herself that this man was very handsome.

“I can’t do that sir; my pimp would not be happy if I left my corner unattended for too long,” Michelle continued to smile.

The man shook his head.

“You ask your pimp if it’s ok for you to go with me some other night. I’ll be back to see you soon sugar; I like what I see. Tell him there’s a C-note in it; half a yard for you and the rest for him. Gotta go babe,” the man closed the window forcing Michelle to step back.

The interior light extinguished and the car drove away with a squeal of tires.

Across the way in a narrow dark alley a patrol car was parked nose-out with its lights out and engine ticking as it cooled. It was the response vehicle that would drive across the street and arrest the Johns in the alley or the burly coppers inside would clamour up to the third floor of the building on the corner where the undercover hookers had a room, and arrest the John there.

One of the police had a pair of binoculars trained on the corner when the Caddy drove up.

“Jesus Christ! Fuck me! Is that Frankie Caputo?” the driver whistled.

The cop in the passenger seat snatched the binoculars off his partner and checked out the Cadillac.

“Jesus! Write down the tags and pass me the PR,” he handed the binos back.

Just as the Caddy drove away Michelle saw the headlights flash across the way, the signal for her or Linda to go into the alley and pick up the PR, police radio, hidden under the dumpster.

Michelle got down on her knees and scrambled around looking for the hidden PR. There was also a holstered service pistol, a snob-nose 38, hidden under the dumpster.

“If I get bit by a rat or shoot myself with that fucking pocket pistol I’m going to cap those cherry top mother fuckers,” Michelle huffed as her fingers scampered and finally found the PR.

“Hey sugar tits, did you see who that John was in the Caddy?” the uniformed cop spoke into the PR.

“Don’t call me sugar tits you fucking donut dunker,” Michelle replied.

“Hey seriously Clooney; we’re pretty sure that was Frank Caputo, one of Lilo Galante’s Captains,” the radio cackled.

“Yeah. Let’s wrap this thing up for tonight and I’ll make a report to the Captain,” the cop said.

He got no grief from Michelle or Linda.

Linda sat in the driver’s seat, taking Mitchell-Michelle home to Linda’s place to get changed. The first couple of nights they had gone back to ‘The House’, meaning the precinct house, and the bored nightshift had tormented Mitchell and hazed Linda dressed as they were like hookers. Disconcertedly, two of the cops had actually come on to Michelle when she was alone in the change room.

“You do look kinda hot Michelle,” Linda smirked around her cigarette.

“Cut that shit out,” Mitchell replied but he had to admit that he was often finding himself aroused wearing the sexy female attire.

Linda sat next to Michelle on the couch; she had poured her another drink. They were both smoking, sitting in the gloom. They had arrived Linda’s at about 3 AM, Mitchell had not bothered transforming from Michelle yet.

“I meant what I said in the car Michelle,” Linda leant into Michelle and whispered in her ear.

Linda’s breath in Michelle’s ear was quite disturbing but also arousing and Michelle was trembling. She leaned forward to ash her cigarette, hoping to disengage a little from Linda but Linda leaned forward with her and crushed out her cigarette and put her hand over Michelle's and made her butt out her cigarette too.

“Cigarette break is over Officer. Time for you to get shifted into your civvies,” Linda snickered.

But Linda didn’t disengage. She slid a hand across Michelle’s lap and dug her fingers into Michelle's upper thigh and she wrapped her free arm around Michelle's shoulder and eased her back onto the couch.

Linda forced her hand further up Michelle's thigh and inside the leg of her hotpants until it came to the V of her panties.

“Mmm you’re wearing your panties over your pantyhose just like I showed you,” Linda nibbled on Michelle's earlobe and Michelle felt herself becoming aroused.

Linda’s fingers grazed the front of Michelle's panties and Michelle gasped and inadvertently opened her legs just a little.

Linda grunted with victory and drove her fingers into Michelle's crotch, then inside her panties and opened the gusset of Michelle’s pantyhose with a sharp fingernail.

“Let me get out of these woman’s clothes,” Michelle said, gasping as Linda explored inside her hotpants.

“I told you I find you really sex dressed like you are,” Linda smiled and squeezed Michelle's growing erection.

“You look absolutely gorgeous. I’ll let you into a secret; I’m bisexual and I love having sex with sexy women like you but you are special because you have a cock and you’re cute. If it’s any consolation if you were a real woman you would still be here with me, being seduced.”

Linda pulled Michelle down on the couch and turned off the lamp so the room was lit only by the glow of the muted television.

The two stunning hookers kissed, their lipsticked lips locked and their tongues entwined. Michelle had surrendered; she saw no point in resistance. Michelle realised that she had not made love to a woman since she had been suspended, so why not take up Linda’s offer?

“Come on honey; why don’t you scratch my itch!” Linda grinned and pulled down Michelle's hotpants.

Michelle kicked the hotpants out of the way and knelt on the couch, her erection proud and rampant. Michelle slipped out her tongue and licked Linda’s slim nylon-clad ankles, taking her feet in her hands Michelle massaged Linda’s calves and sighed. Michelle slid her tongue along Linda’s legs and spent a few minutes teasing the fine wrinkles in her pantyhose at the backs of her knees. Linda shuddered and she twisted her fingers in Michelle's scalp.

“You seem to know what you are doing honey. Hooking seems to have sharpened you skills,” Linda groaned and shucked out of her miniskirt.

Michelle continued the journey up Linda’s elegant legs stopping at the tops of her control-top pantyhose to explore the darker nylon at the top of her thighs. Linda guided Michelle’s face to her crotch and Michelle licked Linda’s mound through her black satin panties and pantyhose crotch. The garments were moist and pungent with her juices.

“Don’t take forever! You know what I want!” Linda pulled aside the gusset of her panties, ripped open the crotch of her pantyhose and forced Michelle’s face into her sex.

Michelle’s tongue explored Linda’s labia and found her hooded clitoris. It was erect and as soon as Michelle licked it Linda pushed Michelle’s face into her groin and writhed against her.

“Ohh!” Linda moaned.

Michelle licked Linda’s clitoris with long slow strokes and gradually increased the speed; her wet tongue lapped Linda’s sex and Michelle tasted her sweet secretions. Linda’s heels were drumming on the couch and Michelle knew she was close to climax. Michelle frantically suckled Linda’s sopping vagina ensuring her tongue teased her clitoris. Michelle grasped Linda’s hips and forced her face into Linda’s sex as she suckled, licked and caressed her.

“Oh god you are good at this you little tranny hussy!” Linda entwined her fingers tightly in Michelle’s hair and forced Michelle’s face into her vagina as she orgasmed.

Michelle licked and sucked Linda to climax and then she slowed down as Linda began to come down from her orgasm. Linda’s clitoris was sensitive after her orgasm and when Michelle continued to lick it, she pushed Michelle's face out of her groin. She pulled Michelle’s face up to hers; Linda’s face was glowing and her mascara was smeared. Linda kissed Michelle; exploring her mouth with her tongue.

Linda opened her legs for Michelle and she slid between them; their nylons rustled as they rubbed together in the dark, quiet room.

“Put it in me Michelle! Fuck me!” she moaned and reached down and placed Michelle's penis at the entrance to her hot wet vagina.

Linda lifted her legs and wrapped them around Michelle’s flanks and pulled Michelle to her. Michelle’s rampant penis slid inside Linda’s warm, moist cunt and Michelle began to slowly fuck Linda.

Michelle's turgid member slid in and out of Linda’s buttery cunt and almost immediately Michelle felt her orgasm approaching. Linda was coming again too; she panted with lust and desire, her sweet breath huffed in Michelle’s ear, whispering obscenities as she drummed her heels on Michelle's back to encourage her to fuck her harder. Michelle emptied her seed deep inside Linda; she ground the base of her penis against Linda’s pubis, stimulating her clitoris.

The two lovely pseudo-hookers rutted and fucked against each other, whispering obscenities in the dark until they were both sated.

Michelle kissed Linda and held her close until she became aware that Linda was struggling beneath her.

“Time for you to transform back into Mitchell and go the fuck home,” Linda grinned in the gloom extracting herself from underneath Michelle.

Mitchell walked the few blocks to his apartment feeling very content but also very confused. He was worried that he kind of really liked transforming into his alter ego Michelle. The clothes were sexy, the shoes were sexy, the makeup was sexy, he had mastered the art of walking and talking like a woman and Goddamit, Michelle was sexy! And if Linda found Michelle sexy she could certainly keep going back for more.

Mitch felt like a woman when he was Michelle. It was baffling.

The next morning things were no less bewildering. Mitchell was summoned to the precinct house and found Captain Barry Bayson and a gentleman who could only be FBI by the cut of suit and the cut of his hair sitting in the small conference room. Linda Gordon was also sitting at the desk, dressed in neat civilian attire.

“Sit down Clooney and let my learned colleague from the Bureau give you the 101 on the New York Mafia,” Barry did not look happy that a FBI agent was in his house.

The agent began without any introduction.

“Carmine ‘Lilo’ Galante, Joe Bonanno’s former underboss, recently took control of the Bronx with no backing from the Commission, becoming de facto street boss. Frankie ‘The Stallion’ Caputo is one of his Captains,” the agent read from a notebook.

“Frankie makes good money for Carmine, especially from his nightclub and the high class brothel he runs. NYPD Vice has been tracking Frankie for quite a while but they don’t have the resources to make a case and pinch him,” the agent explained.

“Oh I get it. We pinch him for solicitation in the little sting we got running down at Hunts Point,” Mitchell smirked.

“Shut the fuck up Clooney and let the man finish,” Barry snapped.

Linda kicked Mitch under the table and gave him a stern look.

“That would serve no purpose Detective Clooney. We want a lot more from him than just a soliciting pinch, and you just might be our in,” the agent stared at Mitchell.

He dropped a couple of Polaroids on the table. They were of Mitch dressed as Michelle, looking hot and sexy and working her corner.

Mitch blushed.

“He likes you,” the agent said matter of factly.

“Or more correctly; he likes her,” he pointed at the pictures.

“Frankie’s street name is ‘garanhao’, which means stallion or cocksman, and he likes to sample his wares,” the agent explained.

“Sample his wares?” this time Linda asked the question.

The agent blushed.

“He likes to err; he likes to err; what the hell…he likes to fuck his stable of whores,” the agent’s face was red with embarrassment.

“Let’s get back to why you are here. You want me to somehow entrap this Caputo guy but not pinch him for solicitation? How the fuck would that even work?” Mitch looked at the agent and then at his Captain.

“Look the NYPD is just about broke but the FBI has been successful recently prosecting cases under the new Racketeer Influenced and Corrupt Organizations act; we call it RICO. We get to keep some of the proceeds of crimes committed under RICO so the FBI’s organized crime division can mount investigations that local law enforcement can’t afford,” the agent explained.

“I still don’t get it?” Mitch looked around the room shaking his head.

“Jeez Mitch how dumb can you be? The FBI wants you to go undercover as Michelle and get incriminating information from Caputo and feed it to the Feebs,” Linda sounded exasperated.

“No fucking way! Not happening! Jesus Christ no!” Mitch kicked back his chair and stood up, agitated.

The agent remained cool and dropped a series grainy black and white photographs on the table. These pictures, although poorly lit, were undoubtedly of Detective Mitchell Clooney. In the pictures he was receiving money and cocaine from known drug dealers.

“Hey fuck that man! I was doing my job, making a buy to bust a drug dealer,” Mitchell whined.

No one in the room was buying his story and he knew it was bullshit.

“You really wanna run with that Clooney? I figure we can get you five to ten in a Federal Penitentiary. You know what they do to cops in those places?”

“You worried about wearing a skirt and nylons and playing up to Frankie Caputo? Those white supremacists and gangbangers are gonna have you sucking dick for dinner every day,” the FBI agent chuckled.

“Shit…You remember Blake Newman? No? We put him away in Folsom prison but tried to keep his identity as a former police officer secret. His cellmate found out that he was an ex-cop and invited him to play mommies and daddies and when Newman refused, his cellmate knocked out all his teeth. He told the rest of prisoners that he has a new cell-mommy, and shit, with no teeth in the way his cock slides in her mouth just nicely,” the agent sniggered.

Mitchell paled and his knees buckled. Linda got up and helped him back into his seat.

“You FBI guys are fucking assholes! You gonna let him get away with this Captain?” Linda slammed her palm down on the table.

Captain Barry Bayson just shrugged. He looked defeated.

“What your Captain is trying to say is that he no longer has control of this investigation and if we start digging I reckon we will have half this precinct up on corruption charges.”

“He’s already agreed to seconde Detective Mitchell Clooney to us for an indefinite period. During that time Detective Clooney will be reinstated on full wages and his pension payments will be doubled. He will receive other stipends and recompenses as necessary to maintain an undercover identity,” the agent grinned.

“Why are you telling me all this?” Linda looked from her Captain to the FBI agent.

“Because you too are seconded to my task force; you will be the conduit from the FBI case managers to Miss Michelle Clooney, who from this day forth shall use only that name and that persona.”

“We will have a full set of good quality false identification documents ready and a backstory for Michelle to become conversant with.”

“You two will continue to operate as undercover prostitutes, not for the NYPD but for the FBI. I don’t expect you to actually service any John’s of course; you are there only to try to ingratiate Michelle with Frank Caputo,” the agent was again reading from a file in front of him.

“I don’t get any say!” Linda looked at her Captain who shook his head.

“What about me! You want me to live full time as a transvestite hooker and somehow get into a relationship with a dangerous wiseguy and feed you incriminating information about the New York Mafia? What the fuck?” Mitchell ranted.

“You got it sugar. Anything you can get from any possible source, from overheard conversations to pillow talk,” the agent grinned.

“Pillow talk?” Mitch was astounded at the implication.

To be continued

Pillow Talk
By
Michele Nylons

Chapter Two – Tranny 101

Michelle Clooney sat in a booth in a rundown coffee shop near Times Square. The grimy window provided views of go-go bars, sex shops, peep shows and adult theatres, the iconic square had not improved any since it’s setting for Midnight Cowboy a few years earlier.

Michelle was dressed in red spandex hotpants, a long sleeved purple satin blouse, her ‘go to’ short faux leopard-skin fur jacket, red ‘fuck-me’ pumps, glossy flesh-toned pantyhose, heavy makeup and gaudy costume jewellery. She was required to remain ‘in character’ to maintain her undercover persona as a New York streetwalker.

Sitting opposite her dressed in black micro-miniskirt, red satin blouse, black leather jacket, black fishnet tights and black high-heels was Linda Gordon. She was also wearing heavy makeup and also working undercover as a prostitute.

Incongruent to the two hookers were the two be-suited, high-and-tight coiffed gentlemen sitting beside them.

“You know you two guys look exactly like G-men. You stick out like dog’s balls,” Linda smacked her gum.

“Or we could be a couple of businessmen johns trying to pick up hookers,” one of the men grinned.

“Well you could be brothers, except one of you is white and the other is a black,” Linda fired back.

“I fucking hate this detail. I’m still not sure I’m going through with it,” Michelle lit a cigarette without offering her pack to anyone else at the table.

She tapped her Bic lighter agitatedly on the formica table.

Linda put her hand over Michelle’s to stop the irritating ticking noise.

Once again the FBI agent produced the Polaroids of Michelle parading in her skank clothes on her Hunts Point street corner.

“When we put you in the pen and these pictures of you turn up, like things always seem to do in prison despite the security, you’re going to be a cellblock favourite.”

“I bet those Hells Angels, White Supremacists, Black Panthers and Latin Kings are gonna fight to see who gets to own you. They just need to smuggle in some nylons, makeup and fuck-me shoes and put you to work. Those boys gonna line up outside your cell night and day. Your asshole gonna get more in and outs than the Sedgwick Avenue Car Park,” the black Feeb sniggered.

“You gonna have more semen in you than a US navy aircraft carrier,” the two FBI agents high-fived each other over the table.

“Ok, ok I get it. You know I’m in,” Michelle began to tap her lighter again.

Linda glared at her and she stopped.

“Ok we gonna make this quick. This is the last time you gonna see us like this; from now on we only contact Miss Gordon,” the white Feeb nodded at Linda.

“In this envelope is a Nebraska State driver’s licence and a social security card in the name of Mitchell Clooney. We decided not to change your male name but the documents won’t lead back to you as a cop. Instead they will confirm your backstory, which is also in this envelope, and which you need to learn by wrote ASAP. Got it?” the Feeb pointed at the buff envelope.

“To summarize. You left Nebraska at sixteen and came to New York when your gender identity disorder became overwhelming and your parents threw you out for dressing like a girl. You’ve been working on the streets since you got here and your friend Linda here took you in yada, yada, yada.”

“There is a set of keys for your apartment, five hundred dollars in cash and a bankbook into which we will deposit money every month.”

“Any and all information that you get from Frank Caputo gets funnelled to us through Linda here right?” the black Feeb raised his brows and Michelle nodded.

“Also I must warn you that you cannot commit a crime whilst you are working under cover, there is no legal clemency” the white Feeb grinned, indicating that he fully expected this directive to be ignored.

“Look Michelle. The deal is you do whatever you gotta do to get as much information as you can from Frank about the mob; we’ll decide what’s useful and what isn’t. We will pull you out when we decide we have enough information or when the investigation has run its course…”

“Or your cover is blown,” the black Feeb interjected.

“Whatever the fuck! When it’s over with you walk away Scott free, reinstated back as an NYPD detective and your record and indictments expunged ok?” the white Feeb finished his lecture.

Michelle nodded again.

“Ok. Good luck princess; we’re outta here. We got a friend of ours coming to talk to you about a few things so don’t go anywhere,” the two Feebs extricated themselves from the booth and walked away.

“Fuck!” Michelle crushed out her cigarette and immediately lit another.

Linda had just finished ordering coffee from the waitress when a tall, attractive black woman wearing pink bell-bottom pants, platform shoes and sporting a huge Afro walked up to the booth.

“I’ll have a cup too honey. Black, strong and sweet, just like I like my men,” she chuckled.

Her voice was smooth, vibrant and sexy. She slid into the booth uninvited and beamed a smile at Linda and Michelle.

“You must be Linda and you gotta be Michelle,” she chortled.

“I’m Latisha and I’m here to give you the 101 on how to be a tranny.”

“Really? The Feebs pay you to teach crossdressing?” Michelle baited the attractive black woman.

“Look sugar; I’m sure your friend Linda here has provided you with good advice so far. Shit you look good girl! But there is more to being trans than just wearing lipstick, powder and a skirt,” Latisha replied.

The waitress came back with their coffee and conversation paused while they drank.

“Ok Michelle; you looking good, nice and femme but still obviously a tranny to those who know what to look for. Don’t worry that’s not a bad thing; you ain’t trying to be a woman per se, you trying to be a very feminine transvestite,” Latisha said.

“Ok sugar; lets take the contents of that envelope out for a ride,” Latisha stood and Michelle and Linda followed suit.

They walked to Grand Central then took the ‘muggers express’ as the subway was referred to by many, to Hunts Point Avenue and then walked the few blocks to apartment that the FBI had rented for Michelle.

“Jesus! What a fucking dump!” Michelle uttered.

The single room apartment was three flights up a dingy staircase and was sparsely furnished with rummage sale furniture. The one thing about it was that it was clean.

“What do you expect girl? You supposed to be a street walker just making ends meet not some high class Manhattan escort,” Latisha threw her large carry bag on the ratty lounge.

“Ok we gonna get personal now. You sure you wanna stick around for this?” she asked Linda who nodded, fell into the single overstuffed armchair and lit a cigarette.

“Yeah. I wanna see the show,” she grinned, blowing smoke across the room.

“Ok strip baby,” Latisha ordered.

She went over to the small stove and began to heat up some water and then rummaged around in her bag and laid out various items on the scarred wooden table.

Michelle stood naked in the centre of the room. Her skin was pale, smooth and relatively blemish free, her body supple but with an ample bottom and long well-formed legs. Mitchell had often been teased that he had a ‘girly’ body and even when he tried working out at the gym he failed to develop much in the way of musculature.

“Oh we can work with this; just a few adjustments here and there and you be fine,” Latisha deliberately used street talk.

She held up a pink and gold rectangular cardboard box with the word ‘Neet’ printed on it.

“This is a depilatory cream and it removes hair. It does a great job but you don’t wanna get any on your dangley bits,” she joked.

Latisha took the tube out of the box, squeezed some of the foul smelling cream onto her finger and spread it in the crevice of Michelle’s buttocks and under her groin being careful to keep it away from her scrotum.

“We just gonna use it in those hard to get to places, you can shave everywhere else. Of course you can use this anywhere you have hair if you like, but it ain’t cheap,” Latisha explained.

Michelle was shocked. This stranger was touching her in the most intimate of places having only met her just over an hour ago. But Michelle knew better than to question any FBI mandated procedures.

“Ok while that does its thing lets get the rest of you done,” Latisha poured hot water into a bowl and took out shaving soap and a safety razor.

She carefully shaved Michelle’s scrotum and pubic hair then worked her way around her body shaving away any hair that Linda had missed when she first helped Mitchell crossdress. Then she used a warm face cloth to wipe away the Neet, showing Michelle all of the hair it had removed. She gave Michelle’s legs another shave.

“How does that feel?” Latisha asked.

“I have to admit that my skin feels like its glowing; it’s quite sensual,” Michelle conceded.

“You look good honey,” Linda chimed in.

“You need to do this about once a week to keep those horrible hairs away,” Latisha instructed.

“Ok. Those nasty eyebrows gotta go,” Latisha picked up her tweezers and went to work.

Next she bushed out Michelle’s shag hairdo and worked on it, improving the shape and straightening the bangs.

She gave Michelle a manicure. Mitchell had favoured long nails even as a man so all Latisha did was shape them, buff them, and apply two coats of cherry-red nailpolish.

“Ok let’s take a break while you fix your makeup,” Latisha broke out her Vagina Slims and lit up.

Michelle fixed her makeup; she was quite adept now that she had been doing it every day for nearly a month.

“Ok. Now we getting to the nitty gritty. You ain’t doing to bad a job tucking but you still got an unsightly package bulge down there,” Latisha pointed to Michelle’s groin.

“Ok you feel under there?” Latisha had boldly put her fingers under Michelle’s groin.

Michelle placed her fingers there and located the inguinal canals where Latisha had her fingers.

“You push those suckers back up where they came from. Do it gently and stop if there is any pain,” Latisha instructed.

To Michelle’s amazement she was able to push her testes up into her body leaving her scrotal sac empty. Latisha showed her how to wrap the sac around her penis and push them back between her legs. She used a piece of surgical tape to keep the tuck secured.

Michelle slipped back into her pantyhose and panties and was delighted with the result. She had a smooth appearance with no evidence of any genitals.

“I’ll be fucked,” Linda grinned.

“You wouldn’t even suspect that you had a cock.”

“And if you don’t have tape; or you want to be able to use that thing, just tuck it under and use your pantyhose and panties to hold it in place until you need it,” Latisha grinned and patted Michelle on the front of her panty.

“Ok girl, you can get dressed now but the last little helper I got for you are these breastforms; they basically rubber titties for you to fill the cups of your bra. I got you a B cup based on the information I was given and they seem about right. You don’t wanna be walking around looking like Mae West; you wanna have titties appropriate to your body size and you are a petite thing; well for a man you are anyway. You can use that surgical tape or just push them into your bra cups honey.”

“Now we gonna spend some time teaching you to walk and talk. Once again my girl Linda has made a great start but I’m gonna put some polish on it,” Latisha grinned.

The three women spent a few hours helping Michelle improve the way she walked and working on her voice. After considerable effort Michelle developed a smoky feminine voice that she could maintain with little concentration.

“I don’t understand why I’m doing all this shit,” Michelle said when she became frustrated during the training.

“Because your backstory is that you’ve been living as a woman for ten years and all of ‘this shit’ as you put it, should be second nature to you by now,” Latisha explained.

Linda went down to the liquor store and bought back a bottle of Jack Daniel’s, some coca-cola, a bag of ice and a carton of cigarettes. She dumped the ice in the sink and mixed drinks for everyone.

They lit cigarettes and sat down to talk.

“Now we come to the good bit. Sex,” Latisha grinned.

Michelle paled.

“Jesus do we really have to?” she whined.

“When Frankie sees a fine lady like yourself, he’s gonna want to give you some loving sugar, so best you listen up,” Latisha went on.

“Now fellatio is pretty easy, you had it done to you plenty I’m guessing you just do the same to him what feels good to you. Use your lips and on the shaft and your tongue on his head baby and you can’t go wrong,” Latisha sniggered.

Linda laughed too but Michelle glowered at the two women.

“Ok. What I’m gonna talk about ain’t nice but it’s essential.”

“You gonna have to douche or enema your ass before you do any fucking. I recommend that you take an enema late afternoon and that will keep you clean for rest of the evening. Swallow a couple of Imodium as well to soak up any water that don’t escape,” Latisha explained.

“Jesus no!” Michelle scowled.

“If you caught on the hop you can just douche with this bulb thingy. It will work for the sort term but you don’t wanna plan on a long night’s fucking,” she chuckled again.

Latisha laid a full enema kit and a small rubber douche on the table.

“You’re gonna have to get used to using these,” she pointed at the objects that Michelle couldn’t bring herself to look at.

“Look honey; anal sex can either be very painful or very pleasurable, it’s up to you. The likelihood of you having to fuck this guy is high so you might as well hear what I have to say,” Latisha said.

“You make sure you are clean and always carry lube,” she pointed to the tube of KY jelly.

“When you think you’ve used too much; that means you’ve used just enough.”

“Make him take his time and don’t let him penetrate you until you are ready and try to get him to stimulate your prostate with his dick while he’s fucking you. When he does that you gonna get to like what he’s doing,” Latisha grinned.

Michelle blushed and squirmed throughout the lecture and was glad when Latisha had finished.

“That’s all I got for you honey. Good luck,” Latisha got up to leave.

“Hey wait a minute Latisha. Are you FBI or what?” Linda asked.

“Shit no woman! I’m just a nice black trans lady that got paid by some nice gentlemen to teach miss peaches and cream here how to be a polished transvestite,” Latisha chuckled.

“Those two G-men gave me just enough information for me to do my job and from what I can grasp of the situation, I don’t wanna know any more,” Latisha made her way to the door and let herself out.

“Shit! Shit! Shit!” Michelle griped.

“Well if nothing else honey at least you learned how to tuck. Looking at you in those hotpants now I’d swear there was a cunt in there,” Linda cackled.

She managed to duck under the tube of Neet that Michelle threw at her head.

Michelle and Linda worked three more nights on the corner, turning down the johns, until finally Frank Caputo tuned up again in his big black Caddy.

Michelle approached the vehicle with some trepidation. Frank Caputo, a handsome swarthy man dressed in an expensive suit, sat behind the wheel.

“Hey you look hot tonight honey; you wanna come for a drive,” he smiled at Michelle.

Michelle was visibly shaking as she opened the passenger door. She looked over at Linda who gave Michelle a nod; ‘it’s going to be ok’.

When she sat in the bucket seat Michelle's miniskirt rode up exposing her thighs. This was not lost on Frank who took an eyeful before Michelle could pull down the hem of her skirt.

“So your pimp gave you the ok then?” Frank grinned.

“Sorry…what?” Michelle was scared and confused.

“You told me last time that you couldn’t come with me because your pimp wouldn’t let you leave your corner unattended,” Frank pulled away from the curb.

“Oh. Oh that. That’s just something us girls say when it’s close to quitting time and we don’t wanna leave the corner. To be honest, I don’t really have a pimp,” Michelle started using her backstory.

“Really? You’re a free agent?” Frank checked the rear vision mirror habitually.

“Well me and my friend Linda look out for each other,” Michelle replied, sticking to her story.

“So you’re like a collective? You support each other. It’s sort of like the thing I’m into,” Frank laughed and Michelle couldn’t help but laugh with him.

His outgoing friendly, flirtatious demeanour was enticing even though she had only just me him.

He placed a hand on her knee and squeezed.

“You got a great pair of pins honey,” he stroked her leg, working his hand up her thigh.

Michelle stiffened and wedged herself against the door. Frankie could see the fear in her eyes.

“You’re behaving awful coy for a woman in your line of work,” Frankie looked at her questioningly.

Michelle knew she had to be careful so she decided to interweave fiction with fact.

“Well I am a little scared. I don’t usually get into cars with customers but I’m also scared because I know who you are,” Michelle replied demurely.

Frank Caputo gave out a belly laugh.

“So tell me; who am I?” he chuckled.

“You’re Francis Caputo,” Michelle whispered.

“Jesus nobody but my mother calls me Francis. And what do you know about me?” he beamed a beatific smile at Michelle.

“That you’re connected; very important, and not to be fucked with,” Michelle replied.

“All true. But also I’m a gentleman, generous, and unlike some, I treat special ladies like yourself courteously and with dignity,” he squeezed Michelle’s knee gently.

“We’re here,” Frank pulled over outside of a brightly-lit façade.

“Where is here?” Michelle was intrigued.

“I told you when we first met that I’d take you somewhere nice. You ain’t exactly dressed for dinner so this will have to do,” he pointed to what Michelle realised was a nightclub.

Frank got out of the car and assisted Michelle out of the passenger door, helping himself to an eyeful of thigh as her miniskirt rode up. A flunky in a suit raced over from the doorway and took Frank Caputo’s keys so he could park his car.

“Don’t be afraid; I own this place. Nobody is going to do or say anything bad to you,” Frank took Michelle’s arm in his and smiled at her.

Michelle had to admit that she had never felt so feminine; she had completely let go of her male alter ego. She wasn’t sure if it was a defence mechanism so she could deal with the current situation or if she genuinely liked being Michelle this very moment. She decided not to explore the subject too deeply, just in case the answer scared her.

The next few hours were dizzying. Frankie escorted Michelle into the nightclub and every patron they passed greeted him with deference. They were led to a small booth where they had privacy but could see into the nightclub and see the performers on the small stage but they were shielded from prying eyes.

Frank seated Michelle first and then he slid in beside her. Michelle started to tremble again as she was hoping he would sit across from her.

He ordered champagne from the waiter and then they were left alone. Frank had returned his hand to Michelle’s knee and was lazily stoking her leg.

He leaned in to kiss her and Michelle pulled away shocked.

“I’m sorry. I know you working girls don’t do that with johns but I was hoping this could be more like a date or something,” Frank blushed and apologised.

Michelle realised the gaff she had made. She needed to establish a relationship of some sort with Frank to get the information she needed from him. She set her resolve and cleared her mind of all other thoughts.

Michelle leaned into Frank and pressed her lips to his then pulled away.

“No. I’m sorry. You’re right. This is a date…or something,” Michelle gave Frank a brilliant smile her white teeth framed by her bright red lips.

She looked beautiful in the subdued light of the nightclub and this time when Frankie leaned in to kiss her, Michelle did not move away.

Frank put his arms around her and pulled her to him and Michelle allowed herself to become compliant and yielding. He slipped his tongue into Michelle’s mouth and at first she remained docile, but she soon began to respond.

Being in the embrace of this powerful man who was kissing her passionately whilst caressing her and treating her with deference whilst obviously smitten with her raised some peculiar reactions and responses.

There was no doubt that’s she still felt a little fear but there was none of the revulsion that she had expected. Instead Michelle actually felt a growing sense of femininity and a budding ardour.

Michelle reciprocated and wrapped her arms around Frankie and slipped her tongue into his mouth. Frankie squeezed her tighter and Michelle felt her desire begin to inflame and a newfound enthusiasm for her involuntary womanhood.

Frankie was sliding a hand under her skirt, which Michelle found a little brazen, when the waiter returned with a champagne bucket and stand, two crystal glasses and pristine white napkins.

Frankie and Michelle broke their kiss. Michelle was breathless and thankful that the waiter had arrived as things were getting a little uncomfortable for her.

Frankie kept an arm around Michelle’s waist and she slid her hand into his lap and patted his thigh to let him know all was well.

They drank champagne and smoked, chatting during the breaks between the stage acts. Frank was an engaging conversationalist as well as attentive to Michelle, ensuring the conversation wasn’t just about him. This gave Michelle the opportunity to spin her backstory.

“It’s a shame that someone as beautiful, refined and admirable as you is forced to do what you do?” Frankie smiled.

“You hardly know me Frankie; I’m hardly refined and how do you know I’m admirable?” Michelle blushed; the champagne was going to her head.

“I can just tell you have good heart,” he gave her that smile again and Michelle melted.

This time it was she who leaned into him for a kiss. They kissed passionately and Frankie became very brazen and slid his hand all the way under her skirt and rested it on the front of her satin panties.

Michelle was glad that Latisha had taught her how to tuck properly but she could feel herself becoming turgid. It was a little uncomfortable but manageable.

Frankie took Michelle’s hand and placed it in his lap.

He was erect and Michelle could feel the outline of his tumescence through his trousers. Instinctively she gave it a squeeze and was rewarded with sigh and the feel of the cock pulsing in her grip.

Michelle had come this far so she set her resolve and pushed herself along the slippery slope that would eventually lead to her having to satisfy this man one way or the other. She explored Frankie’s mouth with tongue and stroked his erection though his pants; masturbating him while she kissed him passionately.

Frankie was becoming very excited, gasping in Michelle’s mouth and pawing at her panties. He placed his hand on hers and directed it to his fly.

The moment of truth!

Michelle undid Frankie’s fly and tentatively put her fingers inside. She could feel the heat through his silk boxers and then her fingers found his long, thick, sleek penis. She freed it from his flies and hefted it in her hand. It was quite substantial.

Frankie was kissing her fervidly and holding her tight. He wriggled his hips encouraging Michelle to work on his penis.

The skin on the shaft of Frankie’s penis was very smooth and sleek whilst the bulbous head was leaking copious amounts of pre-ejaculate. Michelle used the slick viscous fluid to lubricate Frankie’s cock as she slowly began to stroke it. She squeezed it as she did and ran her thumb over the glans and tickled his sensitive fraenulum.

Frankie’s fingers crept further up her thigh, his soft fingertips caressing her nylons. He found the front of her panties and began to stroke her between her legs. She opened her legs wider to give him access.

Masturbating Frankie was not the abhorrent, disgusting task that she thought it would be. It was quite empowering having this man beg her for release. Frankie was rubbing Michelle between her legs and his fingers pushing her pantyhose and panties against the shaft of her penis was causing her to become tumescent too. She wondered if the surgical tape would hold.

Latisha had only recently shown Michelle how to gaff her penis between their legs using a strip of surgical tape and her pantyhose and panties to hold it in place but as Michelle became erect this method was exposed for its inadequacies and her phallus sprung from between her legs. Frankie teased it though the layers of nylon and satin.

Michelle gasped and kissed Frankie ardently.

“Hmm that’s nice Frankie,” Michelle smiled at him using her thumb to tease a globule of pre-seminal fluid from his glans and work it into the sensitive flesh of his penis.

They kissed again, harder and with more intensity as they squeezed and stroked each other’s cocks.

Michelle gasped with pleasure as Frankie gripped her throbbing member through her panties and squeezed and caressed it. Her knees began to shake as she felt her orgasm approaching. She pushed his hand away; although she was enjoying Frankie’s ministrations immensely she wanted to concentrate all her attention on pleasing him.

They continued to kiss and caress and Michelle worked Frankie’s cock, alternatively feathering her fingers along the shaft and then gripping it and stroking it. She felt his cock begin to pulse and throb and fully expected him to ejaculate under the table into her hand.

“I don’t want to come way,” he whispered in her ear and then kissed her again.

Michelle was puzzled until Frankie broke the kiss and placed his hand on her shoulders and pressed down.

Michelle realised what he wanted. She was highly aroused and feeling so very feminine but still trepidicious. This was a line that once she crossed, she could not return; but she had known for some time now that this was inevitable. She trembled as she slid out of her seat and crawled under the table and then put her head in Frankie's lap.

Michelle looked up at Frankie he looked down at her pretty face.

“God you are gorgeous,” he smiled down at her.

Michelle braced as she realised she was about to perform fellatio for the first time. She had been on the receiving end many times so she knew what was expected and she opened her mouth and was prepared to do her best.

Frankie placed his hands each side of her face and guided her to the huge erection jutting from his pants.

Michelle gagged as Frankie’s glans rubbed against her tongue and his shaft slid in and out of her lips. Frankie looked into her pretty face and eased Michelle’s mouth up and down on his cock. He moaned as she sucked his turgid penis. Glancing down he could see she was fighting the urge to gag. But god she looked pretty with his cock in her mouth.

“Oh honey; please finish what you started. I have never been so infatuated and so hot for a woman like you before,” Frankie moaned.

Once she had got over the dread of taking a cock into her mouth and adjusted her breathing so that she could ingest Frankie’s resplendent member, suck on it and not gag, that feeling of empowerment washed over her again. She was in control and Frankie was begging her to please him.

Michelle suckled the hard pulsing member invading her virgin mouth; she didn’t feel defiled. She felt powerful; she was the object of Frankie’s desire. She raised a hand to hold the shaft of Frankie’s hard cock so she could suckle and lick his glans without gagging. She couldn’t believe she was getting hard again inside her panties.

Frankie thrust back and forth and Michelle took away her hand so she could accept all of Frankie’s cock into her mouth and she sucked and slavered at the girth of his rigid phallus. She could feel it begin to palpitate.

Michelle could sense that the Frankie was close to climax as he groaned and held her head tight is his hands whilst thrusting his invading manhood in and out of her mouth. She looked up and transfixed him with her eyes as his groin pushed against her face with quicker, shorter thrusts. His penis seemed about to burst in her mouth.

As she sensed Frankie’s climax approach she could feel his penis swell, the tautness of his cock was palpable as it trembled, close to ejaculation.

Michelle suddenly felt Frankie’s penis spasm and his semen ejaculated into her mouth. She controlled her gag reflex as she swallowed the issue erupting from the convulsing organ. His spend tasted warm, salty, bittersweet, and musky. It was not unpleasant.

“Oh my god you’re beautiful!” Frankie moaned as he filled Michelle’s mouth with his seed.

When Michelle sensed he had finished coming she sucked and licked his glans until he was drained and then she got to her feet on shaky legs.

“Thanks babe that was great. Here, clean up,” Frankie offered her one of the pristine white napkins while her took the other and wiped at his crotch.

Michelle took a big sip of champagne to wash away the taste of Frankie’s semen. She adjusted herself, tucking herself back into place, smoothing her skirt and then she sat down, took out her compact and began to fix her makeup

This was not lost on Frankie as he dropped down beside her.

“Don’t you like the taste of my cum,” he grinned at her.

Michelle blushed.

“I don’t usually swallow,” she said.

The deceptive response came to her in an instant; besides she wasn’t really lying was she?

“Don’t; worry babe; I’m glad you drank some wine to wash away my cum, now I can kiss you again,” Frankie grinned and leaned in and did exactly that.

“So you know who I am and what I do. You haven’t asked how I can get away with being out publicly with a Femminiello, a tranny to use the derogatory,” Frankie smiled at her.

“I just figured that you are so powerful that you can do whatever you like,” Michelle replied demurely.

“Hey! Beautiful and smart! You hit it right on the head babe. I’m a Captain so nobody except the boss can tell me what to do or who I can take as my goomah. And Lilo doesn’t care how many Femminielli I go with, as long as I’m a good earner and I kick up to him,” Frankie clapped his hands to get the waiter’s attention.

Michelle was getting a little insight as to who Frankie was, confirming what the Federal agents had told her. She had been briefed on some of the Mafia terms and knew that a Femminielli was a trans woman but she was surprised that Frankie had used the term goomah, an Americanism of the Italian ‘comare’ meaning ‘godmother’ but mobster slang for mistress or girlfriend.

“So is that what I am now Frankie; your goomah?” Michelle giggled and jabbed him in the ribs teasing him.

The waiter appeared and Frankie ordered food and wine. Then he turned back to Michelle and took her in arms and stared at her seriously.

“Hey; you behave yourself and keep yourself just for me and you might be my goomah Michelle,” he kissed her and then released her.

He pushed a fistful of money into her purse.

“You take that. I’m not paying you for sex; that is a gift from me to you. I gotta have dinner with one of my guys to discuss some business so I’ll have Salvatore drop you home.”

“You use that money to buy some nice clothes and I’ll pick you up tomorrow night at eight. We’ll have dinner together and I’ll explain to you what it means to be one of my girls. But I tell you this; you’re finished on the streets,” Frankie kissed Michelle long and hard and then stood to let her out of the booth.

He kissed her again quickly and then a large man in a black suit, who had to be Salvatore, arrived and took her gently by the elbow and led her away.

To be continued.

Pillow Talk
By
Michele Nylons

Chapter Three – Compromise

Michelle called Linda the next day and she came around to Michelle’s place and Michelle told her all about the previous evening except for having to give Frankie a blowjob.

“You ain’t telling me everything are you?” Linda teased.

“I don’t know what you mean,” Michelle blushed.

“You telling me Frankie ‘The Stallion’ Caputo had you all alone in that private booth and didn’t do any more than kiss you?” Linda beamed.

“Well he felt me up too,” Michelle’s cheeks reddened further.

“Bullshit! What else did he do?” Linda squeezed Michelle’s fingers and looked inquiringly into her eyes.

“Well I might have blown him a little bit,” Michelle grinned nervously.

“Oh my god sister! You sucked your first cock!” Linda broke down into a giggling shambling mess.

Michelle glowed a bright crimson and then broke down too and they both lay on the rug laughing uncontrollably. When they finally got their wits together they sat up on the lounge and Linda took Michelle’s hands in hers.

“Seriously. Was it ok? Are you alright?” her affection for Michelle evident on her face.

“It was strange at first but I actually found it empowering not degrading. I have to tell you a secret Linda. I really like being Michelle. I mean I really like it. I don’t feel like Mitchell anymore; he’s a distant memory. I feel so feminine; I mean like all the time. Am I a total faggot?” Michelle had tears in her eyes.

“Oh honey; I don’t think of you as Mitchell anymore either. You’re my girlfriend Michelle,” Linda brushed away Michelle’s tears and kissed her on the side of the mouth.

“You need to be careful with this guy Michelle; he’s dangerous. I know you gotta milk him for information but please don’t put yourself at any more risk than you have to babe,” Linda stroked Michelle’s hair.

Michelle felt so safe and secure when she snuggled up to Linda. Linda was so attractive and her full breasts pressed against Michelle; she breathed in Linda’s perfume and sighed.

Michelle looked into Linda’s eyes and softly kissed her. Linda kissed her back; chastely, just lips on lips.

Linda stroked Michelle’s forehead, flicking her fringe out of her eyes.

“I love you as a friend Michelle; but I find you really sexy too,” Linda cuddled Michelle.

“I love you too as friend. But I still think you’re hot,” Michelle giggled.

They kissed for a long minute and at some stage they both realised that if the kiss continued it would no longer be a chaste, friendly kiss. They both felt their hunger stirring. Just before the point of no return, Michelle broke the kiss.

She looked searchingly into Linda’s eyes and saw the same questioning gaze.

Michelle lowered her face to Linda’s and kissed her passionately; sliding her tongue into Linda’s willing mouth. She tasted like lipstick and cigarettes.

Linda had had a couple of lesbian encounters in her formative years and that’s when she discovered that she was bisexual and of course she and Michelle had already had sex at Linda’s place. But that time it was hurried and the fucking was hectic and not altogether satisfying. This time Linda intended to enjoy Michelle to the fullest.

Michelle’s kisses were soft and sensual; the need restrained. There was no necessity to rush and they explored each other’s mouths with their tongues and caressed each other, taking their time.

They were both identically dressed in miniskirts and satin blouses and Linda pressed her bosom against Michelle’s through her white satin blouse.

Michelle bought her hand up to Linda’s bosom and stroked her breasts though the silky material. Linda gasped in her mouth and Michelle felt Linda’s nipples harden through her blouse and bra. She undid a button and snaked her hand inside Linda’s blouse and found her ample breasts cupped in a lace bra, warm, soft and inviting.

Linda reciprocated and slid her hand inside Michelle’s blouse. She found Michelle’s breastforms and ripped them out their cups and dropped them on the floor. This left Michelle’s meagre bosom encased in a satin and lace brassiere; Michelle’s small breasts were smooth and her nipples hard.

“I want to feel your skin honey; not those plastic tits,” Linda whispered into Michelle’s ear.

Michelle nodded and pulled Linda closer.

They kissed and caressed each other, slowly unbuttoning each other’s blouses and then discarding the garments so that they were both dressed only in skirt and bra. They pressed their warm flesh against each other’s bodies and gasped with lust.

Next to go were their brassieres; dropped on the floor. Linda’s ample bosom pressed against Michelle’s meagre breasts and they pulled each other close and opened their mouths wider as they kissed and flicked their tongues together. This was so gentle and so feminine.

Linda led Michelle over to the ratty sofa and instinctively Linda lay down with Michelle astride her. She raised her head and suckled Michelle’s small breast and Michelle gasped with pleasure. Michelle held Linda’s face to her breast and then lowered her face to Linda and lifted her face from her breast so she could kiss her.

They kissed for a long time; Michelle pushing her groin into Linda’s and Linda pushed back. Michelle engulfed Linda’s aureole, flicking her tongue across the hard nipples. Linda held her there and gasped.

They tenderly attended to each other’s breasts and alternatively and passionately kissed each other. They were in no hurry although their sexual arousal was building.

Linda slid her hand under Michelle’s skirt and was not surprised to find that she was wearing pantyhose to help hold her penis in place. She played with Michelle’s thighs until her groans goaded her to seek what Michelle kept in her panties.

Linda thrust her hand inside the waistband of Michelle’s pantyhose, Michelle was wearing her satin panties over the top of her nylons to help gaff her penis and Linda struggled for a little until she found Michelle’s penis tucked between her legs. She gently freed it and Michelle’s erect penis fell into her palm.

She squeezed the turgid organ; already erect and leaking.

Michelle gasped and slid her hand under Linda’s skirt and gently scraped her fingernails across the tender flesh of Linda’s pantyhose encased thighs and then grazed the front of her nylon panties and felt Linda shudder.

Linda’s panties were soaked and Michelle put a finger inside them and explored Linda’s labia and found her clitoral hood. Linda wailed with delight and her heels rattled on the couch.

“Oh god that is lovely!” Linda sobbed with wantonness.

Linda squeezed Michelle’s penis through the layers of panty and pantyhose but she wanted to feel the hard flesh in her hand again. She released Michelle’s tumescent member from the silken trap and softly grasped it.

Michelle lay between Linda’s legs and kissed and fondled her as Linda reciprocated.

Intuitively Michelle knew it was time and she eased the gusset of Linda’s panties aside, used her fingernail to tear a hole in her pantyhose, and slid her engorged member into Linda’s slick channel. They took their time tenderly kissing and caressing each other as they slowly fucked. Linda rising to meet Michelle’s thrusts and Michelle grinding her pubis into Linda’s crotch to ensure she stimulated her clitoris.

When they orgasmed it wasn’t frantic. There was no frenetic thrusting of penis in vagina. Instead, as they sensed their orgasms approaching, Michelle pushed herself deep inside Linda and ground against her, ensuring clitoral stimulation. Linda raised her legs and pulled Michelle’s body hard against hers and rose up and scoured her sopping sex against Michelle; her vaginal sheath pulsed, milking Michelle of her ejaculate.

The two former prostitutes, now lovers, caressed, kissed, fondled, and canoodled; exacting every scintilla of pleasure from their union.

Michelle lay still with her head on Linda’s shoulder, nuzzling her neck and Linda cradled her head in the afterglow of their lovemaking.

“Did I tell you that Frankie stuffed a wad of cash in my handbag for me to go shopping?” Michelle broke the mood.

Michelle stood up and smoothed her skirt and slipped into her blouse but left it unbuttoned as she searched for her bag.

“Look,” she held out the money for Linda to see.

Linda was sitting up; getting dressed and she looked over at the chunk of cash Michelle was holding.

“Jeez girl you must give great blowjobs,” Linda teased and ducked under a high heel that Michelle flung at her.

“He said it wasn’t payment for sex; that I was to buy some nice clothes so he can take me out again tonight,” Michelle moued.

“Ok honey let’s go shopping!” Linda proclaimed.

“Hey. Frankie didn’t say anything about sharing with my girlfriend,” Michelle taunted.

“Well you at least owe me for the pantyhose you ripped when you fucked me,” Linda chuckled and ducked under a second high heel.

The two women hit Macy’s and Bloomingdale’s, buying Michelle a nice evening gown, high heels and costume jewellery to go with it and a pile of lingerie. They also bought her some nice daywear as Michelle’s small wardrobe currently consisted mostly of skanky streetwalker clothes.

Michelle generously spent some money on Linda too and the girls splurged and got a taxi home. They broke out the Jack Daniel’s and had drinks while they opened and inspected their wares. Michelle’s table, lounge, and floor was soon festooned with wrapping paper and packaging as the girls amused themselves, handling and trying their purchases.

After a couple of drinks and considerable amusement Linda finally broke the mood.

“I gotta go babe. I gotta meet the Feebs and update them. Let them know that you met with Frankie last night and that you are meeting him again tonight,” Linda said.

After seeing Linda out the door Michelle suddenly realised that no matter how much Linda loved her as a friend, she really was on her own.

Michelle began to prepare for the forthcoming evening. She reluctantly cleansed herself inside, hoping that she wouldn’t have to engage in any activity where said cleansing was essential. She was happy to kiss, cuddle, engage in foreplay and even fellate her newfound beau but the thought of anal sex was repellent.

She carefully applied her makeup and brushed her hair. She applied a fresh coat of nailpolish and had a drink and a cigarette while it dried. She tucked and gaffed herself and carefully stepped into a pair of luxurious fully-fashioned nylon stockings that she had bought on a whim. They felt wonderful and clipped them to a waist-cinching garter belt and then pulled up a pair of full-cut translucent black full-cut panties to smooth everything out so that she could slip into the red satin sheath-dress she had bought for tonight.

The dress was backless and split on one side all the way to the top of her thigh. Michelle had decided to forego her breastforms and just wore a red satin plunge bra that had slightly padded cups. With the bra she didn’t look quite so flat-chested, and besides, the ‘waif look’ was currently the rage. Anyway, her long legs sheathed in those diaphanous black stockings were going to draw attention away from her chest.

She slipped on a pair of red high-heeled pumps and accessorised with sliver costume jewellery. Michelle had been wearing earrings with her civilian attire as a detective in the drug squad so she already had both ears pierced. This allowed her to wear diamante-encrusted drop earrings that accentuated her neck and bare shoulders. They matched the necklace she wore which emphasised her meagre décolletage.

A liberal spray of perfume followed by packing the essentials into a small silver clutch purse and she was ready to go.

Only one thing.

Frankie had said he’d pick her up at eight and they would have dinner together and he would explain to her what it means to be one of his girls.

But where?

Surely he didn’t expect her to walk down to her Hunts Point street corner and wait for him there? Not dressed like this!

The answer came with a knock on the door.

Michelle opened it to find Salvatore dressed in a tuxedo with a smile affixed to his large tanned face. He was an imposing sight; six foot six inches of muscle.

“You look absolutely gorgeous honey. Frankie’s gonna go nuts when he sees you,” Salvatore beamed, he stuck his head in the apartment briefly and looked around inquisitively.

He assisted Michelle down the rickety dingy staircase, offering her his arm and steadying her when her heels rocked, then he escorted her to the limo and opened the door for her. Michelle noticed that he more than glanced at her long legs and stocking-tops when she slid into the back seat.

When she arrived at Delmonico’s Restaurant in Frankie’s limousine he was waiting for her at the curb and opened the door for her. She smiled when she alighted from the limo and her dress split open to reveal her long legs all the way up to her thigh. Frankie couldn’t help but stare.

Salvatore came around and whispered into his boss’s ear; Michelle would have liked to have known what was being said.

“Michelle. Delighted to see you again; I apologise that I couldn’t come and pick you up myself but I had to attend to some business,” Frankie offered Michelle his hand as she stepped onto the pavement.

He kissed her fingers and handed her a white rose.

“How thoughtful Frankie,” Michelle smiled and crooked her arm through his.

As they entered the restaurant all the heads turned.

“They're all looking at you because you are so beautiful,” Frankie said graciously.

“Or because you are so handsome,” Michelle squeezed his hand.

“Or maybe because I am a; what do you call it? A femminielli?” Michelle challenged.

“No! You look more feminine than any of the women here and even if anyone here suspected, they would know better than to say anything disparaging,” Frankie’s ire had risen.

“I’m sorry; I didn’t mean to upset you,” Michelle sounded genuinely concerned.

“You could never upset me while you look you do; you are the most gorgeous creature I have had the pleasure to meet,” Frankie patted her hand, still resting in the crook of his arm.

Michelle was impressed with the splendour of Delmonico’s and she looked around in awe. It was the swankiest place she had ever been in.

Frankie pulled back her seat and pushed it in behind her when she sat. He dismissed the drink waiter with an order and gallantly flicked her napkin and placed in her lap.

“I have taken the liberty of ordering us both a martini,” Frankie reached across the table and gently took her hand.

The drinks arrived and Michelle was delighted with it once she took a sip. She was feeling frisky and decided to tease Frankie and she licked the olive seductively on the cocktail skewer and then crushed it between her teeth.

Frankie gulped and waved to the waiter and ordered dinner for them both and the accompanying wines.

Over the entrée Frankie and Michelle engaged in repartee.

“Did Salvatore tell you where I live? Was that what he whispered in your ear when I arrived?” Michelle asked; a little embarrassed.

“You told me that you know who I am so you should not be surprised that I made some enquires about you; your background and so on. You came to New York from Nebraska and you are living full time as a woman; of this I approve. You are an elegant, beautiful and vivacious young lady,” he said, chewing on his linguini.

“But you are supporting yourself as a prostitute and of this I don’t approve. I told you last night that as far as I am concerned you are finished on the streets,” he broke off a piece of crusty bread and mopped up some sauce.

“So how do I support myself Frankie? I’m not going to be a kept woman. That is nothing more than another form of prostitution,” Michelle made a spirited reply.

She was pushing herself into dangerous territory but if she let Frankie hole her up in some apartment so he could come around and have sex with her whenever he felt like it she would achieve nothing. She needed to see who Frankie met with and to listen to what they talked about in order to get the information she needed to be released from this undercover task that had been forced on her.

“Well it’s like this. I don’t have a problem with prostitution per se, to me it is a victimless crime from which I make a lot of money,” Frankie smiled.

‘You should see some of the drug addicted, beaten up and preyed upon streetwalkers down at Hunts Point if you think prostitution is victimless,’ Michelle thought but kept her opinion to herself.

“As well as my nightclub, I also run a high-class relaxation establishment, a house of assignation, a bagnio,” his smile was wolfish.

“A brothel, a cathouse, a whorehouse,” Michelle replied a little tersely.

“Shall we compromise and call it a bordello. That word is not quite so harsh,” Frankie grinned.

“So are you offering me a job? Leave the corner and set up in your premises,” Michelle raised her brow.

Frankie blushed and for the first time showed her some annoyance.

“No! It’s not like that! I told you I don’t want you doing that anymore,” he sounded irritated.

“Look I’ve seen your place from the outside and Salvatore tells me that the place is…well excuse me…it’s a dump.”

It was Michelle’s turn to blush and show her ire.

Frankie patted the back of her hand soothingly.

“Well I would like to offer you a job and with it, a better standard of accommodation,” Frankie continued.

Michelle was about to interject but Frankie held up his hand.

“My current Madame, the lady who runs my establishment, has quit and none of the other women I employ are suitable.”

“You would have your own apartment above the establishment. It’s a nice place and has a separate access. What do think?” Frankie looked pleased with himself.

“You want me to be a brothel-keeper?” Michelle was incredulous.

“Hey you get a nice apartment; you get a well-paid job, you work for me so you’re as safe as you’re ever going to be. And…you no longer have to perform sexual services for a living,” Frankie sounded convincing; at least to himself.

“But I don’t know about that side of the business,” Michelle countered.

She was conflicted. If she took Frankie up on his offer she would undoubtedly get close to him, his businesses and hopefully his business partners. But it meant she would effectively become his kept woman.

“Look. Let’s finish our meal and I’ll take you to look the place over before you make up your mind ok?” Frankie countered.

Michelle nodded and drank some wine; her head spinning with apprehension, and she had to admit; a little anticipation.

“Let’s discuss other things, you are delightful conversationalist as well as a stunning young lady,” Frankie turned on the charm.

And they did. Frankie turned out to be a man of the world and quite the philanthropist, despite the fact that he was an organised crime kingpin.

Salvatore drove Frankie and Michelle through the boroughs of New York back towards Hunts Point. It turned out that Frankie’s bordello was not far from the street corner where Michelle had pretended to ply her trade.

During the ride they cuddled in the back of the limousine, the dark glass partition providing them with privacy. Frankie was delighted that Michelle was wearing stockings instead of pantyhose and he slipped his hand inside the spilt of her gown and helped himself to her thighs.

Michelle was happy to kiss him and she responded to his ministrations, stroking his hard member through his trousers. She was tempted to unzip him and fellate him in the car, hoping that it would preclude him wanting to fuck her.

Frankie allowed Michelle to take out and stroke his huge phallus but when she went to lower herself down to it he held her back.

“Let’s not sweetheart. Let’s wait until we get to your new abode where we can get comfortable,” he said and kissed her.

The car pulled up outside of a rather dilapidated three-story brownstone building; the curtains gave off a soft glow, the first floor curtains were red, which made Michelle smile. There were large glass double doors attended to by besuited, large doorman who nodded to his boss and Frankie nodded back.

“It looks a lot better on the inside. The façade is designed to keep the place incognito for those who don’t need to know,” Frankie grinned and touched the side of his nose.

“We will use the private entrance,” Frankie took out a key and led Michelle to a doorway at the side of the building.

He opened the door for her and let her take the lead.

“We’re on the third floor. The bordello is on the ground floor, I keep an office on the second, and the apartment takes up all of the third,” Frankie explained.

Frankie couldn’t help but play with Michelle’s satin-clad buttocks as climbed the stairway ahead of him. Michelle giggled. She had to admit that she was flattered.

The apartment looked to be spacious and tastefully decorated but Michelle could do no more than get through the door before Frankie pinned her against the wall and began to kiss he passionately.

Michelle managed to break the kiss and held him out at arm’s length,

“Frankie I really want to have a good look around before I make up my mind. Can we just do that without any hank panky?” Michelle beseeched him.

Frankie took her hands in his and kissed her cheek.

“Of course we can amore mio. I will behave like a gentleman I assure you,” Frankie smiled.

Michelle was more than a little surprised that Frankie had used the term ‘my love’. He had called her sweetheart and other terms of endearment but ‘amore mio’ seemed a little excessive.

Frankie led Michelle around the apartment extolling its virtues as he did. It had a small kitchenette, a large lounge room and even larger bedroom with a well-appointed ensuite bathroom and walk-in robe. It made her own grubby apartment seem paltry and demeaning.

“Check out the bedroom and amenities sweetheart and I’ll bring us a glass of wine,” Frankie kissed her cheek and left for the kitchen.

He returned with two glasses of red wine to find Michelle sitting on the huge king sized bed that had been made up with satin sheets and comforter. She was bouncing on it, testing the springs.

Frankie put down the wine and came over to her.

“It’s great bed Michelle. Here lie back on it,” he eased her back on the bed and stood back looking at her.

“Good you look good in that dress; I’d like to kiss your toes and then follow the seams of your stockings with my tongue,” he said to Michelle who was prone on the bed with her dress split open showing off her legs.

“Behave Frankie; you promised you would,” she chided him.

“But you’re just so sexy; I want to do things to you,” he smiled.

“Nice things,” he winked.

“Once I’ve licked your legs I’d like to rub my cazzo along them too, and maybe on your cute bottom,” he grinned wickedly.

Michelle felt fear creeping up on her. She knew that Frankie would soon want to do more that just talk about sex; he would want her body. She weighed her options but there weren’t many. Deep inside herself Michelle knew that eventually she was going to have to submit to Frankie; she just wanted to delay it as long as possible.

But what if he forced himself on her? She could try and fight him off; but he was a lot stronger than she.

Or she could capitulate. Just for tonight she could encourage him and let him hump her legs and ass which he seemed keen to do; worse case scenario she could even fellate him again. Turns out giving Frankie a little head wasn’t as bad as she’d imagined; she actually felt empowered when she did it last time. This seemed the safest option. Play along but at all costs but prevent him from fucking her.

Michelle sat up on the bed and Frankie handed her, her wine and took his own glass. They clinked glasses and drank.

“What other sort of things?” she looked over the rim of her wineglass.

The room was dark; lit only by the bedside table lamp.

Frankie looked at Michelle intently; Michelle had shifted position and now sat on the bed with her legs curled under her; the red satin evening gown clung to her body. The split was open and her long legs clad in the slinky nylons, seemed to shimmer in the lamplight and he was sure he could just make out the dark bands of the welts. He loved that Michelle was wearing stockings and he gazed at the dark seams and the reinforced fully-fashioned heels of her nylons as Michelle seductively dangled one of her high-heels from the toes of her right foot.

She was teasing him!

He looked into her heavily made-up eyes; then at her rouged cheeks and red-lipsticked lips, her jewellery glittered at her earlobes, wrists and decolletage. His eyes found hers again and he drew in a breath and inhaled her perfume.

“You know what sort of things. The sort of things I told that I want to do to you,” Frankie’s breathing was heavy.

He began to undress. He took off his jacket and kicked off his shoes and pulled off his sox. His bow tie went the way of his sox.

Frankie was now barefoot, dressed only in tuxedo trousers and a pressed white cotton shirt, which he had opened to the waist. His chest was exposed and the beginnings of an erection began to tent the fabric at his groin.

“We agreed there would be no hanky panky but it looks like you’re going to renege on the deal so I propose another deal,” Michelle said, she swung the high-heel from her toes.

Frankie was mesmerised by the shoe rocking back and forth; dangling from her dark-nylon clad toes.

“Deal?” he lifted his brows.

“You can play with my legs and my bottom as requested; I might even suck your, what did you call it? cazzo, if you behave yourself.”

“But no fucking. We save that special milestone in our relationship for a celebration” she glared at him intently.

“You mean I can dry hump your legs and you’ll suck my dick but I can’t fuck you,” Frankie grinned lasciviously.

“If you must put it so lewdly yes. And I keep my clothes on. All of them!” Michele replied, grinning cheekily at him.

Frankie seemed to consider Michelle’s proposition. Of course he could just take her if he wanted; but he didn’t want their relationship to be that way. He was genuinely infatuated with the pretty travisto.

“Agreed,” Frankie answered; his voice thick with lust.

Michelle let her dangling high heel drop to the floor and pointed her toe directly at Frankie. Her red-varnished toenails just perceptible through the gauzy black nylon.

“So what were you saying about kissing my toes and then following the seams of my stockings with your tongue?” Michelle wriggled her toes at him.

Frankie eagerly stretched Michelle’s legs out straight and pulled off her remaining high-heel. Michelle wriggled her toes again in anticipation of what was to come.

She really liked the feeling of power she held over this man as he worshipped her feet. His hands held her silken-clad ankles firmly and she could feel his hot breath on her feet through her nylon stockings. Then she felt his tongue begin to explore her toes. He ran it under the toes of both of her feet and then he licked each of her toes individually. She felt her cock hardening, tucked away in the crevice of her buttocks, held in place by the gaff.

Frankie tasted the silky material of her nylons, a scintilla of sweat, and a little of her perfume as he sucked her toes. He explored the ridge under her toes and then examined the whole of each foot with his tongue. The then put the toes of each foot into his mouth, alternating from left to right and sucked and slathered her feet. His cock was rock hard and he was tempted to reach for it but he had a better idea. Michelle had her eyes closed and was breathing quite heavily. The sensuous tactility of this man worshiping her feet was surprisingly erotic and she was extremely aroused.

Frankie removed Michelle’s feet from his mouth and lowered them towards his groin. Michelle lay back on the bed filled with expectation and lust. She was going to enjoy giving Frankie a footjob. Once again she felt empowered by her hold over him.

Michelle leaned forward a little and the split in her gown opened wide exposing her stocking-tops and the crotch of her full-cut panties. She lowered a stocking encased foot into Frankie's lap and watched him begin to squirm and moan.

"Oh Michelle!" Frankie moaned.

Michelle's dark reinforced nylon toes rubbed against Frankie's hard penis through his pants. Frankie lifted Michelle's other nylon encased foot and rubbed it all over his face. Michelle enjoyed listening to his muffled moans.

Michelle rubbed one of her feet against his erection while Frankie worshiped the other foot pressing it firmly over his nose and mouth; inhaling her foot odour and licking at her nylon imprisoned toes. He reached down and stroked the stocking foot that was pressing on his hard cock. He continued to moan; licking and sucking on Michelle's gossamer-glad toes, sliding his other hand farther up and down Michelle's long, sleek stockinged-encased legs.

"Take it out," Michelle whispered seductively.

Frankie fumbled at his lap; unbuttoned his fly and released his engorged penis. Michelle worked her stocking foot all around his huge rampant member. She worked her toes on the underside of his shaft, just below his glans. After a few strokes from Michelle's toes Frankie was squirming and groaning. A filament of pre-ejaculate oozed from the tip of his penis and adhered to Michelle's foot; the translucent globule glistened on her dark reinforced nyloned toe. Frankie ran his hands up and down Michelle’s stocking-sheathed leg from the tips of her toes to the tops of her hose. He moaned with pleasure as Michelle massaged his phallus with her silken foot.

Michelle pulled her other foot away from Frankie's face and dropped it into his lap. She placed each of her feet together and arched her soles, trapping Frankie's engorged manhood between them. She moved her feet back and forth masturbating Frankie's cock with her nylon-sheathed feet.

Frankie's cock was swollen, the glans bright red and almost ready to ejaculate onto Michelle's feet. Pre-seminal fluid was flowing freely from the eye of his penis, and the sensation of the wet slick nylon sliding up and down his shaft was exquisite. Michelle's toes became soaked with Frankie's pre-seminal fluid.

Frankie looked down at his lap again and watched as Michelle's shapely feet slid up and down his straining penis, milking him with her diaphanous encased appendages. The nylon over her toes glistened with pre-ejaculate and Frankie ran his hands up and down Michelle's legs all the way up her thighs to the dark welts and garter straps. He bucked back and forth fucking Michelle's feet and he could sense his orgasm approaching. He firmly grabbed her ankles and pulled her feet from his cock.

“Hey! I was enjoying that!” Michelle whined.

“That’s not the way I wanna come darling,” Frankie smiled up at her.

He stood up and dropped his pants and ripped off his shirt so he stood naked before her. His penis was rampant and throbbing. He fell on her and Michelle giggled as he began to hug and kiss her.

Michelle opened her mouth and met Frankie’s tongue with her own; she crushed his lips with hers whilst at the same time raising her legs and wrapping them around his flanks. She could sense that Frankie loved the feel of her nylons against his bare skin and her plan was to get him to ejaculate against her legs or her body; worst case scenario she would fellate him. To be honest she was enjoying every minute of their passionate embraces. Her cock was hard; trying to break free of the gaff. As long as Frankie didn’t try to fuck her, Michelle was confident that her plan would work and she could maybe take a little pleasure herself whilst Frankie took what he wanted from her.

Frankie’s cock was rubbing on Michelle’s thighs; he enjoyed the different sensations as his cock shifted from her sheer nylons to the cool firm flesh of her upper legs. His cock touched one of her garter clips and he winced as the cold metal snap nipped the flesh of his penis. He didn’t mind actually because the mild pain held back his orgasm. He was close to coming but didn’t want to just yet.

He extricated himself from Michelle’s embrace; but much to her dismay she found that Frankie had other plans as he mounted her again. She willingly opened her legs to accommodate him; even helping him ruck up her dress so he had unfettered access to her legs. He kissed her and his cock brushed against her stocking welt leaving a silvery trail of pre-cum on the silky dark nylon. Michelle felt Frankie adjust himself then she felt his hot cock on the front panel of her full cut satin panties; it was hard and throbbing and she became concerned about what he might try next.

“Oh Frankie you can rub on my panties but remember our agreement; no penetration!” she warned him.

She raised her hips and ground her belly against him. The feel of his hard member pressing against her flesh with only the flimsy layer of panty material between their bodies was extremely arousing. She kissed him deeply, driving her tongue deep into his mouth, wriggled her hips and wrapped her legs around him once more. She wanted to bring him to release. To feel his hot seed splash on her thighs or her belly.

Frankie slid his cock under the leg opening of her panties and his cock came into contact with her warm flesh. Michelle panicked and tried to push him off her but Frankie hung on and probed at her groin with his hard manhood. She drummed her heels on his back and pushed at his shoulders to try to dismount him.

“No Frankie! No! You promised!” she shrieked.

It was too late; Frankie’s cock was buried in her groin.

“Stop! Stop! Stop” Michelle cried, but Frankie was committed.

“Shh. Shh. Shh, Michelle it’s ok honey,” he whispered in her ear.

He stroked her hair and then kissed her eyelids, her cheeks and her mouth with extreme tenderness.

Michelle reluctantly realised she might have to give up her virginity tonight. As far as Frankie was concerned Michele had been fucking guys for money for nearly ten years; there was no reason for her to turn him down.

Michelle set her resolve and stopped struggling and lay still letting Frankie kiss and embrace her. It felt comforting, exciting, and terrifying all at the same time. She looked in his eyes.

“Please be gentle?” she whispered.

They kissed and fondled each other and Michelle felt Frankie begin to rub his erection on the front of her panties again and she began to respond to his attentions; she was very aroused herself. His hands stroked her stockinged legs rubbing them from knee to stocking-top and then his fingers stroked her bare thighs.

“Mmm, that’s nice,” Michelle purred.

Frankie slid his hand along the front of her panties and then he slipped his fingers inside the waistband. Michelle began to struggle again.

“Shh, it’s ok; just let me do this, trust me you’ll like it,” Frankie kissed her ear.

Michelle felt more than a little trepidation as Frankie’s hand slid inside her panties. His fingers found her penis, semi-erect, taped under her groin. She struggled a little but Frankie held her still and gently extricated her cock from the gaff, dropping the disused tape on the bed. He positioned her member along her stomach and pulled her panties back up over it and lay down on her. His erection pressed against hers through the satin panty material. He began to rub his cock against hers and he kissed her deeply.

Michelle had never felt anything so exciting in her life. She had at times masturbated with panties or stockings covering her penis but the feelings could not compare to the sensation of having a hard member rubbing her own with the layer of panty material between them. She could feel Frankie’s cock pulse and throb as it massaged her own quivering shaft.

She lifted her legs and wrapped them around Frankie’s body; locking her heels behind his back.

“I like this Frankie! Please make me come!” she whimpered and ground herself against his hard, hot cock.

Michelle was close to orgasm and she hoped Frankie was too. She wanted to feel his hot seed flood her panties and coat her cock with his semen as she too erupted.

Frankie adjusted his position slightly and pushed his cock into the crevice of her panty-clad buttocks and began to hump her there. It felt nice but not as nice as his cock rubbing on her cock.

“Put it back please honey,” she whispered in his ear and kissed him passionately whilst she wriggled her buttocks trying to extricate his cock.

"Stop it you naughty boy," she giggled.

Frankie did not stop; instead he pulled the gusset of Michelle's panties aside and slid his cock into the crease of her soft creamy buttocks.

"Stop it!" Michelle yelped; seriously now.

Frankie ignored her and his glans probed her sphincter. Michelle screamed and wriggled but Frankie was too strong. He held her down with one hand whilst he used the other to guide his penis into Michelle’s anus.

Michelle screamed.

“No!”

“Please don’t Frankie; I don’t want this I’m not ready for this,” Michelle pleaded.

“It’s ok Michelle. I know my cock is big and the first time I put to you it will hurt a little but then it will be wonderful. It will be just like your first time,” he smiled down at her.

Frankie did not know that this would actually be Michelle’s first time and that she did not want to be sodomised.

Frankie reached out to the bedside table and opened the drawer. He kept a tube of KY jelly in there and he squeezed a dollop of viscous lubricant and spread it thickly over Michelle’s sphincter and his long thick shaft; all the while Michelle wriggled and struggled underneath him. He used his body weight to hold her down.

“Stop! Stop! Don’t! Don’t!” she screamed.

But they were alone in Frankie’s apartment and there was no one to hear her pleas; besides she knew her deflowerment was inevitable. She just didn’t want it to be tonight; or any night.

The glans of Frankie’s penis pierced her sphincter. The lubricant eased the entry of Frankie’s cock past her tight bud but the pain was still incredible. Michelle moaned and bucked but Frankie would not remove his phallus from inside her, he only had his glans inside her and he didn’t try to push any more of himself inside her but he still held her down.

“Oh that hurts!” Michelle whimpered.

“Shhh Honey; relax and it will be ok,” Frankie whispered, trying to sooth her.

“Please take it out!” Michelle moaned.

Michelle was feeling a constant deep burning sensation combined with spasmodic twinges of intense pain shooting from her sphincter. She whimpered and wriggled, trying to expel the offending intruder from her back passage but Frankie held on.

“Michelle! Listen to me!” he hissed; and she stopped struggling and listened to him.

“Look honey, the worst is over I promise, if you lie still and let me; I can make this experience special for you. Or you can keep struggling and I’m going to fuck you anyway but then it’s going to hurt.”

Michelle realised that she had no real choice and besides she would do anything to stop the excruciating pain that was coming from her sphincter. She sighed and lay still; her anus pierced by Frankie’s penis but she was smart enough to know that fighting was only going to make the pain worse. She tried to relax her sphincter but her instinct was to try to push against the object invading her anus; not to accept it.

“That’s it honey,” said Frankie as he felt Michelle’s sphincter spasm as she tried to relax it.

“It will be ok I promise.”

Michelle was quietly sobbing but at the same time she forced her inner muscles to relax. Amazingly the twinges of intense pain began to subside; she still felt the burning sensation around the entrance to her anus but it was tolerable. Frankie took another globule of KY jelly and applied it to his shaft.

“Ok honey; keep relaxed, I really don’t want to hurt you,” Frankie soothed.

Millimetre by millimetre Frankie slowly pushed himself inside Michelle; he took his time and whenever Michelle flinched he stopped and soothed her as his shaft slowly disappeared inside Michelle’s rectum. Michelle felt full and intensely uncomfortable, the urge to expel Frankie’s penis was immense and she had to physically prevent her internal muscles from contracting.

After ten minutes Frankie had about half of his girth buried inside Michelle’s anus he raised her legs so that they rested over his shoulders. He looked down at her pretty face and smiled.

“It’s ok Michelle; you’re doing fine.”

Michelle’s only response was a silent tear. She had stopped sobbing and now and only mewed softly, but now that she had learned to relax her sphincter she really didn’t feel any pain. Even the burning sensation had subsided; she just felt full.

Frankie continued to press slowly forward cooing and encouraging Michelle to stay calm and relax her anal muscles. When he had about three-quarters of his shaft inside her, he sensed her internal flesh respond and she gasped. He knew what it was; it was not pain. His glans had found her prostate gland. Her reaction was pleasure not pain.

Frankie knew better than to rush things; he took his time pushing the remaining few inches of his shaft inside Michelle until eventually he was buried inside her with his scrotum resting snugly against her loins. He wriggled his penis inside her to stimulate her prostate and he kissed her. Michelle began to respond and she kissed him back.

“Mmm, that feels good Frankie. The pain has stopped and it feels quite nice,” she smiled up at him.

“I told you it would hurt but only for a little while. Just stay relaxed and it will get better,” Frankie lowered his face to hers and kissed her again.

He stroked her silken-hosed legs and she rubbed then against his body because she knew he liked it.

She felt Frankie’s glans rub against an area inside her that suddenly caused waves of intense pleasure to course through her body. As his penis stimulated her prostate, rings of pleasure ran up and down her; her sphincter responded and slackened and began to emit its own tingling ripples. Michelle gasped.

When Frankie lowered his mouth to hers she kissed him back, deeply, passionately. She drove her tongue into his mouth and lifted her buttocks up off the bed and pushed herself up against him; she moved her legs so they were around his waist; she locked her ankles together and held him against her. She felt totally feminine lying here underneath this man; wantonly giving herself to him.

They fucked slowly but passionately taking their time; Frankie easing his penis in and out Michelle’s anus with long slow thrusts as she raised herself up to meet him. There was no fervent thrashing or pounding; just firm, slow deep thrusts provided the maximum stimulation for both of them. They said little to each other, the fucking was accompanied by one long passionate kiss.

"Oh fuck me honey!" Michelle moaned and began to push back against Frankie as he slid in and out of her tight passage.

Michelle's cock became fully erect. Frankie’s reached down and squeezed her through her panties.

"Oh jeez!" Michelle moaned.

Frankie fucked Michelle and she fucked him back; both of them moaning and groaning with the intensity of their passion. He squeezed and stroked Michelle's hard penis and the stimulation she felt from having her cock massaged through her satin panties amplified the rings of pleasure that radiated from her anus. She was going to orgasm.

Frankie's cock throbbed too as he frantically squeezed Michelle’s cock through her panties. He ejaculted deep inside her; his cock pulsing and juddering as his scrotum contracted ejecting steams of hot semen. Michelle felt her back passage flood with Frankie’s sperm and this triggered her own orgasm.

Michelle felt him orgasm; his cock was fully embedded in her, his scrotum tickling her buttocks when he shuddered and wriggled his member inside her as it pulsed and throbbed. He was kissing her passionately, their tongues entwined, lips mashed, their teeth occasionally cracking against each other with the intensity of the kiss.

Michelle moaned as her own orgasm shook her body and she felt her penis begin to pulse and expel her issue. Frankie slid a hand between their bodies and milked her as she ejaculated, hot semen soaked into her panties.

Michelle slid her stocking-sheathed legs up and down Frankie's torso and pulled him harder against her; her fingernails raked his back as their lips crushed together and their tongues intertwined. Michelle drummed her heels against Frankie's hard buttocks.

Frankie lay on top of her, supporting his weight on his elbows as they both slowly came down from their orgasms. He placed little soft kisses on her lips and kissed her on the eyelids and stroked her hair. Michelle felt feminine and fully sated. She felt like she knew what it was like to be a woman who had just been made love to, and her lover was contentedly happy to remain in her arms.

"I’ll take the job and the apartment," Michelle said sometime later and smiled up at her new lover.

To be continued.

Pillow Talk
By
Michele Nylons

Chapter Four – Goomah

Michelle Clooney felt Frank Caputo’s erection prodding at her backside; it slid inside her panties and probed her buttocks until it found her sphincter. Frankie held her hips and slowly pushed himself deep inside her. Michelle relaxed her sphincter as she had learned to do to accommodate the girth of his large cock in her anus. There was no need for more lubricant, Frankie had fucked her twice last night and his semen was still inside her along with the residue of the KY jelly they had used.

They were spooning in the big bed and Frankie had woken up horny as he always did when he stayed the night. Michelle was dressed in nylon baby-doll pyjamas and sheer hold-up stockings. Frankie insisted that she wear lingerie to bed.

Dawn was just creeping through a chink in the curtains as Frankie began to slowly fuck Michelle. He pulled her to him, nuzzling her neck and she wriggled her buttocks invitingly. Frankie snaked a hand around her body and found her erect inside her panties and he squeezed her as he thrust in and out of her buttocks.

They took their time making love and ejaculated together, as they often did. Michelle had learned how to suppress her orgasm until Frankie was ready; well most of the time anyway.

They lay still with Frankie’s penis slowly deflating inside Michelle’s anus until it fully constricted and popped out. Michelle felt some of his issue dribble from her sphincter; it soaked into her flimsy panties. She turned around so that she could kiss her lover and Frankie wrapped her in his arms and hugged and kissed her until Michelle began to struggle free.

She slipped into a pair of kitten heeled slippers and noted that her stockings were full of runners as usual after a night with Frankie. She would take them off and throw them away when he left; he insisted she always wear nylons in his company. She slipped on a satin dressing down.

Michelle went to the kitchenette and brewed coffee.

“You want breakfast darling?” Michelle called out to Frankie who was in the shower.

“Nah. I’ll eat with the guys down at the social club; Lilo called a sit down. Some of Sharky Ramone’s guys have been dealing on the other side of Halleck Street in Lefty Ruggiero’s patch so we gonna negotiate a truce. That fucking Sharky is a Young Turk but so long as that gavone knows he gotta kick up to Lefty and Lilo maybe we can settle things,” Frankie called from ensuite, towelling himself off.

Frankie stayed at Michelle’s apartment about four nights a week. Always on Fridays, never on Sundays, and then whenever he could get away from his wife during the week. He also often dropped into the Bordello unannounced during the day for a little afternoon delight with Michelle.

Michelle had stayed well away from the subject of Frankie’s home life and Frankie seldom spoke about it with her, which was expected. He sometimes referred to his wife Benedetta as ‘that bitch’ when he was drunk and angry, but Michelle knew that like most Italian men he venerated his family. Michelle was his goomah but she would never be held in the same respect as his wife.

That said, Frankie treated her well. He paid the rent on the apartment, was always buying her clothes and jewellery and was happy to take her out on the town to certain establishments. They’d had their ‘arrangement’, as they referred to it, in place now for just over six months and it was going well. Michelle was still learning how to run the ‘Gentlemen’s Club’ but the girls were good and the regular clientele behaved themselves so it pretty much ran itself. Michelle was really just the hostess and bookkeeper.

Michelle was slowly and carefully collecting information about Frankie and his mob dealings. She was careful not to push but she was an attentive listener and snippets like the one she had just gleaned about the sit down would be passed on to Linda Gordon as soon as Michelle could meet with her. Michelle and Linda never discussed their business on the phone.

Frankie came out of the bedroom dressed in a fresh suit, shirt, tie, and polished shoes. His black mane was still wet from the shower and Michelle was once again amazed at how handsome he was. He kissed her on the side of the mouth so he wouldn’t get lipstick on himself, squeezed her ass and headed out.

Michelle poured coffee for herself and lit a cigarette. Her eating habits had changed significantly; dictated by Frankie’s veracious appetite for anal sex. She walked over to the bed and pulled back the covers. Good. Except for semen on the sheets and lipstick and mascara on the pillowcase there were no other splotches or stains. Michelle was terrified of leaking something horrible during sex and had established a rigid routine. She had an enema in the morning before her shower and douched before going out in the evening. She swallowed a couple of Imodium after each procedure. She ate only one meal a day, usually dinner with Frankie, so that she had all night to digest it. Other than drinking coffee, Coke a Cola, and of course alcoholic drinks, which she was finding she liked to do more of lately, she didn’t snack.

Other changes had taken place in her life too.

Mitchell Clooney had disappeared from her life forever. She didn’t think about her life before she met Frankie. She found it was the only way to deal with her current situation. To just be Michelle Clooney, transvestite Madame and goomah of Frank ‘The Stallion’ Caputo, and nothing else. Other than her meetings with Linda she had no ties to her former life anyway and Linda treated Michelle as her girlfriend and she too never raised the spectre of Mitch Clooney.

Michelle and Linda met about three times a week, mostly in coffeehouses or bars but sometimes in Linda’s apartment where they would make love. Linda was fulltime undercover now too as Michelle’s handler. She was still only on a patrolwoman’s wage and Michelle helped her out with cash and clothes.

Strictly speaking the money Michelle took from Frankie was considered proceeds of crime and technically she was not supposed to spend any of it but Michelle rationalised that she needed the cash to keep her cover intact. Besides, the FBI had no way of knowing how much money Frankie gave to Michelle.

Michelle took care of her morning toilette, fixed her hair and makeup and slipped into her working attire. During the day it was a navy blue business suit, white satin blouse, sheer flesh-toned pantyhose and high-heeled pumps. She wore expensive panties and bra underneath. She looked simultaneously professional and sexy which was perfect for her job as Madame at the Bordello. In the evening she changed into one of her many elegant evening gowns and exchanged pantyhose for stockings.

Frankie liked the way she dressed and would often drop in for a quickie, leading her upstairs if there was time or simply bending her over her desk in her office if there wasn’t. He had a veracious appetite for sex, which Michelle was finding matched her own now that she was living full-time trans. Michelle dressed not only to please Frankie but also to please herself. On the days she knew that Frankie had family commitments and she wasn’t required in the bordello, she would often dress down. She experimented with jeans, satin bell-bottoms, A-line skirts and sweater-dresses. Her favourite casual attire was hotpants, velvet boots and fitted blazer, she always turned heads when she went out dressed like that; her pantyhose-sheathed legs seemed to go forever. She also had a collection of cork-soled wedgies and chunky high-heels to complement her casual wardrobe.

Experimenting with fashion was an engaging pastime that pleased Michelle and she and Linda often went on shopping sprees. Linda took Michelle to her first hairdressing appointment. Michelle had let her hair grow and even though her hair wasn’t quite as long as Farrah Fawcett’s, Michelle wanted to try the feathered look. It worked for her and more importantly Frankie liked it.

Michelle did her rounds of the Gentlemen’s Club. Mornings were dedicated to cleaning and preparing the place for the clientele that would start drifting in the late afternoon. She checked to make sure the lounge and bar were spotlessly cleaned; the bar restocked and the dark wood panelling and furniture polished. The lounge and bar was where clients were served drinks and allowed to relax as they chose which of the girls they would like to engage with. Michelle then checked the girls ‘work rooms,’ which were very well appointed and included large comfortable beds freshly made up with clean linen and satin-lined comforters. She inspected the ensuite bathrooms, one shared between each of the two bedrooms, and finally made her way into her small office where she reviewed the previous day’s takings, entered the figures into a ledger along with outgoing expenses and balanced the books. She kept another ledger which was a diary of the girl’s appointments with the gynaecologist that the Bordello retained. The girls were required to undertake a health check every two months. In the 1970s condoms were not really in favour. It was a cash only establishment and there was a large safe in the corner to which only she and Frankie had the combination.

Frankie often bought in large amounts of cash from his other business dealings and stashed it in the safe and took chunks of cash away as his needs arose. Michelle did not ask where the money had come from or where it went but she did catalogue the cash movements and passed the information onto Linda to pass to the FBI.

By ten o’clock most of her office and administrative duties were completed and she would take a rest until she was required to undertake her hostess duties, meeting and greeting the clients and generally overseeing the running of the place. Her deputy was Rita Cordova, a long-time courtesan who was now in her forties. She was still very good looking and had kept her figure and she was intelligent and articulate and still in high demand by some of the more discerning customers. Rita deputised for Michelle when Michelle took time away from the job, placing the takings into a small wall safe in Michelle’s office. Michelle would then enter the taking into her ledger and move the money into the big safe.

Michelle and Rita had a cordial, professional working relationship but were far from friends. Some of the younger girls doted on Michelle, fascinated that she was a trans woman living full time as a female. Michelle was like a den mother to them and kept her relationship friendly and affectionate but she retained her authority and was willing to punish any of the girls who broke the bordello’s code of conduct. Her punishments were limited to withholding or reducing wages or making the offending girl do extra cleaning duties or even suspending the girl from work. Anything more severe was Frankie's purview. Michelle was glad that she seldom had to punish her brood of courtesans.

The number one rule was silence and secrecy. The girls were never to discuss what they did and who they did it with; some of New York’s most famous and infamous men used the establishment. It was frequented by businessmen, politicians; the rich and powerful who wanted a bit of spice in their life. Members of the New York mob also used the club. The bordello was an agreed no-man’s-land or neutral territory where men could relax and take their pleasures with the utmost discretion and without fear of reprisal. Frankie jokingly referred to is as ‘Switzerland in New York’.

The next equally important rule was no stealing; no stealing from the customers and no withholding from Frankie. The girls were well paid and well looked after, and any infringement of these two rules could mean severe retribution.

Michelle completed her rounds and was sipping coffee and reading the newspaper in her office on the second floor when the reality of what she was doing and who she was doing it with fully dawned on her.

Tucked away on page four of the New York Times was an article written by Rob Hanson, one of paper’s crime reporters.

‘Body of Woman Fished from East River Identified’ the headline read.

‘The body of a woman found floating in the East River last week with her hands cut off has been identified as Irene Valasso, a thirty-three year old former prostitute with ties to the Bonanno crime family. Valasso is believed to have operated a call girl ring and a high-class brothel in the Bronx and was reported missing three months ago. Valasso’s body is believed to have been floating in the river for two to three weeks but remained relatively intact due to the near freezing water. It had taken until last Friday for the body to be identified. A relative, who declined to be interviewed by this reporter, made the identification.

The NYPD refused to comment when this reporter inquired as to whether the cutting off of hands is a Mafia punishment for theft or embezzlement….’

Michelle paled. Her hands began to shake and when she put down her coffee cup it rattled in the saucer.

She remembered what Frank had said to her when he offered her the job:

‘My current Madame, the lady who runs my establishment, has quit and none of the other women I employ are suitable.’

Quit? Did anyone quit the Mafia? Frankie had once made a joke at a dinner with his wiseguys and their goomahs.

“So Benny ‘The Dip’ comes to see me and says he wants out of our thing cause his wife wants him to go legit. I told him ‘what are we; the fucking boy scouts? Fuggedaboutit!’” everyone at the table laughed.

Was she now considered an ‘associate’ because she worked directly for a ‘Caporegime’?

Michelle invited Rita Cordova to her office for a cup of coffee. They sat side by side making small talk whilst sipping coffee and smoking cigarettes. Michelle had deliberately left the Times open at the Irene Valasso story on the side table. She noticed Rita glance across at it repeatedly; she was obviously distracted by it.

“Did you see the story,” Michelle indicated the newspaper with her chin.

“Don’t believe everything you read in newspapers sweetie,” Rita drew heavily on her cigarette and blew smoke at the ceiling.

“Did she work here? Irene Valasso I mean? Did she work here?” Michelle asked.

“Let me tell you something Michelle. At the moment you are untouchable because you are Francis’ comare; but that position can be perilous,” Rita began.

“I should rightly have taken over as Madame when Irene vacated the position. Irene got greedy and although she wasn’t Francis’ comare, they liked to fuck. But it looks like that didn’t help her when she got caught skimming,” Rita pointed at the Times.

“But Francis likes travistos, femminielli, more than he likes women. Anyone else who is part of their thing would have been clipped for having those tendencies but it is condoned because you are beautiful, feminine articulate and because Francis Caputo earns more than any Caporegime in the Family.”

“And so he puts you in charge and makes you Madame. You are an amusement, a curio for the clientele and to the girls who work here. They respect you only because you are Francis’ comare.”

“You have the job that should rightfully be mine. But don’t worry; I will be your right-hand girl, your deputy, your handmaiden. Until one day Francis tires of you and puts you back on the street…or you end up floating in the East River like your predecessor,” Rita’s face was a mask of malevolence.

Michelle was shocked and dismayed but she soon recovered.

“Tell me Rita, until I came along did Frankie like to fuck you too?” Michelle retorted angrily.

“Who says he’s stopped?” Rita grinned maliciously.

Rita stood up and smoothed out her skirt.

“Thanks for the coffee and the chat Michelle but I have to get back to work,” Rita smiled sweetly and left the office, closing the door behind her.

Michelle sought out Linda and they met at Linda’s apartment. Michelle paced up and down chain-smoking while Linda tried to calm her down.

“Michelle honey; the FBI have you covered, nothing is going to happen to you. The mob doesn’t kill police officers; it draws too much heat,” Linda tried to console her.

Linda knew that she was telling a white lie. The mob didn’t hit law enforcement officers but undercover agents were considered fair game. There was currently at least one contract out that she knew about on NYPD Detective Doug LeVein who had infiltrated Paulie Vario’s crew in the Brooklyn. LeVein was currently in Witsec, whereabouts unknown.

There was no way she was going tell Michelle this. She had finally got Michelle comfortable living full time as a trans woman and feeling that she was safe as Frankie Caputo’s goomah, she did not want to undo the good work they had done so far. Linda knew that this secondment to the FBI could be her way out of the shitty and corrupt NYPD into a Federal Agency that respected women.

Half a bottle Jack Daniel’s and package of Marlboro Menthol Lights later Michelle had calmed down and she snuggled up to Linda on the couch. She updated Linda about the sit down at the social club; with Lilo Galante, Sharky Ramone’s and Lefty Ruggiero. This was important intel and Linda left Michelle snoozing on the couch and went outside to use a pay phone to inform her FBI handlers.

By the time Linda had returned Michelle had brightened up.

“I gotta get back to the Gentlemen’s Club hun; I’ll call you later,” Michelle kissed Linda goodbye.

Back at the bordello Michelle nipped upstairs brushed her teeth and freshened her makeup then came back downstairs to her office on the second floor. The club opened at two in the afternoon and it was an hour until opening time.

Suddenly there was a hammering on the door; she could hear the commotion coming up the stairs.

“Open up! Police!” hash voices came through the closed door.

Michelle looked at Rita Cordova questioningly.

“So Frankie didn’t tell you about the Pussy Posse did he?” Rita took Michelle by the shoulders.

Of course Michelle knew about the prostitution and solicitation branch of the vice squad; Christ at one time she had worked for them as an undercover streetwalker. But she also knew that like most of NYPD; the vice squad was corrupt. In her former life she used to be in the narcotics branch of the vice squad and her corruption was the reason that she was in the predicament that she was now.

“I know who they are but surely Frankie pays them off to leave us alone,” Michelle looked worried as the banging grew louder.

“Of course he does but part of the deal is that they can come around and use the girls now and then. They get to take a freebee but not during business hours. They usually phone first but sometimes they get high or drunk and they just drop in. Don’t fuck with them; just let the girls give them their freebies and they will soon be on their way.” Rita said in a calming tone.

“Jilly! Penny! Get the door and take those representatives of New York’s finest out back and see to their needs,” Rita called downstairs and led Michelle back to her office.

“We’ll stay in your office until they leave. Hear no evil, see no evil and speak no evil,” Rita grinned closing the door.

“How often does this happen?” Michelle asked.

Rita was pouring two shots of bourbon into crystal glasses.

“About once a month four or five of them will come around. When Irene Valasso ran the place she used to take on one or two of them herself. Said she wanted to know who was on the take in case she ever got pinched. If you ask me, blowing a copper is a high price to pay for that kind of information, but coming from the streets I suppose you had to hand out freebies all the time,” Rita passed a glass to Michelle.

Michelle played along.

“Yeah I’ve given away my share of freebies to those goons,” she replied sipping her whiskey.

“Anyway the girls will soon take care of them,” Rita lit a cigarette.

Then the door burst open.

Two men, obviously high, burst into the room. They were wearing suits; their coats open to reveal revolvers in pancake holsters. They were clearly cops. Their pupils were dilated; their eyes bloodshot and they continually wiped at their noses.

“Sorry boys; wrong place. The girls are waiting for you in their rooms downstairs,” Rita smiled at them.

Michelle was just happy that she didn’t recognise either of them; not that they would have recognised her anyway.

“Is this where you keep the special pussy,” one of the detectives chuckled.

“That one looks a little old to me Bill and the other one must be the tranny broad we heard about,” his partner giggled.

The detective named Bill closed the door and walked over to the small bar and removed the glasses off a silver tray. He poured white powder on the tray and chopped it into lines with a razor blade pendant that he took from around his neck.

“Look we don’t want any trouble. Like I said; the other girls will attend to your needs,” Rita forced a smile.

“Nah! Fuck that! We want that special reserve pussy you keep locked away in here,” Bill snickered.

They snorted two lines each then offered the tray to the women.

Rita and Michelle shook their heads.

“Lock the door Rick,” Bill said ominously.

“Look boys. You know the deal. You can have any of the other girls you like. If you like you can even have me; but Michelle is off limits. She’s Frankie's goomah; you know what’s gonna happen if you touch her,” Rita warned them.

“Why should I care if some dago tranny fucker says I can’t fuck his closet-queen, faggot, hooker, girlfriend?” Bill said angrily.

“You know the consequences if do!” Rita barked.

“Fuck the consequences. I always wondered what it would be like to fuck a sissy-boy and that girl is sweet. If I didn’t know otherwise I’d swear she was the real McCoy,” Bill snickered.

“Or we can just fuck you both anyway, beat you up a little, and then call in the pussy wagon and bust you both for prostitution,” Rick growled.

He began to tap out more powder onto the tray while Bill took off his coat, watching his partner with red-rimmed eyes.

Rita pulled Michelle into the corner and looked searchingly into her eyes.

“Look these two dipshits are coked up; high as kites and likely to do anything. Let’s be pragmatic about this; we’ve both been whores before. Let’s just give them what they want and then let Frankie deal with them,” Rita proposed.

Michelle was terrified but she really had no choice; if she refused she would likely get taken against her will and then get busted for prostitution, which could create all sorts of complications when they went to book and process her down at the precinct and took her prints. She’d come too far to let two drugged-out coppers ruin her operation.

She totally surprised Rita when Michelle spun on her heels and sashayed over to the two cops.

“So which one of you boys wants the tranny and who wants the girl?” Michelle gave them her best Betty Boop impression.

“Ok Bill; lets have some fun with these two, we’ve got a bit under an hour the way I figure it,” Rick sounded excited and Bill nodded.

“I want you two to kiss each other. It’s gonna be hot seeing a tranny and a chick make out,” Rick was almost panting.

Michelle shrugged as did Rita and they approached each other in the middle of the small office and did just that.

Michelle took Rita in her arms and inhaled her seductive perfume as their lips met. She felt Rita’s ample bosom press into her meagre chest. Rita slipped her tongue into Michelle’s mouth and Michelle responded by taking Rita’s ample buttocks in her hands and squeezing them. Rita reciprocated.

“Jesus Bill will you look at that! Those two whores took to groping each other like a couple of nymphomaniac lezzies,” Rick squealed.

The two detectives divested themselves of their jackets and ties and unzipped their flies.

“Play with her tits!” Rick bawled at Michelle.

Michelle was actually enjoying kissing Rita. Rita was a very sexy and beautiful woman and Michelle found herself very attracted to her. Rita was surprised that she felt the same way as Michelle felt about her. Rita had had the odd lesbian experience but kissing and fondling this gorgeous trans woman was something entirely different. It was decadent and sensuous.

Michelle and Rita disengaged briefly and took off their jackets and blouses. Michelle hardly filled her black satin bra, which was padded slightly; but the cups of Rita’s red lace bra were overflowing with her smooth creamy bosoms. Michelle hefted one of Rita’s breasts out of her cup, the nipple was already distended, a bruised brown colour, and she lowered her face to it.

“Oh my!” Rita gasped as Michelle suckled on her nipple and then used her fingers on Rita’s other breast.

Michelle felt Rita’s nipples become harder as suckled one and tweaked the other; she could feel Rita’s heart rate gallop and her breathing become ragged.

Michelle moved her face away from Rita’s breast and kissed her again whilst still stroking her other teat. Rita placed her hands on Michelle’s meagre bosom and stroked her small orbs. Although Michelle had hardly any cleavage, her nipples were very sensitive and she moaned when Rita broke the kiss and suckled Michelle’s teats.

“Christ Rick I’m gonna blow my load just watching these two,” Bill whooped, stoking his penis which was poking out of his suit pants.

“No way! I’m gonna fuck one,” Rick replied.

“You! Play with her pussy and you play with her dick!” Rick balled.

The women obeyed the policeman. They resumed kissing each other and reached for the hems on their skirts. Michelle pulled up Rita’s black taffeta skirt and Rita pulled up Michelle’s navy blue business skirt. The women rucked the skirts up around their waists. Michelle was wearing black satin full-cut panties over her taupe sheer-to-the-waist pantyhose and Rita was wearing red lace panties with tan control-top pantyhose over.

Michelle slipped her fingers between Rita’s legs and could feel the heat from her vagina through the gusset of her pantyhose. The fabric was moist to her touch. Rita reciprocated and felt Michelle’s erect penis trapped between her legs by the layers of panty and pantyhose.

“Come on you whores; get your cunt and cock out where we can see them,” Rick bellowed.

Rita was struggling with Michelle’s gaff so Michelle pushed her hand out of the way and put her own fingers between her legs. She tore out the crotch of her pantyhose and freed her penis and scrotum. She shimmied to drop her testes from the inguinal canals into her sac and then allowed her erect penis to fly forward from her panties.

Rita took the shaft of the offered organ in her hand and squeezed it.

“Oh jeez, be careful honey or I’m gonna come all over your hand,” Michelle gasped.

The feel of Rita’s long soft fingers gripping her shaft and sliding over the glans of her penis was exquisite. Michelle pulled down Rita’s control tops and panties, bunching them together at the top of her thighs. The aroma of hot cunt filled the room. Michelle dipped her fingers into Rita's vulva and separated her labia with two splayed fingers and then used another finger to gently stroke her clitoris.

“Oh my god Michelle!” Rita pulled Michelle against her and kissed her, grinding her crotch into Michelle’s hand.

She squeezed Michelle’s cock and slowly began to stroke her.

Bill and Rick watched the two beautiful women, one of whom possessed a rather large appendage, kiss and fondle each other as they themselves masturbated.

“Fuck this! I’m joining in!” Bill exclaimed and pulled Michelle away from Rita.

He spun her around pushed her over the desk. Michelle steadied herself; gripping the edge of the desk, she spread her legs and raised her derriere. She presented herself to Bill.

“Come on then! Stop taking about it and fuck me!” Michelle wriggled her buttocks seductively.

Bill moved behind her, kicked Michelle’s ankles open a little wider and pulled the gusset of her panties and ripped pantyhose aside. He slid his long thin cock into her all the way.

“That’s the way big boy,” Michelle encouraged him.

Similarly Rick spun Rita around on her heels, pushed her over the desk and slammed his stubby thick cock into her slick vagina.

The two cops began to fuck the two women bent over the desk. Bill watched his cock slide in and out Michelle’s tight ass and Rick watched his slide in and out Rita’s slick cunt. Michelle’s sphincter puckered when Bill pulled all the way out and then enveloped his shaft as he plunged back in. Rita’s inner labia clung to Rick’s phallus as he pulled out of her tight cleft and then eased himself back in.

“Oh my god; fuck me!” the girls shrieked in unison, wriggling their buttocks and pushing back to meet the thrusts as the two coppers fucked them.

Michelle and Rita looked into each other’s eyes, they were shoulder to shoulder, bent over the desk, both being ravaged by the detectives but they could see the lust on each other’s faces.

They kissed. They explored each other’s mouths as they enjoyed the severe fucking they were both receiving.

Seeing the two beautiful women kiss while they were being fucked sent the two men over the edge. Bill seized Michelle’s hips and drove himself in her all the way, grinding against her soft buttocks as he ejaculated deep inside her.

Michelle felt Bill’s hot semen spill inside her and his glans grinding on her prostate, which caused her to orgasm with him. Her seed splashed on the carpet as she writhed with lust, squeezing Bill’s cock with her anal muscles to increase both their pleasures.

Rick hammered his cock in and out of Rita and howled as he erupted, shooting his load inside her sodden cunt. Rita pressed back against him so that the shaft of his cock stimulated her clitoris and she too came; shuddering and squealing into Michelle’s mouth as they kissed.

When the two detectives had finished fucking the two women they pulled out their cocks and wiped the dribble on the girl’s buttocks, laughing as they did.

Michelle and Rita remained mute, bent over the desk not looking at the men, just staring ahead. They heard the detectives zip up, put on their coats and ties, unlock the door and leave.

Michelle pushed her genitals back inside her panties and pantyhose and Rita pulled up her pantyhose and her panties. They both pulled down their skirts and smoothed them out.

They stood silently and put their blouses back on and adjusted their clothing.

They looked at each other and shrugged.

“Not a word of this to anyone,” Rita whispered.

“Not a word,” Michelle replied.

To be continued

Pillow Talk
By
Michele Nylons

Chapter Five – Braciole

The first plate whizzed past Frank Caputo’s right ear and crashed into the wall, closely followed by a second that skimmed off his shoulder and shattered on the floor.

“For fuck sake Michelle if I wanted this fucking drama I’d go home to Benedetta,” Frankie whined, but he was laughing drunkenly.

“Why don’t you then? You can fuck her and Rita Cordova both for all I care!” Michelle threw another plate that flew well wide of Frankie.

She and Rita had agreed that they wouldn’t tell anyone about them being fucked by the two vice squad detectives. There was no agreement when it came to Frankie still fucking Rita after installing Michelle as his goomah.

The more Michelle thought about it the more livid and inflamed she became. If Frankie was fucking Rita, then you could bet that the rest of the girls knew about it, which made Michelle a laughing stock in their eyes.

“Well are you? Are you still fucking Rita Cordova?” Michelle had run out of plates and threw a saucer this time.

“So what if I am? I never said we were exclusive!” Frankie roared.

He turned his back and slipped out the door, slamming it behind him as another saucer crashed into it.

Michelle was dressed in a blue satin-sheath evening gown, black bra, panties and suspenders, black fully-fashioned stockings and blue high heels ready for her evening shift in the Gentleman’s Club. Her makeup, which had been perfect, was now ruined, her eyes blackened by running mascara.

Her tears were not caused by pain or even jealousy; they were tears of anger bought on because Frankie had lied to her, telling her that besides his wife Benedetta, Michelle was the only other woman he was having sex with.

Michelle left the kitchenette and retired to the bedroom to fix her makeup when she heard the front door again. She turned to face the bedroom door and was surprised when Frankie pushed Rita Cordova into the room.

“So you couldn’t keep your mouth shut Rita! And Michelle; you got a temper like a wildcat!” Frankie said firstly to Rita and then Michelle.

Rita glared at Michelle and Michelle shook her head unspeakingly indicating that she hadn’t told Frankie about being ravaged by the detectives in her office.

“So now you know I’ve been fucking both of you!” Frankie had been drinking all afternoon and was in no mood for temper tantrums from his women.

“So Michelle; now you can take your revenge. You can fuck Rita while I watch,” Frankie roared.

“You’re drunk!” Michelle spat and made to walk past him.

Frankie pulled her to him violently.

“Do what I say you puttana!” he pushed Michelle and she stumbled on her heels onto the bed.

“You too cagna!” he called Rita a bitch in Italian and threw her on the bed too.

Rita was also wearing an evening gown; red satin split up one side. The split opened to reveal her long legs sheathed in sheer taupe pantyhose.

“So let’s make things even. Suck her cock!” Frankie said in a drunken drawl.

“Don’t be absurd!” Rita scrambled on the bed, trying to get up.

Frankie pushed the two women back down on the bed. He was a big man and very strong.

“Ok! Enough! Both you bitches do as I say!” he growled.

“I wanna see a show. You both know I got a thing for women wearing nylons so I wanna see my women put on a show just for me!” Frankie snatched up a bottle of bourbon and drank directly from the bottle.

Michelle and Rita looked at each other and realised that Frankie meant business.

Rita nodded her consent to Michelle; they had made out with each other before so what was the difference? Michelle nodded back.

“Ok Frankie. Here is your show,” Michelle took Rita’s hand and placed it on her calf.

Rita drew a sensual line along Michelle’s stocking with a manicured bright-red fingernail.

Rita’s finger traced the backseam to the dark welt at the top of Michelle’s stocking. She lazily circled the silky textured fabric and flicked at the silver garter tab.

“Don’t you find it rather archaic though; wearing stockings?” Rita began to stroke Michelle’s gossamer-sheathed thigh.

Michelle trembled at Rita’s touch.

“But pantyhose can be just as sexy don’t you think?” Rita lifted a toned, translucent-sheathed leg.

Michelle couldn’t resist and reached out to stroke it delicately.

It was Rita’s turn to shudder.

“Mmm. They are very soft and sheer. Are they sheer-to-the-waist?” Michelle's hand disappeared inside the split in Rita’s dress to explore the top of her thighs.

“And satin panties over your pantyhose…I like that too,” Michelle skimmed her fingers across the front of Rita’s panties.

“Yes and you too,” Rita’s fingers delved inside the split in Michelle’s dress and found her black satin and lace panties.

The two coquettes grazed fingers across panties and gazed at each other licentiously.

Michelle scooted over to make room for Rita who crawled across the huge bed and lay beside Michelle; they stared at each other and then Rita reached out gently stroked Michelle’s face.

“Best we do what our old man tells us,” Rita sighed and leaned into Michelle and kissed her.

They touched tongues as their lips pressed together and then pressed their bodies together.

“I didn’t know you were a lesbian,” Michelle whispered in Rita’s ear.

“I am when the woman has a cock,” Rita grinned.

“Jesus! You two are fucking hot!” Frankie gasped.

The women kissed and entwined their legs, rubbing their pelvis’ together whilst unclasping each other’s dresses so they could pull the bodices down. Then they removed each other’s brassieres. Rita had full breasts whilst Michelle’s were small and pert. They pressed their breasts together as their ardour grew and they kissed frenziedly.

“Christ you girls got me going,” Frankie began to undress, almost falling over because he couldn’t take his eyes of Michelle and Rita.

Michelle and Rita caressed each other’s bosoms, Michelle was impressed with the heft of Rita’s pendulous breasts and tweaked her swollen nipple whilst Rita was able to fit all of Michelle’s small breast into her mouth and lap at her teat with the tip of her tongue. Michelle lowered her face to Rita’s chest and suckled on her fat, hard nipples. They both enjoyed the breast-play whilst grinding their groins together and rubbing their legs against each other’s. The room was filled with the sound of whimpers, gasps, slurps and the rustle on nylon on nylon.

Michelle lifted Rita’s face to hers and kissed her, their breasts squeezed together as they hugged and caressed each other.

Hands went exploring under dresses, lazily sliding up nylon-sheathed thighs, caressing and groping as passions peaked. They hiked their dresses up out of the way so that they could access each other’s groins.

Rita slid her fingers along the soft skin above Michelle’s stocking-tops and slipped them inside the leg of her panties. She had been here before and she soon found Michelle’s penis taped between her legs. She ripped away the surgical tape and Michelle gasped in Rita’s mouth as her semi-erect penis sprang free and her testes lowered into her scrotum.

Michelle reciprocated and her fingers slithered inside the leg of Rita’s panties and found that Rita was wet and had saturated the crotch of her pantyhose. Michelle smiled too, and used her finger to trace the outer folds of Rita’s sex. Rita gasped and opened her legs, encouraging Michelle to explore further; she gripped Michelle’s penis and began to improve her erection.

Michelle responded and dug her fingernail into the translucent fabric of Rita’s pantyhose gusset until it parted. She poked her finger in the hole and enlarged it. Without hesitating she pushed her fingers into Rita’s sopping maw and explored the slick folds and contours of her vagina, sliding a finger inside and using her thumb to press on her clitoris.

Rita arched her back and gasped. She gripped Michelle’s now fully tumescent erection and squeezed and then released it. She languidly ran her fingers up and down its length and slid the pad of her forefinger on the fraenulum using the copious amount of pre-ejaculate leaking from Michelle’s cock to lubricate her shaft.

Their kissing became frantic and manic as they pawed at each other. Their bodies were pressed close together with their hands enthusiastically manipulating each other, their sheer-nylon-encased legs entwined and entangled.

Michelle rolled over so that she was straddling Rita, her cock was pressed into Rita’s crotch; rubbing on her soaked cunt through her satin panties. Rita’s raised her hands and held Michelle by the shoulders.

“Put it in her Michelle! Fuck that whore!” Frankie was now naked and stroking his huge cock while he watched his two lovers.

“Yes put it in me Michelle,” Rita groaned.

Michelle eased aside the crotch of Rita’s panties and pressed forward, her glans parted Rita’s labia and pressed against her hooded clitoris.

Rita rose on her haunches pushing up; she wanted that hard cock inside her. She was so excited to have the beautiful young woman with the hard cock lying on top of her, about to penetrate her.

Michelle smiled down at Rita, she enjoyed teasing Rita, rubbing the tip of penis on Rita’s engorged clitoris but Michelle too wanted release.

She pressed her haunches forward and her cock slid inside Rita’s sopping, buttery vagina. She lay between Rita’s legs and pushed it in all the way so that her pubic bone pressed on Rita’s pubis, stimulating her clitoris while her shaft inched slowly back and forth inside Rita’s tight sheath.

Michelle heard the bedsprings creak and then felt the bed sag behind her. Then she felt Frankie's hands on her waist as he hunched down over her, his cock slipped inside her panties exploring her crevice, searching for her sphincter.

Frankie groaned as his long, thick, hard cock slid inside Michelle’s anus. Michelle grunted as her ass was filled with hot throbbing cock.

She lowered her face to Rita’s as Frankie entered her.

Michelle and Rita kissed; their moans stifled by crushed lips and slavering tongues. Rita lifted her legs and locked them around Michelle's waist so she could raise herself and grind her mound against Michelle and encourage her to thrust her cock in out of her vagina. She wanted to be fucked.

“Fuck me you bitch! Fuck me!” Rita gasped.

Frankie gripped Rita’s ankles as he squatted behind Michelle, his cock buried in her tight ass.

Michelle slowly eased her phallus in and out of Rita’s tight juicy passage; Rita’s nylon-sheathed legs scoured her flanks encouraging her, her highheels raked Michelle’s side. Michelle responded and fucked Rita with long hard strokes, extracting her glans to Rita’s entrance and then thrusting inside her, smashing their pubis together.

Frankie got into sync with Michelle and thrust forward on Michelle’s backstroke as she fucked Rita. Michelle was feeling sexual excitement and sensuality like she had never experienced in her life. Her cock was buried deep in Rita’s tight, slick cunt whilst her anus was filled with Frankie's enormous throbbing cock.

The three lovers rutted and fucked each other, encouraging and goading each other with their mouths, their legs, their bodies and their sex. Rita’s vagina rippled with exquisite sensations of pleasure as Michelle fucked her, her clitoris was palpitating with sensual delight. Frankie's cock was sheathed by Michelle’s tight anus, pressing against her prostate. Their orgasms were building like a volcano about to erupt.

Michelle sensed Rita’s urgency as she bucked and wriggled beneath her, clinging to her like a boat in a storm. She could also feel Frankie quicken the pace as he fucked her hard and fast and sensed her own orgasm building. The feel of Rita’s silky legs on her skin, the pressure of Frankie's phallus on her prostate and stretched sphincter, her own panties caressing her scrotum intensified the sensations she felt from her throbbing penis as it pounded away at Rita’s slick tight hole.

The three lovers clung to each other and fucked, oblivious to the world around them. Rita came first, screaming obscenities as she scratched and pawed at Michelle, forcing her mound against Michelle’s pubis. Her cunt quivered and rippled; incredible feelings of pleasure surged through her vagina as Michelle’s cock pulsed and swelled, spewing forth a torrent of hot semen deep inside her.

Frankie came next, barely hanging onto Michelle as she writhed and bucked beneath him. His cock quivered and ejaculated his scalding issue deep inside Michelle’s anus.

Michelle clung to Rita, driving her down into the bed as she swivelled her hips and ground herself against her pubis, emptying herself as Frankie emptied himself inside her. She gasped and groaned with the intensity of her orgasm as her cock convulsed and her anus constricted and sent shockwaves of pleasure through her body whilst milking Frankie of the last of his seed.

The three lust-ravaged lovers lay gratified and exhausted in a tangled heap.

Frankie's erection finally became recumbent and he extracted it from Michelle’s anus. A stream of his semen followed and dribbled from her sphincter. He slid her panties back into place to absorb his ejaculate. With a little difficulty Frankie extricated himself from the girl-sandwich and lay down on the bed beside them and reached for his cigarettes.

Michelle rolled off Rita, slipping the gusset of Rita’s panties back into place to soak up the spend dribbling from her cunt.

She lay beside Frankie and took the offered cigarette and passed it on to Rita. Michelle took another cigarette and the three of them lay side by side panting with exhaustion and coming down from their respective orgasms as they smoked.

“Well that was different,” Michelle suddenly guffawed.

Rita reached out and playfully spanked Michelle’s thigh.

“I guess that’s one word for it,” she snorted.

Frankie had fallen asleep and Michelle extracted the cigarette from his fingers and stubbed it out. Then she stubbed out her own and then took Rita’s and stubbed it out too.

Michelle and Rita looked at each other and suddenly burst out laughing. The laughing stopped as they reached for each other once again.

“These are the latest wiretaps that the FBI gave me,” Linda said, inserting the cassette into her cheap cassette player.

Michelle was at Linda’s catching up and updating her on the Frankie situation. She had not told Linda about the vice squad cops ravaging her and Rita and definitely not told her about her recent menage au trois.

“It’s a wiretap conversation between Vincent ‘Vinnie’ Boccia and Nicky ‘The Wop’ Angelini. Interestingly not only are they talking about Frank Caputo, they are also taking about you,” Linda pressed play on her cassette player.

Michelle raised her brows and listened.

Vinnie: ‘You see that finocchio Frankie has a femminielli fronting at the club now?’

Nicky: ‘Jeez…if he wasn’t a Capo and pulling in big, Lilo would have had that fanuc clipped ages ago’

Vinnie: ‘I tell you what though. I saw that maricǒn cooze walking down at the Point last week. She was wearing those hotpants with the sheer calze autoreggenti.. you know.. the nylons and the fuck-me shoes. That cooze has great legs and a tight ass. I’d like to stick my braciole in that.. aha’

Nicky: ‘I’ll give you that she’s very pretty for a travisto. She’s got those lips.. you know.. full and red.. I’d like her to suck on my bischero for a while’

Vinnie: ‘What about her braciole? You think she has a big one? Do you think she sticks it in Frankie?’

Nicky: ‘Madre mia! Fuggedaboutit!”

Vinnie: ‘So enough about the cooze. What about the thing with Frankie?’

Nicky: ‘The Boss gave the go ahead but he wants his taste’

Vinnie: ‘Ok I’ll see you at the place and we can work it out’

‘Click.’ The line went dead.

“So what does all that mean? “ Michelle looked at Linda questioningly.

“Are they going to hit Frankie?” the panic was evident in Michelle’s voice.

“Hey! Don’t worry about that, you heard what they said, Carmine Galante won’t approve a hit on Frankie while Frankie is the family’s biggest earner,” Linda soothed Michelle.

“But it sounds like Rusty Rastelli is stirring up trouble from inside prison. Lilo took over as Boss when Rusty went down but Rusty still has some guys in the family that are very loyal to him.”

“The FBI think Rusty has sanctioned Nicky and Vinnie to hit one of Frankie's businesses; my guess is it will be your bordello,” Linda explained.

“It’s a Gentleman’s Club,” Michelle corrected.

“Whatever,” Linda blew out her cheeks exasperated.

“So what do I do now Linda? I can’t warn Frankie about the robbery because he will want to know where I got the information. I’m supposed to be a dumb goomah and brothel keeper,” Michelle sounded agitated.

“It’s a Gentleman’s Club,” Linda replied sarcastically.

Michelle rolled her eyes.

“The FBI wants you to up the ante. They see a possible advantage if the Bonanno family starts infighting,” Linda said hesitantly.

She registered the shock on Michelle’s face.

“They figure that if you can get Vincent Boccia or Nicky Angelini keen on you, that you can encourage dissension and instability in the Family,” Linda whispered apprehensively.

Michelle looked appalled and aghast.

“You’re fucking joking right! The deal we have is that I report pillow talk and anything else that I pick from Frankie or the wiseguys that use the Club. The fucking Feebs now want me to betray Frankie and start a fucking war? Are they kidding?” Michelle was stupefied.

“I won’t do it!” Michelle spat petulantly.

“They ain’t giving you a choice doll. They want you feeding information to Vincent and Nicky so that they take a stab at Frankie's Gentlemen’s Club. Then they want Frankie to find out who robbed him and then the whole Bonanno Family will likely go to mattresses,” Linda conveyed the FBI’s instructions.

“Fuck no!” Michelle was adamant.

“The Feebs say you do it or it’s off to Lewisburg Penitentiary. They say they’ll indict you under RICO; say that you were briefed as an undercover operative not to participate in criminal activity but that you willingly did so,” Linda took Michelle’s hand in hers.

“They’re serious Michelle. They threw in the usual threat about exposing you as a trans woman to the inmates,” Linda murmured.

“Or even worse; expose you to the Mob as an informant.”

“Those fuckers!”

“So I betray Frankie to Vinnie and Nicky and then I betray Vinnie and Nicky to Frankie. A double, double cross; and try not to get caught in the crossfire,” Michelle lit a cigarette.

“Hey! Who’s to say either of those two knuckleheads will even be interested in me?” Michelle smiled pragmatically.

And that was where it all started to go wrong.

‘The Place’ referred to by Vinnie Boccia turned out to be the Toyland Social Club run by Nicholas ‘Glasses’ Marangello, a Bonanno soldier loyal to Rusty Rastelli.

The FBI had Toyland under surveillance and a wiretap in place. They fed information to Michelle though Linda Gordon and advised of a forthcoming meet with Vinnie Boccia and Nicky Angelini.

Michelle nervously prepared herself. She arranged for Rita Cordova to look after the Club while she went out to supposedly get her hair done.

Michelle wore a red A-line skirt that showed off her long legs clad in taupe control-top pantyhose; her feet shod in white cork platforms. A white satin blouse, white satin and lace bra and panty set completed the ensemble. She put on cosmetics, dark eye makeup and bright red lipstick to match her skirt. She accessorised, brushed her hair, put on a lightweight red bolero jacket, picked up her purse and stepped out.

Michelle was nervous and kept looking around, not that she was likely know if she were being followed; she had no counter-surveillance skills. She also didn’t have much in the way of a plan; just get noticed by Vinnie or Nicky and hopefully they would engage with her somehow so she could ingratiate herself.

All knew was that the two wiseguys knew who she was.

She could have taken a cab to the club that was located at 94 Hester Street downtown but at this hour of the day it was actually faster to take the subway.

She boarded a car at Hunts Point Avenue taking the Pelham Bay Park line to Canal Street. The ride took about half an hour and she nervously kept sweeping her skirt under her legs so she wouldn’t sweat on the vinyl seat. A middle-aged businessman sitting across from her deliberately missed his stop so he could stare at her legs and the occasional panty peek. Michelle was oblivious.

Her heart was racing as she walked through China Town along Hester Street to the Toyland Social Club. She had been informed that Nicky Glasses only used the club for business; even though she was Frank Caputo’s goomah there was no way she was getting inside. It also didn’t help that although she was a stunning young woman; she was still a travisto.

Michelle saw that there was a small coffeehouse across the street in Little Italy so she took a seat at an outside table and ordered espresso. She chain-smoked as she sat there watching the Social Club; she could see that there were men inside but couldn’t see who they were.

She opened her purse and looked at the pictures of Vincent Boccia and Nicky Angelini and looked back across the street. Sure enough Vinnie came outside with Nicky Angelini in tow. They stopped and began to get into an earnest conversation both lighting up cigarettes to cover their mouths as they did.

Michelle’s heart was hammering in her chest but this was her chance. She stood up and went inside the coffeehouse and ordered another espresso and then came outside. She deliberately tripped and upturned the little metal table and the chair. They crashed to the pavement with a clattering cacophony that turned every head nearby her way.

Vinnie looked over and she saw a look of recognition cross his face as he tapped Nicky on the shoulder. He pointed her way and said something to Nicky.

Michelle made a show of trying to right the table, bending over, giving the whole street a glimpse of her luscious thighs. The propitiator of the coffeehouse came to the door and was about to assist when Vinnie and Nicky arrived on scene.

“Bellissimo! If it isn’t Frankie's lovely business associate! I’ve seen you at the Businessman’s Club. Let me help you,” Frankie made a big deal of picking up the table and Nicky picked up the chair and made a fuss of dusting off the seat.

“Please be seated,” Nicky made a flourish.

Michelle smiled her most beatific smile and sat down, smoothing her skirt under her, crossing her ankles and straightening her hem across her thighs. She saw that the two mobsters liked what they saw.

They dragged over a couple of chairs.

“Frank Caputo is a friend of ours,” Nicky beamed, using the euphemism that signalled that they knew that Frank was a made guy and that they too were connected.

“Well any friend of Frankie's is a friend of mine,” Michelle beamed.

The waiter put down Michelle’s coffee and a clean ashtray; Vinnie pointed at the glass of espresso and looked questioningly at Michelle.

“Oh yes! Please, please join me,” she smiled widely, showing off her full red lips and white teeth.

She remembered what Nicky had said about having Michelle ‘suck on his bischero’.

“I'm Michelle Clooney,” she offered her hand to each in turn to kiss the back of.

“I’m Vincent Boccia and this is Nicky Angelini,” Vinnie smiled back at her.

“So how is Francis? I haven’t seen him for a while; he’s always busy with the Gentlemen’s Club and that nightclub that he owns on the other side of town,” Nicky grinned.

“Oh he’s fine and I don’t know about the nightclub, but the Gentlemen’s Club is humming along just fine,” Michelle reached into her purse and took out a Marlboro Menthol.

Both of the wiseguys scrambled for their lighters.

If Frankie had heard her tell these gentlemen that his Club was humming along he would have slapped her around. She had been told to never discuss his business with anyone. But Michelle was deliberately trying to entice the two mobsters to rob the place by baiting the trap.

Vinnie lit Michelle’s cigarette and gave Nicky a knowing look.

“So as well as being Frankie's comare you’re also the boss at the Gentlemen’s Club?” Vinnie grinned.

“Oh I wouldn’t say I’m the boss; I’m the hostess,” Michelle grinned.

Vinnie looked at Nicky meaningfully and nodded. Nicky nodded back at him and stood.

“I gotta take care of that thing,” Nicky said to Vinnie.

“Scuse; I got urgent business,” Nicky smiled at Michelle and hurried away.

“So what brings you downtown Michelle?” Vinnie asked.

“The shopping is better in Manhattan; you get classier clothes and shoes,” Michelle beamed back.

“Well you obviously haven’t shopped yet. My Cynthia always comes back loaded with shopping bags and parcels when she hits the stores,” Vinnie grinned.

“So your place must be doing real good if you’re out shopping the big end of town?” Vinnie lit his own cigarette.

“Oh we are more than getting by,” Michelle wanted Vinnie to think that she was a ditz with no discretion and a big mouth.

They made small talk for about ten minutes and then, Michelle happy that she had baited the trap, made to leave, throwing five dollars on the table to pay for her coffee.

“Well I better go and spend a load of Frankie's money,” Michelle smiled vapidly.

“Here. Let me help you princess,” Frankie helped Michelle up.

He took her by the elbow and she was surprised when he didn’t let go and started leading her to the curb.

“Its fine thanks Vincent; I’ll just walk a few blocks to…”

Michelle never got to finish her sentence.

A big black Ford LTD pulled up to the curb with a squeal of brakes. The trunk popped.

Vinnie quickly looked up and down the street. He opened the trunk of the LTD, flipped Michelle into it and slammed it closed.

To be continued

The trunk of the LTD was huge so Michelle had plenty of room; the carpet was clean but it smelled a little of gas. The first thing she thought of was that she would suffocate on exhaust fumes but when she realised that wasn’t the case she began to take stock of situation.

She had been kidnapped by Vincent ‘Vinnie’ Boccia and Nicky ‘The Wop’ Angelini; thrown into the trunk of their Ford LTD and they were now on their to who knows where. She could hear the road noises and there was a pinhole near one of the brake lights that she could see out of. They had exited Canal Street and were in the Holland Tunnel.

Michelle was tempted to kick at the trunk lid or try to prise it open but she knew that it would be nearly impossible and that Vinnie or Nicky would likely tie her up and gag her or do worse if she made trouble. She hoped in vain that the FBI surveillance team watching the Toyland Social Club had seen her being abducted.

The car cruised past Liberty State Park and onto the New Jersey Turnpike. This wasn’t good; they were heading out of town. They crossed the bridge across Newark Bay and continued on, deep into New Jersey.

Michelle had just under two hours to ruminate on her fate. Were they going to kill her was the main question? Michelle didn’t think so; there were plenty of places in the city where they could have whacked her and then driven her corpse out here for disposal. They wanted her alive; either to extort a ransom from Frankie or to obtain more information from her about Frankie's operation. Or both.

The terrain became rural and they passed by an establishment called The Pine Barrens Store. Michelle shivered despite the warmth of the trunk. The Pine Barrens is a huge forest stretching across New Jersey and is mostly uninhabited. The road suddenly changed from blacktop to dirt and finally they entered a rutted track. Michelle was getting thrown around in the trunk and it was getting darker outside.

The car stopped and she heard the crunch of footsteps and then the trunk opened. Michelle squinted as her eyes accustomed themselves to the weak winter light and she drew in deep breaths of the cool crisp clean air. Vinnie smiled down at her with a wicked grin and then she was lifted out of the trunk.

Michelle looked around and saw that she was surrounded by tall pines and scrub; she was standing on a carpet of pine needles. The track petered out and the only man made object was a dilapidated wooden shack; likely used by poachers.

Vinnie had a nine-millimetre pistol in his hand and he waved it at Michelle indicating that she should make her way over to the hut.

The shack’s windows and doors were long gone and there were gaping holes in the roof. There was the remains of a fire and a stained mattress with dirty old blankets piled on it in one corner. The floor was littered with empty liquor bottles, beer cans and cigarette butts. A selection of ancient used rubbers had been discarded here and there, mainly near the mattress. A pair of ripped nylon panties and tattered pantyhose were hanging ominously from a nail above the mattress.

A rickety old wooden table sat in the centre of the room and beside it was an old and rusty steel framed kitchen chair and Vinnie indicated that she should sit in it.

Michelle did not like the silence.

Nicky pulled up a beer crate and sat in front of Michelle as Nicky paced up and down behind her to keep warm.

They lit cigarettes and gave one to Michelle; her hand shook visibly when she took it from Vinnie. She was lost, cold, and terrified.

“Ok doll this how it is,” Vinnie began.

“You’re going to tell us everything you know about the Gentleman’s Club. We know that you run the place and that you live there so we expect a full and frank account; anything less and you and my friend Mister Barretta here are going to get very personal,” Nicky waved the gun in front of her eyes.

Michelle just nodded.

Michelle was being used by the FBI to provide them with information regarding the New York Mafia and in particular Frankie Caputo and the Bonanno Family. She was not there to get herself involved in family infighting, which would likely get her killed. She began to tell Vinnie and Nicky everything she knew about the club.

She explained how the club was laid out, where the burglar alarms were and how they were activated and deactivated. She told them about the Club’s operating hours and that it closed at 3am and that she was the only person living there in the apartment on the third floor and that unless Frankie stayed over she was alone.

Then she gave them the information that they really wanted. Where the big safe in the office on the second floor was located. About Frankie bringing in money from his other business ventures and putting it in the safe and also the days on which the safe was usually at full capacity.

“Is that everything?” Vinnie shook her by the shoulders.

“Yes. That’s everything I know,” Michelle lied, her head down.

“Then there is only one more thing you can do for us,” Vinnie grinned.

“I guessed you’d want that. You don’t have to take it; I used to be a hooker so it’s no big deal for me to give you what you both want; but I promised Frankie I’d be faithful,” Michelle forced herself to look at Vinnie and Nicky and plead with them.

Michelle was lying to the two mobsters about being a hooker and her fidelity to Frankie but at this stage she would do anything to keep herself form being killed.

“Honey we don’t care either way. Fucking you is just another way for us to get back at Frankie,” Nicky said viciously.

Nicky pulled Michelle up out of the chair and spun her around.

Michelle tottered on her heels and came to rest with her butt hard up against table. The cabin was deathly quiet and she could hear the water dripping off icicles from the roof.

The mobsters looked her over, their eyes roamed brazenly over her face, body and legs.

“She’s better looking than some of the women I’ve fucked!” Nicky laughed.

“I have always wondered what it would be like to get some travisto ass,” Vinnie grinned.

Michelle had already made up her mind that she going to capitulate and show these two goons a good time. She would act a little reluctant to be more convincing and to spice it up for them.

The mobsters ogled her. The red A-line skirt showed off her long legs clad in taupe control-top pantyhose; her feet shod in white cork platforms. The white satin blouse, inside which were her meagre breasts in the white satin bra. Her dark eye makeup and bright red lipstick looked inviting.

Nicky moved into Michelle and forced her back against the table.

Michelle felt trepidation as she was pulled into Nicky’s arms and he kissed her full on the lips, sliding his tongue into her mouth, encircling her in his arms. Michelle forced herself to relax as he explored her mouth with his tongue, pulling her body hard against his. She could feel his cock begin to swell against her body. Nicky took Michelle’s hand in his and moved it between their bodies down into his crotch and grunted into her mouth.

“Touch it bitch; you know you want to.”

Michelle reached out and tentatively stroked Nicky’s tumescent member through his pants. It felt big and hard and although she was sure it was her imagination, it appeared to radiate heat through the fabric. Nicky’s cock tented the front of his pants and he gave out a little moan as Michelle cautiously fondled him, her ruby-red fingernails scratched at the fabric she slowly and excruciatingly traced the outline of his cock.

“Take it out honey,” Nicky panted into her mouth and then crushed her lips with his.

He was pushing his groin against Michelle’s body, trapping her hand between them, as she stroked the bulge in his pants. His tongue wriggled in her mouth; the taste of her lipstick and scent of her perfume further arousing him. He pulled his groin back from Michelle’s body and took her hand off his tented trousers and guided her fingers to his zipper.

This was a similar situation as with the vice cops and on some primeval level she was surprised and flattered that she could get a man so fiercely aroused.

Nicky impatiently tugged at her hand until she capitulated and slowly started to unzip his fly. The chafing sound of Nicky’s zipper opening sounded ominous in the cold quiet cabin; silent except for Nicky’s groans of pleasure and Michelle’s ragged breathing.

“Hot damn the bitch likes it Nicky!” Vinnie exclaimed.

Michelle’s fingers hesitantly explored the opening in Nicky’s flies and soon found sleek, hard flesh. She curled her fingers around Nicky’s long thick cock and felt him shudder against her. She began to stroke him inside his pants, in the futile hope that he would climax before he made her do anything more degrading.

Nicky broke their kiss and took Michelle by the shoulders and eased her away from him a little.

“Take it out; I want to see you take it out,” he whimpered, his lust evident.

Michelle’s painted fingernails plucked at Nicky’s belt.

“Please don’t make me do this,” she begged, pretending to be despondent.

“Take it out bitch! You know what to do you putta,” Nicky sneered.

Michelle opened the waistband of Nicky’s trousers and his pants fell down around his ankles. His cock sprang upright between them; the tip of his purple glans glistening with silvery pre-seminal fluid peeked from the hood of his foreskin. Nicky’s cock was enormous, at least ten inches long, pink and thick. His foreskin stretched around the bulbous glans. The dark turkey-skin of his scrotal hung down between his legs; a musky odour floated up from his crotch and invaded Michelle’s nostrils.

Michelle gasped but Nicky had no time for her theatrics; he took her hand and placed it on his manhood and watched as Michelle gently wrapped her fingers around it; her ruby-red fingernails contrasting with flesh of his shaft. She slowly eased her fingers down the shaft, pulling back the foreskin, and exposed Nicky’s glossy purple glans. The musky aroma intensified.

Nicky pulled Michelle back against him and pressed his mouth to hers, kissing her passionately. She resignedly stroked Nicky’s enormous phallus; it stuck out from his groin between their bodies, throbbing in her fingers.

Nicky relished the feathery feel of her fingers loosely caressing his turgid member; it was about all he could stand without coming. Michelle didn’t realise it but she was prolonging her own torment. If she simply gripped his penis and gave it a few hard strokes Nicky would be unable to control his orgasm.

He reached down and firmly disengaged Michelle’s fingers from around his shaft.

“I don’t wanna come yet honey,” he panted into her mouth and then pressed his lips against hers again.

Nicky pulled Michelle’s against him enjoying the feel of his cock against material of her skirt. He held her body against his with one hand and his other hand slid down her body and rested on her buttocks. Michelle’s gasp was muffled by Nicky’s savage kisses, his lips grinding against hers and his tongue invading her mouth.

Nicky roughly fondled Michelle’s buttocks and the material of her skirt slid effortlessly across her plump rear, her skirt slithering against her satin panties.

Vinnie had taken out his penis and was slowly improving his erection as it stood out proudly from the flies of his suit pants.

Nicky’s erection was at full tumescence too as he humped up against the front of Michelle’s skirt and squeezed her buttocks through the layers of satin.

He slowly started to lift her skirt up. Michelle tensed but forced herself not to resist when Nicky lifted her skirt up around her waist.

Michelle stood on her tiptoes, raised up on her high-heels, leaning slightly forward, her arms around the large solid man, she hesitantly returned his kisses; her skirt rucked up around her waist. Nicky caressed her tight pantied buttocks.

Nicky’s cock was rubbing against the front of Michelle’s satin panties sending waves of pleasure through his body. He reached down and took Michelle’s hand and guided it to his rock-hard member.

“Slowly,” he groaned into Michelle’s mouth.

She understood what he meant and took the hard pulsing flesh in her hand and softly squeezed it until she felt Nicky buck against her; she ever so slowly began to masturbate him. She was surprised by the girth of his member and the by heat radiating from it as it pulsed in her hand; it was at least as big as Frankie’s. She masturbated him with long slow strokes, establishing a steady rhythm. Nicky moved his groin back and forth in time with her strokes, fucking her hand.

After a few minutes of intense stimulation Nicky walked Michelle backwards until she felt the edge of the table against her legs. He pushed her down so that she knelt in front of him, her hand still stroking his enormous member. Michelle knew what he wanted; she knelt on the filthy carpet awaiting her fate.

Nicky removed Michelle’s fingers from around his cock; it stood out from his body, proudly erect, quivering inches from her eyes. Pulsing veins encircled the meaty shaft and a silvery thread of pre-cum oozed from the eye of his glossy purple glans and dripped down into her lap, soaking into the gauzy material of her skirt.

Nicky put out a hand and pulled Michelle’s face towards his erection and thrust his hips forward until his glans touched her lipsticked lips. Michelle tentatively flicked out the tip of her tongue breaking the string of pre-seminal fluid that hung from Nicky’s cock.

Nicky gasped as Michelle began to slowly lick his cock. She worked her tongue around the bulbous head until it glistened with her saliva and then she ran her tongue up and down the shaft concentrating on the delicate fraenulum where his glans joined the shaft of his penis. Nicky watched the attractive transvestite attend to his phallus with her tongue. He stood this for a minute or two but then became impatient and pushed his cock against her lips signalling his need.

Michelle understood and resignedly took a deep breath and opened her mouth as far as she could, and allowed Nicky’s massive penis to push over her lips and inside her warm moist mouth. She concentrated on her breathing as about six inches of his penis slid into her mouth and then she began to gag.

Nicky eased himself out of her mouth a little until she had her gag reflex under control and then he began to leisurely fuck her face. Michelle submitted and stretched her lips around his shaft and slavered at his glands with her tongue; her aim was to induce Nicky’s orgasm as soon as possible and get the ordeal over with.

Nicky was close to coming but he didn’t want to orgasm just yet. He pulled his cock from Michelle’s mouth with audible plop and it wobbled menacingly in front of her eyes.

“You better get over here Vinnie if you want some of this!” Nicky said to his partner.

Vinnie’s long thin cock was sticking proudly out the front of pants; the sleek shaft and glans glistening from the saliva he had used to lubricate it whilst masturbating, watching Michelle fellate Nicky.

“I’m coming over now for my piece of the puttana,” Vinnie said.

Vinnie put his strong hands under Michelle’s armpits and lifted her to her feet. He pushed his face onto hers and began to kiss her passionately.

Michelle, dazed and degraded, allowed her survival instincts to kick in and she responded in kind, kissing Vinnie and suckling his tongue.

Nicky moved behind Michelle, and hitched her skirt up around her waist, and admired the view: Michelle’s buxom buttocks clad in the white satin panties, her legs encased in diaphanous nylon and feet shod in the sexy cork pumps. He stroked her buttocks through her panties.

Nicky pushed Michelle’s knees apart so that that he could position himself between her legs with his immense cock resting on her panty-clad buttocks. He lifted the panty material away from her crotch and slid his cock inside so that it rested in the crease of her buttocks and slowly rocked back and forth, dry-humping her.

Michelle felt Nicky’s huge penis rubbing against her rear and realised that soon Nicky would no longer be happy to dry-hump her and would try to penetrate her. The thought of that monstrous cock invading her unlubricated rear passage was horrifying and she made one last attempt to induce his orgasm. She pushed her backside out and began to pump back and forth in time with Nicky’s thrusts.

Vinnie felt Michelle’s movements and broke their kiss so that he could see what she was doing.

“Jesus this tranny putta is hot for it!” Vinnie said and pushed down on Michelle’s shoulders, forcing her down so her face was level with his crotch.

Vinnie pushed forward and Michelle had no choice but to open her mouth and allow his cock to slide into her mouth.

Vinnie was careful not make Michelle choke or gag; he could feel her lips close around the shaft of his cock and her tongue flutter against his glans. So long as she capitulated, he didn’t want her to choke and try to spit him out. He was happy that this piece of ass was sucking on his hard cock and didn’t want to spoil the sensations he was receiving from her attentions. He humped Michelle’s face slowly back and forth allowing his climax to slowly build.

Michelle’s movements were contributing to Nicky’s pleasure as he enjoyed the feel of her soft satin and nylon encased buttocks pushing back and forth along the underside of his member but knew that he couldn’t keep this up for much longer. He guessed that Michelle was trying to get him to ejaculate before he could fuck her but he had other plans.

Nicky quickly pulled his cock out from between her buttocks and spat into his hands; he lubricated his cock with the spittle. He lifted the gusset of Michelle’s panties away from her buttocks and ripped open her pantyhose. He positioned the head of his penis against her puckering anal bud and pushed hard.

Despite the lubrication Michelle screamed as her sphincter and the walls of her anus stretched to accommodate the huge phallus invading her back passage. When Nicky had the full eight inches of his cock buried inside Michelle he stopped pushing and his hands gripped her bucking hips as she tried to expel his penis.

“Keep still bitch; relax!” he ordered and slapped Michelle on the buttocks.

Through the searing pain Michelle knew that Nicky was right. The only way she would be able to accommodate the huge organ inside her without excruciating pain would be to relax her rectal muscles. She concentrated on doing just that.

Nicky felt the Michelle’s anus slowly relax. He pulled his cock out of her until just his glans remained inside her sphincter; he dribbled more spit onto his cock and then slowly began to fuck her.

Michelle felt Nicky withdraw, and then slowly fill her again; this time the passage of his member eased by the lubrication provided by his spit. Her back passage still burned and ached as Nicky fucked her but at least the pain was tolerable.

Nicky grasped the sides of Michelle’s panties and began to ride her, his cock slamming in and out of her tight ass. Nicky got into a steady rhythm pounding in and out of Michelle’s back passage and Michelle progressed through feelings of intense pain and numbness; until miraculously; a feeling of fullness that was not unpleasant combined with small waves of pleasure emitted from a source just inside her anus.

Nicky’s penis was stimulating her prostate; his shaft was also stimulating the sensitive nerves of her sphincter. Surprisingly she felt her own cock thicken in the front of her satin panties.

Nicky pulled at the waistband of Michelle’s panties as he rode her, thrusting back and forth against her, he was unintentionally stimulating her. Her panty crotch rubbed back and forth across her penis and Michelle let out an animal groan from deep within her throat.

Vinnie watched his accomplice fuck this sexy travisto and realised that he wouldn’t be able to hold back his orgasm much longer as he watched the bitch not only let his colleague fuck her; she was enjoying it.

Vinnie lifted Michelle’s face to his erect penis and without any encouragement; she engulfed it in her mouth, her lips sucking at the shaft and her tongue feathering along the sensitive glans. He would be coming soon he realised as he began to fuck her face.

The two mobsters and transvestite got into sync; their thrusts orchestrated with Nicky pounding himself in and out of Michelle’s soft sexy buttocks and Vinnie plunging his cock in and out Michelle’s red lipsticked lips. Michelle rocked back and forth in time with their thrusts, she couldn’t deny that she was enjoying being spit-roasted as her own cock pulsed inside her panties and rings of pleasure radiated out from her back passage.

Nicky pulled Michelle’s buttocks back hard against his groin; he pushed forward with all his might forcing every last inch of his cock deep inside her. Michelle pushed back against him as she felt his hot ejaculate fill her rectum. At the same time Vinnie groaned and his cock pulsed in her mouth flooding it with musky semen that she swallowed and savoured.

Some of Vinnie’s spend dribbled past her lipsticked lips and ran down her chin and she could feel some Nicky’s issue seep past her ravaged sphincter and run down her thighs and soak into her pantyhose. Michelle’s own orgasm rocked her and she ejaculated; flooding her panties with hot seed.

Michelle moaned around Vinnie’s phallus as he ejaculated the last of his issue in her mouth; Nicky and Vinnie both gasped and groaned as they emptied themselves inside the transvestite whore impaled between them. Nicky could feel Michelle’s anal muscles spasm and her sphincter contract, milking him of his seed; whilst Vinnie felt her lips slither and slide up and down his shaft while her tongue slathered at his glans extracting every last drop of his spend.

Eventually all three of them began to descend from the pinnacle of their orgasms. Vinnie recovered first and pulled his cock out Michelle’s mouth and rubbed it over her face in one last gesture of humiliation. A few droplets of sperm mixed with Michelle’s makeup, her face now a mess of lipstick rouge and mascara. A long gobbet of semen was drying on her cheek. The humiliating gesture was not lost on Michelle even as she greedily lapped at the slowly deflating member.

Vinnie pulled himself away from Michelle and began to pull up his pants.

“You are a real putta. You pretend you don’t like it; but you are really just a whore!” he laughed as he zipped his fly.

Nicky pulled his cock from Michelle’s anus with an audible plop. His semen ran in a rivulet from Michelle’s anus down her thigh and soaked in the nylon of her tattered pantyhose. Nicky wiped his cock on her panties and then pushed Michelle facedown on the floor.

Vinnie was dressed and anxious to leave. It was dark now and the temperature had dropped significantly.

“Let’s get outta this shithole Nicky; I’m freezing my ass off now I finished with the femminielli puttana,” Vinnie hopped up and down on the balls of his feet trying to keep warm.

Nicky adjusted his clothing and put the pistol next to Michelle’s face. She was huddled on the floor shivering, rearranging her tattered panties and hose.

“Shall I put one in her,” Nicky waved the pistol menacingly.

“We already both put one in her,” Vinnie laughed.

“Nah! Leave her to freeze. When Frankie finds her frozen solid with your load hanging outta her stronza like a Popsicle he’s gonna be even more pissed off than when we rob him,” Vinnie turned to leave.

Nicky threw Michelle’s bolero jacket over her.

“Sorry honey but this is it for you,” Nicky turned and began to walk away from her.

Michelle huddled on the filthy floor, already shivering uncontrollably knowing that she was done for. She had hoped that by giving the mobsters the information they wanted and by letting them fuck her they might have shown her mercy.

She had one last card to play.

She scrambled to her feet and ran to the door pulling on her jacket; Nicky and Vinnie were about to get into the LTD.

“I know the combination!” she yelled across the snow-strewn wasteland.

Nicky and Vinnie looked at each other across the roof of the car and then turned to Michelle.

“What the fuck?” Vinnie looked quizzically at Nicky.

“The safe! I know the combination to the safe,” Michelle called out.

“You’re bullshitting. You’d say anything to save your ass,” Nicky yelled back.

“Who do you think puts the takings in the safe every night you dummy!” Michelle yelled back; her arms wrapped around her as she shook with cold.

The mobsters looked at each other again.

“Take me back to New York and I’ll give you the combination to the safe. If I’m lying you can always whack me later,” Michelle tried to sound as confident as possible.

“Why don’t I just stick this pistol up your culo and make you tell me now,” Nicky called back at her.

“But you wouldn’t have me working for you inside then. Someone to turn off the alarm, someone to let you in and open the safe,” Michelle played all her cards.

The guys thought about it for a second or two.

“Go get the cooze Nicky. If what she says is right then this job just got a shitload easier,” Vinnie said.

“And if it ain't?” Nicky asked.

“Then it’s the East River for her,” Vinnie shrugged his shoulders.

Nicky’s feet crunched in the snow as he went back to hut and helped Michelle to the LTD. Vinnie turned up the heater as they began the drive back.

“Ok start talking bitch. Tell us again how you gonna make this easy for us and why?” Vinnie lit a cigarette and drove the car.

Michelle made her pitch effectively handing Vinnie and Nicky a perfect crime and as a consequence setting up an internal gang war inside the Bonanno Family.

The car had warmed up considerably and Michelle took off her jacket and smoked a cigarette. She smoothed her cum-stained skirt down her tattered pantyhose-clad legs and put out her cigarette as scrambled for makeup in her purse.

Nicky watched her in mirror on his visor. The tranny cooze was sexy despite the mess she was in. He watched her carefully apply her lipstick to those luscious lips. He started to climb between the front seats into the back of the large limousine.

“Where the fuck are you going?” Vinnie asked.

“I'm going to get my bricole sucked. When I’m finished pullover and I’ll drive while you fuck her. It’s two hours back to the city so we might as well entertain ourselves,” Nicky said.

Vinnie just chuckled and concentrated on driving; he glanced up in the rear view mirror and saw Michelle seemed more than happy to blow his friend. He adjusted the growing erection in his pants and looked forward to putting it between the tranny cooze’s asscheeks.

Nicky climbed onto the big bench seat in the back of the LTD. He wasted no time in pulling down his pants and exposing his penis.

Michelle resigned herself to having to perform sexually again for the men.

Nicky pulled her to him and kissed her passionately. He pulled Michelle down on the seat and lay on top of her

“Nicky I’m not sure I’m up it for it so soon…Oh my!” Michelle's refutation suddenly changed to acceptance as she felt the hot sleek skin of his member brush against her nyloned thigh.

“Mmm,” she moaned and reached down inquisitively to touch it.

It felt warm and smooth and the tip was slippery with precum. She gripped it gently and she smiled when she felt Nicky shudder with pleasure. She rubbed it against her thigh as Nicky began to thrust against her. Her own penis was erect and she could feel her panties becoming wet again.

Nicky pulled Michelle closer and she opened her legs a little wider and began to thrust his cock against her satin panties.

They both moaned.

Michelle let Nicky hump away at her panty crotch; she enjoyed the feeling of his hard cock against her body and their kissers were passionate and delightful. The carnality and sensuousness was very erotic knowing that Vinnie in the front of the car could see everything they were doing.

“Mm. This is wonderful Nicky but isn’t there something you came back here for?” Michelle smiled up at him.

Nicky was momentarily disappointed when Michelle extracted herself from beneath him but his disappointment turned to joy when she dropped to her knees.

Michelle was at eye level with Nicky’s erect penis. She took the phallus in her hand and was rewarded with a gasp of pleasure from Nicky and the sensation of it pulsing in her hand and a globule of clear precum extruding from the eye.

Michelle tentatively licked at the droplet; it tasted sweet and a little salty. She licked at the fraenulum underneath the head of Nicky’s cock and his penis quivered again and another droplet of pre-ejaculate appeared. She smiled and licked at the viscous fluid.

“Oh god Michelle that is so good!” Nicky moaned and placed his hands lightly on her head.

As Nicky gently pushed on her head Michelle opened wide and swallowed Nicky’s turgid member and then clamped her lips on the base of his cock and began to suck. She slavered at the shaft and glans of Nicky’s cock as she moved her mouth up and down on it.

She felt very controlling and highly aroused. She was tempted to slide a hand inside her panties and stroke herself but she didn’t think the guys would appreciate her doing so. Michelle used one hand to gently massage Nicky’s scrotum while the other grasped the base of his penis as she sucked it.

Nicky’s was trembling and his moans were getting louder and Michelle smiled around his cock. She had turned the tables! She had the power over him. She was the one who decided whether or not he orgasmed or whether she just teased him. It was exhilarating, empowering and sexually exciting.

Michelle lightly clasped Nicky’s scrotum and caressed his testes and squeezed the base of his penis with her other hand and worked her mouth up and down his huge cock faster and faster sucking his throbbing shaft and using her tongue on his glans.

She was rewarded with a mouthful of creamy semen. She sucked and slavered at the throbbing member, draining Nicky of his seed and swallowing the glutinous spend as he ejaculated into her mouth.

When Michelle had depleted Nicky of his load she took his penis out of her mouth and was satisfied to see one last small gobbet sperm dripped from the eye as she squeezed it and she licked it up and swallowed it with relish.

Michelle looked up and saw that that Nicky was looking down at her pretty face with affection as opposed to the disdain and contempt that he had shown her not that long ago.

Vinnie was hot for it, having watched Michelle fellate Nicky with gusto.

He pulled over and scrambled into the back while Nicky took over the driving duties.

He wasted no time and pulled Michelle onto her knees on the back seat and lifted her skirt. He opened his flies and freed his hard cock then he rolled Michelle’s pantyhose and panties down her thighs and stroked her buttocks. Michelle wriggled her ass to further entice and arouse him.

Michelle felt Vinnie gently rub the tip of his finger against her sphincter and she tensed up.

“Oh you don’t want to do that, doll,” Vinnie chuckled.

He spat in his hand to lubricate his finger. He took his time working his finger around her anal bud until he felt Michelle relax. Michelle couldn’t help but enjoy the sensation of the finger slowly circling and pressing against her sphincter; it felt so good.

Vinnie was gentle and worked the finger very slowly inside Michelle's anus ensuring it remained well lubricated. He searched for and found her prostate and Michelle gasped as he pressed his fingertip against the sensitive gland and slowly massaged it.

“Oh god!” Michelle groaned and felt her cock begin to leak precum.

Vinnie massaged Michelle's prostate until she began to wriggle her bottom in appreciation and then he slid a second finger inside her and Michelle gasped and wriggled harder against his hand.

“Oh wow that feels so good!” she gasped.

Little waves of ecstasy emanated from the spot that Vinnie was massaging and her cock was getting harder and dribbling pre-seminal fluid. She couldn’t help herself and she reached under her skirt and began to stroke her erection and relax her sphincter and allowing Vinnie to pleasure her with his fingers.

Vinnie took his fingers out of Michelle's anus and spat into his hand and greased his manhood.

Vinnie slowly pulled Michelle back onto his stiff rampant cock until his glans nestled against her sphincter. He guided his cock into her tight crevice. Michelle bit her lip as Vinnie’s cock forced its way past the tight bud of her sphincter.

Some of Nicky’s semen was still inside her and it added to the lubrication and Michelle forced herself to relax and wriggled her backside until Vinnie’s cock began to feel comfortable inside her. She still felt immensely full, but she no longer felt the pain she had experienced when he first entered her.

Vinnie smiled as Michelle relaxed her internal muscles and allowed her anus to accommodate his swollen penis. He thrust forward and back slowly at first and then he began to slowly plunge his cock in and out of Michelle’s anus. Michelle raised her buttocks and gripped the car seat as Vinnie began to fuck her.

Vinnie fucked Michelle with long slow strokes, Vinnie’s spit and Nicky’s semen lubricated Michelle’s back passage and helped her to relax her internal muscles. Michelle got into the rhythm with Vinnie and now that the pain had gone she felt quite comfortable as Vinnie slowly fucked her.

Michelle adjusted her position slightly so that Vinnie’s glans massaged her prostate as he drove his cock slowly in and out. She matched the pace of his thrusts and rocked back and forth on her knees in time with Vinnie as he fucked her.

Michelle could no longer pretend to herself that she was not taking pleasure from the sex; she liked it very much.

Vinnie began to quicken the pace and Michelle matched him thrust for thrust. His crotch made loud slapping sounds as he slammed against her thighs and buttocks, Michelle fucked him back, timing her thrusts to meet his.

“Mmm I’m coming in you; you tranny putta!” Vinnie groaned.

Michelle felt her back passage flood as Vinnie ejaculated inside her. Michelle could feel the hot sperm filling her as Vinnie’s cock convulsed. She felt a little ashamed that she felt so much pleasure; she been used and abused by both of these men but she was now a wanton whore, enjoying sucking cock and being fucked by them.

Michelle pushed her buttocks back into Vinnie’s crotch, her anus milking him of his seed. Warm semen dripped from her back passage as Vinnie’s glans pressed against her prostate in the final throes of ejaculation.

Michelle felt her own penis convulse as undulations of extreme pleasure emanated from her anus. She ejaculated and spent her seed, the delectation and gratification so intense that her knees buckled and Vinnie had to hold her up as the last of the milky load from her throbbing cock dribbled onto the back seat.

Michelle cleaned up the mess she had made on the seat and dabbed at her buttocks with a handkerchief and then she adjusted her clothing as best she could. The car reeked of sex. Vinnie got dressed and had Nicky pull over and he joined him in the front seat.

They smoked and went over the finer points of the robbery they were going to commit until the car pulled up outside the discrete entrance at the side of the building where she lived above the Gentlemen’s Club.

“We’ll be seeing you soon honey,” Vinnie said to Michelle as she alighted from the big car.

Michelle scampered up the stairs without being seen and tore off her ripped and tattered underwear and semen stained clothing and took a long hot shower. She brushed her teeth and gargled with mouthwash, fixed her makeup and hair and slipped into clean underwear. She dressed in a silk robe, poured bourbon, lit a cigarette and lay down on the couch and contemplated what she had done.

A wicked smile crossed her lips.

To be continued

Michelle Clooney met with Linda Gordon in her pokey flat down at Hunts Point but told her nothing what had happened at the Pine Barrens. Far from it; the way Michelle told it, she had met Nicky ‘The Wop’ and Vinnie Boccia at a coffeehouse in Little Italy and they had hatched their scheme there.

“So you have arranged for Nicky and Vinnie to hit the Gentleman’s Club while there is no one there but you?” Linda looked incredulously at Michelle.

“Frankie ain't stupid; he’s gonna think straight away that it’s an inside job,” Linda warned.

“Not when he finds his precious goomah beat up and trussed; maybe a little fucked,” Michelle grinned wickedly.

“You wouldn’t!” Linda blurted.

“Hey Linda; you know what happens to chicks who steal from the mob! Remember Irene Valasso?” Michelle replied.

“But jeez Michelle; you’d let those guinea’s fuck you to make it look like they raped you?” Linda was still a little sceptical.

“Anyway, just let the Feebs know that the robbery will go down very late Sunday night or very early Monday. Frankie should find me tied up in my office when comes into the Club in the morning,” Michelle explained.

“I’ll tell Frankie that it was Nicky and Vinnie that took his money and roughed up and fucked his goomah. If that doesn’t send the Family to the mattresses nothing will.”

“But what about Nicky and Vinnie? Why do they think you are helping them? Why won’t they just clip you after you open the safe for them?” Linda was puzzled.

“Those two goombahs think that I hate Frankie; that he treats my like shit so I want revenge. They think I’m worried that I’m going to the way of Irene Valasso when Frankie gets tired of me. Also the deal is we split the money three ways after Rusty Rastelli gets his taste,” Michelle grinned and lit a cigarette.

“It’s the nineteen seventies honey; the Mustachio Petes have long gone. These modern barones are more than happy to cut a business deal with a ragazza. Besides, to them, I’m a femminielli cooze with a braciole, so not technically a woman.”

“Jeez Michelle you speak mobster better than most of the goombahs,” Linda laughed.

“I’m supposed to tell Frankie that I didn’t recognise the guys who knocked over the safe; that they were wearing disguises, so Nicky and Vinnie are fine with the plan.”

“But you better make sure the Feebs are on the ball and ready to save my sweet ass if it goes pear shaped,” Michelle stubbed out her cigarette and started to gather her things.

“You going somewhere babe? I thought we might; you know, fool around,” Linda reached out and tickled Michelle’s thigh.

“I suppose I can stay for a little while,” Michelle grinned.

She dropped her things and began to unbutton Linda’s sweater-dress; underneath she was wearing a satin full-slip, panties, bra and pantyhose. Linda reciprocated and stripped Michelle out of her hotpants, and boots.

The two women began to grope each other but Linda broke their foreplay and led Michelle over to her bed so they could get comfortable. They lay side by side and kissed each other languorously taking their time to explore each other’s bodies. Michelle slipped her hands inside Linda’s full-slip and caressed her breasts, teasing the nipples with her fingertips. Linda reciprocated sliding her hands inside Michelle’s padded bra, stroking her tiny breasts and tweaking her nipples making Michelle gasp.

Michelle pulled off her blouse and unhooked her bra leaving her dressed only in her pantyhose and satin panties; she helped Linda take off her slip and she too was left in only pantyhose and panties. Michelle fell on Linda and kissed her and her small taut breasts pressed against Linda’s large pillowy bosom.

Michelle’s hands wandered down Linda’s body and she raked her fingers along Linda’s legs, caressing her through her sheer pantyhose. Her fingers explored the top of Linda’s thighs and slowly edged to her sex. She found her damp and warm, the diaphanous nylon soaked with vaginal secretions.

Linda’s hands squeezed Michelle’s nylon-encased buttocks and thighs. Linda fluttered her fingers along the top of Michelle’s legs then up her torso and across her lower belly teasing her. Michelle shuddered and Linda smiled. As Michelle’s fingers found her labia so Linda touched Michelle’s erect penis, Michelle’s pantyhose were also wet where her cock was leaking precum.

Panties were quickly removed and discarded as the wanting intensified and lust overcame languidness.

Michelle pushed her finger into Linda’s sodden cunt, caressing her clitoris thorough the translucent fabric; Linda squeezed Michelle’s cock though her gauzy nylons.

Michelle removed her hand from Linda’s sex and took Linda’s hand from her penis and she pushed her nylon-encased cock against Linda’s pantyhose-clad cunt. The women arched their backs and rutted against each other, grinding and squirming to provide maximum pleasure to each other. They were kissing hard, sloppily smashing lips and lashing tongues and they grunted and groaned with lust.

Linda reached between their bodies and pulled at the crotch of her pantyhose with her fingers until she tore a hole allowing Michelle’s cock access to her cunt. Michelle pushed her cock into Linda’s sopping vagina, her nylon-encased glans entered Linda’s cunt and they both shuddered with delectation.

Michelle pushed harder and her cock broke through the sheer pantyhose and freed of the restriction buried itself inside Linda’s slick tunnel. They both groaned.

Michelle began to slowly fuck Linda, ensuring her pubis pushed against Linda’s clitoris, their pantyhose thighs rubbing together adding to the sensations. Linda rose up to meet Michelle’s thrusts and she ground herself against Michelle for maximum stimulation.

Michelle felt her orgasm approaching and she quickened the pace, fucking Linda with long hard strokes as Linda pushed herself up off the bed to meet Michelle’s thrusts.

Michelle locked her legs under Linda’s and drove herself all the way inside her and squirmed and gyrated as she shot her load of creamy semen deep inside Linda. Linda kissed Michelle fervently, wrapping her arms around her and gasped into her mouth as she came. Her whole body shuddered with pleasure and gratification.

Michelle and Linda fucked and writhed as their respective orgasms climaxed and subsided.

Michelle left her cock inside Linda when their ardour had receded. They kissed, fondled and stroked each other, mewing and kissing.

Finally Michelle extricated herself from Linda’s embraces and started dressing. Linda lay on the bed dressed only in her ripped pantyhose smoking a cigarette.

“Now I really gotta go,” Michelle said as she pulled on a leather boot.

Come Sunday Michelle was nervous. The Gentlemen’s club closed early on Sundays and by ten o’clock in the evening Michelle had the place to herself. She had shooed out the girls saying that they could finish cleaning up on Monday morning.

Michelle’s mind was racing, thinking about what could go wrong. When she had finally convinced herself that all would be fine, she poured a large slug of bourbon, lit a cigarette and watched the clock.

Just before midnight she heard a soft rap on the imposing front doors of the Club and Michelle disabled the alarm and let Vincent Boccia and Nick Angelini inside. They were carrying two large canvas bags and had their burglary tools with them. Nick took Michelle in his arms and kissed her deeply.

“Cut that shit out Nicky; we got work to do first,” Vinnie growled.

Nicky and Vinnie were pros and they set about making it look like they had broken into the place. They jemmied the lock on the front doors and pulled out the wiring on the alarm. Nicky broke some furniture and glasses to make it look like a struggle had occurred.

“You know we gotta put a bit of a beating on you before we go toots?” Vinnie said apologetically.

“Of course; we gotta make it look real,” Michelle replied.

“And we gotta take advantage of you too,” Nicky grinned.

“Oh my! A poor girl like me is about to be ravaged,” Michelle lampooned putting her hands defensively to her breasts.

“Ok lets take it as wrote that you have forced me to show you guys the safe and let’s go up to my office,” Michelle led the way and Nicky couldn’t help but squeezing her buttocks as they climbed the stairs.

Nicky turned around and spoke to Vinnie.

“God this bitch is hot Vinnie. Can we take turns with her and then do the safe? We can role play it; make it more real,” he grinned.

Vinnie shrugged his shoulders as if to say ‘why not’.

Michelle overheard the conversation and knew what was coming.

“I can role play with the best of them,” Michelle giggled.

“Ok babe; we don’t wanna take too long here and get caught with our hands in the cookie jar so to speak so lets not fuck about too much with formalities shall we? Nicky pushed Michelle into the first-floor office.

“This is gonna be good; I’m gonna enjoy watching this,” Vinnie dropped into a lounge chair and lit a cigarette.

Nicky looked Michelle over slowly with hungry eyes. He looked down at her high-heeled pumps and followed her shapely; nylon encased legs exposed by the ankle-to-hip split in her teal satin evening gown. His eyes continued up the tight dress, resting for a few seconds on her small breasts pushing out the lustrous fabric. He gazed at Michelle’s face, lingering on her full plum-red lips, her heavily mascaraed eyes and her rouged cheeks framed by her ‘Farrah Fawcett’ do.

He quickly undressed; tossing his clothes into a pile with his pistol on the elaborate shoulder holster on the desk.

"Ok honey, we know you’re going to open the safe, but I wanna open something else first!" he grinned and pulled Michelle to him.

Nicky thrust his tongue into her mouth, crushing his lips against Michelle’s. He groaned and his hand went under inside her evening gown and he began to brutally squeeze her buttocks through the silky satin panties. Michelle felt his rock hard penis pushing against her though the silky fabric of her dress.

"Let’s see what’s under that dress!" he demanded.

"What’s that Nicky?" Michelle stammered, playing along.

Slap! Nicky's hand snaked out and backhanded Michelle across her cheek.

"Lift yer fucking dress Michelle; just do as I say!” he growled.

Michelle was a little taken aback. She did not expect it to get physical just yet but she knew that she had to be beaten a little to make it look like she had put up a fight.

Michelle reached down and took the hem of her dress in both hands and slowly raised it up her legs. Nicky's eyes followed as her firm thighs, encased in gossamer nylons, slowly came into view. He gasped as the first glimpse of black satin panty was exposed. He reached out and stroked his hand up and down her thighs; his callused hand slithering over the gossamer nylon.

"Mm Michelle, lovely," Nicky growled

He grabbed Michelle roughly and spun her around so that she was facing the couch. He pushed down on her shoulders and Michelle fell forward doubled over so that she was tottering on her heels. Nicky positioned himself behind her, kicking her heels apart.

Michelle wriggled her buttocks invitingly at Nicky. It might be role-play but she was looking forward to a good fucking.

Michelle felt Nicky lift her dress and push it over her back so that her silky buttocks were exposed and presented for him. She felt his engorged penis push against her pantied behind; it rubbed all over her satin encased buttocks. Then she felt his erection slide under the silken gusset of her panties and wedge itself in the valley of her fanny.

Nicky readjusted his member so that his glans nestled in the rosebud of Michelle’s sphincter. Nicky pulled the gusset of her panties across her buttocks so that he had an unobstructed view of his penis poised at her rear entrance; his erect member pushing against her bud.

Michelle had anticipated this and had her tube KY of lubricant at hand.

Michelle awkwardly reached behind her and felt around until her hand came into contact with Nicky's engorged phallus. It was rock hard and it felt enormous and menacing as it throbbed in her hand. Nicky looked down to see her standing legs wide apart on her high-heels, her legs encased in diaphanous fully-fashioned nylons and her black satin panties pushed to one side. He watched as her long delicate fingers, their red painted nails glimmering with the shine of the lubricant, slid feather-like up and down his hard cock, coating it with a generous amount of lubricant.

Michelle was enjoying the experience; she quite liked the naughtiness associated with being degraded and forced. She felt like she was nothing more than a whore; providing a receptacle for Nicky to empty himself into.

She felt the glans of his penis slide inside her tight anus, the lubricant assisting its passage.

"Oh!" Michelle groaned as the hard phallus slid past her sphincter.

Michelle was impaled on the head of Nicky's penis and he was groaning and gripping her so hard that she could hardly keep on her feet as her anus was assaulted.

Nicky's well-lubricated shaft drove itself all the way inside her. It was so big, and in her so deep that it knocked the wind out of her and rocked Michelle on her heels. Michelle felt Nicky's thighs against hers as his full weight pressed against her.

“Ok Michelle lets fuck,” he grunted

Nicky pulled her back against him and pushed harder as he assaulted her back passage as Vinnie sat watching. Nicky slowly thrust in and out of Michelle, hardly moving his cock more than an inch in and out; he leaned forward and kissed her neck then nibbled her earlobe. He stroked her thighs and groin as he slowly fucked her; delighted by the feel of slinky nylon and satin on his skin.

Nicky began to fuck her harder and faster, he breathed heavily, exhaling great explosions of breath as he established a hard and fast rhythm.

Nicky was thrusting against her, ensuring that he got all of himself inside her, rubbing his scrotum on her panty covered buttocks as he fucked her.

Michelle’s back passage was full and aching with the girth of the invading member as it slid in and out of her, but she began to feel the spongy hard mass of Nicky's glans as it pushed on her prostate. She smiled as the first ripple of sexual pleasure began to originate deep inside her.

She leant further forward so that her buttocks were presented to her assailant and she swayed her hips from side to side to increase Nicky's pleasure and ensure her nylon encased cheeks rubbed against him. Michelle turned her head so that Nicky could kiss her pouting lips.

Nicky pounded himself in and out of her and fucked her harder, grunting and panting with pleasure. He gripped her hips and pulled her back against him as he thrust forward and held her still jackhammering himself in and out of her, groaning and cursing.

"Michelle! Take my load!" he screamed.

Nicky thrust himself deep inside her and ground his scrotum against her satin-clad cheeks as he shuddered. Michelle felt his cock convulse inside her as it shuddered and secreted his hot spend. He held her tight, shuddering as his orgasm overpowered his senses.

Michelle was bent over the couch, her legs locked apart and her anus spasmed. She was close to orgasm but she knew that there was more cock to come.

Michelle felt Nicky’s cock slide out of her back passage and she fell forward onto the couch. She put the tube of KY jelly on the side table and took a handful of tissues and wiped herself. She slid her panties into place and stood up and stretched her legs watching Nicky get dressed and put on his shoulder holster.

Vinnie got out of the chair and stubbed out his cigarette.

“Ok. Now it’s my turn,” he sauntered over to Michelle.

Michelle opened her arms and Vinnie pulled her to him.

Michelle slid her tongue into Vinnie’s mouth and felt his erection rub against her through her dress. She manoeuvred a hand between their bodies and squeezed Vinnie’s penis through the material of his trousers. Vinnie groaned and pushed her onto the couch and fell down on top of her, never breaking their kiss.

His hand slid inside the split of her gown stroked her stocking-tops and the smooth, creamy skin of her upper thighs. His kisses were pleasant and she responded in kind; her penis was becoming tumescent again in her panties and when Vinnie lightly ran his fingers over the front of her panties she gasped and bit his lip.

“Mm you like that don’t you, you whore? I’m getting to like you puttanas that have little extra in their panties,” Vinnie whispered in her ear.

“And you are very beautiful and very sexy Michelle.”

He crushed his body against hers, his hands exploring her body as they kissed. Vinnie’s approach was the opposite of Nicky’s rough and ready fucking. Vinnie was tender with her, taking his time as he explored her, his hand slipped inside her dress and stroked her belly; occasionally dropping down and sliding over her erect penis encased in her satin panties. Michelle felt so wonton, so slutty, so feminine; the need for release was becoming overwhelming. Michelle reached between their bodies and opened his flies and freed Vinnie’s cock from the prison of his trousers; it felt long, thick, and meaty.

The feel of silk and satin caressing her body, the stockings encasing her legs, the taste of lipstick and makeup, the smell of her perfume and the feel of the hard bodied man against her excited Michelle. Michelle pushed herself free of Vinnie’s embrace and lowered her face to his groin.

She knelt on the couch and tentatively licked Vinnie’s erection; then she kissed his bulbous glans and was pleased when he shuddered in expectation. She took the hard weapon into her mouth and suckled it, sliding her lips along the shaft. She lifted her lips from the turgid member and looked at the purple veins pulsing along the shaft and the engorged crimson glans; her lipstick was smeared on the shaft. Michelle looked up into Vinnie’s eyes and saw his lust. A feeling of power and sexual energy surged through her despite the fact that she was the one being used. She lowered her face and traced the veins in his throbbing cock with the tip of her tongue and was delighted to hear him groan.

She kissed his fraenulum and Vinnie pushed her mouth down onto his cock.

Vinnie massaged Michelle’s buttocks through her satin panties and then she felt him pull the gusset aside, exposing her puckered sphincter. A probing finger explored her tight bud and then she felt the cold slipperiness of the lubricant as a finger pressed against the entrance to her tight entrance. Vinnie had obviously found the KY.

As his finger slid past her sphincter she began to feel pleasure and pushed back, encouraging him to drive his finger deeper inside her, stimulating that special place. As she sucked and slathered at Vinnie’s turgid cock she realised that she was so excited and so wanted to be fucked again.

Michelle spat out Vinnie’s cock and she could sense his disappointment, but not for long. Michelle spun around and straddled Vinnie so that she was sitting astride him; her buttocks positioned above his rampant member.

She reached out and scrambled her fingers around the bedside table until she eventually found the KY lubricant and she slathered his phallus with the cold gel.

Vinnie didn’t even remove her panties; he simply pulled the gusset to one side and then slowly slid his entire length inside Michelle until his scrotum rested against her buttocks. Michelle grunted as Vinnie’s cock filled her, but she liked the feeling of the hard member crammed inside her and especially liked the tingling feeling emanating from her prostate whenever Vinnie’s glans rubbed against it.

Vinnie gripped Michelle by the hips and she began to ride him, slowly at first, stopping now and then to lower her face to his so they could kiss passionately whilst his throbbing cock was buried deep inside her. Michelle slowly increased the tempo and as Michelle rode him he held on to her hips and rose up and thrust into her as she impaled herself on his hard, thick cock.

Vinnie pounded away at Michelle as she rose and lowered her buttocks to meet his thrusts. She lowered her face to his and they gasped and groaned into each other’s mouths, their tongues entwined and their teeth occasionally cracked together with the ferocity of the sex. Vinnie had managed to shuck off his shirt and Michelle raked his chest with her nails.

The fucking became a frenzy, Vinnie jack-hammered his cock in and out Michelle’s tight anus and Michelle, impaled on Vinnie’s hard throbbing cock, clung to him and wriggled and shook her buttocks. She thrust her hips down to match his strokes ensuring his full length penetrated her slick anal sheath.

Michelle felt her orgasm approaching as Vinnie howled and moaned with the rush of his own climax. Michelle felt Vinnie’s cock convulse deep inside her as he filled her with his hot seed. Michelle’s cock was erect and rubbing against Vinnie’s stomach through the flimsy material of her panties as Vinnie savagely fucked her. The pressure and friction induced Michelle’s own climax and she groaned in ecstasy as she flooded her panties with hot semen. Vinnie’s cock pounded in and out of her anus further stimulating her and she was wracked by one of the most intense orgasm that she had ever experienced.

Vinnie’s thrusting slowed down as his orgasm subsided until eventually Michelle lay still on top of him with his slowly deflating penis buried in her anus. They continued to kiss and caress each other until Vinnie finally broke the kiss and smiled up at her.

“Ok doll; let’s get down to business,” Vinnie pushed Michelle off him.

He got dressed and put his gun back in his pants and grinned at Nicky who was drinking a tumbler of bourbon and smoking a cigarette. He was tenting his trousers.

“Again?” Vinnie pointed to the bulge in Nicky’s pants.

“Again,” Nicky grinned back at his accomplice.

“I wanna fuck her after we tie her up. That will be kinky,” Nicky chuckled.

“Let’s get the money before we do anything else,” Vinnie said, tucking in his shirt.

Michelle had cleaned herself up and had adjusted her clothing. She was applying lipstick, holding a compact mirror to her face.

“Ok doll-face; open the safe,” Vinnie instructed.

This was where Michelle was concerned that if anything was going to go wrong; it would. As soon as she opened the safe, she was effectively no longer of any great value to Vinnie and Nicky but she was confident that they kinda liked her now. Also they didn’t want to miss the opportunity to shame Frankie by letting it be known that they had fucked his goomah.

Michelle spun the dials and opened the big safe. Vinnie pushed her out of the way and whooped with delight when he saw the piles of cash.

“Pass me the bags Nicky,” Nicky passed over the canvas bags they had bought to take away the cash.

They filled the two heavy bags and closed them.

“Ok. We count the cash down at Toyland’s Social Club, give Rusty Rastelli his tribute and split the remainder three ways,” Vinnie said.

“You trust us don’t you babe?” Nicky pulled Michelle into his arms.

“You’re about to tie me up and fuck me again so I better,” Michelle smiled and leaned into Nicky and kissed him, locking her arms around his neck.

“But I don’t trust you! You fucking doublecrossing puttana!” Frankie growled.

Frank Caputo was standing at the door with his pistol drawn.

“It’s not what you think!” Michelle pleaded.

But it was too late.

Vinnie reached for his gun and Frankie shot him through the heart. Nicky flung Michelle aside so that he could get to his own weapon but he didn’t stand a chance and Frankie shot him twice in the face.

Frankie stepped into the office and poked at the corpses of Vinnie and Nicky with the toe of his boot to make sure they were dead.

Michelle lay on the floor sobbing, awaiting her fate. She could hear footsteps pounding up the stairs, most likely the FBI but they would be too late to save her.

“Why Michelle? Why?” tears were rolling down Frankie's cheeks.

Michelle instinctively curled up in ball and put her hands over her face as Frankie stood over her, pointing his pistol at her.

“Drop the gun Frankie,” Michelle heard an FBI agent shout.

Michelle heard two gunshots in rapid succession, and then a moment of searing pain before darkness engulfed her.

Michelle woke up in a hospital bed with drips in her arms and bandages around her chest. A machine beside her bed was monitoring her vital signs. A nurse came in and took the chart from the bottom of her bed and made a few entries on it. She refused to answer any of Michelle’s questions.

The nurse picked up the handset on the bedside table.

“She’s awake and talking,” the nurse said and hung up the phone.

“Fuck you too,” Michelle called after the nurse as she left the room.

“Well if it isn’t Tweedle Dum and Tweedle Dumber?” Michelle winced with pain as the two FBI agents who had initially sent her undercover entered the room.

“Your fucking so called surveillance team left me out to dry,” Michelle struggled to sit up.

“You’re still alive aren’t you?” the black agent replied pulling up a seat.

“Frankie?” Michelle asked; and the white agent slowly shook his head.

Michelle teared up. What she had with Frankie was far from love but there was certainly affection.

“Hey don’t cry. You did good, the Bonanno Family are in a state of civil war split down the middle between the followers of Rusty Rastelli and those loyal to Lilo Galante. That fuck Galante and his goombahs are holed up at his Toyland Social Club where we are hearing everything they say on the wiretap,” Black said.

“And with all the other intel you got for us while you were working for Frankie, we have a whole new insight as to how the five families are doing business,” White grinned.

“And me?” Michelle asked.

“Well…We are going to have to renege on our deal I’m afraid. Corrupt as New York’s finest are, some flatfoot will undoubtedly give you up if you go back working for the NYPD,” White explained.

“So looks like it’s Witsec for you. Even though you’re police, that won’t protect you from the mob if they find out what you have done,” Black elucidated.

“So where you wanna go Mitch?” Black grinned.

“Don’t call me that! Mitchell Clooney is dead. I’m going to keep my feminine persona and my first name. Let me think about it and I’ll get back to you,” Michelle replied.

“Well don’t think about it too long toots because as soon as you can travel we’re handing you over to the US Marshals and it’s gone baby, gone for Michelle Clooney,” Black replied and pulled back his chair.

Black and White left the hospital room and Michelle never saw them again.

In the fall of 1980, Detective First Grade Linda Gordon was off duty and lined up outside of the legendary nightclub CBGB hoping to get inside to see Blondie perform. She was wearing a white spandex miniskirt, a lace-sleeved bustier top, opaque black pantyhose and white spiked heels. Her hair was styled in a bouffant that took nearly a whole can of hairspray to hold in place and her heavy makeup was bright and bold. She had accessorised with large faux gold earrings and matching necklace and bangles.

She chewed gum and chainsmoked, hoping against hope that she would get to the front of the line before the concert started.

Linda looked on jealously as a large white stretch limousine with heavily tinted windows glided up to the curb. A black chauffeur in full livery got out of the car and opened the curbside passenger door.

A pair of long, elegant legs clad in sheer black pantyhose and gold high-heeled sandals swung out of the car followed by a curvaceous tall woman wearing a leopard-skin body-sheath that was split from ankle to hip on one side. Her firm pert breasts were openly displayed by the low-cut bodice; her blonde shoulder-length hair was crinkle styled, her makeup heavy but perfect and the gold jewellery that she was wearing was definitely not faux.

Linda was surprised when the woman looked her way and then started walking towards her. The woman reached out and audaciously took Linda’s hand.

“Come on honey; let’s not stand out here with the riff-raff,” she said with a sultry sexy voice, leading Linda to the entrance of CBGB.

The doorman lifted the red rope and nodded at the woman with deference.

An inkling of cognisance crossed Linda’s mind as she and the woman were escorted to a booth near the front of the club.

“I know you, don’t I?” Linda searched the woman’s face.

“Oh my fucking god! It’s you! It’s Michelle!” Linda screamed.

“Yes darling it’s me, Michelle Lawrence, formally Michelle Clooney and before that…well never mind,” Michelle grinned.

An ice bucket with a bottle of Moet and Chandon appeared and glasses were filled. Linda had to yell over the noise.

“What the fuck?” Linda circled a finger at Michelle’s body and looking questioningly at her.

“It’s a long and fascinating story,” Michelle grinned over her champagne.

“Well first off; they are real right?” Linda waved her champagne glass in the direction of Michelle’s breasts.

“The best money can buy girl,” Michelle grinned.

“What about?” Linda stared fixedly downward.

“Oh no honey I kept that. I could have had it, shall we say re-purposed, but I’m still attached to it,” Michelle laughed and Linda couldn’t help but join in.

“Come on Michelle…what about…everything?” Linda laughed but she obviously wanted to know what happened to Michelle.

“Ok well here is the potted history babe. First off I elected to keep my female persona and the Federal Government was kind enough to provide me with female identification documents under my new name,” Michelle began.

“I went into Witsec in San Francisco where the US Marshall Service thought my ‘type’ would be better accepted.”

“Then the surgeries. One after the other and some quite painful. I got these first,” Michelle hefted her breasts.

“Then a bit of facial feminisation, which also altered my appearance somewhat, then voice feminisation and a tracheal shave; whilst at the same time taking female hormones.”

“What you see before you took me over two years to put together along with some diet and exercise,” Michelle sipped her drink and winked at Linda.

“But who paid for all that? Surely the Feebs or the Marshals wouldn’t have funded any of it?” Linda was incredulous.

“Honey, remember the fate of Irene Valasso?” Michelle lit a cigarette and offered one to Linda.

Linda nodded.

“Frankie clipped her for skimming from the Club. So I checked out the books and with a bit of help I found out how she did it. I did it better,” Michelle grinned.

“Fuck! You skimmed Frankie's takings?” Linda was slack-jawed.

“Everything he put in the safe I took a piece of. Those FBI fuckers had me undercover sucking dick and fucking that gangster for over a year. Did you think that they had any intention of looking after me when I came out?” Michelle blew smoke at the ceiling.

“Those fuckers would have been happy to stick me in Bumfuck Idaho dusting library books or something, just so they could forget about me.”

“But darling you look so fabulous. You’re so confident and feminine. Fuck I’m envious of you,” Linda grinned.

“Honey I have my own fashion house now. I have to be confident,” Michelle responded.

Linda looked at Michelle sceptically.

“I’m making a fortune on the West Coast and I’m in New York to open a store here,” Michelle continued.

“But what about Witsec?” Linda asked hesitantly.

“Oh fuck Witsec! I blew that off right after my surgeries,” Michelle scoffed.

“Besides, Carmine Galante got whacked last year so who’s looking for me now; even if they knew who I was?” Michelle waved her hand.

“Now if you can excuse me honey I’m here to meet my business partner and she’s just arrived.”

Michelle stood and waved to a stunning looking woman who was winding her way through the crowd.

Rita Cordova waved back.

The End

Author’s note: Some of the characters and events in this story are factual regarding the NYPD and the New York Mafia during 1970s. The main characters are works of my own imagination.

Michele Nylons, September 2018