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