Pillow Talk Ch. 02

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.