Undercover Angel Ch. 01

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Mike goes undercover as a transvestite to escape crime boss.
5.9k words
4.37
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Part 1 of the 4 part series

Updated 09/22/2022
Created 10/22/2008
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MicheleNylons
MicheleNylons
3,915 Followers

When Mike Harris stole two point seven million dollars in cash from his employer, he knew that his life had changed forever. It's one thing to steal that amount of money from your bosses' safe; it's quiet another to steal it from a ruthless gangster who is heavily involved in narcotics, prostitution, gambling and murder.

Mike was Tony Leonardo's bookkeeper, accountant and financial adviser. Far removed from the seedy side of Tony's business, Mike laundered the money, hid it in offshore accounts and invested it in legitimate enterprises to hide it from taxman and law enforcement. Mike knew that on the fifteenth of each month a large bundle of untraceable cash was kept in Tony's office safe overnight; he suspected it was for drug buys or skimmed from Tony's illegal casinos and kept secret from the other crime syndicate bosses. The one thing he did know was that the cash that flowed through Tony's safe on every fifteenth of the month never made it any of Tony's books, either legitimate or counterfeit. It was untraceable.

When Mike made the decision to steal the money he realised that he had one slight advantage; Tony couldn't report the theft of the money through legitimate channels. Not that it made much of a difference; Tony had enough clout with his connections on both sides of law enforcement so that within hours of the theft being discovered the search for the thief would become an ever widening blanket over city, then the state, and then the whole country.

The main problem with stealing the cash from Tony's safe was that only Tony and Mike knew the combination, so it was not like Tony was going to have to perform any detective work to figure out who had stolen his money. Another problem was that Tony had connections everywhere; not just in the underworld, but connections in business, law enforcement, the government; everywhere! All of the connections owed Tony favours for one reason or another; they were on the take, being blackmailed, business partners, or they just liked to rub up against a high profile semi-legitimate criminal.

So whoever stole Tony's cash was going to have to go into hiding. Not just grow a beard and colour your hair in hiding; but completely disappear off the face of the world in hiding; your own mother wouldn't recognise you if she saw you in hiding. The person would have to; for all intents and purposes disappear.

Mike had been planning on taking the cash for a about a year now; he lived in a modest townhouse in a middleclass suburb; he had grown up an orphan and he had very few friends and very little social life. Mike had been snared in Tony's web about five years ago when he was caught embezzling a few thousand dollars a month from his employer, an Import and Export Company, that turned out to be one of Tony's semi-legitimate fronts. The manager of the company was impressed with Mike's ingenuity, he had been embezzling the company for over ten years without being caught, and he advised Tony accordingly.

Tony had made Mike an offer he couldn't refuse; he either worked for Tony as his bookkeeper, accountant and financial adviser or he would be introduced to one of Tony's associates who had a penchant for hot pokers, electric drills and pliers. The associate would ensure that Mike died screaming, damning his mother for ever giving birth to him. Mike accepted the offer.

Tony was smart at some things but dumb at others. He gave Mike just enough money to live a comfortable life, but not enough money to live the sort of life he wanted to. Tony had plenty of money and ordinarily a man in Mike's position would be extremely well paid for his work, but Tony was petty. He believed that Mike owed him for the money he had embezzled from the Import and Export Company so he paid Mike a pittance of what he was actually worth. So as well as being threatened with his life, Mike was also only being paid a subsistence wage. Mike harboured his resentment and waited for his chance.

Over the past five years Tony had become complacent; at first he wouldn't let Mike anywhere near the safe but Tony became lazy and eventually gave Mike the combination to his safe so that he had access to the books that were kept in there. Mike also played the toady to perfection; Tony was duped into thinking that Mike was happy with their business arrangement and his paltry wage. Mike was loyal, courteous and hard working; so why shouldn't Tony trust him? Besides there was no way an inky fingered, shiny-pant, accountant would dare to rip off Tony Leonardo!

Tony was in for a big surprise!

Mike knew that stealing the money was the easy part; getting away with it was going to be near on impossible. Having no friends or family meant that there was no one for Tony to lean on, but it also meant there was no one to help him. Mike knew that he would not be able to use any of his personal documents such as his passport, credit cards or drivers license, because he would immediately pop up on the radar. Air travel was out of the question; even domestic charter services wanted positive identification documents given the current state of heightened security. Any credit card transactions would immediately trigger a hit in cyberspace, immediately giving his whereabouts away. He also knew that he would need an excellent disguise; a disguise that was so good that no one would recognise him.

Mike had three vices that his acquaintances knew about. He liked to drink single malt scotch whiskey; he liked to smoke good quality cigarettes; and he liked to gamble. The gambling had led to his downfall. He had gotten himself into so much debt because of his gambling that he had started embezzling money from the Import and Export Company to feed his addiction. Even if he knew that the company was one of Tony Leonardo's fronts he probably would still have embezzled the money. The last five years had cured him of his gambling addiction but he still liked a glass of single malt and smoking cigarettes.

Mike had one vice that no one knew about. He was a closet crossdresser. He was more than that; he was a closet transvestite. He had been dressing as a woman in the privacy of his own home for so long that he had perfected the wearing of female attire and the application of makeup, feminine mannerisms and even had developed a smoky feminine voice. Mike had been a crossdresser for as long as he remembered. In the few foster homes where he had stayed for short periods of time as a child he had worn his foster mother's and sister's clothing whenever he got the opportunity. From the earliest age he had been fascinated by the sheen of nylons on long legs, the swish of stockings rubbing together and the gentle rustle of satin slips, the flick of a hem against a thigh, the soft caress of a satin blouse, the click of high heels on a hard floor, and the taste, texture and smell of cosmetics.

Mike was not sexually aroused by women's clothing; he just felt completely happy and secure when he dressed as a woman. He had researched the phenomenon and had discovered that the majority of crossdressers were heterosexual males. He put down his penchant for crossdressing as something to do with being an orphan and never having had a mother's love. He didn't try to analyse it too much; he just did it. Most nights of the week in the privacy of his own home Mike dressed as a woman and just enjoyed it for the satisfaction it gave him; he just felt right when he was dressed.

When he dressed as a woman he a certain style that he liked; he did not like long pants, jeans, shorts, or pedal-pushers. He didn't like house dresses, t-shirts or plain tops. He hated sensible shoes and he detested bare legs. Mike liked to dress in a style he had developed for himself over the years. A-line or pencil skirts with splits or kick-pleats, business suits with tight skirts, silk or satin long sleeved blouses, nylon or satin slips, full cut or boy-leg nylon, satin or lace panties, heavy makeup and dark bobs or shoulder length wigs and high heeled courts, pumps or sandals. He always wore hosiery: stockings or sheer to the waist pantyhose.

As a boy in foster homes he had worn the underwear, hosiery and sometimes skirts and blouses illicitly borrowed from his foster mom or sister. He knew from an early age that this was a dangerous game and that he likely to get caught, so he repressed the urge to crossdress until he finally left the orphanage and went to university to get his degree. His one transgression in his early teens was in the orphanage when he was found by a nurse hiding down in the basement when everyone else was out playing sport. He was dressed in a pair of snagged pantyhose and nylon panties he had found discarded in the female staff dressing room. He wore a sarong and a t-shirt with rolled up socks pushed under the t-shirt to imitate breasts. He's combed out his shoulder length hair and painted his lips with red crayon and lined his eyes with a fine tipped black marking pen. The nurse had berated him but kept the incident a secret.

In university he shared a series of flats with other students and would dress up in his bedroom when no one was home; always with the door securely locked. He lost his virginity at eighteen to a female student and liked the sex enough to work his way though half a dozen girlfriends before he graduated. He never linked his crossdressing to sex and although he tried to influence to get his girlfriends to dress in a style similar to his own, they never really got into it. They were university students in the seventies and wore hippie clothes; peasant skirts, jeans, t-shirts and bare legs.

By the time Mike got the job at the Import and Export Company he knew enough about crossdressing to have put together an extensive female wardrobe, cosmetics, jewellery, wigs and accessories. He'd even purchased a pair of good quality breastforms from a sex shop. He had also developed a full blown gambling addiction. He spent his nights and weekends either at clubs, illegal casinos or the racetrack or at home dressed as a woman. By the time he was in his late thirties; both addictions had taken over his life and he had few friends or acquaintances. He gambled or he dressed.

The gambling had ceased when he went to go to work for Tony Leonardo but Mike's obsession with transvestism had not. He still had all of his feminine paraphernalia and dressed as often as he could. He kept his body trim and completely hairless and his nails were kept a little longer than most men, but they were very well manicured. He could transform from his male persona into his female persona in about an hour.

When dressed he would sit around and read ladies fashion magazines or just watch television or a DVD and later he learned how to use the internet.

Mike never went to the thousands of sex sites out there on the web; he still engaged in heterosexual sex of course, mainly with prostitutes, the thought of sex with either a woman or a man with him dressed as a woman never entered his head. When his web browser occasionally took him to sites where pictures of transvestites and crossdressers were having sex with men or other crossdressers he was quite repulsed.

He did visit online transgender support sites however and at one stage he even thought about joining the Seahorse Club, a heterosexual crossdressing group who met discretely to support one and other, but he decided against it. He didn't really need that sort of support; he was comfortable with his own identities. His male identity as Mike Harris, bookkeeper to the mob, and his female identity as Michele Nylons, closet transvestite.

Mike stole the two point seven million dollars in cash from Tony Leonardo's safe on the evening of July 15th; a cold bleak Canberra evening. He was surprised at how easily that amount of money fitted into his briefcase. As he was about to close the safe door he saw the two sets books, and on an impulse, he took those as well; they might come in handy later should he need to bargain with Tony. He drove home to his small townhouse and parked his small Corolla sedan at the curb; he would never need it again.

Mike had saved up his meagre wages for six months and had paid cash for a five year old Ford Falcon from a farmer who asked no questions and wasn't interested in completing the registration transfer papers. Mike had driven around the suburbs of Canberra in his Corolla for a few weeks and had randomly stolen number plates from cars registered in different states. After he bought the Ford home it had not moved from the garage; he had even filled the tank from a jerry can. The car waited for him in the gloom of the garage; his instrument of escape; loaded with what were now his only worldly possessions.

Determined, but forcing himself not to hurry, Mike went to his bedroom, turned up the heat and shaved and showered. He had laid out a travel outfit on his bed and his makeup and accessories were arranged on his dresser. All of his remaining female clothing and paraphernalia had been packed into two suitcases and locked in the boot of the car parked in the garage. His male clothing and anything to do with his male persona would be staying behind.

Michele worked quickly, applying her foundation and then liberally coated her face and neck with face powder one shade darker than her foundation. She applied her eyeliner, then a combination of pale blue and dark pink eye-shadow, and then lashings of black mascara on her eyelashes. Next she rouged her cheeks and completed the routine with a light coating of 'skin-glow' face powder. She applied her favourite plum red Maybelline two-coat long-lasting lipstick. She took some time to line her lips just outside of her lip-line so that her lips would seem fuller. She poured herself a scotch, lit a cigarette and painstakingly painted her toenails and fingernails a deep plum red before attaching her breastforms with medical adhesive and slipped into a white satin brassiere to hold them in place while she dressed. She used another piece of the adhesive to hide her penis underneath her crotch.

She brushed out a shoulder-length brunette wig with subtle crimson highlights and positioned the wig on her head and adjusted it so that her fringe was straight and hung level with her eyebrows. She opened a packet of Kaiser, flesh-toned, ultra-sheer, sheer-to-the-waist pantyhose and smoothed them up her legs and over her tummy and buttocks. She carefully manipulated the sheer toes around her painted toenails ensuring she didn't ladder them.

She stepped into a pair of white nylon full-cut panties and slid them up her thighs, savouring the rustling sound of the nylon panties rubbing on her pantyhose. She clipped silver earrings to her ears, placed a matching pendant around her neck and put on two silver bangles and rings on the two of the fingers of each hand. She chose a peach coloured nylon full-slip and pulled it over her head being careful not to spoil her makeup or hair. She smoothed the garment over her body, the tight bodice clung to her breasts and hips and the skirt flared around her thighs, occasionally clinging to her stockinged legs. She loved the feel of the lacy hem; like butterfly wings brushing on her thighs.

She slipped her feet into a pair of black high-heel pumps and then pulled on a slate grey pencil skirt with a kick pleat at the rear and buttoned herself into a mauve, long-sleeved satin blouse. She fastened the waist of the skirt and zipped up the side before pulling on the matching suit jacket. She adjusted the hem of her skirt and fiddled with her blouse and jacket. She gave her makeup a final touch up, brushed her hair and then sprayed herself liberally with Poison, her favourite perfume.

Michele checked herself in the full-length mirror and admired her ample but well-proportioned bottom; the pencil skirt was a snug fit. She drained her scotch; she would only have the one drink; she did not want to be arrested for dunk driving. She tossed her cosmetics and other accessories into a white cosmetics case and looked around the bedroom for a final check. She picked up the packaging from the pantyhose and dropped it in the waste basket without thinking and picked up her cosmetics case off the dresser and the briefcase off the bed and then left her townhouse forever.

Tony Leonardo discovered he had been robbed by Mike Harris at ten o'clock the next day; by then Michele was sleeping in a cheap motel a couple of hundred kilometres away.

Michele's escape did not go exactly as she had planned it. She was extremely nervous going out in the world for the first time dressed as a woman but she was in her car and it was dark and frosty winter night so there wouldn't be many people on the roads any way. She was confident that she looked feminine enough that no one would clock her behind the wheel of her car; the big test would come later when she would have to interact with people face to face.

She made it out of Canberra without incident and was soon on the Federal highway. The road was dark and there was very little traffic. She had to deliberately force herself to stay within the speed limit, her subconscious kept telling her to speed away from the scene of the crime. A couple of times she had to ease her foot off the accelerator and driving in her high heels for the first time was a little difficult.

Michele was feeling tired and the adrenaline rush and excitement of the robbery and the escape was wearing off; she was thinking about where she should stay the night when she saw blue and red flashing lights in her rear vision mirror. The police car gave a quick burst on the siren and flashed its high beam.

"Fuck!" Michele cried, and pulled her car over into a darkened deserted rest area next to the dry lake.

The police car pulled into the rest area and parked behind her, the high beams illuminated the inside of Michele's Ford. Michele's hands were visibly shaking on the steering wheel. She didn't know if she was more scared because it was her first encounter with another person as a transvestite or because Tony might have already discovered the robbery and the policeman might be working for Tony.

The door to the police vehicle opened and a police officer got out of the car and approached Michele's Ford shining a long black torch at her window as he approached. Michele rolled down the window; her heart pounding.

"Driver's licence please Miss?" the Federal policeman asked.

Michele fumbled in her clutch purse, panicking because obviously her driver's licence belonged to Mike Harris not Michele Nylons. She knew that the police officer would take a special interest in her because she was a man dressed as a woman and he had may even have been briefed to look out for Mike Harris. She knew she had to do something desperate to keep the policeman from looking at her licence.

"I could show you my driver's licence officer," Michele whispered in the sultry enfemme voice that she had been practicing over the years.

"Or I could show you something more interesting?" she smiled quizzically up at the officer.

The policeman looked to be in his fifties and was a little overweight but he had a handsome face. He glanced down at his watch and then looked at Michele, taking in her attractive, overly made-up face. He looked around at the deserted rest stop and then back at Michele and smiled.

"Turn off your engine and kill you headlights," he said and turned back to his police car.

The police car's flashers and headlights went off and when Michele turned off her own headlights the rest stop was almost pitch black. Michele could just make out the fence line along the edge of Lake George faintly illuminated by the starlight. The rest stop was briefly illuminated by the interior lights of the police car when the policeman opened the door and was then again pitch black when he exited the car and closed the door. The policeman crunched across the cold gravel and opened the passenger door to Michele's car and slid into the passenger seat beside her and closed the door.

MicheleNylons
MicheleNylons
3,915 Followers
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