Whores And Pimps Ch. 01

Angie applied a thick coat of foundation to his face and neck and then set it with a liberal dusting of matching face powder. She then went to work on his eyes. Next she brushed dark blue eyeshadow onto Malcolm's eyelids working from the inner corner of each eye to the centre above her pupils. She worked the powder upwards right up to his eyebrows and then she applied a coat of lighter blue out to the far corners of his eyes, lightening the makeup as she worked it up to his brows and blending the two shades where they merged.

"I'm no expert at hooker makeup," she said, "but I've seen enough movies to know that usually go for these garish colours. "Whatever," Malcolm said pretending to feign interest whilst paying close attention. Angie tut-tutted a little and reached for some pink eyeshadow and applied it liberally around the edges of the two coats of blue that she had already applied; blending the eyeshadow with a small brush and making final adjustments with her fingertip. Malcolm loved the effect and filed the snippet away for future use. "Ok brother; keep very still now and just close your eyes half-closed for me; here comes the hard bit; the eyeliner." She said, concentrating on her task. Angie applied jet black eyeliner to his upper and lower eyelids as close to his lash-line as possible. She started in the very corner of her each eye and worked outwards applying three coats and touching up where necessary so that his eyes were framed by the black makeup.

"Open your eyes; lift your head up but look down at my tummy and keep still for me sweets ok; I'm going to do your mascara next. I hope you are taking mental notes so that you can touch up your makeup during the evening." Angie said.

"What do you mean; touch up my makeup?" he asked; knowing full well what she meant.

"We girls don't stay looking good all night without touching up our war-paint you know" she giggled, "that's why we spend so much time in the john; why do you think we call it the powder room! I bought you some makeup yesterday that you can take with you tonight; you can give it to me later as you won't be needing it," she explained.

She applied plenty of thick black mascara to his upper and lower eyelashes; fiddling a little as she worked. She explained that as his eyelashes were very fine she had to apply lots of the product to get a good effect,

"I wish we had bought falsies," she muttered.

Malcolm laughed inside because he had three sets of false eyelashes at home.

"Ok nearly there," she sighed and took a sip of her drink.

Angie applied blusher to his cheeks, feathering it along his cheek-line and smoothing it up so that it almost merged with his eyeshadow. Then she dusted his whole face and neck with a coating of sheer-glow finishing powder, being careful not to smudge her mascara and eyeliner.

"Ok Malcolm I want you to play particular attention to how I do your lipstick; you will definitely have to touch up your lippy tonight," she lectured.

She opened a long slim box that contained two slim tubes and unscrewed the first tube to reveal a slim applicator coated with plum coloured liquid lipstick.

"This is the first coat and it is long lasting colour; be careful how you use it honey because it is really hard to get it off if you fuck up ok?" she instructed, "so pay complete attention and when you touch it up tonight make sure you don't go outside of the lip-line that I put on you."

Malcolm had never used a two-coat lipstick before; he just used ordinary cheap lipstick at home and he paid very close attention as Angie coloured his lips with the first coat of colour and then took the other tube which she screwed at the bottom to reveal what looked more like the lippy he was used to, but slimmer and it was clear not coloured. She waited a minute and then applied the clear top coat over the base colour coat.

"Perfect," she whispered more to herself than him, "now leave your lips parted for a second until its dry ok?"

Angie took the brunette wig off the wig stand and brushed it out while Malcolm sat still and let his makeup set and lipstick dry. After a minute or two Angie put the wig on his head and fiddled with it until it was sitting perfect with the fringe straight. She brushed it here and there and then stood back to admire her work.

"You look stunning; take a look," she said, pointing to the mirror.

The transformation was astounding; from a plain, smooth-faced man he had become a heavily made-up middle-aged whore. Her brunette fringe framed her dark exotic eyes and her bangs caressed her rouged cheeks and highlighted her luscious red mouth. Malcolm now started to think of himself as Michele the whore; not as Malcolm, the boring manager of a small department in a small business. 'From now on, for the rest of tonight, I AM Michele!' she convinced herself.

"Ok let's get you dressed then," Angie said.

"You can have a quick drink and get into your pantyhose and knickers you hussy," she laughed, playfully kissing his cheek.

"I'll step out and freshen our drinks while you do that I think; I don't want to see your wiggly bits," she laughed, "put the pantyhose on first then the panties over them ok? You've seen one of your girlfriends put on pantyhose I take it? You don't need my advice," she joked; then added as she walked out the door, "don't ladder the fucking things!"

Michele sat on the edge of Angie's queen size bed and kicked off her men's briefs; they now seemed ugly and inappropriate for a lovely whore like her. She eased the pantyhose from the slim packet and slipped the hosiery over her pretty painted toes and slid the sheer nylon up her feet one foot at a time. She carefully eased the pantyhose up her legs keeping the nylon taught; smoothing out the wrinkles as she went. She stood up and pulled the waistband of the pantyhose up over her crotch and smoothed the nylon gusset around her midriff to just below her bellybutton. She slid the red satin bikini panties up her nyloned legs and pulled them snug around her arse and crotch. Michele felt the beginnings of an erection and nearly panicked; but then the though of her sister finding her aroused soon made it go away.

"Ready sis;" Michele called through the door.

"Oh lovely," Angie joked as she came back into the bedroom with two more gin and tonics.

"Ok let's get a move on, I don't want you to be late for your own party," she said in determined tone.

"Stand up and just do as I say buster," she joked; but in a tone that bore no argument.

Angie took the red lace suspender belt and adjusted it so that it sat tightly around Michele's waist and so that the top of garment covered the waistband of the pantyhose. Next she knelt down and drew the diaphanous black nylon stockings up Michele's legs one at a time; the stockings sighed their nylon on nylon whisper as they glided over her pantyhosed legs. Angie carefully adjusted the back-seams so they lay straight and centred along the back of Michele's legs and then clipped the garters hanging from the suspender-belt to the reinforced stocking tops. As Angie smoothed the nylons along her legs Michele suppressed the shiver of excitement and felt a little uneasy about experiencing such emotions; especially with her sister's face so close to her sex organs. Michele swallowed and tried not to think too much into it.

Next Angie hooked the brassiere around Michele's chest and settled the cups into the right position; she walked over to a drawer and took out several pairs of old pantyhose which she stuffed into the cups of the bra to fill them. Then she had Michele step into the black leather mini which she pulled at and played with until it was adjusted nicely at the waist and the hem was nice and straight at mid thigh; she left it unzipped for now. Angie handed Michele the leopard-skin nylon blouse to put on while she went to the dresser and took a drink. She gave Michele a sip of her own drink and put the glass down on the table. Michele noticed that she had not left any lipstick on the rim of the glass as she often did when she was dressed at home. 'That two-coat lipstick really works,' she thought pretending to struggle with the buttons because they were on the opposite side to men's shirts. Angie came over and finished buttoning the blouse and tucked it into Michele's skirt and zipped it up. She buckled the slim gold belt around Michele's waist and adjusted it so that it sat nicely.

"Nearly there; just jewellery and shoes to go" she sighed.

Angie opened the packet which contained the cheap costume jewellery that she had bought for her brother last week. She clipped silver mounted ruby drops to Michele's ears and hung a matching silver and ruby necklace around her neck and matching bracelets on both of her wrists. She put on four large silver rings, two on the fingers of each hand; the rings were set with emeralds and rubies.

Angie sat Michele back on the bed and slid her feet into the black leather high-heeled sandals; buckling the thin straps which came to just above Michele's ankles.

"Now for fuck sake be careful when you walk in these Malcolm," Angie said; " lean a little forward and make sure you come down on the balls of your feet first, not the heels, when you walk. It will take some practice but it's only for one night. You should know what we girls have to put with when we wear those fucking death traps anyway," she chided playfully.

Finally Angie fastened a silver anklet below Michele's left ankle; another fake ruby glittered as it hung from the thin silver chain fastened to the anklet.

"You're done honey; take a look in the mirror," Angie said and helped Michele to her feet. Michele stood up and walked over to the mirror and looked at herself.

She looked stunning; the best she had ever looked dressed as a woman. She had just the look she wanted; in her mind she decided the look was to be called 'London streetwalker' because she looked just like the English prostitutes she saw in the TV shows. Michele walked over to her sister and kissed her on the cheek and said,

"Thanks Angie; you are a doll. Oh! One more thing; pin this on for me will you?"

She handed Angie a large white name bar embossed with the firm's logo in one corner and a Christmas tree in the other; in gold pen script in the centre of the name bar was written: MICHELE NYLONS. Angie pinned the badge to Michele's left breast.

"Michele Nylons; cute name," Angie said.

"Ok Malcolm; err I mean Michele; lets do the last finishing touch."

Angie went to her dresser and took a small green bottle of the cologne 'Poison' and sprayed a liberal amount of the perfume on Michele's neck and décolletage; then she reached down and playfully sprayed under Michele's skirt and on her thighs.

"Just in case you get lucky honey," Angie teased.

Michele blushed a deep red,

"Fuck off Angie!" Michele responded a little hurt.

"Don't be such a girl Malcolm; here take this," she said dropping the small bottle of 'Poison' into the small gold clutch purse that they had purchased last Friday and holding it out.

"The purse has got powder, eyeshadow, mascara, eyeliner, blush, and lippy in there sweety; so you can touch up your makeup as you need to. There's also a hairbrush; everything an old whore needs to ply her trade," she laughed.

Michele stepped forward and took the purse from her sister and bent to kiss her chastely on the lips to bid farewell. Angie shocked Michele by pulling her into a tight embrace and kissing her, closed mouth but forcefully, on the lips; then Angie astonished Michele completely by sliding her hand under Michele's skirt and gently stroking her manhood through her panties. Angie whispered into Michele's ear,

"I know about you, you know!"

Michele pushed her sister away and looking absolutely stunned; she gasped,

"What do you mean; you know!"

"Oh Malcolm; I mean Michele. I've suspected since we were kids. All the times I found my nylons and panties dishevelled and stained; who else could it have been? One day I even saw you putting a pair of my pantyhose in your pocket as you left the bathroom." Angie explained in a soothing voice.

"And last week you knew your ladies shoe size; you insisting on wearing a suspender belt; you had those pictures of Transvestites; and you pretended not know that blouses button on the opposite side to shirt. You sat uncomplaining while I put on your makeup; but the real give away was the way you walk in those high heels honey. It took me fucking months to master high heels when I was a teenager; and you glide around my bedroom like you were born wearing the fucking things!" Angie finished.

"It's nothing to be ashamed of; your secret is safe with me. And you look positively gorgeous; if you weren't my brother I'd fuck your brains out; now get the fuck out here and go and enjoy yourself before I throw you on my bed and ravage you." Angie pushed Michele towards the bedroom door.

Michele was stunned but accepted what she had just heard and realised that she had been stupid to think that she could get away with using her sister to help her crossdress and still keep her secret. In hindsight Michele knew that she would slip up some how. Then a question lanced into her head; 'What did Angie mean about ravaging her? And what the fuck was that passionate kiss and quick fondle all about?'

"Angie; are you a lesbian or something?" Michele asked her sister as they walked to the front door.

"I'm an 'or something' ok; but that's a conversation for another day; now get the fuck out of my house and party til you drop bitch! Oh; and come around for coffee tomorrow afternoon and tell me all about it!" she laughed and pushed Michele out of the door and into the night air.

Michele walked over to her car, stunned at what had just happened; even though she had lost count of the number of gin and tonics she had drunk over the last few hours she now felt completely sober. She dropped in behind the wheel and her skirt rode up revealing her stocking tops; she smoothed down her skirt and slid her hands along her stockinged thighs and sighed with desire at the feel of her feminine attire.

Michele smiled to herself and drove off into the night trying to get her head around the last few minutes. Eventually she settled down enough to realise that she had been particularly stupid drinking so much alcohol with a three quarter of an hour drive ahead of her from the suburbs to the city; the police were ruthless when it came to alcohol breath testing during the festive season. She decided to use a little used back road that bypassed most of highway into town; it would put an extra twenty minutes or so onto her journey but she was better safe than sorry.

After she had driven a few kilometres down the dark road she realised that the effects of the drinks she had imbibed earlier had far from worn off; she had to really concentrate and to make matters worse she had never considered the difficulties of driving a car whilst wearing high heels. Michele checked her mirrors and then reached down and attempted to unbuckle her right shoe so that she could better control the brake and accelerator. It was a huge mistake; as she struggled with the buckle on her high heel her car swerved violently to the right and she had to correct the vehicle quite quickly on the dark narrow road. As she gained control of the car and was congratulating herself for avoiding disaster she saw blue and red flashing lights in her rear vision mirror.

"Fuck!" she exclaimed, and pulled her car over into a darkened rest area at the side of the road.

She followed the small dirt track to series of marked parking bays behind a darkened toilet block and pulled into one of the spaces; she looked around and saw that the rest area was deserted except for her own car and the police cruiser that had now pulled up beside her. A fat policeman squeezed from behind the wheel of the police car, turned on a large black torch and sauntered over to her driver's side window; Michele wound down the window terrified. She didn't know wether to be more worried about being out dressed up in drag or being over the prescribed alcohol limit. The fat policeman shined his torch on her face, smiled and said,

"You were all over the road back there miss; have you been drinking?"

Michele summoned up all of her courage and answered,

"I had a couple of drinks an hour ago officer but I'm sure I'm under the limit; I swerved to avoid a small animal on the road," she lied.

The policeman looked at her for a nearly a full minute shining his torch inside the car and up and down her body and back to her face.

"Jesus Christ you're a fucking guy aren't you?" he asked incredulously.

"Yes officer; let me explain......." and Michele went on to explain that she was dressed in drag to attend a theme party at work.

After listening to her story for a few minute the officer cut her short.

"Well that may be sir, ma'am; whatever. But I still think that you are under the influence of alcohol and I intend to issue you with a roadside breath test." He said and waddled back to the cruiser and returned with an alcometer.

He pushed it through the window in front of Michele's face and said,

"Put your lips on the tube and blow; words I'm sure you quite used to;" he added cruelly.

Michele did as she was told and heard the machine beep rapidly after a few seconds. She hung her head and contemplated what would happen next. She would be taken to the police station and have to suffer the indignity of waiting around for bail dressed up in drag. Undoubtedly the policemen at the station would ridicule and taunt her. Even worse; what if they put her in a holding cell? She had read about what happened to some young men in prison at the hands of jailhouse thugs; what chance would she have dressed as she was? Could she ask for protective custody? Her head was spinning.

The Policeman took the machine away from Michele's lips and looked at the reading and smirked.

"You're shit out of luck tonight sweety," the cop smiled evilly at Michele through the window.

He turned on his heels and wobbled back to his cruiser; 'He's calling it in or whatever they do!' Michele thought to herself. She was on the verge of sobbing. She looked across at the police cruiser and by the light of the dome light she saw the fat cop leaning inside talking on the radio. Then the flashing lights on the top of the police car went out, closely followed by the head and tail lights. The cop slammed the door and the rest area became hauntingly dark and deathly silent. Michele could just make out the dimmed glow of the policeman's torch as he returned to her car; as he approached she saw he was shading the light with his other hand. He leaned on the roof of her car and it lurched under his added weight.

"Look honey, I've dealt with your type before ok; you don't do thirty years on the force without dealing with the occasional trannie now and then. You are in all sorts of problems here; the reading on my little machine there says you're at least twice the legal limit to be driving."

"Now, we can sort this out one of two ways; you can accompany me to the police station, and I'm sure the ramifications of that option have crossed your pretty little mind; and also you will lose your license and cop a hefty fine. Plus I'm betting someone who drives a car like this has a job where a DUI will not be particularly welcomed," the fat cop droned on.

"Or I can get in the passenger seat there and we can settle this quickly, painlessly; and to both our advantages if you know what I mean?" he finished.

Michele was now totally confused; was there a way out of this? Was he asking her for a bribe? Thank god! There was a way out of this! All she had to do was let the cop get in passenger seat and she would hand him some cash and he would be gone. Yes; it made sense! He wanted to sit in the car so no one passing by could see her handing him the money; that's why he turned off his flashers and headlights.