Whores and Pimps - Cover

Whores and Pimps

Copyright© 2009 by Michele Nylons

Chapter 2

Erotica Sex Story: Chapter 2 - Malcolm is the closet transvestite Michele who is yearning to come out of the closet and play. He organises the firm's fancy dress Xmas party using the theme "Whores & Pimps". The difference is that the men come as whores and the women as pimps. Michele gets blackmailed, seduced, raped and gang-banged as the night progresses. Then she goes home to tell her sister all about it only to find her sister has a penchant for trannys.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Ma/Ma   Consensual   NonConsensual   Reluctant   Rape   Coercion   Blackmail   Drunk/Drugged   BiSexual   Heterosexual   TransGender   CrossDressing   Incest   Brother   Sister   BDSM   DomSub   MaleDom   Spanking   Rough   Humiliation   Sadistic   Gang Bang   Group Sex   Oral Sex   Anal Sex   Masturbation   Petting   Sex Toys   Water Sports   Exhibitionism   Voyeurism   BBW   Foot Fetish   Leg Fetish   Prostitution  

Michele sat silently in the car as she watched the taillights of the police car disappear in the distance; the bitter aftertaste of the policeman's sperm still in her mouth. She was confused; the fat cop with his stubby fat cock had forced her to fellate him; but she had become sexually aroused and hadn't even realised it. She sat for a few minutes and decided that the outcome was still better than being locked in a jail cell overnight. She would just make sure she never told anyone about what had happened to her tonight.

Michele reached down and undid the buckle on her right shoe and slid the high heel off her foot. Then, as she was bent over in her seat, nausea overcame her and she only just managed to open the car door before she wretched and threw up onto the pavement of the parking bay. She wretched until her stomach was empty, disgorging the many drinks she had drunk in the afternoon and early evening. Michele actually felt better now; clearheaded and sober. She took some wipes out of the glove compartment and wiped her mouth clean. She found a half bottle of spring water in the drink holder in the dash and rinsed her mouth out.

She must be thinking straight she thought because the first thing she did was to check her lipstick in the rear vision mirror. Angie was right about the two coat lipstick; Michele only needed a apply a minor touch-up to the plum red base coat then go over it with the clear top coat and her makeup was perfect again.

Michele resolutely started the engine and pulled back onto the road determined that she could put this horrible incident behind her and still enjoy her one night out dressed as a woman.

Michele couldn't help re-living what had happened to her as she drove the last twenty minutes to the hotel, but as she got closer to her destination she began to think more about the party than she did about the cop. She parked in the car park underneath the hotel, receiving an admiring glance from the attendant in his booth. She parked, buckled on her right high heel, took a deep breath and got out of the car. She walked the length of the well-lit car park and entered the elevator. She pushed the button for the second floor where the function room was located and then she saw herself in the mirrored wall of the elevator car.

Michele was impressed with what she saw. She saw a middle aged whore; attractive and desirable dressed in her black leather miniskirt and leopard-skin print nylon blouse. Michele adjusted her skirt where it had rode up in the car so that the hem was mid-thigh, nicely displaying her black stockinged legs which drew her eyes down to her black high-heeled sandals; her red painted toenails just visible through the diaphanous nylon. Her pretty painted face was framed by the brunette wig; the lighter tints in her hair highlighted by the fluorescent light of the elevator car. She adjusted the wig and took the brush out of her purse and combed it out around her neck and shoulders; she combed the fringe and made a final adjustment so that it sat straight and just covered her eyebrows. Michele quickly turned around looked over shoulders to check the seams of her stockings were straight; and then she was ready. The door opened to reveal the hotel function room crowded with rowdy partygoers.

They all turned and stared as Michele entered the foyer; they looked puzzled; then Michele summoned up her courage and said,

"Come on everyone; don't you recognise me?"

Peals of laughter and applause lit up the room, and almost as one they cheered,

"Oh my god; it's Malcolm, you look fantastic!"

Michele moved into the room and mingled with the crowd; most of her colleagues were well on their way to being drunk, after all she was nearly an hour late and her work colleagues were never the ones to not take full advantage of a free bar. Just about everyone complimented Michele on her appearance and asked her how she looked so convincing. Michele's response was the same to everyone who asked the question,

"My sister chose the clothes and made me up; remember I told you guys that she was going to do my costume and makeup."

Michele's ruse was working; she was quite settled in now and felt comfortable dressed as a whore now that she had a drink in her hands and was amongst friends. Most of the business's employees were present and they had all made some effort to dress up in keeping with the theme of the party. The men were mostly dressed in drag; most in tacky rental costumes with hairy legs sticking out of from under cheap skirts and dresses and outrageous makeup looking like the actors from the movie 'Pricilla; Queen of the Desert'. Some had made more of an effort; probably dressed by wives or girlfriends, and could almost pass as women in the darken room which was lit only by multicoloured party lights.

The women fared better; they ranged from seventies style pimps dressed in flared jeans, flowery shirts, Afro hairstyles, platform shoes and over- large hats. Other women wore over-large pinstripe suits and dressed as thirties gangsters from the speakeasy era. Everyone was having fun and complimented Michele on her choice of the theme for the fancy dress party. Michele relaxed even more and after a few more drinks was partying along with the rest.

Several of the partygoers played little jokes on her; saying she looked sexy enough to fuck dressed as a woman; a couple of playful types stuck their hands up her skirt jokingly. Michele was so happy; the compliments made her feel cheerful but more importantly she loved being in the crowd dressed as a woman. She was slightly turned on by the feel of the lingerie on her body and the sleek sensation of her nylon stockings on her legs. She skittered from here to there joining groups for a quick chat and then moving on to another.

It came as no surprise when the Managing Director announced that Michele had been judged the best-dressed man at the party. The best-dressed woman award went to Jill; a quiet, attractive lady in her forties who worked in the accounts department; she like Malcolm, kept mostly to herself. As tradition dictated; the music was cranked up, the lights dimmed further and they were expected to dance together. Jill had dressed as a prohibition era gangster come pimp, and wore a dark pinstriped suit including a fedora hat and false moustache. Jill was wearing a name-bar that said Johnny Nightwalker; her little play on words to suit the occasion.

Michele and Jill danced awkwardly together to a rock and roll number but soon the dance floor was full of drunken revellers. Michele and Jill shouted compliments to each other over the loud music; each complimenting the other about how convincing they looked dressed as the opposite sex.

The music changed and a slow dance number was played and couples took each other in their arms and danced close together, swaying to the music. Jill took Michele in her arms, pulled her close and began to lead a slow dance. Michele felt really weird now; here she was dressed as a whore dancing with a woman from accounting, on whom she had had a slight crush, and who was dressed as a man.

Jill held Michele close against her body and Michele could feel Jill's breasts through the layers of her suit and her own nylon blouse. Jill's arms held her in a tight embrace around her waist and shoulder. Michele was vary aware of her own clothing; the flick of the hem of her miniskirt on her stockinged thighs, the rustle of her silken blouse on her bare skin and the taste and smell of her makeup and perfume. Michele was becoming aroused. She could feel her cock hardening in the confines of her pantyhose and panties; it bulged at the front of her skirt and she knew that Jill must be able to feel it.

Jill touched Michele's hair and eased Michele's head onto her shoulder; she whispered,

"You're getting hot there Malcolm; you naughty boy," and giggled.

"I'm Michele tonight honey," Michele answered, getting into the role.

Michele was aware that Jill was more than a little drunk; Jill was a little unsteady on her feet and the alcohol was also allowing her to come out of her shell.

"Well I've got a little secret myself Michele;" Jill went on, "I'm more than a little hot myself."

"What do you say we sneak out onto the balcony and get some fresh air?"

Jill broke their embrace and took Michele's hand and led her out onto the full-length balcony overlooking the front of the hotel. There were a few couples out there smoking and drinking and one couple was necking; it looked quite strange to see a man standing in high heels and a skirt kissing his wife who was dressed in jeans, platform shoes and outrageous seventies male kitsch. Jill led Michele into a dark corner and turned to face her. Even though Jill was dressed as a man she still wore makeup and looked very attractive for a woman of her age, except for the stupid fake moustache. Michele reached up and with her painted fingernails removed the fake object from Jill's upper lip.

"I've always liked you, you know Malcolm; and you know what? You look dead sexy dressed as a whore," Jill giggled nervously looking directly into Michele's dark makeup painted eyes.

"I told you; I'm Michele tonight Jill; and I have had a thing for you for ages too but I've been too scared to approach you," Michele responded.

Jill reached out and took Michele in her arms and pulled her close,

"I feel so masculine dressed like this; I feel that I can say what I like and do what I want."

"I know," Michele answered, "I feel so feminine; it's the costumes we are wearing."

"Bullshit! We're both turned on by each other; why fight it," Jill said and reached out and kissed Michele on her lips.

Michele responded and slid her tongue into Jill's mouth and crushed Jill's lips with her own. They both groaned and held each other tight. Michele felt her erection return and push against her panties; Jill felt the hard member rub against her through Michele's skirt and her suit pants. She reached down with a hand and stroked the hard member through Michele's skirt. Hiding where they were in the shadows no one could see what they were doing and Michele reached down and undid the fly on Jill's baggy trousers and slid her hand inside and smoothed her painted fingernail along the front of Jill's slick nylon panties and down under her crotch. Jill may have been wearing a man's suit but her underwear was all femininity.

Michele rubbed a finger along the crotch of Jill's panties and pushed the silken gusset into her labia, pressing her knuckle against Jill's clitoris. Jill shuddered and Michele felt Jill's panties moisten. Jill slid her hand down and stroked Michele's diaphanous nyloned thigh and slowly ran her fingers up to Michele's stocking-top, continuing further up along her pantyhosed thigh until she cupped Michele's hard member encased in the silky-smooth layers of her pantyhose gusset and satin bikini panties. Jill grasped Michele's gossamer encased prick and started to stroke it. Michele panted into Jill's mouth; now opened in excitement,

"Oh yes honey; oh that's lovely!"

Michele eased her fingers around the crotch of Jill's panties and inserted a finger into Jill's wet cunt and thrummed her clitty with her thumb. Jill ground against Michele and they pushed against each other; Michele finger fucking Jill and Jill frantically wanking Michele. Their mouths smashed together again; their lipstick smearing as they inhaled each other's sweet breath. Jill moaned,

"Fuck me Michele. Fuck me here in the dark. Do me right here on the balcony!"

Jill scraped a nail against the taught nylon wrapped around Michele's cock and tore a hole in the flimsy nylon pantyhose. She eased Michele's penis through the hole and pushed her panties to one side freeing Michele's throbbing cock. Michele lifted Jill up on to the low sandstone balcony ledge so that Jill was seated; her legs apart. Michele pulled down on Jill's baggy trousers so that her opened flies granted Michele full access to Jill's sex. Jill guided Michele's hard cock between her legs and Michele's skirt rode up as her cock nestled into the smooth wetness of Jill's labia.

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