Shemale
2006-08-29
Whores and Pimps - Part II
By
Michele Nylons
Michele sat silently in the car as she watched the tail lights 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.
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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 party goers.
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’.
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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 hair styles, 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.
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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.
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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.
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Jill shuddered and Michele felt Jill’s panties moisten. Jill slid her hand down and stoked 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 on 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.
Michele pushed forward and felt her engorged member slide deep into Jill’s slick hot cunt; Jill wrapped her legs around Michele’s and Michele felt the rough material of Jill’s trousers rub against her silky nyloned legs and she shuddered and started to slowly fuck Jill with long hard strokes. To any observer they looked like a couple necking in the shadows; their mated sex organs hidden by Michele’s skirt.
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Jill whimpered,
“Fuck me bitch! Fuck me whore! Fuck me Michele!”
Jill ground her pubic mound against Michele as she thrust forward and Michele was delighted by the added sensation of Jill’s mound grinding against her balls still trapped in her satin panties and nylon hose; Jill’s vaginal muscles spasmed against Michele’s rock hard penis as Michele slowly fucked her. Jill groaned,
“Coming! Coming! Coming!”
Michele thrust forward and pushed hard against Jill and emptied her seed deep inside her. Michele’s knees shook and her knees nearly buckled as she shuddered on her high heels. Jill was whimpering and moaning; Michele covered Jill’s mouth with hers and their tongue’s intertwined and danced as Michele’s hot seed shot deep inside Jill’s cunt. They both clung to each other and shook in ecstasy as they orgasmed.
Gradually their orgasms subsided and they held each other for a long time; Jill sitting on the balcony ledge, her legs wide, with Michele between them, kissing each other gently and stroking each other’s hair. As the last of Michele’s seed seeped from her deflating penis she eased her crotch away from Jill’s and eased her flaccid member back inside her torn pantyhose, pulled her panty crotch back in place and smoothed down her skirt. Jill eased her sodden panty over her mound and zipped her flies. They continued to kiss and murmured endearments into each others ears.
“Oh my! I’ve never done anything like that before,” Jill whispered; laughing in Michele’s ear.
“Me neither,” Michele whispered back; nuzzling Jill’s earlobe.
“Will you still respect me in the morning?” Jill joked.
“Never mind about the morning; what about later tonight? Can we leave the party together?” Michele asked.
Jill looked up into Michele’s pretty face and frowned,
“I’m sorry honey; I came with Steve and Jenny from accounts; I’ll bet there are enough people here who saw us come out on the balcony and will be wondering what we got up to. I’d better leave with Steve and Jenny and you can call me tomorrow ok?”
“You do want to call me don’t you?” she added; looking lovingly into Michele’s eyes.
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“You know I will,” Michele answered.
“You’re right though; best we don’t let the office gossips wag their tongues any more than they need to. What we just had was wonderful and I want to see you tomorrow so that we can talk about where we go from here Jill, ok?”
“You bet we will talk tomorrow; and if you’re a good girl, or should I say boy, maybe we can do more than talk,” Jill winked at Michele as she eased herself off the balcony ledge and on to her feet.
“Now; maybe I better go inside first. I really need to go the bathroom and dry myself,” Jill blushed as she looked at Michele.
Michele kissed Jill quickly one last time,
“I’ll call you tomorrow ok? I can take you to lunch. ”
“Or maybe we can stay at home and eat there,” Jill laughed playfully and winked at Michele and then moved away, back through the balcony doors to rejoin the party.
Michele was astounded but exceptionally happy with what had just happened. She was surprised that Jill could be so brazen and even more surprised that quiet, demure Jill had such passion. Michele had completely forgotten about the horrible events earlier at the roadside rest stop as she adjusted her skirt and walked back into the party. The party was now in full swing with revellers on the dance floor and other couples sitting in corners smooching and canoodling. ‘It’s amazing what booze, dim lighting and Christmas cheer can do to loosen people’s inhibitions,’ she thought. Michele made a beeline for the toilets; she needed to go and she also guessed that her makeup needed touching up. ‘Just because it’s whores and pimps night, doesn’t mean that this whore needs to get around with messy makeup. ’ she laughed to herself.
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Michele found her way to the men’s room; even though everyone was dressed as the opposite sex propriety demanded that they use their own toilets. She went into a stall, lifted her skirt and used toilet paper to wipe her genitals. She noticed that the front panel of her satin panties was stained with her and Jill’s secretions. Michele thought that these panties would not be being washed for a while and blushed at her own brazenness. She adjusted her stockings; pulling the garter straps snug against her thighs and felt down her legs to feel that her seams were straight. She peed and adjusted her panties and skirt and stepped out on the stall and over to a sink with a spotted mirror over it.
Michele mooched around in her purse and found foundation, powder and lipstick. Kissing and caressing Jill during their lovemaking had removed some of her foundation and lipstick. She applied a little foundation on her cheeks and chin and then set the makeup with her gloss finishing powder. She carefully applied another layer of plum red base coat over the existing faded lipstick and waited a minute for it to dry before applying the glossy topcoat. She brushed her hair, and pleased once more with her appearance, she exited the toilet.
Michele pushed through the crowd to the bar, sat on a stool and ordered a gin and tonic. Michele was looking down playing with the hem of her leather miniskirt when she felt a presence beside her. She turned to one side and saw a lovely woman standing beside her leaning on the bar trying to get the barman’s attention. The woman was obviously a man in drag but exquisitely dressed and made up; she probably looked as good as Michele or maybe even better.
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The woman had a short black bob framing her pretty face; her eyes were dark with black eyeliner, thick mascara, and dark grey eyeshadow fading to a steel blue. Her cheeks were rouged and her lips a glossy bright red; diamante earrings dangled from both ears and matched the choker around her slim neck. Her fingernails were painted bright red to match her lipstick. She wore a black chiffon cocktail dress that barely came to her thighs; a jewelled suspender clip peeked out from under the hem of her dress and glistened in the dim light where it was fastened to a sheer taupe stocking; the stocking top a dark chocolate brown. The woman’s slim, glossy, stockinged legs ran down to black high heel pumps. She was delicious.
The barman delivered Michele’s gin and tonic and placed a drink before the other woman. The woman turned to Michele, raised her glass and said,
“Bottom’s up Michele,” and took a sip of drink, leaving a bright red lipstick impression on her glass.
Michele responded, “Bottom’s up, err; Ellie,” as she spied the name on the woman’s name bar, pinned to Ellie’s left breast.
Michele looked down and rummaged in her purse for a cigarette; more to allow her time to think of a conversation starter than the need to smoke, and then offered one to the woman beside her. Ellie took one and offered a gold lighter to Michele’s cigarette and then lit her own.
“I knew you would look lovely tonight Michele; you are undoubtedly the most beautiful woman here,” Ellie complimented Michele.
“Well it’s all due to my sister you know; she bought these clothes for me, dressed me and did my makeup. ” Michele said.
“And I don’t know Ellie; if you had been here earlier, you would have given me some stiff competition I think,” Michele smiled back.
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“Oh I don’t think it’s all down to your sister Michele; I just saw you fixing your makeup like a professional in the men’s room; and your previous practice wearing women’s underwear leads me to think that you are somewhat of an expert at dressing up as a woman,” Ellie smiled back.
Michele paled and then stared hard into the face of the woman standing close beside her.
“Eddie; it’s you!” Michele hissed.
“Well honey; I’m Ellie tonight, and shall we just say that it takes one to know one hey?” Ellie went on,
“The panties and stockings under your work suit were a giveaway but all I had to do was study you closer to see the traits of a closet transvestite. A man with shaven hands and fingers and long finger nails; oh and by the way honey, you really need to get right into the quick of your nails with your nail polish remover; sometimes at work you had just a smidge of nail polish left in the corners of your nails; and your effort tonight hun was just too good. No guy masters walking confidently in high heels like you in one night. ” Ellie lectured Michele.
“You see honey, I’m in the closet too,” Ellie finished.
“But why were you so cruel to me then?” Michele asked.
“Well Michele; that’s just my nature, besides I like having fun at other people’s expense; just like I am with you tonight honey. ” Ellie smiled wickedly.
“What do you mean by that?” Michele asked feeling lighter in the head.
“Well I heard you had a little car trouble earlier this evening,” Ellie grinned “Or shall we say a little problem with the law. ”
“But I heard you talked your way out of it. Oh sorry, that’s not how my friend explained it; but he did say that you used oral means to get off a charge of DUI,” if you will pardon the pun.
Michele was shocked; she couldn’t believe what she was hearing; the thinly veiled reference to what happened in the rest area on the way to the party. How could Ellie know about that?
“You smug cunt; bragging to everyone about how your sister was going to dress you and make you up; do you think I fell for that bullshit? I knew you wanted a cover story though, so I searched the personnel records at work and came up with your sister’s address. I just fed the information to a friend of mine who just happens to be a policeman with a penchant for transvestites and gave him your sister’s address. He took it from there and followed you. ” Ellie concluded.
“You fucking sick twisted bitch!” Michele spat; “You fucking perverted whore!” Michele felt her head getting lighter still, she was becoming drowsy and she dropped her cigarette.
“Oh I’m all that Michele; and I haven’t finished with you yet by a long score. As soon as the drug I dropped into your drink takes effect you are going to pass out; I’d say in about thirty seconds. Then I’m going to be mister nice guy or should I say miss nice girl and help a friend who had had too much to drink up to her room here in the hotel. ’
“You’ll like it up there; your old friend the cop is waiting for us, and I invited a few of my other friends along too. We’re going to have own little party tonight honey,” Ellie’s voice started to fade in and out.
Michele tried to get to her feet and as she did she blacked out.
When Michele groggily opened her eyes about an hour later she slowly realised what had happened as her memory returned. She couldn’t move her hands and feet and realised they were tied to a bed. She looked over to one side and saw Ellie on her knees bent over the fat cop who was naked and sitting on a chair.
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Ellie was fellating the cop who looked over at the bed and saw Michele was awake. He tapped Ellie on the shoulder and she spat out the cop’s cock and looked over at Michele.
“Well hello honey; glad you’re awake. Now that you are with us, the party can finally really get going,” Ellie sneered sarcastically.
Michele looked around the hotel room trying to focus; she could make out a few shapes and realised that there were more people in the room. She also realised that she was in real trouble.
To be.
