Whores and Pimps - Cover

Whores and Pimps

Copyright© 2009 by Michele Nylons

Chapter 4

Erotica Sex Story: Chapter 4 - 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 lay on the bed sated; splashes of semen glistened on her stockings, blouse, face and hair. Steve, Joe and Bill stood around the bed looking at her, their erections slowly subsiding. She looked across the room and saw that Ellie had returned to administering to the fat cop's needs. She was on her knees and her pretty face bobbed up and down in the fat cop's lap.

The fat cop was sprawled in the chair; his piggy eyes locked on Michele.

"That was some performance there Michele; for a girl who only sucked her first cock a few hours, ago you sure learn fast," he said.

Ellie took her face out of the cop's lap and turned her head towards Michele.

"See, I told you that you would probably end up liking it didn't I," she gloated.

The fat cop pushed her face back down on his stubby cock."

"Shut the fuck up and suck my cock bitch," he laughed, "You let those other boys worry about her; you just take care of me."

The fat cop screwed up his eyes and reached down with both hands to push Ellie's face onto his penis. He bucked in his seat and face-fucked Ellie with short hard strokes. Ellie was working hard at sucking his member and Michele could distinctly hear the sucking and slobbering noises Ellie made as worked on the cop's cock. Ellie was rocking on her knees, the toes of her black high-heels dug into the cheap carpet, her short black dress had ridden up at the back revealing her white satin panties and matching suspenders clipped to the gauzy taupe stockings encasing her long sleek legs. She looked very sexy. Slutty, but definitely sexy.

Michele felt her penis begin to harden in her sticky panties. She couldn't believe she could become aroused again so soon after her last orgasm! The sight of Ellie fellating the fat cop was also having its effect on Steve, Joe and Bill; Michele noticed that they were also in various states of arousal.

Joe sauntered over to where Ellie was fellating the cop.

"Mind if I use the other end?" he sniggered at the fat cop.

"Do what you like with her Joe; just so long as she doesn't lose her rhythm," he laughed back.

Ellie didn't even flinch; she just carried on sucking away on the cop's stubby cock. Joe grabbed Ellie's high-heels and spread them apart, her stockings rasping on the cheap dirty carpet. Joe positioned himself between Ellie's sleek nyloned legs and took hold of his cock and began to rub it in the cleavage of Ellie's satin pantied buttocks.

Michele felt her own cock harden and then she became aware that Steve had slid his member into her loose fingers; without conscious thought she gripped the thickening member and began to stroke it. She was mesmerised by what was happening across the room. Bill shifted to the other side of Michele and put her hand on his cock. Michele lay there masturbating the two men while the three of them watched Ellie suck the fat cop while Joe rubbed his cock on her panty clad arse.

Joe reached down and slid the silken gusset of Ellie's panties to one side and exposed her puckered sphincter. He wet his finger with his tongue and probed at the wrinkled crack. Ellie kept fellating the cop but she also pushed back with her body and Michele watched fascinated as Joe's finger disappeared inside Ellie's anus.

"God that looks good," Michele whispered.

Bill heard Michele and took that as his cue. He moved down the bed and slipped his hand under Michele and gently eased her over on her side. She could still see Ellie and the two men across the room and she was still wanking Steve's hard shaft. Michele didn't take her eyes off the trio across the room even as she felt Bill slide his hand under her nylon panties and insert a finger inside her semen lubricated passage. She gripped Steve's cock harder and wanked away at it.

Joe removed his finger from Ellie and spat into his palm then rubbed the spit on his member. He positioned himself directly behind Ellie and nestled the glans of his penis against her sphincter. He reached down and gripped each of Ellie's silken stockinged thighs in each hand and began to push. He groaned as Ellie pushed back against him until his belly was hard against her bottom and he was buried in her to the hilt. Ellie wriggled her skewered arse and began to suck harder at the fat cop's stubby member.

Bill rucked Michele's black leather mini up around her waist and moved down the bed and knelt beside Michele' pantied rump. He pulled her panties down, the nylon material of her panties whistling on her hosed legs, and left them around one slim ankle. He pushed Michele over further and lifted her leg so that she was lying on her side with her legs scissored open. Bill lay down behind Michele and put his rock hard cock at the entrance to her back passage. He pushed and Michele groaned at the pain as Bill's glans forced open her tight sphincter.

"Easy honey," Bill whispered into Michele's ear and the nuzzled her neck, "just relax and it will slide right in; Steve's already lubed you for me."

And it did! Michele relaxed and then felt Bob's hard cock slide right up inside her. She was still fascinated by the other trio having sex across the room but she was now very aware of Bill's body rubbing against hers and his grunts and groans as he fucked her. She loved the feeling of her anus being filled and the shivered with pleasure as Bill's cock rubbed against her prostate.

Steve had now moved to the edge of the bed and was watching the sex going on around him as he slowly stroked his own cock.

Joe was pounding himself in and out of Ellie; he had moved his hands down to her feet where he gripped her high-heels and rode her like a sleigh. Ellie was a lovely sight to behold with her black chiffon dross rucked up around her waist, her gossamer taupe stockings clipped to her white satin suspenders and her matching satin panties, the gusset eased aside to allow Joe access to her arse. Her pretty face was buried in the fat cop's lap, sucking his engorged manhood and she bucked back and forth on her knees keeping rhythm with Joe's pace as he fucked her. Joe was groaning and moaning and the fat cop had his eyes screwed shut and pushed Ellie's face down into his lap. They groaned in unison.

"I'm coming; oh god I'm coming!"

Michele felt Bob quicken his pace as he hung on to her and pounded his cock in and out of her come slicked anal passage. Michele pushed back against him and wriggled her bottom. Lying on her side like this she was unable to thrust back and forth but her wriggling and pushing caused the glans of Bob's penis to massage her prostate gland bringing her closer to orgasm. Bob suddenly wrapped his arms around Michele and pulled her back hard against him and Michele felt his cock begin to shudder as streams of hot semen flooded her anal passage. Bob's manhood spasming against her anal gland caused Michele to climax too and she wriggled her bottom and pushed back against Bob as she shed her spend into her already come-sodden panties.

Steve spun around on the bed and aimed his cock at Michele's heavily made up face. He groaned and shot stream after stream of hot semen over her face, rivulets of his juice ran down over her eyes, nose and on to her lips. Michele gobbled the salty offering, slavering the fluids with her tongue and licking it into her mouth as her own orgasm shot through her anus, testes and penis. She was experiencing one of the most intense orgasms of her life.

The fat cop pushed Ellie's head down into his crotch and held her there as he came, he bucked and squirmed in his seat as his emission erupted out of his throbbing cock and deep down Ellie's throat. Ellie wriggled and struggled tried to pull herself free to prevent herself from drowning on the fat cop's semen. Joe used Ellie's struggles for his own gratification and plunged his turgid penis deep into her pulsing anal channel and expended his load, flooding her with a deluge of hot semen. Ellie was nearly asphyxiated when her own orgasm ripped through her and she flooded her panties, a wet stain spreading across the front panel of the white satin garment.

Everyone in the room had climaxed almost simultaneously and they all fell apart and gasped for breath as they came down from their respective orgasmic highs. Ellie was sprawled on the floor heaving in deep breaths. Between her gasping breaths she guzzled the remainder of the fat cop's spunk. She pushed herself up on her knees and reached up and slapped the cop playfully across the face.

"You bastard," she wheezed, "I know we have played at erotic asphyxiation before; but not when I've had a big cock inside me at the same time!"

"Fuck it was incredible though," Ellie smiled and turned around and kissed Joe passionately on the lips.

She looked across at Michele,

"Well was I right or was I right?"

"I told you most of the girls eventually like what they experience here; and I just knew you would be too much of a slut not like it too."

"When our friend in blue here," Ellie nodded at the fat cop, "told us that you had continued on to the party after he made you suck his cock in that parking lot; we knew you would eventually become a willing participant in our little orgy."

Michele was still catching her breath and doing her best to wipe Steve's coagulating semen off her face.

"Well I'll tell you what Ellie; you're a arsehole at work and you're a cunt of a friend outside of work. But if you ever plan another orgy like this; you better count me in" Michele replied, a smirk breaking out on her face.

Everyone in the room burst into laughter.

As Michele drove back to her sister's house in the early hours of the morning she pondered on the previous evening's events. Michele's sister Angie had revealed that she knew her brother Malcolm (Michele's alter ego) was a closet transvestite (and seriously hinted that she herself was a lesbian!). Michele's workmate Jill had let Malcolm make love to her whilst he was dressed as Michele; and Eddie had turned out to Ellie, the most perverted transvestite you could imagine!

Michele had fucked and sucked and been fucked and sucked and had totally fallen in love with the secret underworld of transvestite sex. Ellie had said she would arrange another transvestite and admirer party for the following weekend and Michele was already planning what to wear. What a marvellous twenty-four hours it had been!

When Michele arrived at her sister's house it was dark and totally silent. She let herself in and staggered to the spare bedroom, shucked off her semen encrusted clothing and wig and fell into bed without even bothering to clean off her makeup. She fell asleep immediately and didn't wake up until late Saturday afternoon.

Malcolm woke up to find Angie sitting on the end of the bed with a cup of hot steaming coffee in her hand.

"Drink this, shower, shave, brush your teeth, and then come and tell your older sister all about your evening, oh brother of mine!" Angie giggled.

"From the mess your clothing was in you certainly got up to something exciting," she went on.

Malcolm looked groggily around the room.

"Where are the clothes I wore last night," he asked inquisitively.

"Cleaned, pressed and waiting for when Michele re-appears. I even washed, blow dried and brushed your wig," Angie replied.

"In fact after you have cleaned yourself up; why don't I help you transform yourself again. Yesterday was fun and I'm sure you learned a lot," she smiled.

"I don't know? I feel kind of weird letting my sister dress me as woman and do my make up," Malcolm frowned.

"Oh fuck that! I know you liked it; now get up and get yourself sorted and meet me in my bedroom. Once I've transformed you into 'Michele' I'm sure you will feel more comfortable about telling me all about what happened last night. Let's just call it 'girl talk'," she winked, and then got up off the bed and left the room.

Malcolm did as his sister bid and brushed his teeth, showered and shaved. It took a while to remove the caked-on makeup that he had not removed before going to bed but liberal use of moisturiser removed most of it. He was wondering what his sister was getting up to, wanting to help him dress again. The last time she did it, now nearly two days ago, she had put her hand under his skirt and touched him through his panties. What was that about?

Malcolm had been crossdressing for so long now that his mind automatically switched from thinking of himself as Malcolm to Michele as soon as he began to transform himself.

When he came back into the bedroom wearing only a bath towel around his waist he found Angie sitting on the bed surrounded by a selection of feminine clothing, most of which Michele had worn the previous evening. It was now cleaned and pressed. A packet of Kaiser Ultra Sheer stockings replaced the laddered and come-spattered hose he had worn home. Michele's wig and makeup were arranged on the dressing table.

Angie was wearing a pleated navy blue skirt that came to just above her knees. She wore a white satin blouse that exposed her cleavage, navy-blue high-heels and sheer tan hosiery. She was also wearing full makeup and jewellery. She looked quite hot for a woman of her age.

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