So You Want To Be A Nurse By Michele Nylons
Chapter Five – The Gathering
So how did Polly know about the five pounds?
Dr Marron had tipped Michele five pounds but Michele hadn't told her about that.
At the pub Polly had said: "So now you spend some of that five pounds that Dr Marron left you and buy a round."
So how did she know?
Polly lay sleeping beside her in the bed in room 302 at the Chelmsford Ambassador Hotel. They were still dressed in lingerie and stockings; their heavy makeup smeared from a night of heavy lovemaking.
Michele got out of bed and plugged in the little electric jug to boil water for tea. While it boiled she fixed her makeup and brushed out her hair. She was tempted to clean it off and transform back into Michael but she had to admit the more time she spent dressed as Michele the more she liked it.
She bought two cups of tea over the bed and gently shook Polly awake.
Polly was as dishevelled as Michele had been and her makeup was also smeared all over her face but to Michele she still looked beautiful. Michele leaned down and kissed her; she tasted of stale cigarettes, gin and a hint of semen.
"I must look like shit and you, you bitch; you look downright sexy, although those stockings are laddered beyond repair," Polly nodded at Michele's legs.
"Well having your legs continually raked by the high-heels of a bitch in heat will do that!" Michele spanked Polly's arse through the covers.
"Well I didn't hear any complaints at the time and my best sheers are ruined too," Polly laughed.
Michele passed Polly her cuppa and the obligatory cigarette.
Michele suddenly turned serious.
"How did you know about the five pounds that Dr Marron left me?" Michele asked.
Polly's face drained and she went pale.
"I never told you about that, but you knew about it at the Boar's Head," Michele looked quizzically at her lover.
Polly lowered her head.
"Dr Marron told me. Amanda has assigned me as your chaperone while you learn the ropes. I stopped him when he left your house and he told me that he liked the sex so much that he tipped you a fiver."
"That's also how I knew that Gerald Bramley would leave the hotel when he did. I knew he had an engagement at nine-thirty so I waited across the street."
"So you're my pimp! Is that it?' Michele was angry.
"Michele; I told you that Amanda Holliday had assigned me to you to teach you the feminine arts but she also assigned me as your chaperone for your first few engagements. She likes to make sure the punters are satisfied but also she wants her girls looked after," Polly explained.
Polly reached out and tried to stroke Michele's thigh but she backed away.
"I'm no different to you Michele. I do what I do because I like it and it pays. But I'm also a captive to blackmail," Polly went on.
Michele was about to interject but Polly put a finger to her lips and went on to explain.
"I started at CMH not long after Dr Lovejoy; and after a couple of weeks he seduced me; not that I needed much seducing, he's a handsome doctor and he does have a way with the ladies."
"And then I got invited around to Matron Holliday's place. I was flattered; a first year nurse being invited to the Matron's house."
"I had too much to drink, but to be honest I didn't resist. Amanda and I... well we made love...had sex... call it what you like."
"I won't deny that I liked it; I'd experimented at school with other girls but Amanda was so adept, so experienced and such a considerate lover. I really liked it and I still do."
"But..."
"Just like you, I was secretly filmed `inflagrante delicto', Matron likes to use that term, with Amanda; filmed by Dr Lovejoy and of course they blackmailed me."
"I know your life would be ruined if it got out that you are a transvestite; but I'm in the same situation."
"If my family knew and if it was made public that I liked `tipping the velvet', my life would be ruined."
"My family would disown me and I'd never get a nursing job anywhere," Polly was crying and Michele comforted her, hugging her and stroking her hair.
"But I'll be honest with you; I quite like my life now. I like being a nurse but I love being a prossie. I know that sounds disgusting but it's true, I like the sex and I like the money," Polly looked sincerely at Michele.
"And if it hadn't turned out like this I wouldn't have met you," she pulled Michele's face to hers and kissed her.
"You're my best of both worlds; a woman with a cock," she snickered.
"You fucking bitch you're just using me!" Michele laughed and fell on Polly.
The tea went cold, stockings got ruined, and lust got sated as Michele and Polly rolled around the bed for another hour.
The phone rang after they had both showered and changed. Polly was dressed for a lazy Sunday and Michele had transformed back into Michael.
Polly took the call and stayed on the phone for about three minutes scribbling on hotel stationery.
"Fuck, well there goes our Sunday," she said.
She ripped a page off the notepad and handed it to Michael.
"You need to be dressed as Michele at two o'clock this afternoon. A hire car will pick us up at your place."
"What?" Michael asked incredulously.
"Welcome to our world. We're going to the Richmond Estate; you've heard of it, it's the estate owned by Peter Sinclair; head of the Board of Administrators of Chelmsford Memorial Hospital."
Polly glared at Michael and he knew not to ask questions just listen.
"Michael; this will be a group sex session, an orgy if you will. I didn't think Amanda would throw you in the deep end so soon but I don't have time to explain now."
"I'll get taxis for us both to take us home; I need to prepare and so do you. I'll come to your place at four and explain in detail."
"Matron has left you a package; the ensemble she wants you to wear; no nurse stuff for this job."
"Come on, get packed and let's get the fuck out of here!"
Michael hurriedly packed up all of Michele's accoutrements while Polly called the taxis. There was little time and she kissed him on the cheek when the front desk called to say the taxis had arrived.
"I'll see you at four, have a couple of stiff drinks ready. Give me five minutes and then go down and get your cab, no need to stop at reception; its all taken care of."
During the ride home Michael pondered all that Polly had said. The tangled web in which he was caught just kept getting more intricate. But he trusted Polly and so he followed her instructions. When he arrived home he found a package on the doorstep and he picked it up and hurried inside.
He took his time preparing; he shaved his face and his body, removing any stubble. He used the douche and showered again, applied makeup and then opened the package.
It contained a red satin evening gown; he laid it out on the bed and he appraised it, determining what lingerie and accessories would most accentuate the ensemble.
The shoulder-length brunette wig was an obvious choice, as was the white satin suspender belt, silk knickers and brassiere. Black patent-leather high heels were a given but too much black would spoil the appearance so he selected a pair of tan stockings with chocolate seams and welts.
In his conscience he transitioned from Michael to Michele as soon as he started dressing.
She had donned her lingerie, wig, and hosiery. The satin evening dress felt sumptuous; it fitted her like a sheath and it heightened the sensual feel of her lingerie and stockings against her freshly shaved skin. She stepped into her heels and looked for accessories. She slipped gold rings on fingers of both hands, an elegant gold ladies watch on her left wrist and a gold bracelet on her right, she clipped a pair of drop earrings to her ears and an elegant pendant around her neck. She turned to the mirror.
She looked stunning. The gown was split up one side and showed off her elegant, shapely, gossamer-hosed legs to perfection.
She looked like one of the professional women or doctors wives who turned up their noses to the lowly hospital staff at the hospital's social gatherings.
Two cigarettes and a G and T later there was a knock at the door. Polly, right on time!
Polly arrived looking stunning; she too wore an evening gown, the black satin evening dress was spilt to the waist on both sides. When she sat down the gown opened and displayed her shapely thighs. Her makeup was perfect; her hair coiffured and her gold jewellery caught the lamplight. She was holding a gift-wrapped package.
They sat down on the couch, both smoking and drinking large gin and tonics.
"These parties are full on Michele. There will be people there you recognise, some nurses from the hospital working their second jobs and some high-ranking executives from CMH. Don't worry about any of them; just go with the flow," Polly said.
"But you said it will be an orgy; what do I make of that?" Michele countered.
"It will start off just like any other party, people will chat and drink too much. But yes eventually it will become a group sex party. Some will pair off and disappear in to the bedrooms and some, most of them actually, will stay in the main room where they will engage in group sex."
"I've been to a few of these gatherings and the trick is to just enjoy it as best you can. The pay is lucrative but you need to be prepared for some unsavoury types. It's ok to say no if you don't like what is being proposed to you but you will be expected to participate and it will involve multiple partners. Are you up for it?"
"Fuck it! Let's do it," Michele drained her drink.
"But Polly, if I'm out of my depth; please assure me you will be close at hand to help," Michele took her hand and squeezed it.
"I promise," Polly replied.
There was the toot of a car horn from outside.
"Ok, that's our car, lets go," Polly picked up her purse.
"Here, a present for you. Not from Matron; from me," she handed the gift-wrapped box to Michele who tore it open to find an elegant clutch purse.
"You can't take your, keys, cash, makeup and cigarettes in a satchel babe; every girl need a nice purse."
"And... every transvestite's secret weapon; courtesy of the CMH pharmacy" Polly laughed and produced a tube of lubricant.
Michele kissed her and scooped her keys, some cash, cosmetics, and her cigarettes into the purse, dropped in the lubricant, and crooked her arm through Polly's.
"Let's go and party then," she smiled.
They nattered in the car during the drive to the Richmond Estate; Michele quizzed Polly about what to expect and Polly answered as best she could explaining that all the parties were a little different. Twenty minutes after departing Michele's house the car pulled up to the imposing entrance to Richmond Estate.
Michele negotiated the marble steps gingerly in her heels; this was the first time she had been outside dressed as a transvestite and it was exciting. The limousine driver had made no effort to disguise his ogling of the two sexy passengers sitting in the backseat of his car. Both Polly and Michele's evening gowns were not really designed to be worn sitting in an automobile and both had displayed more leg than was considered courteous. The driver was obviously not offended and his eyes strayed to their sexy-stockinged legs, more than was wise to engender safe driving. But Michele was flattered; the driver either hadn't clocked her as a tranny or he just didn't care.
There was no need to knock; the door was unlocked. They entered an impressive hallway and made their way to a room from where the noise of a party in full swing emanated. There were about twenty or so well dressed men and about a dozen or so elegantly dressed women. Most were chatting in small groups and Michele recognised quite a few of them.
Dr Lovejoy was chatting with Matron who was wearing a gown that barely contained her ample figure, her breasts were overflowing from the bodice of her dress and her legs were displayed magnificently by the split sides. Dr Marron was part of their small group and then she saw the man she now knew to be Gerald Bramley; he looked over and smiled. Quite a few of the other women at the gathering were nurses that Michele knew from CMH, but not that well; they mostly worked on other wards or had different shifts.
Polly guided Michele over to the bar; the place smelled of booze, cigarette smoke and perfume.
"It's a self serve bar and there are plates of canapes scattered around the room, though no is really here to eat. There are no house staff working tonight. Discretion is everything with these people," Polly explained.
They loaded up on gin and tonics and drifted around the room. They deliberately stayed away from the Matron and Dr Lovejoy. Most of those they talked too were very polite and courteous but a couple of the men couldn't hide their distain for the transvestite; Michele was aware that she was not to everyone's taste. Encouragingly all of the nurses who they chatted to were amazed at how dazzling Michele looked and those who knew her as the male nurse Michael Nyland were absolutely flabbergasted when they realised who she was.
Michele was enjoying being out and about for the first time but she knew that without Polly's presence, she wouldn't have the courage to be here.
Three drinks and an hour and half later the demeanour of the party began to change. The lights were lowered and candles were lit; soft music played on record player. Some couples paired up but as Polly predicted most stayed in the main reception room. Men were kissing and groping the women and clothing was being removed. Some of the women had stripped down to their lingerie and some of the men were naked.
An older man with a large belly was sitting in armchair, head back, enjoying being fellated by Matron Amanda Holliday; he'd freed her tits from the bodice of her gown and was pawing at them while she sucked on his impressive member.
Michele was talking to two men who had moved over to as soon as Polly went to the bar to pour more drinks, leaving her alone.
They introduced themselves as Charles Longford and Stephen Mortlock. Michele recognised them as hospital administrators. Michele felt comfortable in their company until they started to crowd her and ease her over to a large couch.
"We're looking to have some fun Michele and we both have a penchant for transvestites" Charles Longford said.
"You are here for fun, aren't you Michele?" Stephen Mortlock smiled impudently at her.
"Ok...sure...I mean yes," Michele whispered.
"There's a good girl then," Charles said.
Charles moved into Michele and forced her against the back of the couch.
Michele felt trepidation as she was pulled into Charles's arms and he kissed her full on the lips, sliding his tongue into her mouth, encircling her in his arms. Michele forced herself to relax as accepted his tongue, pulling her body hard against his; she felt his cock begin to swell against her body. Charles took Michele's hand in his and moved it between their bodies down into his crotch and grunted into her mouth.
"Touch it Michele; you know you want to."
Michele reached out and tentatively stroked Charles's tumescent member through his trousers. It felt big and hard and although she was sure it was her imagination, it appeared be throbbing though the expensive fabric of his suit. Charles's cock tented the front of his trousers and he gave out a little moan as Michele cautiously fondled him, her ruby-red fingernails scratched at the fabric of his trousers as she slowly and excruciatingly traced the outline of his cock.
"Take it out please Michele," Charles panted into her mouth and then crushed her lips with his.
He was pushing his groin against Michele's body, trapping her hand between them, as she stroked the bulge in his pants. His tongue wriggled in her mouth; the taste of her lipstick and scent of her perfume further arousing him. He pulled his groin back from Michele's body and took her hand off his tented trousers and guided her fingers to his zipper.
Charles impatiently tugged at her hand until she capitulated and slowly started to unzip his fly. The chafing sound of Charles's zipper opening was lost in the groans of pleasure coming from all over the room.
Michele looked over to see that the older gentleman who was with Matron had her kneeling on an overstuffed armchair and was fucking her doggy style, her dress hiked up her back while he reached around her played with huge tits. Dr Lovejoy was standing close by improving an already impressive erection.
"Now this is my type of party!" Stephen Mortlock exclaimed.
Michele's fingers hesitantly explored the opening in Charles's flies and soon found sleek, hard flesh. She wrapped her fingers around Charles's long thick cock and felt him shudder against her. She began to stroke him inside his pants.
Charles broke their kiss and took Michele by the shoulders and eased her body away from his a little.
"Take it out please; I want to see you take it out," he whimpered, his lust evident.
Michele's painted fingernails plucked at Charles's belt.
Michele opened the waistband of Charles's trousers and his pants fell down around his ankles. His cock sprang upright between them; the tip of his purple glans glistening with silvery pre-seminal fluid, peeked from the hood of his foreskin. Charles's cock was enormous, at least ten inches long, pink and thick. His foreskin stretched around the bulbous glans. The dark turkey-skin of his scrotal hung down between his legs; a musky odour floated up from his crotch and invaded Michele's nostrils.
Michele gasped but Charles as he took her hand and placed it on his manhood and watched as Michele gently wrapped her fingers around it; her ruby-red fingernails contrasting with flesh of his shaft. She slowly eased her fingers down the shaft, pulling back the foreskin, and exposed Charles's glossy purple glans. The musky aroma intensified.
Charles pulled Michele back against him and smothered her with passionate kisses. She eagerly stroked Charles's enormous phallus, it stuck out from his groin between their bodies, throbbing in her fingers.
Charles loved the feathery feel of her fingers loosely caressing his turgid member. Michele gripped his penis and stroked the hard phallus until he reached down and firmly disengaged Michele's fingers from around his shaft.
"I'm not ready to climax yet miss," he panted into her mouth and then pressed his lips against hers again.
Charles pulled Michele's body hard against his again, enjoying the feel of his member against material of her dress. He held her body against his and his other hand slid down her body and rested on her buttocks. Michele's gasped with pleasure at Charles's tender kisses, his lips pressing against hers and his tongue exploring her mouth.
Charles fondled Michele's buttocks and the material of her gown slid effortlessly across her plump rear, her satin dress slithering against her silk panties. The sounds of rustling of silk and satin, and the smacking of lips and slurping tongues and the smells of perfume and the musky smell of sexual arousal filled the air.
Stephen Mortlock was watching intently and had taken out his penis; slowly improving the erection that stood out proudly from the flies of his trousers.
Sensing Michele's arousal, Charles pulled her body against his and kissed her passionately, there was no resistance and Michele enthusiastically returned his kisses, her tongue flicking against his. Charles's erection was now at full tumescence as he humped up against the front of Michele's gown and scrunched her buttocks through the layers of silk and satin.
He reached down and put his hand inside the split in her gown and then slowly started to lift her dress up. Michele tensed but forced herself not to resist. When Charles had the rear of Michele's gown hiked up he reached between their bodies and grasped the front and hiked it up as well so that the hem of her gown was rucked up around her waist.
Michele stood on her tiptoes, raised up on her high-heels, leaning slightly forward, her arms around the large solid man, she eagerly returned his kisses and Charles rubbed the delicate material of her dress against her tight pantied buttocks.
Charles's cock was now rubbing against the front of Michele's silk panties sending waves of pleasure through his body. He reached down and took Michele's hand and guided it to his rock-hard member.
"Slowly," he groaned into Michele's mouth.
She understood what he meant and took the hard pulsing flesh in her hand and softly squeezed it until she felt Charles buck against her; she ever so slowly began to masturbate him. She was surprised by the girth of his member and the by heat radiating from it as it pulsed in her hand. She masturbated him with long slow strokes, establishing a steady rhythm. Charles moved his groin back and forth in time with her strokes, fucking her hand.
After a few minutes of intense stimulation Charles slowly started to walk Michele backwards until she felt the edge of the couch seat against her legs. He pushed her down so that she was sitting in front of him, her hand still stroking his enormous member. Michele knew what was coming next and her penis began to swell in the confines of her knickers.
Charles removed Michele's fingers from around his phallus; it stood out from his body, proudly erect, quivering inches from her eyes. Pulsing veins encircled the meaty shaft and a silvery thread of pre-cum oozed from the eye of his glossy purple glans down to her lap, soaking into the glassy material of her dress.
Michele's cock hardened as Charles put out a hand and pulled Michele's face towards his erection and thrust his hips forward until his glans touched her lipsticked lips. Michele tentatively flicked out the tip of her tongue breaking the string of pre-seminal fluid that hung from Charles's cock.
Charles gasped as Michele began to slowly lick his cock. She worked her tongue around the bulbous head until it glistened with her saliva and then she ran her tongue up and down the shaft concentrating on the delicate frenulum. Charles watched the sophisticated transvestite attend to his phallus with her tongue. He stood this for a minute or two but then became impatient and pushed his member against her lips signalling his need.
Michele understood and opened her mouth as far as she could, and allowed Charles's massive penis to push over her lips and inside her warm moist mouth. She concentrated on her breathing as about six inches of slick hard cock slid into her mouth until she began to gag.
Charles eased himself out of her mouth a little until she had her gag reflex under control and then he began to leisurely fuck her face. Michele submitted and stretched her lips around his shaft and slavered at his glands with her tongue; her hand slid inside her dress and she stroked her penis through her knickers.
Charles was close to coming and although he was enjoying being fellated he wanted more. He wanted to possess this attractive man-woman. He pulled his penis from Michele's mouth with audible plop and it wobbled in front of her eyes.
"Stephen Mortlock my friend; are you going to partake?" Charles said to his companion whilst kicking off his pants and shoes.
Stephen Mortlock kicked off his shoes but otherwise remained fully dressed, his long thin cock sticking proudly out the front of his dinner suit; the sleek shaft and glans glistening in the candlelight from the saliva he had used to lubricate it while masturbating, watching Michele fellate Charles.
"I'll be right there colleague," Stephen said.
Stephen had Michele kneel on the overstuffed cushions with her backside up in the air. He knelt in front of her.
"Now young lady; I think you've done this before," Stephen said.
He dropped down in front of her and pushed his face onto hers and began to kiss her passionately.
Michele responded, kissing Stephen and suckling his tongue.
Charles moved behind Michele, and rucked her gown up around her waist, and admired the view: Michele's buxom bottom clad in the white silk panties, her legs encased in diaphanous nylon and feet shod in the sexy black high-heels. He stroked her buttocks through her panties.
Charles eased behind her, pushing Michele's knees apart so that he could position himself between her legs with his immense cock resting on her panty-clad buttocks. He lifted the panty material away from her crotch and slid his manhood inside so that it rested in the crease of her buttocks; the top of his penis covered by her satin panties. He slowly rocked back and forth, his cock rubbing against her crevice.
Michele felt Charles's huge penis rubbing against her rear and realised that soon Charles would want to penetrate her. The thought of that monstrous appendage invading her virginal rear passage was quite daunting. She pushed her backside out and began to hump back and forth in time with Charles's thrusts whilst she scrambled around in her little clutch purse searching for the tube of lubricant.
Michele was kneeling on her hands and knees with Charles dry-humping her pantied bottom with Stephen's erection bobbing inches from her face. Stephen pushed his groin forward and Michele opened her mouth and allowed his cock to slide into her mouth.
Stephen was careful not make Michele choke or gag; he could feel her lips close around the shaft of his cock and her tongue flutter against his glans. He didn't want her to choke and was quite happy that this lovely creature was sucking on his hard manhood and didn't want to spoil the sensations. He humped Michele's face slowly back and forth letting his climax slowly build.
Michele's movements were contributing to Charles's pleasure as he enjoyed the feel of her soft silken buttocks pushing back and forth along the underside of his member but knew that he couldn't keep this up for much longer. Michele guessed correctly that he would soon want to fuck her so she unscrewed the cap on the tube of lubricant and squeezed a good dollop onto her hand.
Stephen was quite amused watching this lovely creature scramble for her lubricant whilst sucking his cock and being dry-humped by his friend,.
Michele reached behind herself and applied the slippery lotion to Charles' phallus. Charles eased the gusset of Michele's panties away from her buttocks. He positioned the head of his penis against her puckering anal bud and pushed.
Despite the lubrication Michele cringed as her sphincter and then the walls of her anus stretched to accommodate the huge phallus invading her back passage. When Charles had eight inches of his cock buried inside Michele he stopped pushing and rested, his hands gripping her wriggling hips as she tried to accommodate his invading member.
"Keep still Michele; try to relax darling," he soothed and playfully slapped Michele on the buttocks.
Michele knew that Charles was right. The only way that she would be able to accommodate the huge organ inside her without excruciating pain would be to relax her rectal muscles. She concentrated on doing just that.
Charles felt the vice like grip of Michele's sphincter and then her anal muscles slowly relaxed. He pulled his turgid member out of her until just his glans remained inside, and then slowly began to fuck her.
Michele felt Charles withdraw, and then slowly fill her again; the path of his member eased by the lubrication.
Charles grasped the sides of Michele's panties and began to ride her, his cock slamming in and out of her tight channel. Charles got into a steady rhythm sliding his cock in and out of Michele's back passage and she began to experience a feeling of fullness that was not unpleasant, combined with small waves of pleasure emitting from her anus.
Charles's had got the angle just right and his penis was stimulating her prostate gland, his shaft was also stimulating the sensitive nerves of her sphincter. She felt her cock throb inside her silk panties.
Charles gripped Michele's panties as he mounted her thrusting back and forth, causing her panty crotch to rub back and forth across her penis and Michele let out an animal groan from deep within her throat.
Stephen watched his associate shag the sexy transvestite and it was obvious that she was enjoying as much as Charles was. He knew that he wouldn't be able to contain himself much longer; she was sucking on his cock with abandon, working her tongue on his glands whilst her lips worked his shaft. He would be coming soon and he held Michele's head by the ears and began to fuck her face.
The two gentlemen and the attractive, sexy transvestite synchronised their thrusts as Charles' rampant penis slid in and out of Michele's soft sexy bottom and Stephen plunged his cock in and out Michele's heavily made-up face. Michele rocked on her hands and knees in time with her devotees' thrusts; she was enjoying it so much and her own cock pulsed inside her panties as rings of pleasure travelled out from her back passage.
Michele felt her panties tear as Charles pulled her buttocks back hard against his groin; he pushed forward with all his might forcing every last inch of his cock deep inside her. Michele pushed back against him as she felt stream after stream of hot spend fill her rectum. At the same time Stephen groaned and his cock pulsed in her mouth ejaculating a flood of semen that she swallowed as best she could.
Some of Stephen's issue dribbled past her lipsticked lips and ran down her chin and she could feel some Charles's juice seep past her ravaged sphincter and run down her thighs and soak into her stockings. Michele's own orgasm rocked her and she ejaculated; filling her panties with semen.
Michele moaned around Stephen's phallus as it squirted the last of his load in her mouth; Charles and Stephen both gasped and groaned as they emptied themselves inside the transvestite prostitute impaled between them. Charles could feel Michele's anal muscles spasm and her sphincter contract, milking him of his seed; whilst Stephen felt her lips slither and slide up and down his shaft while her tongue slathered at his glans extracting every last drop of his spend.
Eventually all three of them began to descend from the pinnacle of their orgasms. Stephen recovered first and pulled his cock out Michele's mouth and then pulled himself away from Michele and began to pull up his trousers.
"Michele; you are wondrous and it was pleasure to meet you!" he chuckled as he zipped his fly.
Charles pulled his cock from Michele's anus with an audible plop. More of his semen ran in a small rivulet from Michele's anus down her thigh and soaked in the nylon of her stocking-tops.
"That was magnificent dear; Amanda will be hearing from me soon requesting your services one on one, so that I can have your undivided attention. Would that suit you my dear?" he asked
Michele, still exhausted from her efforts, nodded appreciatively.
Michele did her best to adjust her clothing. She made her way to the bathroom and brushed her wig and applied finishing powder and lipstick so that she looked presentable. She used some towlettes to clean herself and happy with the results left the bathroom and walked over to the bar.
She sipped a gin and tonic and surveyed the room. The party had transitioned into a full-blown orgy. There were couple and threesomes, even foursomes engaged in lewd and lascivious behaviour. She sought out Polly and found her stripped to her underwear, her face buried between Matron's plump thighs performing cunnilingus while James Lovejoy fucked her doggy-style. An elderly gentleman was enjoying being fellated by the Matron while Polly attended to her needs.
"Well the high polloi sure now how to enjoy themselves," Michele smirked to herself, sipping her drink
A handsome but portly middle-aged man soon joined Michele at the bar; she recognised him but didn't know his name.
"Jasper Paton Chesworth at your service mademoiselle," he dramatically kissed her hand.
"Michele Nylons, full-time nurse and part time transvestite," she replied with a little impertinence.
"Ah! Amanda said that she had something a little special coming tonight. I haven't been with a lady-boy since my Navy days. Used to go down to Bugis Street in Singapore every chance I could get," he smiled.
Michele had no idea what this gentleman was going on about but she was intrigued.
"I haven't a clue what you are talking about Jasper," Michele smiled back and sipped her drink.
"Well I had a penchant for transvestites many years ago when I was a Navy man and meeting you has piqued my interest again. Can we talk somewhere private," he winked at her.
"Sure why not," Michele replied feeling confident after a few drinks and having dealt effectively with Stephen and Charles.
"Well lets take a bottle and follow me," he said, taking a bottle of gin from behind the bar and leading the way to the elaborate staircase.
Michele followed Jasper up to the second floor, where after trying a number of rooms, they eventually found a vacant bedroom. Jasper held the door open for her and then closed and locked it behind them.
Jasper topped off their drinks and they clinked glasses; now almost pure gin, and gulped their drinks. Jasper turned off the overhead lights so that only the bedside lamps illuminated the room making it more intimate.
He pulled Michele to him and grabbed her around her waist. He kissed her passionately and groped her roughly through her gown. His hands roamed her body and one eventually found its way inside her dress. He squeezed her through her sodden, ripped knickers.
"Oww you are naughty!" she giggled.
"It feels like you've already had some fun already tonight," he chuckled; his fingers explored her semen-sodden crevice.
"Well it is a sex party!" Michele replied.
"Yes it is," he laughed and guided her over towards the bed.
He pushed her on the bed and fell on top her. He smashed his mouth against hers. He gyrated against Michele, his tongue working feverishly in her mouth, his lips crushing hers. His hands pawed at her buttocks and he pulled her lower body harder against him. He pushed his erect member against her through her dress while he continued to kiss her deeply.
The gentleman reached a hand between their bodies and adjusted his penis, then his hand flew back to her buttocks and he rucked up her dress and used both hands to caress her buttocks through her panties and pulled her against him.
He ground himself against her, his cock hard against her lower abdomen. She could feel the girth of it though the layers of her clothing.
"Well you certainly aren't one to waste time on formalities are you?" Michele giggled.
Jasper's kisses were hard and insistent; he could taste her lipstick and makeup and smell her perfume. She was a stunning example of transvestite loveliness.
"Yes! Oh yes Michele! This feels so good!" he moaned.
Jasper extricated himself from Michele long enough to shed his clothes. His erection stood out proudly as he fell back on the bed and mounted Michele, wedging his penis between her legs.
"Oh my god!" he groaned and began to hump against her.
He got into rhythm, dry fucking Michele in time with his feverish kisses; slowly circling his manhood against her body. Michele could feel his turgid penis trapped between her pantied crotch and gossamer cloaked thighs. Jasper pushed against her and thrusted his cock into the silken trap made by her nylon-clad thighs and silky panty crotch. He could feel the head of his penis rubbing itself along hers through her panties.
Jasper quickened his pace and his cock began to throb. He pushed against Michele harder and held her so tight that she was afraid that he would squeeze the breath out of her. His tongue was now a wild wet animal, thrashing in her mouth, fluttering and exploring every crevice.
Both his hands clenched her buttocks squeezing them roughly through her panties as he pushed her down into the mattress to the rhythm of his thrusts. He groaned and grasped her buttocks so tight that she was worried he would tear through her panties He pulled her hard against him and she felt his penis begin to pulse and throb. Then he quickly pulled himself away from her.
Jasper rested for a minute, then he moved from between her legs and moved further up the bed kneeling; his crotch level with her face. His hard cock wobbled in front of her eyes.
"Touch it please" he begged.
Michele reached out and gently stroked his turgid member with her fingertips.
Jasper leant back slightly so that he could see her painted nails trailing along his shaft as she masturbated him. A thin thread of shimmering clear pre-come ran from the purple head of his penis and dripped onto the sheets. He reached out and caressed her stocking tops and then worked his way up to her panties. Michele stiffened as she felt his hand go inside her panties and begin to fumble about. She forced herself to relax and he eventually found her soft cock nestled in the crotch of her silk panties and he began to free it from its little prison.
Michele concentrated on slowly masturbating him; she grasped his member tightly and slowly squeezed and then fluttered her fingers against the shaft as she worked her hand up and down his penis. He was obviously enjoying it because he stared at her hand caressing him while he stroked her stocking tops. He finally freed her penis and began to squeeze it gently.
Michele stroked his phallus with firmer faster strokes. He lowered his head and kissed her, gently sliding his tongue along her gums, exploring her mouth. Then he sat back on his haunches removing his hand from inside her panties.
Jasper put his hands on her shoulders and turned her sideways on the bed. He drew himself closer and took her head in his hands and pushed his crotch forward so that his glans nestled between her lipsticked lips. He kept pushing until she opened her mouth and accepted his erection in her mouth.
"Oh yes Michele, suck me you gorgeous thing!" he moaned.
He thrust his sleek-skinned penis in and out of her mouth. Michele could taste the now familiar sweet salty taste that she knew to be pre-seminal fluid. Michele breathed through her nose to compensate for the thick member filling her mouth as she had learned to do. Jasper tightened his grip on her head and eased his cock purposely in and out of her mouth. He pulled it back until her lips circled his purple glans and then thrust forward, forcing his turgid meat deeper into her mouth. Michele moved her tongue around his shaft and could sense his enjoyment. Jasper was moaning and grunting with pleasure.
"Oh you are so naughty Michele!!"
Jasper quickly pulled his penis from her mouth and sat back on his haunches and moved back down to the bottom of the bed. He jammed two pillows under the small of Michele's back and lifted her lower body off the bed. He rucked her dress up around her waist and pulled her legs apart and lifted her high-heels high up off the bed. He sat on his haunches between her outstretched legs, he held her nylon-sheathed legs open; her gleaming black high-heels held high. Her heavy makeup was smeared from Jasper's kisses and sweaty passion; her damp hair was strewn around the pillow framing her face. They were both panting.
Jasper positioned himself further up the bed so that his member rubbed against her panty crotch. He pulled the gusset of her panties to one side exposing the crevice between her buttocks.
Jasper adjusted his member so that his glans was nestled against the bud of her sphincter. Michele could feel Jasper pull the gusset of her panties further across her buttocks so that he had an unobstructed view of his penis poised at her rear entrance; his erect member pushed against her sphincter.
"Just a minute please honey," Michele cooed.
She reached for her purse and took out the tube of lubricant and squeezed a big blob of the cool slippery liquid into her hand.
"Well of course; we definitely need that" he grinned.
Michele tentatively stretched her hand down to Jasper's engorged manhood. It was rock hard and she put her hand around it; it felt enormous and menacing, throbbing in her fingers. Jasper looked down to see her lying there with her legs wide apart, her high-heels held high in the air, her legs encased in her diaphanous nylons with her white silk panties pushed to one side, exposing her buttocks. He watched as her long delicate fingers, their red painted nails glimmering with the shine of the lubricant, slide feather-like up and down his hard cock, coating it with a generous amount of lubricant.
"Ok, I'm ready for you!" Michele moaned.
His hands moved to her hips and she could feel his now well-lubricated glans pressing against her sphincter. The head of his penis slid inside her tight bud.
"Oh God!" she groaned as the second penis within twenty minutes invaded her anus.
Michele lay there with her legs spread, gown hitched up; Jasper's gut hanging over her as he thrusted harder. His eyes closed in concentration and ecstasy as he pushed more of his tumescent member inside her. He groaned and held her so tight and she felt a searing heat as her insides were once again invaded.
Jasper's well-lubricated shaft drove itself all the way inside her; her anus still lubricated with Charles's semen. His cock was so big, and so deep inside her, that it knocked the wind out of her. She felt Jasper's thighs against hers, his skin whispering on her nyloned legs as he ground into her. His large gut was now resting firmly against her tummy and his hands gave way and his full weight pressed down on her.
"Oops, better not fall down," he laughed a little drunkenly.
He pushed himself back up and took his weight on his arms and started to kiss her neck. Then one of his hands fumbled around at the front of her crotch. His hand stroked her sleek thighs as he slowly fucked her back passage.
Jasper began to slowly thrust in and out of her, hardly moving his cock more than an inch in and out; he was panting and slobbering at her neck, kissing and licking her. Michele closed her eyes and relaxed her internal muscles, easing his entrance into her back passage.
Jasper's hand stroked her thighs and groin as he slowly fucked her, he was delighted in the feel of the slinky nylon and satin and silk on his skin; he pushed his crotch hard against her buttocks on the in stroke. He began to fuck her harder and faster, establishing a hard and fast rhythm. Michele relaxed her sphincter and concentrated on keeping her back passage loose to accommodate him.
"Oh that feels so good!" Michele moaned.
Michele opened her eyes and turned to face Jasper. He was thrusting against her, his hand fumbled under the front of her panties, he found her penis and began stroking her. He was alternately kissing her lips and her neck. He thrusted in and out, pivoting his waist to get all of himself inside her, rubbing his scrotum on her silk covered buttocks at the top of his in-stroke.
Her anus was full and it ached as Jasper's throbbing member slid in and out of her, but oh god, the spongy hard mass of his glans felt so good as it pushed against her prostate. She could feel ripples of sexual pleasure from her anal cavity.
Michele raised herself up so that her buttocks pushed back against Jasper and swayed her hips from side to side to increase Jasper's pleasure and ensured her buttocks rubbed against him, as he obviously loved the feel of her silky panties against his skin. She turned her head, allowing Jasper to kiss her pouting lips.
Jasper began to pound himself in and out of her. He grasped her hips and pulled her hard up against him, thrusting forward and back. He jackhammered in and out of her, groaning.
"Oh Michele, this is so good, you are so good, I'm going to come!" he gasped.
He pushed in hard and grated his scrotum against her buttocks as he shuddered. His gripped her waist. Michele sensed his cock begin to convulse inside her as it secreted his hot spend. Jasper's cock filled her completely as he orgasmed deep inside her. Spurt after spurt of hot seed streamed into her as he rocked slowly back and forth.
Jasper's cock pulsated and throbbed against her sensitive prostrate, washing it with his hot seed, she experienced a stab of exquisite sexual pleasure pulse through her and she stiffened and ejaculated into the front of her already semen-soaked panties. Michele shuddered and moaned with pleasure.
Jasper pushed her down into the mattress and pulled his cock back so that it slid out of her. A torrent of semen trickled down her crack and, as he lifted himself up, globs of semen dripped from his member onto her stocking tops and legs.
Jasper kissed her and she kissed him back.
"That was wonderful Michele; thank you," Jasper smiled down at her and climbed off the bed.
He cleaned himself with a towel and dressed while Michele lay on the bed exhausted. She reached for her drink, took a gulp, and lit a cigarette.
She allowed him to leave the room and then cleaned herself with the towel and sat up adjusting her clothing, not very ladylike, trying to get her ripped and soaked panties into some semblance of order, straightening her stockings and smoothing out her now stained evening gown. She sat at the vanity table and fixed her makeup.
She stood up a little unsteady on her heels; the booze and fucking had taken their toll.
Michele clutched the handrail as she gingerly made her way down the staircase. The party was starting to break up, many of the guests had left, a few were still having sex, but most were sated and either gathering their things to leave or sitting in small groups chatting and having a nightcap.
Polly was sitting with Matron Holliday and Dr Lovejoy, now fully clothed and chatting away intently. Michele didn't want to join them but Matron saw her and beckoned her over with a casual gesture. Michele took a drink from the bar and wandered over.
"I've heard good reports about you Nurse Nyland or is it Nylons?" she said.
"I'll see you at work tomorrow," she said dismissively.
"If I wasn't so busy I might have shagged you myself," Dr Lovejoy said, appraising her.
The Matron shot him a malevolent stare.
"Come on Michele, our car is waiting," Polly said, attempting to diffuse the awkward situation.
On the ride home Michele and Polly gossiped like girlfriends, exchanging details of their experiences.
When the limousine arrived at Michele's place there was an awkward silence.
"Thanks driver," Polly tipped him five bob and opened the door.
"I presume I'm welcome?" Polly asked.
Michele spanked her on her cute arse and took her hand and led her to the front door. They kissed and fawned at each other in the hallway.
"I'm not sure I can perform again tonight," Michele lamented.
"We'll see," Polly said dragging her to the bedroom.
To be continued.
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Michele Nylons ???????? michelenylons@msn.com