Chapter 5: 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.