tagTranssexuals & CrossdressersLady In The House Ch. 17

Lady In The House Ch. 17


Michele spotted the prospect in the mess hall. He was young, slim and effeminate and was in the company of Danny McGregor, a well know prison bully and pederast

Michele was now firmly ensconced as the Madame of the Chelmsford Prison transvestite brothel which operated with impunity in E Wing of the old prison.

She and Steve had had their differences, in fact just over a year ago she had tried to stab him when Steve threatened to force Michele's teenage niece into a life of prostitution on the outside of the jail. It had come to head when Steve had coerced Michele's sister Angie into becoming a prostitute herself; and then Angie had turned the tables and now ran Steve's Escort Agency assisted by Michele's predecessor Carmel.

The business was thriving; providing sophisticated whores for Steve's clientele as well as a lucrative sideline in transvestite prostitutes run by Carmel.

Michele and Steve had a cordial relationship; with Michele running the prison brothel for Steve while Steve concentrated on his other illicit business ventures both inside and outside the jail. The E Wing brothel was thriving under Michele's management; she had been a successful businessman in her former life, which now seemed like an eternity ago, and she had introduced some innovations into the business.

Michele also cared for her wards, prison inmates who had become transvestites under the tutelage of Carmel and later Michele. Some had been only too willing to become crossdressers and loved the debauched lifestyle of E Wing and others had been coerced. But Michele made sure they were well cared for and well paid for their services.

The brothel thrived; there was nowhere else the inmates could get sex except for the odd conjugal visit or maybe a quick blowjob or handjob during visiting hours if the guards weren't looking. Some inmates were openly gay and had entered into prison 'marriages' with other men but the so-called straight inmates took advantage of the transvestite brothel. Why wouldn't they; the 'girls' Michele had working for her were feminine and sexy.

Michele didn't need to mix with the general population, or 'gen pop' as the inmates called it. As Steve's Madame, and also his Mistress, Michele was immune from the drudgery of prison life and both the inmates and guards gave her due respect. She didn't even have to return to her cell if she didn't want to; she had her own cell in E Block that was more like a five-star hotel room than a prison cell.

But Michele occasionally went back to her comfortable but not quite luxurious cell in F Black, wore drab (male clothing) and slummed it with the other inmates. She did this for a number of reasons. One was because she didn't want to ever forget what awaited her if the lucrative prison brothel was closed or Steve kicked her out, and the other was that she needed to find new 'girls' to replace her charges when they were paroled or for whatever reason no longer willing to remain transvestite prostitutes.

She had a stable of ten girls; they lived in gen pop and arrived for work every afternoon in the E Wing brothel, transforming and then proceeding to their workroom cells to tend to their clients.

Some of the girls had boyfriends in gen pop and neither Steve nor Michele much cared as long as the girls realised that they belonged to Steve and were willing to perform their duties every evening and on weekends. Their boyfriends knew better than to interfere with the girl's employment; Steve was ruthless and saw his girls as a commodity that he owned.

Michele fawned over them, helping them buy new clothes, shoes, lingerie and makeup when they needed it; tending to their welfare and making sure that they remained healthy and disease free. But she was also their boss and wouldn't take any shit from them and they knew better than to cross her.

Michele sat sipping her soup watching the young prisoner sitting next to Danny McGregor. The lad was obviously miserable but that didn't stop Danny pawing at him while the poor inmate dissolutely ate his lunch. Michele could only imagine the nightmare the poor guy was living, being constantly forced to provide sexual favours for the fat, hairy, bully. An image of Danny sweating over the young lad as he pounded the boys pale skinny arse popped into Michele's head and she shook it free with distain.

That evening she lounged on the couch in Steve's office sipping a nice single malt scotch chatting with her boss. She had deliberately allowed her skirt to ride to expose her long slim legs; the dark welts of her stocking-tops just visible. She knew this drove Steve wild and guessed that she was going to receive a good hard fucking later, going on the lustful glare in Steve's eyes.

He reached out and pulled her close; his hand sliding under her skirt as he kissed her passionately. Michele responded and her cock began to thicken inside her satin panties. But there was business to discuss; the sex could wait for now. She gently pried herself from Steve's embrace and pulled down and straightened her skirt.

"Spoilsport," Steve grinned at her sipping his own drink, confident that Michele would resume teasing him as soon as he was ready for some lovin'.

"Later honey," Michele grinned back; her hazel eyes sparkled, enhanced by her eyeliner, mascara and exotic eyeshadow.

"I've found a new prospect," Michele began and Steve instantly became attentive.

"That fucking pervert Danny McGregor has taken a young lad captive; can't be any older that twenty-two and a perfect candidate," Michele explained.

The look of distain on Steve's face was evidence of his dislike for Danny McGregor.

"I should have taken care of that fucking noncer ages ago," Steve spat.

"Well I need you to free up the young bloke and we need to do it in such a way that I can get my clutches on him and see if he's a suitable candidate for our stable," Michele went on.

Neither of them saw the irony in their plan. They intended to free a young man from the clutches of violent pervert but only because their intention was to turn into a transvestite prostitute. But that was what passed for morality in Her Majesty's Prison Cheltenham.

It was all too easy in the end.

"Hey Danny; you wanna pop by E Block for a freebie?" Steve asked.

"Why would you do that for me Steve? You and me ain't exactly best friends," Danny asked cautiously; but Steve could see the lust in his eyes.

"Well I wouldn't mind an hour or too with your lad," Steve grinned.

"Never would have thought you for the type that liked em' young. Thought you had enough on your plate with those tranny whores you run," Danny grinned.

Steve was going to enjoy sorting out this arsehole but for now he just smirked.

"Well variety is the spice of life," Steve replied.

"See you tonight then," Danny grinned back; and reached out and cuffed his young acolyte across the ear.

"I hear Steve's got a big one young un'; you better not tighten up on him or it'll hurt like a bitch," he snarled.

Steve hid his look of disgust and moved on.

That evening as Danny made his way through the abandoned cafeteria of E block, heading for the well disguised door that lead to the opulent brothel that Steve and Michele ran inside the prison, Steve and Michele watched their progress from a dark corner. Danny was almost dragging the young man along, anticipating wetting his willy in one of Michele's attractive crossdressed whores.

Danny never saw Steve's henchman come up behind him. He knocked him to the ground and Steve burst from his hiding place and began to kick the shit of Danny.

Michele came out of the shadows and quickly took the startled young man by the wrist.

"Quick! Come with me! You don't want to be around here while this is going on," she whispered.

The young man allowed Michele to lead him away, through a door that lead to a refurbished shower block where the transvestite prostitutes transformed from prison inmates to sexy transvestite hookers.

The young man looked around amazed at his surroundings. He had left the dusty, bleak detritus of the abandoned jail block and stepped into a world of opulence. A line of mirrors above a counter packed with cosmetics, perfume and feminine accessories. A series of different coloured, and different styled wigs stood on wig-stands. A line of sheer dressing gowns hung on hooks on one wall. The whole place was tiled and lit by overhead fluorescents and spotlights. A number shower stalls and sinks were located in an ante room off the main dressing area. The place smelled of perfume and cosmetics; it smelled wonderful to young man who had to live with the stink of gen pop.

"This is where my girls get ready before they go into their workrooms," Michele answered the unasked question.

"But they're not really girls though are they," the young man blurted out and then blushed with embarrassment when he a saw a flash of anger in Michele's eyes.

"Well they come through that door as men; but within an hour or so they emerge as beautiful women; just like butterflies," Michele smiled at him.

"Like you," the lad smiled sheepishly.

His eyes roamed over Michele's body and she could see his admiration.

Michele was dressed in a charcoal-grey business suit; the jacket tight at her slim waist; the hem of her skirt rested six inches above her knees displaying her shapely, gossamer clad thighs to advantage. She wore a cream satin blouse, a hint of black lacy bra just visible at her décolletage. Her heavily made up face was framed by a sleek black bob; the wig shone in the harsh lights.

Her long shapely legs led down to her feet shod in black pumps with four-inch heels; her legs were clad in shimmering flesh-toned hose.

"Yes like me," Michele winked at the lad.

"You like what you see?" Michele asked; giving him coquettish smile.

"Yeah I like girls...........err I mean............real girls," he stammered.

Michele giggled.

"What's your name anyhow?" Michele asked.

"Brian," he answered; looking down and scuffing his boots.

"And Danny was using you as his girl," Michele said.

"Fuck off; I don't wanna talk about that," Brian whined.

"But you would rather be treated like this," Michele whispered and moved in close.

Brian smelled her perfume and makeup and Michele saw his erection in his jeans. She smiled to herself and lifted his face and placed her lips on his.

Brian gave a pretext of pushing Michele way but it was half-hearted. Michele put her arms round him and drew close, exploring her mouth with her tongue. Brain responded his tongue slid into her mouth and they kissed passionately.

Michele could feel his youthful cock throbbing in his jeans and knew the lad wouldn't last long. She gently eased him away and dropped to her knees. She unzipped his fly and heard him gasp.

Her fingers found his manhood and freed it from the confines of his underpants and she gripped his hard member and squeezed.

"Oh my god!" he moaned; and Michele lowered her mouth to his glans just as his seed erupted.

Michele sucked the young man dry as his knees shook; he nearly collapsed. He had to hold onto her shoulders to stop himself fainting as his cock unloaded into the stunning transvestite's sensuous, red-lipsticked mouth.

Michele slathered her tongue along the ridge of his glans and then swallowed his cock; her lips working their way up and down his shaft, milking the last of his spend from his pulsing member.

When she had sucked him dry; she stood on her heels, Brian was still gasping and obviously embarrassed. Michele kissed him and he tried to pull away but she held his face still and tongue kissed him. When she broke the kiss Brian stepped back just a little.

"I can taste my stuff on you breath," he whined.

"You get used to it; I'm sure Danny left his taste and smell all over you after he'd finished with you," Michele replied.

The young man began to cry.

"Fuck you are so beautiful; but you're a man," he sobbed.

"I'm just Michele," Michele smiled sweetly ay him.

"But I've seen you in the mess hall when you're Mike; you look just like any other guy in here, just smooth-shaved and slim. There are plenty of other guys like that; I mean like me, who the noncers force to be their bitches."

"But when you are dressed like this you are beautiful, sexy and feminine; and no one dares just touch you. Just like Steve's other trannies," Brian blurted out.

Michele slapped him across the face.

"Don't call me a trannie; it's a derogatory term. Us girls are proud of who we are and what we do," she snarled.

"We're not like you white-trash rent boys; we choose to do what we do and we are beautiful and sexy. We aren't women but we are the closest thing to it in Chelmsford," Michele retorted.

"Now fuck off back to gen pop; Danny won't be coming for you anymore and hopefully the other noncers will leave you alone for a while," Michele barked.

"But not for long I bet!" Michele called after him as turned on his heels and fled.

Later that evening Michele was reading a fashion magazine in her E block apartment; the brothel was closed for the evening and Michele was relaxing and drinking a glass of wine. Steve strode into the cell and smiled at his Madame.

"Was it a good night?" he asked.

"Yes, particularly so. About ten inmates and four guards; all paying customers, plus the warden came around for his weekly special with Leila. He knows he doesn't have to pay but he always drops a hundred pound tip on the way out," Michele smiled.

"And the other thing? The rent boy that Danny had taken hostage?" he asked.

"I planted the seed; he'll be back to see me," Michele grinned.

"Did you let him fuck you?" Steve asked; Michele detected that a little jealousy crept in his voice.

"No we are nowhere near that stage yet, but I gave him the fastest blowjob I've ever given," Michele laughed.

"It shouldn't take me long to convert him," she said, suddenly serious.

"So you haven't had a good fucking today then?" Steve asked mischievously.

"I haven't had a fucking of any description today," Michele smiled back.

"And to be honest, I haven't met a man today worth fucking," she said sarcastically.

"Get over here you bitch," Steve said; his voice hoarse with lust as he reached for her.

"Ok. I supposed you will have to do then," Michele laughed but her voice was thick with desire.

Michele and Steve fell into each others arms and kissed and rubbed against each other. They both had often had sex with other partners but the best sex they had was with each other; they knew each other's wants and needs so well.

Steve groaned and kissed his transvestite girlfriend frenziedly; he eased her back onto her queen-sized bed and fell down on top of her, never breaking their kiss.

He humped away at her, his need for release overwhelming. Michele reached between their bodies and opened his flies and freed Steve's cock from his trousers; it felt long, thick, and meaty; it was as familiar to her as her own.

Michele guided Steve's penis under her skirt so he could rub it on her satin panties and silky stocking tops. She knew Steve loved this and he responded by rubbing his cock in long slow strokes; she felt his cock press against her own; the layer of sleek satin panty enhancing both their pleasure.

He kissed her and groaned into her mouth and she responded by kissing him back and rising her groin up off the bed to meet his thrusts. She rucked her skirt up out of the way.

She reached out and scrambled her fingers around the bedside table reaching for the lubricant she kept there and slathered his phallus with the greasy gel. She had lubricated herself internally in anticipation of Steve's arrival.

Steve didn't even remove her panties; he simply slid the gusset to one side and then slowly slid his entire length inside Michele until his scrotum rested against her buttocks. Michele grunted as Steve's cock filled her, but she liked the feeling of the hard member crammed inside her and she especially liked the tingling feeling emanating from her postrate whenever Steve's glans rubbed against it.

Their fucking was almost savage; Steve pounded away at Michele as she rose her buttocks up off the bed to meet his thrusts. They never broke their kiss and they gasped and groaned into each others mouths as their tongues entwined and teeth occasionally cracked together with the ferocity of the sex. Steve had managed to shuck off his shirt and when Michele bought up her legs and wrapped them around him he savoured the feel of Michele's stockings rubbing against his skin.

The fucking became a frenzy, Steve jack-hammered his cock in and out Michele's tight anus and Michele, impaled on Steve's hard throbbing cock, clung to him and wriggled and shook her buttocks, goading him on and increasing her own pleasure. She thrust her hips upward to match his strokes ensuring the full length of throbbing phallus penetrated her slick anal sheath. She crossed her ankles behind Steve's back, her stockings hissing as they rubbed against the sensitive skin of Steve's flanks.

Michele felt her orgasm approaching as Steve howled and moaned with the rush of his own climax. Michele felt Steve's cock convulse deep inside her as he filled her with his hot seed. Michele's cock was erect and rubbing against Steve's stomach through the flimsy material of her panties as Steve savagely fucked her. The pressure and friction induced Michele's own climax and she groaned in ecstasy as she flooded her panties with hot semen. Steve's cock pounded in and out of her anus further stimulating her and she experienced an intense orgasm.

Steve's thrusting slowed down as his orgasm subsided and eventually he lay still on top of Michele with his slowly deflating penis buried in her anus. He was still kissing her and he could tell that her orgasm was still raging through her body, he felt her penis convulsing in her panties and her hot seed flooding through the panty material and soaking his belly.

Michele's climax began to subside and as she came down from the sexual high they remained in each other's arms; kissing each other softy and tenderly. When their passion had subsided, Steve eased himself from her embrace and went over to the sink to clean himself while Michele lay there holding her skirt away from her semen soaked panties.

Steve bought a moist towel over and gave it to Michele; she cleaned herself while Steve poured more drinks and lit them both a cigarette.

Michele got up and dried herself and snagged a pair of fresh panties out of her dresser drawer.

"So this kid Brian? He looks like a good prospect?" Steve asked sipping his wine after taking a long drag of his smoke.

"Yeah; I'll convert him," Michele smiled back; blowing a stream of cigarette smoke Steve's way.

She was sitting on the bed and her skirt was still hiked up a little; her smooth thighs and fresh pink nylon panties on display. She dangled a shoe; exposing the reinforced heel of her stocking. She saw Steve was staring and smiled.

"You wanna go again?" she asked; her own lust reigniting.

"Just let me finish this fag and you better be ready," Steve grinned.

"Promises, promises," Michele teased.

Steve stubbed out his smoke and fell on her; Michele's laughter soon turned to squeals of delight.

To be continued...........................

Feedback to the author is always appreciated and encouraged. Thank you avid readers.

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