tagTranssexuals & CrossdressersLady In The House - Reprised Ch. 18

Lady In The House - Reprised Ch. 18


I decided to end this story a few years ago but I keep getting requests to continue it; particularly from my fans here at TVChix. I have been thinking about it of late and I finally came up with a few ideas to keep the story going. So here it is..........Lady In The House reprised.

For those that don't remember; the story ended like so:

Steve sat on the edge of my bed and I was on my knees between his legs sucking eagerly on his erect penis. His head was thrown back in pleasure and his eyes closed as his orgasm approached. As the first stream of hot semen erupted from his cock into my mouth I snaked my hand out and reached under the mattress.

My hand closed around the handle of the shank that I had hidden there earlier...

The End....................But it wasn't, was it............................

One year later............................

Michele obediently leaned over the desk as soon as the man entered the room; she opened her legs slightly and bent forward resting her elbows on the mahogany desk top. The man moved behind her, admiring her well-propositioned buttocks straining the navy blue material of her business-suit skirt. He liked the way the kick-pleat opened up to expose her silken-clad thighs; the dark welts of her stocking tops just visible.

He unzipped himself as he positioned himself directly behind her and Michele compliantly hiked her skirt up her taut thighs; the material of her skirt whispered against her sheer nylon stockings. She felt his member prod at her buttocks.

"Do it!" the man ordered.

Sometimes the man liked to rub his erection against her panty-clad arse, sometimes, like today; he just wanted to enter her and get on with the sex.

Michele reached back and pulled the gusset of her red satin panties to one side, exposing her anus. She positioned the tip of the man's glans into the crevice of her sphincter. She knew what would come next and leaned back a little a further and raised her buttocks; her own erection was tenting the front of her skirt.

She had already self-lubricated her anus; it was a requirement, and when the man's long thick cock slid into her it met no resistance. Michele had accommodated this penis hundreds of times and she sighed almost contentedly as the man's groin nestled against her buttocks. He began to slowly thrust in and out of her and she obligingly began to move her behind back and forth in time with his thrusts.

Michele took one hand off the table and reached under the hem of her skirt. She found her erection and eased it free of the confines of her panties. She was allowed to do this; it had been agreed to.

The man gripped her waist and began to quicken the pace of his thrusts; Michele met each thrust with a corresponding shove of her arse, at the same time she stroked her erection. The man knew how to fuck and angled his cock so that it rubbed against her prostate to stimulate her, and the warm glow of sexual arousal pulsed out from the walnut shaped gland in her back passage and amplified the tingling sensation emanating from her penis.

"Now!" the man grunted and began to jackhammer in and out of her well lubricated channel.

It was always like this; if the man wanted to 'make love' to her they would have retired to one of the cells; or 'workrooms' as they referred to in E block; but today, as usual, he just wanted a quick fuck.

This suited Michele; as much as she loved an afternoon dalliance with an attentive lover she had too much work to do today and this quick release would see her through to the close of business.

As soon as she felt the man grip her tighter and quicken his pace Michele dug her heels into the shag carpet and pushed her buttocks back against the man and began to stroke her erection faster and faster; she knew he wouldn't last long now and she wanted to time her climax as close as possible to the man fucking her.

She didn't really care about doing this to stimulate the man fucking her; she knew he was only interested in self-gratification, but it enhanced her own climax if she ejaculated at the same time as the man buried in her arse.

She felt his cock quiver and begin to unload the soupy load of sperm inside her and she whipped her hand up and down her cock, invoking her own orgasm. The man gripped her tightly and pulled her back hard against him, squashing her soft buttocks against his hard stomach as he ejaculated deep inside her. She felt the hot creamy secretions fill her back passage and she gyrated her buttocks to help milk him of his load as her own seed spilled on the cheap rug she had placed on the shag-piled carpet specifically to catch her semen so it wouldn't stain.

Michele was careful to keep her ejaculating cock clear of her skirt; she didn't want to have to waste time later changing it and semen was an absolute bastard to remove once it had dried.

Michele felt her climax begin to subside as did the man standing between her legs. They were both panting; the man stroking her backside in appreciation.

"Here," Michele took a handful of tissues out of the dispenser on her desk and reached behind her.

The man took the wad of Kleenex and placed them against Michele's sphincter as he eased himself out of her, carefully catching and wiping away any of his issue that escaped her tight bud.

When his cock slid free he quickly wiped it and took another handful of tissue from her and carefully wiped around her puckered anus and her creamy white buttocks; careful not to let any of his spend stain her skirt. He politely eased her panties back into place and when she stood up he lowered her skirt and smoothed it across her delicious derriere.

Michele had cleaned away her own issue and slipped her deflating back inside her panties and adjusted them; she smoothed down the front of her skirt and adjusted the hem so it sat straight and level four inches above her knees.

The man gripped Michele by the shoulders and spun her around on her high-heels. He kissed her passionately and she kissed him back. After what Michele thought was an appropriate amount of time she put her hands on his shoulders and gently pushed him away.

"Shall we go though the books now Steve?" she asked; although there was no need to ask.

"Yes lets," he replied all business now that his penis was tucked away snugly inside his trousers.

They didn't always fuck when he came down to E Block; sometimes Steve wasn't in the mood, or he wanted to save himself for one of the whores in his harem; but mostly he did; and Michele was appreciative it. Not that she couldn't fuck any man in the jail if she really wanted to; but she liked the fact that boss liked to fuck her; even after all these years...............................................

Michele had tried to kill Steve a little over three years ago; she had hidden a shank under the mattress of the bed in her prison workroom. She had imagined how it would be:

'She pulled the shank out from under the mattress and sank it into Steve's chest' ................at least that's how it played out in her mind. In reality she was so fucking angry that the tip of the shank got caught in the sheet and jammed. It became entangled in the bedding and she couldn't get it free.

Steve had beaten her badly enough to put her in the prison hospital for a while. Then he came to visit and had given her a letter from her sister Angie. Michele read the letter incredulously

'Michele, (even Mike's sister didn't even think of him as Mike anymore) You don't need to worry. Steve and I have come to an arrangement. As you know, I am nothing if not pragmatic. I have entered into a business deal with Steve; don't worry your niece is safe, she's not part of it, and you needn't worry about me. I won't go into details in this letter but I will tell you that the deal suits Steve and I both. I know you think that I'm not the sort of person who could enter into a life similar to what yours has become; but I have. I will explain all next time I visit Chelmsford."

And it was that simple. Michele didn't have to look out for her sister Angie or her niece Carol anymore. She had no reason to kill Iron-Bar Steve; she just had to look after herself.

Lady in the House - Chapter 18 By Michele Nylons

Three weeks later Michele had recovered from her beating; only a few bruises around her eyes remained; easily covered by eyeshadow and makeup. Michele and Steve sat in the conjugal visiting room which Steve used with the consent of the Warden.

Angie entered and walked straight over to Steve; ignoring her brother, and kissed Steve passionately, rubbing her body against his. Michele was shocked as Angie rubbed up against the man who had been her protagonist, Angie groped Steve's thickening erection though his jeans as he pawed at her buttocks.

Angie was dressed similar to Michele: one part businesswoman, two parts slattern. She wore a white business suit but the skirt was too short for propriety, her high-heels had to be at least four inches, her legs clad in shimmering flesh-toned hose, her hair frizzed out in an eighties style do and her gaudy makeup heavy and exotic.

Angie extracted herself from Steve's embrace and looked Michele squarely in the eye.

"I quit my job. I'm running a brothel and callgirl agency for Steve on the outside. I like the work; I'm my own boss and I'm making a shitload of money. It's that simple Michele," Angie said.

"What about Steve's threat to get your daughter, my own niece, involved in the prostitution business?" I asked incredulously.

"Don't be stupid Michele. You know I'm a very astute businesswoman. Carol is away in a private boarding school with a whole bunch of very proper ladies, while her mother is about to run one of the most lucrative brothels and callgirl agencies in London."

"I'm going to specialise in all sorts of perversions; including having some of the sexiest transvestites on my books," Angie explained as I looked on amazed.

"Carmel is going to help her run the business," Steve added squeezing Angie's knee.

"Carmel's due for parole anyway. I could stop that of course; I have before, but I can put her to better use outside helping Angie run the business out there," Steve explained.

I just sat there incredulously. How could this turn of events have come about in such a short timeframe?

"Oh don't worry Michele; you're getting promoted. You used to be Eddie McManus' bookkeeper and right-hand girl the last time you were in Chelmsford. So you have the skills I need. You're taking over from Carmel, running the E Block brothel for me."

I was stunned.

Steve reached out and slid a hand up my thigh. At Steve's insistence I was wearing a black leather miniskirt, white satin blouse, sheer taupe stockings and black stilettos. My cock quivered inside my tight satin boy-leg satin panties; it was an uncontrollerable response to years of conditioning as a jailhouse transvestite prostitute.

"Now fuck off next door while I fuck your sister. There's a nice surprise for you," he grinned.

Angie plopped herself in Steve's lap and his hand disappeared up her skirt as she kissed him passionately. I had to leave! I couldn't believe what had transpired during my short convalescence.

I followed Carmel into the adjoining room. She stood there grinning. She looked magnificent too! A skin-tight black long-sleeved cocktail dress showed off her magnificent figure; he legs were clad in shimmering silvery hose. Her feet were clad in shiny black high-heeled pumps and her makeup was perfect as was her do; a brunette bob that framed her pretty face. She was still stunning for tranny of her age.

"Looks like you will be the new Carmel; who would have thought it all those years ago when you first walked into Chelmsford prison?" she grinned.

"Yeah! Who woulda thunk it?" I mused, deliberately using jailhouse colloquial speech.

All these years in Chelmsford...........My first stretch where Eddie turned me into a transvestite prostitute and then my second stretch where Iron-Bar Steve was running the brothel and soon had me doing the same. All the debasement and debauchery; I had fought and connived and blackmailed all-and-sundry to try to get out from under; but eventually I had capitulated and even come to enjoy the lifestyle.

"So Michele; we have a few days next week for me to handover the reins of Steve's operation and then I'm finally out of Chelmsford," Carmel grinned.

"How long you been inside Carmel?"

Funny all the years I had known Carmel, I had never asked her this question.

"Too fucking long Michele; look at me I'm an old maid," she smiled wanly.

"Fuck off Carmel, next to me you're the hottest transvestite in Chelmsford prison!" I teased and pulled her into my arms.

She kissed me softly and I responded immediately.

The sweet taste of her mouth, the taste of our lipstick as our lips crushed, the scent of our perfume, the soft embrace of our bodies. I became tumescent; the soft satin material of my panties caressed the sensitive flesh of my penis.

Our kisses become more frenzied and Carmel pulled my body close to hers; my skirt and blouse rustled against hers, the feel of the soft fabric against my skin was electrifying. Her tongue slid into my mouth and I gasped as her fingers slid up my legs; the soft caress of her fingers on my sheer nylon-clad thigh was delightful.

Carmel and I had had sex on many occasions and I always liked making love with her; she was so sexy and feminine. She was after all, the one who introduced me to the delights of crossdressing and the transvestite lifestyle.

I responded and lifted the hem of her skirt and stroked her thighs. She pulled me closer and our tongues entwined.

We stayed locked together and inched our way over to the bed where she fell on top of me. She kissed me passionately while her hands explored my body. Eventually her hand slid up my thigh, across the welts of my stockings, and then across the band of pale tender flesh until her fingers rested on my panty-clad member.

"MMMMmmmm," I groaned as she squeezed it.

Carmel broke our kiss briefly and smiled at me.

"You are a born slut!" she sighed and her face fell back to mine.

I reciprocated and slid my hand under her dress and found her member sheathed in sheer nylon panties. I traced the outline of her erection with my fingernail and she gasped in my mouth.

"Michele; you haven't lost your touch," she gasped and pushed her crotch into my hand, encouraging me to stroke her.

She squeezed me and I took hold of her shaft and caressed it; I stroked it through the gauzy nylon and felt it pulse and quiver in my fingers. Carmel began to masturbate me through my satin panties and the feeling was sublime. I felt so feminine as we mutually masturbated each other, slowly stoking each other through the silken fabric of our panties as we kissed and fondled each other. My other hand explored her stocking-clad thighs and she explored mine.

Then Carmel abruptly broke our kiss. She lay on top of me, looking down on me; her hands on my shoulders her legs between mine. She stared me straight in the eyes.

"You are beautiful Michele," she sighed.

"I'm going to miss you."

"I'll miss you too," I whispered.

Her face fell to my stomach and she kissed me there, then she proceeded to work her way down my skirt kissing me until her lips found the hem. She knelt between my legs as I lay prone on the bed. Her lips found my knees and she kissed them. I shuddered.

She worked her way up my thighs; softly kissing my stocking-clad flesh; her fingers stroked my calves, then the backs of my knees and then her fingers caressed my thighs. She rucked up my skirt and I lifted my head to see her face hovering above my groin. She lowered her face and I feel her soft lips nuzzle my cock through my silky satin panties.

"Oh God!" I groaned as she kissed my shaft and tickled the glans of my penis with her tongue.

She took my penis into her mouth and I thought I would die with pleasure. She suckled it briefly through the satin panty material and then she used her fingers to free my member from my panties.

Unencumbered by my underwear, she took my naked flesh into her hot wet mouth.

"OOOOooohhhhh Carmel!" I gasped.

I placed my hands on her head and she slowly began to fellate me.

Her tongue found my fraenulum and teased it as her lips locked around the base of my penis. Then, as she lashed my glans with her tongue she moved her lips up and down my shaft. Her fingers continued to caress my silken-clad thighs and I lay back in utter bliss as my hands guided her head up and down my shaft. She relocated a hand to my groin and she stroked my scrotum through my panties and gently squeezed while her mouth continued to suckle my erect penis. I was close to coming.

The sensation of being fellated by this seductive transvestite, whilst clad in satin, lace and nylon and wearing makeup, perfume, and high-heels is an experience I still cannot adequately describe. It is pleasurable beyond belief. As my climax approached I closed my eyes. "OOOOoooohhhhhh!" I moaned and writhed upon the bed.

I grasped Carmel's head and pushed it into my groin as I ejaculated. She sucked and slathered my member as my issue unloaded into her warm moist mouth. Her tongue flickered over my throbbing glans while her lips sucked my pulsing shaft as she milked my spend from me; her fingers gently caressed my scrotum to encourage the last of my semen from my scrotal sac.

My feet drummed on the bed, my high-heels clattered and my body twisted and writhed with passion as my orgasm raged through my body. The sensation of the soft sensual lingerie on my tender skin, the feel of skirt, blouse, hose and heels; the taste and smell of makeup and perfume intensified my climax a hundredfold. I pushed Carmel's sweet face into my groin as the last of my issue dribbled from the eye of my cock. She kissed my slowly deflating penis and my tender thighs. She slid my lipstick-stained penis back inside my panties and pulled down and straightened my skirt.

She smiled up at me; still on her knees. She closed my legs and arose and then fell on top of me. She kissed me and I pulled her close.

"Nice?" she smiled down at me and I nodded my assent.

"Now it's your turn," her smile turned into a grin.

"One last blowjob for old time's sake," she giggled.

I felt her erection through the layers of lingerie, and her skirt; I reached down and felt her hard appendage through the layers of silk, satin and nylon. It throbbed in my hand and Carmel smiled and pulled my face to hers.

Our legs intertwined and our stockings rasped as they come into contact. The feel of the gossamer garments brushing one and other was magnificently titillating. Carmel pulled me close and rolled over so I was on top of her. I kissed her and pushed my groin into hers; I felt her hard cock pressing against me. She lifted her groin to rub it on my body and I smiled. Now I was in control!

I lifted up her dress and bunched it around her waist; my skirt had already ridden up. I lowered my body to hers and our panty-clad members touched; hers fully erect, mine flaccid but still sensitive. I slid my stocking-clad legs along hers and I ground my pubis into hers. She sucked on my tongue and hissed as she felt our satin-clad flesh rub together and our nyloned legs entwined.

I waned to feel and taste her in my mouth but the feel of our lingerie-clad bodies rubbing against one and other was exquisite and I didn't want to stop. Neither did she.

"Oh Michele; you are so beautiful! Mmmmmm I love what you are doing to me! Please didn't stop!" she begged.

We caressed, fondled and groped each other for what seemed like an eternity. My hand found her member and it was long, thick, hot and heavy. Her cock was so large that the head was poking above the waistband of her panties. I stroked the satin-sheathed shaft before my fingers explored the pulsing purple head; the eye sticky with pre-seminal fluid.

Report Story

byMicheleNylons© 2 comments/ 30294 views/ 12 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: