he word gets around that my newest girl is available to all customers."
"I expect you’ll be very busy indeed," Eddie’s laughter faded as he disappeared down the corridor between the cells.
I cringed at the thought of another night in this caged prison brothel, forced to service some of the roughest men I had ever met. At the same time I was feeling confused as to how quickly I had acquired female mannerisms; how I had become aroused by wearing the lingerie, makeup, wigs, and heels that Eddie forced me to wear. I was also amazed at how, after only a brief introduction, I was developing the skills of the feminine art in applying makeup.
I was more disturbed however, by how I had responded to the sexual attentions of some of the punters and the ministrations of my crossdressed sisters. I could not deny that, despite the fact that during this torrid night I had been repeatedly orally and anally raped, I had experienced two of the most intense orgasms of my life this evening. I decided that I was just too dog-tired to think about it; I needed to sleep. I was even too tired to be angry with Charlotte and Carmel, who although they had obviously enjoyed the sexual encounter we had just experienced together, had obviously been put up to it by Eddie so that he could enjoy the ‘all girl’ show.
The two vixens in question, (who had just introduced me to my first transvestite lesbian experience), slunk out of my workroom cell. They both glanced back and blew me a kiss.
"Nightie-night sweetie," they giggled in chorus, the sound of their laughter and the clattering of their high heels diminishing as they moved on down the corridor.
Mabel came in and dumped my prison fatigues on the bed and pointed to the door with the words,
"Out! Shower. Get changed!"
I got the message and slipped out of my feminine attire and deposited it in the laundry bin in the corner of the cell. My heels and breast-forms went inside the large wardrobe. I removed my wig and put it on a vacant wig-stand then took the towel Mabel proffered, cinched it around my waist, and headed once again down the passageway between the cells carrying my fatigues to the shower block.
The overhead lights suddenly clattered on revealing the workroom cells on either side of the passageway. Through the open bars I stared at the oversized double beds, rumpled satin sheets, large armoires and dressers with makeup mirrors, totally incongruous in this disused prison wing. The workroom cells were like islands of perfumed femininity amid a sea of stink created by caged men.
Mabel poked her head out of my cell and barked orders to a couple of prisoners who I recognised as weaker individuals who had ‘no muscle’ and therefore had shitty jobs working in the prison laundry. They were stripping the beds and dumping sheets and pillowcases into large wheeled washing carts. They were also emptying the laundry bins from each cell into individual oversized prison laundry bags; I noticed the laundry bags were each labelled with the cell numbers and the feminine names of the ‘working girl’ that used each cell. As I passed one of the laundry hands I saw him bring a pair of soiled panties to his face and rub the bulge in the front of his denim jeans. I scurried past disgusted.
The laundry was a big money maker for the prison. It catered for the needs of the prisoners, the guards, and also took in work from nearby hotels and a hospital. Eddie controlled the prison laundry, as he did just about everything in Chelmsford prison. Obviously also had the laundry workers working overnight to wash and dry the bedclothes and clothing that belonged to his ‘working girls’. To make his prison prostitution operation work he must also have the laundry dry cleaning service clean the ‘girls’ skirts, blouses, jackets and other items of clothing.
The cleaning of feminine clothing had to be being done overnight as I had made many trips to the prison laundry during the day whilst working as Eddies accountant and I had never seen any items of female attire in there. I knew Eddie made a considerable amount of money from the laundry; and of course, he was paying off someone high in the prison authority so that he could run the laundry business. As his accountant I knew he would also be charging the ‘girls’ for the laundry service; Eddie made money off everything, he gave nothing away.
When I got to the shower block I ran the water as hot as I could get it and soaked myself for half an hour in the shower trying to wash away the shame and humiliation of the last few hours. I scrubbed my face repeatedly to remove the caked on makeup. The blush, lipstick and eye shadow came off easily but I had to scrub at my face continually with the washcloth until it came away bearing no traces of foundation or mascara. I poured nail polish remover onto a cloth and cleaned the red nail polish from my fingernails.
I moved to the mirror and was glad to see that I looked like a man again; but then I noticed that some mascara was still clumped here and there on my eyelashes and little clots of eyeliner were smudged in the corners of my eyes. I picked up a bottle of moisturising cleanser from the shelf under the sink and removed the last traces of ‘Michele’ from my body.
I winced as I pulled on my denim prison uniform fatigues and felt the scratch of stiff cotton on my body instead of the luxurious feel of satin, silk and nylon. ‘Stop it!’ I told myself as I found myself wishing I could exchange the scratchy denim and cotton work-wear for the soft feel of feminine garments; ‘this is how you are supposed to be dressed Mike; as a man!’
I made my way back to my accommodation cellblock without further incident. I was amazed to find my cell unlocked and unguarded. Fucking Eddie ran the whole prison I was sure if it! I let myself into the relative privacy of my own cell. With only a peephole in the door for the guard to look through instead of the open bars of the workroom cells in E Block it was as private as one could get in prison. As my head hit the pillow my mind was spinning with what had happened to me, how drastically my life had changed in one day. The last thing I noticed through teary eyes before I fell into a deep sleep was the clock on the wall ticking over to 2:30am.
I awoke the next morning and looked straight at the clock; it was 9:30am. Eddie must have arranged it with the guard on my wing to let me sleep in. I was tired and sore from the events of the previous evening and the early hours of this morning, I just couldn’t believe what had happened to me. I seemed normal enough (or as normal as one could be when you are a guest in Chelmsford prison); just Mike. Mike brushing his teeth, Mike combing his hair, Mike changing into clean fatigues. Mike drinking coffee alone in the deserted cafeteria. There was no sign of Michele or her feminine ways; Christ I wished it were all just a bad dream!
I looked down at my hands holding the coffee cup and noticed that there were little crescents of red nail polish under the cuticles of some of my fingernails. "Fuck!!!" I exclaimed. Then I heard the voice I feared most; Eddie had snuck up on me and whispered in my ear,
"Come on Secretary you’ve got a lot of work to do. Just because I’ve found you some after-hours employment, doesn’t mean you can neglect your day job," he snickered.
I followed him and took up my usual post working on Eddie’s books as I had done every day for the last few months. I couldn’t bear to bring up with him the events of last night or even look him in the eye. What I did do though was to pay particular attention to those parts of Eddie’s business that had now come to directly effect me. Because Mabel ran the books relating to the prostitution ring, I had never really paid them too much attention before, except to check the bottom line for profit against loss; today I paid them special attention.
how Eddie’s prison business works and how Mike/Michele ended up becoming Eddie’s accountant and ‘secretary’.
A note for those of you who haven’t read Part I of this story; you probably need to read it now to understand
It was all there, the amount each punter paid Mabel for a ‘session’ with each ‘girl’ (there were various codes that I didn’t really understand but as some sessions cost more than others, I could only deduce those punters wanted ‘special services’ and paid accordingly). Here was listed the earnings made by each of Eddie’s transvestite hookers against the costs involved in running his secret prison brothel. Payments were listed to Mabel, the guards (although a lot of the guards seemed to take their payment in ‘trade’), and the inmate ‘minders’ Eddie employed (I shuddered as I though about how ‘Iron-bar Steve’, his most vicious minder, had used me).
The costs of female attire, lingerie, cosmetics, perfumes, wigs, shoes and other accessories were carefully recorded against each girl’s name and deducted from her earnings. It appeared that despite these costs, and even after Eddie had taken the larger part of the profit for himself, the girls still made a substantial amount of money. By prison terms they were rich; in fact they probably made more money than your average streetwalker did on the outside.
Then I looked up the ledger entries Mabel had made against me, ‘Michele’; I was astounded at how much money Eddie had made from me last night, even though only a couple of my ‘tricks’ were paying customers. Then I looked in the debit column at how much money I owed Eddie; I was flabbergasted. I owed him thousands of dollars for the clothing and accessories he had purchased for me!
"What the fuck Eddie?" I turned around and shook the ledger book at him.
"This is bullshit! I’m a rich man outside but it will cost me double the money I owe you in bribes to have that much smuggled in!"
"I suppose I have no fucking choice, It would take me weeks to pay this off earning the money you expect me to make in your filthy whorehouse!"
I couldn’t believe that in my outrage I was shouting at Eddie like this.
"Oh no Secretary bird; months at least; probably a year to clear that debt!" he laughed.
"What the fuck?" I stammered.
Eddie reached out and grabbed my slender throat,
"You can only pay for the goods and services I provide for you with the services you provide to me!"
"What the fuck does that mean?" I asked. "Why can’t I just pay you out from money I have on the outside?"
"All of your clothes, makeup, wigs, nylons and those nice frilly things I have you wear, you have to pay for out of the money you make in the workroom. That’s the deal. How do you think I keep my little harem working for me?" he responded.
"And of course you will always need more of those lovely things, because, as you can imagine, they tend to get worn out quickly and suffer more than their fair share of wear and tear during the working day; or should I say working evening," he laughed.
"And I can’t have my punters complaining that my girls dress like shit now can I?" he mocked.
"Besides; look on the bright side, you get to keep everything you pay for and I’ll let you keep any tips; pardon the pun," he laughed.
"In a few weeks, once you get to like the work, you will be asking for more and more clothing, lingerie, and girly luxuries, all my girls do," he finished.
"Girls?" I stammered.
"Girls! Girls! Fucking GIRLS!!!!!"
"They’re crossdressers you dolt! They’re men! Men! MEN!!!"
"And so the fuck am I! I’m a fucking MAN not a GIRL!!!!!"
Whack! Everything went black.
I woke up on my bunk in my cell my head throbbing.
"Christ!" I groaned.
Eddie had obviously belted me during my outburst and knocked me out. I raised myself off my bunk and looked in the mirror. No visible damage done; just a bump on the back of my head. Eddie was too smart to mark his latest money-spinner.
I noticed my cell door was closed and on further inspection locked. Then I noticed a suit-bag hanging on the end of the double-bunk. On the disused top-bunk was a pair of black high-heeled open toe sandals, a makeup case, a pair of expensive Italian pantyhose still in their wrapping and some boxes that when opened contained white satin lingerie. A wig composed of a shiny black bob, with discrete cerise highlights was perched on a wig-stand. I recognised it as one of the wigs Carmel had had me wear last night. The wig had been cleaned, combed and styled; the harsh prison light bulb picked up the highlights in the hair.
I walked over to the suit-bag and noticed a note pinned to it. It read:
‘Get dressed. Be ready by 1pm and make sure you look good for a special friend of mine. Steve will pick you up.
Or don’t get dressed, your choice!
If you’re not dressed when Steve gets there you won’t need to get dressed in anything but hospital pyjamas for at least a month!
Love Eddie
XXX’
Resignation came crashing down on me yet again; I would not be able to get out of Eddie’s clutches until I was released from Chelmsford…or… a glimmer of hope formed in my mind…transferred!!! That was it! I would get a transfer! I had plenty of money outside; sure it cost me double every time I tried to get any of my money smuggled in, but if Eddie could bribe the guards, surely I could too! All I needed to do was to find out the right person to bribe. I made a resolution right there and then. I would withstand whatever depravity I had to until I could arrange a transfer to another prison. With this resolve firmly in my mind I started to get dressed into the clothing that had been bought into my cell whilst I was unconscious (probably delivered by Mabel in her male alter ego: the washed up trustee lifer).
I shucked out of my prison fatigues and stood naked in the centre of my cell. Short, slim and well proportioned with all of my body hair removed my body did not look especially feminine; but it was more womanly compared to most of the inmates in here who were either bodybuilders or had resigned themselves to lives of flabby inactivity. Maybe I could fatten myself up so that I wouldn’t be attractive to men? Then I remembered Charlotte, the chubby whore from last night, being fat had not worked for her, it had just made her more attractive to men who liked larger women (BBW’s as they were referred to in men’s magazines).
I opened the large makeup case and investigated the contents. It contained plenty of makeup, a small bottle of perfume and some jewellery in the upper compartment tray. I removed the upper tray to discover that in the bottom compartment was a pair of breastforms. The two silicone tits looked forlornly up at me from the bottom of the case. Breastforms! This time yesterday I wouldn’t have had a clue that the fucking things even existed. I selected the ruby red nail polish out of the makeup case and sat down on my bunk and painted my toe and fingernails contemplating the future. Eddie obviously had a special trick lined up for me this afternoon; what he didn’t know was the trick I was going to play on him; if I could just find out who I needed to bribe to get out of this nightmare.
I laid out the makeup on the shelf in front of the mirror over the sink and started the transformation from Mike to Michele.
I applied a layer of heavy foundation from my hairline all the way down to the bottom of my neck. Next I applied a second layer of Revlon foundation that matched my natural skin tone and then set the foundation with a lighter shade of face powder. I rouged my cheeks to highlight my sharp cheekbones, applied another light dusting of powder, and then went to work on my eyes.
My eyebrows were thin anyway and just required a light touch of pencil to form the arches. I applied a pinkish hued eye shadow to my eyelids and then blended a light aqua from there to just under my eyebrows. With a fine brush I applied black eyeliner in a thin line on my eyelids as close to my eyelashes as possible, top and bottom. I took the line right into the corners of my eyes as I had been taught. I applied lashings of black mascara to my eyelashes, only having to clean up a few little flecks that dropped onto my face. Next, three coats of the same plum coloured lipstick that I had worn last night, carefully applied inside the matching lip-liner. I pulled the black bob onto my head and adjusted the wig so that it sat correctly. I clipped a pair of silver and diamond encrusted sapphire drops to my ears and a matching pendant around my neck to finish the effect. I looked gorgeous; Carmel would have been proud of my efforts I thought to myself.
Now, to the foundation garments! I unwrapped the expensive looking Italian pantyhose. The diaphanous sheer black nylons were fully fashioned with dark reinforced cuban heels and toes; a neat black seam ran up the back of the legs to the top of the waistband. The gusset was as sheer as the rest of the hose with no joining seams or cotton insert that is usually found in the crotch area of most pantyhose. The nylons were decorated with tiny little rhinestones just above the heels.
I sat on the edge of the bottom bunk and slipped on the sensuous hose being careful not to snag them. My legs looked stunning, the little rhinestones made the pattern on the outside of each of my calves, the cuban heels tapered into the back-seam. I adjusted the seams to run perfectly centred up the backs of my legs. As I smoothed the hose little sparks of delight flew up my legs and I felt myself begin to stiffen. Before I could become further aroused I pushed my penis between my legs and held it there with the tight nylon gusset. These hose must be really expensive I mused.
Next I slid the white satin panties up my legs sending more little darts of pleasure into my body as they rubbed on the nylons. I stood and pulled the panties into place around my bottom and crotch. They were pure white, sleek and discretely laced around the waistband and leg openings. The full cut white panties stood out dramatically against the black nylon pantyhose; the seat of the full-cut panties encased the globes of my buttocks perfectly and the front panel was tight against my crotch with just my little package spoiling the effect.
I removed the breastforms from the makeup case and stood before the mirror and put them in place. I had applied a liberal amount of artist’s gum to my chest and the back of the breastforms as directed by the label on the tube I had found in the case. The directions on the gum promised to hold them in place ‘for hours on end’; they certainly felt secure. I just hoped the fucking things weren’t glued there permanently.
I put on the white satin bra next. Still a novice, this proved to be the hardest garment to get into. In the end I clipped the catches at the back of the bra together and pulled it on like you would a T-shirt, arms in first then pulled the back strap over my head. I wrestled the garment into position and smoothed out the sleek satin cups over my false breasts and untangled the straps over my shoulders and around my back. It was a lovely fit, perfectly matching the satin panties with a lace trim along the top of the breastcups with a single pale pink satin rose nestled between them.
The last item of lingerie in the packages was a full slip of the sheerest translucent white nylon. I slipped the item over my head and pulled it down so that the bodice fit snugly against my torso; the slip flared at the waist and finished mid thigh. The hem was trimmed with lace matching my bra and panties. The gossamer thin garment felt luxurious and when the material stroked against my nyloned thighs little explosions of pleasure ran up my legs.
I stepped into the patent leather black high-heeled sandals, my painted toenails visible through the reinforced toes of my stockings, the pretty cuban heels accented by the ankle straps of the shoes. I bent down and fastened a silver anklet around my left ankle; the chain sparkling as the light reflected off it accentuating the miniature rhinestones on my sleek hosed calves.
I stood up and unzipped the suit-bag. Inside was a navy blue suit and sheer white nylon blouse. I slipped into the blouse, the cool feel of the nylon sleeves sliding up my arms, the light material whispering against the full slip as I buttoned the garment. I stepped into the skirt; it was snug at the waist and tight around my hips and bottom, the hem coming to just above my knees. I pulled on the wide lapelled jacket and my transformation was complete.
I looked in the mirror stepping back so I could see as much of my reflection as possible. I was no longer Mike, the weak willed accountant; I was Michele, a power dressed executive; a ‘fem fatale’ in a business suit. I sprayed liberal amounts of perfume on my neck, behind my ears and then as Carmel had showed me, under my skirt.
I was about to sit down when my cell door slammed open. ‘Iron Bar’ Steve stood there in the company of one of the guards.
"Oh fuck me Steve she’s fucking gorgeous; I’d love to shag her bent over the bunk dressed just like that!" the dimwitted guard exclaimed.
"Fuck off stupid, you couldn’t afford a fucking hand job off her, she’s out of your league," Steve responded.
‘How chivalrous,’ I thought to myself, ‘A brain-dead thug defending the honour of a crossdressed inmate prostitute to a corrupt prison guard!’ I couldn’t help but smile at the irony of the situation.
"Oh you won’t be smiling for long honey," laughed Steve, "Eddie’s special friend doesn’t like jokes from fag inmates one little bit."
"Who are you calling a fag Stevie? You couldn’t get enough of me last night could you?" I clipped sarcastically.
Steve raised his hand but I stood defiantly in the doorway of the cell. I knew that Steve dare not touch me at the moment as I was all prettied up for some special punter. It was good to actually feel a slight empowerment for once. I sashayed though the cell door deliberately taunting Steve but I paid the price as I passed him; he reached out and squeezed my pantied buttocks through my skirt.
"Don’t touch the merchandise Steve," I taunted again, turning my pretty face to his and pouting at him.
"Oh don’t worry Michele, I’m just here to escort you to your special date, but you will be well used merchandise when you return," he laughed.
I looked around the cellblock and noticed it was empty. All of the prisoners were at work of course, but I couldn’t see any guards either, other than the dimwit who had unlocked my cell and was now making his way back to the guard’s office at the end of the block.
"Oh don’t worry honey, you’re getting the red carpet treatment, no one is going to see where your going except for a select few in the know," Steve said, tapping the side of nose..
Steve led me through a series of doors and deserted corridors. I never saw another soul; the doors opened electronically when Steve swiped a keycard though each of the card reading devices fitted next to the door-locks. ‘Who the fuck is Eddie’s special friend?’ I thought, ‘He must have some clout to be able have a crossdressed prisoner led halfway through the jail without anyone seeing it happening.’ ‘And who the fuck gives prisoners like this maniac escorting me the keys to the jail; this was just fucking insane!’
We finally arrived at a set of fire stairs, the door to which Steve opened with a swipe of his card. He led me up three flights of stairs, me tottering on the high-heels I was still unaccustomed to wearing. He opened the door at the top of the last flight and held me back as he scanned the corridor for a few seconds.
"Ok, quickly now," he said grabbing my wrist and pulling me into the corridor behind him.
"This is his private entrance; I’ll pick you up from here in hour. Behave ok!" Steve whispered in my ear, kissed me gently on the earlobe, and pushed me through an unlocked wood paneled door and slammed it shut behind me.
I half fell through the door and as I glanced up I could just make out the name embossed on the door; in faded gold leaf lettering it said WARDEN.
Warden Stone was a large man and as I fell though the door he caught me in his strong arms.
"You must be Michele," he smiled, gazing directly into my eyes.
"Here take a seat," he insisted leading me to a large leather divan set against one wall of the large office.
I was mesmerised; I knew that things were obviously way out of the ordinary in this fucked up jail. What with Eddie running every legal and illegal activity he could, including a lucrative brothel staffed by crossdressed feminised prisoners, corrupt guards and inmates running around with the keys to the doors; it was just farcical. The lunatics were literally running the asylum. But this! The Governor admitting a crossdressed prostitute, delivered by a messenger from the hardest criminal in the jail, into his private office; this was beyond comprehension!
But then again; in some fucked up way it made sense. How could Eddie possibly get away with what he did in here without the blessing of the Governor. In fact it made even more sense as I quickly caught on to the enormity of the situation; this was where Eddie’s largest payments went to; the Warden, they were obviously partners. The Warden ran the jail but Eddie ran everything inside the jail and the Governor got his cut; including the fringe benefit of access to Eddie’s working girls whenever he wanted. How else could all this be explained?
At the same instant another lightning bolt struck me; I was now with most powerful man in Chelmsford prison, if anyone could get me a transfer out of here it was him! I decided right then and there that I was going to be very nice to the Governor; no matter how disgusting his needs were, I was going to tend to every one of them willingly. After all, this could be my only shot at getting out of this nightmare. ‘So Mr Stone,’ I thought to myself ‘You’re about to have the wickedest hour you ever spent with one of Eddie’s whores!’ I mustered my resolve and made my move.
"Why thank you Warden Stone," I offered him by biggest smile and sat down, crossing my legs in a ladylike fashion so that the hem of my skirt rode up to mid thigh.
I noticed his eyes open wide and heard a sharp intake of breath as he heard the soft rasp of my nylons rubbing together and stared at my thighs encased in their gauzy nylon sheaths.
"Stanley please," he smiled back.
"And you are Michele I’m told," he went on.
"Well Michele let me paint a picture for you; I’m sure you are not naïve and understand why you are here. But there is no need for this to be unpleasant for you; I assure you that I can behave like a gentleman, and this scant hour we have together can be a welcome break for you from the filth and depravity you experience very day in my prison."
"So Michele, shall we spend a nice relaxing hour together?" he asked expectantly.
"Why Warden, I mean Stanley; if you are the gentlemen you already appear to be I’m sure I can behave like the lady you want me to be. Perhaps we can even accommodate each other in other ways if you would like to discuss a proposal I have for you?" I responded maintaining my painted smile.
Warden Stone’s face clouded over at my proposal; I had gone too far too early; I went into damage control.
"But of course that’s for later, please sit with me," I patted the leather couch next to me and batted my lashes like a good little coquette.
Stanley smiled again and managed to drag his gaze away from my legs to my eyes.
"Lovely, but please, allow me to get you a drink; scotch?"
"Please," I smiled back and he turned to an expensive looking oak cabinet to pour the drinks.
‘I might as well make the most of this,’ I though to myself as I glanced around the Warden’s impressive office. As one would expect it held all the trappings of power; a large desk, chunky furniture, the wall adorned with certificates, trophies and pictures of the Warden with other powerful men. On his desk I noticed a picture of the Warden and his family. His wife appeared mousy and his daughter was a skinny teenager with dank hair; they were smiling painfully for a picture obviously posed to project family harmony. I wondered what his mousy wife would think if she knew that Stanley’s peccadilloes ran to intimate encounters with crossdressed prison inmates?
Stanley returned to the large sofa, stopping off to turn out the overhead lights and check that the door to his outer office was locked and the shades lowered. He set the drinks down on side table and adjusted the one remaining lamp to a diffused glow. ‘Very cosy,’ I thought to myself; ‘I bet his receptionist is on an errand for an hour or so.’ I wondered how often he did this?
The Warden handed me my drink and indicated the vacant place beside me on the sofa,
"May I Michele?" he asked smiling.
"Of course Stanley," I smiled, again patting the seat beside me.
Stanley sat down heavily beside me and the cushion gave way under his weight so that I leant in towards him slightly, the golden liquid and my red fingernails glimmered in the diffused lamplight as I raised my glass to him.
"Cheers," I whispered and drank heavily from my glass.
"Cheers," he responded, downing the spirit in one huge gulp.
Stanley had to be over a hundred and thirty kilos and close to two meters tall; well proportioned but large; I noticed the beginnings of a paunch hanging over his belt as his suit jacket opened. ‘Ok this is it,’ I decided; ‘lets get this façade over with!’
I reached out and took his empty glass from him and placed it on the side table beside mine, a crescent of lipstick decorated the rim of my glass.
I turned to face the Warden and reached out to him, gently taking his head in my hands, I pulled his face towards mine seductively opening my lips slightly. Stanley groaned and pressed his lips lightly against mine. He kissed me softly, with his mouth closed; then he reached out and put his strong arms around me and eased me against him as he smothered my face with feather soft kisses. He kissed me all over my face; my lips, my cheeks, my forehead, and placed little butterfly kisses on my lightly closed eyelids.
"You are so beautiful," he whispered in my ear, gently nuzzling my earlobe.
My hands were now on his powerful shoulders and we embraced each other for a few minutes; softly kissing each other, I felt the heat slowly growing in him as he became aroused.
I felt his hand slide down my body and come to rest on my knee; he softly massaged my leg, slowly working his hand higher, lightly stroking the inside of my stockinged thigh. His breath was becoming heavy now but he made no attempt to force himself on me; his mouth remained closed as he tenderly rained down soft kisses on my mouth and face.
I reached out with one hand and placed it on his thigh feeling the hard muscle through the material of his trousers; the back of my hand brushed briefly against his tumescent member; he gasped.
"Oh Michele; you naughty girl!" he whispered, his hand sliding under my skirt came into contact with my slip.
The Warden wrapped his hand in the silken material and began to slowly glide the slip up and down my thigh. The feeling of the delicate fabric rubbing on my pantyhose was exquisite; my member began to awaken in the silken gusset of my hose; my tight white panties holding it in place as it slowly thickened and elongated.
I moved my hand across the bulge growing in the Warden’s trousers and found the zipper on his fly. He removed his hand from under my skirt and gently moved my hand away.
"No Michele, I want to taste all of your sweet treasures before we consummate our little interlude," he said and took hold of my upper arms in a tight grip.
‘Quite the wordsmith,’ I though to myself; ‘I wonder what sweet treasures he intends to enjoy?’
Stanley kissed me fully on the lips, pressing his torso hard against me, slowly sliding his tongue into my mouth; I tasted my own lipstick on his tongue as he gently explored my mouth. Then he pulled his face away from mine and eased me back against the padded armrest of the divan. I guessed that now he would want more than just kisses and caresses and as he adjusted his position on the sofa I made to remove my suit jacket.
"Oh please no Michele; I want you dressed just as you are. I love a woman who can pull off the whole power-dress performance thing and still look feminine and sexy."
"Do you like the lingerie? I had Eddie acquire it for you just for this occasion; and those nylons, God, I could eat you up in those. In fact I think I just might," he chuckled.
I relaxed back against the padded armrest and Stanley bent down and lifted my legs so that I was lying lengthways on the divan. I was lying with my back supported by the padded armrest and my legs across Stanley’s lap.
"That’s better," he smiled and began to stroke my legs with his hands.
"Oh that feels so sensuous, and I just love those little rhinestones sprinkled on your stockings," he said.
He bent his head and raised one of my legs to his mouth and commenced planting sweet little kisses all up and down my calf. He moved his lips slowly up and down my lower limb and then licked the back seam of my stocking all the way down to my high-heeled sandal. He kissed my feet, and pushed his tongue into the darker reinforced extremity of my hose and sucked on my painted toes through my open toe sandals. I must say it felt quite erotic.
Stanley used his free hand to stroke my other leg sliding his fingers far up under my skirt, stroking up and down my leg slowly and sensuously.
"Mmmmm let me see," he groaned and lifted his face from my feet.
He opened my legs slightly and raised my skirt up around my waist. He gazed upon me lying there with my stockinged legs in his lap with the hem of my slip coming halfway down my thighs, the pure white nylon slip in contrast with the dark hosiery.
"Lovely," he said, and began to kiss me up and down my legs again.
This time he buried his head under my slip and continued up my legs right to the top of my thighs. He kissed the front panel of my satin panties whilst stroking my legs. After a minute or so of placing soft kisses on my panties and thighs he made his way back down my legs and began to suck on my nylon sheathed toes again. His hands were now sliding the soft material of my slip up and down my thighs creating wonderful sensations through my body. My member was stiffening further and was becoming uncomfortable being held in place under my crotch by my pantyhose and tight panties.
Stanley was now licking my shiny black patent leather sandals, holding both my feet in place by the spikes of my heels. As he worshipped my feet and gazed up my legs, his eyes glazed over with lust; then he started sucking on the spiky high-heels, taking them into his mouth and lovingly caressing them with his tongue; first one then the other; as if fellating my heels.
He was panting and groaning as he worshipped my legs and feet. Then he moved one hand down to his fly and pulled on the zipper. His hand disappeared inside and rummaged around eventually freeing his erection; it protruded stiffly from his trousers, red, angry and engorged.
Stanley lifted my feet and re-positioned them one on either side of his hard cock and slowly started to fuck my feet. I realised what he was doing and assisted him. I slowly started to masturbate him with my feet, slowly lifting them up and down, letting my soft stocking foot caress the head of his penis and then the patent leather of my shoes.
Stanley threw his head back against the cushioned divan and let me foot fuck him. He renewed his carnal attack on my legs as I wanked him with my feet. I trapped his member my feet and stroked hard. He moaned and writhed in ecstasy.
Then he looked at me again and gently moved my feet out of his crotch. He stood up and re-positioned himself on the divan so that he was kneeling between my spread legs. With trepidation I thought, ‘Here he goes; he’s going to fuck me.’ But he didn’t. Stanley closed my legs and lifted my feet up to his mouth and began to worship them with his lips and tongue again. I was lying down full length on the divan now with just my head pillowed on the armrest, my skirt and slip rucked up around my waist with my legs lifted up whilst Stanley took oral pleasure on my feet and calves. Now I knew what ‘sweet treasures’ the Warden wanted to taste; he was a foot fetish. ‘Well at least I might leave here without having to gratify him in some other disgusting way,’ I thought to myself.
Stanley was now in a frenzy, lapping and sucking at my shoes, toes, and feet; he was panting, his face red and sweating. Stanley actually looked quite pathetic dressed in his full suit with just his stiff penis poking out his trousers as he paid homage to my peds. He stopped briefly and quickly fumbled at his waist, undoing his belt and pushing his pants down around his thighs. Then he gripped my ankles, lowered my legs and pushed my feet together. He pulled my feet between his legs so that his cock lay in the silken valley created by my calves. Then he started to fuck my legs.
He rubbed against me faster and faster and I could feel the friction of his hard cock against my nylons. Stanley groaned and whimpered. His gaze alternated between my face and my pantied crotch as he pushed his cock against me harder and faster.
I decided that I would assist him with his fantasy and placed two slender, red-nailed fingers on the gusset of my pure white satin panties and began to stroke. Stanley reacted immediately.
"Oh yes Michele! You naughty, naughty girl!"
"You are such a pretty girl, but such a naughty girl," he chanted.
"Oh Michele, you naughty nyloned princess I’m going to come; I’m going to come all over your pretty toes and feet; would you like that?" he begged.
"Yes Stanley please; please come all over me!" I role-played for him as he approached his climax.
He shifted his grip to my ankles again and pulled my feet up to his quivering member. I knew exactly what he wanted and began to masturbate him hard and fast between my feet; pushing back and forth with my legs so that my high-heels and stockinged feet ran up and down the length of his shaft. At the same time I furiously rubbed the front of my panties; a parody of a woman pleasuring herself.
"Come for me Stanley; come on honey, come for Michele baby," I cooed.
Stanley’s face screwed up and went bright red as a shattering orgasm washed over him. Ropes of creamy semen jetted from his penis splashing up my legs. Spatters of his spend formed sticky white pools on my calves and feet; they glistened in stark contrast on my black stockings. My diaphanous black hose became darker still in the places where Stanley’s semen soaked into the nylon.
A silvery thread of Stanley’s ejaculate hung down from the heel of one my shoes forming a sticky necklace between my foot and his deflating penis.
"Oh Michele, that was wonderful," Stanley gasped and collapsed on top of me.
His weight nearly knocked the breath out of me as he started to cover me my face with soft kisses again. I pushed lightly against him until he took the hint and rolled off me so we were lying side by side. Stanley pulled me close against him, one arm over my body caressing my buttocks, slowly stroking the sheer nylon slip against my panties. His kisses grew harder and his tongue now invaded my mouth; I could hardly breath. I managed to pull my face away from his.
"I’m glad you liked that Stanley; was that how you wanted to take me?" I whispered in his ear.
"Oh yes Michele, but that was just an entrée sweetheart; I recover very quickly," he whispered back.
"Perhaps a drink Stanley, before we play some more?" I asked.
I was getting confident now; the Warden was obviously a submissive, I had read that powerful men often liked to take on a submissive role during sex play. I decided to test my theory.
"Come on Stanley, pour me another scotch and we can discuss a proposal I have for you. If you are a good boy and treat me nice I might let you have some more," I teased.
I was not prepared for what happened next; I had hopelessly misjudged the situation.
The Warden used his powerful build to roll me onto my back and pull himself up so he straddled my waist. One huge hand came across and swiped me on the side of my face, stinging and numbing me.
"Oh I don’t think you realise the situation here bitch! I’m the fucking Warden of this jail and you’re just another slag who Eddie provided for me to use as I see fit."
"Don’t try and offer me proposals! I make the fucking proposals here!" he screamed at me.
"Now here’s a fucking proposal; lift your fucking trollop arse up off my lounge," he yelled.
Warden Stone stood up and dragged me off the divan and shook me like a rag doll. I was terrified; the man had turned from being a gentleman to a demon in the space of seconds.
"Here’s another fucking proposal," he barked and shoved me hard towards his desk.
I tottered on my heels and reeled over towards the desk; one of my shoes flew off and my stockinged foot slid on the polished floor. I reached out trying to grab the desk for support but I collapsed on the floor beside the desk, legs akimbo.
"And here’s my final proposal," the Warden bellowed and moved in, pulling me up off the floor and bending me over the huge oak desk.
One bear-like hand grabbed my skirt and tore it from my body; the side seam splitting with a loud rip. The Warden pushed me down harder on the desk, he put one hand on the back of my neck and mashed my painted face onto the hard surface of the desk. With his free hand he pulled my slip up and over my back and I realised how exposed I was in this position. I was bent over the desk with my skirt ripped off, my slip hiked up, tottering on one heel, my satin pantied buttocks raised and exposed.
Warden Stone let go of my neck briefly but it was no relief; I was horrified by what he did next. He put both hands on my hips and yanked my panties and pantyhose down in one swift movement. They tangled in a bunch at the top of my thighs.
"No! Please, Stanley don’t do this," I whimpered.
"What you mean this, you cocksucking whore," he taunted and I felt him position himself behind me, his swollen penis probing at my buttocks.
"No! No! Please!" I begged.
"Well what do you think of my proposal Michele?" he grunted and pushed forward with all his weight.
"Ohhhhhhh god no!" I moaned as his member slid all the way up inside me.
I felt as though I had been split open. It was so tight and he was in me so deep that I could feel his groin hard against my bottom. Then he raped me. He just fucked me like a whore. Bent over the desk I could offer no resistance as Warden Stone commenced thrusting in and out of me. I don’t know how long he ploughed himself into me; at least ten minutes; he obviously had plenty of staying power having just recovered from an orgasm only minutes ago.
He grunted and groaned, calling me filthy names and slapping my buttocks as he fucked me hard and fast. His cock pistoned in and out of me and his groin slammed against my buttocks. I forced myself to relax my sphincter but the pain was still excruciating. Eventually the lubrication from his pre-seminal fluid eased some of the pain as his invading member continued to rape me.
Eventually he bellowed, grunted and puffed and suddenly I felt the hot ooze of semen inside me. The Warden wasted no time and pulled himself out of me immediately. He yanked my panties and pantyhose up over my buttocks and I felt him wipe his penis clean on my buttock; his warm spend left a wet patch on the cheek of my bottom. I remained bent over the desk, silent and humiliated, feeling vile and debased as the Warden pulled up his pants and shoved the tails of his shirt into the waistband of his trousers.
There was a gentle rapping at the wood paneled door through which I had entered the office only an hour ago. The Warden grabbed my arm in a vice-like grip and dragged me across the office. He opened the door and threw me outside like a piece of garbage; I tripped and fell to my knees on the hard polished floor tearing my beautiful pantyhose. I looked up to see ‘Iron-bar’ Steve smirking down at me. The Warden briefly disappeared back inside his office, then returned to the doorway and threw my shoe and my ripped skirt at me.
"Tell Eddie I’ve finished with this for now. She’s one of his better whores, but she has too much of a mouth on her," Warden Stone barked at Steve and slammed the door shut.
ÂÂ
ÂÂ
ÂÂ
ÂÂ
