Shemale
2004-12-26
Lady in the House Part V
By
Michele Nylons
From Part IV
Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread there when he had pressed his body against me.
I watched the terrible storm brood in his eyes as he reached out and smashed me across the face.
"You dirty Cunt!!!" he screamed, and pushed my face into his belly.
"You lick that disgusting mess off my body before you lose some teeth!" he bellowed, rubbing my face against his belly as I made a vein attempt to lick my own spend off his stomach.
He pushed me back on the bed, my makeup ruined, mixed with semen and tears and smeared all over my face.
"Now get yourself cleaned up and get changed you filthy whore; you're open for business!!!"
Part V
Carmel rushed into the cell, or as she called it, my 'workroom';
"Come on Michele, the night's only just begun! The waiting room is full of punters, and because you are the new girl, you're top of the menu!" she said, busily fussing around me and helping me to my feet.
I allowed myself to be pulled up off the bed, and stood in front of Carmel (who until today I had only known as Craig).
"Look what he did to me!" I cried; "Look what that disgusting man did to me!"
"Oh shut the fuck up," Carmel crowed. "You'll get worse and you'll get better Michele; that's the life of a working girl here in Chelmsford!" the crossdressed freak standing in front of me explained matter of factly.
"That's just it!" I cried.
"I'm not a girl! I'm not Michele; my name is Mike and I'm a businessman not a woman! And you are not Carmel; some kind of bawdyhouse Madam; as you like to pretend! You're Craig! A guy in a dress, pretending to be a girl! You're just a sad, pathetic, transvestite prostitute living in some made up dream world inside this prison!"
"I'm a big name outside!" I cried.
"A 'Face'! As you jailhouse scum are want to say! I have money, friends, influence" I cried.
Carmel laughed out loud and slapped me hard across the face. I felt the sting though my tears.
"No honey! You have it all wrong! You're inside Chelmsford prison honey and you are whatever Eddie want's you to be!"
"You're Michele! You're Eddie's property; and you have about five minutes to get ready because customers are waiting!"
"Now pay attention, you really are on your own after I clean you up; a girl's got to make her own living too you know, I can't spend all night showing you how to put on makeup and how to dress" Carmel sneered.
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She led me back past the five other cells that made up this section of E block. Low light leaked through the bars of the other cells; red shaded bedside lamps had been lit. I saw other 'working girls'; transvestite prostitutes, putting the final touches to their makeup, adjusting the seams on their stockings, or arranging their wigs. They sat on their oversize cots that had been made up with satin sheets; bold colours, black, red, and blue were predominant. One or two of them looked up with their painted faces and smiled at me; but there was no sympathy in their smiles; they were the types of smile that predators gave their prey just before they pounced for the kill. Four of the cells were occupied by Eddie's 'girls', leaving my 'workroom' and the cell across the passageway vacant. It dawned on me as I clattered along on my impossibly high-heels that the vacant cell directly across from me must be Carmel's 'workroom'.
We arrived at the bathroom at the end of E block again and Carmel helped me undress and sat me down in front of the highly polished stainless steel mirror. I washed my face clean and stared at the makeup arranged on the shelf below the small sink.
Carmel said, "Ok Michele; you’ve done this enough times tonight with my help; it's time you went solo. "
Carmel lit a menthol cigarette and sat down on a stool beside me, preening herself in the mirror. She made minor adjustments to her own makeup as she sat there and smoked.
It was amazing how much I had learned in such a small amount of time. I took a damp sponge and applied generous amounts of foundation to my face and neck finishing with a slightly lighter coloured powder to set my face. I rouged my cheeks, eventually getting the hang of how to accent my high feminine cheekbones.
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Carmel had to instruct me again how to apply the rouge after my first attempt made me look like some kind of circus clown with rosy red cheeks. I then applied liberal amounts of eyeshadow, eyeliner, and mascara with minimal assistance from Carmel.
"You're getting the hang of it honey, although you do look like a bit of a panda, but you will become very good at it soon," said Carmel laughing at my efforts with the mascara applicator.
"Besides, the punters like us heavily made-up, it's not like were supposed to be their wives or Moms," She laughed wickedly and applied another coat of mascara to her own heavily made-up eyes.
I finished with another light dusting of powder and applied two coats of plum red lipstick to my pouty lips. Putting on the lipstick I had discovered, was the easiest part. I applied a touch-up coat of bright red nail polish to my toenails and fingernails where they had been chipped. I checked myself out in the mirror with a self-satisfied smirk. Not bad for my first solo effort I thought.
"Wonderful Michele; you are getting the hang of it now," Carmel cooed like I was a good pupil who had learned her lessons well.
Then I took stock of the situation. I had been concentrating on applying my makeup and was amazingly, feeling a shimmer of pride in my efforts! What the fuck was wrong with me! I had also referred to myself as 'SHE' in a number of my thoughts and more disturbingly had subconsciously thought of: 'MY makeup!' 'MY clothes!' and 'MY shoes!' What the fuck was happening to me! Was I turning into some kind of willing participant in this sick, fucked world that Eddie had created inside this prison!
I bought myself back to reality by concentrating on the debauchery I had suffered over the last couple of hours. I had been sodomised and orally raped; my back passage was still sore from Eddie's invading penis. I could still taste the swampy, salty, taste of 'Iron Bar' Steve's secretions which he had deposited in my unwilling mouth; and my ribs and stomach muscles still ached from the pummelling I had received from Eddie during the evening.
I looked in the mirror again and saw what I really was; a small, insignificant male prisoner forced to wear makeup and jewellery.
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A parody of a woman! A man compelled to dress up in women's clothes so that sick, twisted prisoners could take their carnal pleasures and somehow justify to themselves they were not gay because they took their gratification from a man who is dressed as a woman.
Carmel helped me into a satin robe and then scooped all of the makeup off the shelf and into a small makeup case. She took the wigs with their stands and loaded them into my arms she grabbed my discarded clothing and shoved it with my high-heels into my arms on top of the wigs. Holding the makeup case in one hand she took my hand and started to drag me out of the bathroom.
"Ok Michele, from now on this place is just for you to clean up, shower and shave. Don't leave any clothes, makeup or jewellery here or the other girls will nick it as soon as you take your eyes off it; and then you will have to pay for it to be replaced. "
"Everything you need is in your workroom and only you, Eddie, and Mabel have a key. "
"Who the fuck is Mabel?" I asked.
"She's an old lifer who likes to crossdress. She's really too old to shag, but some of the cons occasionally give her one when they are short of money. She's Eddie's minder for his stable of working girls. Steve is the muscle, and Mabel is the housemaid is the best way to explain it I suppose. "
"Mabel comes around during the day and changes the sheets and washes our clothes. She'll replace your makeup and tend to your wigs. She also takes orders for new clothes, lingerie, and any special costumes when you need them; all done for a small fee, and all done with a smile, she likes to be around us girls," Carmel beamed.
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"She also takes our bookings and manages the punters in the waiting room. "
"What the fuck are you talking about?" I asked Carmel, bemused.
"Look Michele I really don't have time for this; you used to be Eddie's bookkeeper so you should have it figured out by now. Half of every fee we get off a punter goes to Eddie ok. You will probably have to work for nothing for about three months to pay for the clothes and other stuff Eddie has bought you to get you started with. Once you start making money Eddie keeps it for you on a tab; Mabel will deduct your expenses and such and will also give you cash or goods when you need them. "
I realised what Carmel was explaining to me of course. As Eddie's prison accountant I had indeed managed his books and was aware that he had someone else look after his 'working girls' and put money into and out of that part of the account; but all I ever saw were the profits. It never occurred to me how complicated this side of his business was.
"Hang on a minute; what the fuck are you are talking about? Expenses? Goods?" I asked.
"Jesus Michele! You just don't get it do you?"
"Everything is a business to Eddie. The clothes, makeup, wigs and so forth you have to pay for. You also pay to have your clothes washed and 'workroom cleaned'.
You also pay when you order in more clothes, wigs, lingerie, shoes and stuff. Mabel will bring around the catalogue and an order form for you.
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"
I mind flew back to the times I spent with Eddie as he made me order in women's clothes, nylons, makeup and so forth for his stable of working girls; but I never thought I would be wearing any of it!
"Sometimes if Eddie sees something he really wants to have you wear he'll buy it for you as a present," she smiled.
We had arrived back at my cell; my workroom as it I now realised it to be. Carmel pushed me through the door.
"Ok hun, its ShowTime; put those dirty clothes in the laundry basket, put your wigs and makeup in the wardrobe and get dressed. Try that long black wig hun, it will suit your makeup. As you can see Mabel has laid out your outfit for your first customer, it must be a special request, that's always good because have to pay more. "
With that Carmel went through the door of her own cell, sat on the bed and lit another menthol. She punched a button on an intercom located on a nightstand next to her bed and spoke into it.
"Ok Mabel, send him in," she sang.
Carmel rushed across to my cell and pointed to an identical intercom on my bedside table.
"Oh, I forgot to tell you how this works. Its simple hun," she explained, "when the blue light is on you have a punter waiting. Press that button to talk to Mabel in the waiting room. Press that orange button to indicate you are busy, cleaning up whatever, and that red button there is the panic button. "
"Press the panic button and 'Iron-Bar' Steve will be here in seconds.
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But only press it if you have genuine emergency," she advised me, slipped me a wink, and skipped out of my cell to the sound of approaching footfalls.
Genuine emergency! GENUINE FUCKING EMERGENCY!!!!
What could be more of a genuine emergency than being forced into being a transvestite prostitute in a fucking jail!!!!
I sat on the bed and controlled the urge to cry. I knew it wouldn't help; all I could do was to get through tonight and then figure out a plan to get of the indescribable mess I was in.
I looked down at the clothes arranged on the black silky sheets. A 'special request' Carmel had said; what the fuck? Resignedly I started to dress.
First I open the package of hosiery. It contained a pair of white, sheer to the waist pantyhose. As I slid the sheer nylon up my legs those little electric sparks of delight again ran through me. I hated myself for enjoying the sensation of it! The sheer waistband was snug around my tummy and I tucked my deflated little penis between my legs to be held there by the gossamer nylon gusset of the pantyhose. Next I slid a pair white full brief satin panties up my legs and pulled them snug around my bum and groin. The rasp of the silky panty material against my sheer hose was so sensual that I felt my little cock pulse.
I slid the matching white satin bra around my chest and went to the drawer where I knew my breastforms where kept and placed them neatly into the bra cups. 'My breastforms'…………what the fuck had happened to me!
I concentrated on getting dressed and tried not to think about the exquisite feel of the nylon and satin on my skin. A pair of plain white high-heeled pumps was at the foot of the bed and I slid my feet into them and stood up. A single pristine white cotton tunic was laid out on the bed so I stepped into it and pulled it up my body.
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As I started to do up the buttons on the front of the tunic I realised what it was. A nurses uniform; 'Special Request' in-fucking-deed!!!
As recommended by Carmel, I placed the long, raven haired wig on my head, adjusting it in the mirror on the wardrobe door. I picked up the little white nurse's cap with the Red Cross on it and placed it on top of my head. I looked stunning!
In the full-length mirror was the image of gorgeous nurse in a crisp white tunic buttoned to her throat. Her long legs shimmered in gauzy white nylons below the knee-length hem of her skirt. Her legs terminated in the pristine white high-heeled pumps. The nurse lost all credibility however when you looked at her face. She was so heavily made up; with lashings of mascara and plump red full lips framed by her glossy black mane. The little white cap with its Red Cross added to the image; the girl in the mirror looked like a tramp in a nurses uniform; the same sort of fetish clothing worn by the girls in men's magazines that I liked to masturbate over.
I looked down at the bedside table and noticed the little blue light flashing. My trembling hand extended a red-painted manicured, finger-nail and pushed the button.
"Send him in," I whispered hoarsely.
Oh my God; what was I doing? The only thing I could I realised; do what I was told or have my legs and face broken. It was only for one night and soon it would be over. I would escape; I would tell the Warden, my lawyer; someone who could get me out of the obscene mess I was in!
I sat on the bed and waited.
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My eyes drifted to the cell across the way and I saw Carmel. She was standing up in her cell, bent over and holding on to bars of her cell for support; her painted red fingernails digging into the palm of her hand as she tightly gripped the iron bars. Her skirt was rucked up over her back, her pure white arse raised suppliantly into the air. Positioned behind her a large black man was pounding himself in and out of her. As he slammed into her he grunted and pulled her soft white arse back against him so he could drive himself in her as far as he could go. Carmel's heavily made-up face looked idyllic as she concentrated on maintaining the rhythm whilst she was anally pummelled. She open her eyes and looked at me through the bars, she smiled at me, winked and then closed her eyes again as she rocked back and forth on her high heels, her sheer stockinged legs glittering in the low red lamplight.
I head heavy footfalls approaching my cell and realised it was my first customer. I silently prayed.
A shadow fell across the doorway to my cell and the footfalls ceased. I looked up under the dark fringe of my hair; the heavy mascara and eyeshadow causing my eyes to reflect like two deep blue pools. My eyes met with a large man in his late forties. His thick arms heavily tattooed, burly chest and huge pot belly were barely contained by his faded blue singlet; faded denim jeans hung beneath his large belly and his shoes were prison issue boots, scuffed and poorly repaired.
I recognised him immediately; it was Harry Watson; or 'Doc' Watson as he was called by all who knew him. He was one of Eddie's 'enforcers'; a good mate of Iron-Bar Steve and just as ruthless.
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Harry stepped into the cell and held out his rough dirty hand to me. I took it in mine and stood up, shaking in fear with what was about to happen. Harry looked me over slowly with hungry eyes. He looked down at my white high-heeled pumps and followed my shapely; nylon encased legs to where they disappeared inside the hem of my nurse's tunic. The white pantyhose shimmered in the low scarlet light cast by the bedside lamp. His eyes continued up my crisp white uniform, resting for a few seconds on my large false breasts, straining the buttons of the tunic. He then continued his gaze up to my face, his eyes engorging themselves on my full plum-red lips, my heavily mascaraed eyes, my rouged cheekbones framed by the jet-black mane of my hair. Finally he looked at the little nurse's cap with its silly Red Cross perched on my head.
"Fuck, you are worth every penny I've paid; now the Doctor want's his nurse!" he groaned and pulled me to him.
His foul tongue thrust into my mouth as he crushed his lips against mine. He groaned and his hand went straight under my skirt and began to brutally squeeze my buttocks through the silky satin panties and sheer hose. Harry pulled me close and as his rancid breath panted into my mouth, I felt his rock hard penis pushing against me though the fabric of his jeans and my skirt. He pushed me away from him releasing his grip and looked me up and down again with wanton lust.
"Lift yer skirt!" he demanded.
"Whaaat?" I stammered, dazed and confused.
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Slap! Harry's hand snaked out and backhanded me across my cheek.
"Lift yer fucking skirt Nursey or I'll tear the fucking thing off you!" he shouted.
I looked down at his feet and took the hem of my pristine white cotton skirt in both hands and slowly raised it up my thighs. Harry's eyes followed the hem and opened wide as my firm thighs, encased in gossamer white nylon, slowly came into view. He gasped as the first glimpse of white satin panty was exposed and couldn't help him self; he reached out and stroked his hand up and down by thighs; his rough hand slithering over the gossamer nylon.
"Oh fuck, you're just what I asked for; I can't wait any longer Nursey or I'll come in me pants!"
With that he grabbed me roughly and spun me around so I was facing the bed.
He pushed down on my shoulders and I fell forward doubled over so I that was tottering on my heels with my weight supported by my outstretched hands on the bedside table. I heard a ripping sound that could only be the zipper of his fly being pulled down. Inside I screamed and prayed, hoping what I knew was coming next wouldn't happen.
I felt Harry lift my skirt up and push it over my back so that my silky arse was exposed and thrust up at him as I gripped the nightstand to keep my balance. Then I felt a hot iron bar pushed against my pantied ass it rubbed all over my satin encased buttocks. I realised it was Harry's erect penis. Then I felt his erection slide under the silken gusset of my panties and wedge itself in the crack of my arse.
Instinctively I tried to move forward and away from the invading member but Harry gripped my waist, cruelly digging his hands into me as he held me steady.
"Oh no you don't Nursey; hold still while the doctor tends to you," he hissed.
I could feel his hard cock rubbing against the thin gauzy nylon of my pantyhose as it pushed the silky material into the crevice of my arse crack. Then I felt Harry reposition his member so the head was nestled in the rosebud of my sphincter. Now the thin layer of pantyhose was the only protection between my anal canal and his hot throbbing cock. I felt harry pull the gusset of my panties across my buttocks so that he had an unobstructed view of his penis poised at my rear entrance; his erect member pushing the nylon of my pantyhose tight against my sphincter. He said one word.
"Lube!"
"Whaat?" I stammered again.
"Lube! Or you can take it dry, but I think you will appreciate some lube Nursey!"
I knew what he meant then, and although horrified I remembered the torture of Eddie's rampant member invading my unlubricated anus. I reached under the pillow with one hand and searched for the tube Carmel had put there previously this evening. I grasped it and thrust it out behind me, rocking precariously on my high-heels as I held onto the nightstand with only one hand.
"No, you do it Nursey," Harry laughed.
He took the tube of KY jelly and squeezed a big blob of the cool slippery liquid into my hand.
"You do it! And be nice and gentle I don't want to come before I get it in yer!"
I awkwardly reached behind me and felt around until my hand came into contact with Harry's hot engorged pole. It was rock hard and as I put my small hand around it, it felt enormous and menacing as it throbbed in my hand. Harry looked down to see me standing legs wide apart on high-heeled feet, my legs encased in diaphanous white nylon and my white satin panties pushed to one side of my arse. He watched as my long delicate fingers, their red painted nails glimmering with the shine of the lubricant, slid feather-like up and down his hard cock, coating it with a generous amount of KY jelly.
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I looked to one side and saw that I had left the wardrobe door open and I could see Harry and myself in the full length mirror. I looked just like a pretty nurse, a slutty nurse with a ridiculous cap perched on her head, bent over, pretty and pathetic as I reached back behind me and slowly smeared lubricant up and down Harry's penis. This nurse was about to be raped! Then I looked up and saw that Harry was looking at the same image and that he had a huge grin on his face.
"Oh Nursey, you're going to get it now!" he groaned.
His hands gripped my hips tighter and I felt his now lubricated glans press hard against my sphincter. But there was something preventing his entry; the nylon of my pantyhose! He hadn't pulled my pantyhose down or torn a hole in them!
"Pantyhose!" I gasped.
"Yes, I love them!" exclaimed Harry and gave an enormous thrust with his hips.
Christ! I felt the head of his penis slide inside my tight hole, the lube assisted but the nylon gusset of my sheer to the waist hose was also pushed inside me. The pain of having Harry's hard cock was bad enough but the nylon wrapped around the head of his cock was like sandpaper on the walls of my rectum.
"Oh God!" I groaned in agony and looked at my reflection in the mirror.
I was impaled on the head of Harry's cock as I stood with my legs spread, skirt hitched up and Harry's huge gut hanging over me as he thrust harder. I could see his eyes closed in concentration and ecstasy as he stuffed more of his tumescent member inside me. I felt my pantyhose grow tight around my buttocks and between my groin as harry forced more of the sheer fabric inside me, wrapped around his hard cock. He was groaning and gripping me so hard that the pain was almost more than I could bear; I felt a searing heat as my insides were invaded.
Suddenly I felt the flimsy nylon pantyhose give and Harry's well lubricated shaft drove itself all the way inside me as the resistance of the nylon parted.
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It was so big and in me so deep that it knocked the wind out of me and rocked me on my heels. I felt Harry's flabby thighs against mine, his jeans whispering on my nyloned legs as he ground into me. His large gut now rested firmly against my lower back and my hands gave way as his full weight was pressed against me.
"Don't fall over Nursey," he laughed, "I'm just about to start the ride!"
With that he pulled me up and back against him so that I was standing. I was rocking on my heels but Harry held me firm and spun me around so I was pressed hard against the mirror. My skirt had fallen down and was covering our intimate parts where Harry and had me impaled on him. He pushed me harder against the mirror and I smelt his rancid breath as he started to kiss my neck. One hand held me locked against the mirrored wardrobe as I felt the other fumble around at the front of my skirt. His hand went under the hem and began to stroke my pantyhosed thighs as Harry started to slowly rape my back passage.
It was not as excruciating as when Eddie raped me without the lubricant, but Harry's cock was a lot thicker and I felt so full of him that I would explode. Harry started to thrust slowly in and out of me, hardly moving his cock more than an inch in and out; he was panting as he slobbered at my neck, kissing and licking me with his foul mouth.
Harry's hand stroked my thighs and groin as he slowly fucked me, he obviously delighted in the feel of the slinky nylon and satin on his skin because he had shucked down his pants and was pushing his crotch hard against my pantyhosed arse on the in stroke. Harry now began to fuck me harder and faster, he breath in great explosions as he established a had and fast rhythm.
"Open your eyes bitch!" he gasped against me, "look!"
I opened my eyes and was humiliated by what I saw reflected in the mirror. Harry was thrusting against me, his jeans around his ankles and his sweaty body moulded to my back; his hand was under the front my skirt ferreting around, pawing and stroking.
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Harry's ugly face was beside mine and he slobbered at my neck. He was thrusting in and out pivoting his waist to get all of himself inside me, rubbing his balls on my nylon covered ass at the top of his in-stroke.
My back passage was filled and it ached with the size of the invading member that slid in and out of me, but oh god no! I could feel the spongy hard mass of Harry's glans as they pushed on my prostate; I couldn't believe it but again I felt the first ripple of sexual pleasure. I was not about to give this pig the idea that I was becoming aroused so I decided to end this rape as soon as possible.
I leant forward more so that my buttocks pushed out further and scrunched my hips from side to side to increase Harry's pleasure and ensure my nylon encased cheeks rubbed against him, as he obviously loved the feel of that. I turned my head sideways so that harry could stretch his fat neck out and kiss my pouty lips; I gagged on his breath but concentrated on trying to get Harry to come.
Harry now stepped back slightly and pulled me with him so that I was again bent over with my legs spread. Harry now started to pound himself heavily in and out of me. I though that he would do some serious damage to my insides if he didn't stop soon; the pain was enormous, but I still had the tingle of excitement every time his cock rubbed my prostate. Harry fucked me harder and harder and was really grunting and panting now. He gripped my hips and pulled me back hard against him as he thrust forward and held me rock steady as he pulled back. He was now jackhammering himself in and out of me, groaning and cursing.
"Fucking bitch! Fucking Whore! Fucking take this you cunt!" he screamed.
He pushed in hard and ground his balls against my nyloned cheeks as he shuddered. His grip on my waist was like iron.
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I felt his cock start to convulse inside me as it shuddered and secreted his hot spend. Harry's cock actually expanded and I felt the walls of my back passage begin to tear as Harry came deep inside me. I felt jet after jet of hot seed stream into me as Harry stated to rock slowly back and forth again. Harry's semen further lubricated his cock and some of the pain went away. Harry was still hissing obscenities as he completed his climax. I felt his spend drip from my sphincter and run down my nyloned legs.
Harry pushed me forward and thrust back so that his cock slid out of me, a torrent of his semen joined the trickle running down the inside of my legs. I couldn't believe how much semen he had shot into me.
I couldn't move, I was bent over, my back aching, my legs locked apart and my back passage throbbing in agony. Harry pushed me sideways and I landed on the bed, sitting up, my legs spread and skirt hiked up.
Harry leant over me and kissed me full on the lips.
"That was worth every penny; you are one hot nurse," he laughed.
Harry grabbed a handful of my clean white skirt and wiped his cock on it. The silvery gleam of semen and KY jelly stained the fabric; there was also a faint trace of blood.
Harry hitched up his pants and made for the door, tightening his belt; he looked back at the dishevelled, raped, nurse sitting legs akimbo on the bed, a look of shock on her face and her tunic stained with semen and blood,
"Yep, you are one fucking hot nurse alright; maybe next time you can play Nun!"
I heard his laughter fading as he walked down the passageway past the other cells to what I presumed to be the waiting room.
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The waiting room where undoubtedly there were more customers waiting. I closed my eyes as the tears ran slowly down my cheeks.
To be.
