Lady In The House Ch. 09

Eddie obviously did not care too much for authenticity; Mabel has selected a pair of patent leather black high-heeled court shoes. They slid easily onto my stockinged feet and as I stood I was relieved to find out that it was a lot easier to balance on these wedge heels than the tapered spiked heels that I had been forced to wear up to now.

I sat at the makeup table and adjusted the lamp so that I had good light to apply my makeup. It still amazed me how quickly I had become adept at the feminine art of applying makeup!

First I applied the foundation and powder. My eyes I decided, would be in dark shades so I applied dark gray eye shadow and black eye liner. I underscored the eyeliner on my lower lids with a thin dark blue line for contrast. I applied lashings of mascara so that my lashes were almost caked with a thick black coating. I lightly applied a dark shade to my eyebrows with the eyebrow pencil and completed the look with a light pink shade of blush on my cheeks and only a slightly darker shade of pink lipstick. I decided to experiment this time and applied a coat of lip-gloss. I pulled on and adjusted my wig; just the look I wanted; I looked like a naughty schoolgirl with the lighter shades of makeup I had applied but with my dark eyes contrasting wonderfully.

Next I put on the long-sleeved cotton blouse, being careful to keep the pristine white garment free of makeup. I buttoned up the blouse, still finding trouble with the way women's clothing buttoned on the opposite side. I pulled the school uniform tunic over my head and adjusted it. It was a dark blue and green tartan. The dark colour emphasised my pale face and dark eyes. The bodice was tight against my torso; the skirts were pleated and came to just above my knees. Then I had an idea; the finishing touch!

I rummaged around in the drawers until I found what I was looking for. I sat on the edge of the bed and kicked off my court shoes. I pulled on a pair of white cotton anklets over my stockinged feet and then stepped back into the black patent leather court shoes. I looked fantastic! I left my ears unadorned but slipped a simple gold chain necklace around my neck.

I sat back down on the bed and started applying two coats of pale pink nailpolish to my nails. While I was doing this I had time to think and realised what I had done. 'My God! What the fuck was I doing!'

Not only was I capitulating with the crazy bastards who forced me to become a crossdressed prostitute; I was dressing like a woman as if it was a natural thing to do! I was working at looking good and even being innovative to achieve the 'look'. Fucking white anklets; what the fuck was I thinking of!!!! Had these sick fucks brainwashed me?

I was about to get up and do; I don't know what; remove my makeup and clothes? rebel? scream? then I heard the unmistakable sound of Eddie's voice as he approached.

"Oh fuck yeah Dave, you will love my latest acquisition! She's got an arse to die for; and with only a little bit of training she already knows how to suck cock like she was born to it."

"I don't trust the cunt though; she's too fucking smart by half," he added.

"Smart mouth on her; and you can tell she's planning something. You have to remember this twat ain't like Charlotte and the other dumb cunts in my stable; he was a businessman, pretty smart and well to do on the outside until he got done for running some kid over while drunk."

"She still thinks there's a way out of her job here, and I'm sure she's got ideas about getting outside or transferring to somewhere else, so be careful if you take a fancy to her; she might try it on, like I said, she's just too fucking smart!"

Eddie was obviously discussing me with the punter he was escorting to my cell. So Eddie knew I had plans to try and get out of the fucked up predicament I was in. So what! If I got my chance you can bet I'd be gone in a flash!

Then it dawned on me what Eddie had said, 'so be careful if you take a fancy to her'.

'Maybe that meant my first customer of the night might be a man of influence and power,' I thought.

'Maybe I could use him to my advantage? Better be careful though; I had fucked up royally when I tried it on with the Warden; best find out all I can about this guy before I try to use my newfound charms on him,' I considered.

"Well hello Michele; don't you look lovely this evening," Eddie said with an evil smirk on face as he stepped into my workroom cell.

A tall good looking man dressed in prison fatigues walked in behind Eddie and came to a complete stop in the cell doorway and looked me up and down where I sat on the edge of the bed.

"Christ Eddie she's a stunner all right; you weren't exaggerating on bit. Hi sweetie," he said pleasantly, walking all the way into the cell.

"Say hi to my best friend David, Michele; don't be rude!" Eddie smiled my way.

"Hi David," I said in my best attempt at a coquettish voice.

"Davy here is a very special friend of mine Michele, and I promised him that you would treat him very nice this evening; so you do that for me and maybe I'll be nice to you later ok?" Eddie said in a voice that left no doubt that if I wasn't nice to Eddie's friend I would be very sorry.

"Of course I will Eddie," I answered meekly.

"So Davy, will she do; is the get-up ok?" Eddie asked.

David had been looking me up and down ever since he arrived in the cell; he hadn't taken his eyes off me. "Yes Eddie she's perfect, and I bet she can be a very naughty school girl too," David chuckled.

"Yes; and speaking of being naughty; Davy why don't you go and see Mabel and bring yourself back a bottle of something to drink while I have a little chat with Michele. Just give us five ok?"

There was no doubt that although Eddie was treating David with more respect than I had ever seen him treat anyone else, Eddie was still the one giving the orders.

"Sure; is scotch ok Michele?" David asked my way.

"Fine," I answered.

David ducked out the cell and I heard his footsteps disappear down the corridor. As soon as David left the cell Eddie strode over to me and held out his hands.

"Stand up sweetheart and give us a good look at you," Eddie said.

I allowed Eddie to assist me to my feet. He looked me up and down and smiled.

"Wonderful," he said. Then with lightning-quick speed he punched me in the stomach.

"You fucking cunt! What the fuck do you think you were playing at with the Warden? Me and you are going to have a little chat later and I'm going to remind you how things work around here!" Eddie barked.

I collapsed on to the bed, the wind completely taken out of me. I doubled over in pain as I tried to breathe. I felt like I was dying, I couldn't get any air in my lungs.

"Don't you start crying and ruin your face you fucking cunt bitch," Eddie snarled.

"You fucking soak up that pain and get yourself ready. David is my best friend in this shit-hole and I promised him you would treat him special, so you just get your pretty arse off that bed, breathe deep, and be ready when he gets back here."

I forced myself to stand and eventually I could breathe in shallow breaths but the pain in my stomach was excruciating. Even so I realised that I was lucky that Eddie had bought his best friend to see me otherwise he may not have cared about marking my face with his fists. I stood there looking down getting my breath back.

Eddie lifted my face to his,

"You try any of your fucking smart moves with Davy, Michele and I'll put you in hospital you bitch. I'll accept the loss of earnings while you recover; besides some cons in here like being sucked off by bitches with no teeth; slides in nice and easy so they say, so you fucking well behave," Eddie threatened.

He released my face just as David walked back through the door with a bottle of scotch in his hand.

"I'll leave you two kids alone to get acquainted ok?" Eddie sniggered.

He pulled the heavy curtains across the bars to my cell, slipped through them and slammed the door shut.

"Don't disturb them for a couple of hours Mabel," I heard Eddie yell at her as he walked off.

I was alone in the dimly lit cell with David; we had complete privacy. David looked me up and down again.

"Drink Michele?" he asked, a smile breaking out on his handsome face.

"Please," I smiled back suppressing a grimace of pain from where Eddie had punched me.

David half-filled two glasses with hefty shots of the dark amber liquid and handed me one.

"Michele you are one pretty lady if I may be so bold. And that schoolgirl outfit is just as kinky as hell," he said grinning at me with the confidence the way only men secure in their good looks seem to be able to do.

He suddenly came over serious.

"Don't get me wrong; I'm no noncer or anything. I like to take my fun with adults not juveniles; it's just that I love trannies when they get dressed up in sexy costumes like that."

"Oh fuck I've done it again; I'm sorry I didn't mean anything derogatory calling you a tranny."

"Shit, I'm behaving like it's my first date; let me start over."

We both looked at each other and suddenly burst out laughing. It was honest laughter bought about by David's embarrassment and stumbling apology. He was very handsome indeed; tall and slim with black wavy hair, deep blue eyes with laugh lines at the corners, white teeth and full sensuous lips. He was deeply tanned and obviously made the most of his allocated time in the exercise yard.

"Alright. Michele, I'm David but please call me Davy."

He took a big gulp of scotch and continued.

"I'm what you might call a business associate of Eddie's; let's just say I do him favours and he does me favours."

"I'm fourty something, single, bisexual and disease free," he laughed again.

"And oh; to be honest I do have penchant for transvestite hookers dressed up as school girls," he finished, laughing again in his easy way.

He had managed to put me at ease and I could see how he could easily win over any woman that took his fancy; or man for that matter, he did say he was bisexual after all!

"Hi Davy, I'm Michele and a woman never tells her age," I smiled back at him, taking a sip of the single malt.

"As for the rest...", I started but Davy interrupted.

"I know the rest honey," David said, "and don't worry I'm not here to force you to do anything you don't want to do. Please sit."

I sat down and as I did I winced in pain as it flared up where Eddie had punched me.

"The prick! He hit you didn't he; while I was gone getting the scotch, the bastard hit you," Davy said and sat down beside me and took my hand.

"If it had anything to do with me I'm sorry Michele; I don't know how anyone could be cruel to you."

I was taken aback, but wary. So many times since I had been forced to crossdress men had started out being nice to me and had then turned vicious.

"No it was my own fault," I answered, "I did something stupid and paid the price."

"Well I don't believe that a lovely creature such as you could do anything wrong; and anyway the most you would ever get from me is a light spanking on your tidy bottom," he started laughing again and I couldn't help but laugh with him.

We both looked down into our drinks and took a sip as the laughter died down into an awkward silence.

Davy put down his scotch and turned towards me, he reached and gently turned my face to his.

"Look Michele, I do know your situation; Eddie told me the whole story. I know you are being forced to this against your will; and as I much as I would love to make love to you I an not going to force you to do anything that you don't want to do."

"Don't get the wrong Idea, I often come to Eddie's stable and go with the girls here; I do love making love to transvestites; but most of the girls here are willing to do what they do, even if they were initially forced or blackmailed into it by Eddie."

"But I have never forced myself on another person and don't intend to start now," he finished.

I was quite taken aback, Davy seemed to be the most genuine and gentle man I had met since I got into this mess; and he was just stunningly handsome. I figured that if I was going to have to pleasure punters all night, I might as well pleasure someone who is kind, handsome and obviously has some sort of influence in this place.

I had badly miscalculated with the Warden; I decided I would put my efforts into making Davy happy and play him along until the time is right to use his influence somehow to help me get out of this jam. Tonight I was his.

I reached out with my long feminine fingers with their pink painted nails and stroked his face.

"Davy you are the nicest man I have met in this place; how can I not like you?" I smiled and gently pulled his face to mine.

I kissed him on the lips and slid my tongue inside his mouth and ran it along the top of his gums; women had done this to me before and it drove me wild. Davy responded and took me in his arms. I allowed him to pull me against him as he held me tightly but tenderly. He didn't try anything else for over five minutes; he was just contented to kiss. We kissed deeply and passionately, and besides the smoky taste of the scotch, his breath was as sweet as a baby's. I was becoming genuinely aroused; it was not just lust invoked by an instinctive response to stimulation, but a slow sensual awakening of my pleasure centers.

Davy eased me down onto the bed, never breaking the kiss. We ended up lying side by side our lips locked. After what seemed like an eternity of passionate kissing I was ready for more; my senses were actually screaming for further stimulation. My cock was straining against the lace panel of my boy-leg knickers, the lace stimulating my member. I pulled myself closer to Davy and lifted my leg up and over his body, the pleated tunic rode up my thigh and exposed the matching lace stocking tops of my nude nylon stockings.

Davy got the hint and started to stroke my legs and thighs, his hand sliding slowly and gently along the nylon. I kissed him deeply and growled in the back of my throat as the sensation caused by Davy's hands stroking my nyloned leg aroused me further. I started rubbing my crotch against his hard body in attempt to further stimulate my penis. Davy sensed what I was doing and gently eased me away from him slightly; I couldn't contain my disappointment.

But Davy didn't miss a beat, as soon as our bodies were separated far enough, he slid the hand that was stroking my leg under my skirt and went straight to my penis. He gripped it lightly through the lace panel of my knickers and began to slowly stroke it.

I groaned and Davy responded by sending his tongue into a frenzy in my mouth; it rolled around my tongue and tickled my cheeks and gums; he was an excellent kisser. At the same time he increased the speed of his hand stroking my turgid knicker-wrapped member. I knew that I couldn't hold on to my orgasm much longer and tried to pull away; I realised that Davy had seduced me to the point where I would let him do anything. I had allowed the tables to be turned; I was supposed to seduce him into my power, not me into his!

I was too far gone, I made a feeble attempt to extricate myself and gave up immediately as Davy tried to hold me where I was, lying beside him. We were joined at the mouth, out torsos pressed tightly together as we continued our passionate kiss. I was twisted at the waist so that my legs lay open on the bed. My legs were now spread wide, my skirt up around my thighs, the sheer nude hose on my legs running down to the cute cotton socks and the patent leather black high-heeled court shoes.

Under my skirt Davy's hand was now stroking me hard and fast through my knickers; I began to buck and writhe as my orgasm approached. My orgasm rocketed through me; I felt it through my own body. My senses were heightened to the pitch where I could feel, taste and smell everything intensified one hundred fold.

I could taste my lipstick mixed with Davy's sweet breath and the musky scotch we had drank. I could feel his tongue jack-hammering in my mouth, my long sleek nylon encased legs were sending those little electric shocks of pleasure I had become to love so much. I could feel the satin bra and suspender set, smooth against my bare skin, and the gray nylon knickers rubbing against my buttocks and scrotum as Davy gripped my cock in the front panel of the knickers and strocked me furiously.

I could smell the sweet perfume I was wearing and Davy's masculine after-shave, mixing with the musky hint of sweat as we both became further excited. Then I could smell the slightly starchy smell of my semen as I spent into my knickers.

My climax shot through me, and I shuddered and groaned. Davy continued to stroke me, milking my seed into my knickers, the semen lubricating the lace and increasing the intensity of my orgasm. As the last of my emission dribbled into my knickers Davy released his grip on my erection and slid his hand under my silky buttocks and turned my lower body towards him, his hand on my ass pulling me close against him. I lifted my leg again, rubbing my stocking leg against his muscular thigh, milking the last sensations that I could out of my subsiding orgasm.

Davy held me like that, our bodies side by side, for about five minutes; never braking our kiss, my lips were almost numb. Then he stopped kissing me and looked into my heavily made-up dark eyes and said,

"You like?"

"You bet," I responded smiling into his handsome face.

Now that we had stopped kissing I pulled myself free of our embrace briefly and Davy frowned; but not for long as I readjusted our position on the bed. I pushed Davy onto his back and I straddled his waist, my pleated schoolgirl skirt spread over his middle. I leaned down and kissed him briefly on the lips and then pulled back so I was sitting upright. I looked down into his beautiful deep blue eyes and said,

"Now, what can this naughty schoolgirl do for you?"

To be continued...