The Gambler

"Don't you trust me Kate?" I asked innocently.

"No...I mean yes." She paused fighting her own inner battle then out came the truth. "No, no I'm not sure I'm going to trust a man's word ever again."

"Well Kate," I started gravely before letting her off the hook. "I think that's a very sensible idea. I consider myself an honorable person however in business I never do anything without a contract." She smiled, the weight lifted. "However," I continued, "I'm not sure where we will find a lawyer at this time on a Friday night."

Kate opened her little clutch purse and pulled out some folded paper.

"I printed up something..." She handed the papers to me again uncertain.

We'd arrived at the ground floor so I found a quiet corner and perused what Kate had prepared. It was written very simply. There was an area for Kate to sign her name under a paragraph stating she would be my personal assistant in every way for three nights. Another place for me to sign below a statement that I would provide the sum of fifty thousand dollars in exchange for her services.

"Did Jeremy want this?" I enquired.

"Umm, we both did." Her hesitation told me it was a little white lie.

I glanced at the document again. "I'll sign it Kate." I said trying to sound disappointed she didn't trust me. "However if we want it to be a proper contract then we should have a witness sign it as well."

"Oh right, of course... Umm would they have to read it?"

"Generally yes, a witness would want some idea of what they were signing."

Kate looked uncomfortable at the prospect but I maneuvered her over to the hotel concierge.

"Excuse me, I was wondering if you could be a witness for a contract we are about to sign." I asked the young lady.

"Certainly sir," she replied, eager to please.

After procuring a pen from the top pocket of the concierge's jacket I signed and dated the contract with a flourish before turning it one eighty degrees for the witness to sign. Kate signed her section next and the concierge witness her signature. Passing the completed contract to Kate I leaned in close.

"Let's go and eat." I said with a smile as I took her arm and escorted her to the door.

I'd considered where we were going to eat very carefully. At first I was going to go all out and book the best restaurant in the city but then I had second thoughts. I mean, are you ever really comfortable in one of those places? With all the foodie wankery going on in them the dishes have more in common with a work of art rather than food.

So instead I decided on a nice modern Italian place I knew. The chef there made beautiful traditional Italian meals with a modern twist using fresh ingredients. The space was brash and loud, the wine flowed and everybody had a good time. Just two blocks down the street, it was going to be perfect.

We got a cab there, it was possible to walk but Kate shoes didn't look designed for walking. She still seemed on edge and her eyes darted about searching the crowds on the sidewalk. I took her hand to reassure her. She gripped it tightly but didn't look at me. The cab dropped us right outside the front door and we were soon inside out of the crowd.

We were greeted by the chef's daughter who showed us to our table. I was keen to have a drink and show Kate off at the crowded bar however one look at her face told me that wasn't an option. I could have pulled rank but it wasn't the time to do it yet.

After starting off with champagne we had another bottle of wine with our main meal. We talked constantly about a myriad of topics. I deliberately never let the conversation touch on the arrangement we had or the previous Friday night. Feeling full and tipsy after our meal we sat on one of the comfy lounges in the now deserted bar section with a coffee. Kate was very relaxed, sitting close enough that our legs touched. Her dress had ridden up when she sat down. My hand stroked her exposed leg, gliding lightly over the sheer stockings she was wearing.

"What have you got planned for later?" Kate asked after a little yawn. Her head now rested on my shoulder.

"I haven't really thought that far ahead," I lied.

"You are such a liar," Kate giggled, digging into my ribs with her elbow.

"What would you like me to do?" I asked her.

"Well, I can't really say. It wouldn't be polite." This time the giggle became a full blown laugh.

Could this be right? Was Kate flirting with me? This was beyond my wildest expectations. I could feel a stirring in my loins. I wondered whether I should get her straight back to the hotel so I could fuck her or wait and let things progress more slowly. In the end I decided to let things meander along. After all, the thrill is in the hunt not the kill. Although I was looking forward to the kill as well.

We talked in low giggly whispers for another twenty minutes. My arm that had been around her shoulder had slipped down so my fingers now felt the curve of her breast. My other hand slowly crept its way higher. Kate's legs parted to allow it to touch the bare flesh above her stockings. I wasn't the only predator. Her hand was on my thigh and her little pinky moved languidly back and forth across the top of the ever growing lump in my pants.

The time had come to leave. In the cab Kate wasted little time. She fished out my cock and dropped her mouth onto it. She'd obviously been practicing on her loser husband. Her lips glided up and down while her tongue bathed and sucked. I almost told the driver to take the long way around but I wanted her up in the room. I couldn't waste Kate's horniness on a blow job.

We stumbled quickly through the lobby together. Luckily there was an empty elevator waiting. Inside the metal box we were at each other again. I lifted her dress above her waist and slipped my hand inside her frilly French knickers. Kate was smooth and bare. I cupped her whole sex with my hand feeling it's heat before I pressed a finger inside. We kissed hungrily until the bell rang to let us know we'd got to our floor.

Outside the automatic doors I spun Kate around and unzipped her dress. Pulling it off her shoulders I let it slip to the floor. I gave her the room card and asked her to walk slowly up the corridor until she got to the right number. Kate stepped out of the discarded dress before slowly strutting away from me in her lingerie. I bent down to pick up her garment but it took several grasps because I couldn't take my eyes off the sexy lady. She stopped and looked back over her shoulder at me. The hooded eyes and painted pouting lips were like neon signs flashing, I want sex now.

"I'm here sweety, are you going to catch up?" Kate purred before she pressed the card into the slot.

I raced up the hallway catching the door as it was just about to shut. Inside Kate was already on the bed. When she saw me she grinned mischievously. One hand cupped her lace covered breast while the other was inside her knickers rubbing her cunt.

"Are you going to get undressed and join the party?" Kate gushed before puckering her lips.

Was this the shy innocent wife I'd fucked lady week? I was nude as fast as my buttons would allow. Before climbing on the bed I pulled off her knickers but I left the bra on. I liked the way it pushed her small breast up and together. Kate had two fingers sliding slowly over her pussy, her face was flushed and her breathing fast and shallow. It was time to take control.

"Roll over and get on all fours." I ordered.

"Yes master," Kate replied mocking me.

I slapped her arse hard. Kate squeaked as her head spun back to look at me accusingly. I pressed two fingers into her dripping snatch as far as I could. Her eyes lost their venom and she gasped.

"I'm here to fuck you, not to be fucked with." I sneered as I pulled my fingers clear before ramming them back in again.

Soon I'd added another finger. Kate's juices were dripping off my hand. It was time to prepare her. When she rocked forward I changed the angle of my fingers so when she came back to impale herself again they slipped up between her arse cheeks. Kate quickly changed direction and the next time I sank my fingers back into her beckoning twat. I continued to alternate as she speed up trying to get herself off.

I relented my teasing by rapidly jamming my digits in and out of Kate's cunt. At the same time my other hand slid down from the small of her back so the thumb disappeared between her gorgeous globes and found her other opening. Kate was to far gone to care as I pressed my thumb home inside her tight arsehole.

She continued to bounce on my other fingers as her climax reached its peak either oblivious to the anal penetration or further excited by it. Kate's gyrations ceased and I removed my thumb from her bum first and then my fingers from her sodden cunt. She relaxed, until I sank one of my wet fingers deep into her arse.

"What are you doing?" Kate asked surprised by the intrusion.

"I think, if I remember our agreement correctly." I paused to twist my finger in her tight clenching hole. "Whatever I want."

"No, not there." Kate tried to pull away suddenly alarmed. "No there's no way it co.. Ugh."

She didn't get to finish the sentence because I added another wet finger to her hole.

"Don't you think it will fit darling?"

"Please, please stop." Kate was looking back at me forlornly.

"Not until you're ready Katie. If I try too soon it will hurt more." I stopped manipulating my fingers briefly and pushed a strand of sweaty hair away from her eye with my other hand. "Just relax, breathe dear girl and you will be enjoying it in no time."

I resumed fingering her butt. Kate pressed her face into a pillow. I worked both fingers back and forth until they were embedded to my knuckles. My cock was aching so even though it was a bit early I decided to try and fit it inside Kate's delicious rear end.

Slipping off the bed I found the lubricant I'd bought. When I clicked open the cap I'm sure I saw a tremor pass through Kate's body. Positioning myself on the bed behind Kate again I thoroughly coated my cock with the slippery fluid before putting some more on my fingers. Prying her butt cheeks open I pressed my lubed fingers against her arsehole. Kate flinched as I gently eased first one then two fingers inside. After repeating the process again it was time.

Shuffling forward I pressed my cock head against her puckered hole. I applied more pressure and the opening began to yield. As her sphincter stretched around my engorged head Kate emitted a low growl that got higher in pitch the deeper I went.

"Eeeeooowww... Wait! Wait!" Kate's hand pressed back against my abdomen just as my head lodged itself inside.

"Alright, alright Kate." I said softly, "I'll just stay still. You relax and let me know when I can start again."

I kept a firm grip on her hips but didn't push again. Kate turned her head to the side on the pillow. She was panting with her eyes screwed shut and her fingers still braced against my stomach. Gradually she got her breathing under control and her hand stopped trying to pushing me back. It still hovered close in case I tried before she was ready.

"Are you okay Kate?"

She just nodded with her eyes still closed.

"Can I keep going?"

Kate didn't say anything. She pressed her face into the pillow again and nodded tentatively.

Increasing the pressure again another inch slipped inside before her hand pressed against me again.

"It too big," Kate complained.

"I can assure you it's not Kate. Your arse will stretch dear and before this night is over you will have my cock balls deep in your arse." I replied sternly.

All evening I'd been taking it easy on her, now I had to exert my control. I backed off a little before pushing back to where I'd been. There wasn't another complaint so I kept going, fucking her with just an inch of my dick. After a minute I began to press harder so I went deeper. Kate was grunting into the pillow with each thrust until I had just over half my dick inside her.

"Stop! Stop! You're splitting me in two." Kate squealed.

I was on the backstroke and she twisted from my grip and crawled forward so my cock popped out. Free of her tormentor Kate rolled onto her side and tucked herself into the fetal position.

"You're just delaying the inevitable dear." I said as I reapplied some more lubricant.

I reached forward and hauled her back towards me. Kate didn't complain when I rolled her back up onto her knees and got her in position again. This time I slipped in much easier. In fact I was damn near all the way in before she made a sound. No scream or asking me to stop this time. Just a gasp before I pulled back. This girl was ready now.

I went in hard and didn't stop until I was all the way inside. Once again no complaints, no need to rest, let fucking begin. I set about wreaking havoc on the lovely Kate's anus. Her hands gripped the sheets and her head hung low but she stuck with me. As I was getting close the little moans started. Oh yes, she was getting into this. I went even harder and her moans became short grunts just as they had the week before. My balls were boiling so I gave one last thrust and held myself deep inside as I released my seed. Kate's head came up and out came the stifled groan as she pushed back and came herself.

"Ohh... God... That was incredible." I said as I pulled out and slumped down on the bed. "You are incredible Kate."

Kate stayed where she was on her knees with her arse in the air. I went to the bathroom and cleaned up. When I came out Kate was on her side with her back towards me. I pulled up the covers then slipped in behind her. As I put my arm around her she snuggled back against my chest. I had this one. I'd just busted her cherry arse open but she still wasn't rejecting me. Right then I wanted to fuck her again however I knew it was too soon. Instead I lightly stroked her hair.

"Sleep my darling Katie." I whispered. There will be plenty of time tomorrow morning to get another shot at her.

Kate.

Mr. Cooper's face was bright red. The tendons stood out on his neck, his eyes were closed and his face contorted as he pounded away on top of me. I was folded up like a pretzel. My legs caught inside the elbows of Mr. Cooper's outstretched arms.

"Ohhh fuuuck, I'm cumming Katie, I'm cumming!" He groaned.

I felt the warmth spread through my womb as he bathed me in his seed. I began working my hips frantically against him anxious to drain every last drop from his balls.

"Ohhh, ohhhh, ohhhh." I gasped.

"Yeah Katie, take it alllll."

Bob collapsed and released my legs. He stayed on top of me his cock still planted deep inside. When his breathing became less erratic he lifted himself up and his dick slipped out of my slick opening.

"I think you are the best fuck I've ever had Kate." He told me as he laid down beside me.

I let my legs drop as he spooned my body. His upper leg crossed mine and his arm was draped across my chest so his hand cupped my breast. I let him stay there for a while until his hand began creeping further south.

"I'm going to have a shower. I've got to get home." I said pushing his arm away.

"Just a little longer?" He begged trying to hold me down.

"No, the sun is up so the night is over."

I escaped his clutches and made it to the bathroom. I was glad to see the privacy lock so I clicked it before I jumped under the spraying water. Just before I washed my hair I heard a rattle as Bob tried the door. Satisfied I was safe from further molestation I continued my shower. When I left the bathroom Mr Cooper was laying on the bed, still naked, reading a complimentary newspaper.

"Are you sure I can't convince you to stay longer?" He peered over his paper at me.

"I've got to go." I said dressing quickly.

I was about to leave so I turned to say goodbye. Bob was walking towards me holding the designer bag the dress had come in.

"Don't forget this. I'm sure Jeremy would love to see you in it."

I doubted that but I took it anyway. As I reached for the bag he grabbed my wrist and dragged me into an embrace.

"I'll see you in two weeks." He whispered fiercely into my ear.

I twisted away and stumbled to the door and out into the corridor. The door swung shut and Bob made no move to follow. There was a mirror near the elevator and I adjusted myself while I waited. I move quickly through the lobby with my head down even though it was practically deserted. It was just before 6am so cleaners were still polishing the floors.

Outside I got the doorman to hail a taxi. As it came up the driveway a hand grabbed my arm. I wheeled around shocked and worried I'd been discovered.

"Hello Kate wasn't it?"

It was the concierge from the night before. I nodded unsure what she was doing here and why she was talking to me?

"I'm just off home after my shift too." She explained before pulling me closer and talking in a hushed tone. "Just a word of warning dear. If you want to continue doing business in this hotel then you have to pay ten percent commission or we get security deal with it."

"You think I'm a prostitute?" I tried to pull away in alarm.

"Obviously you're new to the game which is why I let it slide last night but I'm warning you now. Next time you have to pay the piper." She hissed as the doorman opened the cab door for me.

I pulled free from her and threw my overnight bag on the taxi's back seat. Before I got in I passed her the dress I'd worn the night before in its bag.

"For last night," I said angrily. "And don't worry I won't be back."

Part Three. Two Weeks Later

Michael Delacourt. (Mr. D.)

As I turned into the circular drive way the tyres squealed. My boss didn't like tardiness and I was on the verge of being late. After parking quickly I hustled up to the front door and hit the buzzer. The door swung open and my boss stood glowering at me.

"Your late." He said.

I quickly glanced at my watch to see it was two minutes past seven. I'd been working on a few excuses as I walked towards the door but decided to go for the apology instead.

"Sorry boss."

He stayed blocking the doorway for some time silent. I thought he was going to send me away until he stepped back and motioned me inside.

"She's been delayed as well." He explained as I maneuvered my bulk past him. "Also I'm not to be referred to as 'boss' tonight. Bob will suffice but I don't want you to get used to the idea."

"Okay bos... Bob."

After closing the door Mr. C led me to what he called The Club room. It had oak panelling on the walls and ceiling. Large comfy chairs faced a stone fireplace. A full size billiard table dominated one end while the other had an ornate bar area.

"You stay here. I'll warm her up and then bring her in." Mr. C said before striding back out again closing the door behind him.

I hoped he'd say grab a drink but he didn't. I took a seat in one of the big armchairs before pulling out my phone. It was playoff time so the business was brisk. I should have been at the office but when Mr. C calls he doesn't take no for an answer. I called and checked in with my manager to see how much they were holding on the game. Everything was covered so I hung up and looked around the room.

Mr. C had a nice place. It had been in his family for generations so he said but I wasn't sure I believed it. The suburb and the house reeked of old establishment money. Mr. C's family started out in the illegal gambling business so I don't think they would have fit in at first. Bob's dad had taken the first steps to legitimacy. Firstly as a legal bookmaker at the racetrack and then into regular business. Started out in horse transport, although rumor has it this takeover wasn't particularly kosher, before moving into general freight.

Mr. C went to the best schools and came home with a degree in business and computing. Used Dad's money to launch a tech company that was good enough to attract the eye of a couple of bigger players. A bidding war broke out and Mr. C ended up a very rich man at thirty five. He took over the running of the family transport business as a hobby in his "early retirement."