My Boss, My Master – Part 5 – Winner’s Privil

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My Boss, My Master – Part 5 – Winner’s PrivilThis story is a work of fiction. Constructive feedback is welcomed, as are suggestions and requests. Leave a comment or send me a message. I don’t bite… unless you let me. I hope you enjoy reading it as much as I enjoyed writing it.I’m going to try to avoid some of the words that xhamster ***’s out, such as f.a.mily, s.i.ster, f.orce, etc, but in places you’ll just have to bear with it.When Friday finally came, I was feeling sick to my stomach from worrying. I hid it well enough, but it must have been completely obvious that the mystery was killing me. Mr. Smith chuckled as I entered the office early.”Eager to get going today, are you, Lucy?”I blushed. “Well, sir, I just thought if I’m leaving early-“”Don’t worry about it, this works out just fine. We need you out all day anyway. Head back downstairs, my driver knows where to go.””Yes, sir,” I said. Those words were getting to be almost reflex at this point.Mr. Smith’s car was waiting for me as promised. His driver was a professional type, uniform and hat and all that. He opened the back door for me and then went around to the driver’s side. We started moving right away, with not a word beyond his curt “Good morning, Miss.”He drove me first to a downtown dress shoppe. He stopped out front and told me to go inside.I’d never been in a store so nice before. The store owner greeted me at the door – apparently I’d been expected – and told me to head back to the sizing room and take off my clothes. I did as she said, trying not to think about the three mirrors pointed at me and the bright lights accenting everything wrong with my body.The dressmaker was a tiny, ancient-looking Asian woman. She took my measurements in seconds, scrawled something on a pad, and held a few bits of fabric up to my skin. Then the owner came back and told me they had all they needed, and to go back out to the car.I was more confused than ever. Didn’t they want me to try anything on? Apparently not. The dressmaker was already gone and the owner didn’t seem to want anything more from me. I shrugged and went back outside.The driver took off again as soon as I was belted in. Now it was out to a suburb and we stopped at a spa. But not just any spa. This was the sort of place where you go for a weekend, and then pay the bill with your first-born c***d.I wanted to ask if this was for real, but by this point I had stopped questioning the expenses of Mr. Smith’s tastes. I could still be shocked, just not surprised.The rest of the day was a blur. Realistically, it should have been a long weekend. I was rushed through salon chairs, skin treatments, manicure, pedicure, massage, acupressure… there was a break for lunch in there somewhere, but I don’t really remember it. At the end of the day, I was exhausted and my richer, prettier twin had taken up residence in the nearest mirror. My hair had been trimmed, teased and colored to bring out the natural red in my auburn tone, my face was smooth as a mask and my lips and cheeks had a subtle tint to them that brought out the green in my eyes. They’d even painted my nails a deep purple-red. I looked sort of like Jessica Rabbit’s shy cousin.The hairdresser in particular was not pleased with the pace of things. She grumbled about being rushed and cast dour looks at me and gave very stern instructions for how I was to sleep so as to preserve her hard work for the next day. Which was a good thing, because when I got out of there I was just about ready to pass out in the car.The driver took me home from there, which was good because it was definitely past time for dinner.Of course, that had been thought of too. We pulled up to my apartment building and the driver let me out of the back, then walked around to the passenger side seat and pulled out a packaged-to-go steak dinner. It was still steaming hot. I thanked him, then thanked God that he didn’t seem to want a tip. How cheap would I look tipping like a poor girl after that day of tuzla escort expensive treatment!I ate carefully, followed the instructions for keeping my hair nice, and went to bed.I slept through most of the morning, had a big brunch-like meal, and sat in my living room, watching TV reruns and trying not to throw up. At close to dinnertime, there was a knock on my door. Standing outside was one of the makeup ladies from the spa. She held a large box in one hand and a bag from a steakhouse in the other, with what looked like a doctor’s bag slung over one shoulder.”Good, you didn’t fuck up the hair,” she said, shoving her burdens into my arms and pushing past me into my apartment. “Eat carefully, get dressed, and I’ll see what I can do about making you look presentable.”I opened my mouth to object to the intrusion but she was already unpacking her bag on my dining table and she shot me a look that said that my bullshit was not welcome.I shrugged and sat down to eat, then carefully washed my hands and opened the box she’d shoved at me to see what was inside.The make-up girl looked up from her own bagged lunch. “Call me when you’re in the corset. You’ll need me to lace it.” I nodded and wandered back to my room to get started.She was right about the corset. It was steel-boned and looked like it had been tailored perfectly for me, although I have no idea how all this happened in a day. Once it was cinched on and tightened – an act that required my new taskmaster’s knee being planted firmly in my spine – I had an almost cartoonish hourglass figure, and the lacy top of it held my breasts up so high you could balance drinks on them. Black stockings and a matching black thong completed the image of an upscale whore. Then I pulled on the dress.It was black, but it was some sort of sheer micro mesh that was almost transparent when I stretched it over my curves. The front was cut so low that the lace from the corset was peeking out, and the skirt… well, this thing was more like a long tight shirt. I checked the box, but aside from a pair of wicked spike heels and some jewelry there was no other skirt in evidence. I twisted and checked my back in the mirror. The thing hugged my ass like it was painted on. If I bent forward in the slightest, my cheeks would show.I sighed and put on what looked like diamond ear-studs and a matching pendant that dipped down to sparkle in my now very ample cleavage, then went out to look for the make-up girl again.She tsk’d at me and straightened the dress a little, then sat me down, applied the most incredible perfume I’d ever smelled from an unlabeled bottle, and spent half an hour touching up my face.An alarm went off on her phone and she sighed. “That’ll have to do,” she said. “Your ride’s here.”I slid on the shoes, taking a few seconds to get my balance, and headed for the door. On the way I grabbed a long dark coat from the back of my armchair, pulling it around myself like armor. I stopped at the door.Going out like this, in this dress, and not to the office… this had gone beyond an office affair or a strange work relationship. If I did this, I knew in my heart that I’d be a whore. There was no way I was dolled up like this for a dinner or a meeting. Mr. Smith meant to fuck me, which okay he’d done once already, no big deal… but on a weekend, and dressed like an expensive slut, and for a lot of money… like a LOT of money.I glanced at a pile of bills on my little end-table. In my mind, I could see four of those envelopes fade away and disappear from tonight’s “compensation” alone. There was nothing for it, this was still an incredible opportunity. I’d get through it.The car took me to the rich part of town and up to the drive of a huge house. The letterbox said “Smith” on it, and there were several very expensive-looking cars parked in front. We pulled around the back and I was ushered into the kitchen.The cook, a tall man in an apron with bleached hair, grinned when I entered. “Oh my god, you pendik escort much be Lucy! You look fab-u-lous!” I giggled despite my nerves. This was without a doubt the gayest man I had ever met. He bounced from one place to another in the kitchen, preparing food and mixing a drink at the same time as if there were three of him. “Thanks,” I said. “I, uh… really don’t know what I’m doing here.””Oh, honey, you’re the hostess!” He pulled off my coat and shoved a drink into my hand. “Here, down the hatch. It’ll calm you down. Damn girl, where did Smithy find you? Your boobies are just delightful!”I blushed and drank the cocktail he’d handed me, perhaps a bit too quickly but the gentle burn in my gut killed some of the butterflies. “So… what do I do?”He giggled at me. “Well honey, first you take this drink in to your master. He’s hosting the poker game tonight. Then after that, he’ll let you know what he wants.I nodded, taking the glass he’d held out for me and walking up to the door. I took a deep breath and pushed it open.The room beyond was opulent. Artwork on the walls, a fish tank that looked to be full of huge piranhas, and a grand piano all caught my eye, but then I was distracted by the occupants.”Ah good,” Mr. Smith said, gesturing to me to approach. “Gentlemen, may I introduce Lucy, my new girl.”The other four men clapped their hands softly, as if I was a particularly graceful golf swing. Their eyes seemed to match that perception, as they slid up and down my body. The five of them – Mr. Smith, Mr. Evans, and three I’d never met – were seated on chairs around a high glass table, on which were coasters, drinks, chips and cards. They all wore very nice tailored suits. Expensive cigar-smoke cut through the scent of my perfume to sting my nose a little.Mr. Smith took the drink from my hands and smiled. “Lucy will be the hostess tonight. I’m afraid my driver was late, so the duties of taking coats and fetching drinks have been handled, Lucy, but you’re just in time for the first hand.” He gestured to the floor under the table. There was a large circular section of floor there that was cushioned, and the table itself was supported by a single brass pole built into the center. “Kneel down and get comfortable.”I stared at him for a few moments, trying to process the situation. Mr. Evans frowned and a couple of the others chuckled softly. Mr. Smith inclined his head. “Back to the center, Lucy. Now, please.””Yes, sir,” I replied quickly. I didn’t like the tone of his voice; it carried a threat. I knew that my behavior tonight needed to be perfect.I knelt down and turned, ankles on either side of the pole. It actually was pretty comfortable. The padding was a soft microfiber and very plush. Mr. Smith nodded and pressed a button on a small remote that I hadn’t seen on the table before, and the entire area started very slowly rotating. “Keep your eyes open, Lucy,” he told me. “Johnson over there likes to hide an ace in his sleeve, if you see it just let me know.”The men all laughed. Evans dealt the cards and they all anted in while I slowly spun around beneath them, watching their hands and giving them what was probably the best cleavage show I’d ever performed. I had to watch their hands, because otherwise my eyes kept landing on their laps where every single one of them seemed to be sporting a full erection.The men all talked and laughed and bet their chips, but their eyes were on me as often as their cards. I knelt, bent forward a little to steady myself with my hands, but not far enough to let the skirt ride up. The slow spinning made me feel lost and confused, and I had to fight a constant urge to stumble out from under the table and run into a corner to hide, but they all seemed to behave as if it were the most natural thing in the world to have a woman rotating around at their feet.At last they all showed their hands. The man who’d been called “Johnson” won the hand. Mr. Smith stopped my carousel as I came around to kartal escort face him. “Alright, Johnson, you know the rules. Half the chips into the pot if you want winner’s privilege.”The chips slid forward and Johnson smiled down at me, then reached down toward my breasts. “Hey now,” Smith scolded him. “No touching.” They all laughed and the hand drew back, going instead to his lap where he unzipped and pulled out his cock. It was bigger than Mr. Smith’s, and as I’d thought before it was standing at full attention.”Lucy,” Mr. Smith said to me, “Give Mr. Johnson a blowjob.”I turned back and looked up at him. He’d never asked me to do anything like that for someone else before. He was smiling at me, but his eyes were cold. “Yes, sir,” I said meekly, turning back to Mr. Johnson. I tried not to look up at him, instead focusing on doing my job. I wrapped my fingers around his shaft and stroked it once as I bent my head toward it. It was definitely bigger, but it twitched as I touched it and I knew that he wouldn’t take very long to cum. That was good, because my jaw wouldn’t take very long to lock up if I had to suck that thing.I held it and licked up the shaft once, but Mr. Smith’s voice stopped me with a scolding tone. “Lucy,” he said sharply. “I told you blowjob, not handjob. I’ve clearly been too lenient with you, and that is my fault. Hands behind your back, now.”I looked back at him. “S-sorry, sir,” I started. “Now, Lucy.””Yes, sir,” I said, putting my hands behind my back. I gasped as I immediately felt cold metal on my skin. He’d handcuffed me! I tried to pull my hands back but the cuffs held fast.”Stop that, Lucy,” Mr. Smith said. “Think of these as training wheels.” He put a hand on my shoulder and pulled me out from under the table to kneel on the floor. Mr. Johnson stood and moved in front of me, his cock an inch from my face. “Now try again, Lucy,” Mr. Smith said. “And do it right or I’ll let him use his hands.”I swallowed hard and whimpered out a “Yes sir,” then leaned forward. I had to clench my whole body to keep from falling face-first onto Mr. Johnson’s cock as I slipped it between my lips. It twitched again and I heard him moan, but he stayed completely still.I pushed down on it until it was halfway in my mouth, closing my eyes and trying not to think too hard about anything at all. I sucked hard as my lips moved back and then down again, slowly. I had learned that starting slow was a good idea, at least during my “dictation” sessions, and I thought perhaps it would be over quicker if I started with the slow teasing.The only sounds I could hear were my own heartbeat, Johnson’s heavy breathing, and the slurping sound as I kept moving my mouth up and down on his shaft. His hips twitched and I knew that he wanted me to take more of him, but I also knew that I would gag badly if I did, and I wasn’t sure how well I could pull back if things got bad. I took a little more anyway, forcing myself to breathe and suck and swallow around him, moving my tongue side to side.His breath hitched up and I decided it was time to go for it. I started bobbing my head up and down faster, sucking harder on him and making little moaning sounds to make my cheeks and tongue vibrate around him. He started moaning and having a lot of trouble not thrusting his hips at me. Suddenly he groaned and I felt a huge load of burning hot cum start spraying into my mouth. I pulled back a little so I wouldn’t choke on it, holding my breath and swallowing over and over. It tasted bitter and I felt my face tighten, but I managed to stay down until he was finished. I felt some of his seed leak out the corner of my mouth, trailing down my chin and dripping down on my breast.He pulled out of my mouth shortly after, to another brief round of soft clapping. I opened my eyes and saw Mr. Smith nod approvingly. “The washroom is over there,” he said, tilting his head. “Go get cleaned up. No, the cuffs stay on.”I nodded, coughing once and whispering “Yes, sir.” I slid one foot under myself and carefully got to my feet, once more thanking God that I’d practiced in heels so much before, and headed for the washroom. Behind me, the party guests took their seats once more and spoke in hushed voices.

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