Billionaire's Bet (BBW Waitress, Billionaire Seduction)

  Billionaire's Bet

  By Moira McGuinness

  Copyright 2013 Moira McGuinness

  All Rights Reserved

  Billionaire's Bet

  Book Design by Moira McGuinness

  'It is way too early for this', my cat Delilah said to me with her eyes. 'What are you doing'.

  "I know princess", I said to her quietly. "Mommy got a job, I have to leave early".

  'Get back to bed. It's warm here. You don't want to go outside do you?'.

  "It's only for a few days", I told her. I just need to make some money for cat food, okay?".

  Grumbling as only a cat can, she jumped down from the bed to rustle in the litter box. When satisfied, she jumped back onto the bed.

  ‘I’ll just wait here for you then. You need to know that I’m not happy about this though’.

  It was the end of a rather long and painful month. June had started well enough - my boyfriend and I were planning a trip to Iceland, he had just been promoted at his work, I had reached the 5 year mark in my job at a bank, and we were talking about our future together.

  Apparently this was a bad idea for him. Talk of the future had scared him, the thought of being with one person for the rest of his life filling him with dread. He cooked me dinner, poured me a glass of wine, and broke my heart. Two years we’d been together - not an age but long enough to feel lost without him.

  My week only went downhill from there. Going to work the very next day I was greeted by my supervisor at the door. Carrying my personal belongings in a box he told me that there were cutbacks, and that I was the first to go. They did give me a generous severance package, meaning that I could support myself and Delilah for a few weeks at least; but again the sense of loneliness stung. I spent most of my days browsing personal ads and job postings - neither of which filled me with any hope - and talking to my cat. When she began to answer back, I knew that I needed to leave the house and meet real, human people.

  Finding myself at the mall, I had been walking through a department store and was trying to navigate my way around the perfume counter without being sprayed. As I hid like an escaping prisoner, watching the guard walk around the watchtower so that I could time my run, I felt a tap on my shoulder. Standing guiltily I had come face to face with a stern looking man, who had given me an envelope. Not saying a word to me he had simply turned on his heels and walked out; lost among the linens.

  Scurrying I had quickly found my car, and in the sanctuary that it provided had opened the envelope. Inside was a simple sheet of paper.

  I have chosen you to do a few days work for me, from Thursday thru Saturday of next week. You will be waiting tables at a private function. The hours are 9am until 9pm, for which you will be paid $40 an hour. You must wear a black skirt, black shoes, and a white button down blouse. If you wish to be employed please email me at jhovens@bestfunctions.com. The address of the function will be provided by reply.

  Thanking you,

  Joseph.

  Crumpling up the paper and tossing it behind my head I’d scoffed, almost outraged that someone would just walk up to someone in a mall and give them something like that. Who did they think they were? Who did they think I was? Did I look like the kind of girl who would just take a risk and email someone that I didn’t know? Of course I was, but he wasn’t to know that! Did I look like the kind of girl who needed money? Of course I did, but surely it wasn’t that obvious? 12 hours for 3 days, that’s 36 hours, at $40 an hour - that’s nearly $1500! Did I look like the kind of girl who would rush home, boot up her laptop, ignore the meows of her cat while she emailed this man to tell him she’d do it?

  Clearly.

  And so here I was. Dressing in the uniform that was requested, getting into my car, and driving to a place called ‘Graycastle Manor’.

  My arrival told me that this was no normal job and that this was no normal place. At the gate I was instructed to step out of my car and stand against a wall. Both car and I were searched - for weapons they said - before I was allowed to enter the building.

  This property was insane! Absolutely huge, the most opulent building I’d ever stepped into. According to the posters that were displayed in the foyer, Graycastle Manor was to be the setting for a ‘Managing Wealth’ conference, attended by the wealthiest people in the land. A millionaire would have been laughed out of this place. Looking at the schedule I could see that the lectures were basically divided into three subjects, making more money, keeping more money, and spending more money. The mega rich swanned past me, gliding across the marble floor. Clearly I was in a different world - a world where helicopters landing on the roof was the norm. A world where it was quite acceptable to spend tens of thousands of dollars to attend a conference, a world where anything could be bought.

  Quickly I was approached by a man who introduced himself as ‘Wesley’, and who was dressed in a very smartly cut suit. He was an older gentleman, thin and a little frail, but he had kind eyes and he introduced himself by shaking my hand softly.

  “You must be Hazel”, he said mysteriously. How did he know my name? “I’ve been expecting you. Please, follow me”.

  Wesley lead me down one of the hallways towards the kitchens. Along the way he spoke to me about my duties and expectations. I was to mingle among the billionaires, take their drink orders, and fetch whatever they wanted.

  “It’s always amazed me”, he said with a whisper, “how much these men drink. To think that decisions that can affect millions are made when they’re drunk on whiskey”.

  Looking to my left I spotted the chairman of the bank that had employed me, Alan Starkey, schmoozing with a group of older executives. I recognized him immediately, his face had been plastered on a poster that had faced my desk for 2 years. Not that that was a bad thing; I had always found him attractive, if just a little pretentious for my tastes. Once when stuck in the office late and alone at night, I’d allowed his fixed eyes to watch as I’d toyed with myself. I had kept a thin vibrator in my purse for those moments when the mood struck and I had some privacy, and I had fallen into a fantasy while staring at his face. Ever since I had felt that we’d shared something, even when he had come to our branch on a site visit a week before my redundancy to give a pep talk to the nervous staff, I had allowed my mind to drift back to that night of one-sided lust. ‘We are all tightening our belts’ he had said with a sympathetic look, causing me to look at his belt for signs of tightening. Looking up to him I’d only then realized the seriousness of his words. ‘Cutbacks may hurt us all’, he’d said.

  Apparently. When I walked past him I overheard him boasting about the new yacht that he’d commissioned. I silently hoped that he could only afford the 40 ft one, not the 50 ft. Cutbacks hurt everyone. As cute as he was, I couldn’t help but feel that his mismanagement of the bank had caused my current predicament.

  I hoped to catch his eye as I walked past. He did look at me and seemed to smile, but then quickly went back to his conversation. He probably wouldn’t remember me - he was a very rich and powerful man and I doubted that he’d recall the shy, plump girl that worked as a teller in one of his banks. Still, I had hoped that he would break off his chat to come and see me, to maybe ask why I wasn’t at the bank. Hiring and firing are well below his level, for a fleeting second I’d dreamed that he’d find out about my termination, get on the phone, insist that I be rehired and double my salary.

  Dreams are meant to be broken. I followed Wesley into the kitchens to be shown where the drinks were prepared. He told me that the majority of the girls who worked there were repeat employees, hired every year for this 3 day conf
erence. While he introduced me to the head chef one of the girls burst into the kitchen, her face as red as crimson.

  “Anyone here got more panties I can borrow?”, she called to the room. “I’ve run out already”.

  Wesley chuckled, turning to me with a wry smile.

  “I’m sure that you’ll have a profitable time here”, he said.

  For the duration of the morning I wandered throughout the halls of this giant residence, watching the patrons as they gave me a nod or a wink. Most ordered whiskey, some vodka, none anything non-alcoholic. Approaching noon I headed up one of the staircases to find a bathroom.

  Walking along the corridor I heard voices from one of the bedrooms. I had no intentions of looking inside but the door was ajar and the snippet of conversation that I heard piqued my interest.

  “Try to rub them into your pussy a bit for me”, a male voice said. “I need to be able to smell you”.

  “Of course”, said the girl, giggling. What on earth was going on in there?

  My heart pounding, fearful of being caught but dying to know what was happening in the room, I poked my head around the door. The man was standing with his back to me, the girl facing him. Rummaging underneath her skirt she wiggled her hips, pulling her black panties down. Curling them into a ball she handed them to the man, who appeared to be giving her cash in return.

  “A pleasure doing business”, he said.

  “Likewise”, she said with a smile. Leaning forward to kiss his cheek she looked over his shoulder, catching sight of me in the doorway. I gasped as our eyes met, terrified that she would reveal my presence to the man and have me fired. Instead she winked at me as she pulled his cheek to her lips.

  After scurrying downstairs I worked for the rest of the afternoon, trying to decipher what I’d seen. When I went into the kitchen to fix a scotch on the rocks for a younger billionaire - who had curiously smiled at me when I had asked him which brand, simply saying ‘whatever you think I’d like’ - I ran into the girl who I’d seen upstairs.

  “This is your first year here, right?”, she said to me, smiling. “I’m Megan, nice to meet you”.

  “Amber, and yes it is”, I said nervously. “I’m so sorry about before, I was looking for a bathroom. I hope I didn’t interrupt anything”.

  “Not at all”, she said taking my hand. Walking me over to the kitchen door she stood, pointing to the throng of businessmen. “You see all of them? Do you know why they come here?”.

  “For the conference, right?”, I said meekly.

  “Partly”, she said. “They like to have some fun too. You see that man over there? The super cute guy with the pink tie?”.

  Following her gaze I saw that she was talking about Alan Starkey. Talking with a couple of older men, he looked towards us and raised his glass.

  “I see him”, I said; preferring to keep my knowledge of him close to my chest, for now.

  “Every year he makes a little bet with his friends. Whoever can collect the most pairs of panties from the girls who work here wins. That’s why so many of us come back, once they let you know that they’re playing, they’ll pay big money for the goods. A girl can make a lot of money if she plays her cards right”.

  A little shocked, I put my hand over my mouth.

  “That’s incredible!” I said. “How much do they pay you?”.

  “The average is $1000 per pair”.

  Letting out an audible gasp I looked into the eyes of this girl, who beamed back at me with her eyes wide open.

  “Holy fuck!”, I exclaimed. “But how do you know that they want to buy?”

  “There’s a code”, she said. “It’s part of the game. They aren’t allowed to just come up and ask you, they have to let you know via the code. That way if they’re overheard by someone not playing they won’t lose face, and if they’re asking a waitress who’s new they won’t be slapped in public for offending her. Listen...” she said, pulling me closer to her. “If one of these guys asks for a scotch on the rocks, and tells you to choose the bottle, then you’ll know. Tell him you’re going upstairs to find a bottle because there’s none in the kitchen. He’ll follow you, you’ll take it from there”.

  I scanned the room, looking for the man whose drink I was supposed to be fixing. Standing, with both hands in his pocket, he looked directly at me with a sheepish grin on his face.

  “But I only have one pair”, I said to Megan. Remembering the girl that had asked to borrow panties this morning, I suddenly realized why one might bring more than she was wearing to work. I was still a little disturbed by this whole thing, but couldn’t stop thinking about the money. $1000 for each pair! I said to myself. That’s a lot of cat food!.

  “I have more”, Megan said grinning at me. “I’ll go get some. I’ll meet you back here in an hour”.

  Feeling so nervous that my stomach started to growl, I walked out into the hall to approach the man who was waiting for his drink. He smiled as I approached, and rocked on his heels in what seemed like boyish excitement.

  “I’m... I’m sorry”, I said to him. “We’re all out of scotch downstairs. I’ll have to go upstairs to get some more”.

  “Oh no!”, he said in mock anguish. “Shall I come with you to look?”

  “Sure”, I said. Turning to walk up the stairs I felt him behind me. As I walked up the stairs I noticed that he walked 4 steps behind, his face at my ass level, clearly inspecting the goods. I felt so dirty. A little sick, a bit nervous, and quite turned on.

  Watching the exchange between Megan and her ‘customer’ had excited me. Always a bit of a voyeur, I’d been witness to an exchange of the most personal nature and had felt my pussy tingle as I’d watched. Now it was my turn, and the knowledge that my panties were soon to be in the hands of this man turned me on, just a little. I was turned on for knowing that he was currently looking up my skirt, for knowing that he would soon be able to smell my scent, and for knowing that soon, and for the next hour at least, I would be walking around this fine building without panties.

  At the top of the stairs I went into one of the bedrooms. The man followed, closing the door behind him. For a second I worried that this was all an elaborate hoax, a trick played by Megan - getting back at me for interrupting her earlier. What if this guy just really wants scotch?

  My concerns were allayed when he pulled out his wallet. He took out a small wad of cash, clearly already prepared with the right amount of money for these transactions.

  “How long have you been wearing them?”, he asked matter of factly. He’d clearly done this before, his manner more business than pleasure.

  “Since this morning”, I told him. “You’re my first”.

  A generous smile broke out over his face. Still nervous, my breathing quickened as I pulled up my skirt over my ample thighs. Sliding down my pink panties I exposed my pussy, freshly shaven and glistening in the light of the room. I could feel his eyes on my flesh, my face slightly flushed I felt myself getting more aroused by the intimacy of the situation. I noticed a growing bulge in his pants, his excitement as clear to see as mine. Filled with confidence I lost my anxiety, deciding to put on a little show for my customer. Turning away from him I pushed my bare ass out towards him, bending to roll my panties down my calves. Hooking them over my heels, one by one, I stood and faced him. Walking towards him I held out my panties, as he flashed his cash in my direction.

  “Thank you”, he said. His voice shaking. Gulping, he turned to walk out of the room.

  ‘A pleasure doing business with you’.

  Going back downstairs I went through the kitchen and out of the back doors. Seeking clarity of mind that fresh air might bring I stood against the brick wall, wishing that I had my cigarettes with me. Hearing a man’s soft moans I looked to my right, to see Megan kneeling, her heeled shoes pointing behind her. Her head in the groin of a suited man, his cock in her mouth.

  Hiding behind a pillar I watched intently as he sucked on him. His hands on the back of her head guided h
er, her hand on his thick shaft stroking him, guiding him into her mouth. His pants around his ankles he leaned over her back to rub her naked pussy with his finger. Spreading her ass cheeks wide, he slid his meaty digits into her snatch, prodding her roughly as she sucked on him. I watched - my own pussy drenching - as she took him whole, deep throating his thick cock. Standing and bracing himself against the wall he put his fingers into his mouth, tasting her juice. Sending him over the edge he pulled her head into his crotch, shuddering as he sent her cum into her mouth.

  Quickly rushing into the kitchen, eager to not be caught again, I stood in a corner and attempted to catch my thoughts. My head told me to calm down, to simply put my head down and get through the day, get paid, take my $1000 and go home. My heart told me to run, to escape this madhouse of depravity, of rich men taking advantage of young girls. My pussy told me to find a bedroom upstairs, to give it the attention that it sorely deserved.

  Basically running I took off down the hallway, heading for the central staircase. Rapidly ascending I bounded up the stairs, my mind unable to get itself out of the gutter. My pussy yearning, almost audibly screaming for my fingers, sent a single rivulet of its potion down my leg.