The Gamble

by Alice Ward

  I hadn’t been with anyone in years. My last boyfriend only lasted a year, and I think Dwayne and I broke up because I just couldn’t let down my walls — they were tall and thick, and I knew when the first bricks were laid down.

  Nineteen years ago, my dad bludgeoned my mom with a tire iron. He hit her sixty-four times, at least that’s what the newspaper reported when I read it years later.

  He thought she was cheating on him, and from all accounts whispered behind partially closed doors, she was. At least that was what I thought I heard them say. I would sneak around the house after everyone thought I was in bed and listen, trying to fit the pieces together.

  I remembered them arguing in the car, me in the back seat. My hands were over my ears, my eyes tightly closed as they screamed at each other. In a fit of drunken rage, he drove us to a remote spot, killed her with the tire iron, then shot himself.

  I remembered the gun. The small, cold piece of steel pointing at me. My heart leaped into my throat, and I wanted to scream, but I didn’t. I just started to cry.

  “Please, Daddy,” was all I could get out.

  He turned the gun on himself, and I don’t remember anything else, just waking up in my gran’s lap. I didn’t even know where we were.

  Men… I didn’t really trust them, even nice ones like my ex. I think Dwayne just gave up and moved on.

  “Caitlyn!” Ma shouted.

  I groaned. Great, I was going to get a reprimand for being rude to the rich guy who was about to proposition me. She was waving his bill in her hand, trembling.

  “Whatever you did….” She couldn’t finish her words, just slapped the bill in my hand and looked at me expectantly.

  I glanced down to his signed check. Felt my knees go weak and the world around me turn dark as I read the note written on the top of the bill.

  Caitlyn, you look like a girl who could use… a little extra cash. Use it to change your life, have fun, whatever - KP

  Next to the “tip” line, he’d written $15,000.

  CHAPTER TWO

  KP

  I was expecting that whole thing to feel better than it did. I didn’t extend charity often, but she had me wanting to be a hero.

  Having successfully eaten at my first late-night greasy spoon, I was proud of my accomplishment. I wanted to hate it, but I didn’t exactly abhor the experience. I was out of my element in every way possible, yet I was no stranger to uncomfortable situations. They usually didn’t even register for me.

  Caitlyn was an unexpected surprise.

  Who knew one of the most beautiful women in the country would be tucked away in a dirty little diner? She had the most striking brown eyes and vibrant auburn hair. Her face was indescribable, and her body… even polyester blend couldn’t hide her incredible curves. Caitlyn was poetry, a symphony, and a masterpiece all in one. Frankly, I lost my shit. I never misbehaved in public. Shame on me. Now, I felt off-center.

  She’d jarred me, though, with her refusal. Well, she didn’t actually refuse. I pulled the reins before hitting her with my, “You look like a girl who needs a good fucking” line. She beat me to the punch, and what a punch it was. The feeling was unsettling. I had never been rebuffed. I was trying to pacify myself by insisting that she hadn’t actually denied me. She berated me, scolded me, and demeaned my base nature, yes, but she never really refused… because I never got the chance to ask her the question.

  Now, I felt challenged. I needed to win. Leaving her the money was only the start of my game. I would have that girl purring in my lap soon enough. I let the image settle my brain as I finished watching the weekly dailies on my phone.

  The drive back to New York City was tedious, yet it gave me an opportunity to finish my work. Driving at night meant I escaped the horrendous city traffic. I didn’t like people nosing around my private life, so the veil of night was a welcome deterrent to prying eyes. The drive from Connecticut to NYC had been uneventful except for the diner interlude.

  I couldn’t shake it. Why did this woman vex me? She was just like any other. That was my mantra all the way back to NYC — she was just like any other woman.

  I would be the first to admit that I loved women. No, that wasn’t true. I loved to fuck them. There was nothing better than a woman’s body in the heat of arousal. I was thirty-fours years old and by now an expert. I knew women better than they knew themselves. That was why I vowed that I would never marry one or otherwise commit to one. I liked variety and wanted to taste every flavor and often. I was also not willing to become intimate enough to let anyone near my heart. That was the chink in my armor, but I was up for a good old-fashion fucking any night of the week.

  Caitlyn was definitely high on the fuckable list. I’d thought that with even a whiff of my money and a sliver of my attention she would have spread her legs in the back seat of my Bentley. I was wrong. It didn’t happen often, which made her even more alluring. I could honestly say, I hadn’t seen so much natural beauty in a long time, and beauty was my business.

  As the head of my own film company, I saw gorgeous women at every turn. Sadly, many had been nipped and tucked here and there, and if they weren’t altered surgically, they were so hyper aware of their own looks, it was often a turn-off.

  But the graceful and well-composed little waitress from “bum fuck nowhere diner in the sticks” had me questioning everything. Somehow, nothing could compare to the feisty little waitress who was now fifteen thousand dollars richer because of her biting commentary on my essential needs. She could be even richer if she played her cards right.

  She was on my mind when I woke up the next morning, another first. I wasn’t sure what got to me more — the fact that she turned me down and scolded me or that she turned me down and walked away. I would win her at all costs. I never wanted to enter that god-awful place again, but I was considering it, if it meant a chance at convincing Little Miss I-am-not-here-for-your-entertainment to reconsider an indecent proposal. And hell, yes, she was here for my entertainment.

  Monday morning was chaos as usual. We had meetings back-to-back, notes on the dailies, lunch at my desk. Whining producers who wanted more, accounting and business affairs wanting us to give less. A typical day at the office.

  Passing by her desk, my assistant started to rattle off her list of calls. “Mr. Preston, Sheldon Drake is on line one, he wants an answer for his client today, Elizabeth Mulder is on line two.” But I couldn’t be bothered.

  No one pressured me, especially famous people who thought their farts should be bottled into a custom-made perfume.

  “No, no, no.” I couldn’t take this shit this morning. “Tell them all to fuck off.”

  “Um, well, I think you should probably deal with the Pitt thing, maybe… sir,” my assistant sheepishly added.

  “You can tell Brad to fuck off too. If he doesn’t want to be in a blockbuster movie — which correct me if I’m wrong, but it’s been a while — then he can suck my nuts,” I barked back at her.

  You could hear a pin drop; the place had gone deathly silent.

  Maybe I was overreacting a little, but I was off my game today. I needed a good screwing and a single malt scotch. My assistant was actually a lovely, capable young woman. I was an ass.

  “Tell Brad’s people to have him call me, and we’ll iron out the details,” I capitulated and stalked into my office to be mired in other shit, like production spreadsheets, for a while. Before I knew it, seven-thirty had hit me like a speeding train.

  Rachel slipped into my office wearing a long coat and carrying a large insulated bag. She was my assistant about three years ago, but with hard work and a good word from me, she now headed production at an indie film house nearby. She locked the door behind her and sauntered closer.

  “Am I early?” she asked as she opened the conference room adjacent to the office and started setting out a sushi smorgasbord.

  “Nope.” I tried to bite my irritation back. “Right on time.”

  “I bet you need to let off so
me steam after you blew up at everyone in the office today?” she playfully needled with a smirk.

  “How’d you find out?”

  Really, the gossip around this place was criminal. Couldn’t I have a good rant without it being headline news?

  “Your assistant’s ‘I wouldn’t go in there if I were you’ sort of tipped me off. They didn’t have any blowfish today,” she mentioned as she waltzed back into my office. “I’m going to have to be the only thing that blows tonight.” She smiled as she knelt down in front of me and unzipped my trousers. “This should make you feel better.”

  “Arggh…” I cringed.

  “I know, bad sex humor.” She laughed as she pulled out my soft cock, her lower lip stuck out in her signature pout as she started stroking me. “What? Not happy to see me?”

  “It’s been a rough day,” I lied, trying to relax.

  She tugged harder on my shaft. “It’s gonna get rougher.”

  I wanted to be there for her — our Monday night thing — but I wasn’t feeling it. Another first for me. Sex was easy. I had sex mastered. But tonight, sex wasn’t what I was into. I gently touched her, halting her assault on my flaccid member.

  “What about if we eat first?” I suggested.

  “Can’t we have an appetizer?” She pouted as she glided her mouth over me, her tongue edging around the rim of my cock.

  It felt good, she always felt good, and I was relieved when I started hardening in her mouth. Her moans, signaling her satisfaction with my response, had me getting even more rigid. Tingling sensations urged me to rut. Feral grunts escaped me as I thrust into her throat, but my mind was on my sexy little waitress. I was envisioning myself pulsing into her mouth as I held Rachel’s head and started quickening my pace. She resisted me, and her tongue swirled around my engorged head, playing with the ridge. Her hands replaced her mouth on my shaft and pumped me into a frenzy.

  I groaned when she pulled away and threw her coat to the floor, revealing her perfectly naked form as she laid down on my desk and spread her legs. I dove across her and gathered up my papers. “I can’t have us fucking on these.”

  Her hand found my erection and angled it into her tight center. I reached over to open my desk drawer and pull out a condom.

  “Don’t worry, baby,” she purred. “I got the NuvaRing last week. No babies for us. You don’t need your raincoat today.”

  “Better safe than sorry.” I grabbed the condom and rolled it on.

  I needed this, this would help. Her muscles constricted around me as soon as I entered, and I felt a tightening in my gut.

  Pumping hard and fast, I growled, forcing myself not to come.

  “I’ve been doing Kegel exercises,” she boasted as she spread her legs out farther, giving me room to dive in deeper.

  “They’re working.” I tried to control myself, but she really had been honing her skills.

  Soon, I was lost in the sensations, and we found the rhythm we had become accustomed to. I stopped all my worrying and second-guessing and just let myself enjoy what she and I had. She climaxed several times before I did, and when we were done, we had a raw fish feast. She was smart, funny, beautiful in an angular kind of way. I loved that she was just in this for the sex and nothing more.

  “Why do you come here each week?” I was curious, we could have stopped this a long time ago.

  She shrugged, swirling a finger through my chest hair. “I like fucking you.”

  “Do you ever want more than just this from me?” I hoped the question didn’t open a can of worms because I certainly wasn’t going to give her more.

  “Nope. I don’t need you as anything but a distraction. You’re perfect.” The truth was refreshing. “The stuff doesn’t hurt either,” she said as she admired the diamond tennis bracelet I gave her for Christmas.

  This made me laugh, and right now, laughter felt good. I couldn’t help but think of “Caitlyn, the refuser of desirable rich men.” Why could Rachel so easily agree to this and not Caitlyn? The answer was simple, of course, but I felt daunted. Every little girl had a dream that her prince would show up on a white horse, and yet Caitlyn’d slugged both horse and prince in the face before the prince could even say, “Hello, my name is Charming.” I had to know more.

  After Rachel left, I called Ma’s Diner in Connecticut and found out that Caitlyn the Prince Slayer’s name was Ashcroft. A quick Google search told me she was twenty-four, lived with an elderly relative, and had some limited success as a painter. I sat back in my desk chair and pondered my next move. Just then I got a text.

  I love love love catfish. You did it!

  Smiley faces filled the rest of the screen all the way down to the bottom. I couldn’t help but laugh. If he only knew.

  CHAPTER THREE

  Caitlyn

  That was definitely the craziest thing that ever happened to me. It took a fair bit of time to recover brain function after looking at the amount of money he left. The asshole gave me a fifteen-thousand-dollar tip. What kind of insane madman does that? I didn’t care how much money you had, you don’t just give it to a complete stranger like that. I’d read stories on Facebook that were similar. There was one I remembered about a kindhearted patron who had left a woman with a bunch of kids and a great backstory a hefty amount. That guy was a hero. Their story deserved to go viral cause it made everyone fuzzy and gushy and restored their faith in humanity. But this guy… this guy nearly propositioned me, and I verbally bitch-slapped his inappropriate ass back into its place, then he gave me an ungodly amount of money. This was not Upworthy compatible.

  After the delirious haze of shock had settled around me, I realized I actually had to do something, like move, or talk to all of the shocked and surprised faces surrounding me. The first person to pierce my bubble, of course, was Ma.

  “Well, I can’t cash that out tonight, hope you’re not expectin’ it right away!” she growled in her usual Ma manner.

  “No, of course not, Ma.”

  I could tell she was irate with jealousy. I understood, I certainly would have been. I had to think fast. Even though I desperately needed the money, it wasn’t mine. I’d done nothing admirable to get it and frankly, it felt wrong to take it. Someone who clearly had more than they needed dangled a morsel in front of a person they assumed was starving, what a petty little game. While I wanted to be righteous and incensed, I had to admit that his gesture had my imagination fired up. The way his eyes looked at mine and then that crazy unspoken connection… it was hard to ignore.

  I was smart enough to know I wasn’t falling for him exactly, no matter how devastatingly gorgeous he was, but I was going down hook, line and sinker for the fairy tale. The idea that someone waltzed in, swept you off of your feet, and made your life happily ever after. That idea was hard to resist. Happily ever after was a free pass forever, inspiring a lifelong motto of “no worries… always be happy.”

  “What makes you happy?” he’d asked.

  Seeing people filled with joy made me happy, it was still love, but a different kind. I could have given all the money to Gran, but it wouldn’t have made her happy. She never put much value on money, which was why she always just had enough. She would have made me give it back or possibly done something stupid with it like buy a collection of ugly dolls on QVC, just to prove money was momentary. I absolutely needed the money for school, but did I want to earn it this way? It wasn’t enough to change my life forever. I was going to share with Linda, but again… that was just two of us. As I looked at all those shocked and jealous faces, I realized that this money would only bring me their scorn and envy, so I did what made me happy.

  “Since there were seven of us working tonight, not just me, I want to split the money. Two thousand for each of us, and then we can donate the last thousand in the restaurant’s name to the Youth Center for the Arts. Okay? That way it’s fair for everyone.”

  The shocked and astonished faces slowly morphed into joyful looks of wonder. See, that was happiness.


  When I got home, it was nearly three in the morning. Gran had fallen asleep to the TV. An episode of Locked Up was blaring a jarring story about a man’s meth addiction causing him to have an altercation with a prison guard. Bless Gran’s heart. She had a few pen pals in prison, people who the church referred before our scandalous disbarring. She had a massive heart, and I think she watched shows like these to dig a little deeper into humanity, trying to sieve out the infinite truth of existence, especially for those who struggled.

  “I don’t know how you can sleep to that, Gran,” I whispered in her ear as I tried to rouse her.

  “Hmmm,” she said in a sleep-glazed grog.

  “You have to go to bed,” I told her more loudly.

  “Right, right. Just making sure you got home okay.” She stood up and headed to her bedroom down the hall. “You have a good night, kiddo?” she asked as an afterthought.

  “Better than most. I’ll tell you all about it tomorrow. Sweet dreams.”

  “Night, dear heart.”

  I was too wired to sleep. Ironically, I understood why the star of My Fair Lady sang about wanting to dance all night. I shouldn’t have been feeling the way I did about my Professor Higgins because he was nothing more than a moneyed bully. Well, to be fair to ol’ Eliza Doolittle, her Professor Higgins wasn’t too different than mine. He was simply a rich player who liked to toy with people. Despite this fact, everyone at the diner tonight night went home with a tiny piece of happiness.

  Michael, the thirty-five-year-old dishwasher with five kids, burst into tears when we told him the news. I got a hug from Linda, and even more shocking, from Ma as well. It felt amazing. So, in addition to his virtuosity as a flirt and an indecent proposer, the rich dude tonight made magic. And despite my wanting to hate him for everything he stood for, I found myself fascinated too. Why me? As I stared at the TV, all I could think of was that man. I didn’t even know who he was. I remembered how soft and subtle his lips looked but didn’t even bother to find out his name.