The Christmas Gamble

by Sienna Ciles

  My friend Joana had been there for me throughout the whole ordeal, and she’d been hounding me relentlessly over the past several months to start “getting back out there” and enjoying the single life. Apparently, to Joana, that consisted of dating multiple men with no commitments or complications.

  Personally, I’ve never had a “friend with benefits” kind of thing before, and honestly, I really didn’t see the point of it. I told Joana that when summer finally came, I was already planning to leave the city and go back home to the country where I truly felt I belonged. She told me that she was determined to change my mind. I was guessing the blind date with this “Martin” character must be part of her elaborate plan to try and keep me from leaving the city.

  I sighed as I turned into the small parking lot of my apartment building and pulled into my assigned space. Turning the car off, I headed up to my second-floor unit to get ready for my date. When I opened my front door, I almost screamed in surprise when I saw my bestie Joana seated comfortably on my white leather sofa. Her feet were propped on the ottoman and she appeared to be watching something on the screen of her smart phone.

  “Joana! Girl, what the hell are you doing here?” I demanded.

  Honestly, I shouldn’t even have been all that shocked. Joana did things like this on a regular basis. One night, she popped up in the backseat of my car and had nearly caused me to run off the road and into a ditch.

  “I’m here to help you get ready for your date,” she replied excitedly as she hopped off my sofa and turned around to face me.

  “Um, I appreciate the offer, Jo, but I’m quite capable of dressing myself for a date,” I replied with a frown.

  “Oh, puh-lease!” she said, rolling her bright blue eyes at me exaggeratedly. “If it wasn’t for me and my A-1 hair and makeup skills, you would never have gotten past your first date with your ex!”

  I knew there was no talking Jo out of anything once she had her mind set, so instead of wasting time in an unwinnable argument, I reluctantly agreed to let her play Barbie with me and dress me up for my date.

  An hour and about three trial outfits later, she had me all dolled up in an asymmetrical lavender-colored knee-length dress with matching stiletto sandals.

  “Jo, it’s April in fucking New York! It’s not warm enough for this outfit yet. I’m going to freeze to death in this!” I complained.

  She had my long brown hair done up in a neat little bun with two wavy locks hanging loosely down on each side of my flawlessly made-up face. The lavender eye shadow she’d picked out for me made my brown eyes pop and she’d outlined my lids with a dark eyeliner to accentuate their almond-like shape. My lashes were so caked with mascara that they almost looked fake and she’d covered my lips in a shiny, shimmery lavender gloss that made them appear three times plumper than they actually were.

  Even if I’d wanted to complain, I couldn’t have. She had truly dolled me up like a goddamned movie star. I couldn’t deny the fact that I felt sexier and more attractive than I had since I’d broken up with my ex.

  “Jo, you’re a fucking miracle-worker!” I exclaimed, as my eyes lit up at my own reflection in the full-length mirror on my bedroom closet door.

  “See? You look like a million bucks, Holly! Thanks to me, you just might get lucky and get laid tonight!” she said jokingly.

  “Yeah, right, Jo. There’s no way I’m sleeping with some random stranger on our very first blind date.” I narrowed my eyes at her. “And I’m taking a sweater just in case the temperature drops tonight while we’re at the restaurant.”

  “No, Holly,” she said. “If you cover those great tits of yours with a sweater, how’s he gonna be able to see how hard your nipples get when you’re cold?”

  I reached out and slapped her playfully in the arm, and both of us burst out laughing.

  “God, Jo, you are such a fucking whore!” I joked.

  Looking and feeling sexier than I had in long time, I headed out to the Lovehouse restaurant to meet Mr. Martin Langley for our blind date.

  Chapter 3

  Alex

  “Thank you again for meeting with me on such short notice,” the short, stout, GameTime Inc. marketing rep said with an enthusiastic grin. After wiping his grubby right hand on his white cloth napkin, he offered it to me.

  “Certainly,” I replied, reaching out and giving his hand a quick, firm shake.

  The Lovehouse had always been one of my favorite restaurants. The food was spectacular and the atmosphere was very stylish and elegant. The quiet, laid-back environment made it a perfect spot for business meetings and social gatherings alike.

  On a Friday evening, however, I would much rather have been romancing a beautiful young woman instead of sitting here with this chubby, balding, and implausibly annoying middle-aged marketing agent. For the majority of the meeting, I had been able to focus mainly on my delectable meal while tolerating his insufferable rantings and ravings about his company’s extraordinary first-quarter earnings and the obviously embellished projected earnings he was expecting for the remainder of the year.

  Unbeknownst to him, his inflated marketing banter was all but being wasted on me because I had no intention of investing in whatever it was he was attempting to impress me with. In fact, the only reason I had even agreed to this arduous congregation was because my father had pretty much demanded that I do so. Apparently, Mr. Stubby Balding-Head here was the nephew or cousin or something of one of my father’s business associates, and my father owed the guy a favor.

  I looked down at the gold-plated Rolex on my wrist and saw that it was almost eight o’clock. The client representative sitting across from me had finally signaled the waitress and asked for the dinner bill—much to my relief.

  “Well, then, you have my card. If you have any questions or concerns, please feel free to contact me at any time—day or night,” he said eagerly, standing up to finally take his leave.

  “Will do,” I said with a nod.

  With one final, yellow-toothed grin and a weird army-like salute to the forehead, the annoying man finally picked up his briefcase and went on his way. After he left, I went back to the men’s room for a moment, and as I was making my way back over to the restaurant’s main bar, I noticed a lovely young woman seated at the far end of the counter, alone.

  She was a pretty brunette who appeared to be in her late twenties with amazingly alluring eyes and pouty lips. I was certain that I’d never seen her here before.

  Sitting with her legs crossed on one of the corner bar stools, she seemed to be looking around uneasily, and she kept pulling out her phone and looking down at it as if she was checking the time. Being a thoroughly experienced man, I recognized the situation I was observing immediately. This appealing young lady had obviously been stood up by someone, though judging by her outward appearance alone, I could not for the life of me understand why anyone would have stood up someone as enchanting as she appeared to be.

  My mind immediately switched into charmer mode and I headed straight over to the empty bar stool directly to her right.

  “He’s a fool, whoever he is,” I said casually, leaning against the bar and looking directly at her.

  “Excuse me?” she replied, looking up from her phone and eyeing me with a questioning expression.

  “The idiot who stood you up,” I explained, raising my arm to signal one of the bartenders.

  “Oh,” she said quietly. “Is it really that obvious?”

  She picked up her phone and slid it into one of the outside pockets of her lavender-colored purse. That’s when I noticed her shoes, dress, and purse were all the same shade. Whoever this woman was, she had obviously put in a bit of effort to look nice for some nitwit who hadn’t even bothered to show up.

  No sense in letting such a lovely get-up go to waste, right? A slight grin began to play at the corners of my mouth.

  I could tell right away that this woman was definitely not just some average bar fly. She had poise and class, and though her sho
rt-length dress certainly had sex appeal, it was in no way tasteless or trashy. Her earrings, necklace, and bracelet set added a nice touch to her overall look but they weren’t gaudy. Something about her was intriguing to me, drawing me to her.

  “I must look pretty pathetic,” she said with a deep sigh, closing the zipper on her purse.

  “Not at all. In fact, you look absolutely beautiful,” I told her with a smile.

  She looked up at me and smiled back for a moment. There was a shyness in her smile, as if she was somehow unaware of exactly how stunning she truly was. This intrigued me even more, because most women as attractive as she was were snobbish and conceited. Either that or they often tried to use their striking good looks to get whatever they wanted from men. Kinda funny how the moment that thought crossed my mind, an image of my flirty, blue-eyed assistant, Alicia, instantly popped into my head.

  As I immediately shook both the thought and the image from mind, the bartender finally appeared. She was a tall, curly-haired blonde and she flashed me a friendly smile as she asked me for my drink order.

  “What can I get ya?” she asked. I glanced down at her nametag. It read: Carrie.

  “Good evening, Carrie,” I said, returning her bubbly smile. “I’d like to buy this lovely lady a drink.”

  I turned my head to face the pretty Lady in Lavender. She glanced up at me and then lowered her doe-like eyes.

  “Um, I really appreciate the offer, but I think I’m just gonna just go home,” she said as she pulled the strap of her purse over her shoulder and stood up.

  But there was no way I was about to let this captivating, mysterious Lavender Lady walk out and leave.

  When she rose from the bar stool, I finally got a good look at her entire figure, and I damned sure liked what I saw. She had a petite frame but her hips were curvy and her legs were long and toned. She’d gone through so much trouble to do herself up tonight and I was determined to talk her into taking advantage of the evening.

  I immediately reached out and took her hand, firmly but gently, and she turned around and looked at me.

  “Stay,” I said with an inviting grin. “Come on, just for a little while. You obviously got dressed up hoping to have an enjoyable evening. There’s no reason that still can’t happen, right?”

  I was still holding onto her hand because she hadn’t snatched it away. I locked my eyes with hers and tried to hold her gaze but again, she looked away, shyly.

  “Oh, I don’t know…” she said hesitantly.

  “Well, were you meeting a boyfriend?” Her small, feminine hands were ringless, so I knew she wasn’t married or engaged, but I wanted to make sure she was completely available before I put the moves on her.

  She shook her head.

  “Listen, whoever that joker was who stood you up, perhaps it was fate. Perhaps you and I were meant to meet tonight.” I raised her hand to my lips and kissed the top of her wrist tenderly. Her hand was soft and smooth and a hint of a fruity aroma emanated from her creamy skin. “Stay—at least for a little while. Let me show you how a real man treats a lady who takes the time to get all dolled up for him.”

  A smile made its way across her face, and I knew I finally had her convinced.

  “Okay, I guess I could at least have a drink or two,” she said with a sigh. I let go of her hand and grinned triumphantly. She sat back down and placed her purse on the bar in front of her.

  “Excellent!” I said gladly, clapping my hands together in delight. “So, what’ll it be? You can have whatever you want, tonight, milady. Splurge and enjoy yourself.”

  Her smile widened. “I’d love a glass of white wine,” she said cheerily, and I could tell that her mood was already lightening.

  “This woman has class,” I told the bartender proudly. “A glass of your finest wine, please. In fact, just bring us the whole bottle.” I pulled out my black card and placed it on the counter.

  “You got it, sir!” Carrie said with a wink. She picked up the card, looking quite impressed. “Would you like me to open a tab?”

  “Absolutely,” I replied with an affirming nod. I then turned my attention back to Lady Lavender. “I’m Alex, by the way. And you are—?”

  “Holly. Holly Shaw,” she replied.

  “You know, Holly, I come here quite a bit, but I’ve never seen you before. Are you from around here?” I asked.

  “I’ve actually been here a few years. I’m originally from a small town down south. I moved out here after college and started teaching third grade at the local elementary school.”

  “A schoolteacher, eh? A very respectable gig, I must say,” I replied. “You must have a lot of patience.”

  “I guess,” she replied shyly. “I’ve always loved working with children, though. I think I’d like to have a couple of my own someday.”

  She was family-oriented. My dad would love that.

  Just then, Carrie arrived with our drinks. “Keep ’em comin’,” I told her.

  Holly gave me a small smile, like maybe she was warming up to the idea of spending more time with me.

  “So how do you like it out here in the city? It’s a big change from the country life, right?” I asked after taking a sip of my drink.

  “Yes, it certainly is,” she replied with a nervous chuckle. She took a sip of her wine. “I thought New York would be a nice place to finally settle down and have a family one day, but, unfortunately, my ex-fiancé and I didn’t work out, so…” Her voice trailed off.

  “Well, I’m sorry to hear that things didn’t work out for you the way you originally planned,” I said with sincerity. “I’m not seeing anyone, either. I feel like it’s been hard for me to meet the ‘right woman’ here in the city.”

  “What? A handsome, stylish, charming young man like you? I find that kind of hard to believe,” she replied with a giggle.

  After a few glasses of expensive white wine, Lady Lavender really began to open up a bit.

  “I really do love it here in the city,” she said as she finished off her fourth glass of wine. “There used to be this one little Italian bakery right down the street from the school I work at. They had the most amazing cannolis!”

  “You mean Sanello’s Sweetery? Yeah, I actually had them cater a couple of events a few years back.” I poured her a fifth glass.

  “Really? Oh, they were wonderful! But they closed down last year. I was so bummed,” she said solemnly. “The only other thing I’ve ever wanted to do other than teach is bake. I used to love making cookies, cakes, and pies with my grandmother when I was younger. I even used to fantasize about having my own bakery.” She giggled as she reminisced and I found her genuine zest for life very refreshing.

  Chapter 4

  Holly

  For a rich, handsome, playboy kind of guy, Alex sure seemed really down-to-earth. By the third or fourth glass of wine, I was damned-near putty in his hands. He really did show me a great time and he kept complimenting my eyes, my smile, and my legs, which made me feel sexier and more appealing than I had felt in quite a long time. He even bought me dinner—something ridiculously expensive that I can’t even begin to even pronounce but it was the most delicious, delectable meal I’d ever eaten.

  After my fifth glass of wine, we took a romantic stroll around Central Park. It was actually a pretty warm night for early April in New York but when he saw me rubbing my arms from the slight chill of the night air, he took off his suit jacket and wrapped it around my shoulders. He stopped to pick a flower out of one of the flower beds in the park and put it in my hair.

  “Was that corny?” he asked me with a grin.

  “It was actually really sweet,” I told him pleasantly.

  “There’s a spot in this city that I personally feel is one of the most amazing views of the entire area,” he said softly. “It’s absolutely incredible. I would really like to show it to you.”

  I was having such an enjoyable time in his company that I honestly wasn’t ready for our evening to end. The shy, sheltered p
art of me wanted to say no, but then the words of my best friend Joana suddenly crept into my head:

  You need to go out and enjoy yourself! Have some fun for once in your life, goddamnit!

  Before I even had a chance to answer, he was already leading me toward the front of the restaurant.

  “Black Rolls Royce,” I heard him tell the valet standing just outside the entrance.

  Holy shit! This guy must really be loaded. Black card, $500 bottles of white wine, $150 dinner, and he drives a black Rolls Royce? This is almost too good to be true.

  In the back of my mind, I was thinking about how Joana would be reacting if I’d told her about Alex. She would be in my ear telling me to take a chance and that this could possibly be a once in a lifetime opportunity.

  The valet pulled his car up and handed him his keys. Then he opened the door for me and I climbed into the passenger seat.

  I had never in my life been inside of a Rolls Royce. It was quite impressive. He had a customized leather interior with all of the bells and whistles you could imagine. It was almost like riding inside of a mini-limousine.

  “Are you comfortable?” he asked, glancing over at me with his deep, seductively captivating blue eyes. I nodded and flashed him a warm smile. He stepped on the gas and we were off into the night.

  Less than fifteen minutes later, we pulled up into the parking garage of an incredibly fancy, glamorous-looking high-rise building. I was completely and totally astonished when I saw it. It was so tall—I mean, it looked like there were literally like a hundred fucking floors, at least. Standing outside the front of the building, I couldn’t even see all the way up to the top floor from the ground.