The Christmas Gamble

by Sienna Ciles

  “I don’t want a trophy wife,” Dean said, looking over his cards. “I’ll raise you ten.”

  I threw in chips to match his bid. If I lost this round, I would have to take off either my bra, my panties, or my sweater. Bra—at least then you’re still covered. Dean was down to his dress shirt and boxers, and I’d gotten a chance to see his surprisingly toned legs already.

  “Why not? I thought all billionaires operated like that,” I said. “You’re good looking and have a ton of money. You could have anyone you wanted.”

  Dean snorted at my comment and shook his head. “The problem with having a ton of money is that most women who’ll go out with you only do it because they want you to buy them the moon and stars. I like being generous but I don’t like being someone’s endless ATM.”

  I nodded. I could understand that point. I didn’t think I would like it any better.

  “So why not get on a dating site and just not mention being rich?” I put down another card into the community pool and Dean nodded to himself, glancing from the pile in the middle of the table to the cards in his hand.

  “I’ve mostly just figured that the right woman would come along eventually, one way or another,” Dean told me. “Can we change the subject?”

  “Sure, what would you be doing if it weren’t the holidays, and if you weren’t busy with business stuff?”

  Dean looked at me sharply for a moment and then chuckled. “Probably headed for somewhere, anyway. China, Japan, Singapore... somewhere in Europe, maybe? I’ve got a whole list of places I want to see before I’m too old to really enjoy myself.”

  “I do, too, actually,” I admitted. “Of course, I don’t have nearly the resources you do.”

  I threw in a couple of chips for my raise, and looked at Dean speculatively. He tossed in a couple of chips to see my bet.

  “If money were no object, where would you be spending the holidays?” he asked.

  I had to think about that one. On the one hand, I did want to see my family. On the other hand, I wished that I had a way to spend the holidays with them without having to be around them constantly, reminded of my newly-single status.

  “If money was no object, I’d probably get my family to come with me somewhere else. Hawaii or something—somewhere warm. And that way, I could be with them but also go off and do my own thing now and then.”

  Dean chuckled at that, and I couldn’t resist a little smile in return.

  It was time to show our hands. I had a flush but Dean had four-of-a-kind.

  “Pay up,” he said with a little grin. I rolled my eyes and reached around to my back, unhooking my bra through the fabric of my sweater.

  I wriggled around a bit and got the straps down my arms without showing anything and then pulled the whole thing out from under the front hem. I showed it to Dean with a little flourish and he wolf-whistled, and we both laughed. I would never have thought that I could be that comfortable in next to nothing with someone I’d only known for a few hours but there I was: eating room service food, tossing my clothes aside when I lost, and almost forgetting that the whole point of the long, rambling Hold’em tournament was to decide which one of us would get the master bedroom.

  It almost didn’t matter, anyway. The second bedroom was better than my bed at home. I would have gladly taken it if Dean had just insisted that as the person paying for the suite he should have the master. But I had to admit that this method was better. It was more exciting, and I could feel the little tingle I’d been getting around Dean starting to intensify.

  I managed to win the next hand, which stripped Dean down to his boxers, and things were starting to heat up between us in other ways. Instead of just pretending to get to know each other as strangers forced together by weird circumstances, I could tell that Dean was actually flirting with me, and I found myself flirting back.

  “Okay,” I said as I shuffled the cards. “So, the next hand, either you’ll be naked or I’ll be down to my panties. Can you handle that?” I raised an eyebrow at him with a little smile.

  “I have seen naked women before, Kayla,” Dean said. “I’m single, I’m not a virgin.”

  “Oh, so you’re a good-looking billionaire and you’re here with me a night or two before Christmas, without a girlfriend or a wife,” I pointed out. “You may have seen a woman naked before but this doesn’t speak well for you that you don’t have a naked woman in your company right now.”

  Dean laughed. “Well, with any luck, I’ll have a naked woman with me in the next twenty minutes,” he countered.

  I dealt out our individual cards and set the rest of the deck down.

  “Ante up and we’ll see,” I said. I threw in the buy-in amount we’d agreed on a couple of hands before—it was the max amount that we both had in chips—and sat back from the table, sipping from a bottle of water from the kitchenette in the room.

  “I think I’ve got a pretty good hand, here,” Dean said, looking from his cards to me as he tossed his chips in. “Gonna be hard to beat.”

  “Well, you haven’t even seen what cards are in the flop, the turn, or the river,” I pointed out.

  Dean shrugged. “So, this hand we’re agreed: either I lose my shorts or you lose the sweater.”

  I could see the heat in his eyes and felt something tingling from my breasts to my hips. I hadn’t been this excited about getting naked with a guy since the first time I’d had sex.

  “So wagered,” I said, my mouth feeling surprisingly dry. My heart was beating faster. I sipped my water. My hand was okay, not great, but that could change with the cards laid out in the community pool the next couple of rounds.

  “No point in doing a bunch of extra betting, is there?” he asked.

  I thought about that and shook my head. “Let’s just get to the point, then,” I said, setting out the first cards. I glanced at Dean rather than at my own hand; the cards hadn’t really helped me in any way. I had a pair, a high one, which if Dean was totally unlucky, might eke me out a win.

  “Not bad, not bad,” Dean said. “It does seem a little wrong to do this without betting rounds though, doesn’t it?”

  “How are we going to bet? We’ve only got pieces of clothing to wager at this point,” I countered.

  “I’ll raise you the sweater and a kiss,” Dean told me.

  My heart fluttered in my chest and I almost rejected the idea out of hand, but then I thought that a kiss was almost nothing, even if we were both nearly naked. It was safe.

  “I’ll see that bet,” I said. I threw down the next couple of cards, and those actually helped me: I had a straight, using both my own cards and what was in the communal pool.

  Dean licked his lips and smiled at me. “I think I’ll stick with my current bet. You?”

  I tried to think of something else I could wager, and shook my head when I came up dry. “I’ll stick, too,” I said, feeling a little cowardly. But I couldn’t get the thought of kissing Dean out of my mind. What would that even be like? Focus on the game, Kay. I took a deep breath and put the last of the cards down.

  “Show your hand, Dealer,” Dean told me.

  “Straight,” I said, flipping over my own cards on the table. I looked at Dean closely. He looked at my cards as if not trusting me, and then smiled slowly.

  “A straight is a very respectable hand,” Dean said. “It just isn’t quite as respectable as a straight flush.” He laid his cards out on the table and sure enough, he had won the hand.

  I swallowed against the dry feeling in my throat. “Then I owe you my sweater and a kiss.” I reached down and hauled my sweater off myself as quickly as possible, not wanting to give him the idea I was being a tease. Suddenly, I was in a super-luxe hotel suite with a billionaire, with nothing on me except for a pair of panties. I saw Dean’s gaze taking me in, inch by inch, lingering at my breasts and then my waist and then, down between my hips. The panties I’d chosen were not scandalous but they were green lace—not super concealing. I stood up and stepped around t
he table, taking a quick, deep breath to steady myself as I approached Dean for the kiss I owed him.

  Feeling a bit like a tease, I leaned in the last few inches and barely pecked him on the lips, pulling back and stepping away from him before he had an opportunity to try and make a move on me, or deepen the kiss.

  “So, next round decides which one of us gets the master bedroom,” I said, hurrying back to my spot on the other side of the coffee table.

  Chapter Twelve

  Dean

  I was already starting to feel the little attraction to Kayla starting to heat up into more when I won the kiss from her. Seeing her stripped down to her panties—and they were dark green lace, leaving very little to the imagination—was enough to start getting me hard, though I managed to push down the reflex to grab her when she kissed me on the lips. It was tough not to get distracted by the sight of her breasts, full and heavy, just above the coffee table as I tried to shuffle the deck for our next hand of poker. I wanted more than anything else in that moment to feel those tits in my hands, cup them and squeeze them and maybe taste them, but I knew it wasn’t time for that yet.

  I dealt out the cards to both of us and somehow managed to keep them all face-down in spite of feeling like my hands were dripping with sweat and almost shaking from the desire to touch her. My lips were tingling from the kiss still. God what would it be like to just pin her down on the floor and taste her mouth, feel her pressed up against me all over? I swallowed, realizing my mouth was watering at the idea, and drank down a little bit of water.

  “Do we want to fool around, or should we just get down to business?”

  I almost choked at Kayla’s comment. It took me a moment to snap out of it and realize what she meant.

  “I think we can go ahead with the hand,” I said, and felt my face flush a little bit, realizing that it was as much a double entendre as what Kayla had said. I gave myself a shake and checked my cards. I had two of a kind but they were twos. Nothing to write home about. Maybe I would luck out in the flop, the turn, or the river.

  I put down the first cards for the community pile face-up and shifted on the couch. The heat pooling along my groin wasn’t going away, especially as I noticed the way Kayla’s breasts moved when she did, shaking just slightly. It had been months since I’d seen a woman naked, in person, and I was definitely eager for something more but in spite of the fact that she’d kissed me and looked completely at ease, I wasn’t sure if she wanted to go there. Not really, anyway.

  “Actually, now that I think about it,” I said, licking my lips. How could they be so dry while I was salivating so much just at the sight of her? “Do you think we should ante up for this one, too? I mean, I’ve got a pretty decent hand going.”

  “The room isn’t enough for you?” Kayla raised an eyebrow and smiled at me, and I could see the color coming into her cheeks again. She took a breath and her breasts moved again and I felt even more heat building up between my hips. “Maybe the winner gets a longer kiss this time?”

  “At least the winner should get a real kiss,” I countered. “That last one was a copout.”

  “Fine,” she said, her tongue darting out over her lips for just a second. “Winner of this hand gets the room, gets to see the other person completely naked, and gets a one-minute kiss.”

  “Fair enough,” I said. “I agree to it.”

  I put down the next couple of cards, and I had another pair. Two pair definitely upped my odds of winning but Kayla’s eyes glowed when she saw the cards I’d put down on the table.

  “Anything else you want to ante up?” she asked.

  I shook my head. “I think I’m pretty good where we’re at right now. I don’t want to overstep and be that creepy dude, even if I win.”

  “All right then. Let’s see the river.”

  I laid out the last cards. They did nothing for me. I still had two pair at best.

  I laid my hand down in front of me, holding Kayla’s gaze. “Two pair. Not quite as good as the pair staring me in the face right now but pretty solid.”

  Kayla grinned back at me, not getting offended in the slightest at my joke. “Full house,” she said, laying her hand down for me to see. “I win.”

  For a moment, I stared at her. It wasn’t that I was surprised that she had won; two pair was a respectable hand, but it wasn’t one of the top three hands. It was more that I hadn’t really given much thought to what it would be like to lose. I’d been so wrapped up in the sight of Kayla’s mostly-naked body that I hadn’t really considered what would happen next.

  She rose to her feet and crossed her arms over her chest.

  “What?” I raised an eyebrow.

  “Pay up,” Kayla said, nodding significantly. “Off with the boxers.” I couldn’t help but chuckle, in spite of the fact that I knew that as soon as I did take my shorts off, she’d see I was more than a little bit affected by the way our game had gone. I stood up and hooked my fingers in the elastic waistband of my boxers and pushed them down over my hips. I wasn’t fully hard but I was starting to get erect, and my cock bobbed up slightly as I let the cotton that had just been covering it fall to the floor.

  “What about the other part of the bet?” I raised an eyebrow at Kayla, even as I watched her take me in, look at me from head to toe. I couldn’t even be embarrassed—the expression on her face was unmistakable. She blinked and then I saw the color rise in her cheeks.

  “Right… that,” she said, smiling slowly. She stepped around the coffee table and my hands almost had a mind of their own, reaching out for her and closing around her waist. I pulled her closer to me and leaned in at the same time, and Kayla looked up at me with those big, green eyes, her cheeks all flushed. She closed her eyes an instant before my lips connected with hers, and I gave up any pretense to counting the number of seconds.

  She tasted like coffee and sweetness, like heaven as I slipped my tongue past her lips and pressed her body against mine. I could feel Kayla’s nipples harden against my chest, and I heard her let out a tiny little moan as I nibbled at her bottom lip, deepening the kiss. Heat shot through my body straight to my groin, and I got harder and harder, until it felt like there was molten rebar between my legs.

  Before I could even think about making the next move, Kayla’s hands were on my chest, and she gave me a shove. I was so off-guard that I tumbled down onto the couch, looking up at her in shock. Had I overstepped? Had I read the signals wrong? Kayla’s eyes were dark, and her cheeks and chest were painted pink with the blood flowing through her. A second later, she was on top of me, straddling my hips. “I knew I was going to win,” she murmured, going in for another kiss.

  “You did, did you?” I only just got the words out before her mouth was up against mine again, and I slid my hands around to her back, pressing her against me. Her body felt like absolute heaven, and I wanted—more than anything else I could think of in that moment—to spend hours memorizing every line and curve, feeling every bit of her and searing it into my memory.

  “I always win,” Kayla told me, her voice full of pride. I chuckled and shifted her on top of me. I could feel how hot she was through the lacy fabric of her panties. I knew she wanted even more.

  “Not this time, I think,” I said, and I tumbled her off of me and onto her back on the couch. I kissed her again hungrily, rocking my hips against hers, feeling how wet she was. She’d soaked through that thin little trace of fabric covering her pussy. It felt great against my aching cock but I knew I needed more. I needed to feel her wrapped around every inch of me.

  I kissed a path down to her breasts and slid my hands down along her body, until I came to the waistband of her panties. Kayla moaned as I found one of her nipples with my lips, and began to suck and lick the sensitive little nub, worshipping it with my mouth. I tugged her panties down and they were gone before I even had time to think about the logistics, leaving us both naked. Her pussy was soaking wet, and I could feel a little bit of stubble against my fingertips as I slid them alo
ng her slippery labia, stroking her as I switched from one of her breasts to the other. I pressed a little harder with my touches, sliding up and down along the seam until I found her special spot, and began to rub her slowly, earning a long, low moan from Kayla for my efforts.

  I stroked her pleasure center and brought my mouth back up to hers, kissing her hungrily as I tried to hold back from taking her just a few moments longer. Kayla’s hips bucked as I worked her with my fingertips, her pussy getting somehow even slicker, even wetter and hotter as she moaned and writhed underneath me. I’d been with my fair share of women before—as Kayla herself had pointed out, I was reasonably good looking and I had a lot of money, so it wasn’t hard to get someone to sleep with me—but it had been years, at least, since I’d felt someone so wet and so hot so quickly.

  I probably should have been more on top of things, probably should have thought of a condom—or even to ask if Kayla was on birth control, and if she was clean—but in the heat of the moment all I could think of was how much I wanted to feel her from the inside. I brought my fingertips up to my mouth and licked them clean; she tasted like wine, tart and sweet and sharp, and I told myself that when I wasn’t quite so in need, I would love to spend a good thirty minutes down between her legs, making her scream and moan from pleasure, tasting that deliciousness until she drenched by face.

  But for the moment, I guided the tip of my cock up against the folds of her pussy, and looked down into Kayla’s face. “You want this, don’t you?” I had to hear it from her. I had to get the green light.

  “Oh, good god, yes, I want it,” Kayla said, moaning and impatient. I chuckled and thrust into her slowly, letting my cock push past the little ripple of tension as her body tightened around me. She was tight, hot, and wet, wrapped around my cock like a second skin as I pushed deeper and deeper inside of her, letting her feel every inch of me. I paused when my hips were pressed right up against Kayla’s, kissing her lightly on the lips, the cheeks, her chin, her eyelids.