The Christmas Gamble

by Sienna Ciles

  The whole drive back to the hotel, I’d thought about it. I knew, in theory, that there were some women who were easier to get off than others. I’d had a few times when--either from drinking a bit too much, or just not really being in the mood--I’d had trouble hitting a climax myself. But it wasn’t a normal thing, at least not for me, and not for any of the women I’d been with.

  I knew it was dangerous, and stupid, but I’d thought about what it would be like to get someone like Bethany off--someone who hadn’t ever reached orgasm with someone else. A woman like her, so controlled and wound tighter than a piano string, would turn into putty in your hands if you could actually get her there--I’d seen it happen.

  Now in the shower, I started washing my hair, trying to ignore the way my cock was getting harder and harder, thinking about what I could do to see what Bethany’s real problem was. There were a few different subsets of women who “just don’t get off,” in their own words, from what I’d experienced. Some of them were too in their heads to get to the right state of mind that it took to orgasm, and with them you had to basically make it impossible for them to think--distract them so much with what was going on with their body that they couldn’t overthink the situation even if they wanted to. Then there were the ones who’d been with guys who just had no idea what they were doing; with those women, you had to just take your time and worship them.

  Some women did have physical differences, of course--their G-spot was in a different place, or their bundle of nerves was not as sensitive, or was a bit tucked away. With them it was actually pretty easy, if you took the time to find out their geography. I wondered what kind of woman Bethany was.

  I put off washing my body until I didn’t have a choice anymore, because my dick was already so stiff that I knew I wouldn’t be able to help myself. When I couldn’t avoid it anymore, I decided to just lean into it. I was in the shower, after all; it wasn’t like I’d leave a bunch of evidence behind. I started thinking about what I’d like to do to Bethany to turn her on. Someone like her, she’d need a lot of fooling around just to get aroused enough to go through with real sex. She had probably gone down on a lot of guys just to give them something, I thought, shuddering as I gripped my cock and started stroking myself slowly.

  If that was the case, she was probably damned good at sucking a guy off. I groaned, and tried to press my lips together to stifle the noise, as I imagined her getting on her knees in front of me, wrapping her lips around my rod. She’d probably have great tongue game, too--swirling it around the tip, sliding it along the underside. I gripped my erection tighter, stroking a little faster with the help of some of the hotel body wash. I was going to have the cleanest dick in the damn building by the time I was done.

  I started feeling guilty in a weird way, imagining having Bethany’s mouth on my dick when she’d probably done that for most of her boyfriends to keep them happy--I didn’t want that for her, not when I was interested in getting her off. So instead I started thinking about what she’d feel like if we actually had sex. I mentally fast-forwarded through the preliminaries; I knew someone like her would need the buildup, and it would be hot as hell watching her get more and more turned on, but I wanted the main event. She’d be soaking wet by the time we got there, but I knew she’d be tight, her muscles flexing around me like her body wasn’t sure whether it wanted to try and keep my dick out or pull it in deeper.

  Somehow, instinctively, I was pretty sure she’d try to take control of the situation, moving her hips, trying to get me off as fast as she could. It’d be so fucking hot--and thinking of that made me moan again, turning me on so much I almost came right then and there. I slowed down a bit, wanting to actually enjoy my jerking off, and I bit my bottom lip. In the fantasy playing in my head, I’d make her slow down too, make her lie still--maybe pin her down and just slowly, slowly push deeper and deeper inside of her, taking my time to find her g-spot. I’d know when I found it, too--women can’t hide their reaction to that, any more than a guy can hide it when a girl gets just the right amount of suction around his dick with her mouth.

  I started going faster without thinking, bit by bit, imagining how I’d work Bethany up. I tried to imagine what she’d sound like moaning, but it was easier to think of what she’d feel like, clinging to me and trembling as she came closer and closer to climax. She’d be like a live wire in my arms, electric from how turned on she was, unable to keep still no matter how I held her. I forgot completely about the fact that she was just in the next room as I started pumping myself harder, even as I imagined pulling her legs up and perching her ankles on my shoulders, slamming into her and reaching down to rub her sweet spot to give her even more stimulation while the Bethany in my head lost herself in the moment.

  I imagined her coming, wrapped around my dick, almost shrieking with the pleasure of it all. She’d come hard, the first time she really got there--and probably for a good half dozen times after that, almost so much that it would scare her, and I imagined the “oh fuck” and “oh god! Oh my god!” leaving her throat as she struggled to make sense of what was happening in her body. Then, too, her muscles would clench around me--almost so much that it would be a distraction--and I’d have to struggle to hold back as her body tried to pull me into the depths with it.

  All at once I just lost it, almost falling to my knees as the first wave of my own climax hit me like a sack of rocks. I groaned again and again without even realizing it as I pointed my cock down to make sure any of the evidence washed down the drain. I shook from the force of my orgasm. It felt so good, the hot water flowing over me, my hand mimicking what I thought Bethany’s inner walls would feel like, the whole thing.

  I leaned heavily against the tile wall as I recovered, panting for breath, and shook my head at myself as I realized what I’d just done. When I was able to hear properly again, I realized that I’d made quite a bit of noise--but then, with relief, I heard the TV from the room itself. With any luck, it was loud enough that Bethany hadn’t heard me. The water was starting to cool, so I finished up my shower as quickly as I could. If nothing else, I should be able to sleep pretty well tonight, I thought as I dried off in the warm, humid air. I’d need to wet down my hair again in the morning to comb it the right way, but I wasn’t about to deal with the trouble of it now, when I was already pretty tired.

  Between the drive and the shower, I was more or less dead sober as I pulled my pajama pants and shirt on. I usually didn’t wear any underwear to bed--too much extra fabric, and I like a little freedom of movement, a little breathing room down below--but I figured it wouldn’t be an issue. It wasn’t like Bethany was all that likely to try and take a peek.

  I ran the towel over my hair one last time and hung up the towel, leaving the bathroom and stepping into the room itself. Sure enough, Bethany was watching TV, her phone plugged into the charging station on the bedside table. “Hey,” she said, giving me a little, shy smile.

  I hadn’t really let myself pay too much attention to her when she’d come out of the bathroom earlier; I’d caught a glimpse of her perky tits and her perkier nipples pushing at the fabric of her tee shirt, and it had nearly ended me, imagining what they’d look like without anything covering them up on top of everything else. She had the slightly shiny look to her face that women got when they did some kind of intensive nightly face treatment, which explained why she had such good skin--she probably studied and consulted experts to find out exactly the right products to buy and what order to use them in.

  “Good shower in there,” I said, walking over to the chairs I’d set up to be my bed for the night.

  “Yeah--good water pressure,” Bethany agreed.

  “It’s only ten?” That was what the clock said. “It feels like it’s should be at least midnight.”

  “Some of the reunion class are downstairs at the hotel bar,” Bethany said. “According to Jess, they’ve decided to party it up. We could join them if you felt up to it.”

  I raised an eyebrow at that, ge
sturing to her pajamas and then mine. “I don’t know about you, but I don’t feel like putting on real clothes--and these outfits are not exactly hotel bar-worthy.”

  “Well that helpful receptionist said they have a really extensive room service program,” Bethany countered.

  “We can do room service drinks,” I said, grinning. “Sounds like a good time.” I looked around and found the room service menu next to the TV, and started flipping through it to figure out what we should get. If nothing else, I thought maybe I could loosen Bethany up enough to get her to tell me more about the no-climax problem she was having. That’d be worth the overpriced drinks, even if nothing else came from it.

  Chapter Thirteen

  Bethany

  When Ransom had gone into the bathroom, I’d been at a loss for what to do with myself, so I’d settled for sneaking off my pajama pants to put some lotion on. I’d managed to get about halfway through that process when Jess called.

  “Hey,” I’d said, putting the phone on speaker. I figured that Ransom would be too busy in the shower to hear me, and once I’d gotten all the lotion off of my hands I could switch to regular talking.

  “Hey, girl! Tracy Marchen said that you got a room at the Clairmont?”

  “Yeah--we decided that it made more sense to be at the center of any action going on,” I’d explained.

  We’d talked about Ransom for a few minutes, and I’d finished up my lotion application and switched to normal mode on my phone after I got my pajama pants back on. I felt a little bit sticky from the lotion drying on my skin, but I knew from experience that I’d be silky-smooth in a matter of minutes.

  But about halfway through my chat with Jess discussing exactly what kind of crazy I was, I’d heard it—Ransom moaning. At first I’d told myself it was just enjoyment of the hot water, or something like that, but when I heard him groan again, and--just for a second--a telltale wet, rhythmic, slapping kind of sound, I knew what he was doing. He was jerking off in the shower. I didn’t say anything to Jess, but I hadn’t been able to keep myself from thinking of what he must look like.

  In spite of the fact that I’d long since given up on the thought of having anything to do with anyone sexually, I’d actually started getting turned on by the thought of Ransom naked, stroking himself. I had no idea what he was thinking about in the next room, but whatever it was, apparently it was pretty damn hot.

  I’d gotten off the phone with Jess and decided to turn the volume up on the TV, just to cover up the fact that I’d overheard him. As awkward as things had been when Ransom had gone into the shower, I figured that being uncomfortably aroused probably had at least part of something to do with it--and when he’d come out again, looking as relaxed and at ease as ever, I’d decided I was right.

  “We might as well go for the gusto,” Ransom said, handing me the room service menu and pointing out one of the items. In-Room Bottle Service. It included the hard liquor of the person’s choice--between vodka, tequila, and high-proof rum--along with a selection of juices and other mixers, a mini-cooler of ice, and some snacks.

  “Sounds good,” I told him, nodding my agreement. It was $100, which I thought was a bit much considering that I could buy all of the components for under $50, but I figured if Ransom wanted it and was paying for it, I wasn’t about to argue.

  He called down to the front desk, and we flipped through the channels on the TV until we found something we could both agree on--Casablanca, on one of the classic movie stations. I turn the volume down so we could at least hear the room service guy knocking, and we spent a few minutes just exchanging small talk.

  There was a knock at the door and I got up to get it, more excited than I would have expected to get down to drinking. As far as Jess had told me--and she was pretty well-informed--nothing was going to be going on all that early tomorrow for the reunion weekend, so there would be plenty of time for me to get over a hangover.

  “I just need someone to sign the slip for this,” the bellhop said, holding up a little folder with a pen attached to it. I nodded that I would sign it and the guy pushed the cart--complete with the bottle service setup--into the room while I stood off to the side to sign on Ransom’s behalf. I was pretty sure that it wouldn’t really matter which one of us signed it, since we were both on the listing for the room.

  I included a pretty decent tip and gave the folder back to the guy, wishing him a good night. It wasn’t until I closed the door behind him that I realized that my robe was open, and my nipples were hard again--or maybe still--against the fabric of my tee shirt. Oh well.

  I pushed the cart the rest of the way into the room and Ransom and I started helping ourselves. I filled a glass with ice and poured in some vodka and cranberry juice, along with a squeeze of lime, and snagged one of the bowls of chips and a smaller bowl of guacamole.

  “It’d probably be easier if we both just sat on the bed,” I pointed out, feeling awkward about Ransom’s sleeping arrangements.

  “As long as you’re not going to accuse me of trying to make a move on you when I go to steal some guac,” Ransom countered, and I rolled my eyes. I started sipping my drink, and realized--too late--that I’d made it a bit stronger than I normally took it.

  We started joking about Casablanca on the TV, and talking about the dinner, just blowing off steam, and as I finished my first cocktail and mixed myself another one--vodka with sprite and a splash of orange-mango juice--I was starting to feel loosened up.

  “So, tell me why it was that you decided it was so important to fool your classmates into thinking you have some big deal boyfriend,” Ransom said.

  “I kind of have been playing voyeur with social media, creeping on people’s lives,” I admitted. I wasn’t sure if I’d said anything about it before. “And everyone has their lives so together--married, kids, the big vacations and all that. I barely post anything.”

  “I remember that,” Ransom said with a nod. “But I mean, why should you even care what they think your life is like?”

  I thought about that, and it wasn’t the first time it had occurred to me to wonder why I was so worked up about the whole business.

  “I wasn’t really all that big of a deal in high school,” I explained. “I wasn’t, like, a loser or anything, but I was sort of Miss Second Place. On the Homecoming Court, but never the queen. A member of student government but never class president or even vice president, or anything like that.”

  “It seemed like a lot of people back there were pretty confident in your success in life,” Ransom pointed out.

  “I mean, they know I’m good at my job, but I guess I just wanted people to think I have it every bit as together as they do. Even if I’m turning into a spinster.” I laughed at that and helped myself to some of the roasted, spiced nuts that Ransom had taken off the cart.

  “You’re not a spinster--you’ve actually had sex,” Ransom countered.

  “I’m sure there were probably some spinsters who did, too,” I insisted. “They just never got anyone to marry them. And I’ll probably never get anyone to marry me. I don’t even know if I want to get married.”

  “Marriage isn’t the end-all-be-all,” Ransom said, and I wasn’t sure if he was agreeing with me or making a separate point.

  “What about you?” I asked. “Did you even go to your reunion?” I knew he was a few years older than me, but I realized that even after spending the afternoon playing “getting to know you” games, I wasn’t even all that sure how much Ransom had told me was him, and how much was his persona, James.

  “I went to a couple of different schools,” Ransom said. “So, while I could have gone to the one I spent senior year at, I didn’t really see the point, since I pretty much just filled a chair and got my work done. And I don’t think I even got an invitation for my other school’s reunion.” He shrugged.

  “I’m sure that the people you knew at your other school were at least curious,” I pointed out.

  “The ones I care about mostly know what I’ve
done with my life. The rest of them, I’m not even sure if I’d remember names or faces.” He sipped his drink and I sipped mine.

  “Don’t you think at least a few people from the school you graduated from were probably curious about you?” I asked.

  Ransom chuckled. “I’m sure some of them were, but that doesn’t mean I have to indulge their curiosity,” he said. “Not that there’s anything wrong with going to things like this--if it makes you happy.”

  “I’ll be happy if we can get through the weekend with everyone convinced that I’m a well-rounded success story,” I said.

  “I’ll do everything I can to help you with that,” Ransom told me. He raised his glass and we clinked our cocktails together before taking another drink.

  “We need to work out some more details,” I said.

  “Let’s do that later--I’m curious about something else right now,” Ransom said.

  I raised an eyebrow. “What’s that?”

  Ransom looked at me for a long moment. “Have you really never had an orgasm?”

  I felt my face burn with a blush, but I was loose enough from the alcohol to where I didn’t feel as embarrassed as I would usually.

  “Not with anyone else,” I said. “I’m...I’m not even really sure I’ve properly gotten off on my own.”

  “What do you mean, you’re not sure?”

  I risked a glance at Ransom’s face and saw him frowning in confusion. “I mean that I’m not sure that what’s happened actually counts,” I said. “I mean--I’ve watched videos and stuff.”

  “Well, most porn is pretty exaggerated,” Ransom pointed out.

  “I know that,” I said, my blush intensifying. “I know it’s an act, but I feel like…” I sighed and took a long sip of my drink. “From what I’ve read and heard and all that, I feel like if I really had gotten off, like--really--then I would know it for sure.”