The Christmas Gamble

by Sienna Ciles

  “Not necessarily,” Ransom said. “But if you can’t even really get yourself off, then that would explain why no one else has been able to do it.”

  “I said I’m not sure,” I protested.

  “How many guys have you been with? Did we talk about this before?”

  I shrugged; I couldn’t remember if we’d talked about it when I’d initially confessed my lack of climaxes. “I’ve been with five guys.”

  “Five, and not a single one of them knew how to get you off?” Ransom shook his head, clucking his tongue against his teeth. “That’s just sad.”

  “Hey--I told you before, some women just...don’t,” I countered.

  “Unless there’s something physically different about you, there’s no reason that you can’t get off--eventually, somehow,” Ransom insisted.

  “That’s not exactly true,” I said, but I wasn’t all that confident in saying it. Most of what I’d read had chalked up women being incapable of orgasm to a “combination of factors including physical and psychological.” I couldn’t think of a single psychological reason that I wasn’t able to get off, and my doctor had told me I was totally normal, from an anatomical perspective. So I never got a reason for why I couldn’t climax.

  “It’s just sad, a pretty girl like you never getting off,” Ransom said, shaking his head.

  “It’s not sad! It’s just one of those things,” I protested. “I mean, I feel like I’m missing out sometimes--and I especially did when I saw all those videos--but it’s like...like being colorblind, or something.”

  “Colorblind people have a physical difference in their eyes,” Ransom pointed out. “I assume you’ve asked doctors about your little problem?”

  “Not...exactly,” I admitted. “I mean, I asked if there was anything wrong with me--physically--and the doctors have all said that I’m fine.”

  “So, if there’s nothing physically wrong with you, it has to be psychological,” Ransom said.

  “It doesn’t have to be,” I countered.

  “It probably is,” he said.

  “It’s beside the point anyway,” I told him, crossing my arms over my chest.

  “Let me refill your drink--what were you on?”

  “I’m sampling just about everything,” I admitted.

  “How about a good old-fashioned vodka-tonic?”

  I shrugged, but when Ransom held out his hand, I gave him my glass.

  He mixed me a drink quickly and handed it back. “I have an idea,” he said, looking at me speculatively.

  “What’s that?” My heart was beating faster in my chest, even without knowing what he would say.

  “We were playing truth or dare--basically--earlier, quizzing each other,” Ransom explained.

  “What does that have to do with anything?” I sipped my drink and was surprised to find it was actually really good--cool, tart, with just a bit of a tingling feeling at the back of my throat.

  “I dare you to let me try and get you off,” Ransom told me.

  I almost dropped my glass.

  “You dare me?” I almost couldn’t believe it.

  “Yep. I dare you. I mean, we’re up here in this fancy hotel room, with nothing to do--why not?”

  For a moment, all I could do was stare at him.

  Chapter Fourteen

  Ransom

  As Bethany sat there, staring at me, I wondered if I’d overshot. I wondered if I’d made things completely awkward and overstepped my boundaries--such as they were--with her, and if she’d decide to just leave and tell her friends that we’d had a fight overnight and she’d sent me away.

  That wouldn’t get me any closer to my goal, and I’d miss out on the best break I could have possibly found on the information I needed. I had to think fast.

  “How about this? I’ll make you a bet,” I said. “We’ll try it, and if I can get you off within...let’s say one hour, you give me access to your agency’s adoptive parent files right away.”

  “That’s what you wanted to look up?” Bethany looked at me closely, seeming surprisingly sober for a moment.

  “It’s one of the things I want to look up,” I replied.

  “And if you can’t get me off, what do I get as your forfeit?” Bethany took a sip of her drink and some of her sudden sobriety faded out of her face.

  “You can decide to not give me the full access I need, and you’ll just give me the one thing I already told you I need,” I suggested.

  “What’s the other piece of information you need to get from the files?” Bethany raised an eyebrow, looking a little skeptical.

  “I need to also look at your records for parents who put their kids up for adoption, and the names of the kids your agency placed,” I replied. I might as well put all my cards on the table, right?

  “What do you need that information for, anyway?” Bethany frowned at me, and I saw the little line forming at the inner edge of one of her eyebrows.

  “That’s my business,” I said, shaking my head. “We agreed that you didn’t need to know it.”

  “I’m a bit suspicious how you’d use information like that,” Bethany said.

  “I can leave now, if you’re going to go back on the deal,” I said, shrugging.

  “If you’re not going to tell me, you’re not going to tell me,” she said, sighing. “Okay.”

  “Okay?” I looked at her a little more closely.

  “Okay, I agree to the bet,” Bethany said. “You’re not the first guy to think he’d be the one to figure out how to get me off, and the odds are not in your favor.”

  “I think they just didn’t know how to go about it,” I told her, grinning.

  “So you’ve said. We’ll see,” Bethany countered, and she looked pretty confident. I’d already--in the back of my mind--figured out what I wanted to do, if an opportunity came about to try and challenge Bethany’s record of no climaxes. The whole time we’d been sitting around talking about it, I’d been thinking about what it could be, why she hadn’t been able to get off as yet. So, I had an idea.

  “Finish your drink and turn your back to me,” I told her.

  Bethany looked at me askance and I chuckled.

  “Just let me work my magic,” I said.

  “Whatever, it’s not going to work anyway,” she said. She drank down about half her vodka-tonic in two gulps, and then finished it in two more, and set her glass aside, stumbling slightly as she turned around on the bed to put her back to me.

  I moved the snacks out of the way and slipped the hotel robe off of Bethany’s shoulders and got to work. I’d come to the conclusion that Bethany was probably one of those women who was too in her head, too tense, thinking about things too much--that that was why she hadn’t gotten off yet. So, the first thing to do would be to relax her. I’d asked for an hour with exactly that opening in mind, and even though she jumped a bit when I put my hands on her shoulders, she began to relax after a moment.

  I started at her shoulders and neck, kneading and working her muscles. It was no wonder she was too tense to come; I could feel the knots all along the top of her spine, the tightness in her shoulders, that told me that she was carrying tension all over her body. I’d learned a thing or two about massage here and there--one of my exes was a professional, and used to lecture absentmindedly to me while she worked my back and arms and legs for practice and fun. I couldn’t tell you what a myofascial sheath was to save my life, but I’d remembered what she’d said about tension points and how physical tension mirrored mental tension.

  It only took me a couple of minutes to see that my plan was already starting to work. I was careful with Bethany, starting with light pressure and working up as I tested her tolerances, and she let out a long, low moan of pleasure as one of the knots under my fingers just smoothed right away. I kept an eye on the clock, even though I knew that it would be better if I didn’t have a deadline to get her to where I wanted her--that wasn’t the terms of the bet, and I was determined to win for more than one reason.r />
  I gently pushed Bethany forward, and gradually worked my way down her back. “Can you lie flat on your stomach? You know what--here,” I asked, arranging the pillows so that Bethany could lie down flat without smothering herself.

  “I don’t know how you think you’re going to get me off with a massage,” Bethany said, a teasing note in her voice.

  She complied with my request, though, and lay down flat on her stomach, pushing her face down in the little groove I’d created. I kept going without saying anything to her little taunt, working my way down to the small of her back. She was actually, genuinely a gorgeous woman, and the parts of her skin that I was able to touch with my hands--I wasn’t about to take her clothes off, not just yet--was silky-soft, like someone in a commercial for a lotion company.

  I worked her arms and hands for a while, and when I was sure that she was fully relaxed--with thirty minutes to go on my time--I leaned in and kissed the back of her neck, shifting from kneading her muscles to caressing her. “You do know you’re a beautiful woman, right? You could have gotten a guy to do this whole reunion thing for you for free.”

  “I know I’m beautiful, but I just...oooh…” I nipped at the base of Bethany’s spine, and gently blew across her damp skin, even as I let my hands slide up along her waist to just under her breasts.

  “You just what?”

  “I just figured if I was going to have a fake boyfriend, I was going to make it as straightforward as possible,” Bethany finished.

  I turned her over, onto her back, as gently as I could and before she could say anything else I leaned in again and kissed her on the lips. I was focused completely on seducing her, not even trying to get into it myself, but the feeling of her lips against mine, the way she started to tremble just a little bit underneath me, was enough to get my mind going--and my body followed suit.

  I took my time, still, deepening the kiss bit by bit. I had to admit that for someone who wasn’t interested in sex, Bethany was a hell of a kisser--as soon as she got over being startled, her tongue batted and teased mine like a pro, and her lips moved against mine hungrily. Her hands moved up to my back, and I took the cue to start heating things up even more.

  I kept a little mental clock in my mind, and built on what I’d started with her. My plan was to just completely overwhelm Bethany’s ability to think--make myself a little unpredictable but comforting at the same time--so that she could only react to what was happening, instead of anticipating things and over-thinking them.

  I changed it up again, breaking away from the kiss to tug Bethany’s shirt over her head. Her tits were every bit as magnificent as I could have hoped--perky, the nipples already hardening from a combination of her arousal and the chill in the room, and when I cupped them, kneading and squeezing them carefully, Bethany moaned again, urging me on. I kissed her quickly on the lips and then moved down to her breasts, claiming one of her nipples with my mouth while I worked the other one between my fingertips. I sucked and licked, barely grazing the sensitive little rock-hard nub with my teeth to tease. Bethany’s trembling intensified into shivers.

  I switched to her other nipple and kept the pressure on the first one with my other hand, worshipping Bethany’s breast with my mouth, sucking as hard as I dared, testing her reactions every moment. She writhed and squirmed underneath me, her hips moving instinctively, and I knew without even having to check that she was starting to get wet, that she was probably just short of soaking already--but I wanted to get her so incredibly hot and so turned on that she could barely even stand it before I moved onto the real attacks.

  I moved up from her breasts and kissed her again, teasing her nipples between my fingers all the time, rolling and twisting them as Bethany started moaning a little louder, a little longer, into my mouth. I put one of my knees up between her legs and just like I expected, she pushed her hips down, rubbing against me on instinct. I could feel the heat of her through her pajama pants and my own, and I knew--I knew--she had to be soaking wet. But I wanted to push her just a little bit further.

  I dipped back down to Bethany’s breasts and started worshipping them with my mouth again, letting my hands glide down along her body to the waistband of her pajamas. I kept them there for a moment and then, when I was sure she wouldn’t stop me, I tugged them down, moving my knee out of the way to get them past her thighs.

  Somehow--I couldn’t say how--I was getting almost as turned on as Bethany was. As I started working my way down over her mostly-flat belly, I had time to notice I was hard as a rock in my pajama pants, in spite of having gotten myself off in the shower maybe an hour or an hour and a half before. I breathed in the smell of her: soap, lotion, and the deeper musk of her arousal, and it was like a jolt of electricity straight to my groin. I turned my head just a bit as I came to her hips and checked to make sure I still had another seventeen minutes to get her off. More than enough time, I thought. As turned on as Bethany already was, I was pretty sure I’d get there before time was up, even.

  I spread her legs further apart and shifted down in between them, pulling her pajama pants the rest of the way down her legs and tossing them aside. I took a moment to appreciate just how fucking gorgeous she was, sprawled out on the bed, flushed and with her eyes dark from how turned on she was. She was exactly what I liked in a woman: a little soft in the right places, with a nice curve from her tits to her waist to her hips, and legs that were lean but not muscular exactly. In spite of the fact that she was clearly not expecting any kind of sexual action, she was freshly shaved, which made it all the more obvious how wet she was.

  “If nothing else, we know you experience sexual arousal,” I said, grinning at her. I slid my finger along the seam of Bethany’s labia and she shuddered.

  “Arousal isn’t the problem,” she said, her voice breathless. “And you don’t have that much time left.”

  “I have enough,” I told her. I pressed a little more firmly as I slid my fingertip up and down along Bethany’s labia, stroking instead of just touching, and I saw her thighs tense up at the sensation. I spread her labia apart to reveal the pink, drenched inner folds, and I found her, swollen and straining out of the hood. Good little bead, I thought, barely brushing a fingertip against it.

  Bethany gasped and shuddered, her hands gripping the blanket in reaction to my touch. I tested her a little bit, trying to find what she liked best. Feather-light touches, then a little firmer, then a nice hard rub. I’d thought maybe she was too sensitive or not sensitive enough, and that might be why the other guys hadn’t been able to make anything happen. But she reacted the way I expected each time, getting more turned on even with me rubbing against her little pleasure center more firmly.

  I held her slippery-wet folds open and brought my face down, looking up at her face as I found her bundle of nerves with my lips and tongue. Bethany cried out as I started working her with my mouth, sucking lightly and swirling my tongue around her little bud. I tried a trick that never seemed to fail me with other women, and started pretending to draw letters of the alphabet with the tip of my tongue against her clitoris. A...B...C… I got to E and Bethany almost shrieked. I fought the urge to laugh and continued on through the letters, filing away the one I knew she liked for when I got through the rest. S and Z had her grabbing at my head, and I closed my eyes, focusing completely on the task at hand with the knowledge I’d gained.

  I worked her little pleasure button steadily, holding her hips down, keeping her exactly where I wanted her. I sucked the little bead of nerves between my lips and flicked my tongue against it, mimicking the different letters of the alphabet that I knew she’d liked, over and over again. I could feel the tension mounting in her, but I could also feel her holding back; I would need to add something to the repertoire before she got used to the sensations I was already giving her.

  I slid one finger inside of her slowly, nuzzling against her labia to keep them as open as I needed them to be. Bethany made a noise--somewhere between a wordless question and a whi
mper and a moan--and I pushed deeper. She was tight. She was tight enough that I thought it was possible that the guys she’d been with just hadn’t taken their time, that she had probably been in enough pain from their blundering attempts to pound her to climax that it was no wonder she’d never come.

  So I worked her slowly but steadily, feeling out her inner walls with first one finger and then the other, working her bundle of nerves with my lips and tongue the whole time. When I could comfortably fit two fingers inside of her, I tried finding her g-spot, slowly rubbing along her passage with my fingertips as I moved them in and out, deeper and deeper.

  I knew the instant I’d found it. Bethany’s muscles clamped down around me, her thighs threatened to crush my head, and a moaning cry left her throat like it might have torn something on its way. I chuckled and nearly choked, but recovered enough to keep going. I worked her with my mouth and fingers, brushing against her g-spot at first only every few thrusts and then rubbing against it more persistently.

  When I was pretty sure I was down to my last five minutes, I turned up the intensity again, flicking my tongue against her sweet spot as fast as I could and sucking the little bead hard, even as I rubbed hard against her g-spot from the inside. I could feel Bethany trying to fight it--I could feel her grabbing at my head and shoulders, feel her shaking from the effort of holding back the pleasure I was giving her, not succumbing to it. The moans leaving her throat cut through with stubborn whimpers that were still like music to my ears, and her whole body hardened around me as she tried to keep her climax at bay.

  I wasn’t sure if she was doing it to win the bet or if it was something she ended up doing every time she had sex, whether she wanted to or not--I was willing to wager it was the former and not the latter, though.

  I opened my eyes and glanced over at the clock, and saw I had two minutes left on our bet. I worked harder than I’d ever worked to get a woman off in my entire life, and right as the time ran out, I felt her shudder from head to toe, heard her gasp and almost sob.