High Stakes: A Dark Romance

by Roxy Sinclaire

  He grabbed the condom from the table and rolled it on his hard cock. He slowly inserted the tip and eased his way in. It did hurt a little bit. I hadn’t had anything more than a few fingers in there before, and he was a lot bigger than that.

  “How’s that?” he asked, grabbing my outer thighs.

  “Fine,” I said, not wanting to kill the mood.

  “Just relax,” he said, kissing me on the neck.

  My muscles were tense. The fact that I was having sex for the first time and being nervous about it was making my muscles clench up. I listened to his advice and closed my eyes, allowing myself to give in to the pleasure.

  Instantly, the discomfort decreased, and it was starting to feel good. Little by little, he went deeper and thrust faster. I was beginning to get a feeling deep in my body, like the one I felt when he was going down on me. I could feel my breathing deepen with each thrust.

  I cracked my eyes open to get a look at his face. I could only describe his expression as pure ecstasy. His white teeth bit down on his bottom lip as he squeezed my hips and my ass.

  With a final shiver, he came, and he looked at me in a way that no one had ever looked at me before. I couldn’t quite place the expression. He looked like he wanted to say something, yet he was silent.

  Josh rolled over onto his back, right next to me.

  “That was incredible.” He sighed.

  “Yeah?” I asked, a bit disbelieving. I hadn’t really done anything other than lie there.

  “I have to admit,” he said, “I wasn’t sure what sex with a virgin would be like. You did not fail to impress. My only regret was that I couldn’t last longer. How was it for you?”

  “It was . . .” I struggled to find the right words. “Not bad.”

  “Ugh,” he groaned, covering his face. “You don’t have to protect my feelings. It really wasn’t good, though?”

  It certainly wasn’t bad, but I couldn’t put the experience into words. At least, I couldn’t put it into words that I felt comfortable telling a complete stranger.

  The thing was, actual intercourse aside, I felt like I had made an emotional connection with him. I knew better than to fall in love with a stranger, but there was something more than just physical attraction between us. I didn’t know if there was anything more to our relationship than a one-night stand, but I wanted to find out.

  “It was good,” I reassured him. “I just didn’t know what to expect.”

  “Maybe we can give it another go later,” he said, grinning.

  As he got out of bed to go to the bathroom, I looked around the room. The walls were plain, and there was no sign that anyone lived here long term. His friends must have some money because I knew few people my age who could afford to live in a house in the city with empty bedrooms.

  I could still hardly believe what had just happened. Twelve hours ago, I was sitting by the pool, ready to pack up my things and leave the next morning. I assumed I’d watch my friends get wasted and lose all of their money. It would be another night of following my friends around.

  Instead, I had met a guy who was interested enough in me to take me back to his place. I had sex for the first time in my life, and it was incredible. I didn’t want to leave. I couldn’t leave.

  My parents were the conservative type, so sex was never discussed in my household. I knew that I was expected to save myself for marriage, but my mother assumed I would be married by now. She married my dad at the age of twenty, but things were different for them. My dad was the oldest son of an oil tycoon and next in line for running the family business. My mom dropped out of college to marry him and begin her wifely duties. She directed the help, made sure her kids were cared for, and planned social events.

  That wasn’t the life I wanted, though. I knew that if I decided to marry rich, I could probably find the homely son of a family friend to be betrothed to. I had all the money I needed. I wanted love and fun and adventure. I couldn’t possibly stay cooped up all day.

  When I got to college, my attitudes on sex and relationships shifted. Suddenly, I was surrounded by women who didn’t see sex as a big deal. They felt free to find pleasure in men without committing themselves to a long-term relationship. When my friends and I would talk over a few bottles of wine, I felt like an outcast, like there was some secret club I was excluded from.

  Now I felt like I finally fit in. I had this shared experience that so many of my friends liked to talk about. And, they were completely right—virginity really wasn’t that big of a deal after all. I didn’t feel an ounce of shame for what Josh and I shared in his bed. We were just two people attracted to each other, making each other feel good.

  Josh came back into the bedroom, wearing a pair of athletic shorts tied low on his hips. I marveled at his cut torso, and my eyes moved down to his shorts. Without the constraints of underwear, I could see the defined shape of his package. No wonder it hurt.

  Half expecting him to tell me to get dressed and kick me out, I was surprised when he got back into bed and pulled me close to him. He lifted the comforter and pulled it up to our necks, and we spooned.

  “I never want to leave this bed,” I said softly as he nuzzled my neck.

  “You don’t have to,” he said.

  “Eventually,” I laughed, “I think I’ll have to go.”

  “We can talk about that later,” he said. “For now, I just want to be with you, away from the rest of the world.”

  We lay there for a moment in silence, just enjoying our time together, because we both knew that it wouldn’t be long before we went our separate ways.

  I was starting to wish our circumstances were a little different. At first, the thought of sleeping with a total stranger was ideal. If things didn’t go well, then I would never have to see him ever again. I could just go back to my friends, tell them the story, and then move on with my life.

  Now, I wanted to see where things would go with Josh. It hardly seemed fair that the first person I had any interest in for years would live halfway across the world. I didn’t feel like there was any way to make this work between us.

  I closed my eyes and just tried to take in everything I could about this moment. I was in the arms of the incredibly sexy man who’d made me feel things I had never felt before. I breathed in the scent of fresh sheets and men’s deodorant. His skin felt smooth against mine, and the way his index finger floated along my curves gave me goose bumps.

  I flipped over so I could face him. His face was perfection. He had soft blue eyes that crinkled at the edges when he smiled. His strong, square jaw was covered in sandy brown stubble. I loved when he smiled because his soft pink lips split apart to reveal a row of perfectly straight, white teeth. He certainly defied the British teeth stereotype.

  “How long are you staying here?” I asked.

  “Probably another week or so,” he said. “Why? Do you want to extend your holiday?”

  “I can’t.” I groaned again. “I can’t just skip my flight tomorrow. Anyway, where would I stay? The good hotels are booked way in advance, and I am not staying in some shady motel.”

  “You can stay here,” he said, pulling me in for a kiss.

  I smiled and kissed him back. I moved in closer, my bare chest on his. Usually, I was a little self-conscious about showing so much skin, but at this point, it wasn’t a big deal. If he liked seeing me naked in his bed, I wasn’t going to deny him that view.

  Things became hot and heavy, and before I knew it, I was pulling his shorts off and reaching for another condom.

  “You go on top this time,” he said.

  “Are you sure?” I asked, not exactly sure what to do.

  I think he sensed my apprehension. “Just do whatever feels good,” he said.

  With that, I straddled him and he guided his erection inside me. I felt a little pressure, but it wasn’t painful like last time. I bounced around a bit before finding our rhythm, our hips moving in sync.

  While I rode him, he rested his hands on my
hips, helping to control the speed. I watched the pure bliss on his face, and it made me feel powerful. I found the right spot, gyrating my hips as our flesh rubbed against each other.

  As a moan escaped my mouth, Josh gripped my hips even tighter, moving quicker, in and out. When we had both finished, it was my turn to flop onto the bed in exhaustion. This night was probably the most exercise I had gotten in weeks.

  “Fuck,” he panted. “You are truly incredible. I don’t think I can let you go home tomorrow.”

  “I really don’t want to,” I said.

  “Why do you have to go?” he asked, sitting up a little. “Is there something at home that can’t wait?”

  “No,” I started. “I don’t know. I just didn’t plan on staying longer. I don’t really have anything going on.”

  “Then why do you have to leave?” he persisted. “Even just one more night. Wouldn’t that be worth it to you? I’d do anything to get you to stay one more night.”

  I gave it serious thought. I hardly had a job, so it wasn’t like I needed to get back for work. I didn’t care if I lost money on another flight. My friends might be annoyed at me for not joining them, but they would understand. Besides, what was one or two more nights to them? For all I knew, this would be the only intimate interaction I would have for the rest of the year.

  “Think it over for the rest of the night,” he said. “If you wake up in the morning and you want to go, I’ll understand. If you decide to stay with me, you’ll make me the happiest man in the world.”

  “So no pressure?” I joked.

  “None at all.” He smiled, kissing me on the cheek. “I don’t know about you, but I’ve worked up an appetite. Should we order some food?”

  “That sounds amazing,” I answered. I walked into the bathroom to freshen up. I put on my undergarments, but I didn’t feel that being fully dressed was necessary. With any luck, we’d just take it all off again.

  When I looked into the mirror, there was something different about me. My face was glowing and my hair was tousled. I stood up straighter than usual and couldn’t stop grinning. I felt like a new woman. I knew that the effects of Josh’s affection would wear off soon, so I stealthily snapped a mirror picture of myself, if only to capture the moment in time that I felt my sexiest. Maybe I’d get the opportunity to send it to Josh when we had both parted ways as a memento of our time together.

  Chapter 5―Joshua

  The rest of the night, Amanda and I stayed up late talking, drinking, and having sex. For a girl with no prior experience, she certainly had an appetite for it, and I couldn’t deny her. It was as if I had uncorked a bottle of champagne—once her sexuality was released, there was no bottling it back up.

  I realized that I had made a bit of an error in my plan to get her money. In my effort to get Amanda alone with me, I had developed feelings for her. I felt incredibly stupid about it, and I didn’t want Ben or Reese to know about this. This wasn’t part of the plan, and I didn’t want to get myself into any trouble with my friends.

  With one more day, I could get back the focus I had lost. I would have enough time to spin a story that would make her sympathetically hand me money. Ben wanted more than I had ever scammed anyone for in my life. Tens of thousands of dollars would help us live in our house with our meager possessions, but more importantly, I could use my share to get myself out of here for good.

  This would be, by far, my most difficult job to date. It wasn’t so much that I couldn’t weasel the money out of her, but the fact that I didn’t want to do it. I had a feeling that, even this early in the game, she would buy a good sob story and give me everything I wanted. I hadn’t even taken more than a nice dinner from her, yet I already felt the guilt gnawing at the pit of my stomach.

  The feeling of guilt was so unfamiliar to me that it took a while to name the strange sensation. The last time that I felt guilt was when my dad told me that I was part of the reason why my mom left us all those years ago. Since then, I managed to reason my way out of ever feeling that emotion. Lying next to Amanda in my bed, part of me wanted to tell her that she should run away from me as fast as possible. She deserved to be with a good guy. I certainly wasn’t that.

  At one point, we had started talking about our family lives. I kept my details vague, but I did admit that I came from a poor family and worked hard enough to buy the things I needed in life. She listened and nodded, but I could tell that even the true bits of my story were beyond her comprehension.

  Then she told me about her upbringing in Texas, and to be honest, it wasn’t how I imagined her life to be. In my experience, heiresses were generally rich snobs who expected everything to be handed to them. They typically lacked any sense of morality, so it didn’t feel wrong to rob them blind. Amanda had a lot handed to her, but she understood how lucky she was and expected nothing. Her family’s wealth was even a bit of a burden on her.

  She knew how people perceived the obscenely rich and didn’t want that reputation. She wanted to be a hard-working member of society, but it was hard when her parents forbade her to work throughout her schooling. Once she was on her own, a blank resume was hardly what employers wanted to see. She used her family connections when absolutely necessary. Otherwise, she hid her family name from the world.

  In a strange way, our parents’ social status had stunted us in a similar fashion. My lack of money growing up made it harder to have the same opportunities as the other kids at school. Amanda’s wealth made it hard for people to take her seriously. Often, we were never given the chance we thought we deserved.

  On paper, we could not be any different. Yet, once you dug further into the feelings we buried deep, we were so similar.

  Despite my appearance, I had a hard time entering serious relationships with women. Since I knew that no self-respecting woman would want to be part of this life, I had to choose the women who didn’t mind my unsavory occupation. I know it’s hypocritical, but I couldn’t be with a girl who wanted to use me for the money I illegally acquired.

  I had worked as a bartender at a few different locations, but I didn’t enjoy the work, especially when I knew I could make a hundred times as much money in one night by scamming people. I still worked the occasional legitimate job, but that was more so I could appear to be an average citizen if it ever came into question. It’s just so hard to turn down that much money for a relatively small amount of work.

  As we cuddled, I allowed my mind to enter a fantasy world where Amanda and I had the chance to date for real. I would get a legitimate job, not like we would need it with her money. We could go wherever we wanted and leave everything behind. I loved the idea of coming home from work, crashing on the couch, eating takeout with the TV on in the background, and making love in the evening.

  Though, even in this fantasy, I would have to be a completely different person. Also, in this daydream, I would have to tell her that I tried to steal her money and she’d have to be perfectly okay with that. Even as a fantasy, it seemed a little farfetched.

  “Do you ever think about leaving everything behind and starting over?” I asked.

  I half expected her to give me a weird look, but she nodded solemnly. “Quite frequently, actually. You?”

  “Yes,” I answered honestly. “We could just run away together,” I said, only partially kidding.

  She laughed. “We’ve known each other for about half a day. Everyone would think I had lost my mind.”

  “Yeah,” I agreed, feeling a bit defeated. “I suppose that would be a bit crazy.”

  “Do you think you could leave your friends and family behind?” she asked.

  “I don’t really have much for family anyway. My friends are fine, but you can always make new friends.”

  “I guess.” She sighed. “My friends are kind of assholes sometimes, but they’re still my friends. I don’t know if I could leave my family, though.”

  “Are you close to your parents and siblings?”

  She forced a chuckle. “Hones
tly, not really. I just feel like I have this obligation to let them control my life.”

  “Why?”

  “Well, if it weren’t for them, I wouldn’t be flying first class to Las Vegas for the weekend. They’ve financed my entire life. I kind of owe them. It’s a strange conundrum, isn’t it? Their money has managed to stunt my growth into an adult woman, yet I feel like I have to repay them for it.”

  “That’s pretty fucked up,” I laughed.

  She joined me. “Yes, it definitely is. One day, I’ll absolutely break free from them. I just don’t have the courage to do it anytime soon.”

  I understood. I felt the same way about my relationship with my friends. I felt indebted to Ben, even though I didn’t always like the control he had over my life. Still, he had given me an opportunity to make a lot of money. Otherwise, I don’t know where I would be right now. Probably in Georgia, working at a gas station for minimum wage or something.

  Amongst the conversation and the kisses, we drifted off to sleep, our bodies exhausted from the pleasure we had induced in each other. When we finally fell asleep, it seemed like I had just closed my eyes when I heard Amanda’s phone ringing. I checked the time—we had been asleep for just a few hours.

  We both groaned in unison from our unwelcome awakening. The sun was peeking through the curtains as her phone buzzed.

  “Hello?” she croaked.

  “Where are you?” the loud voice on the other end of the phone said. I assumed it was Tanya, the ringleader.

  “I stayed over at someone’s place. What’s up?”

  “Well, we were just going to order breakfast and realized you weren’t in the room. I thought I’d check to make sure you hadn’t been murdered or anything.”

  “Nope. Perfectly fine.”

  “So are you going to get your ass back here to pack anytime soon? We probably need to go to the airport in a few hours. We’re also ordering one of those hangover cure teams over to give us vitamin IVs because we’re still pretty fucked up from last night. Should I get you one?”

  “No,” she said. “I’ll be back in a bit to get my stuff.”