Cowboy's Fake Fiancée: A Single Dad & A Virgin Romance

by Piper Sullivan

  “I see that,” he said as he stepped forward raising his hand.

  I had backed away then, not sure what his intentions were, while my insides were doing flip flops like popcorn in a hot pot. He had kept his eyes locked on mine and I had been frozen on the spot, rendered completely speechless. It was there and then that the simple kiss from two years ago, and all our subsequent mild flirtations, turned into something far more life changing.

  Jason had taunted me for being shy, and I had protested, even though I knew that he was right. Even when my nipples had poked at my sleep shirt, and his eyes had been riveted on them, I was still in denial. I had told myself over and over in those five minutes that I could handle it. But when he pulled me closer, and his lips had captured mine, I lost all self-control and common sense. Where I suddenly had found the courage to take what I wanted, god alone knows. But I wasn’t going to let that moment pass me by. With a sense of boldness, I had never been aware of, I kissed him back. Just remembering his reaction caused a whirl of emotion to flood my insides.

  Jason had wasted no time in divesting himself of his clothes. I had seen him shirtless, countless of times growing up. But not like this.

  I watched with fascination, as he stripped down to his boxers. I caught a glimpse of his sheathed erection in his shorts before he bent over and slid those off. His cock was thick, with a plump head. It looked like it was angrily pulsing. My mouth watered just looking at it bobbing in my direction.

  He had a condom in his hands. We had learned about sex-ed in school, so I knew how a condom was used, but I had never actually seen someone put one on. He tore the foil packet with his teeth before spitting out the wrapper. He gripped his thick member in one hand, while he swiftly and deftly unrolled the condom down his shaft.

  “I’ve been waiting to do this for years, and now you’re finally legal.”

  “What do you mean?” I asked.

  “That night you spied on me and Sonia? I set the whole thing up so that you would see us.” He chuckled and backed me up against the kitchen table. Gripping the hem of my nightshirt around my thighs, he slowly glided it off my body, leaving a trail of heat where his hands touched my skin.

  He was still for a moment, just staring at my breasts, my nipples stiffened under his intense scrutiny.

  “Damn, your tits are amazing,” he finally moved, gripping both my breasts with his hands and squeezing. Then he wrapped his fingers around my nipples and pulled.

  The only sound that came out of me was a moan of both pain and satisfaction. His pull on my nipples almost hurt, but I felt my clit jump in pleasure.

  When he popped a nipple in his mouth and started suckling furiously, I just about lost my mind. The wet sounds he was making turning me on as much as the sensation of his tongue and teeth on me.

  Jason lifted me onto the kitchen table and spreading my legs wide, he settled himself between them. His hand had traveled down to the space between my legs and massaged my clit in slow circles.

  “I heard you tip-toe past my door that night.” He said as he tapped two fingers at my entrance. “I opened my door and turned the radio on. I knew you couldn’t help yourself, I knew you would look. I wanted you to see what you could have, what I could do for you.”

  “How could you know I would watch you?” I asked.

  “I knew you wanted me.” He replied confidently, and popped a nipple back into his mouth, lashing it with my tongue.

  I squirmed in anticipation as he guided his cock to my core, still stroking me, faster. We both waited expectantly for him to plunge his dick into my waiting pussy. And he did. But he paused for maybe half a second before he ruthlessly thrust into me. I gasped and jerked back, my heart pounding relentlessly in my chest with the shock and pain of his invasion. But Jason gripped my hips tightly to him as he withdrew and pushed back in.

  I could hear the slippery sounds as my wet entrance clamped down on his cock with each thrust. I wrapped my arms around Jason’s back to steady myself as he pumped relentlessly, my tits jiggling and shaking with each thrust, rubbing against the hard planes of his chest. My initial pain fading to a hot heat.

  Right there in his parents’ kitchen, he fucked me senseless, not only once, but twice. On the counter, on the floor, it was unbelievable how we never got caught.

  I could hardly contain myself the next morning, I wasn’t even able to face Jamie, much less Jason. I left the house early, hoping that some space would help me garner the courage to tell Jason how I really felt. I wanted him to know that I wasn’t just another potential docking station, but I never got that chance.

  I leaned against the cooler door and latched it close; it’s been eight years already, and for a moment I wondered if Jason was ever going to be released on parole, or if he was going to spend his entire sentence in prison. Jamie never talked about what happened that day between her brother and her stepfather. And I didn’t ask. We had drifted apart for a time after that. My parents as usual wanted me to go to college, then Law School. It was their way of getting me away from the riff-raff crowd I should never have socialized with. Jamie and I only reconnected a few years later after her mother passed away and she found me on Facebook. I was there to help her through her grief and she was my pillar of strength after my parents practically disowned me.

  It wasn’t until earlier this month that she mentioned Jason’s name for the first time in years; it was in passing when she told me that she was thinking of paying him a visit, it was a fleeting comment, but enough to trigger a cascade of memories for me.

  A chill ran down my spine at the thought of Jason. And it had nothing to do with the fact that I just spent the last thirty minutes in the cooler, or that he had been convicted of manslaughter. It had everything to do with the unfinished business we had left behind and the uncertainty of it all.

  Jason

  The ride home had been exhausting but in the best way. Jaime and I had so much to catch up on. She filled me in on the last eight years, skimming over most of the bad stuff. I didn’t ask her about mom or her passing, and she didn’t volunteer to talk about what it had been like either. Instead, she amused me with her anecdotal tales of learning how to cook and clean. How she had accidentally put dish washing liquid in the washing machine and had bubbles coming out from under the laundry room door.

  I still couldn’t get over the fact at how much she’d grown up since the last time I’d seen her. No longer was she the frightened gangly teen that I’d been forced to leave behind. In its place was a beautiful, intelligent, and confident young woman. My chest swelled with pride at the person she had become despite everything that had happened.

  I was also grateful that she hadn’t been completely alone. I was both surprised and pleased to hear that Jaime and Ally had remained friends, or at least been there for each other during the loss of our mother. Jaime had briefly mentioned a period where they drifted apart, but when I pressed further she changed the subject. I was curious to know what had happened to Ally. Her parents never really liked us since they were upper class people, but unlike most spoiled brats, she was humble and shy in a cute way. I could only imagine the fallout when the headlines were out there and everyone in town realized that I was a murderer.

  As we rode along the country side, I couldn’t help but wonder what Ally would have had to say, knowing I was released. The last time we spent together was on the kitchen floor, then all hell had broken loose. I had never mentioned anything to Jamie, and I doubted that Ally would have. Maybe it was for the best, I thought.

  I started to recognize some of the landmarks, indicating we were getting closer to home. The reminiscing had been fun, but exhausting. Now, the mood seemed to peter out as we got closer to town. It went from jovial and carefree to somewhat somber and subdued as we pulled into the outskirts of town. The gravity of what had transpired so many years ago weighed me down and I could feel the sense of fear knocking at the fringes of my mind. We sat in silence the rest of the way as we made our way through town
and into our neighborhood.

  Thankfully, the drive had taken a little over three hours, so it was dusk by the time we pulled into the driveway. We lived on a relatively quiet street, but I didn’t relish a spectacle at my homecoming. Better to just make my way into the house quietly under the cover of night.

  I stared up at the house that had once been my home, and would now be again. It still looked the same; a traditional two-story A-frame house with a detached garage and wraparound porch. The house needed some TLC, nothing a little fresh paint and a few replacement boards couldn’t fix. But Jaime had done a good job keeping it up. I couldn’t help but smile when I saw the old porch swing still out front.

  Someone, Jaime I assumed, had replaced the old rusted out chains with new ones and it also had brightly colored pillow cushions, albeit, a bit girly for my taste. Jaime and Ally had spent hours on that swing, giggling and talking about god knows what.

  The smile faded when I thought about Ally, I had hoped that I would see her again, but I didn’t want to make it too obvious to Jamie, somehow I half expected her to be here too, but this wasn’t her home. She was probably married with children by now, living the life she was meant to have.

  The only lights on, were the ones on the porch. The house reminded me of a crypt, where all the horrible memories of the past lay buried deep in the concrete foundation, never to be dug up again. From the outside, I could see the white flakes of paint peeling from the window frames, like large eyes that lost the ability to cry over the years. This is what comes of reading Shakespeare when there’s nothing else to read in a prison, I thought to myself, making idle comparisons between living things and material structures.

  “Welcome home, big brother,” Jaime spoke softly as we sat in the driveway.

  I turned and gave her a ghost of a smile, “It’s good to be home.”

  Taking a deep breath, I opened the car door and stepped outside. I didn’t have any bags to get out of the trunk, so I just shut the door behind me and walked slowly up the familiar steps. Jaime passed by me to unlock the door. Pushing the door open, she walked in and flipped on the hallway light. Pausing by the stairs, she watched me closely.

  I stood on the threshold, not knowing what to expect or how I would feel taking my first steps back into this house after eight years. Bracing myself for the worst, I stepped into the familiar foyer and shut the door behind me. I hadn’t known what to expect, but I didn’t expect to feel this. No hints of anger or despair coursed through me, only relief, relief, and love and fond memories.

  I could see Jaime gnawing on her lower lip, unsure of what to say or do. I expelled the breath. I hadn’t realized I’d been holding mine and smiled at her. She immediately relaxed too.

  “Come on. I imagine you are starving for a good home cooked meal,” she said with a grin. “Why don’t you go get cleaned up while I get started.”

  The idea sounded amazing and as if on cue my stomach rumbled. We both shared a chuckle. I started to walk towards the full bathroom at the back of the house and realized I had no clothes.

  Reading my mind, Jaime said, “We kept all your old clothes. From the looks of it, most of them might be too small for you now, but I’m sure there is a pair of old sweats that you can sleep in. We’ll go get you some new clothes tomorrow.”

  “I’m sure I can find something,” I said as I headed up the stairs.

  I heard the door to the kitchen swing open and shut. Soon after the sounds of cupboards opening and closing and pots and pans banging filled the air. It was a little surreal being back home, but it didn’t hold all the ugliness that I thought it would. I think it helped that Jaime had made her own changes. Gone were the gaudy wallpaper, ostentatious furniture, and the formal pictures of the depicted happy family. Wallace had always been very keen on presenting the proper image of the perfect family. After all, the Winston’s had a reputation to uphold, and even though we weren’t true Winston’s as Gladys liked to remind us regularly, we still had a responsibility to act the part. No one had to know what went on behind closed doors.

  Jaime had removed all hints of the Winston’s from our family home. She had painted the walls a pale blue that was calming and replaced all the pictures with fun family portraits of happier times; when our Dad was still alive. There were many from when we were kids and all the vacations we took when our dad was still around and more recent ones with her and her friends, including Ally. I paused at a graduation photo at the top of the stairs. It was one with Jamie and Ally; I could recognize those creamy jade eyes anywhere. They had pulled me in when she’d just been a teenager, and seeing her again sent molten heat straight through my heart and down to my groin.

  Jaime and Ally were both grinning from ear-to-ear, diplomas in hand; arms around each other just like old times. Ally had always been a shapely girl growing up, and not even the generic graduation robe did anything to hide her ample curves. Memories of her on the kitchen counter with her legs wrapped around my waist flooded my memories. The way she swiveled her hips and arched her back each time I drove my cock… whoa!

  Don’t go there. Not now.

  I took a steadying breath and forced myself to look away from the photo and climb the rest of the stairs to my room, which were all the more uncomfortable now that I had a raging hard-on confined in the too-tight jeans I was wearing. I figured this was going to have to be a cold shower.

  I turned left at the end of the hall and opened the door to my old room. It was like walking through a time warp. I could see that the room was cleaned regularly because there was no dust or the smell of stale air that you would expect. But otherwise, it looked like nothing had been touched since I left. Posters of hot chicks and sports team adorned the walls. My soccer and basketball medals still hung from the corner of my dresser mirror.

  I felt tears sting the back of my eyes, and I quickly wiped them away with the back of my hand. There was no sense crying over time lost. I strode over to the dresser and threw open some drawers until I found a t-shirt and some loose drawstring pants that would work for tonight. Gathering the clothes in my arms, I walked out and closed the door. An enticing aroma was already starting to waft its way upstairs. My stomach growled reminding me that it had been hours since I’d last eaten. I would have plenty of time to think about my past and my future, but right now I just wanted a shower and full belly.

  I flipped on the shower and stripped out of my clothes. Stepping under the spray, I let my head fall back as the searing heat poured over my head and my skin. My muscles were still a little stiff from the long car ride, so I went through a series of stretches to loosen them up under the steam.

  I looked around for a bar of soap. Not finding any, I grabbed the bottle of body wash and squirted some into my hands. It smelled of lavender and honey, but I didn’t care. It just felt good to be clean. Lathering my body, I tried to scrub away any remnants of the Kenworth Prison. The scent of the body wash began to fill my nostrils, and I found myself drifting back to the picture of Ally on the wall, to that last night in the kitchen.

  Her ass was plump and her breasts were more than I could hold in the palm of my hands, soft yet firm. She was in complete rapture as I fondled them, and allowed my thumbs to graze over her taut dark pink nipples. Some nights when I lay in my prison cell, those precious moments were the only thing that kept me clinging to hope funnily enough. It wasn’t like we were dating even. I was at the prime of my youth, flirting with girls and bedding cheer leaders. Even when I stole the virgin kiss from Ally when she was just going sixteen, I never once thought that she would be the one, and I hadn’t thought that when she was eighteen and legal and I had finally put my hands on her.

  Then again, I wouldn’t have had the chance to consider that with everything that happened so fast. It was like someone decided to press the fast-forward button on my life. But now that I was out of prison, she was the first woman that came to mind.

  It had been a very long time since I’d felt the luscious curves of a woman and my bo
dy responded immediately, my dick hardened at the mere thought of her, naked and here in the shower with me. I could turn the water cold to try to douse the burning heat of desire coursing through my veins, but I knew that it would only be a temporary respite. What the hell? There were worse things in life than giving into the temptations swirling around in my mind. I slid my hand down to and gripped the base of my cock as I began stroking it with long firm pulls while recalling images of Ally and my dick buried deep inside of her. I wasn’t the same kid I’d been back then. I had been hardened by the system that failed me and the institution that had tried to end me. My fantasies weren’t about rose petals, moonlight kisses, and gentle lovemaking. No, I needed more than that for my release. I felt the tension build as I imagined having my hands on her, my teeth on her, taking her hard and fast with relentless thrusts, hearing her begging for more.

  I leaned my head against the shower wall bracing myself as the force of the release almost took me to my knees. I continued to stroke my cock roughly, watching the last of my seed as it swirled down the drain. Finally, I dropped my hands to my sides, breathing heavily, completely spent.

  Shutting the water off I stepped out of the shower and realized I had forgotten to grab a towel. Looking around the bathroom, all I could find was a damn washcloth. Remembering that my mom used to keep towels in the linen closet in her bedroom, I quickly snuck out hoping that Jamie was still downstairs and shoved the door to mother’s room open, only it wasn’t her bedroom anymore. Words escaped me as I came face to face with my muse. Green eyes widened in shock and possibly terror, looked straight at me, her lips parted as she sucked in a breath, clearly scared shitless. And then she threw a left hook and nearly took my jaw off in the process.

  “Fuck Ally!” I shouted in response and instantly put my hands up in defense, which only made the situation worse because what little flesh I was able to cover with the washcloth was now completely exposed.