Big Bad Cowboy: A Billionaire and a Virgin Romance

by Tia Siren

  “You mean, forever? Or just this week,” Jeff asked.

  I blurted with laughter which I immediately had to staunch with my hand. I hoped they hadn’t heard me, and it didn’t look like they had.

  “No, Jeff. Albert is a good guy; he’s much better than all the other guys I dated,” she said.

  “Well,” started Jeff, “you might want to speak a little quieter because just about all the other guys you dated are at this party.”

  Carol had a frustrated look on her face, and she looked at Albert to defend her, but unfortunately for her, he remained tight-lipped.

  “I didn’t come out tonight to get made fun of by a linebacker,” Carol said in a vain attempt to puff herself up.

  “I didn’t know I was making fun of you. I just wanted Albert, here, to know what he was getting himself into,” Jeff said.

  Carol, obviously flustered, stormed out the front door, followed closely by her date of the evening. I couldn’t stop laughing at how handily Jeff had dealt with the couple.

  “You didn’t want them here, right,” Jeff asked as he walked back up, “cause if you want them back, I don’t think it’s going to happen.”

  I reached out and wrapped my arm in his.

  “Jeff, you just made my night,” I said.

  “Let’s get you a drink and pick up where we left off the other day,” Jeff said.

  I nodded, and he poured me a glass from the keg. I wasn’t much of a beer drinker, nor was I much of a drinker in general, but Jeff had earned at least one drink from me.

  We adjourned to the tiny backyard of the house. Christmas lights were wrapped neatly around the trunks of the sparse trees that provided cover in the backyard. A picnic table sat against the fence, and the tables that Matt and I had setup earlier were currently occupied by people trying their best at beer pong.

  We grabbed a couple camping chairs and sat them on the grass away from the crowd so we could chat.

  “I didn’t know you were a linebacker,” I said.

  “Well, I don’t exactly advertise my position. Besides, the people that come see the games know my position; the people that don’t see the games just don’t care. I don’t care enough to tell everyone my life story.”

  “So you’re saying you don’t tell people that don’t watch games because you don’t think they’ll really care that much,” I asked.

  “Exactly. It’s like your mock trials, why would I care if someone was a judge or a prosecutor, it kinda just feels like an unnecessary label, doesn’t it?” he said.

  I laughed at the silly train of thought. But, he had a few good points, I honestly didn’t care what his position was, and knowing it wouldn’t have made me think any more or less of him.

  “How’s your mock trial prep?” he asked.

  “It’s going well,” I said.

  “That’s all I get?” he said.

  “Well, what else am I to say? It’s just busy work. Besides, it’s been driving me crazy lately.”

  “How so?” he asked.

  “If you want to present a good case, you have to do a lot of research. You have to check precedent cases, and gather any evidence you can in order to defend your client. I think I’m in a good position, but there’s really not much to tell.”

  He sat there a moment in thought. It seemed that he liked to try to pick his words rather than just blurt out anything. It was different from when I first met him; his demeanor seemed almost professional today; as though he were an expert chess player looking to gain the upper hand on his opponent.

  “Why do you do it?” he asked.

  He had already asked me this question before, or some version of it. I wanted to give him the same answer as it still seemed relevant, but I didn’t for some reason.

  “It’s expected of me,” I replied.

  “They expect you to be on the mock trial team?” he asked.

  “No, not that,” I said.

  I didn’t really know what I wanted to say. I was caught in this odd moment of trying, to be honest with not only myself but with another person.

  “My parents always wanted me to get ahead in life. They wanted me to be the best I could be. I’d always do my homework with them, and they would make sure it was right. I’d exercise and eat right, I’d make friends with people my parents would approve of, and I didn’t do anything crazy.

  “I’m expected to be smart. I’m expected to get good grades and have a nice job in a boring office, with a boring husband. I don’t know what I really want; I don’t know whether that’s my parents in my ear or if it really is me that wants those things,” I tried to explain.

  He nodded and sipped more of his beer. For a minute he didn’t say anything, he just sat there rubbing the scruff under his chin. I started feeling embarrassed for saying something like that so soon. Even Albert didn’t hear that little piece about me.

  “My parents were barely there,” he started, “I’d come home and be alone from the moment I got there until almost bed time. But, my dad would always come in and read me a bedtime story to put me to sleep. Sure, I’d grown out of it eventually, but even today I still miss it. I spent every waking minute trying to make time go faster, so I joined any afterschool events I could. Football was the first one that clicked.

  “I might look like a messed up kid, getting in with the wrong crowd, making bad decisions, but those decisions were made by me and me alone. I never got a helping hand from my parents, but I loved them just the same.”

  He returned to his beer. We sat in silence for an undetermined amount of time. I don’t think either of us had anything to say. It felt like we had just skipped past the point of going on dates and were already well into the relationship stage.

  I somehow felt comfortable around Jeff; he knew something about me that I rarely shared, and I knew something about him that seemed personal.

  “Do you want to make a choice for yourself?” he asked.

  I stared at him with a confused look.

  “Well, a decision that only you can make,” he said.

  I nodded, hoping he would get to the point.

  “I thought I’d take you to-”

  “Holly!” I heard Matt shout at me from behind.

  “Matt!” I shouted back a little less than enthusiastically.

  “I thought you might want to meet my Girlfriend, April,” he said while shoving a lovely young lady in front of us.

  She was dressed in a simple sun dress and heels. She was cute, with Islander features and a petite build. She looked just right for Matt, if not a little out of place considering the height difference.

  “Hi April, nice to meet you, would you excuse Matt and me for a second,” I said.

  I grabbed Matt by the arm and led him away from the other two. I was doing my best to hide my frustration.

  “Matt, you just had to butt in at the worst time,” I said through clenched teeth.

  “Oh, come on now. It’s a party. You can’t expect to sit in a corner the whole time,” he replied obviously drunk.

  “Listen, I’m going to get out of here. Maybe you can have me meet April some other time, and we can go out for lunch or something. I’m going to take off with Jeff,” I said.

  Before I could walk away, Matt grabbed me by the arm and pulled me back.

  “Okay, do what you want, but be careful around Jeff. I think he might have some other motive for trying to get close to you,” Matt said.

  “I think I’m going to make this decision for myself this time,” I said while pulling his hand off my arm.

  “That’s fine, just remember what I said,” he added as I walked back to Jeff.

  “Come on, Jeff. Let’s get out of here,” I said taking him by the hand and leading him toward the exit.

  “Lovely to meet you, April,” I said with a smile as I continued to walk off.

  Jeff stumbled along behind me, seemingly surprised by my haste.

  “Let’s see where you wanted to take me,” I said.

  4.
/>   His car rumbled down the road. Thankfully he hadn’t had more than half a beer the entire night, so he was practically sober. I didn’t know where we were going, but it certainly was taking a while to get there.

  We didn’t have much to talk about in the car at first. I was still a little annoyed at Matt jumping in like that. I would’ve thought that if he saw me talking quietly in the corner with someone that he would have given me some space.

  I also didn’t know what to talk about.

  “If you’re mad at Matt, you shouldn’t be. He’s a good guy, and he means well. How long have you known him?” Jeff asked.

  “Too long,” I said.

  “At least, you have a good friend. I’ve only known him a year or so now, and I can tell that he’s one of the good ones,” He said.

  “I know he’s a good friend, but even good friends can be frustrating at times,” I said.

  “Point taken,” he replied.

  We were back to silence again. I tried to reconcile my thoughts as best I could. I could feel myself nearing my wits end, and not because of Matt in the slightest. It was like the culmination of everything that I’d been told not to do was driving me in a car towards a destination I didn’t know. I was scared and excited all at once, and mostly I wanted to know what I wanted.

  “It’s a ways, I know. But, the views of the city are spectacular,” he said.

  “I can’t wait to see it,” I said monotonously.

  We pulled off the main road and drove through a heavily forested area. Were it not for the tire marks in the grass I doubt I’d have had any idea where we were headed.

  I couldn’t fight my insecurity any longer.

  “Pull over,” I said.

  The car came to an immediate halt, and I leapt from the passenger door only to throw up behind a nearby tree.

  “Are you okay? Did you drink too much?” he asked.

  I held out a hand to quiet him and keep him away. I needed some space so I could breathe.

  I looked around at the nearly pitch black forest. I was more than a little frightened. Then I looked up. Through the line of trees, I could see little pinpricks of light occupying the night sky. I was in awe of how small I felt.

  I turned back to Jeff, who was leaning against the front of the car waiting for me. He perked up and walked over.

  “Feeling a little better?” he asked.

  I nodded and stood up, my head still swimming.

  “We’re actually here, already,” he said.

  I raised an eyebrow, confused with his statement. He just gestured to the other side of the car and beckoned for me to join him. I tip-toed my way around in the grass until I finally could see what he meant.

  We must have been about half a mile above the city, on the overlooking hills. I hadn’t seen anything so spectacular. It mirrored the night’s sky; the lights twinkled in the streets and cars zoomed around in the early evening.

  “I like to come up here when I have to think. I don’t know why I find it so relaxing to look down on everything,” Jeff said.

  “I can see why you like it,” I said.

  We sat on the hood of his car, just watching and taking it all in. I felt my anxiety that had built up during the car ride, start to fade away.

  I leaned over and gave Jeff a kiss on the cheek.

  “What was that for?” he asked.

  “I thought it was a good time,” I replied with a smile.

  He kissed me on my cheek.

  “What was that for,” I asked.

  “It felt like a good time,” he replied.

  I leaned and kissed him on the lips. He returned the kiss with a passion I hadn’t felt from any other man I’d been with. For a while, we were locked in an epic struggle of affection.

  I was incredibly lightheaded, but it wasn’t because of alcohol. I could feel the excitement taking hold of me, and I longed for more. I kissed down his neck, and I believe he understood what was on my mind.

  He wrapped his big arms around my back and pulled me in close. He kissed me deeper and more passionately. I could feel his hands rubbing up and down my back.

  I tip-toed my hand down his stomach until I reached his bulge, and felt it from outside his pants. The more I held, the larger it got.

  He lied back on the hood of his car and pulled me on top of him. I started ripping off his button-down shirt and kissing along his chest with each button I undid.

  He ran his hands through my hair, gently petting and pulling me in tight when he could. With his shirt off, I ran my hands along his chest sparsely covered with hair. I could see my breath, but I didn’t mind it in the slightest.

  Then I felt my zipper starting to come undone along the back of my black dress. I leaned back to offer the best view. It only seemed to stir him on further as my dress hit the floor seconds later. Standing there in nature, in only my underwear, I felt so free and open.

  My skin was covered in goosebumps, and I felt each one as Jeff ran his hands along my now exposed stomach. I reached behind my back, undid my bra, and slid it down my arms. He reached up and took my tiny perky nipples into his hands. I relished in the warmth that his hands brought.

  I pulled his pants off without much worry, and he just laughed as I did it; which in turn inspired a laugh from me. His member stood erect as he lied on the hood of the car. I reached down and took the shaft into my hands, massaging it up and down.

  I leaned in and took it into my mouth, and he moaned with pleasure as I did so. He was definitely the biggest I had been with by far. I continued to stroke his shaft while taking in as much to my mouth as I could. But, he pulled my head off and pushed me from him.

  “It’s my turn,” he said.

  He picked me up and slid me onto the car. With his other hand, he stripped off my underwear. Then, he kissed his way up my thigh and onto my hot sex waiting for him.

  I felt a small kiss at first, and then he started circling my clit with his tongue. The sensations were enough to drive me mad. I had to catch my breath on more than one occasion. I felt as though I might burst any second.

  He continued to play with my clit while rubbing along my little slit with his hand. I could feel myself gushing at each pass he made. Then my body tensed up, and I could feel a sweet release I hadn’t felt in a long while. The shock of it all was enough to make me quiver with excitement.

  He pulled himself off and started lining up his member with my ready womanhood. I was a little nervous, but I wanted it, I needed it. He rubbed the head along my little slit, and I could feel my juices pouring over him. Then I felt it begin to enter, small at first, but bigger and bigger as it continued.

  I threw my head back from the sensation. He continued to enter me, and I begged for more until he was completely inside. For a moment we just stayed there, enjoying each other. Then he began to thrust.

  He continued to rub his thumb on my clit as he worked his way in and out of me. All I could do was hold on to what little bit of the hood of the car I could to not be pushed away. His powerful thrusts hit me deep and each one shot pangs of excitement up and down my spine.

  Then the sensation I had felt earlier started overtaking me, except this time it was much deeper and more powerful. I couldn’t describe it, and the more I dwelt on it, the bigger it got. Then the sensation took over, and I began to quiver again with the most powerful orgasm I had ever felt.

  My muscles all tightened to the extreme; I panted to catch my breath, but it seemed nothing worked. I just gave in to the moment.

  He continued to thrust inside me until I could feel him release and collapse on the car next to me.

  I wanted to move, but my muscles were dead to the world. I stayed there trying to catch my breath. He did the same.

  “I like the view,” he said through heavy breathing.

  “Yeah, it’s not bad. We should come back here again soon,” I said.

  We laughed and leaned into each other for another kiss.

  5.

  I wanted to think t
hat things were going to get back to normal in school, but they didn’t. It was like something had clicked in my brain that night, and nothing seemed to make sense anymore. I couldn’t concentrate on classes.

  “I don’t know what to do Matt,” I said.

  “I still can’t believe you slept with Jeff,” he replied.

  “Can we change the subject back to the matter at hand?” I asked.

  “Well, I thought the matter at hand is that you slept with Jeff,” he replied.

  “No, the matter is that I can’t concentrate on anything. It’s like being caught in a whirlwind, and I can’t tell which way is up. I used to know what I wanted out of school and life, but now I’m just not sure anymore,” I said in an attempt to explain.

  “I don’t really know what to tell you then,” Matt said.

  “Well, tell me something at least,” I said.

  Matt sat there a moment, not really knowing what to say, or if he did know, he didn’t seem to have much interest in saying it.

  “Okay, look,” Matt started, “I didn’t want to say anything, and I was avoiding saying anything at the party, but I think Jeff is only interested in you to get to me.”

  I looked at Matt and rolled my eyes in disbelief.

  “Why would he do that,” I asked, “What does he have to gain?”

  Matt sighed.

  “I think he’s trying to use you to get close to me because he’s made it well known that he wants to be team captain. If he’s with you, there’s probably a better chance that he’d get it.”

  I laughed at first, but he didn’t join in, causing my laugh to quickly fade. He was truly serious.

  “You don’t really think that he’d use me to get to you. He’s a decent guy,” I said.

  “Tell that to the last girl that he dated,” Matt added.

  “What happened with the last girl,” I asked.

  “After they started dating, it wasn’t long before he was moved up to starter. Then they broke up.”

  “There must be a reason why they broke up that isn’t related to his moving up to starter, I just know it,” I pleaded.

  “Well then, you’ll have to get the truth out of him yourself. In the meantime, you should get back to work. You have a mock trial in just two days, and you need to be prepared for it,” he said, “I gotta get back to my own homework, Holly.”