Cowboy Up: A Contemporary Romance (The Cherry Series Book 1)

by Luna Starr

  “Okay,” I breathed as I wondered what I was getting myself into. And, what was more, what would Mr. Jacobs think if he ever found out? And what would Tommy say if he knew I’d already been intimate with his father? I didn’t want to know the answers to my questions so I forced them back and focused on mortaring my row of mud bricks as I wondered what was becoming of me. Ever since that party at Tommy’s house, I felt like my life was spinning out of control. I wasn’t the same girl I used to be. I was different. And what scared me the most was that I liked this new me. A lot.

  ***

  The abandoned school had been a structure that had been in use by the village for years before the walls started crumbling and falling down and a new school was built in the center of the village under Father Anton’s watch. It was just a matter of time before they pulled this one down altogether because it wasn’t safe.

  As I waited for Tommy in what was once one of the classrooms, I was nervous. But I was also anxious and excited to see him. I needed to understand my feelings for him so I could better understand my feelings for his father. I figured if I felt more strongly for one over the other, then that would give me the answer I was searching for. And I was hopeful to reach a conclusion soon because these feelings were so overwhelming and confusing, they were starting to suffocate me.

  When I watched Tommy walk into the classroom, my heart rate increased. He was beautiful—so tall and broad and muscular. He strode up to me immediately and didn’t say anything. My heart was thundering against my ribs as I stood there, watching him approach me. Without any warning, he gripped me by either side of my head as he threw his lips down on mine, kissing me with a passion that surprised me. I opened my mouth to him and felt his tongue invade me. He tasted so good and he felt even better.

  “I want to explore you,” he said as he lowered me to the ground and smiled at me. He brushed my hair to the side and looked at me as if he were seeing me for the very first time. “Is that okay?” he asked.

  “Yes,” I answered as he pushed my T-shirt up so he could see my breasts. He unfastened my bra in record time and then lowered his head as he took one of my nipples into his mouth, sucking on it gently as my nipple hardened and my pussy began to gush. God, I wanted him just as badly as I’d wanted his father.

  What was wrong with me? I didn’t understand how it was that I couldn’t make up my mind but it was frustrating, to say the least. The sound of footsteps interrupted my jumbled thoughts and my heart kicked into overdrive. It felt like time slowed down to a crawl as I turned my head to the side and found Mr. Jacobs standing above us, looking down at me with an amused smile. Tommy sat up immediately, shocked to see his father.

  But Mr. Jacobs didn’t appear to be angry. Instead, he glanced at both of us and continued to smile, like he knew something we didn’t.

  “Grey?” Tommy asked as he faced his dad with irritation mixed with shock.

  “Tom,” Mr. Jacobs responded in greeting as he walked past his son and extended his hand to me. I took it and he pulled me up so that I was standing in front of him and we were both facing Tommy. Mr. Jacobs brought one of his hands to my breast and started rubbing it as my nipple instantly hardened and a rush of guilt flowed through me. How wanton was I that it turned me on that Mr. Jacobs was fondling me in front of Tommy? I wondered what was going on inside my head, what was wrong with me to make me think such dirty thoughts? And why, no matter what, I couldn’t stop these lustful feelings? No matter how hard I tried to stay the course and be a good girl, I just wasn’t strong enough.

  “It seems we both want the same woman, Tom,” Mr. Jacobs said at last as the breath caught in my throat and I didn’t know what I should do. Were they going to argue? Fight? Ridicule me for being interested in them both?

  “What?” Tommy started as he shook his head and alternated his confused gaze between his father and me. “What are you talking about?”

  “I have feelings for Jessica, Tom,” Mr. Jacobs said with no amount of apology. “And it seems you have feelings for her, as well. True?”

  Tommy gulped, his eyes wide—I assumed at Mr. Jacobs’ announcement that he had feelings for me. I felt like I was stuck in the middle of a Jerry Springer episode—er, in the middle of Africa.

  “Yes, I guess I do too,” Tommy answered, looking like he was slightly confused.

  “More than what we previously discussed?” Mr. Jacobs asked his son as I wondered what was going on. They’d already had a discussion about me?

  “Yes, more than what we discussed,” Tommy replied as he glanced down at me, almost like he regretted having feelings for me but couldn’t help them all the same.

  Then Mr. Jacobs leaned over to look me in the eyes. “And it seems our sweet, little, innocent Jessica wants us both?” he asked me as I wondered why he wasn’t angry over that fact. “Is that true, beautiful?”

  “Yes,” I breathed as I hung my head in shame, refusing to look either of them in the eyes because I was so mortified. “I tried to pick between you both but I couldn’t and I can’t.”

  “No reason to choose, beautiful girl,” Mr. Jacobs said as he faced his son again. “Tom, she wants us both and so she should have us both.”

  Tommy stood there for a few seconds, not saying anything as he just looked at us both in bewilderment. I was sure he was in the process of making a decision for himself and I couldn’t help but hope he would agree with his father. Suddenly I couldn’t think of anything more perfect than having Mr. Jacobs and Tommy for myself. Together. At the same time.

  A rush of shame swept through me as I wondered what had become of the level-headed girl I used to be. Instead, all I could think about were these two men. Every thought, every daydream I had centered around them. And I couldn’t seem to purge the filthy images from my mind. What was more, I didn’t want to. The rush I got from experiencing them, from touching them, from thinking about them was addictive. I felt more alive than I had ever felt before. And I loved it.

  “Well, Tom?” Mr. Jacobs asked his son.

  “Jessica, is this what you want?” Tommy asked me as I swallowed hard. I didn’t even need to think about it.

  “Yes,” I answered immediately.

  Tommy just nodded and then he started to approach me. I heard Mr. Jacobs chuckling as he leaned down and began kissing my neck. “We are going to take care of you, baby girl,” he said as shivers raced up and down my spine.

  Tommy gripped my face again and kissed me as his father pinched my nipples and started working down my body, removing my clothing as he went. When I stood there, naked in front of both of them, they each stood back and admired me as I felt color stain my cheeks. I was embarrassed but I was also experiencing a sense of confidence I never had before.

  Mr. Jacobs unbuckled his pants and his enormous cock bounced out, fully erect and engorged. As soon as I saw it, my pussy started pulsing and I could feel it swelling, growing wetter. I dropped down to my knees and took his beautiful cock in my mouth, tasting his pre-cum as it bubbled out of him. And I loved the salty taste, loved the flavor of man that dripped onto my tongue.

  Tommy strode up next to his father and dropped his shorts, his glorious dick spilling out only seconds later. I eagerly gripped it and started rubbing it up and down, taking turns sucking them both and loving the feeling of their cocks slamming into the back of my throat.

  My cunt was soaking wet with my juice and I could feel it streaming down my labia. I reached down and started fingering my clit and moaning on Mr. Jacobs’ cock and then Tommy’s.

  “Put your finger in that tight little cunt, babygirl,” Mr. Jacobs said as I glanced up at him while I sucked his huge shaft. I obediently shifted my index finger to my drenched hole and shoved it inside of myself as I bucked forward, plunging his shaft all the way to the back of my throat. I felt my saliva building up as Mr. Jacobs shoved his cock so deeply into my mouth that I started to gag and my eyes watered. His, meanwhile, rolled to the back of his head as I intensified my strokes, sucking his cockhea
d with feverish need.

  “I want to see her,” Tommy said between raspy breaths as I released Mr. Jacobs’ cock and turned to suck Tommy’s. But he pulled his dick away from me even though he was still panting. “Show us the inside of you, Jessie,” he ordered me.

  I nodded and then leaned back as I spread my legs in front of both of them. I moved my hand down my thighs slowly until I reached my pussy which was so wet, my upper thighs were slick. I pulled back my pussy lips, exposing my hard clit from its swollen, fleshy hood. I started rubbing the ultra-sensitive skin that surrounded my clit as my breath hitched and my heartbeat accelerated.

  “Yes, baby,” Mr. Jacobs said as he rubbed his dick in time with my own rhythm.

  “I need one of you inside me,” I managed as I looked from one to the other. Even though I had always promised myself I was going to wait to have sex until I was married, I now realized how ridiculous that thought was. I wasn’t going to wait. I couldn’t wait and what was more, I no longer wanted to. I was a woman and I wanted to experience a man, men. I wanted to know what it felt like to feel a penis inside of me, to watch a man as he experienced my body. I wanted to understand what it really meant to be a woman.

  And now that time was going to come. In response, Mr. Jacobs approached me and reaching down, he picked me up, the muscles in his arms straining and flexing. He wasted no time in placing me on one of the dusty tables that stood in the corner of the dilapidated room but not before running his hand over the wooden surface to test it for splinters.

  “Are you sure you want this, Jessica?” he asked me, his eyes searching mine. “I don’t want to do this unless you are convinced.”

  “I’m convinced,” I answered with a quick nod. “I want this more than I’ve ever wanted anything.”

  Like a hungry animal, he growled low in his throat as he placed his large hands on the back of my thighs and pushed my legs up toward my head so my pussy was spread out wide in front of him. Then he crouched down, his long, massive penis brushing against the wooden corner of the table. He leaned down and began licking my moist, glistening pussy as Tommy watched.

  “Tommy, I want your cock in my mouth,” I grunted and Tommy wasted no time in approaching me. Once he was in front of me, I reached down and took hold of his smooth balls which hung behind his massive shaft. The skin of his balls was shriveled and tight, and his balls were so round, so full of cum. I couldn’t wait to milk them, to watch that cum shoot out of his gorgeous dick and onto my body or into my mouth. I gripped his long cock and pulled it toward my mouth as Mr. Jacobs was still diving into my pussy, his tongue circling my clit and inching up into my cunt hole. My lips surrounded Tommy’s hardened shaft as I worked my way up to his ripe head.

  Tommy began squirming and thrusting his cock in my mouth violently, treating it as if he were fucking my wet pussy. Mr. Jacobs stood up then and smiled down at me as grabbed his thick cock and inched closer toward my hole. I reached down and gripped his cock as Tommy continued to fuck my mouth. I guided Mr. Jacobs’ enormous shaft to my wet, pulsating pussy and then released it. He pushed just the head into my sopping wet hole as I arched up against him and moaned out because the feel of his head was better than I’d ever imagined it could be. It was as if every nerve at the opening of my cunt was poised, receiving the feelings of the cock that was stretching it. I clenched my eyes shut tight against the gagging feeling in my throat from Tommy’s dick.

  “Mmm, tighten that cunt around me, babygirl,” Mr. Jacobs moaned as he pushed his mushroom tip in just a little further and I tightened my pelvic muscles around him. I could feel my cunt stretching around his girth as my body bathed him in another wave of cream and juice. He pushed his dick in even further until the entire head was now inside of me.

  “I can feel that hymen, babydoll,” Mr. Jacobs said as he pushed his huge dick further inside of me and then paused.

  “Break it,” I breathed, trying to bear down on him but he held me in place.

  “I want to feel it,” Tommy announced as Mr. Jacobs glanced over at him. “I want to feel her virgin pussy.” Mr. Jacobs nodded and pulled his cock out of me.

  “Don’t break it,” Mr. Jacobs warned. “That’s for me.”

  Tommy just nodded and positioned himself at my opening before sliding the head of his cock into my stretched hole as I bucked underneath him. He pushed in a little further as his eyes rolled back and he gripped either side of my hips.

  “Fuck, she’s so fucking tight and she’s so wet, she’s drenching my dick.”

  “Please,” I moaned as I rocked my hips underneath him. “I want you all the way in me.”

  “Soon, baby,” Mr. Jacobs responded. “Suck your juice off me first,” he ordered as he held his cock to my mouth and then shoved it inside once I opened my lips to him. I sucked my pussy cream off him, loving the flavor of my sexual juice.

  I glanced back at Tommy who was doing his best to fuck me with just the tip of his dick. He was tense and deep in concentration, his eyes closed and the look of intense pleasure plastered across his face. Mr. Jacobs pulled out of my mouth and tapped Tommy on the shoulder.

  “She’s ready for me,” he insisted. “I’m going to bust through that virgin flesh.”

  Tommy opened his eyes and pulled out of me as Mr. Jacobs slid back just his head back in. I felt myself shiver at his words as my pussy gushed even more, ready to be impaled by two huge cocks.

  “I’m going to pop that cherry now, babygirl,” he said as he eyed me. “Are you ready for me?”

  “Yes,” I hissed as I lifted my hips and he gripped my ass cheeks, guiding my pussy down his shaft. Tommy, meanwhile, watched as he stood beside me, stroking his cock, which shone with my juice.

  Mr. Jacobs gripped my ass cheeks even more tightly, pulling my ass upwards and then he shoved that monster dick all the way into me. There was a moment of shrill pain as he broke through my virginal wall and I heard myself cry out in protest.

  “I’m sorry, baby,” he moaned. “It will get better,” he finished as he pulled his cock all the way out of me before shoving it back in again. And then the pain was forgotten, a thing of the past. It was replaced with pure bliss.

  My pussy lips began spasming, as I let out a scream and gripped Mr. Jacobs’ ass so his cock was buried all the way in me. I could feel my entire body shaking as I rode my orgasm. Mr. Jacob’s groans intensified and he pulled out his dick which was dripping with my cum. He brought his dripping cock to my mouth and I immediately put my lips over the veiny shaft and stroked it vigorously. Meanwhile, Tommy shoved his dick inside of me and thrust in all the way until he was buried to the hilt. And then he pulled out and started fucking me in short, hard thrusts that made my heavy tits bounce up and down.

  “That fucking pussy feels so good,” he groaned, his eyes closed in deep pleasure.

  Mr. Jacobs continued to work his dick in my mouth as he stared at me, watching me take his huge cockhead. Suddenly, his cum gushed into my mouth, surprising me. Wanting nothing more than to taste him, I eagerly lapped it up, swirling it around my mouth as I sucked the remnants from his head. And I loved it. Loved every drop of that load that spurted into my mouth. As I pulled his dick out, cum dripped from the tip of his head and down the side of my mouth.

  Suddenly Tommy pulled out of me and sprayed cum all over my stomach as I glanced down and watched him, loving the feel of the reels of hot jizz that landed all over me. I reached down, spooning some of it up with my fingers and then brought his white cream to my mouth, sucking it off my fingers as my pussy throbbed.

  Epilogue

  Jessica

  One Year Later

  It was the end of my freshman year of college.

  Mr. Jacobs had just taken me out for a celebratory dinner at our favorite restaurant. And now we were on our way back to his house, our house. Yes, I had moved in with him and I’d done it pretty much as soon as we’d returned from our trip to Africa. My parents had been pretty shocked and at first, they weren’t exactly happy with t
he arrangement. But once Mr. Jacobs had assured them that we were in love and he intended to take care of me, they still weren’t happy but they calmed down some.

  As for me? I was happier than I could ever remember being. Even though Mr. Jacobs and I weren’t married, I couldn’t say I cared. Because what we had was so deep, so intense that something as flippant as a piece of paper couldn’t compare. We were in love and it was the most amazing feeling—like walking on clouds.

  “I’m proud of you, Jessica,” he said as he unlocked the front door and pulled me into him, kissing the top of my head.

  “Thank you,” I said with a secretive smile as he opened the door for me and I walked inside. Almost immediately, I noticed Tommy sitting on the black leather couch and drinking something from a tumbler. He was home for summer break so it wasn’t a surprise to see him.

  “Grey, Jess,” he said in greeting. “Hope you don’t mind that I let myself in.”

  “Hi, Tommy, when did you get in?” I asked as I walked up to him and gave him a hug. He was just as handsome as I remembered, only he seemed older somehow. It was amazing what one year of college could do for a person because Tommy seemed more sophisticated somehow.

  “A few hours ago,” he answered as his arms lingered around me.

  “Tom, good to see you,” Mr. Jacobs said as he greeted his son and Tommy released me. He stood up and walked to the kitchen, taking his glass with him. “How were finals?” Mr. Jacobs continued.

  Tommy shrugged. “As good as could be expected,” he answered as he flashed me a cheeky grin and I just shook my head. No doubt, he’d found some little Brainiac to cheat off. That was Tommy, always working the system in a way that the system didn’t realize it was being worked. He refilled his glass and then walked back into the living room, striding right up to me. He reached around and grabbed a fistful of my ass.