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

by Luna Starr

  I glanced up at him and closed my eyes, letting him know I wanted him to kiss me. And he responded by taking my lips hostage immediately. His were so plump, so soft and when they parted to allow his tongue entrance into my mouth, I heard myself moan. I met his tongue eagerly as I tasted him, wanting to consume him whole.

  “Jessica,” he started in a worried tone as he pulled away from me. “Baby, I want this, I do, but I’m worried about you,” he said as I shook my head. But he silenced me with his fingers on my mouth. “I don’t want you to do anything you don’t want to do.”

  “I want to experience everything with you,” I said. “I’m sure of that.”

  But he didn’t look convinced. In response, I took a few steps away from him and started unbuttoning my shirt. Mr. Jacobs swallowed hard, his eyes on mine. I glanced down at his crotch and noticed his cock was hard, the outline large and bold. He took a step forward and pulled my shirt over my head with a fervent yank. And with his other hand, he began pulling up my long skirt, draping it over his forearm as he gently squeezed my ass with his brutish hand. His grip was strong and sensual, his conditioning evident even through the tips of his fingers.

  “Jessica, I’m at the point that I can still stop this,” he breathed. “But soon I won’t be able to.”

  “Shh,” I said, feeling suddenly strong, courageous and proud of my body. He wanted me—it was as clear as the desire in his eyes and the straining cock in his pants. And that knowledge imbued me with a confidence I had never felt before, one that thrilled me to my core. “I want to feel your touch,” I whispered to him.

  I wanted to experience his fingers again, to allow him to explore my body and to explore his. I wanted to know him—what he felt like, what he sounded like, what he tasted like. I wanted to know him.

  He reached down and ran his fingers over my panties as I arched and threw my head back, moaning out loud as soon as he passed by my clit. I spread my legs further apart for him so he would have an easier time of touching me.

  “Your pussy is soaking wet,” he whispered into my ear with a growl.

  “I’m sorry if I’m too wet,” I said suddenly, feeling embarrassed as I wondered if there was such a thing as being too wet.

  But Mr. Jacobs’ brow was crinkled in lustful concentration as he peered down at me. “Don’t ever apologize for anything your body does again,” he said, his voice deep. “You are pure beauty and you turn me on like I’ve never been turned on before.” He pushed my panties to the side and started rubbing my sopping wet clit as I gyrated my hips against him. “And this pussy is so perfectly wet. Just the way I want it.”

  With his other hand, he rubbed my thigh, squeezing it intermittently. My skin was sensitive in that area of my body, which triggered more of my natural lubricant to seep through my cotton panties. As if realizing they were still there, he brought his hand away from my clit and gripping my skirt and panties by the hemlines, pulled them both down my legs until they pooled on the floor.

  Then he lifted me up and I wrapped my legs around his middle as he brought me down to the ground, so my ass was resting on top of my skirt. He unwound my legs from his middle and then spread them, looking down at me with an appreciative expression on his face as he kneeled above me.

  “Your cunt is beautiful, shining wet in the moonlight,” he said, his voice barely audible.

  He reached down and began circling my asshole with the tip of his finger, rubbing my own juices around it. I had never felt anything like it and I wanted to cry out with pleasure but I bit my lip instead because I didn’t want to be too loud that I might alert someone to where we were or what we were doing.

  “I want to watch those tits bounce,” he said as he reached around and unclasped my bra, pulling it down my arms before freeing it completely and depositing it on the ground next to us. Then he gripped me by the waist and rocked me up and down, his eyes plastered to my breasts. “God,” he groaned.

  He let go of my waist and reached for each of my breasts, plying them in his hands before he began pinching my nipples lightly at first and then harder as I moaned beneath him. Then he gripped me around the waist and lifted me up as if I didn’t weigh a thing. He flipped me around so I was on my hands and my knees, my ass in the air. Then he gripped both of my thighs and worked his hands up to my ass cheeks, separating them from each other, spreading them. His moist tongue began encircling my asshole as I bolted forward, shocked and amazed. His tongue felt amazing as it brushed the lower end of my vagina, then up toward the nerve endings of my asshole. I had never imagined in a million years that my ass could feel like this.

  “Do you like that, babygirl?” he asked as he leaned forward and bit the lobe of my ear gently.

  “Oh, yes, Mr. Jacobs,” I mewled back at him, clenching my eyes shut tightly when I felt his fingertip rubbing my tight asshole again. He edged the very tip inside of me as I jolted forward.

  “There there,” he crooned to me as he wrapped his arm around my middle to hold me in place. Then I felt his fingertips on my pussy, spreading my lips apart as he rubbed my wet hole. I moaned against him, my whole body feeling like it was on fire. When he rubbed my clit with one hand and pushed more of his index finger into my asshole, I bucked underneath him.

  He started rubbing my pussy opening again and then inserted the tip of his finger into my throbbing hole. I began panting wildly as he pushed his finger in even deeper so he was up to his knuckle. He began rubbing the roof of my vagina as his other finger continued probing my asshole.

  “Tighten your cunt around my finger, beautiful,” he whispered. “It’s already so tight and I want to feel you clamp down around me even tighter.”

  I wasn’t sure what he meant but I attempted to tighten my pussy muscles around him by bearing down and clenching my thighs tightly. I felt his middle finger as he pushed it in beside his index finger and started fucking me shallowly with both of them.

  “Bear down against me, baby,” he whispered as I tightened my pussy. “Mmm, that cunt is so tight and its gushing all over my hand,” he said as I bore down even harder, wanting to please him.

  He held me firmly in position, half his finger buried in my ass while he thrust his other two fingers in and out of my cunt. I was so wet, the friction between his fingers and my pussy lips began making a noise like when someone tries to squeeze the last bit of lotion out of a bottle. I was embarrassed by the sound for maybe a few seconds.

  “That’s the sound of a wet and tight cunt getting fingered so good, baby,” Mr. Jacobs groaned at me. “I want to hear that sloppy snatch get even louder,” he said as he added a third finger to the first two and spread me as my eyes went wide. He burrowed his three fingers into me halfway, pulling them out and shoving them in again in quick succession as my pussy slurped in response.

  My eyes rolled toward the back of my head as he continued his rhythm, his fingers buried in my pussy and my ass. My hips and ass trembled slightly, as I felt a surge of sensations channeling through my pussy lips to the top of my pubic area and deep inside my core. The shuddering increased as a wave of bliss shot through me and I clenched my eyes shut tight as I moaned out loudly, the orgasm cresting through my body. When I opened my eyes, I was panting and Mr. Jacobs was smiling down at me.

  “How did that feel, babygirl?” he whispered.

  “Amazing,” I answered as I took a deep breath. But then, it wasn’t enough. I wanted more. “I want to see your cock,” I said as I opened my eyes and found Mr. Jacobs staring at me.

  Mr. Jacobs didn’t say anything but stood up as his erect dick protruded through the light fabric of his pants. I sat up and slipped both of my index fingers underneath the elastic of his waistband and slipped his pants down toward the floor. His long, thick and erect cock was staring at me, right in front of my face. He was carefully trimmed and clean, fully erect and enormous. I felt myself gasp as I gazed at every inch of him.

  I gripped his cock with my lithe hand; lifting it and exposing his shaft to the moonlight. His
lovestick was rigid but the skin was smooth, the base exquisitely thickened and grooved. His cock reminded me of Tommy’s. And I remembered touching Tommy’s dick, jacking him off in the Jacuzzi. Suddenly, I wanted more with Mr. Jacobs. I wanted to taste him, to take his gorgeous cock inside my mouth. I leaned forward and placed my tongue on the center of his shaft, licking upward toward the base of his large, engorged head. He threw his head back and moaned. And I was exhilarated by the thought that I was controlling him—that whatever I was doing was eliciting this response from him.

  When I reached his mushroom head, I thrust the whole thing inside my mouth and began sucking. I didn’t know what I was doing, so I welcomed Mr. Jacobs’ intrusion when he gripped either side of my head and started moving my head up and down on his shaft, teaching me how he liked his dick sucked.

  “Keep it slow and press against it with your tongue,” he instructed me.

  I licked the curved underside of his dickhead and pressed my tongue hard against the fleshy bulb. His hips began squirming as his breathing hitched. His pants were measured, deliberate, and airy.

  His voice grew coarser with each lick of my tongue. “Don’t stop... keep going, baby.”

  I reached down and began playing with my clit as I sucked Mr. Jacobs’ dick. My moisture was overwhelming as I felt it drip down my hand. I pushed one of my small, slender fingers inside of myself to feel what Mr. Jacobs had felt. And what I felt was a tight, wet and eager cunt. A cunt which wanted to be fucked by a huge cock, the huge cock that was currently in my mouth. I finger-banged myself while holding Mr. Jacobs’ cock in my mouth as he trained it in and out.

  “I want to fuck you, babydoll,” he said loudly as he thrust in my mouth over and over again. “I want to slide into that slick cunt.”

  But I wasn’t ready to have sex. Not yet. Mr. Jacobs was right, I needed to think about it before I committed myself to something I could never take back. And for now, it was enough for me to taste him, to feel the heavy weight of his shaft in my throat. But there was more than just that. There was also a burning curiosity inside of me that wanted to desperately see Mr. Jacobs’ cum. I wanted to watch how far he could shoot his white, viscous cream and I wanted it to explode all over me.

  The underside of his shaft began to spasm softly as his moaning increased. His shaft rose up and within a split second, the head of his cock contracted as if it were a charley-horsed thigh muscle. I pulled my mouth away so I could watch his cock cum. No sooner did I free my mouth than a jetting, warm stream of liquid shot onto my upper lip. I opened my mouth, wanting to taste his love juice and this time, that cock shot cum into my mouth, hitting the back of my throat. His dick moved up and down with each shot of cum. Mr. Jacobs moaned uncontrollably as I then covered his entire head with my wet lips. I stroked his hard, pulsating rod as I tried to suck out every last bit of semen into my mouth.

  “Stop, stop... fuck,” he said, as he placed his hand on my shoulder.

  “What?” I asked, as I wiped his thick cum off my lips and swallowed it all, loving the taste of him. His eyes were wide as he watched me.

  He pulled away from me and stroked his cock a couple more times. Two clear droplets of his cum sloughed off the tip of his head, hitting the ground like raindrops. He staggered backward. His back thumped against the shack’s wall, giving it a shake as if it had been struck by a small earthquake. In repose, he slumped downward to the ground, holding his dick in the process.

  I was still crouching on the ground after Mr. Jacobs’ magmatic event, my pussy exposed and feeling stretched and distended. Realizing it was late and not wanting Sister Janice to wonder where I was, I grabbed my panties and started putting on my long skirt. Mr. Jacobs just watched me, still fighting to catch his breath.

  “You are amazing, Jessica,” he moaned after a few seconds. “Absolutely incredible.”

  I didn’t say anything but I beamed with pride as I put on my long skirt and buttoned my shirt. Then Mr. Jacobs put his cock away and zipped up his pants as he stood up. He reached a hand out to me and I took it as he yanked me to my feet and pulled me into him. He smiled down at me before claiming my lips and kissing me with a passion that hadn’t died away with his ejaculation.

  “I’m going to make you mine,” he said as he pulled away from me. “One way or the other.”

  Chapter Thirteen

  Jessica

  The next day, I didn’t see Mr. Jacobs.

  He’d been assigned to work on a different house than Tommy and me, who had been paired together. And I was actually grateful because I was confused about my feelings for Mr. Jacobs. I wanted him. And that scared me. But, what scared me, even more, was that I didn’t know if I could trust my own feelings. I wasn’t sure if maybe I just wanted him because he was older and refined and knew so much more than I did or if I legitimately cared for him. So, I thought it might be useful to spend some time one on one with Tommy, the boy I’d always had a crush on. I figured if my feelings for Mr. Jacobs still remained unchanged, then that was telling me something.

  As Tommy and I worked side by side in the heat and the dirt, we joked, laughed and actually enjoyed ourselves, which was a surprise to me, given the strenuous work we were doing. Father Anton was overseeing us—as well as a host of other volunteers—which meant he was so busy, he mostly left us to supervise ourselves. And that was just as well because I wanted to spend time with Tommy alone.

  So far, I found myself enthralled with Tommy, just like I always had been. He was so charming and so boyishly handsome. Where his father was chiseled, worldly and sophisticated, Tommy was daring, brash and irreverent. They were both so different and yet I saw in each one characteristics I found so appealing. I almost wanted to be so attracted to Tommy that I talked myself out of Mr. Jacobs but the more time I spent with Tommy, the more I realized spending time with him didn’t dissuade me from my interest in Mr. Jacobs at all. I appreciated both of them, for different reasons.

  At the moment, Tommy and I were piling mud bricks in a row to build the walls of a home for a family of seven. The bricks had been previously created by mixing mud and water and then pressing the mixture into the form of a brick. Then the bricks had been left to harden in the sun for a few days. Once we got the bricks in place, we mortared row after row. In a few days, we would start applying plaster to them before painting them.

  “Do you remember that time in my dad’s Jacuzzi?” Tommy asked as he glanced down at me with a devilish smile.

  “Of course,” I said as I returned the secretive smile, memories returning again as if it had been only yesterday that I’d been stroking his beautiful cock until he came all over me.

  “Do you ever think about that night?”

  “Yes,” I answered, seeing no point in lying. I had thought about Tommy and that evening almost every day since it had happened, both with guilt and wistful excitement.

  “I think about it all the time,” Tommy continued as he turned to face me earnestly. “And I also think you’re beautiful, Jessica,” he finished. “I can’t understand why we never hung out before, or how I never noticed you.”

  “We were from different crowds, Tommy,” I explained with a shrug. “You know that.”

  “I guess,” he answered and then sighed. “But it doesn’t change the fact that I’m bummed all of this,” and he pointed to himself and then to me, “happened so late.”

  “Late?”

  “Well, since we both have graduated and I’m going to college and you’re heading off to college, it’s just a bummer. I feel like had we known each other better a long time ago, maybe we could have been something together.” He shrugged as if he was worried he sounded stupid. “You never know.”

  “That’s true,” I answered but then gave him a smile. “But be grateful we’re spending time together now. I know I am.”

  “Believe me, I am too!” he answered with a large smile as he piled the last brick in the row and I tapped it into place.

  “I’m glad you came with us, Tommy,
” I said as butterflies started to blossom in my stomach. I was confused because I suddenly wanted Tommy just as much as I’d wanted his dad. And I knew I wasn’t supposed to feel this way. It was bad enough to crave one man… but two? And not only that, but a father and his son? God, what was wrong with me?

  “Actually, it’s crazy that I’m saying this but I am too,” he said as he glanced down at me, surprise echoing in his expression. “It’s weird since we’re out in the middle of nowhere and it’s hot as balls and the mosquitoes are enough to make me want to kill myself, but I’m actually having a good time with you.”

  I laughed because everything he was saying was spot on. “Yeah, me too.”

  Then we both fell quiet as we started our next row of bricks. I felt the sweat starting to bead down the small of my back so I reached around and pulled up my T-shirt so I could sop up my sweat with a rag I’d been wearing around my neck. I caught Tommy as he watched me, his gaze lingering on my ass.

  “Would you ever let me touch you?” Tommy asked as he eyed me and shock traveled through me because he was so unabashed with his question. “The way you touched me?”

  I swallowed hard as my pussy began to throb and I thought about him looking at it, touching it, kissing it. “Yes,” I said as I studied him, regretting my own honesty. I knew I shouldn’t encourage him—that I should have stayed on my own course, thinking about anything but sexual things. But I was starting to wonder if that was even possible. Since coming on this trip, all I’d been thinking about were sexual things involving Mr. Jacobs or Tommy. And I couldn’t seem to stop.

  Tommy nodded as he smiled first to himself and then to me. “At lunch, I want you to meet me at the abandoned school, okay?” he asked as we both spotted Father Anton who was walking up to inspect our work.