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

by Luna Starr

  In the center of the room was a king-sized bed with a solid oak, gray-washed headboard; the dresser, armoire, and the nightstands also were made of the same expensive-looking carpentry. The television in the bedroom was larger than any television we’d ever owned. It was obvious that Grey Jacobs liked to live life to the fullest.

  Chrissy shut the door behind us and immediately took off her skirt and shirt all within seconds of each other. Luckily, she didn’t take off her bra and her cotton thong. She had a nice set of perky B-cups, her butt and hips matched her tiny frame. She ran into the bathroom and wasted no time in getting into the large, marble hot tub. The thing was so huge, it could easily accommodate all of us. It didn’t even look like a bathtub, more like a Jacuzzi.

  “Come on guys!” she insisted, as she activated the jets.

  “She’s such a show-off,” remarked Gloria, with a slight look of envy.

  Jason, Steve, and Tommy all took their shirts, pants, and shorts off. Every single one of them had incredibly built torsos and legs. Jason’s thighs had that neat little cut in the middle, while Steve proudly displayed his eight pack, something I had to see to believe. His body fat was so low, his lower abdominal muscles created a perfect “V” shape that made it impossible not to naturally scope out his groin area. Gloria and I caught each other looking at his lower torso and smiled at each other like sinister schoolgirls.

  Tommy’s body was from another world, though. His pecs were perfectly cut and rested over the statuesque, muscular veneer that padded his ribs. His skin, young and without blemish, displayed soft, golden bristles. He gave Steve a haughty look, as Steve playfully pretended to attempt to take off his boxers.

  Jason plopped himself into the hot tub first; well, technically, right after Chrissy. He nestled himself right behind her in the far corner of the tub. Tommy and Steve soon followed. Tommy quickly dipped his head in the water, and like a model in a shampoo commercial, sensually smoothed the water from his scalp with his large hands.

  “Girls?” asked Steve. “You coming in?”

  The group in the Jacuzzi stared at us intently, waiting for us to unravel our supple physiques for arbitrary judgment.

  “You first,” I pointed at Gloria.

  “Me?” asked Gloria, pointing at her chest. She sighed and took off her matching black tank top, revealing a Victoria’s Secret silk bra. The boys looked at each other with cheesy smiles. Chrissy, buzzed and severely bombed, smirked and shrugged her shoulders. Gloria then dropped her tight, black designer jeans. Thankfully, no thong, just a pair of good-girl cotton, black panties. The boys were definitely impressed with her sprint-chiseled legs and thighs. In a sudden rush, Gloria stutter-stepped and quickly dipped herself into the tub.

  “Jess, you coming in?” asked Tommy in his deep, rich, confident, baritone timbre.

  “I don’t know,” I said, as I sat down on the chair just beside the doorway. “I think I’ll just sit right here and chat with you guys.”

  “Don’t be such a bore,” said Chrissy with a yawn and a dismissive wave of her hand.

  “Jess, just get in here. We’re just hanging out and drinking,” said Gloria. “You can keep your panties and bra on.”

  “I will take my briefs off if you don’t get in here this instant, lady,” Steve joked.

  “You promised, Gloria,” I said, giving her a look that hopefully would make her remember our promise.

  “Promised what?” asked Steve.

  “It’s nothing. She’s just grasping at straws and thinking of excuses for not joining us,” Gloria said as she frowned at me. “Trust me and trust them, it’s all innocent.”

  “We’ll close our eyes as you undress,” suggested Tommy. “No one will look, promise.”

  “Promise?” I asked.

  “Steve, Jason? Close your eyes,” demanded Tommy.

  Jason and Steve chortled and closed their eyes, mockingly tight. Tommy soon followed.

  I quickly pulled the straps off my dress and unzipped the back, being careful to pull it down my body. The boys, pretending to have their eyes closed, definitely caught a glimpse of me in my black lace bra and matching underwear, as their snorts and giggles stopped all of a sudden. I caught Steve letting out a barely audible “wow.”

  I slowly stepped into the hot tub. The water was exceedingly hot, but within seconds, it went from uncomfortably hot to a nice adequate temperature, as my body adjusted to the fluctuation from outside and in. “You can open your eyes now,” I said.

  “Um, our eyes have been open,” Tommy announced with a wince, as if he were afraid I would get mad at him.

  I took a deep breath but then smiled at him. “Yeah, I kind of already figured.”

  “For being such a prude, you have an amazing pair of tits,” said Chrissy. “I’m almost jealous.”

  Gloria laughed and said, “Is that even a compliment?”

  “I mean, she’s got the greatest pair of tits I’ve ever seen,” joked Steve but by the way he was looking at me, it was fairly obvious it wasn’t a joke. “Of course, I can’t say for sure because she’s still wearing a bra.”

  “I think you should take your bra off,” Chrissy said to me.

  I began blushing. “Maybe I should get out,” I said.

  “Okay, I’ll stop. Just finish your margarita. Don’t let a perfectly good drink go to waste, if you know what I mean,” said Chrissy, as Jason began to give her a back rub and she leaned back against him.

  “So who wants to play truth or dare?” she asked suddenly, leaning forward with interest.

  “No... no... no,” I said.

  “It’s okay, I promise it will be clean,” Chrissy insisted.

  “You promise?” I asked, facing her squarely. All I could think about was the promise that I’d made to Mr. Jacobs.

  “Yes,” Chrissy answered. “Scout’s honor,” she added as she held up three fingers. “Here, I’ll start. Jess, truth or dare?”

  I felt my heart drop and hoped no one would ask me anything about Tommy’s dad. And then I realized the chances of that were like slim to nothing. “Truth,” I said hesitantly.

  “Okay, do you think Tommy is cute?” Chrissy asked with girlish enthusiasm.

  “Chrissy...” Gloria snapped at her.

  Chrissy looked at Gloria with her bloodshot, droopy eyes. “It’s an innocent question!”

  “It’s fine, Gloria,” I said as I looked at Tommy. I took a deep breath. “Anyone would agree that Tommy is undoubtedly handsome.” Well, he was, so it wasn’t a big deal speaking the truth, I thought.

  “Well, thanks, Jess. You are very pretty yourself,” said Tommy as he smiled at me and dropped his attention to my bust again. I felt myself blush even deeper but I wasn’t going to lie, I liked the way he looked at me and I loved the fact that he thought I was pretty.

  “Dammit, I was going to ask you the same question about Jess,” Chrissy said to Tommy and pretended to be offended.

  “Sorry?” Tommy asked with a shrug as I laughed and he smiled over at me.

  “Steve?” said Chrissy.

  “What?” asked Steve, giggling to himself about something.

  “Truth or dare?”

  “Dare,” Steve stated proudly.

  “Lick your elbow while saying the alphabet.”

  “What?” he asked, clearly unimpressed with Chrissy’s dare. “Couldn’t you have come up with something better than that?” he argued, shaking his head. “Like you dare me to take off Jess’ bra or something?”

  “Ha ha, Steve,” I said with a frown.

  “You heard me, Steve,” Chrissy said.

  Steve tucked his right elbow near his mouth and stuck out his long, pink tongue and placed it on his elbow. Jason momentarily stopped giving Chrissy her back rub and tried to do the same thing, but to no avail. “Holy shit, you got a long-ass tongue, dude,” he said.

  “You’ve got a beautiful tongue,” Gloria playfully remarked as she gave him a very suggestive smile.

  “Thank you,” Steve said,
or at least that’s what I thought he said as the tip of his tongue connected with his pointy elbow. “A... B... C... D...” Steve recited the alphabet, as if he had a severe speech impediment. Disabilities are nothing to laugh at, but Steve’s expression was priceless and we all were delightfully entertained.

  As Steve was pulling off his goofy routine, Gloria gave me a slight nudge with her elbow.

  “What?” I said, still staring at Steve, who was struggling to keep his tongue on his elbow.

  Gloria nodded her head toward Chrissy and Jason. Jason had his head tilted back. His hands still resting on Chrissy’s shoulders, but he was no longer rubbing them. I could see her arm moving in a rhythmic motion in the water. Chrissy was giving Jason a hand job in the hot tub. I’d never seen anything like this before and at first, I was alarmed but then, I found I couldn’t take my eyes away from them.

  “Oh my God,” I whispered to Gloria.

  “She must be doing a good job. Look at Jason’s face, he’s in fuckin’ heaven,” Gloria said.

  “Maybe we should leave,” I said but I didn’t mean it. Instead, I continued to watch Chrissy work her boyfriend while I imagined doing the same thing to Mr. Jacobs. When I caught Tommy looking at me, I immediately thought of also doing the same thing to him. And then I felt doubly guilty.

  “Why?” Gloria asked.

  “What do you mean, why?” I emphatically stated in Gloria’s ear as my heart rate started to increase into overdrive.

  “What’s wrong?” Tommy asked.

  “Oh, nothing,” I said, although inside, I felt like everything around me was out of my control and there was nothing I could do to stop it. But, at the same time, I was having so much trouble pulling my attention away from Chrissy’s hand as it jerked Jason’s huge mushroom tip. His cock head was so swollen, it almost appeared purple and I could feel my pussy starting to sting as I imagined it was Mr. Jacobs’ cock I was looking at.

  Chrissy kept jerking off Jason, as she turned to face Gloria. It was clear she was on a discreet mission to make Jason cum in the hot tub, as her stroking remained consistent and focused. Tommy and Steve looked at her almost jealously, knowing full well what was going on. Tommy stretched his neck, most likely trying to remain from getting too excited and turned on by Chrissy’s actions.

  With wonderful multitasking ability, she asked Gloria, “Truth or dare?”

  “Dare,” Gloria said.

  I figured Gloria was beginning to feel a little heated because she went straight to a dare. I wanted to flee at that moment, but at the same time, admittedly, there was a part of me that wanted to see what was going to happen next. Like watching a train wreck, but with a funny feeling roiling deep in my core. I’d never seen a man cum before and I couldn’t hide my curiosity and I also couldn’t lie to myself. I wanted to watch Jason cum, there were no two ways about it. And my pussy was throbbing with the need to watch him ejaculate.

  I began to squirm uncomfortably while sitting in the tub. I downed the rest of the margarita someone had set down next to me, hoping to expedite a general feeling of numbness to help me cope with the excitement that was happening in front of me.

  “I dare you to lick Steve’s nipple,” requested Chrissy.

  “Hell no!” Gloria yelled. Judging by her over-the-top reaction and her little secretive smile, though, I knew she was pretending to resist.

  “What? If I had an out of body experience, the first thing I would do is suck on my own nipple,” said Steve.

  “Fine, but just one lick,” Gloria announced.

  Gloria leaned over and arched her back in a seductive way, purposely sticking her toned ass up in the air. She slowly unraveled her tongue from inside her full, plump and moist lips. She began lustfully circling Steve’s nipple with her tongue. His nipple was clearly erect, as it was prominently more distended than the other. Gloria then opened her lips, as salivation, caused by a deep-seated arousal, cascaded down her tongue.

  “Oh... my... God,” Steve exclaimed.

  “Woooo.... attagirl!” shouted Chrissy.

  Gloria continued making oral love to Steve’s nipples while giving Tommy a look so seductive, it would melt Morrissey himself during the peak of his asexual days. Tommy gave Gloria a light-hearted salute and a smile but then he glanced over at me, as if to make sure I was okay. But his gaze lingered on me and then dropped down to my breasts. In response, I felt my nipples start to harden as the breath caught in my throat.

  The situation in the hot tub was at critical mass. I knew what was going on was wrong and was challenging everything I held so dear, but my body felt so relaxed. The nerves inside my womb were exploding like firecrackers, but only because I was imagining doing everything I was witnessing in front of me with Tommy’s dad, with Grey Jacobs. And the very thought was causing a flux of activity that felt a lot like stinging inside my pussy.

  “Tommy, I dare you,” Chrissy said.

  “Dare me to do what?” he asked, with an impish grin.

  “Are you hard?” she asked him.

  Gloria and I intently looked on, waiting for the desired answer from Tommy. I arched my lower back a little bit more as soon as I realized one of the jets of the Jacuzzi was lined up with my clit. The rush of water stimulated every inch of my folds and moist crevice.

  “Yeah, well, kinda...” Tommy answered, immediately glancing over at me as if to say I could be the one to make him fully erect. The thought thrilled me and I suddenly wanted nothing more than to be the one who could make his cock hard.

  “I dare you to show us your cock,” Chrissy implored.

  “This shit is getting crazy,” Steve said with his eyes closed because Gloria was still going to town on his chest. Jason was practically unconscious and paralyzed in the far corner of the tub, as Chrissy continued with her precise, meticulous handiwork.

  Tommy stood up as the water level reached halfway up his muscular thighs. His cock was halfway erect beneath his briefs, the shape of his head protruding through the resistant cotton fabric. It looked massive even behind the constraints of his underwear. He put both of his thumbs behind the elastic band of his briefs, and quickly yanked them down into the water, revealing his perfectly trimmed, engorged cock. It had to have been eight inches long! His balls hung below his huge shaft and I found my eyes riveted on it.

  “Holy shit,” Gloria said in awe as she shook her head. “It’s so fucking thick, too,” she added.

  “Now that’s a dick!” Chrissy said.

  “Oh, my God,” I said, closing my eyes and reciting a quick Hail Mary in my head. Tommy immediately glanced over at me as I stared at his impressive dick. I couldn’t help but imagine what it would feel like entering me and I also wondered if it would even fit.

  “Have you ever seen a cock before, Jesse?” Chrissy asked me. I couldn’t pull my attention away from Tommy’s when I answered her.

  “No,” I said, my voice coming out breathy.

  “Do you like Tommy’s dick?” she asked.

  I felt myself flush but I also wasn’t going to lie because Tommy was watching me, waiting for me to tell him what I thought of his huge cock. And I wasn’t going to disappoint him. “Yes,” I breathed. “I… I think it’s… amazing.”

  “Thanks, Jess,” Tommy said with a little and proud laugh, playing it off, knowing full well his stallion status among the group. “Will you show me your breasts, Jess?” he asked, his voice soft.

  I swallowed hard as I thought about it. I wanted to show him my breasts, especially after he’d revealed his beautiful cock. I glanced at it again, noticing how delectably thick it was. The underside of his shaft was handsomely grooved and built for strong, hefty thrusts. His head was perfectly shaped and plump. My mouth watered at its aroused appearance. I couldn’t help but wonder if his dad’s cock looked the same. As soon as the thought crossed my mind, though, I clenched my eyes shut tight and rebuked myself for my unwholesome thoughts.

  “Jess?” Tommy asked. “Should I not have asked you that? I’m sorry.�
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  “No,” I said as I stood up, not wanting him to feel bad. I looked right at him as I reached around and unclasped the back of my bra. Then I pulled it down my arms, freeing each of my heavy tits. I pulled it completely off and watched Tommy’s eyes go wide as they took in my heavy double Ds.

  “Holy fuck,” he said.

  “Amazing fucking tits,” Steve said as Jason opened his eyes and fastened them on my breasts. My nipples were hard as rocks.

  “Oh my God,” he whispered, never taking his eyes off them.

  “Jess?” Chrissy asked.

  “Yeah,” I said, with a slight tremble in my voice as I realized everyone was staring at me and my tits and when I glanced down, every one of them had a hard cock. I hadn’t realized Steve had pulled his out but he was now stroking it and Tommy was doing the same, both of them staring at my tits.

  “I dare you to touch Tommy’s cock,” Chrissy said.

  “You didn’t ask me truth or dare,” I argued as I felt my heart start to pound against my ribs. Even though I argued, I wanted to touch Tommy’s dick. I wanted to so badly.

  “Just do it,” Chrissy demanded.

  I didn’t say anything right away. I just sat there with the jet on my clit which was making me feel things I shouldn’t have been feeling. As I sat there, I couldn’t help but focus on Tommy’s beautiful cock as I remembered Mr. Jacobs telling me I needed to get experience with boys my own age and then, once I did, I could decide if I still wanted him. So maybe this was what he was talking about? Maybe now was my opportunity to do the things Grey wanted me to do?

  “Okay, but don’t judge me and don’t tell anyone,” I said hesitantly.

  “Okay,” Gloria and Chrissy said, both assuring me at the same time.

  I slowly moved close to Tommy as he sat down on the lip of the Jacuzzi. I put my hand on his lap as I looked straight into his beautiful brown eyes. He nodded his head, indicating that it was okay for me to wrap my hand around his rock-hard dick. I put my hand around the middle part of his shaft. I could feel it pulsating and engorged with the rush of his blood. I slowly massaged the posterior portion of his glans with my index finger. He threw his head back in surrender. His cock was so thick, my index finger and thumb were nowhere near a connection. Even though I had never done such a thing, everything felt completely natural and, surprisingly, I was at ease.