Big Bad Cowboy: A Billionaire and a Virgin Romance

by Tia Siren

  Something seemed very familiar about the voice on the other line, but she couldn’t put her finger on it.

  Time passed, and the clock eventually read 2 pm. It was raining again outside, and Kara sat and watched out the window again with a book in hand.

  She felt a tap on her shoulder and swiveled to see Henry standing there.

  “Why are you here,” she asked.

  “Albert said he couldn’t make it, and I should take his spot,” he replied while plopping down in the overstuffed chair nearby.

  “How do you know Albert,” Kara wondered.

  “Well, funny story, that,” Henry said, “I made him up.”

  Kara wasn’t laughing.

  “Henry, why are you torturing me like this,” she asked.

  “I really don’t know,” he replied.

  There was sincerity in his reply that Kara hadn’t heard before. Henry appeared genuine for the first time since Kara had met him.

  “Okay, Henry, you’ve had your fun, I need to get back to real work now.”

  Henry didn’t budge from his seat.

  “Kara, why do we constantly fight?” he asked.

  Kara knew what she wanted to say, but wondered if she was just parroting what she had said in the past. The only reason she could honestly come up with is that she didn’t want to feel like she was just another face. She wanted to be more than just another passing fancy.

  “We fight because you’re super annoying,” she said.

  Henry smirked.

  “I guess you’ll never let down your guard,” Henry said while standing up to leave.

  Kara stood as well.

  “Is this some kind of joke,” she asked, “you make someone up so that you can come see me after you said that you wouldn’t bother me anymore. Now you’re walking away with your tail between your legs.”

  Henry paused and lingered for a moment before answer, trying to think of a reply. Nothing really came to him, so he just said what was on his mind.

  “Kara, I don’t like many people, but I like you,” he said.

  Kara let out a brash laugh that left Henry feeling a little silly.

  “Henry, I don’t think you know what it means to like someone.”

  “Kara, I mean it when I ask you out, I really do want to try to take you out for a date and see if we could be something more than acquaintances.”

  She was feeling incredibly frustrated. This was a new tactic, for sure, and Kara couldn’t figure it out.

  “Okay Henry, let’s try it,” she said, surprising herself.

  She hadn’t meant to accept, but the words escaped her mouth before she’d really thought about them.

  Henry’s eyes lit up, his usual serious gaze disappeared.

  “I don’t suppose you’d want to go out right now, would you?”

  Kara shook her head.

  “No, I’m busy today,” she couldn’t backpedal this time. “Just call me, maybe we can get together later or tomorrow. I’m usually free on Sunday’s.”

  “It’s a date,” he said, bouncing out from the library.

  The rain let up, and small jets of sunlight streamed in through the glass. Kara already missed the rain, but the rainbow was a welcome change.

  “Great,” she said to herself with an exhausted sigh.

  5.

  Sunday began with a phone call.

  “Hello,” Kara said, answering the call with her eyes full of sleep

  “I think I have an idea of what we can do today, dress warm and meet me downstairs,” Henry replied then ended the call.

  Kara wanted to stay in bed for another hour or two. She rarely had the chance to sleep in, and this was the first day in more than a few months that she’d had the time.

  Still, she found herself interested in seeing what he meant by ‘dress warm.'

  Kara raided her closet and put on the warmest things she could find. Sadly they didn’t look that great together. Kara was a curvier girl, and it was always hard to find things that fit just right. Her large bosom barely fit into regular bras from the store, and her curvier hips made buying jeans a nightmare.

  She usually ended up in comfy leggings and a knee length dress. Today, she put on a pair of ill-fitting jeans and a sweater than made her look just a little bit wider than usual. Kara hated it but went with it anyway.

  Downstairs, in the walkway leading up to her apartment, stood Henry. A small bundle of wildflowers perched in his hand and his hair was combed just a little bit to one side. Kara suppressed a giggle at his new hairdo.

  “Alright, what’s the plan then,” she said.

  “Today is a special day,” Henry replied.

  “Oh yeah, and what’s that mean,” questioned Kara.

  “It means that you’re in for quite a treat.”

  Then he thrust the small band of flowers towards her.

  “These are for you,” he said.

  She took the mangy flowers from him.

  “Thanks,” she said unenthusiastically.

  Henry offered an arm, and Kara reluctantly took it.

  Although, now that she was there, she liked it. She knew that she’d get a lot of looks from any other girl that walked along the sidewalk.

  Kara’s curiosity was going a bit wild. She wondered what it was that he’d planned for the day. He made no mention nor did he have anything that gave away his plan. Henry just continued to walk with purpose down the lane.

  A small band of people was gathered up ahead. Kara recognized the area but didn’t understand why people were gathering in the space.

  “What are we doing here,” Kara asked.

  “You’ll see in about five more minutes,” Henry replied after checking his phone.

  Kara started trying to guess, but she hadn’t a clue. More people started gathering until there must have been more than fifty people that had congregated. It must be something important, but there wasn’t anything around except for people.

  Then a single person came running through the middle of the crowd with a spray paint can. They continued to fire a steady stream in a line along the ground through the middle of the crowd.

  Once the line was finished, Kara started to realize what was happening. Each side of the line faced the other and dodgeballs started appearing out of nowhere.

  “Don’t tell me this is a-”

  “Dodgeball Flash mob!” shouted Henry.

  The two sides clashed with ferocity. Small rubber balls flew this way, and that, and Kara did her best to avoid them. Henry went on the attack, catching a few balls that would have hit Kara and throwing them back in the chaos.

  At first, Kara felt incredibly out of place, but after five minutes she couldn’t stop laughing. She couldn’t remember the last time she’d had as much fun in a crowd. Even when they were tagged by the balls they calmly walked out of the crowd and waited for another chance to get back in. For almost half an hour the crowd played before they started dispersing.

  Out of breath and ready to leave, Kara and Henry parted ways with the action and made for the shops nearby. Kara led Henry to her favorite coffee shop just down the road and ordered them both a hot chocolate to warm back up. Together, they sat in the overstuffed chairs by the fireplace in the middle of the room.

  “Okay, I’ll admit,” Kara started, “I had fun. Thank you for the invite.”

  Henry nodded with a mustache of whipped cream covering his smile.

  “I thought you might enjoy it. The best things in life are free,” he replied.

  “I couldn’t agree more,” Kara added.

  “So tell me, has your opinion of me improved a bit,” Henry asked.

  “Perhaps a small bit,” she replied.

  “Progress is progress,” he quipped, “I was thinking I could cook you lunch at my place.”

  “How about you make me lunch at my apartment so that I can change out of these ridiculous clothes,” Kara said.

  “So eager to invite me in, I see where this is going,” he said with a laugh.
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  “We could just call it a day right now if you keep up that attitude,” she replied.

  “Okay, okay. Old habits die hard. I think your place is probably cleaner anyway,” he said.

  Together they finished their drinks and sauntered off, back down the road. They continued to talk as though meeting for the first time. A certain level of maturity was exuding from Henry that Kara hadn’t seen before.

  They stopped at a grocery store and gathered a few things they might like for lunch, and Henry promised that she wouldn’t have to lift a finger.

  Once they returned to the tiny apartment, Henry wasted no time getting acquainted with the kitchen. He showed a lot of talent at cooking that Kara didn’t know he had.

  “I cook a lot, actually,” he said, “I just grew up as the head chef of the family since my mom was always working.”

  “And your dad?”

  “He wasn’t in the picture at all. Guess he just figured he had better places to be.”

  Kara felt a little sorry for him, and she made it apparent with her face.

  “It’s nothing to be sorry about,” he said, “I actually never minded taking care of my younger siblings. We’re a close family and always will be.”

  He smiled, but this time, it was honest and heartfelt.

  The food he made was quite good, the two of them sat on her bed in the small studio apartment as there wasn’t much other seating.

  “Do you know why I always shoved you away?” Kara asked.

  Henry shook his head no.

  “You have this air about you, like everything in life is easy. I’ve never had friends like you do, nor have I had such an easy time getting into college. I might have a scholarship too, but I had to spend hours studying to get it. You just had to play a sport.”

  “I spent hours practicing,” he replied, “probably spent more hours on skates than you did with your nose in a book.”

  She really didn’t know what else to say. But, then he leaned in and stole a kiss.

  Kara couldn’t believe it when it happened, but didn’t pull away. When Henry stopped, she felt sad that it was over so soon.

  Kara moved back in for another kiss, and Henry was happy to oblige her. She gracefully put her hands around him, and he hugged her and pulled her in closer.

  A rush of emotion and excitement came to her. She knew she wanted this and Henry surged with passion, laying her down on the bed gingerly.

  Kara stripped off her top, revealing her large buxom chest, exciting her mate even more. He followed suit and tore off his raggedy white shirt.

  She calmed herself momentarily as he unhooked her bra. Kara felt a little embarrassed, not knowing what he would think about her, now that he’d seen her like this.

  Henry looked ravenous, rubbing and pinching her nipples with his hand. Kara caressed down along his tight abs, running her hand along each ridge. Then she found her hand resting on his jeans, wanting to free his manhood.

  She dexterously undid his jeans and tugged them down, along with his underwear. He stopped for a moment to stand up and finish taking off his garments, and while he did, Kara saw the perfect chance to remove what little she had left.

  Henry stood at the end of the bed, surveying his prize. Kara let go of her inhibitions and opened her legs just a little further so he could get a better view.

  Like a wild animal, he collapsed on the bed. She felt warmth in the pit of her stomach and felt her chest get more flush as she lie there with him kissing every inch of her.

  Henry kissed further and further down her stomach until his mouth met her wet sex, and with a flick of his tongue she felt ignited. Tiny sparks shot through every little nerve in her body, making her fingers tingle and her head light up with excitement.

  Every circular lick with his tongue excited her more until she could take no more. She wanted him now.

  Kara grabbed his head and pulled it up to hers. He did as he was told, following along and bringing his mouth up to meet her.

  “I want you inside me,” she said.

  His throbbing member rubbed up and down her dripping womanhood, something she hadn’t felt in a long time. With a slight pop, she could feel him begin to enter. The tingly feeling in her extremities was heightened the further he pressed in.

  Henry was bigger than she thought he’d be. She wondered if she would be able to take all of him, but he fears were quickly forgotten the more he inched inside.

  He continued to suck and pinch on her nipples and only threw her to new planes of pleasure. Only once all of him had entered did he start pumping, in and out.

  Henry’s hips motioned in circles around her as he pushed his manhood inside. She grasped the blankets out of reflex, or possibly in an attempt to keep her from flying away.

  The world disappeared, and all that existed were two celestial bodies, wrapped in ecstasy. She didn’t want it to end, but could already tell it was near. Kara couldn’t last much longer.

  The welling up inside her became completely unbearable until it took over. Her body began to spasm uncontrollably, and she let out a scream of relief as the pleasure took hold.

  Henry could feel her tense around his manhood, as though she were trying to pull him inside more. He released himself inside her, pouring out everything he had.

  The two continued on, cloaked in the pleasure of release and completely spent.

  Tears started to stream down her cheeks without her realizing.

  “What is it?” Henry asked, puzzled and sweaty.

  “I haven’t opened up to someone in a long while. Not since high school. I’m happy that I got the chance with you,” Kara replied.

  “It’s still early in the day, I think we could have that chance again soon,” Henry replied with a coy grin.

  Kara rolled her eyes and fell back in the bed, exhausted.

  6.

  “You need to get your grades up, or you won’t be able to play anymore,” said the coach.

  Henry was hoping he wouldn’t hear that for some time. He tried his best to keep his grades up, but he rarely had the time to work on his homework and practice.

  “You might think about getting a tutor. They can be expensive, but I’ve seen many students raise their grades within a few weeks.”

  Henry wanted to do just that, but the thing that was holding him back was something that he had little to no control over.

  “Alright, Coach. I’ll see what I can do.”

  Despite his carefree attitude, Henry was usually under a lot of stress, and most of it had to do with what he might be eating the next day. He didn’t have a job to buy things and was only provided enough money, from his scholarship, for lodging and tuition. He still had to buy all his own books and food, and those were not cheap.

  Still, he thought to himself, maybe Kara would be willing to help out if he were to ask her nicely. She was a tutor after all, and quite a smart one.

  They had been seeing each other almost nightly for the last week. He spent more time at her place than he did at his own, by far. After practice, he would head straight there, and the two would usually end up entwined before the days end.

  Henry thought fondly of their escapades; he liked her more than she probably realized. Although, he still couldn’t figure out exactly why.

  A few hours passed, and he headed to Kara’s tiny apartment.

  He wanted to ask her straight away, but he was easily distracted. Once she answered the door, he greeted her with a kiss. She answered in kind.

  The day wore on, and they found themselves lying in the bed, sweaty and relaxed.

  “Kara,” he said.

  “Yes,” she asked.

  “So, we’ve been spending a lot of time together, and I know that it’s mostly been just us enjoying each other. But, I have a favor I’d like to ask.”

  “Just get out with it, will you?”

  Henry hesitated.

  “Okay, I need a tutor to help me get my grades up, or I won’t be able to keep playing,” he said.
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  Kara sat up, draping the sheets over herself as she did so.

  “You what?” she asked.

  “I need a tutor, and I thought you might be able to help me,” he said again.

  “Okay, I can do it, and I’ll even lower my rate,” she said.

  “That sounds fine,” he said, he wanted to tell her that he couldn’t pay, but he was afraid that she would say no. And, he really needed the help.

  “Can we start tomorrow,” he asked.

  “Sure,” she replied.

  He felt a little relieved that he’d have a tutor, but he still felt stressed about what she’d say after she found out he’d be unable to pay.

  The day passed, and the two met in the library. Kara was a good teacher, and Henry knew that. He worked his hardest to catch up and over the course of the next week, he was actually quite successful.

  “Okay, it’s been a week. Do you think I’ll be able to get paid for my time,” she asked.

  “Would it be alright if I paid you next week,” he asked.

  “Why can’t you pay right now,” she asked in turn.

  “I could pay you through other means,” he said, leaning over for a kiss.

  She pulled away.

  “Wait. Is this why you constantly pursued me for the last while? You needed to get a tutor for free?”

  Henry felt terrible that she thought like this.

  “No, that’s not it in the slightest-”

  “I can’t believe how far you’d go to keep playing your stupid sport. You slept with me so that you could save some money on a tutor. That’s incredibly low, Henry.”

  Kara closed her books, stuffing them inside her bag. A few of the other patrons of the library were starting to take notice, and Henry was getting really nervous; something he rarely felt or allowed himself to feel.

  “It’s over, Henry,” she said.

  Kara stood to leave, and Henry wanted to dart up and grab her. He wanted to do anything to keep her here and tell her the truth, but he was too embarrassed.

  He let her leave and just sat there in shock. The one person he thought he could confide in had just walked out of his life, and there was nothing he could do to stop it.

  7.

  Kara couldn’t remember the last time she’d cried this hard. Of course, it was due to her own stupidity. She finally thought that she’d met a man that she was capable of opening up to and possibly connecting with. Instead, she got stuck with a man that lied to her; and made her feel like some kind of prostitute.