Seriously Messed Up: A Laugh Out Loud Romantic Comedy

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Seriously Messed Up: A Laugh Out Loud Romantic Comedy Page 52

by Luke Young


  He swallowed hard. Placing her hand in his lap, she squeezed his rapidly growing bulge. “Looks like he wants to do it.”

  He nearly jumped out of his skin. “I, uh, appreciate the offer, but I can’t.” Slipping off the stool, he looked at her stunning body for a moment, having second thoughts. He shook his head, handed her a $100 chip, and headed to the cashier.

  Jim’s wallet was full of hundreds as he walked smiling through the lobby. He spotted a girl who looked about his age, sitting on a large sofa and reading a book. Sitting across from her, he looked around uneasily. She noticed him staring and glanced up at him a few times. She smiled. Jim focused on the book and saw that the title was Business Law.

  He asked, “Are you taking a summer class?”

  “Yeah, I go to Drexel. I’ll be a senior.”

  “I’m starting my senior year also. I go to Penn—that’s, like, a mile from Drexel.”

  “Really?” she asked.

  “I’ll prove it.” Jim said nervously. He stood, got out his wallet, which happened to be Brian’s, reached into his other pocket, and got out his own wallet.

  “You don’t have to prove it. I believe you.”

  Grinning nervously, he put both wallets back in his pockets and sat down next to her.

  She narrowed her eyes. “What’s with the two wallets?”

  “One’s my brother’s. That’s how I got into the casino.”

  “How’d you do?”

  “I won.”

  “If you don’t mind my asking… how much?”

  “About seventy-five hundred dollars,” he announced proudly.

  “Seriously?” She gave him a big smile. “Now, that, I want you to prove.”

  Reaching again for his wallet, he stopped. “Wait, you’re not a hooker are you? I mean, sorry… One just propositioned me in the casino.”

  “No way.” She chuckled. “I’m Caroline, by the way.”

  “Nice to meet you. I’m Jimmy.”

  She frowned. “Jimmy? I hate that name.”

  He gave her a quizzical look, and she explained, “I knew a Jimmy in fifth grade. He told me he had something cool to show me. But then he showed me his penis. It wasn’t cool. It was tiny. Now, whenever I hear the name I think…” She raised her eyebrows. “How about I call you James?”

  He said in a faux deep voice, “James is fine.”

  “James, so do you gamble a lot?”

  “This was my first time.”

  “Let me get this straight, you’re an underage, first-time gambler who just won seven grand and was propositioned by a prostitute?”

  “Yep.”

  “Was she cute?”

  He gave her a wide-eyed nod in response.

  “How much was it going to cost?”

  He grinned. “With or without the anal?”

  “With, of course. You’ve got to have the anal.” She looked at him with a straight face. “It’s the new oral, don’t you know?”

  “What the hell does that even mean?” he asked. She shrugged, grinning, and they shared a chuckle.

  Jim said casually, “And she said since I was a virgin it would only be a thousand, but that was sans anal.”

  Caroline nodded. “What? Are virgins not allowed to do anal?”

  “She figured I wouldn’t want to.”

  “Makes sense. I wonder if there was a virgin discount for that?”

  “You know, I didn’t ask.”

  They both raised a curious eyebrow and sat in silence for a moment until he asked, “Who are you here with?”

  “My sister and her boyfriend. They’re up in our room having, like, a marathon sex session or something.”

  “Wow, me too. I mean, my brother is with his girlfriend. Have you heard of Jaclyn West, the romance novelist?”

  “Sure,” she said, her curiosity piqued. “You actually know Jaclyn West?”

  “I can prove that, too.” Pulling out his cell phone, he clumsily dropped it on the floor. After he picked it up, he noticed her grinning at him. He said, “Sorry. I’m a little nervous. I don’t usually do this well with a girl.”

  “You call this doing well? You’ve already accused me of being a hooker, and we just had a five-minute conversation mostly about anal sex. I’d say—”

  “For me, this is doing well,” he interrupted.

  She smiled as he scrolled to a picture and displayed it for her. Caroline narrowed her eyes at the picture and took out her own phone, did a quick search, and landed on Jaclyn’s Web page. She brought up her picture, and it was definitely the same woman.

  “Wow.”

  He looked into her eyes. She was pretty but in an understated way. He wanted to kiss her.

  “Not that I don’t believe you, but show me the seven grand.”

  Jim looked around the room, found the lobby otherwise empty, and quickly opened his wallet to show her the wad of hundred dollar bills.

  “You’re sure you’re not a hooker?” he asked with a smile.

  She said with a straight face, “You got me. I am. I also have a virgin discount, but I charge eight hundred, and I throw in the anal at no charge.”

  He almost believed her until he saw she was fighting back a laugh. Giving her a mock-sexy look, he moved closer to her and whispered, “That’s a pretty good deal. So should we just do it here, or… do you want to come up to my room?”

  She smiled at him. “Look, you seem like a nice guy, but there is no way I’m having sex with you.”

  “Who said anything about sex? I have a suite, and we can watch TV, order room service, and do whatever.”

  Looking away for a moment, she pondered his incredible story. He had the picture of the author. It was her, although he could have Photoshopped that. He did have all that money, and he seemed like a good guy. She made up her mind. “Okay, let’s do it.”

  “Cool, I just need to get my key.”

  Jim rushed to the front desk, spoke briefly with the clerk, and upgraded to the best room they had, the Plato Suite for six hundred more per night. He had them secure it with Jillian’s card, which they already had on file.

  They took the elevator up to the top floor. Caroline was alternating between typing a text, looking at him, checking his student ID again, and then typing some more. Once they stood outside the door to the suite, she finished typing a few more keystrokes, and hit send.

  “Who are you texting?”

  “Before we go in, I just want to say, you seem like a nice guy, but I sent a text to my brother, who’s a huge Marine. I told him the room number, your name, and a complete description of you.” She paused and added, “Wait. Smile.” She pulled out her phone again, took his picture, and hit a few keys to send it off. “And now he has your picture.”

  He looked at her, confused but mostly terrified. “Oh.”

  “He’ll find you much easier with the pic. He won’t have to wait for the police to figure out what happened, drag their feet, and never make an arrest… and instead of going on Nancy Grace every night for two years, he’ll take care of the problem himself.”

  “Um…” He swallowed hard. “I better not lay a hand on you, then.”

  Gently grabbing him by the shirt, she said, “Well, I didn’t say that.”

  He opened the door, and she slipped into the room ahead of him. He looked her over from head to toe. God, she was attractive!

  Inside the suite, Caroline was mesmerized by the 1500-square-foot room. It featured a huge bed, separate living room with a giant TV, and a kitchen area. They walked together into the bathroom and shared a surprised look as they gazed at the large room with its separate shower and enormous bathtub, big enough for four people.

  Moving to the living area, they sat on the sofa for a moment in complete silence until he asked, “Are you hungry?”

  “Not really.”

  “Do you want a drink?”

  “No.”

  He turned on the TV and went to the hotel channel. An ad appeared for in-room massages. They shared a look a
nd a smile.

  Ten seconds later, Jim called down to the front desk and ordered a couples massage with a female and a male masseuse. Twenty minutes later, there was a knock at the door, and five minutes after that they were both nude with towels draped over only their asses, as they lay flat on two portable massage tables. A hunky guy rubbed Caroline down, while a gorgeous woman worked on Jim. After about twenty minutes of sheer relaxing pleasure, they looked at each other, and Jim said, “This is awesome.”

  Smiling in agreement, her body melting with her masseur’s touch, she closed her eyes. And for the next thirty minutes, they were both pampered beyond belief.

  Afterward, they both wore fluffy white hotel robes. She stretched out on the sofa as Jim walked the massage therapists to the door. When he offered to pay, they informed him the massages would be billed to the room. He handed them each a one hundred dollar tip and felt like a fucking king.

  Jim and Caroline sat on the sofa, completely relaxed. Frowning, she looked into the bathroom. “I’m kind of oily.”

  “Me, too.”

  “I definitely want to try that bathtub.”

  “Can we do it together?”

  “Will you behave yourself?”

  “I will. I think I saw bubble bath in there, so you can slip into the water first, and I won’t see anything.”

  Ten minutes later, she called him into the room. When he entered, she was already in the tub with the bubbles covering up to her neck. She looked up at him, waiting.

  Waving at her with his hand, he scoffed. “Well, you know, close ‘em.”

  “Really?”

  “Yeah, I mean, you’re covered with bubbles, and you just want me to—”

  “Okay.” She sighed, put her hands over her eyes, but kept them open. She watched closely as Jim dropped his robe, focusing mainly on one part of him, as he climbed into the tub. She thought, There’s no Jimmy here—hello, James! She felt that familiar warm tingle between her legs, and it wasn’t from the delicious bubble bath.

  He lounged back and relaxed as she lifted her legs one at a time out of the water, sexily stretching and enjoying the feel of the water on her skin. “I think I could get used to being rich.”

  “Me, too. This has been the most amazing day of my life.” He gave her a mock-arrogant look. “I just want you to know that you’re not the first woman I’ve bathed with today.”

  “You’re joking.”

  “I actually took a shower with my brother’s girlfriend.”

  “You showered with Jaclyn West?”

  He gave her a big, bright-eyed nod and she returned a skeptical look.

  “Well, she thought I was Brian.”

  “And?”

  “We look a lot a like, I guess. We didn’t actually shower. She came in, and I was facing away. I turned, she saw I wasn’t her intended shower companion, and got the hell out of there.”

  “And now you’re in the tub with me.”

  “Just like I said… Best day ever.”

  She smiled at him, and they leaned their heads back, both exhaling deeply and sinking down a little lower in the tub.

  Ten minutes later, they were back in the robes, sitting on the sofa, and making out. Putting on the brakes, she looked him in the eye. “Are you actually a virgin?”

  “I am.”

  “If you’re lying to me, I’m going to find you at Penn and kill you.”

  “Gee, your whole family is seriously violent.”

  “When we need to be. So, you’re being honest about all of—”

  “I haven’t lied about any of it…” He paused, thinking. “Okay, I did lie about one thing.”

  She moved away from him a little, and he explained, “I upgraded to the suite. I was in a regular room until I met you.”

  “You little bastard,” she said jokingly.

  She put her hand on his robe and opened it up, exposing his large, half-hard penis. With her eyes locked on it, she sighed. Taking hold of it, she rubbed it while he leaned back, absolutely dying with anticipation.

  “Oh, wow,” he said.

  “I’m kind of dating someone. It was serious, but we’re taking a break. I really don’t normally do this kind of thing. You know, we just met and…”

  “Uh-huh.” He moaned as he struggled to pay attention to her words.

  “But the $500 suite…” She gave him a sexy look.

  “Eight hundred,” he corrected her, and she returned a nod.

  “And the massage and all,” she said with her voice labored as she worked her hand up and down over his erection. She stared at it closely as it got thicker and harder in her hand. She murmured, “‘Oh, wow’ is right.”

  “That, uh… massage was incredible,” he mumbled while he exhaled deeply, just watching her touch him.

  “Not as incredible as this will be.” She slipped to the floor between his legs, and he unblinkingly watched her. After glancing up at his face, she looked directly at his throbbing erection. She slowly moved her head down until her lips were almost touching it. He blinked just once, breathed out deeply, and held his breath again as he watched her extend her tongue almost to touch it, then change her mind and plant a tiny kiss gently on the head.

  As her lips pulled back from it, his mouth dropped open, and he groaned. “Now, uh, this is the best day ever.”

  She grinned at him, opened her mouth wide, and moved forward. He watched, fascinated, as she went to work on him.

  She pulled her mouth off him and frowned. “If you shoot in my mouth, I’ll also kill you.”

  “No problem. I want to see how much comes out anyway,” he replied casually.

  She gave him a strange look, and he explained, “It’s a long story.” With a quick shake of her head, she ignored the interruption, closed her eyes, and sucked him back into her mouth.

  He swore every single nerve ending in his penis could feel every part of her lips, tongue, and mouth all over him. When he’d jerked off earlier that day, it was amazing, but this—this was something else altogether. He watched in awe as she slowly moved her head up and down on him, taking slightly more of him into her mouth with each downward movement. As he watched her, he thought, Why do people ever leave the house, and how could God have made this feel this good? Once they discover this, people would never get anything done. This can’t be how it feels for everyone, is it? Maybe it’s because it’s my first blowjob? That’s it. That must be it.

  Every movement she made felt like a tiny exploding orgasm. He felt like he could cum at any moment, but something was different from when he had taken care of himself earlier. Just sitting back and watching her do this to him—he didn’t need to do anything; it was unbelievable. How would he know when he was going to ejaculate? He didn’t want to do it in her mouth, especially since she said she would kill him.

  Wrapping her hand around the base, she moved her mouth faster. She was scratching him with her teeth a little, and he grimaced in pain a few times, but it still felt wonderful. No way would he complain.

  He watched as beads of sweat formed on her brow. Her breathing became more labored. She stopped, pulled her head away, opened the robe and slid it down her shoulders. “It’s too hot for this.”

  Nodding in agreement, his eyes focused on her perky breasts.

  She adjusted her angle higher, and covered him with her mouth. He moaned loudly. He watched with his mouth wide open, barely breathing as she moved faster and faster. It felt even better now than it had before. But would he know when he was going to—

  “Oh, fuck!” he screamed out. He would know—he would definitely know.

  As she continued, he felt an unusual heat boiling up in his loins. His penis felt like it was on fire, as she slurped, sucked, and worked over him with all her energy. She was focused, incredibly focused.

  “I think…” he began as he gently nudged her shoulder.

  Caroline, lost in the moment, didn’t stop at first; she kept going up and down, harder and faster. She looked up at him, and he was risin
g up off the couch with a look on his face like he could blast off at any moment. Then she quickly pulled her head away and used both hands to finish him.

  Moments later, as he sat there recovering, panting, and staring at the ceiling, he figured that what she had just done to him—her performance—had to have been a spectacular blowjob by any measure. Although he had nothing to compare it to now, he hoped that would change and that he wouldn’t have to wait another twenty years to make the comparison.

  Concerned, she asked, “Are you okay?”

  Lifting his head, he appeared disoriented. “What? Oh, yeah.”

  She stood, let the robe fall from her tight, young, naked body, and headed for the bedroom. He watched her open-mouthed.

  He rushed in to find her lying on the bed. Crawling between her legs, he looked closely between her thighs. He glanced up at her, unsure what the hell he was doing, and moved down into position. She moaned, and he began licking her wildly, but when he brushed his teeth against her delicate skin, she scooted away from him a bit. With fire in his eyes, he moved back to her, plunging his mouth between her legs.

  “Wait.”

  Returning to Earth, he looked up at her face. “Sorry. I, uh…”

  She gave him a gentle smile as she touched his chin. “Just lie here next to me.”

  He crawled up on the bed, and they lay side-by-side, making out. Moving back from him a bit, she smiled. “Now this, you know how to do.”

  Grinning, he kissed her again before moving down to her breasts and sucking and licking them like a pro. Her eyes rolled back as she pulled his head closer into her chest. “Oh, yes,” she groaned.

  He moved back up and kissed her. Taking his hand, she guided it between her legs and showed him how to touch her. He watched her closely as she responded to their combined fingers. He studied her face as she gasped with her eyes closed and her brow furrowed.

  She rolled onto her back, and he lay next to her with his fingers deep inside her and his palm resting on her swollen clitoris.

  “Harder,” she moaned.

  He listened; she bucked her hips up and down. Grabbing his finger, she placed it directly where she wanted to be touched. “Just rub me… there.”

  He rubbed her faster and faster; she moved her hips up and down. She moaned loudly as he pressed a little harder. Holding her breath, she lifted her hips off the bed, her muscles straining. He slipped his fingers inside, curled them up toward her belly button, and hit the right spot. She screamed out with a huge release. Gyrating her hips, she panted, and grabbed his hand to keep him from moving it. Relaxing her body fully on the mattress, she gently held his hand as they lay there, recovering.

 

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