Seriously Messed Up: A Laugh Out Loud Romantic Comedy

by Luke Young

  “We can go slowly, since this is your first time. It’s fun, and there’s no chance of getting pregnant.”

  He paused a moment, trying to let it all sink in. “Slow would be nice.” Sitting there, he contemplated his next move. He glanced at the condom box, and then an idea hit him. He smiled. “Oh, these are latex condoms. I can’t wear those. If I do, my dick totally blows up big… but not in a good big way… at all.”

  She nodded with her mouth open slightly as Brian glanced at her, hoping she’d buy his excuse. “Plus I’m not feeling very well—my stomach hurts. Let’s do this some other time. I’ll bring the right condoms, and it’ll be amazing.”

  “That sounds good.” After giving him a disappointed look she slipped on her T-shirt and opened the covers to invite him in. “Will you hold me all night?”

  “I will.”

  After stripping down to his underwear, he slipped into bed with her. She snuggled up to his shoulder and smiled. “I can’t wait to finally play tennis with you tomorrow.”

  “Me either.” He reached over, turned off the light, and with the mention of the word tennis, he began thinking only about Jillian.

  In Miami, Jillian sat out by the pool, drinking a cup of hot tea and thinking of Brian. It was almost midnight, and she was reminded of their pot-induced skinny dip as she looked out over the water. It was a hot night. She stood and walked to the edge of the pool, dipping a toe in the water. It felt warm but more comfortable than the humid air. Reliving a pleasant memory, she grinned, and then removed her clothes and slowly walked down the steps into the water. She swam one lap, then climbed onto a big raft. She lay on it face up with the cool vinyl sending chills through her warm skin. The air temperature was so close to the water temperature that she really couldn’t tell which parts of her body were in the pool and which weren’t. It didn’t occur to her that she was slowly sinking into the water, having bumped the raft’s fill valve when she climbed aboard.

  Kicking her foot lazily off the side of the raft into the water, she flashed back to Brian as he held her foot and gently kissed it that special night. The Jaclyn West narrative began in her mind, except this time she and Brian were the protagonists named in her story.

  Jillian lay back on the float as Brian kissed one of her feet and then the other. Moving to the side of the raft, he began lightly kissing the top of her ankle, followed by her calf, as he ran his hands up her legs, toward her womanhood. She gasped and clutched the raft with both hands; just the feel of his lips on her skin could lift her from it, almost magically. Brian looked at her face and softly said, “I’ve been waiting for this moment since I met you.”

  Jillian brought her hand to his neck and pulled him into her as he began trailing kisses from her knee to her thigh and—

  At that moment, Jillian’s body was completely underwater as the raft lost nearly all its air. Her head remained above water for only another moment as she opened her mouth, still locked in her third person narrative fantasy. As she sank further, pool water filled her mouth. In a panic, she swallowed, leapt to the surface, coughed up water, and then gasped for breath. She looked around for Brian, but he, of course, wasn’t there to save her. Climbing from the pool, half-sad and half-smiling, she remembered the joke they shared about how swimming alone is dangerous.

  36

  The next morning, Brian awoke to the incredible feeling of Natalie sitting on him and giving him the best massage he’d ever received. She worked his shoulders, back, legs, and ass muscles to the point that he was super-relaxed and lightheaded.

  “I got you something,” she said, “Well, thirteen things actually.”

  “What?” Brian groaned as Natalie continued to work the muscles in his lower back.

  “A bagel and a box of latex-free condoms.”

  “When did you do all this?”

  “While you were asleep.” Natalie nuzzled next to his ear. “After tennis, let’s come back here and just do it. I’ve got to have you soon or…” She gently took his earlobe into her mouth, which sent a shiver down his back. “While I was out, I started to rethink this whole technical virgin thing, and I think that if I was really in love with a guy, I could break the rule, you know?”

  “That’s—”

  “We wouldn’t even need to be engaged or anything, but if we were really serious, then…”

  She moved off him, and he sat up to look at her, grinning. “This sounds like it just might be the best day of my life.”

  She giggled.

  “You know, I’ve been…” He shook his head. “No, forget it.”

  “Tell me.” She placed her hand on his arm.

  “Since the first day I met you, I’ve been picturing you doing that thing… that thing with your leg pointed to the ceiling while you were completely naked. You think maybe we could—”

  “Sure.” She tipped her chin up. “I can get into almost any position you can imagine. I dare you to come up with one that I can’t do.”

  He could imagine quite a lot, and when he saw that she had remembered he liked a sesame bagel, he smiled. After telling her he would meet her on the court, he walked back to his dorm, enjoying the bagel and wearing a smile that only a natural disaster could erase.

  He thought things could be much, much worse than having a beautiful girl who was incredibly flexible, into wild sex, and great at giving massages trying to please you with everything she had. Then he tried to justify her version of the virgin thing. It wasn’t like she had done it with, like, twelve guys, or anything. Rob certainly didn’t count since he was, well, Rob. One of the other guys didn’t count because it was certainly the Greek ex-boyfriend guy, and everyone knew that to a Greek guy, that kind of sex was about as common as a kiss. At least Brian thought he had heard somewhere that another name for anal sex was Greek. Anyway, so that left two, probably a drunken one-night stand—which could be thrown away—and just one more. So, basically, she’d had that kind of sex with just one guy, and that clearly was not a big deal at all. He spent the rest of the walk home trying to come up with impossible positions for Natalie’s flexibility challenge.

  Natalie sure looked sexy on the court; unfortunately, her game was anything but. And Brian could deal with that and be patient with her, but she had no interest in trying to learn the sport and that frustrated him. She complained about the sun in her eyes, and the strong smell of the new tennis balls, as well as how her hands now smelled because of them. She seemed like she was only going through the motions out there, and it reminded him of their dates together before Spring Break.

  Next to them, a couple of college girls were playing a match. They were both heavy hitters. Brian and Natalie took a break and sat on a bench, watching them play. The girls grunted, not terribly loudly, but loud enough for others nearby to hear. After a particularly grueling rally, Natalie watched them, horrified. “What are they doing? Why are they making those noises?”

  “They’re just really into it and trying hard to win the point.”

  “I can’t imagine ever being into anything enough to make a noise like that,” she said while peeling the paper off her water bottle.

  Without saying a word, he watched as she took a sip, made a face, and then tilted her hand closer to her nose. After taking a dainty sniff, she cringed.

  He played those words over and over in his head; I can’t imagine ever being into anything enough to make a noise like that. It reminded him of what Jillian had told him when he last saw her. She said to make sure Natalie was into him, really into him. He took a long look at Natalie, as she smelled her hands again with her face all contorted. Then he watched as she discovered a dirt mark on her palm and struggled to wipe it off. He really saw through her beauty to the self-centered little nightmare that she was.

  Standing, holding his racket, he contemplated his next move. After hearing another grunt—one that reminded him of Jillian’s—he watched as Natalie rolled her eyes in response to the outburst. He stared at her, expressionless then said, “Um, I’ve
got to go.”

  “Good,” she replied as she stood and collected her things. When she turned to follow him, all she saw was the back of his head, as he was already out the gate and running toward his dorm.

  Brian ran into the suite and then burst into Rob’s room. They hadn’t spoken much since Miami, and Rob looked happy to see him. Brian asked, “Can I borrow your car?”

  “Sure. I’ll need it later though.”

  “I definitely won’t be back until tomorrow—at the earliest—and maybe not until late Sunday.” Brian bounced up and down on his heels, struggling to contain his excitement.

  “Shit, really? I don’t know…”

  “Look, you slept with Natalie, and I didn’t kill you, or anything. I also had an open invitation to violate your girlfriend nine different ways, and I didn’t. Don’t you think you owe me this?”

  “Wait, you didn’t tell me that. All you said was that she came to her senses.” Rob looked at him suddenly concerned.

  Brian said, “Do you really need the whole story? I was trying to give you guys a chance. Just like I’m sure you never told Laura about the particular type of sex that you and Natalie enjoyed.”

  Rob swallowed hard. “What do you mean?” Brian’s raised eyebrow look apparently told Rob exactly what he meant. “Oh, that. Yeah, Laura doesn’t really need to know about that.”

  Wearing an evil smile, Brian held out his hand. “Maybe it’s better that you don’t know everything about her, and she doesn’t know everything about you. And for that to continue, maybe you should just hand over the keys.”

  “You swear you didn’t have sex with Laura—no sex of any kind with her?”

  “I swear on the life of…” Brian struggled to come up with a name, a good name, and then he smiled. “Johnny Mac. I swear on the life of the greatest tennis player of all time. You know I wouldn’t fuck around with McEnroe.”

  Rob tossed him the keys.

  “Thanks, man.” As Brian rushed from the room, he yelled back, “If I’m going to be any later than Sunday, I’ll call.”

  Jillian walked out to the pool area, wearing a swimsuit and carrying envelopes, along with a package. Victoria was lying on a lounge chair in a bikini. After sitting down next to her, Jillian placed the letters on the table. She studied the package. “I didn’t order anything.”

  Jillian opened the box. When she pulled out the copy of the tennis DVD, she smiled. Discovering the note, she read it as tears formed in her eyes:

  Jillian, I just wanted to thank you for letting me stay with you in your incredible home. You mentioned you had an old, grainy copy of this great match, and I thought of you when I stumbled across it. I hope when you watch that fourth-set tiebreak (the best tiebreak ever) you’ll think of ours (the second best tiebreak ever). I bought a copy for myself, and I know I will. There are many things about the trip that I’ll never forget… I wish you the very best.

  Brian

  Victoria looked over and noticed Jillian’s face. “What’s wrong?”

  Jillian took a deep breath. “It’s from Brian.” She turned the DVD so that Victoria could see it. Victoria looked at it, a little confused, and then Jillian handed over the note. Victoria read the note as Jillian sat back, thinking.

  When she reached the end, Victoria smiled brightly. “You need to go see him right now.”

  “He’s with Natalie.”

  “How do you know?”

  “Rob mentioned it.”

  “Then why is he sending you gifts?” Victoria asked.

  “He’s just trying to thank me for—”

  “Watching him jerk off and showing him your pus—”

  “No! For staying here,” Jillian interrupted.

  Victoria read the note again. “He totally wants to have sex with you. It says it right here.”

  “Where?”

  Victoria read from the note, “‘There are many things about the trip that I’ll never forget’ dot dot dot.”

  Jillian looked at her confused.

  Victoria widened her eyes sexily, as she repeated, “DOT DOT DOT.”

  “Yeah?”

  “There are many things I’ll never forget, AND I want to lick your pussy for, like, an hour. That’s what dot dot dot means.”

  “Okay, yeah.” Jillian rolled her eyes and put her hand out to get the note back.

  Frowning, Victoria handed it over. “Why don’t you go visit Rob and just see what’s going on up there?”

  Jillian simply returned a blank stare.

  Victoria gave her a tired look. “Well, at least call him to thank him for the gift.”

  “I will.”

  Victoria rolled her eyes, and Jillian repeated, “I promise, I will. Tomorrow.”

  “You should have slept with him when you had the chance, and then when you had that other chance… oh, and then when you had that second-to-last chance and then when—”

  “All right.” Jillian exhaled sharply. “I get it.”

  Victoria put on a deadly serious expression. “I’ve been reading that semen is really good for vaginal health.”

  Jillian glanced back, intrigued, as Victoria added, “It’s something about the pH down there and how it brings it back in balance.”

  “Hmm,” Jillian said casually.

  “Not to mention the muscles in your…” Victoria pointed to Jillian’s crotch. “…will start to deteriorate if you don’t use them often enough.”

  Jillian scoffed. “Just worry about your own muscles.”

  “Oh, I don’t need to. I can pull the cork out of a wine bottle with my—”

  “How would you even…” Cringing, Jillian put her hand up. “Wait. Don’t tell me. I don’t want to know.”

  Victoria grinned as Jillian looked away in mock disgust. When she looked back, they broke into laughter.

  “I was just kidding,” Victoria said.

  “Thank God.”

  37

  Brian made the ten-hour trip in just over nine hours. Lucky for him, he wasn’t pulled over and only needed to stop once for gas. When he reached Jillian’s house, he noticed five cars parked in the driveway. After parking across the street, he walked to the house and peered through a window. He saw a group of ten people, including Jillian and Victoria, eating dinner in the dining room. There were two women sitting on either side of Jillian, and he breathed a sigh of relief, since she appeared to be dateless.

  When he saw Jillian stand up and head to the kitchen, he took off. Running to the back of the house, he reached over to unlatch the gate, and then sprinted toward the kitchen window. He saw Jillian pull a chocolate mousse ganache cake from the refrigerator and place it on the counter. He tapped softly on the window and then a little harder until she looked over.

  Recognizing him, she smiled as she rushed to the patio door. When she opened the door, Brian pulled her outside and kissed her before she could say a thing. She returned the kiss, which lasted for a good thirty seconds.

  She looked at him shocked. “What are you doing here?”

  While struggling to catch his breath, he collected his thoughts. “I had to see you. I’ve wanted to kiss you for weeks. Since I left, I’ve been thinking about what you said about meeting the right girl, and I… don’t want to meet the right girl. I mean… I’ve already met her. I don’t want to just be friends or partial friends or whatever the hell that thing was. And it’s not just because Natalie turned out to be a total psycho. It’s been killing me to find out. I’ve… If we’re even half as good together in the bedroom as we are on the court, then the sex might just kill me, but it’s a chance I’ve got to take.”

  She just stared past him, seemingly thinking and not saying a word. Brian narrowed his eyes, glanced where she was looking, found nothing back there, and then turned back at her, concerned. “It would really help me now if you said something. I just drove nine hours, and if you want me to go, I will, but I, uh, really need to pee first.”

  “If you take one step away from this house, I’ll tackle you
.”

  Brian smiled, relieved. “Good, because there is no way I’m getting back in that car right now.”

  She stepped in closer to him. “I missed you so much.”

  “Me too.” Placing his hand on her neck, he pressed his lips to hers once again. She moaned softly into his mouth. The kiss lasted a long, long time and she wrapped her arms around him. He pulled back from her and gazed into her eyes, pressing his lips together and cringing.

  “What’s wrong?”

  “I just drove the last six hours with no breaks. I really have to pee.”

  “Sorry. Sorry.” She bounced on her heels. “I have people over, and I’m just trying to figure out how I can sneak you upstairs.” Suddenly, a broad smile spread over her face then she blurted out, “Hold on.” Then she disappeared into the house, leaving him wearing a perplexed look. Moments later, she rushed back to the door and pulled him in. “When I say it’s clear, go up the back steps to my room and wait for me there. Read a book, or something. I’m sure I can get them out of here in ten or fifteen minutes.”

  She walked into the house, checked if the line of sight to the stairs was clear, and then motioned for Brian to come in quickly. He rushed in and slipped upstairs.

  After a visit to the bathroom, Brian spotted the DVD he’d bought for Jillian on top of her player, and he found his note next to the bed. Sitting on her bed, he looked around the room. He picked up a novel from her nightstand, checked the back cover, frowned and put it down. Her computer sat on the bed next to him, and when he grabbed it to move it aside, the screen brightened to reveal her latest novel. He took a closer look, reading from where the document was opened, and it began to sound very familiar. It was an erotic and accurate account of Jillian and Brian’s movie theater adventure, except the names were changed to protect the guilty.

  Downstairs, Jillian cut ten slices of cake and served them without coffee. She told her guests the coffeemaker was broken, and when one of the men offered to look at it, Jillian told him she threw it away. She was acting nervous, and Victoria looked at her concerned. The group was loudly talking and making over the dessert as Jillian barely touched her slice. When guests asked for tea, they joked that maybe all her pots were also broken. After giving them a fake laugh, Jillian rushed to the kitchen. “I’ll be right back.”