Seriously Messed Up: A Laugh Out Loud Romantic Comedy

by Luke Young

  He agreed, and she hugged him again. As he held her, he looked over her shoulder at the tennis court, wondering if he was making a big mistake.

  After packing his things, Brian left Rob and Jillian a short note about how he was leaving and how much he appreciated their letting him stay in the house. He also thanked Jillian for the great tennis matches.

  As Natalie and Brian were about to drive off, Jillian pulled into the driveway and parked. Brian watched as she got out of the car. She didn’t see him as she entered the house.

  Brian went to the front door and found it locked. He used the key he’d forgotten to return and went inside. Walking into the kitchen, he spotted Jillian through the window, heading to the tennis court with his note in her hand. Rushing outside, he found her sitting on the tennis court bench.

  When she saw him, she smiled. “I got your note. Thought you had already gone.”

  “I almost was… then I saw you drive up.”

  He sat down next to her. “I’m driving back to school with Natalie.”

  “I…” She sighed then shook her head before tucking a loose hair behind her ear. “I… I just wanted to make sure you didn’t have the wrong impression of me. Out of the few days I’ve known you, I was loopy on Ambien and wine, drunk, and then high. If I have two glasses of wine in a week, that’s a lot for me.”

  “No.” He gazed dreamily at her. “No, I didn’t think anything… It looked like you were having a rough week, and this whole thing that happened—or almost happened—between us probably didn’t help.”

  A smile graced her lips. “I usually don’t go running around outside naked and spying on young men while they sleep and shower.”

  “Don’t worry about it, it’s not a—” His eyes shot wide open and he gave her a curious grin. “What shower?”

  “What?” she asked in a casual tone as if she were trying to cover her tracks.

  “You just said you spied on me when I showered. When was that?”

  “Didn’t we already talk about that?”

  “No, I’m pretty sure I would have remembered. When, exactly, was this?”

  “Okay.” She closed her eyes, busted. “After the second time we played tennis.”

  Pausing, he remembered the shower in question. After closing his eyes, he asked hesitantly, “Did you, um, catch the beginning… or the end of that shower?”

  “How would I know? Uh—”

  He cringed. “Was I focused on one particular… area?”

  “Focused is a good way to put it.” She nodded with rounded eyes. “I’d say you were really focused.”

  “That would be the beginning then.” He dropped his face into his hands, mortified.

  “I was honestly going to join you.” She placed her hand on his knee. “I was so worked up on the court, but then when I saw you doing… that… I had to watch.” Staring into space, she obviously relived the memory with her lips parted. “You are really good at doing that, you know. I was moved.”

  His face remained in his hands. Unable to look at her, he said in a tired, slow voice, “I’ve had a tremendous amount of practice.”

  She pulled his hand from his knee and smiled. “It really shows.”

  Straightening up, he looked her in the eye. “So you’re telling me if I wasn’t doing… that… we would have done it?”

  “Oh, definitely,” she replied casually.

  “Okay so, I’m never doing that again.”

  “But Rob would have also walked in on us. Remember, that’s when he came home.”

  “Right, right, right.” He exhaled deeply as he shook his head. “So, I guess it was lucky that I was abusing myself like that.”

  “That’s one way to put it.” She grinned. Glancing at each other, they shared a laugh until Jillian put on a serious expression. “So she drove all that way and just showed up here, looking for you? That’s kind of sweet, isn’t it?”

  “Well…” He looked away for a moment, embarrassed by the truth. He thought about telling her the whole story, but maybe to protect Rob or maybe so she wouldn’t think he was such an idiot for following Natalie back to campus when she didn’t even come to Miami to look for him, he chose to spare her the details. “Yeah, she did. It was sweet.” He forced a smile. “I still think she may be completely nuts. I’m going to take it slow, but I think I just need to see what happens.”

  After pausing to collect her thoughts, Jillian turned to him. “Out of the thousands of women on that campus, there must be a least one who would appreciate an intelligent, attractive, thoughtful young man who can cook and who doesn’t take advantage of women when they’re… you know. You are a real gentleman. And if you don’t meet someone while at school, there’s a whole other world out there when you graduate. Don’t let her break your heart. Make sure she’s really into you before you open yourself up again. Really into you. Don’t let her string you along.”

  He met her gaze. “And don’t you go settling for some jerk, even if he does wear Magnums.”

  They shared another smile. Reaching down, he picked up a tennis ball and smelled it. “Am I crazy for liking the smell of these?”

  Taking the ball from his hand, she sniffed it, closed her eyes, and smiled. “Especially right out of a freshly-opened can.” After looking at each other as if they were sharing some sort of bizarre bond, she said, “We’re weird.”

  “Tell me about it.”

  She rolled her eyes. “What’s wrong with us?”

  “I don’t know.” Pausing, he breathed in deeply while fighting back his emotions. “But I don’t think I’ll ever play again and not think of you.”

  “We’ll always have that tiebreak.” A single tear fell from her eye.

  He gently wiped the tear from her cheek and exhaled sharply. “I’ll never forget it.”

  “Yeah.” She gazed out over the court and sighed.

  “You know…” He grinned. “I’m starting to think that last ball may have bounced twice. That would have completely changed the, uh… I would have won.”

  She narrowed her eyes. “Maybe, but I don’t think you could have played another point.”

  “I still had a lot more tennis in me,” he said with his expression dripping with manufactured confidence.

  Jillian laughed. “Right.”

  He shook his head as he glanced up at the sky, drawing in a deep breath. Returning his eyes to hers, Brian leaned over and kissed her on the cheek. She closed her eyes as his warm, moist lips touched her skin for the very first time. She desperately wanted to turn to him, to kiss him hard, but as quickly as the moment arrived, it vanished.

  Pulling back slowly from her, he stood. “Well, I guess I’d better be going.”

  She rose to her feet and struggled to maintain her composure. After he handed her the ball, they shared one last smile. Jillian watched as he walked toward the house, her emotions getting the best of her, hoping he wouldn’t look back. He didn’t.

  35

  On the drive back to Georgia, Brian decided not to ask Natalie any questions or allow her to give him any details. He thought that for them to have any chance, he would probably be better off not knowing. And since they hadn’t been dating exclusively, anyway, the worst that she did was lie to him, and even that was a stretch.

  He told her he needed time to think about everything, but he spent almost the entire ride home thinking about Jillian and not about Natalie, Rob or the two of them together. He decided that he wouldn’t jump into anything with Natalie. As physically attracted as he was to her, he vowed not to have sex with her until he was sure that she was really interested in him, that she wasn’t just playing some game, and most importantly, that she wasn’t completely out of her fucking mind.

  The more he thought about everything that had happened since he’d met Natalie, the more he was convinced that she was crazy or, at the very least, the kind of girl who enjoyed watching men suffer. He didn’t want to spend another minute wondering what she was doing, where she was, what she was t
hinking, and whether or not she was really attracted to him. Because maybe she only wanted to get him back on the hook just to have one more guy fawning over her.

  When they arrived back on campus, she invited him to stay over, but he turned her down. That weekend, he did allow her to sleep in his room, where he was the one in control. When she attempted to unbutton his jeans, he stopped her, saying that he still needed time to get over all that had happened. He decided to give her a little of the same treatment that she had doled out to him for so many weeks. When they went to sleep that night, Brian wore only boxer shorts while Natalie slept in a T-shirt and underwear. He pretended to fall asleep quickly and was amused to find that she pulled the same types of tricks that he and probably many men pulled in bed, when “sleeping over” meant literally sleeping over and not something a lot more active or fun.

  Whenever she found his hand near her crotch, she would press against it, undoubtedly in the hope that his hand would somehow spring to life, realize the prize that awaited its touch, and go to work. Granted, it’s a little easier to jut your male parts out to a wayward hand then it is the female variety, but that didn’t stop her from trying at least three times that night. He held his ground all night, giving her whatever the female version of blue balls happened to be called.

  He woke first and looked at her as she lay next to him, sleeping peacefully, but he hoped completely unsatisfied. When he lifted the sheet to look at her, he saw that her panties were pulled halfway down her ass, and her shirt had risen, exposing most of her back. He figured that her underwear was pulled so far down that it had to have been a deliberate act on her part—some kind of ploy to seduce him in the middle of the night. He was sure she was hoping that a hand might travel from her back down to her perky little ass, discover that it was uncovered, and once it did, a finger would slip into that magical crevice and be powerless to do anything except venture further.

  It was the female equivalent of the old male trick, where one’s thing just happens to sneak out of the flap of one’s boxers “by accident” in search of some fun. Brian was convinced that’s exactly what the guy had in mind when he came up with the idea to add the flap to boxer shorts. Were guys really using that flap to go the bathroom, or was it put there purely to make the “surprise slip” possible? That slip could lead to the discovery by your partner and the “It’s-already-out-so-I-might-as-well…” kind of mentality.

  Exhaling deeply, he sat up looking at the exquisite small of Natalie’s back, as it tapered invitingly into the curve of her hips. Maybe he was giving himself a set of blue ones as well. He felt that familiar surge of excitement rushing to his groin, and he slipped off to the bathroom and took care of the problem. It would have been easy for him to fall off the wagon and be seduced by Natalie, but that would have given her back the power, and he was enjoying having that all to himself.

  After the bathroom break, he went to his computer and searched for a gift for Jillian. Wanting to say thank you to her for her hospitality, he searched for tennis-related gifts and found a DVD copy of the McEnroe–Borg Wimbledon final from 1980, the match with the long tiebreak that reminded them both so much of the one they had played the last time they were on the court together. He ordered two copies, one shipped to him and one marked as a gift and shipped to her. Brian typed a personal message to be included with the gift, and it took him twenty minutes of editing before he was finally satisfied with what he wrote.

  Down in sunny Miami, Jillian was craving pancakes. She grabbed the pancake mix but then reconsidered. She put the mix back and found a recipe in a cookbook. Then she followed Brian’s advice about plugging the griddle in before starting and adding one extra egg white and more sugar, along with his tip about how to butter the griddle and make two test cakes. When she sat down to eat her three flawlessly-cooked pancakes with their perfect, golden brown air bubble marks, she sighed. After pouring on the syrup, she cut into the stack with her fork, took a bite, and smiled while thinking of him.

  After breakfast, Jillian went to her study to write. She started a story about characters based on her and Brian, except the characters actually began a physical relationship starting with the night at the movies. The story pretty much followed the events as they took place up until they arrived back home from the movie theater. In her novel, when the woman opened the door, her son was not there, and the horny couple ran up to the bedroom and spent a glorious night together.

  After writing for so long that her eyes ached from staring at the screen, she spent an hour hitting against the ball machine, and while she smashed balls over the net, she wondered what might have been if Rob hadn’t been at the house when they’d returned. Would things have played out as amazingly, as they did in her writing, or would it have been a big mistake? When Jillian had exhausted herself on the court, she took a long bath, grabbed a light meal, and retired to her room to get back to writing. She spent the remainder of the week cranking out the story and hitting balls against the machine. Writing for about eight hours a day, she slaved over every erotic word in the filthy descriptions of the many long, steamy sex sessions that her two main characters enjoyed.

  Natalie wanted to go to a movie, and Brian suggested they spike their drinks and really have some fun at the theater. She turned him down, saying it was too risky. She said they might be thrown out or get into some other trouble with campus security. They went to the movie anyway, but Natalie’s knee never rubbed Brian’s, not even once… or if it did, he didn’t notice.

  Over the next week, Brian found the pre-Natalie masturbation routine was working quite well, even as she kicked things up a notch. She took to changing in front of him while he stood in her room, pretending to read a magazine. Her panties became sexier with each passing day as his will became more steadfast. She had never before bought him anything, but that week, she bought him a teddy bear (tennis-themed of course) and a new can of balls. She bought herself a racquet and a sexy tennis outfit, and they set a date to play the following morning.

  That night, they slept at Natalie’s, and Brian decided to ask her about the mysterious event from her past, which had prevented her from being able to touch a guy down there. She refused to tell the story until he threatened to return to his dorm.

  She reluctantly explained, “I walked in on my brother while he was… touching himself. I was about sixteen, and he was a year younger.”

  He hoped there had to be more to the story so he motioned with his hand for her to elaborate. “And…?”

  “And… it was really traumatic!” She glared back at him.

  Brian treaded lightly. “And… he just kept going in front of you, even after you walked in?”

  “Oh, God no! He was facing the other way. I didn’t even see it.”

  Brian made a face. “Then it happened again, and he kept setting up situations where—?”

  “No, he avoided me for weeks.”

  After staring at her with a blank expression for a moment, he had to ask, “And that’s the whole story?”

  “Yes, that’s the whole story!” She angrily shot back.

  He gave her a sympathetic look, even though his mind was telling him that she was a freaking lunatic. “I completely understand.” He realized it wasn’t the ideal formative years’ experience, but come on. “Can you, um, touch one now?”

  “To be honest, it was only yours that I couldn’t touch. This sounds crazy, but it’s your haircut. It reminds me so much of my brother’s that it was freaking me out.”

  He paused, unable to respond until he glanced at her to find she was staring and waiting for him to say something. “Oh, that isn’t crazy at all. Hair can be a powerful… trigger. I, uh… I had that psychology class last year. We talked about that… visual triggers or something.” He calmly smiled at her, but on the inside, his brain was screaming, “Holy shit!” After enough time had passed with them simply staring at each other in silence, he gave her a comforting pat on the shoulder. “I have to go to the bathroom.”

&nbs
p; He stood in front of the mirror, making crazy eyes at his reflection; he couldn’t help but wonder if he was thinking clearly about all this. After splashing water on his face, he returned to Natalie’s room. When he arrived, he found her under the covers, and her bare shoulders were showing.

  Turning toward him, she batted her eyelashes. “I really want to have sex with you now.”

  He sat next to her on the bed, contemplating what to do, as she added, “I’m pretty sure I can touch it now.”

  “Oh, that’s good,” Brian said slowly.

  “But I have to tell you something first.”

  He thought, Okay this should be really good.

  “I’m a… technical virgin,” she announced proudly.

  “What’s that?” He made a face as if he didn’t hear her clearly.

  “A technical virgin.”

  “What does that even mean?”

  “I mean I don’t have vaginal sex. I’m saving that for when I’m married.”

  He looked at her, trying to process all this. “So, what kind of sex do you have?”

  “Obviously, all the other kinds.”

  He wrinkled his nose. “Could you be a little more specific?”

  “Mostly anal and some oral. A lot of girls are now doing this,” she said casually.

  “Wow, that’s really specific.” After attempting to process it all, he had to ask, “So, how many guys would you say you’ve done, you know, with?”

  “Four.”

  “Four,” he repeated, jumping a little out of his skin. “And Rob?” He made a hand gesture as if to ask if they had also done this act together.

  “Yes, Rob.” She widened her eyes. “Is that a problem?”

  “Rob’s not the problem,” he said quickly.

  Leaning out of bed to her drawer, she pulled out a pack of condoms and a tube of lubricant, and then handed them to him. “Have you done this before?”

  “No, not really.”