Seriously Messed Up: A Laugh Out Loud Romantic Comedy

by Luke Young

  After a quick rest and drink at the bench, he stood and pulled off his wet shirt to change it. She walked to the baseline as he picked up a new shirt. After pausing to think, he grinned, deciding to go bare-chested. He walked back to his side of the court.

  When she saw his half-nude body, she made a face. “That’s not fair. I’ll be distracted.”

  “This,” he began by motioning with his hand up and down his chest. “This is going to distract you?”

  “It might.”

  “Take your shirt and bra off then. We’ll be even-steven, as you say.” Placing his hands on his hips, he wore a smarmy smile.

  She returned a scowl. “You know I can’t play like that. They’d get in the way.”

  “Not my problem. Just serve, and stop whining.”

  She was a little distracted by his sweaty muscular body, and he was up four–two in the tiebreak when they returned to the bench to get a drink and switch sides. As he walked back into position, she secretly stripped off her panties and tossed them into her bag. While walking to the baseline, she wore an evil grin.

  He gave her a suspicious look. “What are you smiling about? You’re three points from losing this.”

  “Nothing.” She batted her eyes at him before turning away coolly. He shook his head, obviously now even more perplexed.

  She walked back to retrieve a ball, put her legs together, bent over way too much, and flashed her naked ass to him.

  He froze, gaping at the sight of her. “Are you wearing a thong? That is not cool.”

  “I might be,” she teased.

  “Maybe I’ll just pull it out right here. How would you like that?”

  “That would be against U.S.T.A. rules, and you would automatically forfeit the match.”

  “And a thong is not against the rules?”

  “No, it’s not.” She stared back at him with her head held high.

  He was obviously distracted while she played some focused tennis, winning four straight points and going up six–four. Smiling in preparation of her next ploy, she was just one point from victory. A ball sat on his side of the net, and he began walking to retrieve it. She held up her hand. “I’ll get it. You’ll need all your energy.”

  He watched with his brow furrowed, as she walked all the way to his side and knelt down to pick up the ball. After pulling her sunglasses off, she lifted her skirt up in the front and used it to wipe off her lenses. This exposed her fabulously trimmed female parts, which were just twenty-feet from him. He had an unobstructed view of her as she wiped the glasses for nearly ten unnecessary seconds.

  Stunned, he watched as she dropped the hem of her skirt and walked slowly over to him.

  She got close and said softly, “When your shirt was wet, you took it off…” Running her index finger slowly down his sweaty chest to his belly button, she smiled. “My underwear was soaked, so I did the same.”

  He stammered with his voice cracking, “This… uh… isn’t fair.”

  She parted her lips as she moved within an inch of his face. “Good…” Leaning in, she gave him a passionate kiss while pressing her body into his. When she pulled back from him, Jillian finished her sentiment, “… luck.” She turned and headed back to her side of the court, leaving him breathing heavily and uncomfortably adjusting his shorts.

  Brian’s voice cracked again as he shot back, “You’re going down.”

  As Jillian passed the net, she yelled back, “I won’t be now, and I certainly won’t be later.”

  After processing this for a second, he gave her a pathetic look. “Really?”

  She retrieved her racket and smiled. “Just kidding.” She bounced the ball, prepared to serve, and then said confidently, “Match point.”

  “Bring it,” he said as he continued to grimace and fight with his shorts.

  She hit a solid serve to his forehand, but it was clearly playable. Grinning, he took a huge backswing to really nail it but swung badly. The ball hit off the side of the racquet frame, launched high into the air, and headed the wrong way.

  They both watched as it traveled, almost in slow motion, out of the court and into the pool. He exhaled, defeated; she made a fist with her right hand in celebration, and they both headed to the net.

  When they reached the net, she grinned. He gave her a frown and said while trying to maintain a straight face, “I’m going to check the rule book on that whole production. There’s got to be some violation there.” After shaking hands, they walked toward the bench.

  He sat down as she tossed her racquet into the bag. Pausing a moment, gazing at his shirtless, sweaty body, she wanted him now and badly. He put his head down as he struggled to catch his breath. She looked him over once more and then glanced toward the pool. A smile spread over her face as she turned and headed off the court, pulling off her shirt and bra along the way. Looking up, he watched her with surprise. She stood still as she slipped off her skirt, stepped out of it, and then bent over sexily to remove her shoes and socks. He continued staring, mesmerized. She never looked back as she made her way to the water and dove in. Bending over, he fought to remove his shoes and sweaty socks. Then he shot up from the bench, ripped down his shorts and underwear and rushed to the pool.

  When he reached the edge, Jillian was floating on a giant ring with her legs spread as she looked up at him, grinning. “I’ve always wanted to try something.”

  Smiling, he dove into the pool and swam underwater until he reached her. He came up inside the ring float, between her spread legs and took a quick breath. He extended his tongue between her legs, which left her gasping and holding onto the float for dear life. After exploring her for a few seconds, Brian came up for air. “Is this what you wanted to try?”

  “It is. How’d you—”

  “I read about it in Chapter One.”

  She frowned slightly. “No more talking.”

  He went back to work, and after about seven minutes of focused effort, she experienced a mind-blowing orgasm. After switching places, she happily returned the favor. When she was finally finished with him, she left him exhausted and panting as if he’d run a mile.

  After recovering enough to speak, he said, “Wow. That was a great graduation present.”

  She shook her head a moment and grinned. “That wasn’t it.”

  42

  Ten minutes later, Jillian and Brian were floating naked on large rafts in the pool. The gentle motion of the water, along with the exhaustion from both the tennis and the sex, had rocked them to sleep. Standing at the edge of the pool, Victoria stared down at them, grinning. She studied Brian’s body for a moment before clearing her throat. “I can’t believe you two are naked in the pool again.”

  The nude pair both awoke, startled. He lifted his head to Victoria groggily and instinctively covered his penis with his hands.

  Flipping off her raft into the pool, Jillian turned to face Victoria. “What the hell are you doing here?”

  Victoria smiled. “I came to borrow that little black dress. I have a date tonight with my neighbor.” Then she glanced back at Brian and raised an eyebrow. “Nice penis, Bri.”

  Brian turned to Jillian, and then looked sheepishly at Victoria. “Thanks… again.”

  “Don’t you knock?” Jillian asked.

  “I did, but no one answered. So I used my key. I really need that dress.”

  Jillian swam over to the edge of the pool. Brian slipped off the raft into the water and joined her. They both looked up at Victoria as she sat down in a lounge chair.

  Sighing, Jillian shook her head. “You can borrow it, but next time call first. If you had walked in here ten minutes earlier…”

  “Oh, it would have been okay, because I’ve decided to become a sex therapist.”

  Jillian gave her a skeptical look.

  “I’m going back to school. I only need fifteen credits to earn my master’s degree. The University of Miami offers a program in marriage and family therapy. I’ll be concentrating in sex therapy, of course
.”

  “Of course.” Jillian nodded. “That makes sense. You’ve been practicing unofficially for years.”

  Victoria cocked her head wearing a big smile. “It combines my two favorite things.”

  Holding back a laugh, Brian just had to ask, “What’s that?”

  “Sex and hot college guys.”

  Jillian and Brian both returned a matter-of-fact nod.

  “I registered today. I’m taking one summer class and then a full load starting in the middle of August. I could give you two some pointers if you wanted to start up again. I could judge your technique and see if there’s—”

  “No, that’s okay,” Jillian interrupted. “I think we have it.”

  “I’ll just tell you that you need to be careful in the water, because the natural lubricants in the body are water soluble, so prolonged intercourse in the pool can lead to irritation.”

  Jillian chuckled. “We’ll keep that in mind.”

  Jillian made eyes at Brian as if to say, I wish she would leave already!

  Victoria’s face lit up as she asked Brian, “So, how’d you like your surprise? When she showed me, I was blown—”

  “Victoria!” Jillian interrupted. “We haven’t gotten to it yet.”

  “Sorry, I guess you’ve been too busy fucking in the pool.”

  Widening her eyes, Jillian motioned to her with her hand. “Well, thanks for stopping by.”

  Brian placed his hand to his chin. “So, it’s something you show me. I wonder what…”

  Victoria stood up and then headed for the door. Jillian called out, “That dress is on the left side of my closet. Don’t… uh… get anything on it. If you know what I mean.”

  She turned back. “Oh, I think I’m going to take this one slow. He seems like a really good guy. Mature, hot, and just… perfect.”

  Jillian chuckled. “So does that mean you’ll wait until after dinner to have sex with him?”

  After glaring at her a moment in mock anger, Victoria smiled. “No, I mean I’m going to wait for a couple weeks, at least. I don’t want him to think I’m just some big slut, or something. If this works out, I might give monogamy a try.”

  “You should,” Jillian began. Then she looked at Brian, completely smitten. “Monogamy can be pretty amazing.”

  He took her in his arms, and they kissed, as Victoria looked on, grinning. “You two kids are so adorable.”

  Jillian turned away as she felt her emotions getting the best of her. Brian looked up at Victoria and smiled, but as the awkward moment lingered too long, he gave her a tired look.

  “Okay, okay. I’m going.” Victoria headed into the house as Jillian squeezed the bridge of her nose to fight back her tears.

  After Victoria was gone, he pushed back from the edge and floated on his back. “What are the chances that she doesn’t sleep with this guy tonight?”

  After putting on a smile, Jillian swam toward him. “I hate to say it, but if he’s as attractive as she says, I’d be surprised if she kept her clothes on much past the appetizers.”

  He nodded in agreement and slipped under the water for a moment before coming back up to find her treading water right next to him. He placed his hands on her shoulders. “So, what’s the surprise? I can’t wait.”

  Pushing him away, she swam to the other side of the pool. He watched as her back side rose out of the water right before him. He remained simply staring at it with his mouth wide open until it disappeared when she descended underwater. When she reached the edge of the pool, she climbed out, grabbed a towel, and began drying off.

  “Come on. How about one hint?”

  Turning back toward him, she gave him an evil grin. “You’re just going to have to wait.”

  43

  After a shower, Jillian prepared a quick, light meal, and then they took a walk together to let their food settle. When they returned, she announced that it was time. She had him wait in the study while she went into the workout room. Brian found it a little odd that she would go into that room for his surprise, but at the same time, he was intrigued.

  A few minutes later, she called his name, and he hurried to the room. Stepping through the doorway, he found her completely naked and in the famous Natalie-esque leg thing position. She stood on the ball of her left foot, and her right leg pointed straight up to the ceiling. Her right elbow rested against her right knee, her forearm ran along her leg, with her hand holding her ankle. In her left hand, she held a strap that came down from the ceiling for support and placed that hand over her right one.

  Moving closer and seeing her in that position, his eyes shot wide open, as did his mustache-covered mouth. Blindly feeling for the weight bench and unable to tear his eyes from her, he finally found it and plopped down. “I can’t believe you learned how to do the leg thing for me!”

  “The proper name for this position is développé leg devant à la derrière.”

  He nodded quickly. “That name sounds better.” Tilting his head, he gazed at her from a different angle. “How did you, uh—”

  “I told you, I was a gymnast in middle school, and I worked a little with a coach for the last six weeks. It took a lot of practice, but it’s been worth it. I’m so much more flexible now.”

  He straightened his head and then swallowed hard. “More flexible?” Looking away for a moment, he thought about the positions they had already explored together, he smiled dreamily.

  He turned his attention back to her. “You look incredible.” Motioning to her womanly parts, he wore a giddy smile. “I can see everything, and it’s… wow… You look… there’s not a word strong enough for how you look. I could watch you do this for hours.”

  Her body trembled slightly and her voice quivered as she said, “I can only hold it for, like, three minutes.”

  “Natalie said she could do it for thirty,” he said with a smirk.

  “Don’t forget… Natalie lies.” The grimace on her face grew with every passing second.

  “Good point.”

  He looked up at the ceiling, noticed the strap, and then smiled. “Don’t you think the strap is cheating a little?”

  “Do you want me to do this or not?” Glancing at him, she frowned. “I’d like to see you do this naked, strap or not.”

  After obviously both processing the image of a nude Brian in that position, they cringed and said in unison, “Probably not.”

  “God, you look amazing!” He got up and walked over to her. Sliding in close, he tried to size up all the sexual possibilities while she was in that position. “I wonder if we could really do it like this.”

  “I’ve been thinking about it a lot, too, but if I don’t put my leg back down, it’s going to snap off.”

  He took a step back, then gently helped her return the leg to the floor. Slumping down, she scowled in pain while rubbing the muscle in her thigh. She straightened up, took a deep breath, and smiled. “Now, what’s your surprise?”

  He held his chin as he eyed her naked body, torn. “As much as I hate to say this, I really think you should be dressed for mine.”

  “Thank God. So it’s not sex related.”

  “What, you don’t want to do it again?”

  “I do, but before we do…” She glanced hesitantly at him. “I hate the mustache. Shave it, please. You look ridiculous.”

  “You’re kidding.” After scoffing, he studied himself in the wall of mirrors. “I think I look older, maybe even thirty.”

  “You look like a seventies porn star.” Shaking her head, she slipped on her underwear.

  He sat back on the bench and watched her get dressed. “You know, watching you put on clothes is almost as much fun as watching you take them off. It was hot the way you shimmied that skirt back on.”

  When she was fully dressed, she checked herself in the mirror. After making some final adjustments to the skirt, she bounced up and down eagerly on her heels. “Now, what’s the surprise?”

  “Not here.” Standing up, he motioned for her to foll
ow as he headed out of the room.

  He led her out to the pool area, where he had candles, glasses, and a bottle of champagne on ice waiting for them by the lounge chairs.

  “When did you have a chance to set this up?” She gazed at the setup, blown away.

  “While you were making dinner.”

  Holding her hand, he guided her to a chair. He lit the candles, opened and poured the champagne, and then handed her a glass. They each took a sip and placed the glasses on the table.

  “So, what is it? Do you want to have sex right here or something?”

  “Maybe later.” He drew in a long breath and let it out slowly. “Okay, my company has a permanent position open in Miami, and once I get through the management program, they said it’s mine if I want it.”

  “Do you want it?”

  “It depends.”

  Getting down on one knee in front of her, he pulled a box from his pocket. She looked at him, holding her breath. He stared into her eyes. “I know I’m young, and I don’t really know exactly what I want to do with the rest of my life… career wise or anything.” Studying her face, he noticed he was losing her a little. “Sorry, I mean, I do know that I want to spend every minute I can with you. From the first moment I saw you right here on this chair and… then we spoke for, like, an hour on the tennis court… talking about the damn court surface,” he added, rolling his eyes. He grabbed her hand, and they shared a smile as he continued, “I knew then I was falling for you. I’m absolutely head-over-heels, can’t-stand-to-be-away-from-you in love, and I don’t care who knows it. You are more alive and fun to be with than any of those young college women I’ve ever met.”

  He opened the box and displayed the gorgeous one-carat diamond ring. Her eyes lit up as she gazed at it. He pulled it from the box. “Jillian Grayson, will you marry me?” Smiling at her with hopeful eyes, he slipped the ring on her finger.

  She gave him a hesitant look. “But I’m old enough to be your mother.”

  Slipping back to his chair, he did some quick calculations in his head. “You’re still only thirty-nine right?”