Seriously Messed Up: A Laugh Out Loud Romantic Comedy

by Luke Young

  She ran her thumb over her lower lip as she studied the problem area with her eyes glazing over. Finally, she shook her head then said, “Just shove it back in.”

  He tried twice, but each time it fell back out.

  She grinned with her eyes still locked on it. “Do you want some help?”

  Before he said, “Sure,” she was already on her way over. She knelt in front of him and held it in her hands, admiring it as he stood there, looking straight ahead, and desperately trying not to laugh.

  Biting her tongue between her teeth, her eyes roamed his body coming to rest on his manhood. “So, uh, you guys are only going to be friends?”

  She looked up at his face and caught his nod. Smiling, she returned her gaze back down to it. “You’re sure?”

  “Oh, yeah, definitely.” He laughed.

  “What is it?”

  “It tickles a little.”

  Victoria held his penis gently, sighing.

  “Your hands are so warm.”

  She swallowed hard. “Is Jillian really locked out?”

  “Yepper.”

  Exhaling deeply, she tore her eyes away from his groin and up to his face. “Will you let her in and come right back here?”

  “I guess I could.” He rocked back and forth slightly with his eyes closed.

  Carefully sliding him back into the shorts, she directed it across his hip. She smiled; it looked like he was trying to smuggle a good-sized sausage. Victoria began adjusting him in the tight shorts, and it was starting to grow. Cocking her head, she took in the sight of him as she put a hand to her face. Suddenly his penis twitched and flopped out again. This time it was quite a bit bigger; most certainly from all her attention. Instead of trying to tuck it away again, she massaged it with both hands as he exhaled deeply.

  “You do have one gorgeous cock.” Closely admiring it, she licked her lips.

  “Thanks,” Brian said casually, as if he’d heard it a thousand times before.

  She narrowed her eyes. “I don’t think I can get it back in, because it keeps getting bigger.”

  “Well that’s because you keep playing with it. Maybe if you stopped pulling on it,” Brian mockingly scolded her as he patted her on the head like a dog while fighting back a laugh.

  She looked him in the eye. “Are you high?”

  After pausing, he grinned at her. “Maybe.”

  In an attempt to pull himself together, he exhaled sharply then slapped his hands on his cheeks. “I’m fine, but I really need to get back to Jillian. So, maybe you can actually help me get everything back inside, so I can go.”

  “Okay,” Victoria let go of him, stood, and tapped his chin, narrowing her eyes. Staring down at the problem area, she cocked her head. “Why don’t you put the shorts on backwards? I think they have more coverage in the back.”

  Brian slipped the shorts off and turned them around, and they did fit a little better in the front, but the back was another story. He looked down, a little more satisfied, glanced at Victoria, and she nodded her approval. Then he spun around for her to check out the back and asked how he looked. Craning his neck back, he tried to see his ass, but could not. In the back, the shorts were disappearing into his crack, and the bottoms of each cheek were sticking out. Brian looked a little like a woman heading out to the beach in St. Tropez. Smirking, she told him he looked fine. She reached out to give him the keys, but as he tried to take them, she would not let them go.

  She continued to hold them tight. “You promised you would come back.”

  “I know.”

  “Just tell her you need to return the clothes and the keys.”

  Brian swallowed hard; there was something so incredibly sexy and yet frightening about Victoria—like if she had sex with him, he’d never walk again.

  After releasing the keys, she took one last look at him in those shorts. “Hurry back.”

  “Okay.”

  He turned to the door, and she eyed his ass. “Brian, have you ever been around the world?”

  Turning back to her slowly, he looked at her, baffled. “Uh, no.”

  She gave him a sexy smile. “When you come back, I’ll take you.”

  He returned another confused look and then ran the hell out of there.

  29

  Brian’s high was wearing off just enough for him to realize he looked completely ridiculous in that outfit. He ran back to Jillian’s in pretty much the same hiding mode in which he ran to Victoria’s. Shocked, she watched as he rushed to the car, opened the door, and quickly slid in next to her. After breaking into laughter, she looked him over once more. “I can’t believe that this is what she gave you to wear!”

  “Is this not a good look for me?” Brian asked sarcastically.

  “It’s nice, but it’s probably a little dangerous to be running around Miami in the middle of the night in that outfit.”

  After summoning their nerve, the pair rushed to the front door. Jillian opened it, and they quietly slipped inside. Brian shifted left and his hip bumped against a pile of mail and a magazine sitting atop the half-wall that separated the foyer from the living room. The items scattered loudly across the floor. The two shared a wide-eyed look.

  Suddenly they heard Rob’s voice from the second floor call out, “Mom? Brian?”

  They both stood there with parted lips and one brow raised—Jillian naked and Brian dressed like a seventies roller derby queen. They were seconds from being discovered and no explanation could get them out of this. Flashes of ridiculous excuses floated through Brian’s head. Um, yeah, Rob, I was in the house and I’m a cross-dresser. And your mother… she is a nudist and she just happened to get locked outside the house and I let her in…

  Brian’s eyes brightened. “Rob, I’m coming up. Stay right there.”

  “No, I’m coming down.”

  “Shit,” Brian grit his teeth, frowning.

  Hearing Rob’s footsteps near the top of the stairs, Brian’s eyes darted around in a panic. Wearing the guilt on their faces, both were trapped in the foyer with no way to escape. His eyes met Jillian’s then he spotted the coat closet. Springing into action, he ripped open the door and shoved his naked friend-with-partial-benefits inside before shutting her in.

  Looking up in the dim light, Brian saw Rob take the first step down. He bolted toward the back of the house calling out, “I’m heading to the weight room.”

  Once in the weight room, Brian sat down on the butterfly machine and began doing repetitions.

  Rob entered and gave him a strange look that turned into a really strange look when he took in Brian’s girly, super-tight outfit. “Dude, what the fuck are you wearing?”

  “Oh this, uh, your mother lent this to me. All my stuff is dirty.”

  “Geez, if you need to borrow some clothes, just let me know.”

  Brian stood, and Rob’s gaze went immediately to his friend’s crotch. Rob covered his eyes cringing. “Seriously, let me get you something, because in that outfit, I can tell exactly what everything looks like and believe me that is information I really didn’t want to have.”

  Brian looked down, spotting the clear outline of his three-piece set in Victoria’s shorts. He placed his hands over his groin as beads of sweat dripped down his forehead.

  Rob narrowed his eyes. “My mother gave you those?”

  Brian nodded quickly. “Yes.”

  Rob raked his hand through his hair, shaking his head. “She didn’t actually see you wearing that did she?”

  “No, she’s not feeling well. She just handed them out to me through her door. I really haven’t seen her much at all since I came back from the bar… you know.”

  Rob studied his face then asked, “Are you stoned?”

  “What?”

  “Dude, are you stoned?”

  “Um, no. Don’t be ridiculous. Where would I…” Brian stammered. “No.”

  “You sure? You’re acting really strange.” Rob shook his head, confused. “Why the hell are you working out at midn
ight?”

  “Well, I couldn’t sleep. I’m wired.”

  Sighing, Rob turned away. “Me too. Laura and I had a fight.”

  “That sucks.”

  Reaching up, Rob grabbed the pull-up bar and hung from it, stretching his neck out from side to side. “You know, we haven’t really seen each other this whole trip. I still feel like I kind of abandoned you here all by yourself.”

  “No, I’ve been fine, really.”

  “Let’s do something tomorrow, all day. There’s this topless beach we could hit. Sometimes there are supermodels there.”

  “Sounds awesome.”

  “But seriously, let me lend you some clothes, because this outfit is scaring the shit out of me. I’m not sure if I’m more horrified that you’re wearing that or the fact that my mother might have at some point.” Rob performed five repetitions then dropped down to the floor. “Okay?”

  “Sounds good.” Brian nodded and breathed a sigh of relief. “I think I’m going to bed.”

  “Me too.”

  Brian turned away exposing his back side to his friend.

  “Holy fuck.” Rob gasped.

  “What?” Brian turned back.

  “Your ass cheeks, dude! They’re like completely out.”

  Glancing at his reflection in the mirror, Brian cringed. “Wow, those are tight.”

  “You think!” Rob shook his head. “I don’t have words.”

  “Sorry.” Brian shrugged, taking a step back away from his friend.

  Rob’s gaze returned to Brian’s groin and he rolled his eyes. “I’m not sure which view is scaring me more the front or the back.”

  Brian covered his junk with his hands.

  “Let’s never speak of this.”

  “You got it.”

  “I’m just going to walk in front of you.” Tilting his head upward, Rob made a face as he headed for the door.

  Craning his neck and glancing back once more at his reflection in the mirror, Brian took in the sight of his cheeks spilling out of his girly shorts. He shrugged, fought back a smile then headed out of the room.

  Brian lay in his beds with his high wearing off just enough to realize that maybe the whole friends-with-partial-benefits thing was a bad idea. He thought it was inappropriate, at best, and completely dangerous, at worst.

  He couldn’t stop thinking about how close they had been to actually having sex together. Jillian was gorgeous and sexy and everything, but he would never be able to forgive himself if he slept with Rob’s mother. They were best friends, and he felt Rob would never do anything like that to him. Rob would never consider banging his mom. Granted, his mother looked nowhere near as spectacular as Jillian, but it still wasn’t right. Brian was glad that both he and Jillian had decided to apply the brakes to their relationship, but that didn’t stop him from replaying his night with her in his head until he fell asleep. He rolled his eyes and laughed thinking of his outfit and his run in with Rob. He ran his hands through his hair while the image of Jillian’s body burned in his brain. He’d never be able to get it out. He wondered if she was thinking about him as well.

  30

  Just after eight, Jillian got up, went downstairs, and made a cup of tea. Brian came down minutes later. They shared an awkward look and then exchanged good mornings but didn’t say anything else. After pouring him a cup, Jillian led the way to the pool. She wore a long, thick robe but still looked damn sexy; he wore a GSU college T-shirt and shorts. They both slumped into the loungers with their minds obviously racing about the previous night. Staring straight ahead at the pool, neither of them said a word.

  They shared intermittent, uneasy smiles in each other’s directions as their eyes met. Huddling in her comfortable robe, Jillian had her legs pulled up as she held the scalding tea an inch from her chin. She cradled it in both hands, almost shivering as if it was freezing outside, when it was really a mild 72 degrees.

  He glanced at her. “Good tea.”

  “It’s going to be beautiful day today. Low humidity,” she said.

  “Huh, really…” After sharing an uncomfortable smile, he asked, “So, where did you get that, uh, pot?”

  “Victoria.”

  He lifted his eyebrows not at all surprised.

  She widened her eyes. “Strong.”

  “Really, really, really super-strong.”

  “You’re not yourself… at all… when you’re smoking it.”

  Shaking his head, he took a sip of tea. “Even though you think you’re thinking perfectly clearly, you probably aren’t.”

  “Exactly, and the weird thing is you remember every word.”

  “Every word,” Brian repeated as he nodded along with her. They looked at one another and shared a long, uncomfortable glance. After pausing, he placed his cup on the table between them and then swung his legs toward her. “Let me try to recap yesterday to see if we’re both on the same page.”

  Jillian turned toward him, and her robe opened a little too much to where he got a glimpse of yet another pair of her sexy, spectacular underwear. He waved his finger at the problem area as he looked away shyly.

  After correcting the problem, she closed her eyes embarrassed. “Sorry.”

  He looked back at her. “First the movie.”

  “Really inappropriate. I was actually only reaching for the popcorn.”

  “But it wasn’t there,” he said slowly.

  She shrugged her shoulders. “Could happen to anyone.”

  “Oh, agreed. Second, I came back here, and you were smoking the, uh… and I shared the… uh… with you, and then we came up with the—”

  “F.W.P.B.,” she chimed in.

  “Yes, that is the abbreviation we came up with for it. And there were several rules that went along with it.”

  “I remember all the rules.” Fighting back a grin, she stared out at the pool.

  He frowned. “Rules are important in life, but these rules, although they seemed really inspired and brilliant last night, now just seem…”

  She glanced at him. “Stupid? Ridiculous? Almost embarrassing, perhaps?”

  “All of that.” He nodded then exhaled deeply. “So where does that leave us, exactly?”

  “Humiliated, ashamed, and wanting to crawl in a hole and die, with memories in our brains we’d love to forget.”

  As Jillian listed the items, he nodded along with each. “Why don’t we just forget everything about yesterday?”

  “Like it never happened.”

  “Problem solved.” He picked up his tea. They both swung their legs onto the lounge chairs and returned to looking at the pool.

  “We probably shouldn’t ever play tennis again.” Jillian stared at him with her eyes widened.

  “Definitely not,” he agreed.

  “Although, we really are pretty well-matched out there.”

  “We are McEnroe and Borg… If McEnroe were a young, crazy, horny idiot and if Borg were a woman… a slightly older, wiser, amazing…” She smiled as he continued the seemingly endless list of compliments. “…unfairly sexy and gorgeous woman. Because let’s face it, Borg was definitely the better looking of the two tennis champions.”

  She nodded in agreement just as Rob walked out onto the patio and looked at the two of them. “Beautiful day. Perfect tennis weather. You guys should play.”

  After glancing at each other in shock, Jillian and Brian turned their attention to Rob. Rob didn’t wait for a reply; instead, he walked away as they stared at him, speechless. As he headed into the house, Rob reached back and inappropriately relieved what must have been a serious itch in a part of his ass, which was a clear violation of F.W.P.B. Rule Number One.

  31

  Rob and Brian went to the beach and saw about two dozen topless women that day. No supermodel was there, as far as they could tell. They saw women of all shapes and sizes. Rob mentioned he preferred the curvier variety and Brian agreed that there was something to be said for curves, but could appreciate the less-curvy as well. They did agr
ee that women of any size and shape, with enough confidence in their appearance to go to a topless beach, were certainly enjoyable to look at. They thanked the heavens above for supplying the fairer sex.

  Despite the pleasant distractions, Brian spent most the day wishing he were back with Jillian, playing tennis or sitting by the pool or even having that awkward conversation and tea with her. Although Brian felt that he connected with her better than he had with any woman he had ever met, he felt like it was probably for the best that they ended things when they did. They both seemed to walk away with good memories before either of them did anything to hurt the other… or Rob. Even though they never had any real physical closeness, Brian considered it one of his most successful relationships to date as sad and pathetic as that sounded to him.

  After enjoying the beach, Rob and Brian went out to dinner and then home to shower. Running late, they saw Jillian for only a moment and told her they were going to a party thrown by Laura’s younger sister at her parents’ house.

  When Rob and Brian arrived at around 10:30, Laura was already there and on her second drink. She hugged Rob when he arrived, indicating that the trouble between them was either forgotten or dulled by the alcohol in her system. Rob began drinking, while Brian decided, again, to be the designated driver. Laura introduced Brian to a friend of hers named Maggie. Finding her attractive and interesting, Brian thought that she was the type of girl he could see himself dating. They spoke about school, but not about tennis, and she seemed to enjoy his company.

  Just after midnight, Rob, Laura, Brian, and Maggie were chatting and drinking in the family room when Brian saw a girl who looked just like Natalie walk past the doorway and then out of sight. He looked at Rob to see if he’d noticed anything, but he didn’t. Brian blew it off until moments later, when he saw her again. It was Natalie, and she was heading their way. She didn’t appear to be looking at him at all. Completely focused on Rob, she didn’t look happy.