Seriously Messed Up: A Laugh Out Loud Romantic Comedy

by Luke Young

  She closed her eyes and sighed. “I’ve never felt this way before, and—”

  Just then the lights blasted on in the house, and Rob appeared at the back door. He instantly spotted his mother but didn’t see Brian. “Mom is that you?”

  She pushed Brian toward the cover of the diving board and yelled back nervously, “Yes… what are you doing back?”

  “It’s a long story,” Rob began as he headed out the door.

  “Wait, I’m, uh, not wearing anything.”

  “Jesus, Mom, you’re skinny dipping?” Turning away, Rob faced the house with his head in his hands.

  “Yes, just—”

  “But I really need to talk to you.”

  “Go inside, and I’ll be right in.”

  Rob headed into the house as Jillian moved toward Brian and whispered, “Okay, let me figure out what to tell him about the two of us, and then I’ll come get you.”

  “What the fuck is he doing here?”

  She shrugged. “I’ll find out. Just wait here.”

  “Okay, but just bring me some clothes.”

  Getting out of the pool, she dried off quickly and wrapped her towel around her body. She grabbed Brian’s towel and wrapped it around her head.

  “Hey, I need that.”

  “I’ll bring you another. Just stay in the pool.”

  She rushed into the house and left him frowning in the water.

  Ten minutes later, Jillian appeared at the second-floor balcony wearing a long robe. She held a bundle of his clothes and whispered, “Come here. Brian, come here.”

  Rushing out of the pool, he dripped his way over to the house and looked up to her. “What the hell is he doing here?”

  “There was this big incident. He broke up with Laura. There was some kind of fight… He was thrown off the ship and had to fly home. It’s a long story.”

  “Did you tell him about us?”

  “No, he’s going through a lot right now. I just can’t spring this on him.”

  He crossed his arms and shivered. “So, what the hell should I do?”

  “I hate to ask this, but can you go to Victoria’s? I’ll meet you there later.”

  “Seriously?” He stared up at her with his jaw hanging wide open.

  Slumping against the railing, she looked sadly down at him.

  He let out a long slow breath. “All right, but do you think maybe I could have my clothes?”

  She smiled at him and whispered, “This is just like the last time, remember? You look pretty cute down there naked. I’ll bet Victoria would love to see you ag—”

  From inside the house on the second floor Rob yelled out the door, “Mom?”

  “Oh shit.” She leaned over the balcony. “I’ll get there as soon as I can.” Looking back into the house, she spotted Rob standing in her room and quickly moved the bundle of clothes behind her back.

  Pointing into the house, she screamed, “Oh, my God!”

  Rob nearly jumped out of his skin. “What is it?”

  “Is that… is that a spider?”

  “Where?”

  She pointed across the room and when Rob turned to look, she blindly swung her arm back, launching the bundle over the balcony. Rushing back into the house, she closed the door behind her.

  Arching high in the air, the clothes and towel bundle separated as they fell down. Brian’s shorts, towel, underwear, and one shoe got caught up high in a tree near the house. His other shoe smacked him in the head and knocked him to the ground just as his shirt landed next to him.

  Staring up at the stars while lying flat on his back, he groaned. “Fuck.”

  He stood and looked up into the tree. It was pretty dark out, and he couldn’t see much except for the one shoe that was stuck on a branch. He whispered toward the second floor, “Jillian… Jillian.”

  After waiting ten seconds, he sighed in defeat. He picked up the shoe and threw it into the tree to try to knock the other out, but it never came back down. He exhaled deeply, tiptoed to the back door, and hid out of sight. Turning, he peered through the doorway and spotted Rob facing away from him. Brian slumped against the glass, inadvertently striking it. As Rob craned his neck to look out the window, Brian quickly moved back, got down on his hands and knees, and crawled away.

  Spotting the shirt on the patio, Brian crawled to it. He grabbed it, rushed to the edge of the yard, quickly looked back, and saw Rob and Jillian sitting on the sofa. Rob appeared to be crying like a baby. He sighed, used his hands to get as much water off his body as he could, and then slipped the shirt over his head. The shirt barely covered his dangling penis, and when he pulled it down in front, it popped up in the back, exposing his ass.

  Rushing around the dark backyard, he looked for anything else he could use to cover up. During his search, he smashed his foot into something on the ground and launched into a minute-long, profanity-laced, nearly silent tirade as he rubbed his throbbing foot. After one last curse and eye roll, he looked at the house, only to see Jillian still comforting her son. Exhaling deeply, he headed to the gate.

  6

  Brian was able to reach Victoria’s house uneventfully. As he stood at her front door holding his shirt down to cover his private area, he looked skyward. “I can’t believe this is fucking happening again.”

  After pausing a moment, he took a deep breath before knocking softly. He waited thirty seconds, and then knocked a little louder. A few seconds later, he heard a car approach and braced himself as the headlights shone right on his naked ass. He quickly looked over his shoulder and pulled his shirt down in the back to cover his rear. This exposed everything in the front just as the door opened and a four-and-a-half-foot-tall seventy-year-old woman appeared nearly eye level with his hanging manhood. The woman didn’t say a word as Brian glanced back at her and put his hands over his groin.

  “Sorry,” he muttered.

  The woman screamed and slammed the door.

  “Shit.” He shook his hands in a panic, trying to decide what to do. He knelt near the side of the door behind a potted plant as the headlights continued to shine on him.

  A 6-foot-5-inch burly senior citizen ripped open the door; Brian could see Victoria right behind him.

  “Really? Where?” Victoria asked excitedly.

  The man glared down at the half-nude Brian. “I’m calling the police.”

  Victoria’s face lit up. “Brian, what are you doing here?”

  The old man asked, “Vicky, do you know this man?”

  “Yes, Dad. This is Brian. Jillian’s Brian. I told you about him.”

  Victoria’s father looked at his face at first with a smile, but then he shook that off and just looked confused as Brian stood up, holding his shirt down over his junk and looking at them both apologetically.

  “Are you high again?” Victoria asked.

  “No, it’s a long story. Could I just come in?”

  Brian stood in the foyer in front of Victoria’s grumpy-looking father and her now-smiling mother. Victoria’s mother was looking at his legs and just a little higher, and Victoria was grinning as she watched her. He continued to hold his shirt down in front with both hands. Moving her head at an angle to get a clear view of his ass, the old woman’s smile widened. Brian gave her an uncomfortable look.

  “Brian, this is my father, Jake.”

  Brian lifted one hand up to shake Jake’s while using the other to continue to hold down the shirt. Jake began to extend his hand, but then thought better of it, since Brian’s hand had recently been just over his… well, you know. After giving him a sorrowful, uneasy look, Brian moved his hand back to his shirt.

  “What are you doing here?” Victoria repeated. There was a loud knock at the door, and Brian turned quickly, exposing his backside to the three Wildes. Jake gasped, his wife’s eyes now widened to equal her smile, and Victoria tilted her head to get a better look. Brian reached back to pull down his shirt over his ass and nervously turned back to them, inadvertently exposing his front. Grumbling
, Jake looked away as the two women each raised an eyebrow with a sexy smile.

  Brian covered up quickly and stammered, “Uh, nice to meet you both, but I’m just going to go and hang myself now.” He widened his eyes in embarrassment and scanned the area for an escape route; spotting a room, he rushed toward it and closed the door.

  Ten minutes later, Victoria knocked on her bedroom door, didn’t hear a reply, and went inside. She found the door to the bathroom closed and knocked on it.

  “You can come in,” said Brian.

  Victoria found him sitting on the edge of the tub with a bath towel wrapped around his waist, still wearing the shirt. He didn’t look happy.

  “Jillian called.”

  “Really?” He gave her a disinterested look.

  “She wanted to make sure you got here okay.”

  “I didn’t get here okay.”

  “Well, I told her that you did.”

  “Who was at the door?”

  “My neighbor. He said he saw a half-naked man sneaking around my house.”

  He rolled his eyes. “And your parents? Are they, uh…?”

  “They left.”

  “Sorry.”

  She motioned with her hand not to worry. “They were about to leave, anyway.”

  “Is your mom okay?”

  “Oh, I think she’s more than okay. She was rushing my dad to get home. She probably started blowing him before he got the car out of the—”

  “Okay,” he interrupted, giving her a sour look. “I don’t want to think about your mom performing oral sex on your father while he… Seniors have enough trouble driving. They shouldn’t be getting blowjobs while they do.”

  “Good point.” After pondering that thought for a moment, she fought to wipe the image from her mind. “Jillian told me that Rob came home early.”

  “Yeah, and at the worst possible time. She was just about to tell me if she wanted to marry me or not. It seems like every time we’re naked in the pool, someone barges in on us.”

  She gave him a judgmental stare. “Maybe you should stop doing that.”

  Putting his hands on his hips, he shot her a look. “Or maybe people should not return home three days early from a cruise without calling and still other people should not use their emergency spare key for non-emergencies.” After taking in her insulted look, he sighed. “Sorry. I’m not mad at you.”

  He glanced down at the floor, exhaled deeply, and then looked up at her sadly. “I love her with all my heart. If I can’t spend the rest of my life with her, I don’t know what I’ll do.”

  She looked as if she could cry at any moment. “Wow, you are something. Are there any more like you back home?”

  “I do have a younger brother.”

  “How old?”

  “Twenty.”

  Victoria gave him a perky smile. “Really?”

  He returned a concerned look. “You stay away from my brother.”

  She scoffed. “Okay, I was just kidding around.”

  “Sure you were.” They both knew she wasn’t kidding at all.

  Delivering him an encouraging look, she smiled sweetly. “I’m sure she’ll say yes. She told me she loves you.”

  He returned a devastated expression. “Has she talked to you about me? Has she told you what she’s going to say?”

  “I, uh… Of course, we’ve talked about it. We’re best friends. She didn’t tell me her answer, but as I said, she loves you. I told her to go for it.”

  Glancing at her face, he exhaled deeply. “I appreciate that.” As Brian stood up, the towel began to fall from his waist. He grabbed it quickly. “Do you think you could give me something to wear?”

  “Sure.”

  He glared at her. “Something that might actually provide some coverage this time.”

  She smiled brightly. “I’ll get you some men’s clothes.”

  “You have men’s clothes!”

  “Sure, I have a whole closet full of them. I’ve had them for years.”

  “You bitch.” He stared at her angrily until the goofy expression on her face brought out his smile.

  She paused to reminisce. “That was a fun night.”

  “It’s one I’ll never forget.”

  They looked at each other, reliving it for a moment, before she rubbed her hands together. “So…” She moved toward the door. “Why don’t you relax and take a shower? I’ll lay out your clothes on the bed, and then I’ll fix us a drink.”

  “Okay.”

  Turning back, she smiled. “Just don’t do that thing Jillian told me you like to do in the shower.”

  “Jesus, she told you about that?”

  “I told you that she tells me everything.” She flashed her eyes at him mischievously. “I was just kidding—if you need to jerk off, be my guest.”

  He chuckled. “I think I’ll just take a normal shower.” He turned toward the shower as she began to shut the door. Turning back, his smile was quickly replaced with a look of concern. “Hey, I’m not going to come out to find you waiting for me wearing some kind of leather harness and sitting in your sex swing, am I?”

  She poked her head back into the room. “My sex swing has been broken for over a year now.”

  He held back a laugh. “I’m serious. No funny stuff.”

  Stepping back into the room, her expression dripped with compassion. “Look, Jillian is my best friend, and I would never do anything to ruin that. As desperately horny and attracted to you as I am…” She consumed him with her eyes as a semi-scary expression spread across her face. “and as much as I would like to see if I could fit both your balls in my mouth while I—” Her eyes traveled back up his body, stopping briefly at his midsection before picking up the horrified look on his face. “Whoa, sorry. I had some wine with dinner and, uh, I’m not sure where I was going with that… I would never do that to her.”

  He reflexively covered his groin with his hands. “Um, okay then.”

  Smiling, she slipped from the room and closed the door.

  7

  Brian wore a pair of actual men’s shorts and a shirt as he sat on the sofa with Victoria. They each held a gin and tonic. It was their third, and they were both just south of tipsy.

  “I fucking love her.”

  “I know, but how’s the sex?”

  Shaking his head, he looked at her with his eyes wide. “Amazing. The best I’ve ever had.”

  She looked at him, wanting more. “I haven’t had good sex in months. Could you give me some details?”

  He shrugged his shoulders. “I’m not sure I want to share the, uh—”

  She frowned. “Let me get you another drink.”

  One and a half drinks later, he was slumped back on the sofa, staring up at her with a silly grin. “Her pussy tastes so good that I could lick her for hours.” Narrowing his eyes, he sat upright on the edge of the sofa. “Sometimes she is so wet and it just…” He fell back, shaking his head and imagining he was with her doing that now while running his tongue around his mouth.

  Captivated, she smiled. “Have you guys done anal again?”

  This ripped him from the midst of the fantasy, and he looked at her, astonished. “You mean, since we did it here less than twenty-four hours ago?”

  She nodded hopefully.

  “I know it’s hard to believe, but no, we haven’t done anal again.”

  Frowning now, she took a sip of her drink.

  He slipped a piece of ice into his mouth and held it there. “Can we talk about something else—maybe your sex life?”

  “What’s left of it, anyway.” She sighed. “What do you want to know?”

  “Like, what was your craziest-ever sexual experience?”

  She thought a moment. “One time I had these two guys over here, and I wanted to see if I could fit both their cocks inside me at the same time.” He stared wide eyed at her as she continued, “One guy was kind of thick, and the other guy was—”

  He interrupted her with a hand gesture that indicated
that was too much information.

  After frowning, she started again, “So then I fit both their…” she paused, rolling her eyes and making quote marks with her hands, “generic-sized penises in my mouth pretty good, but…”

  “How in the hell do you even—”

  She got up, put her drink down, and then stood in front of him. “I arranged the sofa so there were two of these sectional pieces in the center of the room.” He watched her, mesmerized, as she demonstrated. “Then I had them lay back, balls-to-balls, with their penises nearly touching.” He stared at her curiously but also taken aback.

  “The oral went pretty well, but when I tried to get them inside my pussy, I, uh…” She spread her legs to simulate how she hovered above them, trying to slip them both inside. She bounced up and down slowly as she looked at him. “I went like this, and I could barely get more than two or three inches inside.”

  “Huh.” He looked away, a little horrified now.

  Moving back to the sofa, she curled her legs up under her as she appeared to still be in the midst of the spectacular memory. Brian checked the time on his cell phone and sighed. “I think I’m going to go to bed. I’m exhausted. I guess she’s not coming.”

  “I’m sure she just got caught up talking to Rob. He can be sort of a drama queen, you know.”

  After nodding in agreement, he stood. “Sorry about messing up your night.”

  “You didn’t. I was a little bored until you showed up.”

  About thirty minutes later, Jillian snuck into the guest room and gently woke Brian. Opening his eyes, he gave her a groggy smile.

  “Sorry I couldn’t get here sooner. I heard you made it okay, so I didn’t call again. I’m really sorry.”

  He sat up a little and glared at her. “You know, I had to come over here bare-ass naked—again.”

  “Why? I threw down your clothes.”

  “If you look at that tree in your backyard, you’ll find most of my clothes in it. I had a shirt, and that was it.”

  “I’m so sorry.” She fought to hold back a giggle. “At least you had your shirt this time.”

  He sneered at her. “Oh and does Victoria have any brothers or sisters?”

  “No, why do you ask?”