Hotel Room Lottery

Housekeeping: The first chapter is the beginning of every chapter of this story. Is it the same lead in for every chapter. The room numbers represent a divergence in the story. Different rooms = different characters and / or situations. There will be some time rewind after the room number in every chapter.

There are parts after #####. Those are character developments from the past, nothing sexual is expected to happen in these parts. Skip at your preference.

*****

Room 434

"Hey kiddo. You doing ok?" Madison asks her youngest sister. The younger woman looks miserable. She is wearing a matching dress to Madison. He long soft mousy brown hair is spread across the table as she is half way laying down on the table.

"Huh?" Courtney responds lazily without lifting her head from the table. "Yeah, I guess. I'm bored out of my mind." Madison sits down at the table that Courtney had been trying to nap at. "I get that we should be here for the wedding, but why am I in the fucking bridal party? It's not like something that I ever asked for." Courtney complains.

"So what have you done to fix that?"

"Well, apparently, I've hit on or flirted with every married guy that's within my age range." Courtney continues to complain. She has to adjust her dress as it is trying to slip down her chest. "I've gotten bitched out more times that I can ever remember."

Snickering, Madison asks, "First off, what does that have to do with you being in the bridal party? And Second, you're actually looking for dick? In that outfit?"

Rolling her head, Courtney looks at her eldest sister, "Duh, bitch! I need something to make this trip worthwhile. I'm losing a lot of money by being here. I should at least have some fun while I'm here." Courtney snaps. "Besides what's wrong with this dress aside from it's ugly?" Courtney glances down at herself.

"You keep having to pull it up. Didn't you get it hemmed correctly?"

Courtney glares at her eldest sister, "Some of us don't have as much titties for the fabric to hold onto. Fucking big titty bitch."

Madison laughs, "I'm a big titty bitch? Then what do you think of Mom or Heather?"

"Shut up, you B cup whore." Courtney replies angrily. She isn't really angry with her sister. Jealous of her larger breasts? Hell yes. Angry, nope. Courtney hates her own lack of cleavage.

"Uh huh." Madison grunts noncommittally. She turns to look out into the crowd milling about. She sees a few couples dancing to the pop music, just to pass the time.

Courtney slowly fully lifts her head to look at her sister. Her eyes study Madison's posture. Her ears are straining to hear any indication of Madison's thoughts. Courtney knows when her idol is plotting something. An idolization she has tried desperately to hide from Madison. She feels excitement building inside of her as Madison remains quiet after dropping such a blatant bread crumb to follow.

After she watches Madison finish her drink and then order a new one from a passing server. Courtney waits until the new drink is delivered before speaking up. She makes sure to be as vulgar as possible. "Ok, you heinous fucking bitch. You've obvious got something deliciously degenerate and fucking perverted in mind. And you're wanting to see if I'm game. What nasty fucking thing do you have planned?"

Smiling without looking at her youngest sister, Madison replies, "Of course, I've got something in mind. And what's even better? Is that it's not even originally my idea."

"You never accept anyone else's idea." Courtney hushes for a moment. "Unless it's... What's Uly's idea?"

Getting defensive, "He's not the only one that I listen to. But anyway, for something like this I would want my favorite Padowan to join me in this adventure."

"I'm not your favorite Padowan. We both know who he is." Courtney emphasizes the word 'he.' "I'm just your identified Padowan. So, what trouble are you wanting to get us into?"

Madison finally looks at Courtney and narrows her eyes at her, feeling a bit cross. "We'll talk about your status of favored Padowan later. Anyway, Uly had a great idea to alleviate the collective boredom."

Feeling frustrated as Madison tries to continue with her mind games, "Are you going to make me drag it out of you, question by question?"

Madison grins at Courtney. "You've learned well, Padowan. So, I'll be nice... the standard rules apply." Courtney rolls her eyes. "So the basics are this. We arrange for random hookups between interested and eligible wedding attendees. But, I need to give you the caveat that we'll have family members in it."

"Family members. Uh huh. Sure. I'm the first family member that you're asking. So, are you wanting me to help recruit? Cause I'll get the raunchiest, nastiest, most perverted people that I can. I will bathe in the anarchy and chaos."

Feigning irritation, Madison asks, "Does that mean you're in?"

"I need dick. You already know I'm in. If it happens to be Uly's?" she shrugs. "I'm going to ride him like a pony. And. And enjoy it every second. So, yes, when do we start?" Courtney slowly spreads her hands across the table to emphasize her point.

Courtney and Madison then go over the details of the plan and figure out some of the recruitment. Courtney giggles like a maniac the entire time. Courtney gets more excited as Madison fills in the specifics.

"I better get some good dick, Maddy."

*****

Courtney stalks the hallways of the hotel and conference rooms for potential "victims *cough* participants." She remembers the rules and expectations that Madison outlined. She adds her own additional restrictions. Especially, 'No fuglies.' She even texts Madison and Ulysses whenever she sees them approach someone particularly hideous looking, "I'm not fucking that!" Courtney continues to move about the wedding's guests, assessing their eligibility for the perversion that she is embracing. She reads the occasional texts from Maddy and Uly rejecting the people that she is talking to. The worst of the rejections was, "I don't think we need to unleash a fucking plague by having him sticking his dick into ANYONE! Hard pass." Courtney wasn't as shocked by the message as she was by the sender, Ulysses.

Courtney only stops recruiting after receiving confirmation texts from both Madison and Ulysses. The next text instructs her to collect the room key cards from the people that she has recruited. She deftly moves through the crowd to gather the necessary agreements and "agreements" for the event. Courtney notices a couple to plain clothes cops watching her. She feels uncomfortable with their attention. Courtney makes sure to hug everyone that she's meeting. She also speaks louder than necessary when she greets them. "Hey, Joseph! How's your mom? She didn't look like she was feeling good at the practice dinner." Once she feels that they have stopped paying attention to her, she moves faster through the crowd to finish up her task.

"I'm not letting a couple of bored fucking pigs ruin my night!" she thinks to herself as she plucks key cards from her sister's 'friend's' hands. Thinking to herself, "I need dick. Badly. I don't care if it's strange or my brother's *giggle*... hmm, yum." Courtney licks her lips slowly, "Uly would be so much fun. It would be too dangerous if I ever got my hands on him."

Courtney eventually makes her way back to the specific bar that Madison and Ulysses are waiting in. Once she sees Ulysses, she bee lines towards him. She takes a special wicked pleasure when she scares him as she snakes her arms around his waist. She slides the key cards into his back pockets as previously agreed upon, but she luxuriates in teasing him. Courtney drags her stiff nipples across his stomach. In her internal monologue, she says, "This is what you get for being a tall fucker... and a sexy fucker."

After conferring with Madison and Ulysses, she then sends out texts to the people that she recruited with instructions to meet at specific rooms. She makes some small talk with others that were brought in to participate. After waiting for a few minutes, Courtney leaves the bar to meet up in Madison's room.

Courtney sees her other sister, Jasmine, already in the room. She wanders further into the room to stand next to her. She mutters snide remarks to Jasmine about the outfits that the other women are wearing.

Jasmine gives her a once over look. "You should talk, Court. What are you wearing? Are those actual clothes? Or just body paint?"

Courtney sticks her tongue out like a petulant child. "I have to flaunt what I've got. I ain't got the fucking moo milkers that you have, bitch."

"Are you still jealous?" Jasmine asks trying to figure out how the jealousy has continued this long throughout the years.

"Until the day I die."

"Then get some plastic surgery," Jasmine hopes is some helpful advice.

Courtney recoils in disgust. "And ruin all of the time and effort that I put into looking this good? I have chiseled abs, cut arms and legs, and the tightest pussy any man will ever fuck," Courtney snaps back proudly. Jasmine rolls her eyes. Just as she's about to continue the argument Madison shouts for everyone to shut up. Courtney shoves her fists onto her hips and cocks her hip to the side in defiance. Jasmine thinks to herself, "Someone here is bound to have a small titty fetish. I hope they get her, just to shut her up."

Courtney listens halfheartedly. Her interest is piqued when Madison mentions Ulysses. Like he's some kind of bounty hunter or bouncer. She glances at Jasmine. Jasmine asks quietly, "What is Maddy's obsession with Uly?" There isn't enough time to respond before Madison continues with the rules and expectations.

After Madison finishes with her speech, Madison switches to the lottery. Courtney and Jasmine exchange another look when Madison announces that the family members have been separated out somehow.

"What the fuck does that mean?" Jasmine asks.

"I was thinking the same thing. How can she do that without effectively rigging the whole lottery. My math skills may be weak, but even I know that something's not adding up." Courtney replies. They both notice that no one else seems to realize this.

After all of the non-related participants leave, Madison spreads out a different set of keys on the table. Courtney notices that there is one missing.

"Hey, Maddy. Isn't your key missing?" she asks her eldest sister.

"Nope, it's in my pocket. Where it belongs. That's a perk of making the fun happen," Madison retorts arrogantly. "I'm going to enjoy the night's festivities within my own room."

"Did you already pick out your partner as well?" Courtney pushes.

Madison gives her a face. "Come on. That would ruin the fun for me. I want a mystery as well."

While no one is paying attention, their cousin Kylie is the first to pull a card. She practically dashes off giggling. No one pays her any mind. Courtney and Jasmine then pick theirs simultaneously. Courtney is a little too excited, and slaps her hand down on the table. They chat for a little bit as they go back down to the bar, leaving Madison alone.

Once back in the bar, the sisters separate. Jasmine goes to talk up several guys, just in case her pick doesn't work out. Courtney seeks out her only younger sibling, Ulysses.

After a couple of very quick drinks, Courtney finally finds her brother. She slams back her remaining drink, and dumps the empty glass on a random table. She does her best to sneak up on him. She thinks that he's spotted her a few times as she weaves in and out of the tables. She feels pleased with herself. She snakes her arms around his stomach, sliding her hands up underneath his shirt. "God you're sexy" she whispers into his back. She feels his body startle. He looks over his shoulder and sees a mess of mousy brown hair out of the corner of his eye. He can feels a set of small breasts pushed into him, and a pair of toned arms around his torso. Ulysses can also feel the warmth of breath from someone talking through the fabric of his shirt. It doesn't take a genius to figure this one out. Especially, when that someone is so short.

Ulysses pats the top of her hand under his shirt. Feeling the warm and loving reminder that her brother notices her, she flexes her fingertips to lightly scratch his skin.

"So, what time do we start again?" she asks loud enough for him to hear.

"You ladies will be heading up in about six minutes at nine o'clock. The guys will follow up after 15 minutes."

Courtney holds onto him until she hears Madison announce the time. She lightly scratches his belly one more time before disengaging from him. She quietly heads over to the elevator. She lets her cousin Kylie take the first one. She doesn't wait long for an empty elevator to open up.

Courtney has no trouble finding the room. She thinks that it might be her cousin's, Franklin, room. She sets her bag down in the closet area. Next she cranks up the A/C. "I want him to want me clinging onto him." Courtney kicks off her shoes, and opens up her bag. She pulls out her makeup for a quick touch up to her smoky eyes. She then swaps out the makeup bag for her "fun" bag. She turns down the bed to get ready for her partner's arrival. Courtney tucks some of the "fun" bag under a pillow.

Lastly, Courtney changes into a pair of tight form fitting shorts. Looking in the mirror, she doesn't like how it covers up her navel. She folds it down to display her belly button with with its shiny piercing. She also pulls on a form fitting cropped metal band tshirt with the back cut out in several spots. She looks in the mirror to make sure that her bat wings tattoos are visible. While it's not big, She really likes how it covers her shoulder blades. She hopes that whoever he is that he likes it. She knows that Ulysses likes it. She licks her lips thinking about her younger brother.

******

Ryan sits at the bar, slowly drinking his bourbon and coke. He watches all of the younger folks wonder around being oblivious to the world outside and how badly things can get fucked up. He sees several of his nieces and nephews carrying on without a care in the world. Ryan has been questioning his decision to get involved in the "unplanned activity." Ryan is trying to make sure that he's buzzed enough to lower his inhibitions to join in on such a morally reprehensible "activity," but not too drunk that he can't perform.

His performance anxiety finally gets the best of him. Ryan digs into his pocket for the blister-pack of three pills. After ripping one of them off, he stuffs the others back into his pocket. He pops it out and tosses in into the back of his mouth, and chases it with what remains of his drink.

Several seconds later, the bartender slides a new drink in front of Ryan. He groans, but pulls out the cash for the drink and a tip. He folds the money into a tent before dropping it onto the bar and waving for the bartender to keep the change. The bartender inconspicuously sweeps the blister pack trash off of the bar.

A quick glance at his watch tells him it's approaching 8:45 pm. His nephew, Ulysses allowed him to pick his card first, so that he could leave as quickly as possible. Ryan has yet to look at the room number written on the card that he drew. Ryan is hating on himself for choosing to be in this "activity." He continues to deal with the alcohol in front of him.

Eventually, Ryan hears, "9:15 guys. You're allowed to go back to your rooms." He can see Ulysses do a mental check list of who is moving towards the door. Ryan ducks around the back end of the island bar. He knows that he should be seen by his nephew, but still doesn't want to mentally acknowledge his participation. Ryan barely escapes without notice. Ulysses looks for him but doesn't stress over it. Ryan takes the stairs to avoid the rush for the elevators. He finally accepts that he needs to look at the key card to know where he's going. 434. The room number sounds familiar. Like it's one of the family's rooms. Ryan takes the stairs at a quick pace. Unconsciously his mind recognizes that he shouldn't be able to do that if he was in poor shape / health like he always says that he is. Ryan gets irritated with the weight of his bag. Quickly exiting at the fourth floor, he reads the signs to reorient himself. He walks with a purpose to the designated room. Ryan is desperately hoping to avoid notice from any of the wedding's attendees.

Staring at 434's door, he sighs, questioning what he is doing. He sighs again and again trying to prepare his mind for what waits behind that door. Ryan 'dusts' off his jeans and punk band tshirt that he knows his sisters disapprove of. He hears the elevator down the hall ding. He finally slides his key card into the handle. He knocks briefly before pulling the card back out to open the door.

He does all that he can to not panic. Walking into the room, he sees her bag in the recessed closet. He drops his bag next to hers. He then sees high heel shoes set neatly outside of the closet. He kicks his sneakers off and pushes them next to the heels in as orderly manner that he can. Which isn't saying much due to the alcohol in his system.

As he get ready to step into the room, he hears a very soft and feminine voice hiss, "Fuck, yeeeessss."

The lizard brain in the back of Ryan's skull wakes up. He can feel the flood of adrenaline. Something is very wrong, but very right. "I know that voice," he thinks to himself. "This was supposed to be a anonymous fling. Shit. Shit. Shit..." Looking up at the bed, He sees his favorite niece grinning like a hungry feral animal. She's sitting on the corner of the bed, leaning forward. Her hands grip the corner of the bed in between her knees. Her feet are swinging adorably while he sizes him up.

She hops off of the bed. Courtney stretches her arms over her head, pushing her chest out. Her shirt rises up more to reveal more of her flesh and highlight her abs. She starts the slow walk towards him, swinging her tiny little hips seductively.

Ryan's thinking, "How does she have such little hips and able to do that better than a runway model?" Ryan's thought processes are getting a little fuzzy as blood is diverted away from his brain. He feels as entranced as a mouse in front of a swaying cobra.

Courtney slides her hands up his sides and over his shoulders. She locks her fingers together behind his neck. "I got one of my top picks. I am very satisfied." There is heavy emphasis on the word 'very.' "How about you, dear Uncle Ryan?" Courtney purrs.

Ryan sputters for several seconds trying to respond. Eventually he stops trying to say anything. He has to finally come to a decision.

He leans down and kisses her softly on the lips. He takes pleasure in the soft warmth, as he feels the soul crushing guilt of what he's about to do. Opening his eyes after the kiss, he sees the fire in her eyes and the maniacal smile painted across her face.

"We're going to have so much fun tonight, Ryan. Or should I call you 'lover?"

#####

Ryan is sitting quietly at the poolside of his sister's and brother-in-law's house. He has been crashing there for several weeks as his house is being divvied up by the attorneys. He knocks back his third drink since waking up from his Saturday afternoon nap. He knows better than to be getting drunk with the kids around, but the divorce is messing with his head. He cannot for the life of him think about what he did wrong to lead to this.

He has spent every weekend day since comfortably numb, thanks to the famous brothers, Jack, John, and Jose. The Captain makes the occasional appearance in his glass. His drinking is becoming problematic. He doesn't know it yet, but he will be the excuse in someone else's divorce within the coming months.

He hears the glass door slide open. A 12 year old Courtney comes out carrying a metal box and an open beer. She is wearing a set of boy cut shorts with a sports bra styled bathing suit. Ryan is thankful for the fact that his nieces are getting a chance to be kids as long as possible instead of getting caught up in the hyper sexualized fashion that has been becoming more common in the recent years.