Hotel Room Lottery Ch. 01


Housekeeping: This chapter is the same for every following chapter. It’s too long for me to copy / paste it into every chapter and still expect you to read it.

The room numbers represent a divergence in the story. Different rooms = different characters and / or situations. There will be some time rewind in every chapter.

There are parts after #####. Those are character developments from the past, for most chapters nothing sexual will happen in these parts. Skip at your preference.

As always, constructive criticism is appreciated. Unnecessarily negative, destructive, or toxic comments will be ignored and deleted.


Madison leans with her back against the bar. She really doesn’t care if her cornflower blue dress gets stained from any spilled alcohol. She hates the dress. It represents everything that she loathes and despises at the moment. The bullshit institution of marriage that turns women into second class citizens. The consumerism of unfettered capitalism. The enforcement of religious doctrine to maintain compliance and conformity. The need for humility someone so that they don’t overshadow the bride. That her younger sister always hits the mile markers before her. That she is soul crushingly single.

She slowly sips at her ranch water, seething at the audacity of her sister to make her her Maid of Honor. Looking down at her outfit, she mentally ticks off the things that she despises. The color, the length going just below her knee, that it unnecessarily poofs out a couple of inches from her knees, the unnecessary horizontal pleats, and the horrible artificial fabric that she can’t remember the name of but is currently causing her to sweat profusely. The only things that she likes about it are the built in bralette and lack of straps. The only creature comforts in the dress. She knows that she is tolerating this humiliation for her sister’s future happiness.

Her youngest brother walks up to her side. He sits down and signals for the bartender. He gets a little concerned with how Madison is leaning up against the bar because of all of the spilled liquor and random drinks that’re on the bar. He gives her a once over before looking at the bartender. Madison is has assumed her traditionally aggressive ‘I don’t give a fuck’ stance. This is the attitude that he has always admired from her. She stares out into the crowd not caring that bosom is practically on display. He can see her nipples poking at the fabric of her dress due to the air conditioner blowing directly on them. He wonders why she has so many problems with maintaining a boyfriend, especially with her lithe form that she meticulously maintains through a strict diet and exercise. He sees the bartender oogling her intensely. The bartender is focusing solely on her small perky breasts. Feeling his ire and possessiveness rise, he decides to order a drink from the bartender.

“I’d like a coke please.” he tells the bartender in order to interrupt his leering.

Without turning around, Madison chips in, “Put some bourbon in it. I’m not in the mood to talk to anyone that’s not drinking,” The bartender asks for ID. “He’s with the bridal party, dude,” Madison interrupts again. The bartender makes noise about one of the groomsmen being under age. Madison gestures towards the crowd. “Yup, it’s that dumbass in the bright orange jacket. I heard that he has a really good fake.” Madison easily maintains her demeanor despite the bald faced lie. She knocks the rest of her drink back, and half ass places the empty glass on the bar. “I’d like another one, please.”

The bartender reminds her that this drink will be her fifth. “Maddy,” her brother pipes in. “Take it slow. We still have two more hours of this to get through. And we’re already day drinking before noon.”

“Don’t fucking remind me, Ulysses.” Madison rolls her eyes as her head lolls backwards. Ulysses is quick to gather up her loose soft tawny brown hair to keep it from touching the bar, which is obviously wet from spilled drinks. Seeing his movement, she turns to glare at him. Once she realizes what he’s doing, she remarks, “See? This is the kind of thing that I want from a guy. But instead, lil Miss Perfect once again beats us all out. Thank you, by the way. “

Ulysses releases her hair when she lifts her head to look at him. “What are you talking about?” The bartender delivers their drinks. Ulysses hands his eldest sister her drink so that she doesn’t need to turn around. She finishes turning her head to look at him. Madison studies him. From the freshly polished black leather soled shoes to the pressed slacks, crisp French cuffed dress shirt with heirloom coin cuff links, to the freshly groomed pencil thick jaw strap beard connecting to his fully developed goatee and mustaches. She quietly wonders to herself how he doesn’t have a date for the wedding. She appreciates that he doesn’t let his weight get out of control. Even though she knows that he works in a warehouse in between classes. A physically demanding job reserved 1xbet yeni giriş for the young.

“Thank you, Uly,” she mutters as she bites down on the lime garnish in order to suck it into her mouth. She quickly and deftly maneuvers the fruit slice around in her mouth before biting down. Ulysses groans quietly. She spits the rind back out into her drink. “What I mean is that I hate weddings. It’s a constant reminder that no matter how many guys that I gel with, they always bolt for the door after a couple of months… and that I’m so fucking horny right now.”

After sipping his drink, Ulysses flatly states, “Then find a fuck buddy for the rest of the weekend. We both know that ‘certain behaviors,’ no matter how tacky or poorly made as Mom puts it, are ignored at weddings.”

“Uly, we’re not at home. We’re in San Juan. If we were back home, I would just go bar hopping to find some dick.” she growls at her brother. “Besides, I don’t fucking speak the language down here. I barely passed Spanish in high school.”

Sighing, Ulysses responds, “Then find someone in the bridal party. Isn’t that the traditional thing to do?” He takes another gulp as he turns to watch the same crowd Madison is staring at.

Madison drops her head to her shoulder to glare at her brother. “You mean the bridal party that is half family / half whores?”

“It can’t be that bad, Maddy.” Ulysses gets defensive. He shifts his body enough that his deodorant’s scent is spread about.

Trying to ignore the warm attractive smell, Madison grunts in a negative manner. “Let’s see Zach has herpes, so does Ashley and Melissa. Kiesha has had multiple STDs over the years. Harold has…”

“Ok, Maddy. That’s enough. I don’t need to know any motr, nor how you know these things.” Ulysses interrupts. “It was just an idea.” Madison feels bad about how she just snapped at her youngest brother.

In an apologetic tone, Madison says, “No, it was a fair idea. You didn’t know that I know all of their statuses. But you are right about one thing.”

Cocking an eyebrow and looking at her askew with skepticism, “And what would that be?”

“I want to do something childish and foolish. Hopelessly immature. Something that I’ll be taking a gamble on being embarrassed and regret my decision.”

They occupy the bar together in silence, lost in thought. Several people actively avoid ordering drinks from the middle of the bar where the are stationed. After several minutes, Ulysses suddenly spit sprays his mouth of liquor.

“Choking on the liquor, little bro?”

“Yes. No. Kinda, I had an idea, but it’s not a good one. Interesting for all the wrong reasons. But definitely not a good idea.”

Madison blinks at him several times before responding. “And what is this idea?”

Shaking his head, “No, Maddy. It’s really bad.”

“Bad how? Embarrassing? Kinky? Illegal?”

Ulysses screws his mouth into a knot thinking about how to get out of the conversation without stating his idea out loud. “You do remember that I have my ways of getting information out of you. Right Uly?” Madison reminds him.

“Fuuuuuuck. Ok. Ok. Ok. Fine.” Ulysses relents. He sighs slowly and profoundly before continuing. “When you said immature, I started to rack my brain for immature things.” Madison nodded her head for him to continue. “I thought about the stupid frat party thing called ‘Ten minutes in Heaven.” Madison encouraged him to continue talking. “What if it wasn’t ten minutes? What if it was the entire night? And no one was yanking the door open to humiliate everyone involved?”

Madison finally stands up from leaning against the bar and turns her whole body to face him. She then leans on the bar with one arm while holding her elfin chin with free hand, “You have my undivided attention, lil bro.” She gives him another look over. She appreciates the simple yet healthy form of his body idly sitting on the stool next to her.

“Well, my brain was jumping all over the place. For some reason, I remembered that every room in the hotel is issued two key cards. What if the rooms were the ‘closets?” Ulysses stated looking at his sister’s flattened and unreadable expression. He hesitantly continued, “We could write the room numbers on them and do like a lottery. One group goes up to the rooms first. After they’ve been given enough time to get comfortable, the second group goes up. It’ll be a complete surprise for everyone.” Madison blinks repeatedly and rapidly at Ulysses as she thinks the idea over. “I mean what happens in Vegas, stays in Vegas?” He adds sheepishly.

A wicked grin slowly grows on Madison face. Ulysses feels more uncomfortable as the grin gains strength. “Uly! That would totally work! You’re a genius.” Madison is barely able to keep control of the volume of her voice. Setting her drink down, she looks for her purse hanging on a peg under the bar. She pulls out a tiny notepad and pencil. Ulysses feels guilty for looking down her chest as she bends over. “Now the question is who do 1xbet giriş we invite to the shenanigans?” Madison asks brightly as her head pops back up.


“Maddy, let’s think about this before you send out that text. Half of the people on the list are family members. Doesn’t that bother you?” Ulysses nervously asks from across table big enough to seat eight. They had met back up at the least popular of the hotel’s three restaurants. They figured that a casual dining situation would be best to hide their shenanigans. Ulysses tries to keep his eyes above the collar, in order to avoid getting caught looking at her body, as she’s dressed in form fitting jeans and tank top.

“Listen Uly. You do remember that I said that I want to do something that was foolish that ran the risk of regretting my decision, right? This is completely up my alley. Besides, it’s not half our family. We only barely make up about a third of everyone interested. I mean the family is only a hand full out of thirty / forty people. And… Let’s say that I do end up with a family member? I rolled the dice.” Madison shrugged her shoulders. “It’s time to make the best of it.” Madison explains as she sets down her phone. “I’m trapped at a shitty destination wedding in Puerto Rico, where I don’t speak the main language. I’m lonely as fuck. And I’m even fucking hornier. I need some dick. And I need it tonight. And if I get some incestuous action tonight, it’s not like I’m going to be bragging about it.” Looking Ulysses directly in the eyes. “Let me have this bit of fun. Please? Even if it’s toxic.” She tries to puts as much emotional need into her plea as she can. “It’s not even like we’re going to be sober when we do this. Ok?” Madison continues to watch Ulysses’ eyes. “Something’s bothering you. What’s up?” Madison gives him another once over. She notices that even despite that casual dress of jeans and baggy t-shirt, he’s still squirming. She finds it endearing.

“I keep getting this feeling that I am definitely getting a family member.”

“Ok, and..?”

“I’m afraid that…”

“Excuse me, kids. Can I talk with you for a minute?” a third voice interrupts. “I have some concerns about something I overheard.”

Madison struggles to control her heavy, aggressive sigh and eye roll, turning around she replies, “Yes, Mom? What’s up?”

“I heard this, um, rumor that you and Ulysses, uh, are setting up an, hmm, activity that isn’t part of the official wedding schedule,” their mother explains. Ulysses turns around in time to see his uncle, their mother’s brother walk up behind them.

“You all might as well sit down, so that this doesn’t gather too much attention.” Madison suggests as she tries to mask the annoyance in her voice.

They both take seats at the table. Their mother starts, “So, Ryan. Tell them what you’ve heard, and then I’ll go.”

Their uncle shrugs, “Ok, Sarah. So, kids, I heard that you are arranging some sort sexual match-maker thing and that several of your cousins are involved.”

Sarah adds, “I overheard that all of your brothers and sisters are involved. Well, except for Heather.”

“And while we know that certain, eh heh, things happen at weddings. We’re not sure that the people involved are, um, appropriate.” Sarah says while looking down and away for a moment.

“We don’t want to see you kids getting into trouble or hurt.”

Madison patiently waits for them to add anything else to their statements. After several seconds of silence, she tells them, “I’m not going to dodge this. I’ll admit that I am indeed organizing an ‘activity’ to let people blow off some steam and enjoy themselves. We have not invited anyone that is currently married or in a relationship of any kind. Most of the participants are not related. And everyone that is related has been informed as to the fact that there are blood relatives involved in the ‘activity.’ They are making their own decisions as to whether or not to participate.” She picks up her phone and taps the send button. Ulysses tenses up. “What other concerns do you have?”

Ryan taps Sarah’s arm with the back of his hand, “You did see Ulysses’ reaction, right?”

Focusing on Madison, “You just sent out the invite, didn’t you?” Sarah asks disappointed.

“Yup,” Madison replies with a smug shit eating grin. “Sorry, that I’m not the Princess Perfect that’s getting married. I’m just a nasty THOT that you’re struggling with marrying off. ” Madison snarks.

“Mad. There really is no need to get like that. Your mom is just worried that you two might do something rash and harmful,” Ryan states with a frustrated voice while trying not to whine.

“So,” Madison snaps while turning to look at Ryan, “You disapprove of what I’m doing? Is this the line in the sand that you’re finally going to draw and stop talking to me? There are so many other things that I’ve done that you should’ve disapproved. Besides, how do you feel about Courtney being involved? That might mess with you favorite uncle status with 1xbet güvenilirmi her.” Madison glares at him. Turning to her mother, “You of all people should understand what I’m feeling inside. I need some action. How long has it been since you and Dad got divorced? Now, while it’s not been as long as your going without sex. The only advantage you have over me is that you’ve had someone give you an orgasm more recently than me.” Madison waited for those words to take effect before continuing. “So, needless to say, I’m really fucking horny. And I’m going to take advantage of a stupid situation. And I really don’t care what you two have to say about it.”

“Besides, it’d be even more interesting if you both were in the lottery. ‘May you live in interesting times…” Ulysses mutters into his beverage, thinking that they couldn’t hear.

Ryan picked up on it first. “I’m sorry. Did I actually hear that correctly?”

Sarah’s mouth falls open into a O. Madison slowly turns to her brother smirking. “Now that’s a interesting concept. I like what you’re thinking.”

Sarah’s jaw snaps shut and whips her head to look at her eldest child. “What?” Sarah thought that she shouted the simple word, but it came out as a croaking whisper.

Throwing her hands out with the palms up, Madison retorts, “What? Who wouldn’t love to be surprised by a cougar?” Turning to her uncle, “And dad bods are currently a thing, just like cougars.”

Shamefully rubbing his stomach, “I don’t have a dad bod. You need to be a dad for that.”

Smirking and nodding, “Uh huh. Uh huh. Ok. Ok. I’ll remind Ashley, Gwen, and Meredith about that. They might want to change that.”

Sarah feels the strong need to regain control of the conversation. “Stop. As if any of the people that we are related to would be willing to engage in these… idiocies with us. Seriously, I highly doubt that anyone in your generation thinks that I’m attractive enough to sleep with. Let’s get back to reality.”

Ulysses chokes on his drink, that he’s been trying to hide in. His mother immediately reaches out to pat his back, but stops when she remembers the conversation. She is suddenly hesitant to touch him. Eventually her maternal instinct kicks back in, and she slaps her son’s back as gently as she can. She stops patting his back when she hears him say, “I can rattle off at least five people… and two of them are relatives.” Her jaw drops open again as she looks at her son incredulously. Her hand leaps back as if it just touched a snake.

Feeling flippant, Madison throws out, “If you’re interested, I can add you to the list. And I won’t even be telling anyone… It would be an fantastic surprise.” Turning back to Ulysses, she restarts the conversation. “We need to make sure that no one else hears about this. You talk to your ‘recruits’, and I’ll talk to mine. I’ll text Courtney. We can’t have Heather hearing about this. Because if she does that means Paul’s family will have heard as well.” Ulysses nods his understanding.

Sarah starts to panic internally. “We can’t have them finding out about your ‘activity.’ That would destroy the wedding. I mean I know we’re ‘undesirable’ as a family already but we don’t need any more rumors than the ones already out there.”

“Well then, mother,” Madison remarks in the most smart ass manner. “You might want to stop talking about it. Either join or shut up about it.”


Madison is sitting at her table in the hotel’s bar. She is able to see most everyone from her seat. Ulysses is wandering around, but obviously keeping an eye on her. Their mother is sitting across from Madison. Several people come over to Madison to greet her and to lavish praise about her sister’s wedding. Madison swallows her pride every time. She understands that the praise isn’t intended for her to hear, but her mother. After a minute or two of conversation, she stands up to hug them. They all slide their hands into the back pocket of her jeans. Sarah is initially aghast at this vulgar display of inappropriate familiarity. Sarah calms down after the fifth or sixth occurrence when she realizes that that is how the participants have been giving Madison their key cards.

“Ok. Ok. Ok.” Sarah mutters as she holds her head in her hands. “You win.” she declares as Madison pulls the most recent key card out of her back pocket so that she can sit. “I’m not going to say anything.”

As she sits back down, “Good. Because I’m getting tired of getting groped in public.” Madison waves to Ulysses. He comes over and takes the collected cards from his eldest sister. He drops them into an unlabeled manila envelope and walks back out into the crowd. “Mom, one of these days, I’m going to learn your secret how you raised him so differently from the rest of us. He’s impeccably polite, caring, and just generally upstanding.”

“I didn’t do anything different with him.” Sarah responds. “However, I’m starting to wonder how I raised any of you even close to right.”

Giving her mother side eye, Madison asked, “What do you mean?”

“How could I have raised you correctly if you two are planning out depraved events like this? And then on top of that, almost all of your siblings are gleefully joining in.” Sarah’s face is riddled with sadness.

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