Hotel Room Lottery

Housekeeping: If you have not read the previous chapter, please go back. It provides the set up to the situations described in this chapter.

The portions after ##### are background. Typically there is nothing sexual in these sections. Skip at your preference.

*****

ROOM 432

"Hey, James. What are you up to?" Ulysses asks his brother.

James' head pops up from his drink and boredom. Looking at his younger brother suspiciously. "You only use my government name when something is is going on. What's happened?"

Ulysses tries to shrug within a suit that he has never worn before and replies, "Nothing major. I was just hanging out with Maddy. And we got to talking about how bored we are."

"Uh huh," James grunts forcefully. "What are you up to you fucking Chaos Goblin? Is Madison in on this too?" James retorts not feeling like he should let down his guard.

"Sigh. I'm not trying to pull anything. Please don't come at me like that. Nothing has gone sideways. I was actually thinking about including you into something that Madison and I are planning. If you're not interested, I'll get out of your hair. But it requires secrecy. It's nothing inherently illegal, but can be highly embarrassing if the wrong people find out." Ulysses explains. He puts emphasis on the word 'wrong.'

"So you mean Paul's family. Understood." James confirms. "This is starting off interesting. So am I required to promise my silence in order to hear about this thing you're planning?" Ulysses nods. "Fine. You have my silence. What stupidity are you two cooking up?"

"Ok. So, Madison and I were both bored out of our minds and having a very strange conversation. Basically, we developed the thought about setting up a lottery type of thing based on the idea of 'Ten minutes in heaven." Ulysses pauses to gauge his older brother's reaction. James gives no indication of an opinion. "But we thought about making it all night long and using the hotel rooms as the closets, so to speak."

Quietly, James asks, "So, you're basically arranging a socially distanced orgy?"

Nervously, Ulysses blurts out, "No, no, no, just one partner for the entire night."

James motions for Ulysses to calm down and to lower his voice. "Chill, dude. The concept sounds fun. But you haven't given me all of the details yet."

Ulysses went on to explain the selection process and a quick preview of who has already expressed interest in the activity. James notices that most of the names are family members. Ulysses hopes that his lie of having others on board already won't be detected.

"Question. That sounds like a lot of our siblings. What's up with that?"

"I, well, I thought that, that would show that we're planning this for the people that we can trust. We do have a lot of the other guests as well... but, I, um, didn't want to you be angry if you found yourself in a room with family."

James thinks about it for a moment. "Ok, I'm not yet UNinterested. Are there any MILFs in this?"

"We've got a few on our list to ask. But we're asking people that we hope would say 'yes' first with minimal convincing."

Nodding his head, James thinks over the offer. "When would I have to let you know that I want to jump into this?"

"Just text me or Maddy by 5, I guess. We're going to do the selection after the rehearsal dinner tonight. If you want to join you'll need to give us both of your key cards in the bar before we do the lottery."

Laughing, "Shit. You're moving really fast on this. How horny is Madison?"

Looking around him before answering, "I think she's about to go after anyone if she doesn't get some sort of satisfaction soon. Like multiple people before we go home."

Still laughing, "I think I'm in. But I want to ask you one thing."

"What's that?"

"Can you make sure I get a MILF? You know that's my thing."

"Let me talk to Maddy."

Smiling wildly, James replies, "Bet!" and sticks out his hand to shake on it.

*****

James follows all of the amateurish attempts by his siblings to maintain secrecy. He lost count of how many times he has rolled his eyes at the comical efforts his eldest sister and younger brother have gone through to set up the activity. After Ulysses has distributed the keys in the first envelope he sends out a text. He dumps the second envelope onto the table, spreading them out.

Ulysses nervously waits. His phone pings. He reads a simple text of "432." He quickly pulls that card out of the pile. He then offers the remaining cards to his remaining family members. He glares at James when he starts to move towards the pile. James smiles softly and backs up, allowing the others to pick.

Once everyone has left. Ulysses offers the card that he pulled out to James. "This is the only MILF in the group that's worth it. Madison wasn't happy about your request." He pockets the last card.

Raising his eyebrows, "But you convinced her otherwise?"

"Yes. And I'm in deep shit with her for it."

"I'll help you out with that if the she's worth it." James pats Ulysses on the back.

As James turns to leave the room, Ulysses remarks, "She is definitely worth it. She was the hardest person to convince to join in the... fuckery."

Looking over his shoulder as he walks out, "I'll be the judge of that. But at least I know you put in maximum effort to help a brother out,"

"Do yourself a favor. Buy some flowers," Ulysses calls out.

*****

Sarah nervously looks at her watch. She couldn't bear to be seen in the bar mingling with all of the potential...

She struggles to find a word to fit the situation. She finally settles on the word 'suitors.' She gets out of her car when it hits 9:02. She pops her trunk and grabs a carry on bag with all of her stuff that she'll need in order to avoid a 'walk of shame' in the morning.

After pushing the button to call the elevator, Sarah finally pulls out the key card to look at the number. 432. She thinks to herself, "Isn't that Ulysses' room? I'm not sure how I'd feel if I matched with him."

Sarah nervously moves about the elevator as she waits for it to get to her floor. She restrains herself from actually running out of the elevator. She exits in as controlled manner as possible. She lugs the bag down the hallway. As she is within reach of the room that she has mentally labeled as 'the den of sin,' she sees her niece Kylie waving at her as she enters Sarah's room. "What is that big freaking bag for?" Sarah mentally asks herself. "Is she moving into my room, or is she just that... depraved?"

Sarah slides her key card into the door. She's feels foolish feeling surprised when the lights on the handle turn green like this wasn't going to work. She slides into the room in the least suspicious way she can. As the door closes behind her, she takes a look around the room. She sees confirmation that the room is Ulysses'. His bags, laptop, cologne, and whatnot are spread around the room.

She sits down on the bed and does a couple of breathing exercises. She is trying to get her emotions under control. "What the fuck am I doing? I literally signed up for a blind date that is expecting sex. How fucked up have I become since Trent left?"

After a couple of minutes of calming herself down, Sarah busies herself with prepping the room. She starts by hiding Ulysses's items. Sarah then pulls out the things that she planned on using for a possible seduction. She quickly changed into a set of matching bra and panties. It's not the lingerie that she would prefer, but it's the best she has available on this trip. And under the time crunch. Draping one of the hotel's housecoats over herself she then moves around the room again. She sprays some of her perfume through the room, desperately hoping that the smell will wear off before Ulysses comes back into the room, but needing to feel more comfortable with her fucked up decision to participate in one of the most perverted things she's ever heard of.

Sarah turns the covers of the bed down, before she has the thought, "What if it's someone that I won't do this with? Never mind that. What if this is someone I can't do this with?" She nervously fidgets. She decides to busy herself with 'pretty-ing up' the room. After climbing into the bed, she continues to mess with the room's appearance. "Why is this not looking the way I want it? Will he understand why I'm decorating? Oh, fuck. Am I panicking?" She climbs back out of the bed to readjust everything.

The knock startles the shit out of her. She rushes to finish up with her preparations.

She realizes that she is bent over the bed when it dawns on her that her lottery partner is not only in the hotel room, but watching her.

*****

Ulysses shouts over the music to the group of collected men, "9:15 guys. You're allowed to go back to your rooms."

James waves at the bartender. Once he has their attention, he makes a slicing motion against his throat to signal that he wants to tab out. James feels lucky that he pays out fairly quickly considering that there was a rush of people to leave.

He wanders slowly to the elevators after picking up his bag from his brother's table amid all of the other bags. He knows that he needs to give his 'date' some time to get settled in. He also ponders about the level of anxiety that she might be feeling waiting for him to get there. He starts planning out potential excuses if things go sour.

Thinking to himself, "How do I even start this conversation? I'm starting to feel nervous. They did promise that no one in the group is married or in a serious relationship. I wonder what she looks like? Bah. I'll find out in a minute. At least I have the condoms in my bag." as he rides the elevator up to the designated floor.

After a short walk to room 432, James stops in front of the door. It dawns on him that he should knock before entering. He gently taps his knuckles on the door. After waiting for a moment, he hears no response. He sees his cousin Kyle coming down the hall with a small kit bag. They nod greetings to each other, but share no words. James slides the card into the slot on the door. Once he sees the green light and hears the whirling click, he twists the handle, and enters the room.

*****

The first thing that James notices is the smell of perfume. His internal monologue continues, "That's a really good scent. Definitely single mother, or maybe divorced. Most likely a soccer mom. I think Mom has a bottle of this. It's really nice. The candles are a nice touch. Obviously more for her than me. I'm going to need to be careful and take it slow. She's clearly nervous."

Out loud, James states, "Should I make the joke 'Honey, I'm home?"

Sarah's shock intensifies in her frozen position at the sound of his voice, as she was rushing to finish her preparations. She jumped horribly when he knocked. She slowly stands up slowly, and pivots. She feels like her body is being controlled like a puppet. Even with the only light being from the candles, she knows who he is immediately. No one can come close to looking or sounding like her ex-husband like her eldest son. Her jaw feels like it's creaking as it falls open.

"NOOOOOO! NO! NO! NO! NO! NO! This can't be!" her internal voice is screaming at top volume. "I've really fucked this up. There is no recovering from this. And at my daughter's wedding. I am the worst fucking mother ever." Sarah can feel the goose flesh spread across her body.

James' inner voice is just as shocked but for different reasons, "WHOLE. LEE. FUUUCK! I could kiss Uly. He delivered in spades on his promise." James' eyes hungrily drinks in the vision in front of him. Soft supple curves at the bust and hips. Hints of a stomach that is trying to tighten up but will never go back to its youthful state due to multiple childbirths. He notes the he feels odd finding her stretchmarks and scars appealing. Toned arms barely visible because of the robe. And deliciously THICC thighs. Her matching underwear is a thrill to James. He has become so accustomed to randomly matched items because the women he's dated that are his age don't pay as much attention those kinds of details. His libido is in shock as well and doesn't know what to do with the prime opportunity that it has been presented.

Sarah's voice is unsure and crackly, "Are. Are those. Those flowers for me?" she asks as her hand slowly raises to point at the bunch in James' off hand that's also holding his bag. James looks down at his hand and sees the flowers that he bought earlier at Ulysses' suggestion.

Thinking to himself, "Wait, what?" He suddenly finds himself on the defense. Her question about something so mundane has knocked him out of his previously predatory attitude. The simple innocence of the question bothers him.

His left hand drops the key card without acknowledging its existence. It then pulls the bouquet out of his hand, so that he can put he bag down. Taking a step towards her offering her the flowers, he says, "Well, um, yes. They are for you. I, um, remembered that ladies like flowers. And I was definitely expecting a lady. And, um..."

"But daisies?" She asks out loud feeling confused. She asks herself, "Did he know that it would be me?"

James slowly raises his hand clutching the flowers after dropping the the bad, "Yeah... No, I, um, I was thinking about you when I bought them, but it was more like, 'Well, Mom likes daisies, so this lady should like them too." He says as she gently takes the flowers from his hand.

She practically shoves them into her face to avoid the awkwardness. She absentmindedly walks by James to find something to put the flowers into. Unconsciously, she slides her hand across his chest as she walks by him. She doesn't notice the robe falling off of her shoulders, being lost in her thoughts. She eventually decides to use the ice bucket as a vase. Libido? What's that? Oh, here we go. James' dick lurches as a rush of blood fills it up. He slowly inhales her smell as she walks by, strengthening his arousal.

His eyes follow her every move, watching how she gracefully walks around. Once she has finished fussing with the flowers. She looks at him directly in the eyes. He's been too distracted by watching her walk around the hotel room. Studying the movement of her muscles and the way she moves around the room. Without saying anything she returns to him. Sliding one arm around his back and resting the other on top of his chest, she rests her head in the crook between his chest and collar bone, facing his throat. Sarah pays special attention to his cologne. James wraps his arms around her shoulders and rests his cheek on the top of her head.

They stand there for several minutes enjoying the warmth of the other's body. Sarah fights to keep her wits about her. James struggles with staying appropriate for the time being. He knows that things while become inappropriate soon enough.

#####

"Mom! Have you seen my Spanish textbook?!" a teenage James shouts from the living room.

In their bedroom, Trent growls, "Seriously? You pamper him too much. He's an idiot. There's no remembering where he puts things."

"Honey, it'll be ok." Sarah explains from the en suite bathroom where she is putting on her make up. Shouting, "Jimmy have you looked in your bedroom yet?"

"It's not in there, Mom!"

"Girls? Can you help your brother out?" she shouts as she finishes her mascara.

Heather hollers, "We tried, but he's being an ass about it."

Madison yells across the house, "If he calls me a bitch one more time, we'll need to take him to the ER, Mom."

She puts down her perfume bottle in a huff. Muttering to herself, "That book is in his room, I know it." She walks the short distance to the boys' room. She sees it immediately. Open and on his desk. Right where he left it last night after studying. In the exact position that she found her son's face slumped into it. "Jimmy, come to your room." She picks it up as she turns to face the door to meet her eldest son.

At the door, James' mind is blown. He sees Sarah in all of her voluptuous and 'fluffy' glory, covered up only in a matching set of lacy blue bra and panties. She hasn't yet had to deal with the rapid weight gain from the impending divorce that will take her by surprise. He barely stutters his gratitude as he takes the book from her hand and shove it into his book bag.

Sarah bundles James up into a hug, hoping to help calm him down. He is startled by this sudden embrace. His head lands squarely in the center of her bosom. Trying to slow down his breathing because he doesn't want to seem creepy. He inhales a big breath of her perfume.

That. That is the day that young James develops his fetish, without knowing what a fetish is or what the hell is happening.

#####

Sarah sits on the open tailgate of her SUV on the side of the road, waiting for help to arrive. She is getting nervous with the sun setting. She checks her watch repeatedly. She does not like being on an elevated highway with minimal room for traffic. She notices a tow truck slowing down and stopping in front of her car. She knows that she had not called for a tow truck. She called her husband.

A strange man in a florescent vest makes his way towards her. Traffic is giving them more space as his flashing lights looks like a cop car.

"Hey, I got your call." the man shouts over the traffic noise.

"I didn't call you. Who are you?" Sarah shouts back.

The man grins at her. She does not like the vibes that she's getting.

"I'm here to help you, ma'am."

"You didn't answer my question. Who are you?"

"Don't worry, ma'am. We'll get you out of here quickly."

"No! I don't want to go anywhere with you. I want to wait for my husband to come get me."

With a smarmy and ricktus grin, the tow truck driver gets uncomfortably close to her. She can smell something on him. Not alcohol. Not pot. It's something that she doesn't recognize. A smell that revolts her stomach. She also notices that he's missing way too many teeth. His breath is horrible.

Sarah tries to avoid him touching her or her car. She spends several minutes panicking that this guy is trying to do something. He keeps trying to touch her is a way that he thinks is reassuring. He knows that she knows that she's in danger without fully recognizing the danger that she is in. He gets a thrill out of her panic.

"Hey, Mom! Why did you call Bexar Guadaluape Better Get Going Towing?" a voice stumbles over the traffic noise. "You knew I was on my way."

Creepy dude spins to turn around to see a young man working his way towards him and Sarah. He shouts, "No poaching, asshole!"

"What the fuck are you talking about? This is my mother. I'm here because AAA said that it would be two hours before someone could help her. And your truck definitely does not have a AAA sticker. So doesn't that meant that you don't have a AAA endorsement?"

"Go away, kid! This is my tow! I found it first!" he shouts. Sarah is already making a hasty retreat to her son.

"No. I'm not leaving my mom with you... Meth mouth." James shifts around so that his mother is behind him. Once behind him, she sees the Bowie knife hanging from his belt.

"What the fuck did you say?!" the tow truck driver bristles at the insult. Sarah finally realizes what she has been smelling.

"Go back to your truck. I've already sent out photos of your tags. Your best option is to just leave."

"How in the fuck could you have..." the tow driver looks at his truck and then notices that there is a pick up truck parked in between his truck and the targeted SUV. "You poaching motherfucker!"

"I'm not poaching, dick for brains. But you know what? You can try to convince them to take your side. And I've already sent those photos to them," James provokes the tow driver while pointing over his shoulder. The cop car siren whoops to get traffic to move over more.