Best Night Ever

Part 1: The Pickup

by David Banner

Tags: #college #dom:male #f/f #f/m #multiple_partners #pov:bottom #sub:female #alcohol #anal #cum #cum_play #friendship #gangbang #vaginal_sex
See spoiler tags : #piss #watersports

Hello all, this is part of my writing challenge to myself to write at least 3,000-4000 words each week that started with the New Year (my previous stories were written during NaNoWriMo). An uncomfortably high goal? Maybe!

A few notes on this one: First, it’s technically in the same universe as Apex Team Building, but there isn’t really any overlap between them nor is there a correct “read order” between them, the only thing really is that the mind control works the same way. Second, this story is based off of the idea that getting to know the characters and sort of believing them as actual textured people makes the debauchery later on more fun (and it will get debauched in later chapters). But understand that parts one (and to a certain extent two) are going to be comparatively tame.

Emma Holloway had spent four years being the one who kept things from falling apart.

Four years of holding hair back in bar bathrooms. Four years of cutting off friends who’d had too much, calling Ubers, making sure everyone got home safe. Four years of being the designated driver, the emergency contact, the person everyone trusted to remember where they’d left their phones and whether they’d paid their tab.

She was the shepherd. The safety net. The girl who stayed sober enough to handle disaster so everyone else could have fun without consequences.

She was tired of it.

But being responsible was how she’d maintained a 4.0 GPA in a double major: English and Computer Science. Two fields that had nothing to do with each other, that required completely different parts of her brain, that her advisor had warned her would be “almost impossible to balance.” She’d balanced them anyway. That was what Emma did. She managed the impossible through sheer force of organization, discipline, and never, ever letting herself slip.

It had cost her, of course. Her last boyfriend, Derek (she still couldn’t believe she’d dated a Derek), had broken up with her sophomore year because she “wasn’t present.” Before him, Skyler, freshman year, same story. The sex with both of them had been... fine. Sometimes even good. But she’d never been able to turn off the part of her brain that was calculating how much study time she was losing, mentally organizing tomorrow’s to-do list while he moved inside her. She’d decided after Derek that she just didn’t have time for relationships. Not if she wanted to graduate with honors. Not if she wanted to keep her scholarship.

But tired as she was, she wasn’t tired enough to stop being responsible. That wasn’t who she was.

Still, when she looked in the mirror tonight, auburn hair curled soft around her shoulders instead of pulled back in her usual practical ponytail, pale skin dusted with actual makeup, freckles she usually ignored now highlighted with something shimmery, she made herself a promise.

Tonight, I’m going to have fun.

Real fun. Not caretaker fun, where she spent the whole night tracking everyone else’s drinks and watching the clock. Tonight was Lily’s twenty-first birthday. They’d just survived finals. If there was ever a night to let go, it was this one.

She checked her phone. The group chat was blowing up.

Megan:

IM SO READY TO GET FUCKED UP TONIGHT 🍾🍾🍾

Lily:

omg omg omg I’m so nervous I’ve never been drunk drunk before

Hannah:

Should I bring a jacket? I don’t know what to wear

Jo:

Just wear whatever. It’s a bar crawl not a fashion show

Megan:

Jo don’t be a buzzkill!! Lily this is YOUR NIGHT we’re gonna make it LEGENDARY

The party bus had been Megan’s idea. She’d found the service online, some VIP pub crawl experience that promised “the best night of your life” and charged accordingly. They’d split the cost five ways, booked their spots weeks ago, and now the night was finally here.

Emma smiled despite herself. She grabbed her clutch and headed out.

* * *

The pickup spot was a parking lot at the edge of campus, far enough from the main buildings that the university wouldn’t notice a party bus idling there. Emma arrived to find the others already gathered, a cluster of nervous excitement under the streetlights.

The asphalt was still warm from the day’s heat, radiating up through her heels. Someone’s perfume drifted on the evening air, mixing with the distant smell of cut grass from the quad.

Lily spotted her first.

“Emma!” The birthday girl bounced over, nearly tripping on her heels. Lily Morrison had a face that would certainly make bouncers squint at her ID long after they should’ve stopped. Shoulder-length blonde hair in soft waves, a heart-shaped face that still held baby fat in her cheeks, wide blue eyes that made her look perpetually surprised by the world. She was wearing a white sundress that made her look like she was headed to a garden party rather than a pub crawl, complete with a sparkly sash that read FINALLY LEGAL and a plastic tiara already slightly askew.

“I can’t believe it’s finally happening,” Lily gushed, grabbing Emma’s hands. “I’ve been waiting for this for, like, literally years.”

Emma knew she meant more than just the party. Lily was the kind of person who’d felt genuinely uncomfortable the few times she’d had a beer before turning twenty-one. “It’s illegal,” she’d said once, completely serious, when Megan had tried to hand her a drink at a house party. “I know that sounds ridiculous, but I just... I can’t enjoy it if I’m breaking the rules, you know?” She’d spent the whole party nursing a Sprite, cheerful but somehow apart from the rest of them.

Tonight was different. Tonight, for the first time, the world was officially giving her permission to be an adult. She’d been eighteen for three years, technically legal in every other way, but this was the final barrier. The last rule. And Lily Morrison did not break rules.

Emma had met Lily freshman year in their dorm. They’d been assigned as roommates by some algorithm that somehow knew they’d balance each other out: Emma’s careful planning against Lily’s cheerful chaos, Emma’s guardedness against Lily’s open heart. Three years later, they were inseparable—the core of their friend group, the axis around which everyone else orbited. Emma remembered the time Lily had stayed up all night with her before her first CS final, making flashcards and quizzing her on data structures, even though Lily was a communications major who didn’t understand a word of it. That was just who Lily was.

“You look amazing,” Emma said, and meant it.

“You look amazing!” Lily grabbed her hands, squeezing. “Oh my god, your hair is down! You never wear your hair down!”

It was true. Emma usually kept her auburn waves pulled back, out of her face, practical. Tonight they fell loose past her shoulders, catching the streetlight with hints of copper.

“Special occasion.”

“She cleans up nice, right?” Megan appeared at Lily’s shoulder.

Megan Brooks was impossible to miss. Tall, confident, with dirty blonde hair that fell in beachy waves past her shoulder blades, and a body she’d clearly dressed to show off: a tight emerald tank top that strained against her considerable chest, a tiny floral skirt, strappy heels that added three inches to her already impressive height. Her face was all angles and attitude: sharp cheekbones, a knowing smirk, full lips usually curved in challenge. Where Lily was soft and sweet, Megan was sharp and hungry.

She was already holding a bottle of something that was definitely not legal to drink in a parking lot.

“I told you guys, tonight is going to be insane.”

Megan had joined their group sophomore year through sheer force of personality. She’d sat down at their lunch table uninvited, declared them her new best friends, and somehow made it true. The thing about Megan that nobody expected was that she was also terrifyingly smart. A 3.9 GPA in biochemistry, nearly as high as Emma’s, maintained while also being the center of every social event on campus. Emma had no idea how she did it. She’d asked once, and Megan had just shrugged: “I don’t need much sleep, and I read fast. What’s the mystery?”

“Megan, you’re already drinking?”

“Pre-gaming, babe. Catch up.” Megan thrust the bottle toward her.

Emma took a small sip. Vodka, cheap and harsh, mixed with something artificially fruity. It burned going down. She passed it back.

She scanned the group for the others.

Hannah Novak was standing slightly apart, fiddling with her glasses. She was the newest addition to their friend group, a junior transfer who’d ended up in Emma’s study group and somehow stuck around. Curly brown hair fell past her shoulders, framing a round face with soft features and warm brown eyes magnified slightly by thick-rimmed glasses. She’d clearly tried to dress for the occasion, swapping her usual modest sweaters for a cropped mint top that showed a sliver of midriff, but her body language screamed discomfort: arms crossed over her chest like she was trying to hide, shoulders hunched.

Hannah had been raised by strict evangelical parents in rural Pennsylvania who’d kept her on a very short leash until college. Emma had learned this in fragments over study sessions—and over the Gilmore Girls marathons they’d started doing together on Thursday nights, working through the series while Hannah asked endless questions about pop culture references she’d never been allowed to encounter. The homeschooling until high school. The purity pledges. The assumption that by now, at twenty-one, Hannah would be married with her first kid on the way.

Coming to this university had been Hannah’s first real act of rebellion. Not drinking, not partying, not even the cropped top. Just... being here at all. Getting an education her parents thought was unnecessary for a woman. Every class she attended, every test she passed for her computer science degree, was a middle finger to the life they’d planned for her.

The whole group felt protective of Hannah in a way they didn’t need to feel about each other. She was the one they all looked out for, the one they made sure got home safe, the one they explained jokes to without making her feel stupid for not getting them.

“I mean, it’s fine, I just—I don’t know if this looks okay,” Hannah was saying to no one in particular, tugging at her top. “Is it too much? I feel like it’s too much.”

“Hannah! You look great!” Emma called out.

Hannah’s cheeks flushed pink. “I feel weird. Is this too much?”

Megan looked Hannah up and down appraisingly. “Honestly? You could show more. You’ve got a body under all those sweaters, might as well let people see it.”

The words landed wrong. Emma saw Hannah’s face crumple slightly, saw her arms tighten across her chest.

“Megan,” Emma said quietly.

Megan caught herself, saw what she’d done. Something flickered across her face—not just remorse but something rawer, a flash of the person underneath all that confidence who actually gave a shit about getting it right. She covered it quickly, but Emma caught it. “Shit. Hannah, I didn’t mean—” She stepped closer, put a hand on Hannah’s arm. “You look beautiful. Seriously. I’m just being an asshole because I’m already drunk. The top is perfect. You’re perfect. I’m sorry.“

Hannah’s posture softened slightly. “It’s okay. I mean, I know I’m not used to—”

“No, I was being a dick. Come here.” Megan pulled her into a hug, and Emma watched Hannah relax into it. “Tonight’s going to be fun, okay? We’ve got you. All of us.”

“Thanks,” Hannah said, muffled against Megan’s shoulder.

And then there was Jo.

Jo Brennan was leaning against a lamppost at the edge of the group, scrolling through her phone with practiced disinterest. She been out since high school, openly gay and aggressively unbothered by anyone’s opinion about it. Short dark hair with a sharp undercut, a lean athletic build, a geometric tattoo visible on her upper arm. Her face was angular, almost severe: strong jaw, direct gaze, the kind of features that read as handsome rather than pretty.

Tonight she’d made a concession to the occasion: instead of her usual ripped jeans and band tees, she was wearing fitted black pants and a silky button-down, sleeves rolled to show off her forearms and the edge of her tattoo. Still unmistakably Jo, but elevated. Like she’d acknowledged this was an event worth dressing for.

Jo had transferred in sophomore year for her psychology degree, same year as Megan, but through completely different channels. She’d been assigned as Emma’s lab partner in the organic chemistry class they both had to take as a prerequisite, and they’d bonded over mutual hatred of the professor and a shared appreciation for dark humor. Jo was the person Emma texted when she needed someone to be blunt with her. The person who’d never once made Emma feel like she had to perform.

The funny thing about Jo was that she had a whole other friend group—her lesbian crew, she called them, a tight circle of queer women she’d found through the campus LGBTQ center. But somehow, she always seemed more comfortable here, with Emma and Lily and the others. “Less drama,” Jo had explained once, when Emma asked. “My gay friends are great, but everything’s always so... loaded. With you guys I can just be.”

Emma had noticed, too, the way Jo watched Megan. The careful way she positioned herself, always aware of where Megan was in a room. The way her eyes tracked Megan’s movements, then quickly looked away if anyone noticed. It was subtle—Jo was good at playing cool—but Emma was observant by nature. She’d seen the discipline it cost Jo to look away each time, the slight tension in her jaw, the way her hand would find something to do to cover the redirect. She suspected Megan wasn’t dumb enough to miss it either. There was something in the way Megan touched Jo that suggested she knew exactly what effect she was having.

Jo looked up from her phone, caught Emma’s eye, and gave a small nod of acknowledgment. Cool and collected, as always.

“Okay, everyone’s here!” Megan clapped her hands. “Where’s this bus? The booking said 8 PM pickup and it’s already—”

Headlights cut through the parking lot.

The bus that pulled up was impressive. Massive and sleek, windows tinted so dark they were basically black, LED strips running along the undercarriage in a subtle purple glow. It looked expensive. Exclusive. Worth every penny of the group rate they’d paid.

The door hissed open, and a man stepped out.

He was average. That was Emma’s first impression. Average height, average build, the kind of face you’d pass on the street and never remember. Wearing jeans and a casual button-down, he was in his late twenties, maybe early thirties. Just on the edge of being too old to be running a pub crawl for college students, but countering that with an easy affability.

“New pickup!” His smile was warm. “Welcome aboard. I’m Ryan, I run these crawls. You must be the birthday group?”

“That’s us!” Lily waved, tiara glinting. “I’m Lily. It’s my twenty-first !”

“Happy birthday, Lily. You’re going to have an incredible night.” Ryan stepped aside, gesturing to the bus. “Hop on. We’ve got a few other guests already, picked them up across town. Everyone’s friendly, I promise.”

Emma climbed the steps, the leather-and-cleaning-fluid smell of the bus hitting her immediately. Three guys were already settled in the back with drinks in hand. They looked up as the girls entered, interest flickering across their faces.

“Ladies,” the tallest one said, raising his beer. He was good-looking in a frat-boy way, confident smile, eyes that lingered too long on Megan’s chest. “Welcome to the party.”

“I’m Tyler,” he continued. “That’s Jake and Connor. We’re celebrating too. End of finals.”

“Same !” Lily said brightly. “Well, that and my birthday.”

“No shit? Happy birthday.” Jake, the stockier one, was already focused on Lily, watching her with undisguised appreciation. “Drinks are on us, birthday girl.”

Connor, quieter than the others, just nodded. His eyes moved across the group assessingly before settling near Hannah.

Other customers, Emma told herself. Just other people who booked the same bus. This is how these services work.

She found a seat, the leather cool against the backs of her thighs where her skirt didn’t cover. The bass from the bus’s sound system thrummed through the seat, vibrating slightly against her skin.

Ryan pulled the door closed and the bus started moving. Emma noticed there was no view of the driver—a solid partition separated the passenger cabin from the front cab, tinted glass offering no glimpse of whoever was actually driving them through the city.

* * *

Ryan made his rounds while the girls got settled, topping off drinks, making sure everyone was comfortable. The bus interior was impressive: leather seats lining the walls, a full bar gleaming at one end with bottles backlit in purple and blue, a brass pole in the center catching the LED lights.

Megan was already testing the pole, her dirty blonde hair swinging as she spun. “Remember sophomore year?” she called to Emma. “When I tried to pole dance at that frat party and fell on my ass?”

Emma laughed. “You knocked over like three guys.”

“Dominoes, baby. I took out the whole front row.” Megan spun again, more gracefully this time. “Been practicing since.”

Emma noticed Jo watching Megan spin—the way her eyes tracked the movement of Megan’s body, the deliberate casualness of her expression. When Megan caught her looking, Jo’s gaze slid away smoothly, like she’d been looking at something else the whole time.

Lily was taking selfies, tiara glinting. Hannah was perched nervously on a seat, clutching a drink someone had pressed into her hand, condensation dripping onto her fingers. Emma watched her—the way she held herself, the uncertainty in her posture—and felt that familiar protective impulse.

We’ve got her, she reminded herself. That’s what we do.

Emma watched Ryan work the room, sitting with each of her friends in turn, having quiet conversations she could only catch fragments of.

He started with Lily, the birthday girl practically vibrating with excitement, her blue eyes wide.

“Twenty-one,” Ryan said. “That’s huge. How does it feel?”

“Honestly? Like, finally, you know? I’ve been waiting for this for so long. Not just the party but... being allowed. Like, I know it sounds silly, but I couldn’t really enjoy anything before because it wasn’t... I wasn’t supposed to, you know?”

“You’ve been waiting for permission. The world telling you it’s okay to live.”

“Yes !” Lily’s face lit up. “That’s exactly it. And now I have it. I’m allowed.”

“Then tonight, you take that permission and run with it. It’s your night. Your rules. Whatever feels good, you chase it. No holding back. Say it.“

“My night. My rules. No holding back.”

“There you go.”

He moved to Hannah next. She was clutching her drink like a lifeline, glasses slightly fogged from nerves.

“You’re Hannah, right? The others mentioned you’re newer to the group.”

“Yeah. I transferred last year.”

“And you’re... not used to this kind of thing. Parties. Going out.” He said it gently, without judgment.

Hannah shook her head. “My parents were really strict. I didn’t really... I mean, they thought I’d be married by now. I wasn’t even supposed to go to college.” She laughed, but it came out shaky. “Just being here is, like, the biggest rebellion of my life.”

“You haven’t experienced things. And now you’re surrounded by people who have, and you feel behind. Like you missed something.”

“Yes.” Her voice was small. “Exactly.”

Tonight’s your chance to catch up. Here’s your new rule: whenever you’re not sure what to do, you say yes. That’s it. The answer is always yes. The girl who says no stayed back at the dorm. You’re someone new tonight. Say it.“

“The answer is always yes.”

“Perfect.”

Then Jo. This one was different. Jo’s body language was relaxed, confident, but Ryan approached her the same way he’d approached the others. Sat next to her at the bar, poured her a drink.

“Jo?”

“Yeah.”

“You seem like you know yourself. I respect that.”

Jo’s mouth quirked. “I’ve had enough time to figure it out.”

“But here’s the thing.” Ryan leaned in slightly. “You know who you are. You’re comfortable with it. But sometimes you look at your friends and wonder if you really fit. If they see you as one of them or just... the different one. The outsider.”

Something flickered in Jo’s eyes. She covered it quickly. “I don’t really care what people think.”

“Of course not. But tonight, you could try something different. Stop being the one who’s slightly apart. Whatever they do, you do. No barrier between you and them. Just... be part of it. Completely. Sound good?“

A pause. Then Jo shrugged. “Yeah. Okay. No barrier.”

Then Megan. She’d dismounted from the pole and was helping herself to more drinks at the bar. Ryan approached her with a knowing smile.

“You’re Megan.”

“The one and only.” She looked him up and down appraisingly. “You run a good operation here.”

“Thanks. And you’re the one everyone watches, aren’t you? The life of the party. The one who makes things happen.”

Megan preened. “Someone’s got to.”

Tonight, you’re going to set the pace. Show these girls what they’re capable of. Every time things slow down, you push forward. You go first. You show them how far fun can go. Think you can handle that?“

“Oh, I can definitely handle that.”

“Then let’s have a night they’ll never forget.”

Finally, Ryan sat down next to Emma, offering her a fresh drink. The ice clinked against the glass, cold against her palm.

“So. You’re part of the birthday crew. What’s your name?”

“Emma.”

“Emma.” He said it like he was filing it away. “And what’s your role in the group? Every friend group has roles.”

She shrugged. “I’m just... I look out for everyone, I guess. Make sure things don’t get too crazy.”

“Ah.” His smile shifted. Understanding. “The responsible one. Always watching. Always managing. Must be exhausting, carrying everyone else’s fun on your shoulders.”

“It’s fine. I don’t mind.”

“But tonight’s different, right? Tonight you want to actually enjoy yourself.” It wasn’t a question. “Here’s the thing, Emma. You’ve earned a night off. You’ve spent so long taking care of everyone else that you’ve forgotten how to just... be. So tonight, here’s what I want you to remember.” He held her gaze. ”You follow. You don’t lead. You let someone else worry about the details. If something feels good, you do it. Sound fair?“

The words settled into her like stones dropping into water. Solid. Undeniable.

“That sounds fair.”

“Perfect.” He squeezed her shoulder and moved on.

Emma sat there for a moment, feeling strange. Lighter. Like a decision had been made that she hadn’t realized she was struggling with.

That’s what I wanted, she told herself. To let go. He just gave me permission.

She didn’t question why she needed his permission in the first place.

The bus rolled on through the city, windows too dark to see where they were going.

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