Day 15 - Truth or Dare/Drunk Sex

Day 15 - Truth or Dare/Drunk Sex

The night had started innocently enough—well, as innocent as things ever got between Ava and Deborah. They were halfway through a bottle of top-shelf tequila, sprawled across the couch in Deborah's mansion, laughing over some ridiculous story Ava was telling about her college days. The room was filled with the lazy warmth that only came from being just drunk enough to forget the world outside.

Ava, in her usual tipsy fashion, had suggested a game. "Let's do something fun, you know?" she slurred, waving her glass in the air. "Truth or dare. Classic. Messy. Dangerous."

The older woman raised an eyebrow, her smirk teasing as she swirled the remaining tequila in her glass. "Truth or dare? What are we, twelve?" she asked. She was always sarcastic. She didn't not do sarcasm. If sarcasm could be trademarked, Deborah Vance would own it. Still, there was something in her eyes. If Ava wasn't so drunk, she might be able to read it.

"Come on," Ava whined, leaning closer to Deborah on the couch, her cheeks flushed from both the alcohol and the excitement of the idea. She was always touchy feely with her boss. It was just who she was, at least in the contexts of Deborah. "Don't be a buzzkill. I bet you can't handle a little truth or dare."

Deborah's smirk deepened, her eyes gleaming as she set her glass down on the table. "Sweetheart, I could handle a hell of a lot more than you think. But fine. You want to play? Let's play."

Ava clapped her hands together, bouncing slightly in her seat like a toddler at Chuck E. Cheese with unlimited tokens. "Yes! Okay, okay. You go first. Truth or dare."

The older woman leaned back against the couch, crossing her legs as she eyed her employee with skepticism. "Dare, obviously."

Ava's eyes lit up, already buzzing with both ideas and booze. "Ooh, okay," she slurred just a tiny bit, tapping her chin dramatically as she tried to come up with something that would throw Deborah off her game. After a moment of deliberation, she grinned. "I dare you to… text Marcus and tell him you've decided to retire and hand over your whole empire to him."

Deborah laughed, the sound low and throaty as she shook her head. "That's your dare? Really?"

Ava giggled, leaning forward on the edge of her seat. Luckily, her hands were braced and it was unlikely she was going to fall off the couch even in her state. "Come on, it'll be hilarious! His reaction alone will be worth it."

Deborah rolled her eyes but reached for her phone anyway. "Fine, but if this backfires, I'm blaming you." She typed out the text, her fingers moving quickly across the screen before showing it to Ava as proof. "There. Happy?"

Ava snorted, nearly choking on her drink as she imagined Marcus's face when he read the message. "Oh, this is going to be good," she said, wiping a tear from her eye.

The comedian set her phone down, her gaze narrowing slightly as she looked at her writer. She still thought this was stupid idea. "Your turn. Truth or dare?"

Ava hesitated for a moment, already feeling a little too tipsy to think straight, not that she was anywhere near straight anyway. "Dare."

"Oh goody." There was more sarcasm there than there was before. Still, there was a wicked gleam in Ava's eyes. "I dare you to…" she paused for dramatic effect, "take off your shirt and wear it on your head like a turbin for the rest of the game."

Ava burst out laughing, setting her glass down so she wouldn't spill it. "That's it? You think that's going to embarrass me?" she teased, already pulling her shirt over her head and twisting it into a makeshift hat. "You'll have to do better than that, boss. I practically lived without a shirt in my early twenties."

"I assume you weren't sober for most of that?"

The younger woman stuck out her tongue. "Nope. Wait. Yes, but I was also high so…"

They went back and forth like that for a while, the dares getting progressively sillier as the tequila kept flowing. By the time they were on their third round, they were both laughing so hard that Ava had almost fallen off the couch twice and needed to be pulled back up by Deborah.

But then, somewhere around the fourth shot, things started to shift. The playful teasing turned into something more charged; the dares began pushing boundaries.

The drunk writer took a deep breath, her head spinning slightly from the alcohol, as she leaned in closer to Deborah. "Okay, your turn again. Truth or dare?"

Deborah raised an eyebrow, her eyes darkening slightly as she smirked. "Truth," she said, her voice softer now, more serious.

The redhead blinked, momentarily thrown off by the change in tone. She had been expecting another dare, something ridiculous or embarrassing, but now, with Deborah watching her so intently, the mood felt different. More intimate.

But that was wishful thinking right? Ava always seemed to think Deborah was one strap away from sleeping with her. She just hadn't found the right button to push her yet. They had too much chemistry for that not to be true.

"Do you ever… you know… regret anything? Like, with us?"

The legend's smirk faltered for a split second, her gaze softening as she studied her employee. There was a long pause, the air between them heavy with unspoken things. Finally, Deborah sighed, leaning back against the couch.

"I don't do regrets, Ava," she said quietly, her voice losing some of its usual sharpness. "But sometimes I wonder what it would've been like if things were… different. If we didn't have all this other stuff between us."

Ava stared at her, feeling the weight of Deborah's words settle over them. She hadn't expected an answer like that, hadn't expected Deborah to be so honest. Deborah Vance didn't do vulnerable. Just as she was about to say something, the older woman interrupted her.

"But that's not the kind of question we're playing for, is it?" Deborah said, her smirk returning as she leaned closer to Ava, her hand reaching out to brush a strand of hair away from her face. "Your turn, sweetheart. Truth or dare?"

Ava swallowed hard, her pulse racing. The intensity of the moment had thrown her, but she wasn't about to back down. "Dare," she whispered, her voice trembling slightly.

Deborah's smirk widened, her fingers trailing lightly down Ava's arm as she considered her next move. "I dare you to…" she leaned in closer, her breath warm against Ava's ear, "kiss me. Right here, right now."

Ava's heart skipped a beat. Kiss her? Deborah had said it so casually, like it was the most natural thing in the world, but Ava could feel the heat rise in her face, her pulse pounding in her ears. She had joked about something like this happening, even fantasized about it on way too many occasions, but this was real and not just another figment of her high imagination. Deborah Vance was sitting right next to her, daring her to kiss her.

The redhead tried to play it off, forcing a laugh as she leaned back a little, giving herself room to breathe. "You want me to kiss you? Are we still playing the game or is this something else?"

"You said dare, didn't you? Don't get cold feet on me now, Daniels."

Ava hesitated for only a second longer, the tequila buzzing in her system giving her the courage she usually lacked in moments like these. She scooted closer, her hands trembling slightly as she reached out, cupping Deborah's cheek. She leaned in, her lips brushing against Deborah's. The kiss was soft, tentative at first, like they were both testing the waters. Ava's pulse quickened as Deborah didn't pull away, didn't laugh it off like a joke. Instead, she pressed back, her hand resting lightly on Ava's thigh, her fingers curling into the fabric of her jeans.

The younger woman deepened the kiss, her nerves dissolving as she felt her boss respond, the heat between them building quickly. The room seemed to shrink, the world outside fading away as the kiss grew hungrier, more urgent. Ava's hand slid up to tangle in short non-wig hair, pulling her closer as their mouths moved together, tasting the tequila on each other's lips.

Deborah's grip tightened on Ava's thigh, her body shifting so she could press against her more fully. The kiss was anything but slow now, their tongues sliding together in a heated rhythm that left Ava breathless. She couldn't believe this was happening, couldn't believe that she was kissing Deborah Vance in her mansion, their hands roaming over each other like it was the most natural thing in the world.

Finally they pulled back, gasping for air as they rested their foreheads together. "That was…"

Deborah chuckled softly, her fingers brushing over Ava's lips as she looked at her with that same teasing glint in her eyes. "See? That wasn't so hard, was it?"

Ava swallowed. "No… but it's definitely not where I thought tonight was going."

The older woman's hand moved to rest on her employee's cheek, her thumb brushing lightly over her skin. "Well, you did say you wanted to play a messy, dangerous game," she said, her voice low and smooth. "And I'm all for a little danger."

Ava's heart raced again, her pulse thudding in her chest as she looked at Deborah. Still, she couldn't stop thinking about what the other woman would like without clothes. "What now?"

Deborah's eyes darkened, her hand sliding down to rest on Ava's waist. "That depends, sweetheart," she said, her voice full of a dangerous edge. "Are you ready for the next round?"

Ava had a dumb grin now. "What's the dare?"

The comedian's smirk returned, her hand slipping lower to grip Ava's hip as she whispered, "I dare you to take this upstairs. Unless you're too scared."

Ava's heart leapt into her throat. There it was—an invitation, a challenge. She eagerly lept off the couch, half tripping into standing up but managing to right herself.

"Seriously?"

Ava took the smirking woman's hand, her heart racing as pulled her up the stairs. She knew this was crossing a line—a big one—but the excitement of it, the heat of Deborah's hand in hers, was too intoxicating to resist.

Once they reached Deborah's bedroom, the tension between them was palpable. The younger woman led Deb to the edge of the bed, but it was the comedian who pushed her down gently onto the bed.

"You think you can handle this?" Deborah taunted, her voice low, teasing, as she knelt in front of Ava. She didn't wait for an answer, her hands already working at the button of Ava's jeans, sliding them down her hips in one smooth motion.

Ava's breath hitched, her body trembling with a mix of anticipation and alcohol-induced dizziness. "I… I can handle it," she whispered, though the words came out more breathless than she intended.

Deborah smirked as she hooked her fingers into the waistband of Ava's panties, pulling them down with the same slow, deliberate motion. "We'll see," she muttered, her voice thick with amusement as her hand slid between Ava's legs, her fingers trailing over her slick entrance. "Looks like you're ready for me."

Ava's head tipped back, a soft moan escaping her lips as Deborah's fingers brushed against her, teasing but not giving her what she really wanted. She could feel the heat building between them, her entire body humming with need as Deborah's touch became more insistent.

"Deb…" Ava whimpered, her hips bucking slightly as Deborah's fingers finally slipped inside her, curling in just the right way that made her toes curl.

"Shh," Deborah whispered, her free hand pressing against Ava's thigh to keep her still. "Just let me take care of you, sweetheart."

Ava's breath came in short gasps as Deborah's fingers moved inside her, the sensation sending waves of pleasure coursing through her body. She was so tipsy, so turned on, that everything felt magnified—the touch of Deborah's hand, the warmth of her breath, the low, throaty sound of her voice as she murmured soft praises.

"You like that?" Deborah muttered, her fingers moving faster, deeper, as her thumb circled Ava's clit with slow, deliberate pressure. "You're so wet for me."

Ava couldn't respond, her brain too fogged with pleasure and alcohol to form coherent words. All she could do was nod, her body trembling as Deborah pushed her closer and closer to the edge. It was too much, too intense, and yet, it wasn't enough. She needed more, needed Deborah to take her over the brink.

Deborah's pace quickened, her fingers thrusting harder, faster, as she leaned in closer, her breath hot against Ava's ear. "Come for me, Ava," she growled, her voice full of command. "I want to feel you come on my fingers."

That was all it took. Ava's body arched off the bed, her hands gripping the sheets as the orgasm ripped through her, her entire body shaking with the force of it. She cried out, her vision going white for a moment as wave after wave of pleasure crashed over her.

Deborah didn't stop, her fingers still working Ava's body, drawing out every last bit of the orgasm until Ava was a trembling, gasping mess beneath her. But then, as the pleasure started to fade, so did Ava's grip on consciousness. The alcohol had hit her hard, and the intensity of the orgasm had drained the last bit of energy she had left.

Before she even realized what was happening, Ava's body went limp, her eyes fluttering shut as she passed out, completely spent.

Deborah stared down at her, her fingers still inside Ava as she blinked, clearly surprised by the sudden shift. She pulled her hand away, wiping it on the bedspread with a soft sigh as she stood up, shaking her head.

"Great," she muttered under her breath, rolling her eyes as she glanced at Ava's passed-out form. "You really know how to pick your moments, don't you?"

With a resigned sigh, Deborah pulled the blankets over Ava's body, tucking her in as she stood there for a moment, watching her sleep. She smirked to herself, shaking her head again. "You're going to feel this in the morning," she muttered, before turning off the light and heading toward her own side of the bed.