Dean wasn’t really a master of tact when he was sober. But he knew he’d been through quite a few beers when he decided that a good conversation opener was, “Charlie, you eat a lot of pussy, right?”
Charlie choked on her drink, slamming the beer bottle down on the table and coughing. Dean leaned over to thump her on the back, standing up and staggering off to find her a napkin or something. He had no clue where they kept napkins in the batcave. He almost wanted to wake up Sam and have him find one—he’s the one who kept cleaning up and putting things god-knows-where—but the guy needed some damn sleep. Dean was worried about his little brother. That’s why he’d sent Sam to bed early rather than letting him stay up for bro time with Charlie. The fact that Sam had agreed spoke volumes about his condition.
Dean finally found a napkin and sort of fell/danced his way back to his chair, sitting down and handing it to Charlie.
“Thanks,” she wheezed, wiping her mouth off. She cleared her throat. “So, um... pussy.”
Dean’s face lit up as he remembered what he was talking about. “Yeah! I was gonna ask...” He took another sip of beer, holding a finger out seriously as he swallowed. “It’s proper vagina etiquette to let your friend-with-benefits know ahead of time if you’re a squirter, yeah?”
Charlie frowned, taking another sip of beer. “Uh... I guess it can’t hurt to mention it.”
“So it doesn’t, you know...” Dean rolled his head in a gesture, regretting it when the room spun. “...go up your nose or anything.”
Charlie snorted into her drink, giggling uncontrollably. “You—you had come go up your nose?”
“She was aiming straight up my nostril!” Dean took a sullen sip of beer as Charlie shook her head, still laughing.
“Wait, wait...” Charlie tried to steady her voice, holding up a hand. “You’re telling me you’ve made a girl squirt?”
Dean shrugged. “Yeah. A couple times.”
Charlie let out a low whistle. “Okay. You know that’s, like... reeeeeally hard for most girls?”
Dean gave Charlie a smug grin. “Uh, yeah. They seemed pretty impressed too.” He took a draw on his beer. “What can I say, I give really good head.”
“You’ve got the mouth for it,” Charlie blurted. She looked panicked as soon as she’d said it, downing her beer as if it could turn back time.
Dean snickered. “Damn straight.”
“I mean no offense but you sir have got cocksucking lips,” Charlie continued, wide-eyed, her mouth clearly ignoring any and all impulses from her brain.
“Clit-sucking, and yeah I do,” Dean replied, leaning back in his chair and licking his lips proudly.
Charlie gulped down another sip of beer, holding up a hand seriously. “Squirting is really impressive.”
“Don’t I know it.”
“You must be pretty good for a dude.”
“Damn straight I’m—wait.” Dean pointed an accusing finger at Charlie. “What do you mean, for a dude?”
Charlie pursed her lips, holding out her hands helplessly. “What can I say, Dean, we’re dealing with the same set of plumbing, only, uh... I’ve got the blueprints.”
Dean’s jaw clenched. “...You saying you give better head then me?”
“Oh, it’s not your fault, of course,” Charlie assured him, taking a casual sip of her beer. “It’s a matter of practice.”
“I’ve had loads of practice!” Dean shot back.
Charlie met his gaze seriously for only a few seconds before she broke down into snorts, then outright laughter.
Dean held his hands out. “What?”
“Loads,” Charlie gasped. “Loads of practice giving head.”
The gears of Dean’s drunken brain churned slowly, then clicked. He snorted as Charlie wiped her eyes, finally starting to calm down.
“The point is,” she gasped, beaming at him. “I give better head.”
Dean slammed his beer down on the table, his smile gone. “Do not.”
Dean stood up suddenly, ignoring the way his chair clattered to the floor. “You want me to prove it?”
Charlie downed the rest of her beer and stood up too. “Yeah. Cause you can’t.”
“That... doesn’t make sense!”
“Your face doesn’t make sense!” Charlie shot back, not perfectly steady on her feet.
Dean pointed at the floor. “Right here. Right now. Oral contest. Let’s go.”
“Fine.” Charlie pulled her jacket off, tossing it onto the floor. Dean pulled his shirt off as she tugged off her own and wrestled with her bra.
“And when I win, you can buy me a bottle of whiskey!” Dean added quickly.
“Fine!” Charlie started undoing her belt as Dean struggled with his. “And—and when . win, you can buy me a draconomicon!”
“I don’t know what the fuck that is!” Impatient with his belt, Dean grabbed Charlie’s waist and sat her down on the table.
“It’s a Dungeons and Dragons manual, you philistine!” Charlie shot back, grabbing Dean’s hair as he kissed down her stomach, tugging her pants off. “It’s a reference book for everything you need to know about... about...” Charlie trailed off as Dean kissed between her legs. “Oh... frack...”
Dean ran his tongue in two broad, wet stripes up the place where Charlie’s legs met her body, one on each side. Then he ran his tongue right up the middle.
Charlie doubled up around his head. “Frack!”
Dean pulled back, frowning up at her. “You actually say that in bed?”
Charlie grabbed his hair and shoved his face back between her legs. “We’re not in bed, and you’re totally going to lose at this rate!”
“Am not,” Dean muttered against her, teasing his tongue in curving lines over her skin. Charlie sucked in a breath, hands tightening in his hair, her face flushed with a combination of alcohol and tongue on vagina. Dean groaned and slipped his tongue into Charlie slowly, grabbing her hips and holding her still as she squirmed.
“S’not—all about—the penetration—” Charlie gasped out in between probing licks of Dean’s tongue. She let go of his hair with one hand to brush her own messy red strands out of her face. “You men get—too hung up on that—oh fuck that’s good—”
Dean pulled back to beam at her, licking his wet lips. “Made you use a real person swear word that time.”
“Losing!” Charlie panted, dragging him back in.
Dean flicked his tongue into her gently, murmuring against her between licks. “Anyway, I know s’not all about the penetra—mmh—tration. Jus’ warmin’ up.”
“Build up. Yeah. That’s good,” Charlie panted, staring hazily at the far wall as Dean nuzzled against her. She swallowed and started speaking more quickly. “I mean. Good for a dude. Not as good as m—oh. Oh fuck.” Charlie gasped and her legs wrapped around Dean, pulling him in. “Oh fuck.”
Dean smirked, rubbing his tongue back and forth just above Charlie’s clit. He brushed his lips in a gentle kiss over it, then gave it a soft lick. Charlie almost fell off the table and he had to hold her still while he licked it again, slowly, swirling his tongue in a languid circle.
Charlie’s voice was wracked with panting. “Oh f-frack, D-Dean, no, you’re s-supposed to lose, really... wanted that... that... draconomonomicon...” Charlie rolled her head back and groaned when Dean sucked on her. “Oh, that’s just ch-cheating...”
Keeping a fluttering suction on her clit, Dean slid a hand up Charlie’s leg and teased a finger into her slowly, ignoring her breathless mutters about “haxors.” He pulled his lips away and flicked his tongue over her clit in gentle, teasing touches, quick and feather-light.
“Aaaaaaaaah that that that right there!”
Dean slipped his finger in and out smoothly, holding Charlie still as he flicked his tongue over her. He refused to move, refused to change his movements until she was shuddering and breathing fast and shallow and not even speaking. Then he pulled back, licked his lips, and curled his fingers up while he swirled his tongue in a hard circle.
Charlie’s legs spasmed and she shouted “Frack frack frack frack frack!” while Dean rode her through it, sucking sporadically and working his fingers in and out. When she was gulping for air, he pulled his fingers out and gave her a smug smile.
“You can buy me the whiskey tomorrow,” he slurred, cocking an eyebrow.
Charlie panted, still out of breath. Swallowing, she shook a stern finger at him. “...I am on a hair trigger when I’m tipsy.” She stabbed a thumb against her chest, raising her eyebrows. “I’ve—I’ve been nerfed. I am a nerfed dungeon.”
Dean frowned. “I have no clue what that means.”
“Doesn’t matter.” Heaving a deep breath, Charlie shoved at Dean’s shoulders. “Lie down, my turn.”
“Charlie—” Dean sighed and let Charlie guide him to the floor and push him down on his back. She started kissing down his neck and Dean held his hands up. “I have a dick, Charlie. We didn’t think this through.”
“Shut up,” Charlie muffled against his chest, undoing his pants. “You’re just scared to lose to a girl.”
“Lose to a—I wouldn’t be playing if you weren’t a—I still don’t have a vagina, Charlie.”
Charlie ignored him, yanking his pants down. Dean let his head fall back against the floor and sighed as she tugged them off his feet.
“Okay, sure. Fine. Just kinda, pretend it’s a vagina in reverse.” Dean held up his hands, squinting at them. “Instead of sticking your tongue in, you wanna—” Dean choked on a high-pitched noise and grabbed at the floor when Charlie shoved his legs up and ran her tongue behind his balls. “Holy fuck!”
Charlie gave a smug little hum and licked him again, teasing the soft skin just above his tight hole. Dean kicked out in alarm, but his cock twitched. “Fuck!”
Charlie frowned up at him. “Could you keep still when I’m eating you out?”
“That’s not—this isn’t—” Dean blew out a shuddering breath when Charlie’s tongue found his hole and lapped over it gently. “Oh Jesus goddamn Christ on a pogo stick...”
Charlie hummed against him again and rolled her tongue in a slow circle. Dean cursed and grabbed at the floor, knuckles whitening. Charlie laved her tongue over him in slow, wet strokes, making noises that to Dean sounded awfully smug, but more importantly, vibrated. He rubbed a hand over his eyes, groaning, chest heaving.
When Charlie’s tongue poked at him, Dean sucked in a frantic breath and grabbed a handful of her red hair. “Oh Christ god fuck—”
“I... take it you’ve never been rimmed before,” Charlie murmured, looking up at Dean from behind his cock.
“Why—why would you even—That’s my ass,” Dean clarified.
Charlie gave him a slow nod, muttered, “Einstein over here,” and nosed back between his legs. Dean groaned and his head rolled against the floor. When Charlie sucked on him, he chewed his lip and grabbed his cock, giving it a stroke.
“Oh fuck oh fuck oh fuck...”
He’d had girls lick his cock before, and that was fucking awesome, but no one had ever asked to go back there. He hadn’t realized how goddamn sensitive it was. Every little lap of Charlie’s tongue felt butter-smooth and made him shiver.
“Christ you’re good at that...” Dean panted, his hand sliding up and down his cock.
“Told you,” Charlie muffled against him. Then her tongue pushed against him and Dean’s head fell back and his eyes widened because her tongue was pushing inside him.
“Oh fuck—” Dean gasped when she pulled it out and teased in again, squeezing his cock. “Fuck.”
“Well, I know who’s winning the swear creativity contest...” Charlie muttered. Dean grabbed a handful of her vivid hair and dragged her close again.
“K-keep going,” he panted.
Charlie smirked and got back to work. Dean closed his eyes and groaned, holding her hair to keep her face buried between his legs while he stroked himself with increasing speed. His breath was coming hard and fast when Charlie grabbed his hips and started full-on tonguefucking him.
“Oh Jesus fucking Christ fuck goddamn it fuck...” Dean panted swear words breathlessly, fingers tightening in Charlie’s hair. The red strands tickled his thighs as she shifted, getting a better angle so she could tongue him deeper. “Agh, god!”
Charlie sucked on him before thrusting her tongue in and Dean bit his lip hard to muffle a scream as he came, come shooting through his hand and all over his chest. He gasped as Charlie licked him again and his cock throbbed against his palm one last time. Charlie propped herself up on her elbows and gave Dean a meaningful look.
Dean swallowed, then shook a finger in the air. “Okay... that was very good.” He cleared his throat. “But. You were a breathless mess when I was done too.”
“I’m pretty sure you were more breathless and messy,” Charlie countered.
Dean gave a dry laugh. “Oh no, I don’t think so.” He sat up, looking down at Charlie where she was still sprawled between his legs. “You—you used made-up curse words. That’s how good I am. Real curse words don’t cut it.”
“Yeah, well—you started talking about pogo sticks somewhere in there,” Charlie shot back, sitting up too.
Dean pointed at her. “You started vibrating when I was going down on you.”
“You whimpered.” When Dean pulled back and blinked, Charlie nodded. “Like a little puppy.”
Dean snorted, rubbing a hand over his spinning head. “Okay, uh... fair’s fair, it’s a draw. I’ll buy you your dracowhasis and you buy me my booze.”
Charlie beamed at him. “Deal.”
“Seventy goddamn dollars?” Dean hissed.
Charlie pursed her lips, eyes darting around the game shop and wondering if anyone had heard. Dean was holding a hardcover book with an illustration of a red dragon on the front.
“For a new one, yeah,” she replied softly.
“Damn...” Dean flipped the book open, and his eyebrows rose. “That’s, uh... that actually looks kinda cool.”
“I know!” Charlie’s giddy smile faltered suddenly. “They’re, uh... not real, right? Dragons?”
“Well... not acid-spitting ones,” Dean assured her, pointing to the image he was looking at.
“I’ll pretend that’s comforting.” Charlie sighed. “You can buy me a used one if you like, that’s probably only twenty dollars. But...” She stared at the ceiling, pursing her lips innocently. “Iiiiiiif you buy me a new one, I’ll spend the same amount of money on your whiskey.”
Dean’s head snapped up and the book snapped shut. “Well, come on, let’s check out.”
“You know, if you think DnD is cool, I could explain it to you,” Charlie offered hopefully as they walked through the store to the desk.
Dean huffed. “God, I’m gonna need some good alcohol for that.”