A Wager Too Far

Story Info
Jeremy learns that he shouldn't make bets when he's drunk.
10k words
3.81
71.2k
112
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
nixnixxie
nixnixxie
117 Followers

As I came into the kitchen, I couldn't help but admire the pale curves of my girlfriend's shoulders. She stood at the fridge, side-eying the whiteboard-calendar stuck to the front of it as she took a long pull from her beer. Between the shape of her shoulder blade and the thin straps of her tank top dimpling her skin, I was immediately overcome by the need to feel her skin against mine.

I wrapped my arms around her midsection, nestling my chin between her neck and her collarbone.

"Mmm!" she said, putting a hand up and against the side of my face as she finished her sip. "Hey, Scoosh."

"Hey, Boosh," I said, completing our paired nickname for each other. She giggled as I nuzzled at her cheek. The faint scent of vanilla coming off of her, coupled with whatever natural pheromones she carried everywhere almost made me moan.

Instead, I growled, and she laughed, and I pulled my hands off of her stomach to squeeze the curves of her hips.

"I wish he wasn't coming tonight," I whined.

"Oh come on, you know that's not true," she said, taking another sip of her beer.

"The fuck it's not," I muttered.

Sure, I loved hanging out with my best friend, and I know he and I would have a ton of fun getting drunk and playing fighting games on my console. But seeing Jackie in her tank top, drinking her drink, finally relaxing after what I knew had been a stressful week for her...well, I really didn't want to spend time with anyone else.

My hands slid up her sides, cupping the pair of heavy girls her tank top had to fight to keep in place. She let out a small sigh of contentment, but immediately protested when my thumbs and forefingers found her slightly hardened nipples and gave them a pinch.

"Mmm! Jeremy!" she said, turning around, her brown eyes open wide. "He's going to be here any minute!"

"Yeah," I said, "exactly." I nodded towards her left breast first. Then her right. "Don't you think you should put on a bra? Or are you trying to give Deepak a show?"

I was...half-kidding. Joking in my delivery, at least. I'll be honest, Deepak was a good-looking guy...but even if he wasn't, I felt weird about the idea of my best friend being able to eye-suckle my girlfriend's nipples the whole night.

"Why," she said coyly, "are you afraid he might catch a peek?"

She hooked her thumb under one of the straps of her tank top and pulled forward, as if she were about to free her breast from its cloth confinement. Now it was my turn to have wide eyes, but it came to nothing as she let the strap snap back into place.

"Maybe Ishould give him a bit of a show," she teased. "Maybe if I can distract him enough, you might have a chance to beat him this week."

"Oh yeah?" I said, nodding emphatically at her. "You think I need help to beat him? Do you?"

"You need all the help you can get," she replied, taking another sip of her beer. I reached out and tickled her sides, causing her to almost spit out her drink.

"Stop! Jeremy, stoooop," she said as she pulled away from me, half-laughing and half-annoyed.

"I can't stop," I said. "Not with those massive melons staring me in the face."

Jackie crossed her arms, then realized that only gave me more cleavage to ogle.

Rolling her eyes, she put her beer down on the counter.

"I will go and put on a bra," she said, pretending to be more annoyed than she was. "Although half of this apartment is mine, and I don't feel like I should have to dress up in my own place."

"Well, since it's half-yours, then just put half of your bra on," I said. "Just one cup. There you go. Territory established."

She nodded with a big fake grin and gave me the finger, then headed off towards the stairs to the bedroom. But before she could even leave the kitchen, an annoying electronic tune filled the air. Jackie paused and slid her phone free from the waistline of her thin pajama pants.

"Aww, damn it," she said.

"What?"

"Shit..."

I watched her expectantly. "Sister?"

"Yeah," she said. "I gotta take this." She put the phone to her ear as her other hand ran through her shortish, punkish brown hair.

"Heyyy, Natalie," she said. "What's up?"

The shock on her face was fake, but the tone of her voice was real. "He broke up with you? Nooo..."

I shook my head, then went to the fridge to get myself a beer. Behind me, Jackie started pouring out the string of sympathetic phrases I'd heard her repeat to her sister so often over the years. I turned around to mouth something hilariously rude to her, but she was already disappearing out the sliding screen door leading to the back porch. I shrugged, then made my way through the kitchen to the living room to turn on the television.

I'd hoped to get in a few practice rounds ofCarnage Dojo before Deepak arrived. But just as I sat down, controller in my hand, the doorbell rang.

"Ah shit," I said, then got up and went to answer it.

"Hey hey, Jeremy," said Deepak from the mat outside.

"Hey man, come on in," I told him. I stepped back and held the door open. He crossed the threshold and we bro-hugged briefly. When he pulled away, he held up the plastic grocery bag he'd brought with him.

"Chips and dip," he said. "Should I set it up out here?"

"Yeah, boy," I told him, stretching out the syllables. "You know where everything is. Grab yourself a beer, too."

He left the bag in the living room with me, then stepped through to the kitchen as I started upCarnage Dojo. I heard him rummaging around in the cupboards, then opening the fridge.

"Jackie on the phone?" he asked. I heard the hiss of a beer being opened, followed by the sound of a bottlecap pinging in the stainless steel basin of the sink.

"Yeah," I said. "Natalie. Boy problems."

"You know I hit that, right?" he said, coming back into the room with a big bowl for the tortilla chips and a smaller one for the salsa.

"Dude, do not even joke," I told him. I tore open the chips and poured them into the bowl as he took a long draw from his beer.

"I'm serious," he said, picking up the other controller from its place on the ottoman.

"Dude, that would be the shitstorm of the fuckin' century," I told him, pouring out the salsa and dipping the first chip into it. "Please, tell me you're fucking joking."

"No, I'm serious, man. I-" his face broke out into his signature, pearly-white, shit-eating grin. "Ah shit, I couldn't keep a straight face. Of course I didn't fuck Natalie, dude. I wouldn't do that to you. Or Jackie."

He took another big drink from his beer. "Or myself. Shit."

I laughed, but inside I still wondered. He and Natalie had only met once, at a housewarming barbecue Jackie and I had thrown the previous summer. Deepak had played it pretty cool, but Natalie had been all over him. The only reason I knew they didn't have sex that night is that Natalie ended up drinking way too much and passed out in our tub.

I eyed Deepak suspiciously as he watched the intro sequence toCarnage Dojo, bopping his head to the beat. Just because they didn't hook up that night, however, didn't mean that they couldn't have hooked up later.

Loading up another chip with salsa, I decided that it hadn't happened. Deepak was almost six-four, and he stayed pretty damn fit for the pickup basketball games he played a few times a week at the gym. On top of it, he was making bank as a software engineer, and in the words of just a few too many of Jackie's friends, he was "fucking hot".

But to me, he was just Deepak. The first friend I had made after college, at my first job actually, both of us junior developers from competing schools in the same state. And even though we pretty quickly moved on from that shit show of a work environment, we had a ton of hobbies and interests in common, and pretty similar senses of humor, and we had stayed in touch.

"So," he said, putting his beer down and flexing his fingers on the controller, "you ready to lose?"

"Psh, you fucking wish," I replied. And with that, our monthly fighting game session began.

We were about an hour or so in -- and with a win ratio that slightly favored yours truly -- before Jackie joined us in the living room.

"Hey, Deepak," she said, briefly stepping in front of me to get to her favorite spot on the couch. I swore and leaned around her just in time for my character to catch a wicked combo and for Deepak to take the win.

He started laughing while I shot daggers at my girlfriend.

"Oh shit," she said, "was that because of me?"

"Hell no," Deepak replied. "I had your boy here on the ropes the whole match." He finished what was his second beer as I grumpily flicked through the characters, deciding who to fight with next.

"What's up Jackie," he said, tossing her a nod and finally returning her greeting.

"How's it going," she asked.

"Alright. How's Natalie?"

Before Jackie could answer, I cut in. "Deepak said he fucked her."

"What?!" Jackie said, at the same time as Deepak shouted it was a joke.

"Yeah, no shit it's a joke," Jackie said. "Otherwise she would have called me right after. Probably as soon as you got rid of the condom."

"Psh, girl, you know I don't wear condoms," Deepak said. I felt a flush creep up my neck. I really felt uncomfortable whenever he said shit like that around Jackie. But it was pretty rare, and I know he didn't mean anything by it, and before I could think of something else to say, I felt Jackie lean against me.

"Hey," she said, "I'm sorry for making you lose."

"Nah, it's okay," I said. "I was having a bad round anyway." I looked down at her, and my eyes naturally went to the depths of her cleavage. Just then, I realized that she'd never made her way to the bedroom to put a bra on...and her nipples wereobviously way harder than they had been when she and I were in the kitchen earlier.

I looked at her, shocked, but she just put a finger against her lips and nodded towards Deepak, who was on the loveseat perpendicular to the couch with his eyes glued to the screen.

"Who'sthat?" she said as he picked his character.

"Selbek," I replied as more blood rushed to my cheeks.

"Destroyer of men," Deepak growled, imitating the game's announcer.

"She's kinda hot," Jackie said.

"She kinda is," Deepak agreed.

I made my selection. "Yeah, well, we'll see how hot she is after I'm done with her..."

We played for another hour or so, with me and Deepak duking it out while Jackie yelled encouragement from the sidelines. The ratio of wins was going more and more my way the longer we played -- gun to my head, Deepak was probably a little bit better at the game than I was. But I was way better playing under the influence than he was, and we were about to start on a fourth beer.

"Ugh," Deepak groaned after a close loss. He put the heels of his palms against his eyes. "I need some motivation. Some motivation tobring it." He pounded his chest, then pointed at me.

"Okay," he said. "Five bucks a game. Let's go."

"Really?" I slurred slightly. "You really want to lose money on this?"

"I'm not losing shit," Deepak said. He nodded towards the character selection screen. "Come on. Pick your guy."

I gave Jackie a look. "You okay with this?" I asked. "I mean, you don't even like me putting money down on basketball games."

"Yeah, 'causeyou aren't playing in those games," she said. "You've got no control over it." She nodded towards the screen. "At least here you havesome control. Plus, it's only five bucks, and you guys are probably going to break even anyway, so..."

"Shit. Alright," I said, selecting one of my mid-tier fighters to start.

And we did break even...for a few rounds. But then I found myself fifteen bucks down...and then twenty-five...and then fifty. All of them close losses, some where I absolutely dominated him in the first or second round, only for Deepak to clinch the win by a few slivers of health at the end, or by time.

"Fuck!" I said after the last loss, tossing my controller onto the ottoman. "God damn. When did you figure out how to go all drunken boxing with this shit?"

Deepak laughed loudly. On the screen, his goofball character was singing some sort of Japanese nursery rhyme. My friend started singing and clapping along.

Next to me, Jackie was laughing. I glared at her.

"Can't you like fuckin'...distract him or something?" I said to her.

"Distract him? How?"

"Flash me those nips," Deepak said, finishing up his beer. I turned beet red while Jackie squeaked and crossed her arms over her chest.

"Dude, what the fuck?!" I yelled.

"She's the one who didn't wear a bra!" he replied indignantly. "I'm only human. Jesus."

I glared at him.

"It's a compliment!" he said to me. He nodded towards my girlfriend. "Tell him, Jackie."

I looked at Jackie. "You're a pig," she said to him, clearly suppressing a smile, and clearly notthat offended.

"Really?" I said to her quietly. "Really?"

She shrugged. "You're always telling me how great they are," she said. "But you're my boyfriend. That's your job."

I pointed to Deepak, who was obnoxiously switching through all of the characters on the select screen as fast as he could. "So what, that's validating for you?"

She looked up at me with her big brown eyes wide, pushing her shoulders forward to enhance her cleavage even further.

"Uh huh," she said in a babyish voice, and suddenly I had arousal wrestling with jealousy for my attention. She leaned up against me.

"I'll let you suck on them later if you stop being mad," she said in a singsong voice.

"Jesus, Jackie..."

"Take the deal, dude," Deepak said. "I know I would."

"You stay the fuck out of this," I growled at him, picking up my controller once more.

"And you..." I started on Jackie. She purred and leaned against me, and I felt my cock stiffen inside of my jeans.

"Yeah?" she said.

"You just...behave yourself," I told her. I selected my character. "Let's go."

I fought pretty decently. I won a few matches outright, 2-0. But the lowest I got my debt to Deepak was thirty-five dollars, and after some more back and forth I had a series of losses that put me a hundred bucks in the hole.

"Yep," I said, losing a difficult to swallow round, putting my controller down on the ottoman. "I'm out."

"What?" Deepak said at the same time Jackie said, "No!"

I turned to my girlfriend. "What, you like seeing me lose my money?"

"No, I like seeing you sweat a little," she replied, poking at my stomach, which had gotten a little soft over the last year or so.

I glared at her. "Not from losing," she said, all coy-like. "From trying. Your eyebrows get all...intense...and your eyes go dark."

She ran a hand through her hair. I didn't have to look over at Deepak to know that he was taking in the line of her arm as it transitioned into armpit and then the side of her raised breast, the heavy curve of it peeking out of the armhole of the tank top. But I was getting an eyeful too, and I wasn't going to tear myself away from the sight just so I could tell my best friend to fuck off again.

"It's all...hunter-killer," Jackie said. "It's sexy."

"Yeah, Jeremy," Deepak said mockingly. "It's sexy."

"Aww fuck off, both of you," I said. "I'm done."

Deepak pointed at the television. "You almost won that last one!"

"Yeah, Scooshy," Jackie said, pulling out the nicknames and the baby talk some more as she squished her chest up against my arm. "You almost won that one."

I closed my eyes. I had to. My cock was fighting hard against my jeans now, and I was having real difficulty squaring that away with how annoyed I was. There was nothing more I wanted to do in that moment than take Jackie upstairs and hate-fuck her for a bit.

Just then, another image popped into my head. Jackie, on her back, on the ottoman, her big tits spilling out over the top of her tank top and bouncing back and forth, her head tilted backwards so she could stare Deepak in the eyes as I fucked her.

I shook my head hard and pinched the bridge of my nose.Where the fuck did that come from, I wondered. Exhibitionism wasnot one of my kinks. Although, to be honest, I suspected that it might have been one of Jackie's. I'd seen her flash people a small handful of times before she and I started dating...and although she never did anything like that when we were together, I sometimes wondered if she still had the urge to show off for others.

"Come on," Deepak said. "Double or nothing."

I groaned.

"Double or nothing!" he said. "I'll even let you pick my character." He held up a hand. "Mid-tier. No trash."

I thought about it.

"Come on," Deepak said.

"Come on," Jackie echoed, then followed it up with some fake-anime speak. "You can do this, boyfriend! Try your best! Hyah!"

"Yeah, boyfriend!" Deepak said. "Hyah!"

"Fine, fucking fine!" I said. "You both suck, by the way."

I picked Deepak's character for him -- one of his mid-tiers, at his request. Then I picked mine -- one of my stronger ones.

And after a really intense match, I found myself down two hundred bucks.

"Fuck!" I said. I took a sip of my beer, but it was empty, which made me even angrier. "Fuck. How did I keep missing those counters?"

"You're drunnnnnk," Deepak said.

"No, don't be drunk!" Jackie said. She hadn't had as much as me or Deepak, but she was still tipsy. "I wanna ride that pogo stick tonight. But you can't get it up if you're drunnnnk."

"Whiskey dick!" Deepak bro-shouted, finishing his beer.

"I don't fucking get fucking...whiskey dick," I said. I poked Jackie in the boob. "You quit fucking with me."

I pointed to Deepak. "And you. Fucking saddle up. Rematch, double or nothing."

Five minutes later, I owed him four hundred.

"Shit!" I said. "Shit, fuck, cockgobbling...Goddamn!"

"Okay, evenI admit that was some bullshit," Deepak replied. "You definitely blocked those."

"Fuuuuck," I swore, putting my head in my hands. I felt something squish against my knuckles.

"Poor Scooshy," Jackie said, pressing her breast into me. "Here. Squeeze one. It'll make you feel better."

"You're drunk," I told her, drunkenly. She giggled.

"Squeeze that titty!" Deepak yelled over to me. I gave him the finger. He laughed and nodded towards the screen. "Again. Double or nothing."

"Hang on," I said, getting up from the couch and making my way into the kitchen.

Deepak started catcalling me from the living room. "Oh no, oh no," he said. "Big man Jeremy's gonna sober up for this round. Gonna pull out all the stops, gonna bust out his secret weapon."

I stepped into his view via the kitchen cut out, extending a middle finger to him the whole time as I downed a gigantic glass of ice water. I belched, then slammed the cup down on the counter. Roaring dramatically while beating my chest, I came back to the couch ready to battle.

And won.

"Ohfuck yeah, dude!" I said. "Eat it! I owe you fuckingnothing!"

"Yayyy Scoosh," Jackie cheered, bouncing up and down on the couch like a little kid. Playfully, I turned her towards me, buried my face in her chest, and did a victory motorboat.

"Not fair, not fair," Deepak said from his spot on the love seat. He pointed at my girlfriend's rack. "She's got those things out deliberately to distract me! I want a rematch!"

"No fucking way, dude," I said. "You're a bad friend and a pervert. You don't get a fuckin' redo!"

"Yeah," Jackie hiccupped. "Pervert."

Deepak stewed, biting his lower lip. "Redo."

"Hell no."

He nodded, his eyes narrowing the way it did whenever he got stuck on a particularly annoying programming problem, or whenever his pick-up team really needed a win. I should have paid attention to that. I should have realized that just as I took a moment to down my ice water -- which really was my way ofbringing it-- that he was about ready to put everything into his next match.

nixnixxie
nixnixxie
117 Followers