I Dare You

Lauren Emily
8 mins read
Published over 1 year ago

Part One: The Stranger

“I can’t get laid to save my life.”

Jules punctuates this declaration with a dramatic glug of vodka.

“Sorry, what?” her roommate calls from across the table.

“SHE CAN’T GET LAID TO SAVE HER LIFE,” her roommate’s boyfriend hollers over the bad karaoke rendition of “Lodi.”

“I was hoping the music would screech to a halt and everyone would hear,” Evie says, grinning at Liam. 

“Don’t get me wrong,” Jules says. “I’m truly happy you two are banging –“

“Aw thanks, bestie!” Evie says, reaching for Liam’s hand.

“ – but what about meeeeee?” Jules whines. She looks at her friends for sympathy but they’re not listening, and one of Liam’s hands is no longer on the table... Oh god. At least they haven’t broken the couch again. This week.

“Do you want to sing?” Evie asks, pushing the binder of tunes toward Jules, her Disney princess eyes wide with genuine concern. She knows how much Jules loves an audience.

“‘No Scrubs’?” Jules asks, naming their favorite duet from college.

Evie nods. “You got it. I’ll put our names in if you get another round?” 

As Jules elbows her way through the Thursday-night crowd, she realizes what a nice bar this is. It’s divey but comfortable, the sharp smell of alcohol complementing the karaoke host’s tuneful rendition of “Crazy Little Thing Called Love.” This place is Liam’s favorite. It’s where he and Evie ran into each other and jump-started the one-night stand that became a relationship. Bellying up to the bar, Jules wonders whether she’ll have the same luck.

Maybe, if the bartender was doing his job instead of checking out that blonde’s ass over there…

“EXCUSE ME!” Jules says, and it’s then that the music screeches to a halt. She sometimes forgets how much her voice carries – all those years of acting lessons.

The bartender saunters toward her and Jules looks at the ceiling, frantically trying to remember what everyone was drinking. “Um, a whisky straight up, a whisky Coke with extra limes and… a watermelon vodka soda.” 

“I like a woman who knows what she wants.”

And then for the first time, she really looks at him.

As if that voice – smooth yet a little rough, like salted caramel – weren’t enough, he’s got hypnotic hazel eyes, and skin just shy of olive with a handful of freckles sprinkled across his perfect nose. His hair, dark brown and wavy, curls around his collar and pairs nicely with his scoundrel-esque grin. 

Jules remembers that Liam has mentioned his man-crush on this guy, and now she totally gets it.

“…though you could have been a skosh less demanding.”

Jules rolls her eyes. “You were staring at that blonde’s ass!”

“To be fair,” he says, grinning wider, “it’s a very nice ass.”

Jules snorts. “I’ll have to take your word for it.”

“I’m just giving you a hard time.” He extends his hand over the bar. “Jack.”

“Jules.” Is it just me or did he hold my hand slightly longer than necessary?

Down, girl. Guy’s probably a total player.

“I’ll get your drinks,” Jack says softly, and without another word, he’s turned around, giving her a view of his very nice ass.

Those eyes, deep and soulful, like they can see right into her, might explain what happens next: as soon as Jack reappears with three full glasses, Jules starts babbling.

“So I was just telling my friends, I can’t get laid to save my life. And I know they’re trying to understand, but they just officially got together – oh god, that’s them over there, making out. Anyway, normally I’m Relationship Girl, but there are two problems. One, I just broke up with somebody – boring story, well, he was boring – and two, I’m about to go out of town for an acting job. And even if I were in town this summer… I dunno. With every guy I’ve dated, the sex gets so dull so fast, and right now I just want to have fun, you know? Except not get murdered. Or break my couch.” She stops to take a breath.

Jack opens his mouth to say something, then reaches below him and pulls out…

A bottle of Jameson.

Jules is very disappointed.  Why was I hoping he’d pull something out of his pants? I must be hornier than I thought.

“On the house,” Jack says, pouring two shots. “Cheers.” They clink glasses and this time their fingers don’t touch. Damn.

Jules downs her shot. “Thank you,” she says. “I’m sorry, I’ve known you all of – what, three minutes? – and I’m bombarding you with the sordid details of my sex life.”

Jack shrugs. “Happens every night. But not everyone gets free Jamo.” There’s that grin again. “I do have some questions, though,” Jack says, resting his elbows on the bar. “Can you tell me more about the couch?”

Jules laughs. “Not important.”

“Cool. And you’re an actress?”

She stands up a little straighter. “I am.”

“Also cool.” She can tell he means it, which is more than she can say for her last five dates.

Jack takes a step back, studying her. Appraising. 

“Like what you see?” She strikes an exaggerated pose and flicks her tongue at him.

Jack laughs. “You’re funny.”

She wishes there weren’t a bar between them, but maybe that’s a good thing, because right now, Jules isn’t sure she can trust herself not to rip his clothes off. “Anyway,” Jack continues. “I have this crazy idea. Wanna hear it?”

“Let me guess: you’re going to fuck my problems away?” Gotta work on that filter, Jules.

To her surprise, Jack isn’t taken aback like most guys. Instead, he drops the ultimate bomb: 

“I have a girlfriend.”

“Of course you do,” Jules says.

“But what I’m thinking is, I can text you.”

Jules raises an eyebrow. “She gonna be okay with that?”

“Not that kind of texting,” Jack says, grabbing a bar rag. “More like…suggestions. To improve your current situation.”

She’s not following. “You’re going to sext me?”

Jack mops up a puddle of melted ice, never taking his eyes off Jules. “I was thinking dares. Like, I dare you to do… this thing. With someone.”

Dare. Even the word is sexy. “And if I’ve done the thing, with someone, before?” Jules asks.

Jack shrugs. “You tell me. I think of something else.”

“What if I don’t want to?”

“You say no.”

Now she’s feeling saucy. “What if they’re boring?”

He drops the bar rag and leans in. “Trust me, sweetheart.” He has very nice forearms. Jules’ knees buckle. “I’m very creative.”

What does she have to lose?

Jules takes a deep breath. “Give me your phone.” He hands it over and their fingers brush again. “When’s the first dare?” she asks, punching in her number and handing it back to him.

“Patience, grasshopper,” Jack says. Someone down the bar calls his name and with a wink, her sexual mentor is gone. 

Still not sure what just transpired, Jules gathers the glasses and turns around.

Suddenly, ice-cold liquid splashes down her front and she shrieks.

“Fuck, I’m sorry!” She hears a male voice, looks down at her top and realizes she’s now wearing her three drinks. Oh god, she forgot to pay Jack. 

“Here.” The same voice is back, and she sees its owner extending a wad of napkins to her. Jules sets the empty glasses on the bar and turns around.

Oh, hello.

He’s tall, with gorgeous dark eyes, smooth skin and a thatch of dark hair. Like John Cho’s slightly shorter but sexier brother.

“Thanks,” she manages to squeak.

“I’ll buy you another round,” he says, craning his neck. “As soon as the bartender gets back. I’m so sorry – I’m new to Chicago and apparently I’ve lost my coordination. Are you okay?”

 Totally, don’t worry about it,” Jules says, finally finding her voice. “I’ve waited tables since high school – you’re not the first person to spill on me.” But you’re by far the hottest.

 “I’m Ian.” 

“Jules. Where are you from, Ian?” Normally she doesn’t chat up strangers in bars, but knowing her number is in Jack’s phone makes her bold. 

“LA.” He has a low, calming voice, almost musical. “I’m doing a play at Steppenwolf.”

“Shut up!” Jules squeals as the vixen disappears and her inner theater geek takes over. 

Ian laughs. “Impressed?” He leans in, and she catches a whiff of Ivory soap.

Jules nods. “Very. I’ve never gotten past general auditions.”

“Are you working on anything?”

She lifts her chin. “I’m getting my Equity card this summer, at a repertory theater outside Cincinnati.”

Ian’s eyes light up. “The Red Barn?”

“That’s the one!”

“You’ll love it. Amazing people, really cool town with an incredible taco stand. It’s been two summers and I still dream about those tacos.” 

Her phone vibrates in her back pocket.

Jules vaguely remembers she’s supposed to get drinks. “Hold on a sex, I mean a sec?” she asks, and looks at the screen.


She swivels her head and sees Jack behind the bar.

I can’t do this, she mouths at him. (Also, does he always text in all caps?)

His response is as clear as if he’d murmured it in her ear: 

You can.

She thought she’d have some time before the first dare, dammit! 

And yet…

Jules has always been the wild friend, in all areas but one. For years, she’s settled for mediocre fumbling and minimal effort. Jules realizes that this is her defining sexual moment. From here on out, she can continue to resign herself to men who are boring in and out of bed… or push herself and find what she really wants. 

“Hey,” she says to Ian. “I’m going to dry off in the restroom.” Standing on her tiptoes, she whispers in his ear, “If I’m not out in two minutes, come find me.”

Without waiting for his reaction, Jules makes a beeline for the ladies'.

Instead of getting more paper towels, Jules grips the counter and looks in the mirror over the sink. “What the fuck am I doing?” she asks her reflection.

And then she hears Jack’s salted caramel voice in her head:

I dare you.

She hears a polite tap on the door, followed by broad shoulders and a handsome face. “Need any help?” Ian inquires.

She pulls him inside and he locks the door behind him.

Their first kiss is an electric symphony. His lips are soft, his tongue tasting of gin, playing with hers in a way that awakens her nipples and hardens her clit. If nothing else, Jules thinks, I’ll be touching myself to this memory for a long, long time.

With their mouths still locked, Ian guides Jules to press her back is against the wall. She sighs happily when he reaches under her denim skirt, pushing her panties aside and his fingers find her pussy.

“So wet,” he murmurs, his lips and tongue brushing her ear. She shivers as he slides one finger in, then another. Jules bites her lip hard so as not to come right now while his fingers slide in and out and his thumb strokes her clit. 

“Oh god,” Jules moans, and he laughs in her ear, gravelly and bothered. 

“Your pussy’s squeezing my fingers,” he whispers. Jules knows if they were in her bedroom she’d get them both naked and fuck him hard, but the fact that they’re fully clothed, in public, makes her even greedier for him.

Ian bites her neck, sending Jules over the edge. She moves her hips to meet his hand, catches his mouth and from there she grays out, her pussy contracting around his fingers and moaning loud as Ginuwine’s “Pony” reverberates just outside the door.

When she finally finishes, Jules slows her hips and Ian his fingers, her face flushed, a dreamy smile on his as he gently kisses her lips. “Good?” he whispers.

“So good,” she breathes, moving her hands down the front of his jeans. “Oh hello, big boy,” she says in his ear. Slowly she unzips his fly, bit by bit, teasing. She reaches into his plaid boxers and feels his thick, smooth cock, running her hand up and down the length.

“You’re killing me,” Ian groans.

She laughs. “That’s the idea, cowboy.”

She tightens her grip on his cock and begins to stroke, slowly at first, then increasing speed. “I like my cock in your hand,” he says, smiling at her. 

“You’re gonna like it even more in my mouth.” Jules tips her chin at the sink. “Lean up against that.” Ian and his hard cock are more than happy to do so.

Once he’s in position, Jules bends over at the waist, ass in the air like a naughty schoolgirl. She eases Ian’s pants and boxers down just enough so his cock springs forth, and catches a glimpse of herself in the mirror: lips swollen, eyes hungry. A far cry from the nervous girl from just a few minutes ago.

“Oh fuck,” Ian groans as Jules touches her lips to his cock. She’s never sure if she does blowjobs right, but maybe she’s been sucking off the wrong men because with Ian, her moves feel instinctive. Licking off the bead of pre-come while looking up at him, she then begins to tongue his shaft. As she braces herself on the side of the sink with one hand and cups his balls in the other, as she inhales deeply and takes all of him in her mouth.

Listening to him gasp and moan, bent over at the waist with her face between his legs, Jules feels a power she’s never before experienced. And when Ian rasps, “Oh shit Jules, here it comes,” she relishes giving him everything he wants and swallows down to the last drop.

“Next up to the stage is Jules and Evie!”

Jules pops up. “Our song!” She kisses Ian on the cheek, quickly readjusting her clothes as best she can. “I gotta go. Break a leg at Steppenwolf!”

“You’re amazing,” he whispers, as he zips up his pants and she unlocks the door, rushing out of the restroom.

“Sorry!” she says to Evie, who hands her a microphone as the opening bars of “No Scrubs” ring out.

“Where the hell were you?” Evie hisses, then takes a longer look at Jules. Mussed hair, wet lips, and visible bra strap... Her eyebrows shoot up after so many years of friendship, Evie can read Jules like a book. “I want details.”

“You’ll get them,” Jules whispers as Evie starts the song and Liam films them with his phone. Jules harmonizes on the chorus, face flushed, hair a total mess, and smile a mile wide. 

Across the bar, Jack catches her eye and grins.

Part two: The Great Outdoors

Lauren Emily lives (and loves) in Chicago, and is the author of the novel SATELLITE. Check her out at laurenemilywrites.com.

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