Chapter 5

I Dare You

Lauren Emily
8 mins read
Published over 1 year ago


Part FIVE: Take a Chance on Me

Jules awakens to her phone buzzing and her roommate moaning.

“Oh god,” she grunts before she pounds on the wall and yells, “Make her come quieter!”

“No can do!” Liam calls back. 

Blearily, Jules reaches for her phone and sees Jack’s text. 


“So what do you think?” Jules asks Evie, perching on the couch Liam fixed – again – before leaving for work.

“I’ll trade you,” Evie says, handing Jules her phone and reaching for the unicorn-shaped coffee mug. Once she takes a sip, Evie shrugs. “I mean, I dare you to take a chance on me? Seems pretty obvious on Jack’s part.”

“That’s what I was afraid of.” Jules gulps from her own mug, then props her feet in Evie’s lap.

“Is this something you want?” Evie asks, and all it takes is the word 'want' for Jules to flash back to two nights ago with Cici and Tom:

Jack giving her the longest, strongest orgasms of her life, swirling his tongue around her clit, curling those magic fingers inside her and using that beautiful cock to tease her, push her to the very edge, making Jules absolutely crazy, then taking her back, soothing her before bringing her there again, this time so over the edge that she couldn’t stop coming and coming and coming…

“He has a six-pack, Evie,” Jules blurts out.

Evie suppresses a grin. “Hot, but that’s not what I asked.”

Jules sighs. “I don’t know what I want. The gorgeous bartender I’ve been crushing on finally admits his feelings. This is my happy ending, right?”

“According to a Hallmark movie,” Evie retorts.

“Only with group sex.”

“Seriously,” Evie says, wrapping her hands around the unicorn, “I think we make our own happy endings.” She smirks. “Pun intended.”

Jules snorts. Setting her mug on the floor, she says, “I mean, a week ago I would have been all over this. And that was before I knew how fucking amazing he is in bed.”

“And now?” Evie takes a delicate sip from her mug.

“I realized…” Jules takes a deep breath. “I’ve had the best sex of my life since I started this dare thing. And for once, I’m not so desperate not to be single again that I’ll glom onto the first guy who’s nice to me. For me, good sex and relationships have always been two separate states of mind, you know?”

Evie nods. “You can have the best orgasms of your life with a boyfriend though.”

“So I hear. Through the wall.

Evie blushes. “I’m so sorry. Liam brought over this paddle and it turns out I was very into it and–” She laughs as Jules hums loudly while plugging her fingers in her ears. “Point taken. I mean, maybe you should stay single, see what’s out there.”

Jules looks down at her pajama pants. “But what if I lose him, Evie?”

Evie hands Jules her coffee mug, pretty face sympathetic. “That’s the risk you’d have to take.” Her Disney princess eyes go wide. “Speaking of risks, by the way…”

“You’re not pregnant, are you?”

“NO! God!” Evie crosses herself, then hesitates. “You haven’t found a subletter yet, right?”

“And I leave in two weeks,” Jules says, a wave of guilt washing over her. “I’ll put an ad on Craigslist today, promise.”

Evie’s expression is sheepish. “How would you feel if the subletter was Liam?”

Evie could drive a truck through Jules’ open mouth. “It’s been like a month!” Jules yells.

Evie bites her lip. “I knooooow, but his lease is up, and ugh, screw it, you know it’s not about the lease…”

Jules knows. For Evie and Liam, 'it' goes above and beyond their wall-penetrating, couch-breaking sex. Hell, she’d known the second she walked in on them in the kitchen. She’d talked Evie into trying a relationship. Clearly, Jules had created a monster.

A love monster, who smiled all the time and has a sweet, funny guy who makes her happy. 

“Oh goddammit,” Jules says. “Come here.” She lifts her feet off Evie’s lap and they squish together in what they call a “two-boober hug.”

Jules smooths Evie’s hair. “I love you, roomie. And I like that man of yours, even if you’re way too loud in the mornings.”

Evie squeezes Jules again. “I love you too! If it ends up working out you’ll totally get your room back…”

“Uh, you two are not fucking in my bed,” Jules says. “Liam practically lives here anyway, so he might as well make it cheaper for the three of us.” She musses Evie’s hair. “Because it will work out. I know.”

Evie’s smile could power the whole city block, but Jules feels sad. She knows this thing with Liam is real, but now the days of Jules and Evie, two roommates against the world, are over. And Jules can’t help but wonder, do I want this too? 

“I have an idea!” Evie squeals.

“For what? A St. Andrew’s cross in your new shared bedroom?”

“What’s that? Anyway,” Evie says, “I’m going to dare you!”

Jules rolls her eyes. “Oh god. What am I in for now?”

Evie’s eyes sparkle. “For once, you keep me awake.”

“Oh god!” Jules pants as Quinn tongues her throbbing clit. 

She’s never been much for Tinder, but clearly, she just hasn’t been doing it right. Quinn is sweet, with thick blond hair and a really nice cock, and best of all, he brought her donuts. At 11 p.m. Because she asked him to.

He lifts his head from between her legs. “Like it?”

“Oh yeah,” Jules says, trying to catch her breath.

“Got a condom?”

“In the drawer.” He gets up and Jules turns over on her stomach, looking over her shoulder at his lovely bare ass. “Hey,” she says once he’s suited up. “How about like this?”

“Mmmm,” Quinn says, and Jules scrambles up to her knees. Before she knows it, he’s sliding into her, gently thrusting at first, then with increasing pressure. She feels her pussy squeeze around him, and relishes this near-anonymous encounter where she’s safe in her own bed with roommates just a knock on the wall away.

Roommates. Make it louder.

“Oh yes,” Jules moans as her pussy grips his cock tighter and tighter. Balancing on one arm, she reaches down to finger her clit, flicking then rubbing the bud, feeling herself get wetter and hearing herself moan louder as she fucks against his cock. Behind her Quinn grunts, clearly getting into the vocal action, and she feels that pleasing pressure in her lower back, her tits heavy and jiggling. 

“Harder!” Jules shrieks, touching her nipples, her clit, and as he slaps her ass and she comes, her voice soars.

“Hey stranger,” Liam says.

“Do you want the bathroom first?” Jules asks. Quinn is gone (she sent two donuts with him as a reward) and she’s munching on a glazed old-fashioned in her tank top and boxers.

Liam shrugs, rubs his eyes. “You can take it.” At this late hour, his voice is about an octave lower. “Good job in there.”

Jules laughs. “Did Evie appreciate my theatrics?”

Liam grins. “She fell asleep about two minutes in.” He leans against the wall of the hallway. “By the way, are you okay with my moving here? Evie said she talked to you but I wanted to check in too.”

“I extend the donut of friendship,” Jules says, her tone authoritative, breaking it in two pieces and holding one out to him. They both laugh. “I’m cool, Liam. Make Evie happy and that makes me happy.”

“Good,” Liam says, taking a bite of donut. “Guy brought you Stan’s Donuts. I’m impressed.”

“Only the best from my booty calls.” 

“Heard about the Jack thing. The last dare.” Liam looks down at his bare feet, wiggles his toes. “Have you talked to my man-crush about it?”

Jules smirks, then buys time by finishing her donut. Once she’s swallowed the last crumb, she shrugs. “I feel like words don’t always work when sex is involved.”

“Hm,” Liam says. “You might be surprised.”

“Says the guy who’s moving in with his one-night stand.”

Liam smirks. “Fair. But hey, it hasn’t all been breaking couches. When Evie and I got caught at work –“

“First or second time?”

“Second. After we quit, we went to Starbucks and hashed it out. My hesitations, hers. We figured if we were going to try dating, we wanted everything on the table. And, like, it’s not going to prevent every single problem, but I think it’s working so far.”

Jules considers this. How despite all the fun she’s had – and she has had a blast slutting around – she can’t stop thinking about the bartender who right about now is refilling garnishes, collecting tips and slinging drinks. 

Talk to him. Is it really that simple? 

“While you think, I gotta pee.” Liam gestures to the bathroom. “Do you mind?”

Jules shakes her head. “All yours. And Liam?” He pauses, illuminated by the bathroom light. “Thanks.”

He smiles and closes the door.

And now Jules knows what to do.

“There she is,” Jack says. 

Half an hour, the world’s fastest shower and one Lyft ride later, Jules is walking into the bar right before closing.

Her eyes meet Jack’s, and despite the crowd of drinkers, Jules feels like the only one in the room.

“Hi,” she says softly, taking a seat. As if by magic, a glass appears in front of her. She takes a sip – watermelon vodka soda. Of course, he remembered.

“Glad you’re alive,” Jack says, throwing the bar rag over his shoulder. “I wanted to check in with you after Cici and Tom, and then–”

“That last dare,” Jules says, taking another drink. She swallows hard. She can recite dialogue with the best of them, but improvisation has never been her strong point.

The Cure’s “Just Like Heaven” plays. One of Jules’ favorites. 

“I love this song,” Jack says. 

“I like you,” she blurts out.

For a moment, Jack doesn’t say anything. As Robert Smith croons, patrons file out. Jack leans his elbows on the bar, just like that first night, and grins.

“I like you too, Jules.”

She worries her heart will burst out of her chest.

The last guitar riff of the song evaporates into the air. Now that they’re alone, they can’t stop talking over each other.

“Oh god I’m so glad…”

“I realized once I started the dares that I was interested in you…”

“I’ve been interested in you all along too!”

“And we didn’t get together right away, why?”

At Jack’s last question, Jules gets serious. She concentrates on her empty glass as she proceeds to spill out the contents of her heart. “I mean, I’ve pretty much always been in a relationship, and they’ve never…” She pauses, racking her brain for the right word. “Fulfilled me.” 

Taking one last pull of her straw, she sets her glass down on the bar, now polished clean. “And I started having all this phenomenal sex because of you, and I don’t regret any of it, or anyone, but…” Her eyes meet Jack’s. “I could never stop thinking about you.”

Jack covers Jules’ hand with his own, looks deep into her eyes, and says, “I have a car.”

Jules bursts out laughing. “Oh, the magic words of long-distance relationships!” She claps a hand over her mouth. “Did I prematurely relationship?”

Jack laces his fingers through hers, setting every nerve in Jules’ body aflame. “I’m cool if you are,” he says, smiling. “I liked flirting with you, talking to you, from minute one. I’ve just had one too many bar hookups, so I thought the dare thing would be a fun way for us to stay in touch. And then…” He bent down and brushed his lips over her knuckles, and Jules had to grip the barstool with her other hand so she wouldn’t pass out right then and there. “I found out that you’re really amazing. And, I don’t know, maybe this won’t work, but, you know…” He squeezes her hand. “I’d like to try.”

Jules feels warm from the top of her head to the tips of her toes. “Me too,” she says. 

She’s also very turned on.

“So…” Jules raises an eyebrow at Jack. “Your place?”

“This is my studio,” Jack says, gesturing to the hardwood floors, the framed Queen posters and the shelves positively groaning with books.

Jules looks at Jack, and says what she’s been thinking the whole train ride:

“Can we get naked, like, right now?”

He grins, and her nipples ache. 

Their mouths meld together as their clothes fly off. Frantically kissing everywhere, Jules and Jack stumble into his warm bed. She’s so wet and ready, savoring his delicious body, his delectable mouth, but Jack has other ideas.

“Let me touch you,” he growls in her ear and her legs fall open as his fingers travel downward.

He starts by running his hand over her pussy, laughing softly and pushing her hips down when she tries to make him do more. “Patience, sexy grasshopper,” he says in her ear, and she giggles and shivers at that rumbling voice. She loves the fact that he can make her laugh in bed. Sliding in one finger, then a second, Jack takes his time, kissing her neck, gently biting her shoulder, his cock growing hard against her leg.

“Oh my god,” Jules sighs, as his fingers begin to work in and out of her wet pussy. She starts moving her hips and he adapts to her rhythm instinctively, their mouths finding one another for a hungry kiss.

His fingers push deeper, further inside her than Jules is used to. He meets her eyes, whispers “this okay?” and she nods, trusting him, intrigued at the fuller sensation. He kisses her nose and begins thrusting his fingers, and she squeezes her legs around his hand, wanting to feel everything all at once.

His eyes never leave hers, and Jules knows he’ll stop if she wants him to, but she doesn’t. As she grips him inside her, Jules is aware of a new feeling – hot, slightly uncomfortable, but on the edge the way she’s never felt before, and as he goes faster, she knows she’s on the brink of something new and fantastic and…

“Ohhhhh!” she screams, thrusting her hips as he fucks her with his fingers that’s my G spot oh fuck no man’s ever found it before. “Fuck, Jack, don’tstopdon’tstopdont’stop!” and when she feels the extra wetness as she comes harder and faster than she ever has in her life, she knows. 

“You made me squirt,” she whispers, as Jack gently withdraws his fingers, kissing her as her trembles cease, running his strong hands all over her body and nuzzling her neck.

Fully satisfied and sated, she strokes the side of Jack’s face. “Now thata happy ending.”

Jack kisses Jules’ palm and moves his body on top of hers. “Oh darlin’, we’re just getting started.”

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

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