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The Girl Who Never Loses
The Girl Who Never Loses with Hailey
Hailey
Hailey

The Girl Who Never Loses

Holidays & tripsDominantMedium · 8 min

29 photos · 3 videos · 8 min read

Hailey spends the whole weekend teasing you and losing on purpose is not in her vocabulary. Then she dares a midnight swim and says exactly what she wants: both of you.

You've known Dev since college, so when he says lake trip, you say yes before he finishes the sentence. Jess and Marcus are the couple who finish each other's beers. Jess brings Hailey — "my friend from work, she's a lot" — and "a lot" turns out to be an understatement.

Hailey is a redhead with freckles across her nose and shoulders, and she has one setting: give shit. Within an hour of arriving she's beaten Marcus at cards twice, called Dev's tent "a condom for beginners," and looked you up and down like you're a menu item she hasn't decided on yet.

Every time you try to talk to her, she ignores you. Not rudely — strategically. Like she's saving you for something.

The hike up the ridge is hot and dusty and Hailey is at the front the whole time, not because she's fit — she is — but because she refuses to be behind anyone.

"Slow down," Jess pants.

"Walk faster," Hailey calls back, and when she turns around to grin at you she's walking backwards on a rocky trail like an idiot, like she's never once considered falling.

She does not fall. You're almost disappointed.

"Nice view," you say when she faces forward again.

"It is," she says. "I'm enjoying it too."

The lake in the afternoon. There's a rope swing hanging off a big pine, the old knotted kind, and Marcus goes first and belly-flops hard enough to make a sound like a slap.

Hailey laughs so long she has to sit down on the dock.

"Your turn," she tells you, eyes bright. "And if you say 'I'm just going to wade in,' I will push you off the dock. I've done it before. Ask Jess about the birthday."

You take the rope. You stick the landing. When you surface, Hailey is standing at the end of the dock with her arms crossed, sizing you up.

"Huh," she says. "Okay. You get one point."

"One point out of what?"

"We'll see."

She goes on the swing after you, and she's not graceful about it, she's aggressive — she runs, she yells something that might be a war cry, and she hits the water in a cannonball that soaks Dev where he stands smoking on the shore.

When she comes up she's laughing, hair plastered to her face, and she looks directly at you while she wrings it out.

"That's two points," she says. "I'm winning."

"You're the only one keeping score."

"Exactly why I'm winning."

Dinner is burnt sausages and Jess's famous "it's fine, just scrape that part off" pasta. Hailey sits across from you at the picnic table and eats like she's been starved for a week, no performance about it, which you find weirdly attractive.

You pass her the ketchup. Your fingers touch. She doesn't move her hand.

"Smooth," she says.

"I'm passing the ketchup."

"Sure you are." She takes it. Her eyes stay on you a beat too long, then she turns and destroys Marcus at cards a third time.

The campfire, the whiskey. The bottle goes around and around, and someone — Jess, the traitor — suggests truth or dare.

Marcus gets dared to serenade a tree. Dev admits he once cried at a dog food commercial. Then Jess turns the bottle and it points at Hailey.

"Truth," Hailey says, suspicious.

"Is it true," Jess says, grinning evilly, "that you think one of the guys on this trip is hot?"

Hailey takes a slow sip of whiskey. The fire pops.

"Two of them," she says. "Statistically I'd have to be blind otherwise."

Everyone hoots. You feel your ears go hot and hope the firelight covers it. Dev coughs into his fist. Hailey just looks pleased with herself, like she's set off a firework and is now watching where it lands.

“Two of them.”

Jess and Marcus call it a night — Jess is pulling Marcus toward the tent by two fingers in his belt loop, and nobody needs to see more of that.

"Get it, girl," Hailey calls after them. Then it's the three of you and the fire's dying down to orange coals and the lake is black glass with stars floating in it.

Hailey spins the bottle. It points at you.

"Dare," you say, because you're three whiskeys in and brave.

She smiles like she's been waiting for this all weekend.

"Midnight swim," she says. "All three of us. Right now. Skinny dipping."

Dev says, "What?" at the same time you do.

"Rules are rules," Hailey says, standing up and already pulling her shirt over her head. "Unless you're chicken."

She strips on the dock without a single hesitation — shirt, sports bra, shorts, everything, dropped in a pile like she does this every Tuesday. Firelight from the coals catches her: freckled shoulders, small pale breasts with pink nipples, a strip of red hair between her legs.

She stands there completely naked with her hands on her hips and looks at the two of you.

"Well?" she says. "You've seen tits before, right? It's a hot night. Let me know when you get to first base."

You and Dev look at each other. Some entire conversation happens in about one second. Then you both start undressing.

"That's what I thought," Hailey says, and dives in.

The water's cold and it doesn't matter. She surfaces between the two of you, close, wet hair slicked back, and now that the joking's over her voice drops low.

"Here's my truth," she says. "Since Jess made me almost say it. I've been thinking about this since the hike. Both of you. Tonight. And if either of you says no, that's fine, but say it now."

Dev looks at you again. You look at Hailey's mouth.

"Yes," you say.

"Fuck yes," Dev says.

"Good," she breathes, and grabs you both by the back of the neck. "Get me back to the dock. I don't want to drown. I want to enjoy this."

On the dock, on the pile of everyone's clothes, she pulls you down first. You kiss her and she kisses back hungry, all tongue and teeth, her hand already finding your cock and wrapping around it, stroking you slow.

"Nice," she murmurs against your mouth. "I hoped."

Dev kisses her neck and she shudders and laughs at herself for shuddering. "Okay, that's — okay. Someone get a finger in me before I lose my mind."

“Nice. I hoped.”

You slide your hand down her wet stomach and between her legs. She's hot even after the lake, slippery, and when you push two fingers into her pussy she groans and her grip on your cock goes tight.

"There," she says. "Right there. Don't you dare be gentle."

“There. Right there.”

She pushes you flat on your back and sinks down onto your cock in one long motion, her head dropping back, a low "fuuuck" coming out of her. She rides you slow at first, getting the angle, then faster, water dripping off her onto your chest.

"Dev," she says, voice wrecked. "Mouth. Now."

He gets behind her, tongue on her while she fucks you, and she stops being witty for the first time all weekend. Just words falling out — "yes, yes, like that, don't stop, both of you, god —" and her pussy clamps down on you when she comes the first time, hard, thighs shaking against your hips.

"Okay," she pants, grinning down at you, hair stuck to her face. "Nobody's ever gotten three points before. You're both doing great."

“Yes, yes, like that.”

She wants Dev next, and she wants it from behind, and she wants you in her mouth while he does it. She arranges everyone like a coach setting a lineup, and then she stops being a coach and gets loud.

You watch her — red hair, freckled back, her lips stretched around your cock, her hand working what her mouth can't reach — while Dev pounds into her and she takes it, gives it back, pushes her hips into every thrust.

“Harder, Dev.”

She pulls off you just enough to talk, because of course she does.

"You like watching," she says, breathless. "You've been watching me all weekend, you fucking liar. I saw you. Now watch this."

And she swallows you back down.

“You like watching.”

Dev finishes first, groaning, his hands tight on her hips, and the feel of him through her — the rhythm, her moaning around your cock — drags you right to the edge.

"Hailey —"

She pulls off, strokes you fast with her wet hand, looks you dead in the eye.

"Do it," she says. "Come on me. I never lose, and I want to win this too."

You come across her chest, her chin tilted up, her still stroking you until you're done and shaking. She wipes her mouth with the back of her hand and looks like a queen surveying conquered territory.

"Three points each," she announces to the night sky. "Tie game. I'll allow it."

“Do it. Come on me.”

“Come on. Give it to me.”

You end up tangled on the pile of clothes, three bodies, the coals glowing and the stars absolutely showing off. Dev's already half asleep, which is a Dev thing to do.

Hailey's head is on your shoulder, her fingers tracing lazy circles on your chest.

"For the record," she says, "I decided on the hike. Both of you. I just like making people work for it."

"I had no idea," you lie.

"You're a terrible liar and I find it charming." She tilts her head up and kisses the corner of your jaw. "We have two more nights. And I keep score."

In the morning she beats everyone at cards again, wearing your hoodie and nothing else, and nobody dares say a word about it. Marcus makes pancakes. Dev high-fives you behind the cooler where no one can see.

Hailey catches your eye across the picnic table and slowly, deliberately, mouths: *tie game.*

You have two more nights. She keeps score. And you'd bet everything she's already planning the rematch.

“So are you going to sit there, or are you going to come talk to me? I don't bite unless asked nicely. Tell me what you'd do to earn your fourth point.”

The end of “The Girl Who Never Loses”

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