A Girlfriend's Dare: Ch. 03

Andrew doesn’t know how long he spends in the chemical afterglow of defeat, heart battering away inside the terry-cloth cocoon Steph’s left him in. The room is quieter than it’s been in years, as if even the city has put down its arms and is just waiting to see what happens next. He sits at the edge of his unmade bed, robe cinched to the first notch, and wonders whether this is what rock bottom is supposed to look like: two bruises from a bikini string, the sticky aftertaste of shame, and Steph on the other side of the apartment, probably texting his humiliation to three group chats at once.

He doesn’t hear her approach until she’s already in the doorway, hip braced against the jamb. She’s wiped off the wine lipstick but replaced it with something even redder, like she wanted her mouth to be a warning sign.

“Sleeping beauty,” she says, “you planning on coming out, or should I bring your dinner to the dungeon?”

He looks up, bleary. “Is this the aftercare portion of the evening?”

Steph snorts. “Please. You think you’re the first boy I’ve made parade around in women’s swimwear? Come on, get your blood sugar up. You look like a fainting goat.”

She leaves before he can reply, trailing the scent of bergamot and high-caliber mischief. Andrew lurches after her, feeling both hollow and hyper-present, every inch of exposed skin tuned to the possibility of the next embarrassment. The living room is unchanged except for the addition of a paper bag on the coffee table—Chinese takeout, the good place, judging by the grease halo blooming through the bottom. Steph is already eating straight from the carton, using chopsticks with a precision that makes Andrew feel like a caveman.

He sits across from her, careful to keep his robe closed. She watches him for a minute, eyes tracking his hands, the movement of his jaw, the slow build of his composure.

“Do you want to talk about it?” she asks, voice unexpectedly gentle.

He stabs at the food. “I’d prefer to repress it until it metastasizes into something treatable with pharmaceuticals.”

Steph laughs, a sharp, clean sound. “That’s my boy.”

They eat in companionable silence until the lo mein is gone and the only thing left is a fortune cookie. She cracks it open, reads the slip, then slides it across the table.

It reads: “An unexpected journey will test your character.”

Steph raises an eyebrow. “Very on-brand.”

Andrew’s phone vibrates on the table. He glances at the screen—just a news alert, nothing urgent—and sets it back down.

Steph leans in, elbows on the wood. “You’re not getting off that easy,” she says, and something in her tone makes the back of his neck prick.

He doesn’t answer, but she’s not waiting for consent.

“Here’s the thing,” she says. “You handled tonight pretty well. You’re resilient, which I appreciate. But I need to know if you’re willing to push this a little further.”

He swallows, throat gone sandpaper-dry. “Define ‘further.’”

Steph’s eyes flick to the window, then back to him. “Do you know where the building mailbox is?”

He nods, slow. “Bottom of the stairs. Next to the fire exit.”

“Perfect,” she says. “I want you to walk down there, in the bikini. No robe. Get the mail. Bring it back.”

He gapes. “You’re joking.”

“Do I look like I’m joking?” Her face is placid as a winter pond, but there’s a glint behind it that says she’s already counted the steps, already weighed the odds of neighborly interference.

“It’s midnight,” Andrew says, as if the hour might be a mitigating factor.

“Prime time,” she replies. “Fewer witnesses, but the ones who *are* up are guaranteed to be interesting.”

He slumps. “This is—you know this is borderline criminal, right?”

Steph smirks. “That’s what makes it hot.”

He could argue, but she’s not wrong. The idea is so unhinged it’s almost virtuous. He tries to imagine the path from here to the lobby: the three flights of stairs, the scuffed linoleum landing, the prospect of someone—anyone—seeing him like this.

He tries to imagine how Steph will escalate if he refuses, what new dare she’ll manufacture from the remains of his dignity.

“Do I at least get to pick the shoes?” he says, half a joke.

She beams. “You’re learning.”

He changes in the bathroom this time, locking the door out of a paranoia that feels less irrational with every passing minute. The bikini, once merely garish, now feels like a tattoo. He adjusts the triangles, tries to minimize the bulge in the bottoms, and gives up. His reflection in the medicine cabinet is surreal—a haunted sex doll in drag, all sharp knees and uncooperative hips. He tries to stand like a woman, whatever that means, and ends up just looking lost.

He wraps the robe around himself until the last possible second, then tiptoes to the front door. Steph stands by, phone in hand, filming his approach with the gravity of a documentarian.

“Ready?” she says.

He nods, instantly regretting it.

“Lose the robe.”

He does, shivering, and waits for her to open the door. She does it with a flourish, bowing as if introducing a magician to the stage. Andrew steps into the hallway, the cold air biting at his thighs. He considers, briefly, sprinting the whole way. But Steph’s voice floats after him:

“Slowly, please. And shake your ass like you mean it.”

He wants to die. Instead, he walks, hips swaying in a parody of femininity, the hallway lights strobing each humiliation into his brain. The stairwell is unoccupied, but the mail alcove is visible from the courtyard, which in turn is overlooked by half a dozen apartments. He is halfway down when he hears a sound—a door opening on the landing below.

He freezes. For one atomic moment, he contemplates flight, but his legs are made of wet string. The footsteps ascend, slow and unhurried, and then Derek Sanders comes into view.

Derek is everything Andrew isn’t: tall, broad, athletic, sun-bleached hair and a perma-tan that suggests a personal relationship with both the gym and the outdoors. He’s wearing a hoodie and running shorts, earbuds dangling from his neck. He stops short at the sight of Andrew, eyes going wide, then slow-rolling into a grin.

“Well,” Derek says, “this is a hell of a way to meet your neighbors.”

Andrew wants to vaporize on the spot. He forces a smile, all teeth.

“New look,” he manages. “Very, uh, summer-forward.”

Derek leans against the banister, openly admiring. “You pull it off. Most guys couldn’t. You’re braver than me.”

Andrew can’t tell if he’s being mocked or sincerely complimented, which is somehow worse. “Thanks,” he says, wishing he could crawl into the utility closet and die among the mops.

Derek’s eyes crinkle. “You got a dare, or just feeling yourself tonight?”

The truth sits on Andrew’s tongue, sticky and undeliverable.

“Bit of both,” he says, hoping it sounds credible.

Derek laughs, a warm, easy sound. “Rock on, man. If you’re gonna do it, you gotta *own* it.” He thumps Andrew on the shoulder, the touch both brotherly and a little possessive. “Catch you around.”

He disappears up the stairs, and Andrew is left alone with his shame and the sound of his own heart trying to jailbreak out of his chest. He does not linger. The rest of the journey is a blur—a dash to the mailbox, the cool metal biting at his fingers, the shuffling of ads and bills, then the sprint back upstairs.

At the door, he finds Steph waiting, camera rolling.

“Did you have fun?” she asks, voice syrupy with anticipation.

He barrels past her, throws the mail on the counter, and retreats to his room. He half expects her to follow, but she lets him stew in silence. He shivers for a while, then, curiosity a toxin he can’t resist, ventures back out.

Steph is on the couch, scrolling through her phone, the wine glass refilled and balanced on her knee. She looks up as he approaches, lips pursed.

“You did well,” she says, without irony. “Derek got a great look at you.”

Andrew collapses onto the armchair, face in his hands. “He’s going to tell everyone.”

“Probably,” Steph allows. “But they won’t believe him unless he gets photographic evidence.” She turns the phone screen toward him: a perfect shot of Andrew, ass to the camera, bending for the mailbox. “Good thing I’m thorough.”

He stares at the image, gut knotting. “You didn’t.”

Steph leans in, voice dropping to a whisper. “Relax. It’s just for me. Unless you want to make it public, in which case…”

He shakes his head, violently. “No.”

“Then we have an understanding.” She beams, a sun breaking through storm clouds. “Blackmail isn’t nearly as fun if the victim doesn’t have some say in it.”

Andrew slumps deeper into the chair, feeling the contours of his fate slot into place.

Steph drains her glass, then sets it aside with the air of a judge passing sentence.

“You’re a good sport, Andrew. I mean that. But if you want to know what’s next, I’d start thinking about how you feel about crowded public spaces.”

He doesn’t respond, but she continues, warming to the subject.

“I’ve been meaning to hit the mall. There’s a place that does full makeovers—hair, nails, the works. We can get you a new outfit, something more, I don’t know, ‘elevated.’” She makes finger quotes in the air. “Maybe we’ll try some heels, see if you can walk in them. Or we could do a whole day: brunch, shopping, a few cocktails. Maybe you’ll even make some new friends.”

Andrew closes his eyes, tries to picture it: himself, a scarecrow in drag, paraded through the catacombs of consumer culture. The horror of it is almost transcendent.

“Please,” he says, the word so quiet he’s not sure it leaves his mouth.

Steph is instantly in his space, crouching in front of him, her hands on his knees.

“Hey. Look at me.”

He does.

“You’re not a prisoner,” she says, gentle but unyielding. “You can walk away anytime. But if you’re in, you’re *in*.”

He searches her face for a crack, a seam, any sign of weakness. There is none.

He thinks about the photo on her phone, about Derek and the probability curve of gossip, about the soft, secret thrill that underlies his humiliation like a bass note.

“I’m in,” he says, voice breaking on the last word.

Steph smiles, the kind that feels like both a reward and a dare.

“That’s my girl,” she says.

The world is a little louder now. Andrew sits back, waiting for the city to catch up to him. He is no longer sure who he’s becoming, but he knows this much: the story will get told, one way or another.

He just hopes, when it does, that Steph is the one telling it.