A Girlfriend's Dare: Ch. 08

It took about one hour for Derek to reply. It took Steph four minutes more to escalate the entire game.

Andrew was naked, freshly showered, with a towel wrapped around his waist and the marks from last night's restraints still faintly banded on his wrists. He was contemplating, with the grim focus of a death row inmate, how to word a follow-up to Derek's "You're a legend. Tell me when and where," when the apartment intercom warbled.

It was Steph, of course. She always arrived unannounced. He pressed the buzzer, steeling himself, and was halfway to the kitchen when she blew through the door, a blur of shopping bags, platform boots, and the kind of sunglasses that belonged on a corpse at a celebrity funeral.

"Good," she said, not even looking at him. "You're not dressed. Saves time."

He tried to speak, but she had already set the bags on the dining table and started unpacking them with surgical efficiency: a wig stand, a can of industrial adhesive, several tubes of makeup, an aggressively pink two-piece set that was mostly plastic wrap, and a vacuum-sealed pouch labeled "FEMALE BODYSUIT--ULTRAREALISTIC BREAST FORMS." The sight of the last item triggered a kind of existential arrhythmia.

"Sit," she said, pointing at a kitchen chair.

He did. The towel was not enough to keep him from shivering.

Steph unzipped the pouch and pulled out the breastplate. It was silicone, pale and cold, with nipples so realistic they looked like they'd been grown in a lab. She flopped it onto the table and turned her attention to the wig stand. The hair was platinum, bottle-blonde, styled in loose waves that would have looked at home on a porn star from a forgotten decade.

"I thought you liked me brunette," he said, the words automatic.

Steph snorted, prepping the wig with a spray that made it gleam. "This isn't for me. This is for Derek. He's got a type."

He felt his face flush. "He's coming here?"

Steph gave him a look that could have stripped wallpaper. "Did you think this was just going to be some sick little online catfish? I told you, you're in now. He's on his way. ETA forty minutes."

It felt less like forty minutes than forty seconds, the way Steph operated. The next half hour was a blur: she sat him down at the bathroom counter, slapped a towel around his shoulders, and began the transformation with the grim determination of a drag show drill sergeant. She started with the wig, yanking it down so tight it made his scalp throb, then applied adhesive around the hairline, smoothing the edges until the platinum merged with his skin.

Next came the breastplate. It was heavier than it looked, clammy and unyielding, the surface dimpled with pores and a faint sheen of powder. Steph stretched it over his chest, tucked the edges beneath his arms, and smoothed the seams with some kind of solvent that smelled like nail polish remover and regret.

When she was satisfied with the fit, she tackled his body hair. "This is going to hurt," she warned, then began to wax his arms, his chest, his stomach. She did not skimp on technique. By the time she finished, he was as smooth as a mannequin and twice as sensitive.

Makeup was last. She painted his face in layers--primer, foundation, contour, blush, lipstick--and finished with a set of false lashes so thick they cast a permanent shadow on his cheeks. When she was done, she stepped back, arms folded.

Andrew stared at his reflection in the mirror. He was unrecognizable. The breastplate gave him a cartoonish hourglass, the wig a halo of artificial glam. His lips were glossy, his eyes rimmed in black, and the stubble of his jaw had vanished beneath a coat of primer. He looked like a YouTube tutorial gone wrong.

Steph nodded, pleased. "Perfect. Now for the outfit."

She handed him the plastic-wrapped set. The top was a hot-pink crop, cut so low it barely covered the new, rubbery mounds of his chest. The skirt was a micro-miniskirt, more of a suggestion than a garment, with a matching G-string underneath.

He looked at the clothes, then at her. "You're serious."

Steph was already texting. "I told Derek you've been obsessed with him for months. That you've always wanted to be a slutty little porn star. He's expecting you like this. If you back out now, I'll send him the unedited version of your confession video."

He could feel the humiliation crawling up his skin like an infestation.

"Why are you doing this?" he asked.

Steph rolled her eyes. "Because I want to see how far you'll go. And because Derek's a freak, which you'd know if you ever listened when I talk. You're not going to believe half the shit he's into."

There was a knock at the door. It was sharp, impatient, the knock of someone who has never had to wait for anything in their life.

Steph's face lit up. "Showtime."

She walked him to the door, one hand on his lower back. He considered bolting, but the thought was laughable; Steph would drag him back by the wig if she had to.

She opened the door.

Derek stood in the hallway, wearing a tank top and track shorts, a duffel bag slung over his shoulder. He looked at Andrew, did a double-take, then grinned wide enough to show all his teeth.

"Holy shit," he said, stepping inside. "That's really you?"

Andrew tried to say something--anything--but the only sound was a faint whimper. Derek looked him up and down, then at Steph, then back at Andrew.

"Dude," Derek said, "I had no idea you were this into it. You look... fuck, you look incredible. Turn around for me."

Steph nudged him in the ribs. Andrew turned. Derek whistled.

"Damn," he said. "I didn't know you had it in you. I mean, I always thought you were a little... you know. But this is next level."

Steph slipped past Andrew and perched on the arm of the couch. "You like?"

Derek dropped the duffel and sat opposite her. He leaned forward, elbows on his knees, eyes glued to Andrew. "Yeah. I like." His gaze was hungry in a way that was both flattering and terrifying.

There was a silence, electric and oppressive.

Derek spoke first. "So, uh, how's this work? You want me to call you Andrew, or...?"

Steph piped up, "She's Annie now. That's what she told me, right?"

Andrew tried to correct her, but the word stuck in his throat.

"Yeah?" Derek said. "Annie? That's hot. You got a thing for sissy names?"

He realized, too late, that any answer would only dig the hole deeper. "I... I guess."

Derek grinned. "Cool. So, Annie, come sit." He patted the spot beside him.

Andrew hesitated, then obeyed. The skirt rode up, the G-string digging into his ass. He sat, legs together, hands folded in his lap.

Derek leaned in, close enough that Andrew could smell the clean sweat on his skin. "You ever done this before?"

He shook his head.

"Never with a guy?"

Another shake.

Derek looked over at Steph, who was smiling like she'd just watched a car crash and found it exhilarating. "This is wild," he said. "You know I've been looking for a sub since my last girlfriend bailed, right? She couldn't handle it. But if you're really down..."

Andrew's heart was in his throat.

Steph tilted her head. "He's down. Aren't you, Annie?"

He swallowed. "I'll try."

Derek's eyes narrowed, searching for sarcasm or cowardice. He found neither.

"You ever take a cock before?"

Andrew's ears were burning. "No."

Derek smiled. "Good. I like training fresh meat."

Steph laughed, the sound low and filthy. "Told you he was a freak."

Derek shifted, his shorts tenting. He made no effort to hide it. "So, how far are you willing to go?"

Andrew's mouth was dry. "Whatever Steph says."

Derek looked at her. "Is that right?"

Steph shrugged. "She's a good girl. She just needs motivation."

Derek thought for a moment, then smiled. "Alright. You want this to feel real?"

Steph nodded.

"Then let's make it official." Derek stood, grabbed the duffel, and pulled out a coil of nylon rope, a ballgag, and a thick, black strap-on harness. He set them on the table with the casual air of unpacking groceries.

"First thing," he said, "get on your knees."

Andrew slid to the floor. The wig bounced as he moved, a surreal reminder of the new rules of engagement.

Derek fished a camera from the bag, a GoPro on a tripod. He set it up, aimed it at the living room, and pressed Record. "Say hi to the audience, Annie," he said.

Andrew stared, wide-eyed.

Derek crouched in front of him, the camera at their backs. "You want me to call you a whore? A cumslut? What does it for you?"

Andrew looked at Steph, who gestured for him to answer.

He whispered, "Whore."

Derek nodded. "Good girl." He reached forward, his palm huge on Andrew's fake breast, and squeezed. "You're going to suck my cock now. You got it?"

Andrew nodded. Derek handed him the harness and cock. It was silicone, thick, veined, angry red. "Put it on," Derek said. "Practice makes perfect."

He fumbled with the straps, the plastic slippery with nerves. When it was on, Derek stood, dropped his shorts, and revealed his own cock--larger, uncircumcised, already hard.

"Start with the toy," he said. "Then you can work up to the real thing. Steph, you want to supervise?"

Steph leaned in, eyes locked on the action. "Go slow," she said. "She's never done this before."

Andrew knelt, the breastplate pressing into his chest, the wig tickling his neck. He took the dildo in both hands and slid it between his lips, the taste rubbery, the sensation both ridiculous and arousing. He sucked, slow at first, then with more enthusiasm as Derek narrated instructions.

"Deeper," Derek said. "Try to get the whole thing in. Use your tongue. Yeah, that's it. You look like you were born for this, Annie."

The words made Andrew's scalp tingle. He could feel his own cock straining in the cage, the pressure exquisite and horrible.

Derek watched for a minute, then switched places. "Your turn," he said, and guided his cock to Andrew's lips.

It tasted of sweat and salt and inevitability. Andrew opened, let the head slip past his teeth, and tried not to gag as Derek pushed deeper. Derek's hands were firm on the back of his head, holding him in place.

"You're a quick study," Derek said, thrusting slowly, letting Andrew adjust to the intrusion. "Most girls can't take it like that their first time."

Steph watched, eyes glazed, one hand under her skirt.

Derek fucked Andrew's mouth for a minute, then pulled out, a string of saliva connecting them.

"You want to make me cum, Annie?" he asked.

Andrew nodded, unable to speak.

"Then say it. Beg for it."

Andrew closed his eyes. "Please, Derek. I want your cum. Please. I'll be a good girl."

Derek grinned, then shoved back in, harder, faster, using Andrew's mouth like a toy. It was degrading and obscene and, in a way that defied logic, satisfying. Andrew felt his own cock pulse in the cage, leaking pre, the humiliation transformed into something like need.

It didn't take long. Derek grunted, shoved deep, and shot into Andrew's throat. The taste was foul, but Andrew swallowed, reflexively, not wanting to disappoint.

Derek withdrew, wiped his cock on Andrew's cheek, and patted him on the head. "Good girl," he said. "Very good."

Steph clapped, slow and deliberate.

Derek knelt, his mouth close to Andrew's ear. "You're mine now, you get that? If I tell you to crawl, you crawl. If I tell you to piss yourself, you do it. No more safe words. You obey."

Andrew nodded, the words etching themselves into his skull.

Derek turned to Steph. "You want to go next?"

She shook her head, smiling. "I'm just here for the show."

He shrugged. "Suit yourself. Annie, go to the bathroom. Clean yourself up. When you come back, you're going to be my little toilet slave. You know what that is?"

Andrew froze. "No."

Derek explained, in graphic detail.

Andrew felt his stomach turn, but also something else--a heat, a tremor that said he was already too far gone for anything but compliance.

Steph met his eyes, her gaze equal parts apology and triumph. "You heard him," she said. "Better hurry."

Andrew crawled to the bathroom, the wig askew, his cheeks streaked with tears and spit. He rinsed his mouth, fixed his makeup as best he could, and looked at himself in the mirror.

He didn't recognize the person staring back.

When he returned to the living room, Derek was naked, sprawled on the couch. Steph sat beside him, her skirt hiked up, hand absentmindedly stroking her thigh.

Derek patted his lap. "Come here."

Andrew knelt beside him.

Derek stroked his hair, then positioned him between his legs. "Open wide."

Andrew obeyed.

It was degrading in a way that erased all previous boundaries. Derek pissed straight into his mouth, the taste shocking and vile. Andrew choked, but Derek held his head, forced him to swallow every drop.

When it was over, Derek wiped the dribble from Andrew's chin with his thumb, then made him lick it clean.

Steph watched, her breathing ragged.

Derek stood, pulled up his shorts, and looked down at Andrew.

"You're a natural," he said.

He turned to Steph. "You want her for the weekend? Or is she staying with me?"

Steph considered, then said, "Let's split custody. I have plans for her."

Derek grinned. "Deal."

He left, shutting the door behind him.

Steph walked over to Andrew, knelt beside him, and cupped his face in her hands.

"You did so good," she whispered.

Andrew couldn't speak. The taste of Derek lingered.

Steph kissed him, gentle and slow. "You're going to be the best little slut this city's ever seen," she said.

He didn't want to believe her.

The night ended with Steph leading him to bed, curling around him like a serpent, her hand never leaving his caged cock. She whispered plans, fantasies, new ways to break him and remake him.

Andrew listened, and realized that this has gone too far. He needs to find a way out.