A Girlfriend's Dare: Ch. 09

He wakes up with his mouth dry and a chemical taste on the back of his tongue, the way hangovers always start: not with a bang but with a slow, spreading poison.

The last thing he remembers is Steph straddling him, her voice low and sticky in his ear, and Derek laughing from the other side of the room as they compared notes on how many times they'd made him cry. The humiliation should be old by now, but his body always finds a new way to keep the edge fresh. He's still wearing the breastplate, the silicone sticky with sweat, and the thong--god, the thong--is glued to his skin like a confession.

He drags himself from the bed, muscles jellied and aching, and blinks at the clock.

It's noon. There's no sign of Steph or Derek, but a note has been left on the pillow:

"Eat. Hydrate. New game at 4pm. Dress code: whore. - S"

He finds coffee in the kitchen, which is kind of Steph, and pours a mug before he realizes he's on the apartment's security cam, the little red dot in the corner winking at him. He resists the urge to flip it off, knowing Steph has an entire folder of screenshots waiting to be weaponized.

He sits, scrolls his phone, and tries to be numb.

At 3:30 exactly, the front door slams open. Steph is back, eyeliner even sharper than yesterday, dressed in a latex catsuit that manages to be both terrifying and incredibly hot. Derek is behind her, wearing gym shorts and a t-shirt with the sleeves cut off, a duffel slung over his shoulder.

"Chop chop," Steph calls, clapping her hands. "You've got twenty minutes to turn yourself into something Derek's followers will actually jerk off to. You remember what happened last time, right?"

He remembers. He remembers the way Steph made him watch the entire video, frame by frame, stopping every time he flinched or lost the rhythm. "If you can't even pretend to enjoy it," she'd said, "we'll make you do it until you do."

He doesn't want to know what the new game is, but the alternative--refusal, resistance--is impossible to imagine.

He goes to the bathroom and puts on the new wig Steph left on the counter: long, black, synthetic, cut with heavy bangs that make him look like a cross between a J-pop starlet and a sex doll. He reapplies the foundation, blush, the lash extensions, and the matte lipstick that Steph prefers. He slides into the cherry-red PVC skirt that rides his ass like a curse and a tube top two sizes too small, then sits on the bed and waits.

They come in together, Steph with her phone already filming, Derek with a tripod and an LED panel. Derek's presence has always made things more dangerous; his energy is predatory, less playful than Steph's, and Andrew knows--knows--that if things ever go off script, Steph will let him do whatever he wants.

"Ready, cupcake?" Derek asks, tossing the duffel on the floor and unzipping it to reveal ropes, a spreader bar, a stack of butt plugs in ascending sizes, and a white plastic bottle labeled "poppers."

Steph sets her phone on a little gimbal and flips to selfie mode. "Today's challenge: the Bimbo Livestream. Derek's going to run the tech, and you, sweetie, are going to make us famous."

He blinks, disbelieving. "You're... streaming this?"

"Not under your real name," Steph says. "We're not monsters." She grins, the corners of her mouth glossy and menacing. "But if you give us any shit, I'll post your email and home address in the chat and see how many horny losers want to send you presents."

He swallows, and the bitterness in his mouth spikes.

They set up the lights and the camera with surgical precision, Steph narrating for her imaginary audience as she does his makeup touch-ups and double-checks the frame. Derek adjusts the tripod, then points to a spot on the rug in front of the sofa.

"Knees," he says.

Andrew kneels, folding his hands over the skirt to hide the bulge from the cage, but Steph yanks his hands away and arranges them behind his back, then zip-ties his wrists together with a neat click.

"Don't slouch," she says, and slaps him across the face--not hard, but enough to sting and bring tears to his eyes.

She's livestreaming before he even gets the chance to breathe.

The chat is an instant avalanche: "damn that's a real femboy huh," "look at those tits lmao," "is this a humiliation stream or is he actually into it," "yo when's the sissification start." The usernames are all variations on "Chad" and "Alpha" and "Daddy," and the donations start rolling in as soon as Derek turns on the mic and tells Andrew to say hello.

Steph leans in, her face a perfect mask of cruelty. "Go on, sugar. Tell them your name. Tell them what a nasty little bimbo you are."

He tries to summon his stage voice, but it comes out thin and warbling. "Hi, I'm... Annie," he says, because that's what they want. "I'm a pathetic sissy faggot who loves being used."

The chat lights up: "That's more like it," "omg he actually said it," "this is fuckin wild."

Steph paces behind him, one hand in his hair, tugging the wig every time he misses a cue or lets his voice drop out of falsetto.

They start with the basics: show off the cage, bend over and show the plug, recite the insults that the chat types in--each one a new permutation of "slut," "whore," "cock-hungry," and a hundred variations he'd never imagined existed. Steph reads the worst ones aloud, her eyes gleaming, and every time she does, Derek makes him repeat it twice, then thank the chat for their generosity.

It goes on for almost an hour, the tasks escalating: edge yourself for the camera, suck on the biggest plug, call Derek "Daddy" and Steph "Mistress" in every sentence. His knees are numb, his mouth full of the acrid taste of tears and lipstick, and his own cock--trapped and abused--pulses against the plastic until he feels like he might piss himself.

Halfway through, Steph pulls out the poppers and uncaps the bottle, waving it under his nose. The rush is instantaneous, blood roaring in his ears and vision tunneling. She pushes his face to the carpet and drives the largest plug inside him in one slick, brutal motion.

He screams, and the chat loses its collective mind.

Derek picks up the camera and moves it in for a close-up, narrating in the mock-serious tone of a sportscaster: "Look at that gape, folks. You're seeing a bimbo in her natural habitat." He thumbs the plug, working it in and out while Steph pulls Andrew's head up and holds the bottle to his lips, forcing another inhale.

The sensations blur--pain and pleasure and humiliation fusing into a single, inescapable loop. He feels untethered, every cell in his body hot with shame, and when Steph orders him to thank the donors for their generosity, he does it without thought, voice wobbling but clear.

The peak comes, as it always does, when Steph decides the chat has paid enough.

"Final act," she announces, "and then we'll let our little whore clean up." She unlocks the cage, hands trembling with anticipation, and wraps her fist around his cock. Derek is behind him, plug buried to the hilt, and together they work him over--one from the front, one from the back--until the sensations blur into a single, catastrophic release.

He comes, hard, the orgasm tearing through him and painting the rug in four long, shuddering spurts. Steph claps, then wipes the mess with his own hair, smearing it across his face as Derek films a close-up for posterity.

The chat goes feral: "holy shit," "bitch is a true cumdump," "yo I'm saving this vid," "bet he'll never walk straight again."

Steph ends the stream and high-fives Derek. They leave him on the floor, wrists still zip-tied, and go into the kitchen to fix themselves drinks.

He's alone, blinking at the after-image of the LED panel, when his phone vibrates.

The text is from an unknown number. There's a screenshot attached, a frozen frame from the last minute of the stream--his face, smeared with cum and tears, lips glossy and parted.

The message: "hey Andrew. remember me?"

His stomach drops. The contact photo is a selfie: a wide, predatory smile, and skin the color of good espresso.

Jamal.

He hasn't thought about Jamal in almost a decade, but the memories are still raw: the summer spent dodging fists in the locker room, the time Jamal locked him in a janitor's closet and pissed through the vent. Jamal was a monster, not just in the way that all popular boys are, but in a way that seemed engineered for maximum suffering.

He types back, numb fingers hitting the wrong keys.

"what do you want"

Jamal replies instantly: "i want to see if you're still a bitch. give me your address. or i send this to your boss."

He stares at the phone, weighing the consequences. He knows Jamal is serious; Jamal never bluffed, never needed to. He texts the address, hits send, then sits and waits, the cold carpet rough against his thighs.

Fifteen minutes later, there's a knock at the door. He tries to call out for Steph, but his voice is gone.

Steph answers, and when she sees Jamal in the hall--six-four, built like a linebacker, gold chain visible even under a crewneck--she steps back and grins.

"You must be Jamal."

"That's me," he says, eyes sliding past her to where Andrew still kneels, wrists bound, face a ruin of makeup and humiliation.

Steph waves him in. "We just finished a show," she says. "You're welcome to join the afterparty."

Jamal stalks over, looming above Andrew, and tilts his chin up with one enormous hand. His grip is rough, but not unkind; more clinical, as if he's appraising a new piece of gear. "Damn," he says, "I thought you were faking all that sissy shit, but you really went full bitch mode."

Andrew tries to look away, but Jamal holds his head firm.

"Don't move," he says, and runs a thumb across Andrew's lips, scraping away a smear of Steph's gloss. "You ever sucked a black cock, faggot?"

He shakes his head, lips trembling.

Jamal laughs, loud and warm, and lets go. "You about to."

Derek is already setting up the camera again. Steph stands behind Jamal, hands folded, her eyes hungry.

Jamal pulls his dick out of his sweatpants, and it is exactly as big and intimidating as Andrew remembers from the gym showers in high school. He grabs the back of Andrew's head and pushes forward, the tip of his cock heavy and hot against Andrew's lips.

"Open up," Jamal says, and Andrew obeys.

The taste is different from Derek--more sweat, more animal--but the muscle memory is the same. He takes as much as he can, jaw aching, and Jamal laughs every time he gags or chokes, but never lets go. He fucks Andrew's face slow, then faster, using him like a toy, and the sound of it--wet and obscene--echoes in the living room.

Derek circles with the camera, filming every angle. Steph stands at Jamal's shoulder, running her nails down his back, murmuring encouragement into his ear.

"Show him what a real man tastes like," she whispers. "He's been waiting for this his whole life."

Jamal grins, then starts throat-fucking Andrew in earnest, both hands on the back of his head, cock driving in and out until Andrew's face is wet with spit and tears.

"You a good cumdump, Andrew?" Jamal says, voice low and dangerous. "You ready for Daddy's load?"

Andrew can't answer, mouth full, but nods as best he can.

Jamal holds his head down, shuddering, and empties himself in a series of hot, bitter spurts. He pulls out, the tip still leaking, and wipes it across Andrew's cheek before tucking himself away.

He turns to Steph, as if Andrew no longer exists.

"That's a good bitch," he says. "You got anything to drink?"

She laughs, the sound edged with hunger. "You want whiskey or wine?"

"Whiskey," Jamal says, and follows her into the kitchen, leaving Andrew on the floor, still zip-tied, cum and spit and makeup streaked across his face.

He sits there, breath hitching, and waits for the next instruction.

* * *

They keep him on his knees for the next hour, Jamal and Derek taking turns seeing how many different ways they can make him gag. Steph stays behind the camera, directing the scene with the cold efficiency of a pornographer, occasionally stepping in to slap his face or stuff a new plug up his ass.

Jamal is relentless, and every time he finishes, he makes Andrew clean the mess with his tongue, then say thank you. "You're a fast learner," Jamal says, voice lazy. "Bet you wish you'd sucked my cock back in high school. Maybe I wouldn't have kicked your ass so much."

Derek films everything, uploading clips to a private chat where the donations come in even faster than before. The chat is obsessed with Jamal, with his size, his dominance, the way he makes Andrew cry without effort. The usernames turn racist and wild, but Jamal doesn't care; if anything, it fuels him.

Eventually, Jamal gestures for Steph to come closer.

"You ever had a real man, girl?" he asks.

She smirks, but her eyes are hungry. "Convince me."

Jamal pulls her in, kissing her hard, and Derek sets the camera down to watch. They make out over Andrew's head, Jamal's hand snaking up Steph's skirt, then yanking her panties to the floor. Steph laughs, but lets him bend her over the arm of the sofa, heels digging into the carpet.

Jamal lines up behind her, spits in his hand, and fucks her raw, the sound wet and obscene, the force of his hips nearly knocking the sofa over. Steph bites the cushion, moaning, her eyes on Andrew the whole time.

"You see this, faggot?" she says, voice muffled. "You'll never be a real girl. All you'll ever be is a cumrag."

Jamal pounds her harder, then pulls out and cums across her back, the white ropes standing out against the black latex of her catsuit. He smears it in with his hand, then makes Andrew crawl over and lick it off.

Andrew does, mouth trembling, the taste of Steph and Jamal mixed together on his tongue.

He's lost in it, the humiliation so total it's almost holy.

Jamal grabs him by the hair and lifts his face.

"You like this, don't you?" Jamal says. "You like being a white bitch. Bet you wish everyone from school could see you now."

He does, almost. The shame is so sharp it's indistinguishable from arousal.

Steph watches, her cheeks flushed, her body shaking with aftershocks. She grabs Andrew's head and kisses him, biting his lip hard enough to draw blood.

"I think we broke him," she says to Derek, who's still filming.

"That's the point," Derek replies, and uploads another clip.

Jamal wipes himself off on Andrew's wig, then zips up.

He leaves an hour later, promising to bring friends next time.

Steph unties Andrew's wrists and helps him up. She kisses his forehead, then whispers, "You did so good, baby. I'm proud of you."

He wants to say thank you, but the words are gone.

He sleeps on the floor that night, breastplate and wig still glued to his body, the taste of Jamal and Steph and shame lingering on his tongue.