A Girlfriend's Dare: Ch. 13

The next morning, the world was still spinning. The eggs were gone, but the chat--Jamal's favorite word now, "the chat"--was alive, carnivorous, hungry for more.

Annie didn't sleep, not really; she drifted on a tide of shame and adrenaline, alternating between hours of staring at the ceiling and hours of scrolling through the anonymous DMs that filtered into the sissy stream's tip jar. She was famous now, in the exact way she'd once spent years online praying she'd never be.

The kitchen was a ruin: empty bottles, feathers on the linoleum, a single gold egg jammed between the fridge and the wall. Steph was up early, slicing strawberries with an intensity that made it look like she was hoping to hit bone. She didn't speak until Annie had been standing in the doorway for a full minute.

"He wants to do it again," she said.

Annie didn't answer. She already knew.

* * *

The plan was simple: maximum exposure, minimum plausible deniability. Jamal wanted a public. Not an audience--he had that already, a thousand nerds with one hand in their pants and the other on the upvote button--but a crowd, a live-action humiliation with real consequences and real strangers and, if he could swing it, the chance of a cop showing up.

He met them at the bodega, this time fully dressed. Annie clocked the difference immediately: no gym shorts, no hoodie. Instead, a tailored button-down (untucked but still sharp), black jeans, and a bomber jacket that made his shoulders look cartoonish. He was on the phone, pacing out front, voice so low and professional that for a second Annie imagined the last six days had been a hallucination.

When he spotted them, he hung up and grinned. "Morning, princess," he said, then nodded at Steph. "You ready for cheer camp?"

Steph rolled her eyes, but the smile curled her lips anyway. "Don't you need, like, a permit to host public events?"

Jamal's smile widened. "That's why we're not hosting. We're just... participating."

He popped the trunk of his car and produced a shopping bag: white vinyl and glossy, with a pink logo so cheerfully obscene that Annie felt her guts cramp on sight.

"Try it on," Jamal said, handing over the bag. "It's got everything you need."

They walked to a bathroom in a fast food place two blocks from the park. Jamal waited outside. Steph followed Annie in, not to help, but just to see.

The outfit was worse than she imagined: a pink and white cheer skirt, not even pretending to cover the ass, with "SISSY SLUT" appliquéd across the back in bubble letters. The crop top was cut so high it bordered on "pasties plus a prayer," and the matching panties were mesh, with "AVAILABLE" in rhinestones on the crotch. There was a tiny, frilly apron, the kind you'd see in a Hooters but made for a porn parody. The shoes were knee-high white boots, the laces stiff and plasticky.

Steph helped with the wig--platinum again, with pink bows on each pigtail--and made quick work of the makeup. She used glitter, heavy blush, a gloss that tasted like melted Skittles. "You don't have to do this," she said once, but it sounded more like a dare than a mercy.

When they emerged, Jamal was waiting with his phone out, streaming to a private group. "Damn," he said, doing a slow, predatory circle. "You might start a riot."

He tossed Annie a baton--cheap, foam, glittery. "Don't fuck it up," he said.

They walked together to the park. It was early, but the playground was already alive: joggers, dog-walkers, a group of day-drinking teens on a picnic blanket. Jamal picked a spot near the amphitheater and set up his phone on a portable tripod.

He checked the lighting, then looked at Annie. "You ready?" he said.

She wasn't. But she nodded anyway.

Jamal turned to Steph. "You're on camera duty. You got the eye for it."

She took the phone, hands steady.

Jamal cleared his throat, cracked his knuckles, and addressed the imaginary audience. "What up, sickos. It's your boy Jamal, and this is the live sissy slut challenge. Today, we got Annie here, and she's gonna show us some school spirit."

He paused, then added, "No safe words. No takebacks. If she fucks up, you know what to do. Tips make it worse."

The chat was already rolling: a blur of purple and red emojis, usernames like "Coach Daddy" and "Spitroast69" egging them on. Jamal glanced at the screen, then back at Annie.

"Go on," he said. "Show us your routine."

Annie felt her hands shake. She stepped onto the grass, the skirt fluttering, and tried to remember the steps Jamal had drilled into her the night before. She fumbled the baton immediately, dropped it, bent over to pick it up. There was a roar of laughter from the teens on the blanket.

"Higher!" Jamal called. "Show some energy!"

She forced a smile and tried again. The boots pinched, the wig itched, and the crop top kept riding up until she was in constant danger of a wardrobe malfunction.

She did a series of kicks, nearly falling over, then a cartwheel that ended with her ass in the air and the skirt at her armpits.

The chat exploded: "A++," "good girl," "flash the panties again."

Jamal motioned for her to come closer. "Now tell them your name," he said, loud enough for the passersby to hear.

She hesitated, then squeaked, "I'm Annie. I'm a worthless sissy slut and I love to perform for real men."

The words hung in the air, then rippled through the chat like a shockwave.

Steph zoomed in for a close-up, catching the bright red flush of Annie's cheeks, the gloss shining on her lips.

Jamal grinned. "Now let's get the public involved."

He strode to the teens' blanket, gestured for Annie to follow. She did, mortified, and stood while Jamal made introductions.

"Hey, you guys want to see something crazy?" he asked.

The group--two girls, three boys, all clearly high--perked up.

"This is Annie. She's trying out for the cheer team. You wanna judge her?"

They all agreed instantly.

"Cool. If she nails the routine, you each get to give her a dare. If she fucks up, it's double dares."

Steph filmed from the sidelines, her eyes never leaving Annie.

The routine was a disaster. She dropped the baton twice, tripped over her own boots, and on the final high-kick, the mesh panties flashed "AVAILABLE" so blatantly the girls started cackling and one of the boys actually spit out his Monster energy drink.

"Wow," said the ringleader, a skinny kid in a crop top and Doc Martens. "Is this, like, a TikTok thing?"

Jamal shrugged. "Nah, it's just for fun. You guys get to dare her now."

The boys conferred. "First dare," said one, "you gotta run around the playground and get five random people to sign your ass. With a Sharpie." He produced one from his fanny pack, tossed it to Annie.

She looked at Jamal. He winked.

Steph kept filming.

It was worse than she imagined: the first person was a middle-aged dad with a jogging stroller. He glanced at the Sharpie, then at Annie, then at the phone pointed at them. "Is this legal?" he asked, half-laughing.

Jamal answered for her. "It's all in good fun, man. Go ahead."

The dad shrugged, signed "Mike S." on her left cheek. His toddler clapped.

Next was a pair of older women in sun hats. They giggled, then signed with fake names--"Queen Bitch" and "MILF Supreme"--and insisted on selfies.

The last two were a couple of skaters, who wrote "SLUT" and "4 SALE" in block letters.

By the end, the skirt was useless, and Annie's ass was a billboard.

The chat was ecstatic.

Jamal called her back to the blanket. "Two more dares," he said.

The girls huddled, then announced, "You have to do a lap of the park, but you have to ask every guy you see to slap your ass. On camera."

Jamal whooped. "That's so good."

Steph hesitated, but kept the phone rolling.

Annie started her lap. The first few men refused, shaking their heads or ducking away. But after a while, the momentum built, and by the fifth or sixth encounter, it was routine: a quick glance, a shocked laugh, then a hard smack that echoed in the cool morning air. The noise drew attention. Soon, people were waiting, egging each other on, recording with their own phones.

At the halfway point, a group of college-aged runners lined up for a group photo with her, each taking turns slapping her ass for posterity.

Jamal and Steph watched from the edge of the path.

"She's a fucking natural," Jamal said, pride and hunger in his voice.

Steph looked at him, then at Annie. "You're loving this," she said, not quite a question.

He shrugged. "You're not?"

She considered, then shook her head. "Not at first. But now?" She trailed off, eyes locked on the parade unfolding before them.

The last dare came from the girls at the blanket: "You have to chug a beer, then do the splits."

Jamal produced a can, already cold. "Ready?" he asked.

Annie nodded, wiped the sweat from her brow, and upended the beer. It splashed down her chin, soaked the crop top, and ran in sticky rivulets over the mesh panties.

She tried the splits and nearly tore the skirt in half. The applause was instant and unrestrained.

Jamal handed her a towel, then motioned for Steph to wrap the shoot.

"Anything you want to say to your fans?" he prompted, as Steph zoomed in.

Annie licked her lips, voice hoarse.

"Thank you for watching. Thank you for humiliating me. Please, keep sending dares. I'll do anything."

Jamal clapped, then pulled her into a side hug, all but lifting her off the ground.

Steph stopped recording and leaned in, close enough to smell the sweat and shame.

"You did good, princess," she whispered.

Annie shivered. She'd never felt so empty.

* * *

They walked home in silence, Jamal with his arm around Steph, Annie trailing behind. Her head was spinning, her skin still burning from the slaps. She could feel every eye on the street boring through the tiny skirt, the ruined wig, the signature graffiti on her thighs.

Back at the apartment, Jamal poured shots for all three, then raised his glass. "To the best sissy in the city," he said.

Steph grinned, and clinked her glass against Annie's. "To public service," she said.

They drank.

Jamal closed the laptop, wiped the sweat from his brow, and nodded at the phone. "You know, we broke a thousand live viewers?" he said.

Annie blinked. "Is that good?"

He laughed, deep and genuine. "It's fucking historic."

Steph poured another round, her hand lingering on Jamal's wrist.

They sat together, three in a row, the night still buzzing around them.

No one spoke. There was nothing left to say.

"Does it ever stop?" Steph asked, eyes closed, head on Jamal's chest.

He thought for a second. "Not unless you want it to," he said.

She considered this and began to feel some guilt for her boyfriend Andrew. Jamal reached down and began to rub her pussy and asked again more sternly:

"Not unless you want it to,"

Steph felt his manly hands on her pussy and sadly shook her head and whispered: "No Sir."

"Good," Jamal said, and kissed her forehead.