A Girlfriend's Dare: Ch. 07

Three weeks is a long time to live as a punchline. Andrew had not expected to survive it.

He had learned quickly that Steph's threats were always instructional, never idle.

The morning after the cage-and-plug incident, he'd tried to imagine a scenario in which she lost interest or forgot about him--a vacation, maybe, or the slow entropy of her attention span. But Steph's attention was bottomless. Within forty-eight hours, she had established a schedule: daily check-ins, mandatory photo documentation of his "training" (a word she deployed so often it lost all sinister connotation and became, instead, the weather of his days), and a strict ban on touching, removing, or even thinking too hard about the devices now governing his body.

She was, if anything, more creative from a distance. The first Monday, she had him walk to a copy shop and print out an entire packet of "Femdom Chastity Slave Rules" she'd found online. She instructed him to highlight the sections he found most personally degrading. "Extra credit if you do it in pink," she wrote. He did, and sent proof.

The rest of the week had proceeded in a similar vein: outfits ordered to his door (always in Steph's size, always one notch tighter than plausible); explicit instructions to shave, to wax, to moisturize and exfoliate ("You have to be soft for me, Andrew, it's nonnegotiable"); assignments to write confessional essays about what he learned from each humiliation. He submitted these via email, subject lines dictated by her: "Day 5: What I Deserve." "Day 7: My Sissy Fantasy." "Day 10: Why I Should Never Have Power Again."

There were evenings when he almost convinced himself he was in control. He managed to do his job remotely, to pay rent, to perform the minimal grooming expected of a human animal. He still had his books and his dumb little rituals--coffee brewed with precision, crossword completed in ink, the slow re-reading of texts from more optimistic eras.

But then he would get a text from Steph ("Show me your plug before 10pm or I'll make you wear it to work") and the illusion would collapse. He was in the orbit of her will, and there was no friction in the vacuum.

At night, the cage was a second pulse between his legs. He dreamed of being unlocked only to be abandoned, or worse, to be forced to beg for re-capture. In the mornings, he woke to a dull ache in his gut, a throbbing that neither faded nor grew--it was simply always there, like the low-grade hum of a malfunctioning refrigerator.

Two and a half weeks in, he thought the worst had already happened.

He was wrong.

* * *

Day 19, 08:54. He opened his inbox, dreading the ritual. Steph had migrated to Google Docs to keep track of his "progress," and the document's title bar--Andrew'S FEMINIZATION SCHEDULE, full-caps--glared from the bookmark bar like a neon scar. The latest comment from Steph read:

Today: 1. Order groceries (see approved list) and pick up at 5pm, *wearing dress #3*. 2. Complete 500 words on "Why Denial Is a Gift." 3. Clean plug, re-insert by 6pm. 4. Video call me at 8:30. DO NOT MISS.

He copied the tasks into his sticky notes app, as instructed. He did not yet know what the penalty for missing a deadline was, but he suspected she did.

The groceries were humiliating enough--a curbside handoff with the minimum-wage associate, forced to acknowledge the pink mesh poking from beneath his hemline--but Steph was always more interested in the psychological torture.

At 8:27, the call notification popped. She never waited for him to initiate.

He answered, and there she was: immaculate, hair pulled back, a ring-light giving her skin a supernatural glow. She wore a blazer, the kind that might have looked professional if she wasn't also in fishnets and nothing underneath. She smiled, like someone greeting an old enemy at a funeral.

"Hi, princess," she said.

Andrew made himself smile. "Hi, Steph."

"Did you follow my list?"

He nodded. "Groceries are in the fridge. Plug is clean. I'm wearing the dress."

She squinted at the camera. "Show me."

He had learned to anticipate this. He angled his laptop to give her a full-body shot: the dress was a polyester sheath in pastel yellow, clinging to every unkind line of his ribcage. The outline of the chastity device was unmistakable, even from a distance.

"Very cute," Steph said. "Twirl."

He did.

"Stop." She leaned into her webcam, predatory. "Are you wet?"

He blinked. "Uh--"

"I mean, are you leaking? I know the cage can do that."

He felt the flush start at his neck. "Sometimes."

She made a note on her phone. "You're probably ready to cum, then."

He felt his heart stop. "What?"

Steph grinned, but her eyes stayed cold. "I'm not a monster, Andrew. Eventually, you get a reward. But it's not going to be easy."

She let him stew in it. "You want to cum, don't you?"

He hated that the answer was already out of his mouth: "Yes."

"Say it better."

He paused, feeling the words ooze out. "Please, Steph. I want to cum. I'll do anything."

She smiled, satisfied. "That's more like it."

She tapped the phone again, reading from a script she had obviously prepared. "Here's the deal, Andrew. Tomorrow night, I'll come over. You'll dress as a bimbo whore--wig, makeup, heels, the whole thing. You'll tie yourself to the bed, spread-eagle, plug and cage both in place. If you impress me, I'll consider unlocking you. Maybe even let you cum for real."

Andrew tried to picture it: himself, wrists and ankles bound, Steph in command. The shame was nuclear, but underneath, an animal thrum of anticipation.

He nodded. "Okay."

"Say thank you," Steph said.

He did.

She hung up, and the sudden silence was as loud as anything he'd ever heard.

* * *

It took him three tries to find the right wig. Steph had left a bag labeled "FOR EMERGENCY FEMBOY ONLY" in his closet, and he pawed through it, hands shaking. The first was blonde, too brassy. The second was a bob, severe and businesslike, which seemed unlikely to win points for enthusiasm. The third was a cherry red, parted in the middle, with loose curls that trailed to his collarbones.

He spent an hour in front of the mirror, watching YouTube tutorials on smoky eye and contouring. He was less "bimbo" and more "gas station clown," but Steph had never penalized him for lack of skill--only lack of effort.

Next: the makeup. He caked it on, over-compensating for the blue in his jaw and the uneven terrain of his cheeks. He overlined the lips, careful to smudge them into a pout. The result was cartoonish, but it did not matter; he knew Steph would get off on the desperation.

The outfit was a pink slip dress, so thin it may as well have been smoke, and a pair of white thigh-highs with lace tops. He spent ten minutes wrestling with the garter belt, then another ten steeling himself to insert the plug, still slippery from the last round of cleaning. The inflatable bulb was awkward, but he managed two pumps, as instructed.

The last step was the cuffs: leather, adjustable, soft enough to avoid marks but sturdy enough that escape was impossible. He attached each one to the bed frame, then rehearsed what would happen when Steph walked in--her slow inspection, the inevitable barrage of photos and ridicule, the eventual unlocking and maybe, god, the orgasm.

He was sweating when he heard the apartment door open. Steph had a key, of course. She always did.

He waited, every muscle rigid, as her footsteps echoed down the hall. She entered without knocking, the sound of her heels a gunshot in the hush.

"Look at you," she said. "Perfect little cum dumpster."

He hated her, but the words set him on fire.

She set her purse down and circled the bed, phone already raised. "Smile," she said, and snapped a photo. "God, you're such a slut. I almost feel bad for you."

She pressed a finger to the cage, inspecting the way it pressed against the fabric. "You've been good? No cheating?"

He shook his head. "I swear."

She ran a nail over the seam of the plug, pressing gently. He gasped. "Still in?"

"Yes," he said, voice hoarse.

She leaned in, smelling of oranges and ozone. "Do you want to cum, Andrew?"

He closed his eyes, nodding.

She pressed her lips to his ear, whispering: "You'll have to beg."

He was ready to do anything.

* * *

The first ten minutes were photos, all angles and flashes and humiliating asides.

Steph directed him, adjusting the way his hair fell, the way his chest arched, the spread of his legs. "Look desperate," she said, and he didn't have to fake it.

She filmed a short video, holding the phone low. "Say your name," she ordered.

He did.

"Say 'I'm a worthless bimbo whore and I deserve everything Steph does to me.'"

He did that, too.

Only when her camera roll was full did she reach into her purse, extracting a small, pink vibrator.

She held it up, smiling. "Ready for the fun part?"

He tried to nod, but the collar kept him pinned.

Steph knelt on the mattress, inches from his caged cock. She turned on the vibrator, setting it to a low buzz, and traced it along the plastic, the sensation traveling like a lightning strike up his spine. He shuddered, hands straining against the cuffs.

"Sensitive?" she said.

He whimpered, already close.

She increased the setting, pressing the tip directly to the head of the cage. "You're going to cum so hard you cry," she said, matter-of-fact.

The stimulation was merciless. Every nerve ending lit up, every circuit in his brain focused on the point of contact. He bucked, but the restraints held. Steph switched to patterns, rolling the vibrator in circles, sometimes pulling away just as the tension crested.

Andrew was panting, babbling half-formed pleas. "Please, please, oh my god, please--"

Steph slowed the vibrator, letting him hover at the edge. "If you want to cum, you have to ask permission. Every time."

He did, over and over, the desperation ratcheting with each denial.

She left him at the brink for what felt like hours, switching hands, pausing only to record another video or to remind him how pathetic he looked. His face was streaked with sweat and tears; his makeup ran, lips smeared, a grotesque parody of the girl she'd made him into.

He wasn't sure how long it went on--time had become an abstract, measured only by the rise and fall of hope, the ache of his cock, the pressure in his ass as Steph occasionally squeezed the bulb for extra effect.

Finally, she relented, pulling the key from her purse.

She held it up, twirling. "You know, I could make you stay like this forever."

He begged, wordless now.

Steph crouched, unlocked the cage, and let his cock spring free. It was red, angry, and leaking. She stroked it twice, maybe three times, and Andrew exploded--shot after shot, the orgasm so intense he screamed.

Steph filmed it, of course.

She wiped him clean, then kissed his forehead. "Good girl," she said.

He lay there, limp, every muscle vibrating with aftershock.

She dressed, checked her hair in the mirror, and before leaving, she turned to him.

"Same time next week," she said.

The door closed, and for the first time in three weeks, the apartment was silent.

The cage, still unlocked, dangled from his waist.

Andrew wondered if he would ever be the one to close it again.

* * *

Andrew spent the morning after his release curled in bed, blanketed by fatigue and the oily residue of having come so violently, so pitifully, that the memory made his cheeks prickle with heat. The unlocked cage lay on the nightstand, an artifact, while the plug--mercifully, finally--had been set aside in the bathroom sink, awaiting its next commission. He lay there for a long time, unmoving, waiting for the blood to retreat from his face and the ache in his legs to become something less than Biblical.

He had imagined that post-orgasmic clarity would hit like a cold snap, freezing the fever out of his brain and letting him return to the normalcy of spreadsheets and emails. Instead, it was like waking from a dream only to realize the nightmare was in the waking world: Steph's voice had nested inside his skull, and every memory of the previous night spun through his head in bright, merciless detail. He didn't dare check his phone. He already knew what would be waiting.

He found the first message before noon.

It was a photo: himself, mouth agape, eyes wet, as Steph's hand blurred in the frame. Below, the caption: "Getting better at taking orders. Still needs work on holding it." He felt his stomach drop, and then twist, because despite everything--despite the mortifying certainty that the photo would never truly be deleted--his first reaction was a dull pulse of pride.

There were six more messages in the thread. Most were videos, some less than ten seconds. One was just a still, the vibrator pressed to his bulge, the panties damp and translucent. The last was a text: "We're doing round 2 tonight. Be ready by 8. You know the drill."

He didn't. But he would.

* * *

There is a taxonomy of humiliation, and Steph was a master of classification. The second session was the same as the first in only the broadest outline. She arrived on time, nails painted a new shade of venom, her hair back in a high, martial ponytail. She wore leather shorts, a ribbed tank, and a blazer; the look was "feminist CEO, but meaner." He opened the door in wig, makeup, and the black bralette she had gifted him at the mall. He had tried to do better with the eyeliner, but it still looked like he'd lost a fight with a raccoon.

Steph didn't bother with pleasantries. She marched him to the bedroom and instructed him to strip to the lingerie, then re-fit the plug. "You'll want to lube it this time," she said, in the tone of someone warning about black ice.

She produced a camera--an actual DSLR, not her phone--and set it up on a tripod at the foot of the bed. "We're going to document your progress," she said. "For science."

He crawled onto the sheets, laid out as before, and offered his wrists for the cuffs. He had not, until this moment, considered that Steph might bring props. She attached a spreader bar to his ankles, locking them wide, then laced a collar tight around his neck, fixing it to a ring in the headboard. He was less "willing participant" now and more "evidence bagged for storage."

She started the camera. The red light blinked.

Steph circled him, tapping the plug with a knuckle. "Last time, you came too fast," she said, as if discussing the weather. "That's not acceptable. Tonight, we're going to see how long you can hold out."

He tried to answer, but the collar was tight and he could only croak.

She produced the vibrator, which was larger than last time, industrial in design. She powered it on, the hum filling the room. Andrew braced himself, but Steph, ever inventive, pressed the tip not to his cock, but to the base of the plug.

The sensation was immediate and catastrophic. He gasped, back arching, as the vibrations traveled through his body in a perfect, continuous loop. Steph adjusted the setting, cycling through patterns until she found one that made him tremble uncontrollably.

"Look at you," she said, voice flat with admiration. "Not even five minutes in and you're ready to break."

He wasn't. But he wanted to.

She alternated between the plug and the cage, teasing at the edges of pain and pleasure, never allowing him to settle into a rhythm. When he began to buck, she pressed the spreader bar flat to the mattress with her knee, pinning him. "Do you remember what I said about asking permission?" she asked, voice sharp.

He nodded, sweat rolling into his eyes.

"Then do it."

He tried to speak, but the pressure in his groin was overwhelming. It was a wave, cresting and breaking and building again, an infinite loop of almosts.

"Please," he managed. "Please, Steph, let me cum."

She held the vibrator steady, eyes never leaving his face. "You don't deserve it," she said.

He whimpered. "Please, I'll do anything--"

Steph let the vibrator drop, then leaned in close, lips brushing his ear. "You'll have to prove it," she said. "Tonight, you're going to earn it."

She reached into her purse and withdrew a second, smaller plug. "We're going to see if you can handle both."

He balked, twisting in the restraints, but Steph was implacable. She slicked the smaller plug, and without ceremony, pressed it against his already-stretched hole.

It hurt, but not in a way that was unfamiliar. He grunted, eyes watering, but Steph worked with steady, relentless pressure. When the plug popped inside, he gasped.

She returned to the vibrator, this time alternating between the two plugs, each stroke of the device sending fresh waves of sensation through him. He screamed--he had not known he could scream like that--and Steph, delighted, turned the camera for a close-up.

"You're doing so well," she said. "But I think we need more motivation."

She grabbed her phone, set it to record, and pointed it at his face.

"Tell me what you are," she said.

He hesitated, but only for a moment. "I'm a worthless bimbo whore," he said, voice high and ragged.

"And what do you deserve?"

"Anything you want to do to me. Please, Steph. Please."

She smiled, a real smile, and pressed the vibrator hard against the base of his cock. He bucked, a spasm running through his whole body, and felt a trickle of precum leak onto the sheets.

"Do you want to cum?" she asked.

"Yes. Yes, please, I'll do anything--"

She cut him off, her voice turning cold. "Even beg Derek for it?"

He froze. The thought of Derek--the Adonis from the stairwell, the boy who had seen him at his lowest and still grinned--made his stomach drop.

Steph pressed the vibrator to the cage again, ramped to maximum. "You can cum," she said, "if you send Derek a video of yourself, begging him to join us next time."

He whimpered. "No--please, not him--"

She let the vibrator fall away. The loss was immediate, a cliff-edge. He thrashed, desperate for the sensation to return, but Steph just waited, arms folded.

"Say yes or we're done," she said.

He thought of the last three weeks, the endless teasing, the mornings spent leaking into panties he couldn't remove, the phantom weight of Steph's words in his head. He thought of Derek, the way he'd looked at him at the mailbox, the way his touch on Andrew's shoulder had been firm, not cruel.

He nodded, once, and Steph grinned.

She brought the vibrator back, and this time, she did not stop.

The orgasm came in waves--long, shuddering, animal. He screamed again, this time into the sheets, the sound muffled by shame and relief and the wild, electric need to please. Steph filmed the whole thing, laughing softly.

When it was done, when his body was slack and the plugs were mercifully removed, she uncuffed his wrists and let him lie there, face pressed to the mattress.

She leaned down, brushing his hair back with a tenderness that made him want to cry. "Good girl," she said. "I'm proud of you."

He wanted to thank her, but all he could do was whimper.

She dressed, packed the toys into a tote, and before leaving, set her phone on the pillow beside him.

"You have thirty minutes to send Derek that video," she said. "If you don't, I'll do it myself. And you know I'll make it worse."

The door closed. The apartment, again, was silent.

Andrew stared at the phone for a long time.

He opened the camera, hands shaking, and pressed Record.

The rest of his life began with the words: "Hey, Derek. It's Andrew. I need your help..."

* * *

He sent the video before he could talk himself out of it. He waited, stomach rolling, for the reply.

It came an hour later.

A single line: "You're a legend, man. Tell me when and where."

He laughed, a wild, bitter sound, and rolled onto his back, feeling the ghost of the pluand the throb in his ass.

He wondered, not for the first time, not only how far Steph would push him but how far he would allow her.