Taylor had always been a good boy on the surface. At 30 years old, with a decent corporate job in Boston, short brown hair, and an average build, he looked like any other guy on the T. But inside, he was burning. He craved to be a brainless himbo sissy chastity fag: locked, pretty, and completely controlled. The fantasy consumed him: the tight steel cage denying his cock for months, the constant soft caress of panties and a bra under his boring button-downs, the humiliating rush of being exposed as the desperate little slut he really was.
He’d tried doing it alone. The longest he’d ever made it was 30 days before the ache in his balls and the voice in his head whispering “just one stroke” won out. He needed more. He needed someone to make him.
One Friday night, he wandered into a dimly lit gay bar in Boston. The place was packed with leather daddies, twinks, and everything in between. Taylor was sipping a Truly when he noticed Alex.
Alex was tall, broad-shouldered, with sharp cheekbones, a trimmed beard, and the calm, predatory confidence of a man who got what he wanted. Their eyes met. An entire conversation transpired with their eyes alone. A better conversation took place on Recon. Within an hour they were back at Alex’s apartment in Back Bay, Taylor on his knees with Alex’s thick cock down his throat.
After Taylor swallowed every drop and was lying spent on the floor, he confessed everything in a shaky, horny whisper. The chastity obsession. The sissy cravings. The blackmail fantasy. How he wanted to be trapped.
Alex listened with a slow, dangerous smile, having looked over Taylors profile before.
The next morning, still sore and leaking in his ruined underwear, Taylor recorded the video.
He was naked on his back in his own bedroom, chastity cage ring already in place but still unlocked. His small cock twitched as he stared into the camera with his legs in the air.
“My name is Taylor. I’m 30 years old. I am consenting to Alex owning me for the next 90 days. I want him to blackmail me. I want him to keep me locked. I want to be forced to wear panties and a bra 24/7. I want to be turned into a himbo sissy chastity fag. I give him full rights to use these photos and videos if I disobey. He can contact my friends and employer if I don’t obey him. This is completely consensual. I want this.”
He locked the cage with a loud click, sealed the keys in an envelope, and sent the video to Alex.
Alex responded within minutes.
Alex: Good girl. The contract is ready. Sign it and send it back. Then we begin.
The terms were strict:
- 90 days of continuous chastity. No unlocking whatsoever. No orgasms. Only ruined edges if Alex allowed them.
- Panties and bra 24/7 under all boy clothes. Feminine underwear only.
- Gym 5 times per week, minimum 500 kcal burned each session. Alex would monitor via shared location and photos.
- Once per week, Taylor had to leave the house in a full maid outfit: stockings, heels, frilly dress, wig, makeup, and stay outside for at least 10 minutes. Anywhere. Anytime. Proof required. Sometimes he’d do it alone, sometimes Alex would accompany him.
Taylor’s hands trembled with fear and arousal as he signed the digital contract and sent it.
Alex: Perfect. Your blackmail material is now in my permanent possession, sissy. Send the keys. Your 90 days start now.
Day 1
Taylor stood in front of his mirror in a pink lace thong and matching bra under his work shirt and slacks. The cage was already starting to feel tighter. His nipples rubbed against the bra cups with every movement. He was terrified and dripping.
He went to the gym that night and burned 620 kcal, sending Alex the proof. That evening he received his first task: “Send me a photo of you in the maid outfit in your living room. Practice walking in heels. You’ll be outside in it soon.”
Week 3
The constant lingerie had become his new normal. The soft lace against his skin made him leak constantly into the cage. His ass had started rounding out nicely from the relentless squats and hip thrusts at the gym. Alex made him send daily ass photos.
The first public maid outing was on a cloudy Tuesday. Taylor’s heart pounded as he stepped out of his apartment building in Boston wearing a black and white maid dress that barely covered his caged clit, thigh-high stockings, and 4-inch heels. He walked two blocks to a quiet side street, shaking, face burning with shame and arousal. A few cars passed. One driver did a double take and honked. Taylor wanted to die and cum at the same time.
He sent the timestamped video to Alex.
Alex: Good girl. You’re really mine now.
Week 7
Taylor’s mind was melting. The cage was a permanent part of him. His cock had shrunk and his balls ached constantly with denied need. He caught himself thinking in simpler, sluttier ways: giggling at dumb jokes, craving cock, obsessing over how pretty he could make himself.
He was up to wearing full makeup under his boy clothes some days. The gym had transformed his body: rounder ass, thinner waist, smoother skin from the constant moisturizing Alex demanded. People were starting to notice something different about him.
The weekly maid walks had become ritualistic humiliation. One time he did it at a busy park in Boston. Another time he walked around the block near a construction site, the workers catcalling the “sexy maid.” Each time he came home, he humped his pillow desperately, the cage clattering uselessly.
Day 85
Taylor was a changed guy. His reflection showed a soft, curvy, empty-headed sissy with a locked clit and a desperate craving to please. Alex had been sending him tasks almost daily: edging without cumming, writing “I am a chastity fag” 100 times, practicing deepthroat on a dildo while wearing the maid outfit.
The blackmail folder had grown massive: hundreds of photos and videos of Taylor dressed up, caged, leaking, walking in public, and begging.
One night Alex called him.
“You’ve done well, Taylor. Only five days left. But I’ve decided something… I don’t think 90 days is enough for a pathetic little himbo like you.”
Taylor whimpered into the phone, his caged cock straining as hard as it could.
“Yes, Sir… whatever you want.”
The 90 days ended, but the cage stayed on. The panties and bras never came off. The weekly maid walks continued.
Taylor had finally become exactly what he always secretly wanted to be… A fully owned, blackmailed, himbo sissy chastity fag…and he had never been happier.