“FUCK, Fuck, FUCK!” Bret yelled as he hung up the phone.
The Plant account had pulled out. It was his last chance of meeting sales goals for the month. He knew what would happen at this point. His boss Damien put poor performers in “time out” at the end of the month. Rarely did anyone slip this far behind, but Bret had been off his game for a while now.
Within the hour he was called into Damien’s office. Bret couldn’t believe the punishment he was about to endure. As he sat down across from Damien’s desk he couldn’t help but seethe with rage when he saw the sly, insolent, smile on his face.
“It’s best we just get to it Bret,” he said “take off your pants and your underwear.”
From his desk drawer he pulled out a long case and opened the lid. Inside, was a line of male chastity cages. High-end, indestructible, black plastic ones. He knew just the one he needed. Every new hire under him had their cocks sized lest they needed punishment at a later date. Poor Bret sized to one of the smallest cages with his tiny four-inch hard, one and a half inch soft white boy cock.
Bret’s face turned beet red as he slid off his shoes and pulled off the bottom half of his suit.
Damien walked around from the back of his desk with the cage and it’s key in hand.
“Look me in the eye cucky,” he said to Bret, “this is going to stay on until your performance improves. Your sales numbers have long been pathetic. You need to refocus and work on pleasing your boss, not worry about getting that little cock off. You’ve lost the privilege to be on the sales floor. You’ll be heading to the filing room everyday working on the projects I give to you.”
With that Damien reached down and slid the cages’ ring around Bret’s balls and cock head, slipped the cage on, and quickly locked it and pocketed the key.
“Get your shoes back on cucky, you don’t deserve pants anymore.”
Bret was near tears as he put his shoes back on. He couldn’t believe he stooped to this level. All thought-out his prep-school, Ivy League education he had been primed for a high power job like this. When he started out he was cocky. He couldn’t imagine a simple little sales job like this could be that hard. It turns out after a life of getting everything for free, having to work for something was a struggle. He was just barely hanging on for a long time but that all came crashing down in the past month as some accounts pulled and he couldn’t get any new clients. It was clear he couldn’t perform to any reasonable standard.
Damien couldn’t help but laugh a bit. He loved seeing these arrogant white boys put in their place. It had been a long time coming for him and he had to work for everything he had. As a disadvantaged African American male everything was an uphill battle, especially twenty years ago when he started out. He had to fight even for an interview at the company and then fight even harder to show he had earned his place there. They preppy white boys who just waltzed their way in made his blood boil and he loved it when they finally got a wake up call.
“You’ll be working on reorganizing the reports starting from 2018 and working into the present. You won’t get your pants back or the cage off until you prove your worth to the company. Get out of my office.”
Bret turned around and cupped his hands around his caged dick ready to head to the file room. “None of that Bret,” he heard from behind him. “You earned this punishment, take it like a man.” From behind Damien raised his hand and delivered a hard slap on Bret’s ass that left a bright red mark.
With that he placed his hands awkwardly at his sides and headed out.
As he walked down the office halls everyone stared and giggled in disbelief. In the back of their heads they all knew this might happen, they remembered getting their dicks sized for a cage when they started working, but actually seeing it was another story.
Bret stared at the floor beet red. He shuffled his way to the file room as everyone stared at him looking ridiculous with nothing on but his suit jacket, shirt, and loafers with his tiny caged cock and milky white ass on display for everyone to see. Damien’s hand-print was the final straw that sent everyone over the edge and they started roaring with laughter. The door to the file room slammed behind Bret and the sign over the door which read “TIME-OUT ROOM,” as a warning shook.
Bret immediately got to work on the files, it was going to be a long night.
***LATER THAT EVENING***
Damien was outside Bret and his girlfriend Caitlyn’s apartment. He had pre scheduled this meeting to discuss what it would be like with her boyfriend in a cage for a while. Caitlyn honestly didn’t mind the idea, at least it would but his annoying pestering for blow jobs and what not to an end. She was honestly tired of his little dick.
As she got into Damien’s BMW the events that would occur that night were immediately solidified. After dinner Damien would “drive her home” while Caitlyn used every trick in the book to get him to sleep with her. Over dinner they’d discuss Bret’s flaws, kiss tiny dick, his lazy attitude, and his poor performance. Caitlyn would slowly be seduced by Damien. The older more mature man with his salt and pepper hair and handsome face could offer so much more than Bret. The massive bulge in his pants proved this.
It didn’t take much but Caitlyn finally let her defenses down and reached over and grabbed Damien’s cock through his pants. He just looked over at her and said “suck it.” After they pulled into his garage Damien didn’t even wait to kick into gear. I bent her over and fucked Caitlyn over the hood of the car. His big black cock was the best she’d ever had and Caitlyn immediately began orgasming while he fucked her. After the best fuck of her life, Damien slowed his pace and shot a load deep into Caitlyn’s pussy.
Within minutes he called her an Uber and they said their goodbyes. It was clear this would be the first of a long string of fuckings during Bret’s tenure in the cage.
After she got home and reminisced about the evening. Despite how late it was, Bret was just getting home. He made sure to leave long after everyone else in the building had left and made a mad dash to his car in the parking lot still without pants.
When Caitlyn saw him like that, locked up in his little cage with his work clothes still half on she couldn’t help but scream and laugh. She motioned him to come to the bed and gestured that he eat her pussy.
It didn’t take long for Bret to feel Damien’s cum, taste it, but he was too tired to put up a fight. Caitlyn’s pussy was destroyed. Stretched out, red, and dripping with cum. Bret just accepted and swallowed his fate. To his dismay his tiny cock began to strain in his cage.
After Caitlyn orgasamd for the last time that night they both laid down and went to bed. This was the beginning of a long journey for them.
End.