His secretaries always put up with his shit. Always. They put up with the leering and the inappropriate comments. They put up with his thinly veiled, rampant pornography use. The covered for his “appointments” with beautiful escorts who visited his office during business hours. They always put up with this because they were paid well, and the work load, other then covering for his sexual deviances, was light.
But Miss Strange was different. She was tall, busty with flaming red hair and pale skin, just as many of his previous secretaries had been, including the one she was replacing. But when he made the comment about her melons, she looked him in the eye and asked “Is that appropriate workplace behavior? It’s not even a witty line.”
Her direct reply took the fun out of it. He liked to watch them turn and blush. He retired to his office to answer email and phone calls. It wasn’t long before he was distracted by a naughty email from one of his favorite escorts. A visit from her would be a welcome distraction, so immediately replied that yes, he would love to see her that afternoon.
Miss Strange announced her arrival and offered the two of them coffee. He smiled and made a smart ass remark about Lola having everything he needed as he smacked his friend on the ass and closed the door in Miss Strange’s face. The sound of muffled giggles followed – as well as the muffled sound of something entirely not work related.
Miss Strange returned to her desk to work. She looked on silently when he walked Lola passed her to the elevator an hour later. Every day that week, another escort would show up, followed by giggles and muffled moaning. By the end of the week, Miss Strange didn’t even look up from her desk when he walked them out. She just smiled knowingly.
He thought that perhaps now Miss Strange understood how things worked around here. He thought that perhaps now Miss Strange would realize that her real job, was to stand between him and his good time, and upper management.
He was wrong.
He returned to his office, leaving the door cracked and returned to business. A short while later Miss Strange entered his office and shut the door behind her. “I supposed you expect me to perform those duties as well?” she said as she looked him dead in the eye while starting to unbutton her matronly top. Her ample cleavage spilled out and she adjusted it for maximum effect.
He paused. He was always careful to steer clear of the secretaries, preferring to bully them and make them blush, but perhaps, just this once?
She walked to his desk, leaned over it, so close he could smell her sensual vanilla perfume. “I see the way you look at me. I’ve also seen your call records. And you know I have access to your email. I see how many women you are juggling. You’re a naughty boy aren’t you.”
He could feel his cock start to swell. “Yes. I am a naughty boy. I’d love to show you how naughty. I could make you feel pleasure you’ve never felt before. I could take my cock and …”
“Why don’t you show me that cock? Can you get it nice and hard? Tell me how you would please me with it.” she said as she walked around the desk and perched on the edge in front of him so that her skirt, already dangerously short, rode up even further.
She giggled as he fumbled to get his pants down as quickly as possible, He looked ridiculously hopeful. Did he have any idea of what he was getting into? Obviously not.
He started to go on, in great detail and while stroking furiously, about how he would fill her wet pussy with his giant cock. He stood up, letting his pants fall to his ankles and reached for her. She laughed and stepped back. He tried to take a step towards her but was hampered by the pants around his ankles.
“You know you look ridiculous, right?” She said as she stepped back even further.
“What?” He said still stroking his cock.
“I said. You know you look ridiculous. Right? Also. You know that I have a nanny cam in here.” she points to a small device on a shelf across from his desk. “I put it in here after my first day. It’s been recording everything that happens on your desk and couch. You have made quit a few interesting videos. Stuff I’m sure my friend in human resources will love.”
The blood drained from both heads.
“You bitch! Get the fuck out of my office! You’re fired! You are so fucking fired. Fuck you and your friend in human resources!”
“Are you sure you want to do that?”
He pulls his pants up angrily, ripping the camera from the shelf pulling the wire out of the wall.
“I’m not letting this shit out there. I’m going to destroy this camera.” he says and he throws it to the ground and starts stomping on it.
“Oh, you poor little man. Do you really think that camera had the video on it? Silly boy. Everything that has been recorded has been uploaded to my hard drive at home. My hard drive is backup up to the cloud nightly. It’s technology fun?”
He stands in stunned silence. The gravity of the situation taking hold. “I’m… I… I would never really fire you. You can keep your job. I’m sorry. I’ll clean up my act. I’ll stop seeing escorts here. Just… don’t show anyone that video.”
She smiles. She steps towards him. “Now I think we can come to an agreement. Sit down.” He starts walking back to his desk. “No! Not at your desk. On the floor. At my feet.”
He stands and stares at her.
“If you are going to have a problem following that simple command, there is no way you can follow more more… detailed… requests. I’ve no interest in dealing with someone who can’t follow basic direction.”
“I’m sorry! No. Sitting. See!” He says as he drops to a seated position at her feet. “What kind of more detailed requests?”
“First. I’m going to need you to wear this chastity device.” she says as she hands him a pale pink Holy Trainer. He takes it and examine it. “You will need to text me pictures whenever I request, night or day, to prove that it is still on and intact. I will also examine it weekly so signs of tampering. In the future, your assignments will get more… complicated, but let’s get you accustomed to this first.”
“I wear this… on my cock? It’s not going to fit!”
“Your cock is not nearly as big as you think it is.”
“But what if I have a date? Or want to, you know… pleasure myself.”
“You won’t have any dates. And I’m in control of when, and if you are allowed to pleasure yourself.”
“How will I sleep in it? Pee with it?”
“You will get used to it. And you will get used to sitting when you pee. It will be good for you. I’m going to leave you in the office to put it on. The last thing I want to do is touch that shriveled cock. I’ll be back in five minutes. I expect you to be kneeling right there and naked except for that cock cage.”
“But I don’t know how to put it on!” He shouts after her as she walks to the office door.
“You will figure it out.” she says over her shoulder as she shuts the door.
To be continued….