Boardroom Bill Goes to an Interview

Chores

Ms. Sanguine once again patted the cage now imprisoning Bill's cock. Removing the latex gloves, she asked, "There, how does that feel?", and looked at him expectantly.

"It's uncomfortable, but it reminds me of your control over me. The discomfort only makes me feel more submissive to you, which excites me and leads to further discomfort", he answered while unconsciously thrusting his hips slightly up and down in the chair.

"Stop your humping. When I want you to act like a dog, I'll tell you", she admonished, while she briefly turned away to suppress a giggle and regain her composure.

"Yes Miss", Bill answered while willing his backside to remain planted in the chair.

When Ms. Sanguine turned back to Bill, she had a frighteningly serious look on her face. Grasping Bill's exposed balls in her hand, she hissed, "Yes who?"

Bill winced at the pain she was causing to his tender testicles, even though she was barely squeezing them. "Yes, Miss Sanguine. I'm sorry, Ms. Sanguine."

"Good worm", she said before giving his balls a slap. "I'm going to release you... from the table", she said with a devilish grin, "and I want you to scurry on to the back wall where you'll find a small closet with some cleaning supplies. I want my floors scrubbed. I have more important things than you to attend to. My assistant will make sure that you don't lollygag." With that, she expertly unbound him from the chair and strode away without a look back.

Bill climbed down from the chair and made his way to the back of the room. The idea of cleaning Ms. Sanguine's throne room while naked and in chastity sent a charge of excitement through Bill's body. The problem was, he had never touched a mop in his life. He had seen one in use on occasions when he worked late and the cleaning service was in the office. He would have to figure it out. He hoped he could do well enough to please her.

As he opened the discrete door of the closet and peered inside, his concern about learning to use a mop evaporated. Instead of a mop, he found a few scrub brushes, a bucket, some cleaning solution, a vacuum, and a spigot mounted to the back wall. It seemed that he would be spending plenty of time on his hands and knees. The worst part of which was that he would be doing so with only his own company. There would be no chiding from Ms. Sanguine or disciplinary smacks to correct his deficiencies. Resigned, he placed the bucket under the spigot and began to fill it.

After about 15 minutes of scrubbing, Bill's knees began to feel sore. He hadn't even cleaned a quarter of the floor, and the thrill of serving naked and in chastity had begun to fade. Bill wondered if this is what he really wanted to be doing. Nevertheless, he continued scrubbing his way toward the back of the room.

A while later, he heard footsteps approaching from behind, across the floor he had just dutifully scrubbed. It wasn't the delicate yet sinister clack of heels. Instead, the sound was heavier. He did not dare look up from his work, and continued scrubbing, hoping that whoever was coming didn't make a mess of his floor.

"Keep scrubbing, slut", he heard a familiar voice command. He instantly recognized it to be that of the receptionist. He felt the weight of a foot, clad in something with thick soles from what he could tell by its touch on his skin, press down on his ass.

"My, aren't you pathetic? On your hands and knees, scrubbing the floor of a mistress who didn't even hang around to entertain herself by watching," the receptionist said.

Bill felt the weight on his ass shift then a hand on the cage he wore.

Laughter echoed off the walls of the room, and the woman continued, "That didn't take long. Already locked up. Are you frustrated yet? Ms. Sanguine has been known to keep her pets like this for weeks", she said, shaking his caged cock back and forth. "I feel like there's something missing here though. I'm Lilith, by the way. You may address me as Ms.Lilith or Ms. Keep scrubbing."

Bill heard Lilith walk away and then return, this time standing in front of him. Bill had been so single-mindedly focused on Ms. Sanguine, and to be honest, too nervous to really take stock of her until now. Her raven hair, black lipstick, and heavily-linered eyes were striking against her pale, flawless skin. She had changed out of her outfit of leather straps, and was now wearing a black t-shirt and a pair of jeans that hugged closely to the curve of her hips. A pair of thick-soled leather boots poked out from the slightly flared bottoms of her jeans. Bill thought they might be Doc Martens. In her hand was something that Bill recognized but wasn't entirely happy to see, given the task laid before him.

"Oh I see you recognize a humbler when you see one. It's one of my favorite toys of all", Lilith said in a tone that was somehow simultaneously foreboding and gleeful. "Do you mind wearing it for me while you scrub the floor? I promise if it becomes unbearable, I'll take it off. What do you say? Please?", she asked while theatrically batting her long black eyelashes at Bill.

Bill wondered to himself just how many more things could be placed on his genitals. Then he remembered some of his purchases and quickly shoved the thought away.

"Yes, Ms. Lilith, I will wear the humbler for you", he said.

Lilith stepped around to Bill's backside and unceremoniously grabbed his balls, pulling them out past the back of his thighs. With an almost childish giggle, she clamped the wood around his ball sack above his balls and just below the ring from his chastity cage. The wooden device extended on both sides of his balls and rested against the backs of his thighs. With the click of a latch and the use of a simple toy, Lilith had taken away Bill's ability to stand up straight without extreme pain to his already swollen and sore balls.

Bill reckoned that this new development didn't really matter, since he still had a lot of time ahead of him on his hands and knees. Besides, he felt himself growing sexually aroused again, at least mentally. The cage limited anything more.

Lilith poked Bill's captive testicles with the toe of her boot and made a content sighing sound. "You're not scrubbing. Get to work", she said before again walking away.

She returned shortly with a simple chair like one would find in a break room and sat it down next to Bill, who was feverishly trying to complete his chore. Sitting down in the chair, Lilith rested her boots on Bill's back, her legs crossed at the ankles.

"Oh, I should have brought some wine", she said, before lightly tapping Bill's balls with a crop she had retrieved when she got the chair. "I hope Stacy takes her time."