Boardroom Bill Goes to an Interview

Free From Shame

Bill woke the next morning  once again confused about how or even if to pursue his sexual fantasies. He felt like trying to abandon them completely was disingenuous and likely doomed to failure. However, the prospect of ever finding the type of relationship he desired was looking less likely. At least that's how it seemed to him. Maybe he would try out the club Lilith had taken him to before giving up all hope. One thing was certain. He was done with chastity devices. He might reconsider his position if he ever found himself in a relationship where both parties appreciated the gesture, but for now at least, he was over it.

Later that afternoon, it was off and he was free of that particular shame. He didn't see Miss Sanguine, as she was "busy" again. He was more than happy to let Lilith do the "honors". He would probably let a hobo take the thing off of him if the hobo had a key that fit.

"I would have done this yesterday", Lilith said as she pulled the cage off as gently as possible. The urethral insert had long lost its lubrication, and it stung a bit. "You were drunk and I wanted to be sure that it was really what you wanted cause it sounded like you were wanting to end more than just your chastity. "

Bill winced as the small stainless tube finally exited his penis. He came to the conclusion that wearing such a device for as long as he did could not be healthy. "Yeah. You're right about that, Lilith. I'm looking for more than to just scrub the floors while my dom disappears and does...what the fuck ever she was doing all that time. I mean scrubbing the floors under her watchful eye could be fun, but I could have saved some money and scrubbed floors at home and gotten just as much of a thrill as doing it alone here."

Bill immediately realized that in expressing his disappointment at the session with Miss Sanguine, he had probably sounded ungrateful for the time Lilith had spent with him. He opened his mouth to perform some damage control, but she cut him off.

"It's interesting how you recall that evening's events. You seemed quite happy while you were kissing my boots, Bill", she said pointing the cage at him like an accusing finger.

"You're right, I'm sorry for sounding unappreciative. I am grateful for your time and conversation, but I'm also so very frustrated and a little jaded over my first foray into femdom", Bill said, hanging his head. "I shouldn't even be laying this at your feet because my issue isn't with you. You've been more than gracious."

Suddenly, Bill was struck with inspiration. "Would you allow me to apologize correctly, Miss Lilith?"

Lilith rolled her eyes and shoved the cage into Bill's hands. "Unbelievable. Let me guess. You want to kiss my shoes and beg for forgiveness?"

Bill frowned and cut his eyes to the side.

"Get out of here, you disgusting pervert. Your apology sounds especially hollow now. You are a lowdown maggot. You don't deserve to be in my presence. You belong at the bottom of a landfill, burrowing your way through the things that are discarded by real human beings", Lilith hissed through sneering lips.

Bill began to shuffle toward the door, cowering and dodging as if her words were projectiles. He was able to only mutter additional apologies as he tried to turtle his head down between his shoulders. Her words stung him but they made his cock stiffen. It was such wonderful degradation. He only wished it was part of a play scene rather than his cue to retreat.

As Bill slinked his way out of the frosted glass door, Lilith chuckled to herself.

Later that evening, Bill's wounded pride had healed enough that he felt up for a drink. Maybe it was the part that was still wounded that made him thirsty, but he didn't bother to ponder that matter much.

He called for a cab and told the driver to take him to the Eden Club. He wondered if he would see Lilith there, and dreaded how awkward that would be. He answered some work emails during the drive, and then spent a little time just trying to clear his head.

Bill made his way to the bar, scanning the room for Lilith, and was simultaneously relieved and disappointed when he didn't see her. He sat down and leaned his elbows onto the brass rail that bordered the mahogany bar, and waited for the bartender.

Bill sat listening to Lady Gaga's "Teeth" playing softly in the background as he sipped on his third glass of Scotch. He had drifted off into a world of his own, listening to the music and waiting for the first signs that the Scotch had started working when he felt a hand on his shoulder and a vaguely familiar voice speaking his name.

He turned and was shocked to see Kate, who was a mid-level manager in the accounting department of his corporation. He had only seen her once or twice when she was presenting budget numbers at some project meetings, but he remembered her because he found her to be attractive. At those meetings, her attire was very conservative, and she wore only a modicum of makeup. The few times he saw her, she wore her auburn hair in a bun or some other dry style that Bill didn't find exactly appealing. She pulled it off though with her confident demeanor and natural beauty.

She looked a bit different now. Her makeup, while still tasteful, accentuated her green eyes, and her lipstick was a dark plum that was almost black in the dim light. Her hair cascaded down to her shoulders, and she wore a pair of tight jeans and a black Danzig tee shirt. A pair of what looked to Bill to be black combat boots rounded out her attire. When he saw the miniature handcuffs dangling from her ears, he began to worry that she knew exactly what kind of club she had found him in.

"Bill, what a pleasant surprise. I didn't know you came here", she said as a knowing grin grew on her dark lips. Dark, sexy lips, Bill thought.

"Well, uh, Katherine from accounting, right?" He waited for her affirmation then went on, "I actually.. this is my first time here." Bill's ears began to burn. Despite all the lies and skullduggery he had to commit in the name of business, he felt uncomfortable lying to her for some reason.

As he tried to hide his discomfort by taking a drink, the waiter from his last visit to the establishment happened by. "Hey Kate! Bill", he said as he hurriedly made his way to the Kitchen.

Bill swallowed hard and cut his eyes toward Kate, wondering if she had caught his lie. Her raised eyebrow and pursed lips said that she had. He closed his eyes and waited for the admonishment he knew was coming.

Instead, he heard Kate guffaw. "Oh, Bill. Don't be embarrassed. It's fine. I'm just surprised to see you're not so one dimensional as people at the office say."

Bill sat there shocked that she had the nerve to speak so directly with him, given his standing in the company. But then, they weren't at the office, and Bill reckoned that she shouldn't be expected to act formally in her free time. Besides, he was really curious to learn more about her.

"I'm like an onion", he responded with a wink.

"Well maybe we should work on peeling off some of those layers", Kate said leaning close to him and holding eye contact in a way that made Bill want to squirm in his seat.

"I'm afraid I'd just make you cry, Katherine", Bill said, maintaining eye contact. Bill felt his skin tingling, and the thought occurred to him that if this scene was in a cheap romance story, this is where they would embrace in a sloppy tongue duel and hastily go "somewhere less crowded".

The tension was broken by Kate's laughter. "Oh my god, Bill, did you just make a joke?"

Bill raised his glass to her. "Can I buy you a drink, Kate?"