CEO Penitent Man 01

CEO Penitent Man 1

It was a posh restaurant. Very posh and that meant that certain common conventions had to be followed despite her particular personal feelings right now. He was here on her dime and therefore no quarter was going to be given. In fact, the public aspect was going to make the eventual punishment for his indiscretion even sweeter.

Her hand was held out and her face spoke volumes.

Though her face was heavy with makeup and bright red lipstick, there was a very cruel hard glint in her eyes behind the freshly applied mascara and heavily coloured eyelids.

The company delivery driver was there on her clock and committed to following his boss' decisions and expectations on him tonight due to a problem he had caused at work through arrogance and thinking he knew better than she. This evening was meant to be a way for him to clear the air, and to prove his promise to follow her orders very explicitly in the future.

The first of which was facing him now.

The closest other occupied table was quite some distance away and at this time of night, the ambient lighting had been turned down to create a generally intimate mood for the diners. Despite his natural concerns about the public nature of this moment, there was no one else watching or remotely interested in them.

He looked into her glaring eyes and then down at her thumb, which still held a large droplet of liquid, the white elephant between them. The splash onto her flesh had occurred as she set down a cheap plastic cup to the table before she took her seat.

"Eyes on me!" she almost snarled at him as he nervously glanced left and right, rather than at her proffered hand. "Open!"

There was nothing else for it. He opened his mouth and allowed her to push her thumb onto his tongue. Wiping along it, slightly more ferociously than was strictly necessary, she removed the droplet using his tongue, smiled and then tweaked his cheek to dry herself off. To anyone watching, this was a loving caress; a nice gesture between a couple on a romantic evening out. The reality was that she was asserting her power over him in the most passive aggressive manner possible.

He accepted the indignity without question or complaint; she guessed he knew he deserved it.

The waiter had brought them two wine glasses, an ice bucket and champagne earlier, leaving them with two small measures of drink on the table before leaving them in peace. She plucked her wine glass from the place setting, softly shaking her head to stop him from lifting his own, and drained the contents with one appreciative swallow. Perhaps she needed the alcoholic courage to keep going with her plan.

Keeping her eyes fixed on him, she carefully replaced it on the table, before deliberately and extremely slowly, switching the glasses with her date, the bases smoothly scraping along the white table cloth as they passed each other.

The implication was evident.

Sitting back in her chair, she folded her arms across her half exposed cleavage and crossed one leg over the other. Her eyes tracked down her long legs and regarded her black stiletto heel for a second, before flicking back to watch his reaction. She knew she looked good and despite the overt femininity she was displaying right now, her demeanor suggested that she was not going to be a pushover or even change her mind.

He had nowhere to go.

This was his promise being tested right now and he knew exactly what he was supposed to do.

Quickly glancing around to make sure his actions still weren't the main focus of anyone's attention, he picked up the plastic cup and tipped some of the warmish contents into the now empty champagne flute before replacing it on the table, hiding it now amongst his water and other table decorations.

Trying not to smile at his compliance, she unfolded her arms, picked up her glass, and waited for him to do the same, angling it out towards him.

When he did, she clinked her glass against it in a mock toast and glared at him until he put his to his lips.

They both drank deeply. Hers was, once again, the sharp fruity and fizzy taste of an expensive drink. His was a drink she had produced during her toilet visit and brought back in the little plastic cup.

This was what was expected of him, and she found watching his discomfort actually very erotic. She was in charge and this man was about to learn that in the most publicly naughty, and inventive way, possible. Though he was taller and bigger than she was, and as much as she fancied him, this experience was about putting him firmly in his place. Power was never about size.

The taste was obviously very bitter and the man before her struggled slightly with its pungency.

"Smile as you drink it!" she told him in a low tone, the cruelty in her voice was evident, "or else."

Menacing never needs volume. She was feeling very cruel tonight.

This time he sipped, and though his smile was forced, the fact that he had complied with her instructions actually made her pussy ache for a stroke. She was definitely very wet, a fact that this man was going to find out about later.

Her raised eyebrows made him drain his own drink and offer a cautious smile, wondering if he was pleasing her.

Smiling in return, she leaned forward and offered her glass for him to refill with champagne as a gentleman should for a lady.

It rubbed in the fact that he was drinking an alternative nectar and under some cruel duress. When her glass had been replenished, he tended to his own with the expected liquid. He didn't dare presume he deserved the bottled fizz.

Now they could relax, she decided. It was going to be a fun evening for her to continue as though any other date night, but with him very much completely at her whim. The only real problem she was facing, was the fact that right now she ached to sit on his face and use his nose, mouth and chin to cum. Whether he wanted to or whether he deserved one, was not really her problem. He'd been lucky he wasn't in the toilet when she had filled that cup a few minutes ago, because if he had been, she would have used his tongue to clean her up afterwards.

Making him taste her throughout the meal was only the start of his punishment tonight, and then from now on, he would do as he was told at work too.

The waitress was on the way over towards them, two plates of food in her hands, the look of the over stretched worker on their face.

A nod at his glass, and he smiled happily as instructed before tipping more of her piss into his own mouth as the plates were placed carefully before them, swallowing quickly so as he could thank her, hiding his public humiliation in this contrite act.

Her pussy twitched at his compliance, filling his senses with her in front of another, but at her direction and insistence. She wondered if the waitress could smell his punishment but just as quickly abandoned any care.

So cruel. But empowering.

He would be allowed to eat, but it only took a raised eyebrow to insist on another sip of her in between mouthfuls of food. At this rate, he would need a refill of his plastic reservoir. The way she was knocking back the good stuff though, that was never going to be a problem.

She re-crossed her legs beneath the table and tracked his eyes as her stiletto clad foot flashed out from under the table and back.

He obviously fancied her and was smitten by her legs and choice of footwear. Another evil thought speared through her mind. His trauma was nowhere near over. She had dressed up really nicely tonight and worn her smallest dress. It was only right that he fully appreciated her efforts and showed his reverence as directed.

She skewered a piece of meat and regarded it for a second before fixing him once again with a glare. "Do you see something that you like?" She paused for effect before finishing off with, "Kiss my feet!"

Silence between them. The look on her face meant she was not inviting discussion or any bargaining. She rotated her crossed ankle to incentivise him before putting the meat into her mouth, wondering how he was going to obey.

She would wait.

She could see the mental gymnastics happening in his head as she observed him. His eyes seemed to have taken his soul through the seven stages of acceptance, without saying a single word. There was shock. His eyes widened. No, she couldn't be serious. Not him, a big man like he was. Perhaps later when no one was around? Fuck no. Please. His eyes definitely held a pleading hope. Are you sure? Now he was glancing around for reassurance somehow.

After she was sure he had reached meek docility, she bounced her foot again whilst selecting another tasty morsel from her plate to eat.

Would anyone see and judge him? Think of him in a negative way?

She didn't care either way as she was having fun. If he wanted to keep his job, he had no choice in the matter.

Part of her was more nervous than she was letting on. She wanted to stay reserved and quiet as far as everyone else in the room was concerned, and not draw any negative attention to them, but she wanted... no, needed, to be a cruel bitch towards him.

Would he pretend to drop something and kiss her feet whilst bending down, or did he have a different idea of how to fulfill her instruction?

Is that what she wanted, or would she prefer a little more respect and reverence in the act, rather than a swift peck as his head was on the way past her foot?

She expected a kiss on her flesh at the top of her shoe, but part of her wanted his tongue on the patent leather. Fuck that. She wanted him to be kissing the literal soul of her shoe. After dropping the absolute bollock at work, he should be mouth fucking her stiletto heel.

Moving her foot back out from under the table once more, she conjured the most aloof look she could on her face as though disappointed he hadn't immediately slid from his chair and ended up on hands and knees beneath the table.

Ascertaining that no one was particularly watching them, he shuffled his chair away from the wall towards the middle of the room and sank down off the wooden seat, hopefully disguising what he was doing.

She watched him squat down, and held his eyes until he disappeared beneath the table and slowly kissed her foot, his mouth making contact with the stockings at her open ankle of the foot that was flat on the floor. His mouth tickled slightly.

"And the shoe!"

She knew she was pushing it, though at this point, absolutely no one had turned to look. Now she felt the pressure above her toe, from his face.

"Hmmm."

Job done, he seemed more nervous returning to his seat, scouting out the room to see if anyone was judging him.

Desperately trying not to smile and to maintain her boss bitch persona, she held her glass to encourage another toast.

He had to fill his first, the last of the reservoir in the plastic cup tipped into his cut glass flute. They then (he reluctantly) toasted their night and he once again drank down her pee.

It felt very authoritative to have this reasonably large man, on his hands and knees, at her feet. Compelling somehow. Suddenly, it didn't matter that they were both in public and she found that she wasn't feeling so embarrassed that someone else might see and judge them. She wanted to own her dominatrix role and she needed her face to show that her confidence was developing.

He had done as instructed but somehow she wasn't happy with the outcome. It didn't feel as though he had learned any lesson whatsoever.

She attempted a sneer, though felt her pussy moisten at what she wanted this man to do for her right now, despite the public nature of their location. She wanted to assert her dominance and make him prove his compliance in the most incentive way possible. She should make him stand up and... and...

And what?

Drop his trousers?

Offer his cock to her, right there. Right then?

Turn and be spanked? Bent over and whipped?

There was no getting around the fact that she did really fancy him, and that she fantasised about spreading herself across the table face down and taking him as deep as he could get rather than maintain this alternative persona.

But there were certain issues and factors involved with doing that.

The first was obviously the fact that society didn't take kindly to men exposing themselves in public, regardless of whoever was instructing them to do so. A man deliberately displaying his anatomy was usually associated with a troubled mind and no morals, a very distinctive difference to being made to do it reluctantly, under instruction, as a punishment. Whatever she planned to do has to remain as private as possible but retain an empowering public air.

The second was that she was currently displeased with him after what had happened at work and with the conversation going the way it had, and his meek apology, this was now meant to be her punishment of him. He had to have an appreciable sanction, and one that he would remember forever. The fact that she might remember it too with her hand between her legs was just a happy sidebar.

Thirdly, he had to know his place in the hierarchy of things and the phrase, 'cruel to be kind' was a prevalent thought right now. She needed him to immediately follow orders in the future.

If the tables were turned, and she was being punished for her errors in a similar fashion, there was no doubt in her mind that she would be leaving this restaurant tonight in barely a coat and heels, having been made to strip in the toilets, and her dignity would be the very last thing on his mind with expectations of public lewdness and daring behaviour added into the mix.

Part of her wanted to do exactly that to him. Strip him and take off with his clothes and see if he could make it out of the restaurant and home with only a plastic bag or piece of scavenged cardboard to protect his modesty.

But that wouldn't breed future compliance. That wasn't the way.

There had to be a middle ground. One where there was no chance of him being arrested for public indecency, but on the other he had to prove he would submit to her entirely. Making him kiss her feet and drink her pee during the meal had been a lot of fun for her and she could imagine and just about smell the lingering scent on his lips to hammer home the point, but she needed to send the message that she had complete control over him somehow.

He took another tentative mouthful of his meal, his pleading eyes checking in with her to make sure he was allowed.

She needed to rectify the feeling of insubstantiality she felt after his, hidden against the wall, foot kiss and also get him to the point where he completely obeyed whatever instruction she gave him...

Immediately.

Unquestioningly.

Blindly.

That thought in itself made her feel excited. The natural parameters were that she had to be cautious about witnesses, especially if the goal was instinctive obedience from him. None of this, looking around first to make sure that they were alone, before complying. That wouldn't do. She needed immediacy from him, just as she did for work. Teach this knuckle-head a lesson he wouldn't forget.

Added into her rationale, was also a deep seated desire to see this man panting for her and only her, and if she was honest with herself, a slave to her more intimate desires as well as her work related ones. Well, he was already drinking what she told him to, and dropping to the floor in a sort of timely fashion under instruction. It was extremely erotic to watch him drinking her pee despite what the expression on her face was currently telling him and she had to quell the desire to lift her skirt and press her pussy to his face.

"From now on, you will do exactly what you are told to, within three seconds of me saying it," she purred malevolently across the table to him. "Do you understand?" She punctuated her words with a slight lip curl.

"Y-y-yes." The stammer in return was a good start.

"You will look me in the eyes. You will not look around the room. You will fixate on me, and only me!"

His eyes now widened.

"If you don't, it will only get worse for you!"

This was a something of a lie, and she knew it. Getting as worse as can be for him was already part of her remit. There was obviously the line that she was not prepared to cross for her own protection more than anything else but everything up to that point was open season as far as she was concerned.

He had to believe it though.

He stammered through another affirmative.

"If I tell you to drop your trousers, without hesitation, you look at me and drop your trousers. If I say to close your eyes, you will do exactly that. I do not care who else is around and neither will you."

Fuck. Was that too far to start with?

His eyes almost seemed to glisten. What with? Fear. Arousal. It was hard to tell. Dropping his trousers and closing his eyes would involve a lot of trust on his part. In fairness, that was part of the lesson she was trying to teach him. Still, what did he expect? She wasn't about to teach him to fill in forms on time or how to deliver to customers.

"If I tell you to present yourself, you will stand with your legs apart and your hands clasped behind your back as though to attention." She sipped her own glass of fizz and wished he had more of her pee to drink too. It would only be a few minutes and there would be more than another glass full ready for him. Somehow, after the initial concern of watching him drinking it, she found that it was more of a turn-on than she had previously imagined.

Humbling and humiliating.

His nod was almost imperceptible but it was there.

"No matter, where... we... are!" Her voice punctuated 'where' and paused on each of the others.

There it was. She had mapped out her most basic expectations of him. From now on, if he would stand to attention whenever she asked with his bits on full display, then anything else would be the literal cherry on top. Whether that be she just made him stand there feeling embarrassed, or whether she made him wank his cock for her amusement, or smacked it just because she had the authority and ability and wanted to see if he would resist dancing in pain.

"You will not," she lingered again for emphasis, "question me. You will have complete faith and trust in me... from now on."

She could tell that his head was absolutely full of questions. When would he be expected to do these things? Would there be any other witnesses? Surely she wouldn't deliberately embarrass him in front of other people? How long would he need to stand there for?

And so on.

Horror.

As she glared at him, she allowed herself a smile, though it probably was more of a smirk.

It took him a second before she once again qualified her control over him and put right the sense that he had escaped easily earlier.

'Kiss the... sole of my shoe!"

Her voice was barely a whisper. The crossed leg bounced the foot she meant.

There was no ambiguity or misunderstanding in her direction. She wanted to... no, needed to, test him. Had her previous instructions gone in and been understood? Had she gotten control over this neanderthal?

Fair enough, these were her nicest stilettos and not random trainers or boots with deep treads filled with goodness knows what. Simple glossy black patent with five inch heels and a flat sole at the toes. She wore them on occasion and though never in dreadful weather or through overly mucky ground, they were still not particularly sanitary.

They were definitely her 'fuck me' shoes and been very lucky for attracting men in her past. Some men didn't seem bothered about a woman looking overly feminine and for some, they were an obvious turn on, especially when coupled with her height and long haired elegance.

This was the first time she had got a man to actually kiss her feet whilst she wore them. There was something very powerful for her as a woman with a man kneeling before her, as though she was an empress of old with a slave, or a queen with her subject bowing his allegiance.

"Three..."

She watched his eyes. He dared not take them from meeting her gaze. The conflict was obvious but to not have a worry was unnatural. This was an older man with sensibilities and habits and with old style decorum.

"Two..."

If he broke too quickly, that would rob her of the excitement of training him. Of breaking him like a wild horse. Too slowly and that would mean he wasn't following her orders and, as far as he knew, potentially causing problems for his job too.

"One."

There was no option left for him.

Keeping his eyes fixated on hers, he slipped from the chair as though grasping for something he had dropped, and brought his head up to the flat sole part of her shoe. She heard the kiss and then watched as he righted and seated himself back in the restaurant's chair.

He was breathing heavily, though ironically, her own had levelled off throughout her countdown and now she was feeling extremely calm and extremely naughty. Yes, this was his punishment, but she was going to have some fun with it and make some memories for herself too.

It was time to see what else she could make him do.