Five

"Pegging." He wasn't sure what to check. He watched plenty of porn and had seen older men pegged by their Mistresses. The thought of it made him shiver. He checked "Very interested."

"Cuck?" He laughed to himself. He tried to imagine dragging his ex-wife Stephanie into this fantasy. Even in her fifties, she still had a hard body and her tits had gotten much larger. He wouldn't have minded watching her get gangbanged by men with big, shiny cocks, and maybe be tasked with "cleaning her up" after. Steph was pretty good in bed, and never turned down a chance to fuck. It was everything other than sex that tore their marriage apart. He reluctantly checked "N/A."

It took him over an hour to complete the survey. He answered every question truthfully, admitting to himself in the large, backlit letters on his computer screen, that he had a number of unresolved and serious sexual hang-ups.

He wondered how she would judge his answers, but only paused a moment before he took a breath and hit "Send."

* * *

David trembled a little, sliding across the back seat as his Uber ride took a long curve. It was a bit before 8 p.m., and he was nervous about being on time with the mysterious Acadia. It felt odd, too, to have nothing to carry except the new phone in his pocket. As instructed, he had left everything at home -- his car, wallet, phone, watch, even the key to his apartment. He'd have to use the spare key hidden in a magnetic box in the fire extinguisher box near his apartment's door. His eyes were wide open, watching the oncoming traffic and looking side to side at the pricey looking neighborhood.

They were in a part of the west suburbs he didn't know at all, in an area with curving streets and fewer but larger houses with broad expanses of lawn and expensive cars in their driveways.

"We're here."

The car came to a stop and the driver, a dark haired woman who appeared to be in her forties, was already on her phone scheduling her next pick up. She ignored him during the half hour ride and just wanted to get on to her next call. David thanked her, stepped out, and shut the door of the compact Korean made sedan.

At the curb, David stared at a large two story home with a façade of brick and a circular driveway in front. The dark brick, the small-paned leaded glass windows, and the steep pitched slate gable roof gave it an English Tudor look, and there were no nearby houses in sight. He walked up the winding stone path as the Uber car pulled away. He tapped the knocker on the arched wooden door (there didn't seem to be a doorbell) and waited.

The latch clicked, and he held his breath. The door opened but he made no move to go in. It was certainly Acadia. She was slightly taller than him, and wasn't smiling as she looked him over. She was even more attractive than he remembered, tall and slender, her heart shaped face with perfectly applied nighttime make-up, wearing a simple sleeveless blue dress with a low enough neckline for him to see her smallish breasts. She was in low heels with a gold link necklace and matching bracelet. It wasn't some Domme costume he had imagined, but was dressy enough for a Friday evening out on the town instead of at home. She sighed, but said nothing, and motioned him into the hall. It had the usual features, a hanging lamp and a small side table, with a temporary line of blue tape on the brick floor.

He stepped to the line and stood still, taking his cue from her attitude. He had tried to dress carefully, not too casual and not assuming anything: a tweed jacket, gray oxford shirt, dark pants, and simple wingtip shoes. He didn't want to make any kind of statement with his clothes, and stood there anxiously awaiting her judgment.

She ignored his eyes and stepped closer, feeling the texture of his jacket, touching his back and thighs, patting the slight paunch on his belly, and then sliding her hands over his chest. She was close enough that he could smell her perfume. It smelled expensive to him. She dressed and felt as if she came from money.

She suddenly gripped his chin as she had with the woman in the bar. She was close enough for him to see the flawless skin on her face.

"Hmm. OK." There was disappointment in her voice. His posture sagged a bit at her hint of disapproval. He awaited her verdict.

"This is the one time I'll explain what I hope to do. If you agree, take a step across the line and we'll begin. If not, just go back outside, and wait for a car to take you home and we're done."

She held him by the chin again and looked into his eyes. His instinct was to avert his eyes, but he couldn't tear loose from her piercing stare. She told him that even across the room in the bar, she could see his submissiveness. Her unblinking eyes bored into him as she told him his boring life was about to change. She continued on, peeling away his layers of defenses and exposing his prejudices and preconceived notions.

"Like most men, you live entirely inside your imagined masculinity, in the way you think. You chose your own clothes for this moment in terms of your comfort and style, but you think that I chose my clothing to present my body to you. You are waiting for me to finish talking, while you imagine what my clothing displays or conceals and how you might like to touch me and use my body for your pleasure. It's a masculine idea of wanting and taking, but my new goal for you is a human idea of giving and offering, which you probably see as your feminine side."

Busted. It was true -- his mind was half listening as he was distracted with his own ideas. He had already studied Acadia: the way the simple dress hugged her breasts and the curve of her hips and the look of her bare skin of her arms and calves. He did try to imagine what she wore under it, thought about her lips on him, pictured what she might look like naked, and tried to imagine her wanting his body -- all in his first minute with her. If his manner of dress and presentation didn't already betray him, the growing bulge in his pants would have.

He tried to clear his mind and focus. She went on, not expecting him to talk.

"Whatever your work is, it probably involves selling things or ideas to other people, and all your previous relationships with women have been about selling them some idea or getting past their resistance. We're going to change that now ... if you step across the line. If you like what you are now, just go home."

She took a step back and crossed her arms, with a bored neutral look. She already knew he would step over the line, but waited for him to reach the same conclusion.

David thought about his previous relationships, his failed marriage with Steph, and his lonely nights at the bar without any connection. He then thought about the website -- and Four -- and his destiny as yet another anonymous number with a black line to hide his eyes, and all of his sexual perversions listed in painstaking detail. It now didn't surprise him that the latter appealed to him more, and even excited him. Taking a deep breath, he silently stepped over the blue tape.

Acadia allowed herself a knowing smile when David stepped forward. She had tired of "Four," as she had already probed and explored the limits of his submissiveness, and his reluctance to engage in areas that were of more interest to her, such as humiliation and anal play, made her lose interest. David presented fresh possibilities, and the profile he submitted seemed to highlight his interest in humiliation. She would teach him the pleasures of anal. She gave him her usual acceptance speech.

"From here on, when you're with me, you'll have nothing -- no property, no personal privacy, and no second chances. You belong to me, and me only. You will not touch yourself or cum without my permission. You will only answer to the name "Five." You will be done with your training when I say you are done, and not a minute earlier or later than that. Do you understand Five?"

David wouldn't make the same mistake again, either calling her anything other than her name or asking a question when one wasn't invited. "Yes, Acadia."

"Good. Strip now. I'll be back in a moment. Fold your things neatly on the table."

She turned and went around the corner. He watched her as she left, trying not to think about her body, and thinking instead about his complete surrender of control to her.

He was excited, but hopeful too, as he slipped off his jacket and then the rest of his clothes and stacked them on the small side table. He wanted to look his naked best, with bare feet on the cool brick, shoulders back, and conscious of his belly but also his exposed cock as it hardened. Femdom fantasies filled his mind as he heard her returning, though to his terror there were two sets of footsteps.

His heart dropped into his stomach. He hadn't considered the possibility there would be more than one person in the house. He heard Acadia's voice, exhibiting a hint of exasperation.

" ... a bit slow on the uptick. Well ... we have to start somewhere."

Acadia stepped into the hall with a second woman. Not the one from the bar, but someone in her thirties with long black hair and fine Eurasian features. Acadia wore the same blue dress, not the leather outfits from his imagination, and the other woman wore a white shirt and a simple dark skirt with low heels, and carrying a small wicker basket. The other woman was much shorter, and stockier, with larger breasts and a fuller face. She didn't seemed to be pleased to see a strange, naked man standing in the entranceway.

David suddenly felt his nakedness, and the urge to cover himself with his hands. Acadia's disapproving look froze him in place. The other woman looked on with amusement.

"Five, this is one of my subs, Gamma."

Acadia lifted up the sub's short skirt to her waist.

"Honey, show him your mark."

The woman let a look of annoyance cross her face, and turned sideways so he could see the Greek letter "gamma" in a circle marked in henna on the side of her muscular upper thigh. David could see that she wasn't wearing any panties, and that her pubic hair was jet black and straight. He tried to stop himself from picturing the rest of herself naked and tried not to stare at her breasts. He failed in both regards.

"So, what amuses me, Five, is control and teaching. Everyone is learning something about themselves and what I want from them. No one is just playing here. What I want for you is to get you out of your usual groove of thinking with your cock. We'll explore more detailed ideas later, but for now learn Position One. On your knees facing us, legs wide, back straight."

David paused for a moment, absorbing the command.

"Quickly," she admonished him.

As he began to kneel, Acadia reached into the basket and flicked several grains of rice onto the floor. He watched as they skidded underneath his knees. The pain surprised him, just from kneeling on the rice, as he took his position and kept his head up. She stepped closer, using the pointed toe of her shoe to nudge his legs wider. When she was satisfied, she pushed the tip of her high heel against his exposed balls until he winced.

"Lay your hands on top of your thighs, palms up, and keep your mouth slightly open. The point of this position is easy inspection and access."

She walked slowly around him, using her hands to make slight adjustments to his position.

"You are right handed, aren't you?"

He nodded.

She reached into Gamma's basket again for a small bottle of lubricant, and poured some into the outstretched palm of his left hand.

"Well, here you are, in a fantasy you've dreamed of ... naked, with two women waiting to see you demonstrate that mighty cock."

She circled her thumb and forefinger to make a stroking motion to mock him.

"Don't laugh, Gamma, I'm sure he's thinking that. Cum for us now Five, and if it takes more than a minute I'll punish you later." Acadia was grinning, and Gamma did laugh. Acadia looked at her watch and David realized he had to begin.

He began stroking, kneeling up higher, trying to ignore the pain caused by the rice kernels digging into his knees. It felt odd using his left hand and it was difficult to get the right rhythm and sensation. He tried to focus on a mental picture of Gamma with her skirt up and his face buried between her legs, his tongue lapping against the straight glossy black pubic hairs and the glistening lips of her pussy. He started to snort through his nose as he got close, now imagining Acadia's hands pressing against the back of his head as he ate Gemma's pussy, him fighting to breathe but not wanting to relinquish his position between her legs. His cock started to swell in his hand and he felt his orgasm was imminent.

Acadia took the basket from Gamma and handed her a short glass container. Watching his hand, now a blur, the sub leaned close to slide the glass over the head of his penis as he stilled, and then spurted ropes of cum into the small bottle. He had never masturbated in front of others, even his ex-wife, and was surprised at the intensity of his orgasm. She put a small towel under him, then stood up. When she turned back to him, she had fitted a rubber nipple to the container, which he saw now was a small bottle ... a baby bottle, partly filled with his cum.

"So, you see the point now, Five? No action without a lesson. So much for your powerful display; take it all."

Acadia took the bottle from Gamma and pressed the nipple against his lips. He parted his lips to accept the nipple, and she smiled approvingly as he paused a moment and then sucked on it. He shifted painfully on the rice and tasted his own bitter, musky ejaculate. He should have been ashamed to drink his cum in front of two women he had just met, but he wasn't. He felt pleasure, and not just the pleasure from physical sex, but the pleasure from pleasing Acadia.

"Now I want to keep your attention. Gamma, fit him please."

The dark haired woman pushed his legs wider as he knelt, cupping a plastic shell around his now limp penis and clicking it closed. He realized he was being locked away, and prevented from having any erection at all.

"But, please, why...?" he uttered before he realized he might be speaking out of turn. He wasn't expecting this, having a chastity device clamped on him.

"Five, you need to pay attention now. The point here is to use your other senses and think about others, not just about getting off. You're now a giver or someone to be used. There are a lot of unexplored avenues for you. Get up, follow Gamma, who by the way saved some clean-up work for you."

Acadia looked at the empty baby bottle.

David realized that she was waiting for a response.

"Yes, Acadia. Thank you for teaching me ..."

"Teaching you what?"

David thought for a moment.

"For teaching me that the needs of others come before mine."

She gave him a smile of approval. David felt a glow of satisfaction from pleasing her, then shuddered when he remembered Four's warning that he would anything to please her.

As if to reinforce the lesson, Acadia tapped the plastic shell around his genitals with the tip of her shoe to remind him he was owned now, and that he had no personal space.

"You need to learn to express your gratitude and submission without words, Five. As they say, you know a man is lying if his lips are moving. Try not to think ahead too far. Just live in the moment and let your body learn to respond."

Acadia turned away, and he walked after Gamma down the hallway. He couldn't help but admire Gamma's shapely ass in the short skirt, and immediately thought about the wetness of her pussy, and felt immediate pain as his cock tried to harden in its tight enclosure.

Old habits literally died hard.

***

Acadia -- Ten Years Earlier

New York City

"Fuck them ... before they fuck you," Acadia advised her client, a European based pharma company. She stood there confidently as a room full of men watched her.

"I hear you Acadia. You've been right this whole way. I should have known they'd try to double cross me on this deal." The CEO of the company was in a conference room with Acadia and a team of Zurich based lawyers and accountants. Acadia advised them on the company's two previous deals, and her word was gospel.

"Get it done tomorrow. File the papers we've had the lawyers prepare and let's get the show on the road," she said with authority. Acadia knew her client's strategic "partner" would try to take the whole deal for themselves. They didn't know that Acadia had anticipated their move and had already located another bank to take their place, and that the necessary papers would be filed the next day to make the change. This would all be accomplished with the beauty of a fine cut of a razor blade, instead of the blunt force of a sledge hammer. The precision in the execution of her well thought out plan was Acadia's calling card.

In other words, she was expensive ...and worth every penny.

Guiding mega-transactions, such as the current merger she was spearheading, gave her sharp mind the challenge she needed. Neglected, but not forgotten, were her physical needs. She was attractive and always appeared well-kept. A few inches shy of six foot, she was tall and willowy, with smallish "A" cup breasts. She kept her auburn brown hair shoulder length, and had a personal shopper that kept her business attire appropriate, with a hint of sex.

At twenty-eight, she had had a few long term relationships of more than a year, but those fizzled under the sheer weight of her all-consuming mergers and acquisitions practice. When she was "on," her phone was simply an appendage of her hand, and quarts of coffee flowed through her veins. Most of the time, she satisfied her physical urges with one night stands and a vibrator that travelled wherever she went. She found sex to be pleasant and always wondered why it was such a big deal.

She felt that way until she discovered domination. It suited her personality, and gave her a level of sexual satisfaction she never experienced with conventional sex. Becoming a dominant wasn't something that she was looking for. It found her and changed her.

She wasn't sexually precocious and didn't really have serious sex (beyond the clumsiness of back seat fumblings) until she was in her twenties. At that time, even her sexuality was still in question. She was pursued mainly by men, but her last two relationships that overlapped were with a man, and then a woman.

The rush and adrenaline from her high powered job wasn't enough for her, so she was continually looking for outside interests to sate her seemingly inexhaustible drive.

Acadia frequented private clubs, and made it a habit to hang with a circle of friends that were always interested in what was new. At that time, the novel "50 Shades of Grey" was being passed around, and she and her women friends discussed how kinky the sex was. Acadia wasn't overwhelmed with the literary quality of the book but was fascinated with the scenes involving Christian Grey, his assumption of control over Anastasia, and the complex war of wills between the two of them.

Being her efficient self, she instantly located porn that depicted amateurs performing real acts of domination and submission. Some were comical, but some riveted her eyes to the assertion of control by the dominant over the submissive and the true zeal of the participants. She wondered what it would be like to be a dominant, but it was only a fleeting thought, and the interest was soon lost in the mountain of work that was still on her plate.

* * *

It was a Friday night and Acadia was uncharacteristically alone in her expansive loft apartment in SoHo. She had just finished a major project and was bored, flicking through a stack of magazines she saved for such an occasion. One magazine profiled an emerging jazz trio that featured a saxophone player she was familiar with. The magazine mentioned that the trio was performing that night at a club in the East Village. She decided to go, but was still wearing her work clothes. She decided she didn't have the time to change, so she went as she was. She was to find out that her sharp business attire, a turquoise colored jacket and matching skirt and a crisp white cotton blouse, and black pumps with stiletto high heels, made her stand out in a bar filled with people dressed in casual clothes.