Chapter 15

 

With her new piercing and status within the Society, Jackie found a new confidence within herself. She still worked at her job and did it well, but it was no longer her primary concern. She preferred to focus on the Society. 

Word would come on the company email that she would be expected to be at a certain address at a certain time. It could be in the middle of the day or at night. If it was during regular work hours she would simply make a note on her official online company calendar and no one questioned her.

The sex was good. She liked disciplining both men and women. Inflicting pain to heighten sex was a trick she had wished she had learned earlier, but she knew she was still young. 

The people she met she sometimes knew, but usually not. Often it was a couple, a man and a woman, but not always. Sometimes it was a party. Sometimes it was one person. Sometimes she had instructions going into the encounter, other times she would learn what was expected of her when she arrived.

She had no trouble playing the role of the dominant or the submissive. It was sometimes necessary to do both in the same encounter. 

Learning to roll with the strangeness of certain encounters was necessary, but enjoyable. One time she was called to a very expensive apartment in one of the downtown’s high rises. The man waiting for her was an executive from a different department than the one she worked in. He was middle-aged with graying hair. His wife was there with him. She didn’t participate.

He stripped and lay down on the huge bed. Jackie saw his cock was already hard and she wondered if he would hump the bed while she worked. She took off her office attire. Underneath she wore a red pushup bra, matching panties, a garter belt, and white stockings. She didn’t remove her tan knee-high boots. It was an outfit he had requested.

She paddled his ass until he was screaming for her to stop. His ass turned from pale white to pink to red to bright red and started to purple as bruising set in. She didn’t stop.

Jackie only stopped when the executive’s wife told her to. That was all part of the plan. Sometimes the other person in the room masturbated while Jackie worked. Not this wife. She sat in a chair in her too expensive and well-tailored yellow suit and watched attentively. The executive rolled over. Jackie stroked his cock. He lasted less than a minute before he ejaculated all over himself.

She left him in tears and put her clothes back on.

The wife accompanied Jackie to the elevator.

“Thank you,” she said. “We used to hire a pros— that is a sex worker, for this. He has a terrible humiliation kink. Next time would you mind verbally degrading him?”

“Of course,” Jackie said pleasantly.

“I’m so used to giving the other women cash payments,” the wife said. Jackie noted she was still pretty even if her almost perfectly dyed hair was starting to show gray roots. “I know I’m not supposed to, but if there’s anything I can ever do for you…”

“I’ll let you know,” Jackie said politely as she pressed the elevator call button.

The wife looked nervously at the numbers on the display counting the time it would take for the elevator to arrive. She produced a business card from her jacket pocket and offered it to Jackie. “I prefer not to deal with sex workers, but my…” She frowned. “I don’t have sex with my husband. I have a man, a younger man, who I see on a regular basis for that. He wants to see me with another woman. Is that something you do?”

Jackie accepted the card. “I do. But I limit my partners to those in the Society.”

The wife pursed her lips and made a quick decision. She half turned and pulled up her skirt to display a shapely thigh for an older woman. The skirt kept going up. Her thigh-high stockings were revealed to be held up by garters. She wore a thong that would be more appropriate on a younger woman. On her right buttock she had a small tattoo of the Society’s roseate symbol. “I am a member of the Society.”

Jackie glanced at the card. It held the woman’s name and phone number along with the company’s name and logo. No title. No other indicia. “I’ll call you,” said Jackie.

“Thank you.”

The next day at the office Jackie happened to see the executive. He was walking slowly while talking to another staffer. He claimed his janky movements were from a particularly vigorous game of racquetball combined with an unexpected bout of middle-age. 

Jackie kept her face neutral. It wasn’t her place to get involved. She did call the wife’s number and left a voicemail. She wanted to see what would happen.

 

It was a month after she had returned from the mansion that Piper was brought into the company for an interview. Ophelia had been correct; there were always openings for talented people. Jackie wrote a formal recommendation; she didn’t bother to check the position or department her cousin was applying to. Piper needed a job and she’d do whatever it took to find her a job.

Piper was thrilled when she was hired in short order. Jackie suggested that they move in together to save expenses and not have to share an apartment with two people she had no attachment to. Plans were made. Possible apartments were located.

Jackie continued her official and unofficial duties. She didn’t have encounters every day, usually it was twice during the week and one long day on the weekend for a party.

The weekday encounters were enjoyable. She got to know the regulars. Ivy was the wife married to Harlan, the executive with the humiliation kink. She would often have sex with Ivy while Harlan was tied up and allowed to watch. Sometimes she would have sex with Ivy and her lover, a man barely older than Jackie named Emery. These sessions would be recorded on Jackie’s company-issued phone. The next day she would take her phone to Harlan’s office for him to view. Sometimes he would cry while watching. Sometimes he would pull out his cock and jerk off. He never asked Jackie for sex at the office though he was well within his rights to do so. Afterwards she would delete the video until the next time.

Many of the men that she was scheduled with wanted to be spanked or paddled or abused in some way by her. Afterwards, they wanted to fuck her. Sometimes she would refuse but give them a handjob. For this they always wanted her more. Sometimes she would let them fuck her, but insist they eat their own cum from her pussy when they were done.

They always did as she asked.

She never had sex alone with a woman. Jackie found that strange. She had enjoyed sex alone with Ophelia. She didn’t see Ophelia as much as she wanted, but realized she was no longer in full need of having a mentor. 

She and Piper moved in together. It was an apartment with a bit of a view of Columbia Park. It had a parking garage and a doorman and more amenities than they needed. Piper worried about the rent. Jackie assured her that she could afford it but didn’t tell her the company was giving her a special housing allowance. Jackie felt no shame in taking the larger bedroom with the better view.

She didn’t tell Piper about her Society-related activities. Anytime she had to be gone in the evening or weekend, she claimed it was work related.

Piper accepted her explanation without fuss.

After Piper had been at the company for almost three months, Jackie was summoned to Harry’s office. This didn’t surprise her. Maybe Harry wanted to fuck her. Maybe Harry wanted to watch as she fucked someone else. Maybe Harry wanted Jackie’s special brand of discipline and then submission. Jackie had earned a reputation in the Society that was doing her much good.

Ophelia was in Harry’s office when Jackie walked in. That didn’t alarm or surprise her. Ophelia wasn’t only Harry’s property, she held some semi-important position in the company.

There was no exchange of pleasantries. Harry got right to the point after Jackie seated herself in the unoccupied chair in front of his desk. Ophelia sat in the other chair. “You’ve been with us a year now, Jackie, and you’ve become a cherished part of the Society.”

“Thank you.”

“We need you to start recruiting new members.”

Jackie nodded. Maybe this wasn’t her forte, but she would do whatever the Society asked of her. “Of course. I think my skills are best in serving active members, but I’ll help however I can.”

“This is just a one-time thing,” said Harry.

“You have someone in mind?” She wondered if it was Emery, Ivy’s lover. He was a good fuck and she wouldn’t mind doing whatever was necessary to recruit him.

“Yes. Piper Sipkins.”

Jackie blinked. “That’s my cousin.”

“Your second cousin.”

“I’m not having sex with my cousin. Or anything like sex.” It was the first time she had ever refused a request from the Society. It scared her.

“I’m not asking you to. I’m asking you to introduce her to the Society.”

“No,” she blurted out.

Harry met her with a level gaze. “The Society is asking you for this favor.”

“I don’t want her in the Society. She doesn’t need to be involved in all of this.”

Harry sniffed. “You seem to enjoy it. She’s an adult. She can refuse if she wants. We’re merely asking you to tell her the advantages of being in the Society.”

Jackie’s heart was thumping against her breastbone. She could feel it. It was painful. At that moment she realized how much Piper looked like Tina. A younger version of Tina, but they were of the same type. Had Harry spotted Piper and wanted her? Was there a pressing need for young women like Piper to be brought into the Society? Was there some other executive in the company who wanted Piper? 

It was all her fault; she knew that. Whatever the Society wanted, it got. They wanted her; they got her. They controlled the company. She needed to protect Piper, not draw her into this complicated life.

“Jackie? Are you listening to me, Jackie?” Harry was glaring at her.

Jackie roused herself. “Sorry. What were you saying?”

“This is no longer a request. You’ll be recruiting Piper into the Society. It should be easy. You know her well. She’s young. You two live together. She’s unattached to a partner.”

“I’m not doing it,” Jackie flatly refused.

Harry frowned at her. “You can’t refuse.”

“I can and I do.”

“Don’t refuse, Jackie,” Ophelia advised her.

Jackie looked at Ophelia and was about to say something, but Harry stood up from his chair and started moving from behind his desk.

“Stand up, Jackie. There are some things that need to be explained to you. You’ll need some reinforcement in this lesson.”

 Jackie stood up and realized her knees were weak. She briefly thought about running for the door but realized she couldn’t move. 

Harry grabbed her. He was strong. Much stronger than her. She was afraid. He whirled her around and bent her over the desk. 

“Ophelia, get the restraints and paddle out of the bottom drawer of my desk.”