That was Always the Plan Ch. 07

Dear readers, I would like to thank Literotica user and editor Skye Kahoali'I for their help in editing this story. I am a new and amateur writer and without their time and effort, it would not have been possible to bring this story to you guys.

This chapter continues the tale with Jim and his plan. Comments and feedback are as always, welcome.

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Tiffany sat at her desk in her office. It was early in the day, but she had gotten into the habit of coming early to the office. This helped her get one or more of her tasks done without much interference. It had been two months since the fateful summer retreat. An event which had changed her life and turned it on its head. In these two months, Jim had not once called her or talked to her about those two nights. Two nights of some amazingly fulfilling sex. She fondly remembered the night which also awakened the dormant Domme personality in her. She had known that Jim would not call her, that he had moved on. However, she had to admit to herself that she was a bit stuck on him. Wisely though, she too had kept her distance and hadn't called him. She had been on the verge many times, but she never did it.

In the last two months a lot had changed in her life. Tiffany had separated from her husband and moved out of their house. The divorce was proceeding. She pooled all her savings and bought a penthouse in the city for herself. In her new life, she had kept up the sexual appetite she had newly found in herself. She had received discrete visits from both Philip, a new intern in her team and Chloe, who was the first girl she'd help dominate and fucked, along with Jim during the Retreat. Chloe proved to be a great sub and adept at pleasing Tiffany and her moods. Her life was in upheaval, but Tiffany was trying to sort her issues out one at a time. She really needed the morning assignments she was receiving to keep her mind off her worries. It was 9:30 am and she didn't have any meetings for another hour, meaning she could keep herself occupied till then. Just then, her secretary beeped in.

"Ma'am, someone is here to meet with you. He says he has an appointment." For a second, Tiffany panicked. She wasn't in a frame of mind to meet someone right now. Coworkers and clients here usually came a little later in the day. She wondered who wanted to see her so early. Had someone found out about her indiscretions?

"Who is it? I'm not aware of any appointment for 9:30."

"Ma'am, it's Jim from the tech team. He says he discussed this appointment over a phone call yesterday."

Hearing the name, she relaxed. She wondered what made Jim suddenly break the silence he had kept up so admirably for the last two months. She felt her irritation with him rise through her. Perhaps she should tell him, she was busy and ask him to come back later when he had an appointment. She would love to snub him. At the same time, however, on hearing his name she already wanted to see him. She so wanted to know why he was in her office so early in the day. She knew there was no point resisting.

"Send him in."

Jim entered the room and prudently waited for the door to close. Then he gave her his signature smile which went all the way up to his twinkling eyes. 'How was she supposed to resist this guy?' thought Tiffany. She tried to keep up her pretense by looking cold and indifferent but wasn't sure if she succeeded. Grudgingly, her face broke into a grin too. She was hurt and angry but then you simply couldn't remain indifferent to Jim for long.

"That is much cooler of a welcome than the last time!" Jim said grinning broadly. "I expected you to run into my arms! Are you angry with me?" mocked Jim, knowing full well that she was.

"Because this is not a welcome, Jim! I really don't need to stand up for every Tom, Dick, and Harry that comes into my office!" Tiffany said. Her tone was impatient but under control. Jim kept grinning at her and this finally broke her restraint. "You are a fucking bastard, Jim. Where the fuck have you been for the last two months? And then you wake up one day and simply drop by without an appointment, as if you own the office."

Jim was still smiling. He took a chair in front of Tiffany. She was very close to picking up the paperweight from the desk and throwing it at him. Jim loved the way Tiffany was possessive of him. He had missed her too, but the work he had been doing for the past two months was his first priority. He couldn't endanger his plan for anything.

"Tiffany... you knew what you were signing up for. You knew I only do one-night stands without any strings attached."

"Yet, here you are, sitting now right in front of me," said Tiffany sharply.

Jim wasn't making much headway in the conversation. He really did not have much time, and timing was of essence if he wished to pull off his plan successfully. He sighed audibly and pushed back his glasses. He took a moment to compose himself. He knew only the truth or at least most of it would convince Tiffany help him.

"I am here today because I trust you the most in this organization. You do mean a lot to me and there is no one I would rather turn to for help. You are the only one who can help me, and I need that help badly," Jim said looking straight in her eyes.

His voice was earnest and pleading. No one who knew Jim well would have ever thought him to plead to anyone. Tiffany arched her eyebrows, clearly very surprised. She tried reading his face. There was no lie in his eyes. She was genuinely concerned now. For all her irritation, she really cared about Jim.

"Stop!" Tiffany said, looking into the distance. For a second, Jim wondered who she was talking to. Then he heard a noise coming from under her desk like a small animal. Then, there was a loud sound of someone banging their head against the underside of the table. Jim was curious, and he stood up and walked around her desk to the other side. At first, he was shocked with what he saw. Then, he began to laugh uproariously.

Tiffany was sitting naked from the waist down on her chair. Her shaved camel toe was open for viewing to him and he immediately felt his cock stir. Chloe was sitting on her haunches under the desk with her blouse open and mouth glistening. Jim let his eyes roam over Chloe's body. He could feel himself hardening further seeing her naked boobs with inch-long erect nipples. She had a collar on her neck which bore the words 'Tiff's Slut!'. She had turned beet red with Jim gawking at her. He looked back and forth between Tiffany and Chloe and then laughed even harder. Seeing her glistening mouth, Jim guessed that Chloe had been servicing her Mistress's pussy.

"Chloe, you can leave. We will continue where we left off, later," Tiffany spoke with composure.

Chloe got up immediately and stuffed her boobs back in her bra hurriedly and began to button her blouse. Tiffany was proud of her. Chloe had been trained not to stop pleasuring her Mistress's pussy even if interrupted. Today, even after hearing Jim, Chloe kept her focus on her task right in front of her. Of course, Chloe did know through first-hand experience she had no choice because she would be cruelly punished otherwise. Chloe got her buttons wrong the first time and then corrected them, staring at Jim with a seductive smile on her face. Tiffany scowled, mentally noting punish her for her impudence the next time they were alone.

Chloe's eyes shone with expectation at Jim. All through Jim had been smiling and she had been grinning almost stupidly at him. When she finally collected her papers and was about to leave, Jim stopped her. He came near her and Chloe's heart beat faster anticipating him touching her. However, he only straightened her hair with his fingers and removed her collar, which she had carelessly forgotten to remove, and handed it to her.

"You need to be careful. You don't want yourself or your Mistress getting into any kind of trouble, now, do you?" Jim queried seriously. "Maybe I can borrow you from your Mistress for a weekend. You have no idea how much fun we...I could have with your body."

Chloe blushed and looked expectantly at her Mistress, who simply dismissed her with her eyes. As she turned around, Jim smacked her ass hard causing her to yelp and shuffle through the door closing it on her way out.

"She is quite a doll," Jim told Tiffany. She scowled back at him. Partly to change the topic and partly to take back control, she asked, "You said you were here to ask for help?"

"You sure I can speak my mind or am I waiting for other semi-naked girls to jump out from behind the curtains," he teased her.

"Oh, shut up! Very funny! You weren't available...what did you want me to do? Starve myself?"

Jim sat down again. There was a nervous pause before he spoke. Something in his demeanor made Tiffany sit up straight and pay attention.

"Tiffany, I'm serious. I'm taking a big risk coming here. What I am about to tell you cannot get out of this room under any circumstances. I need your help and I wouldn't be here or involve you if there was any other way," Jim said earnestly.

Tiffany was concerned about Jim now. She knew she would do anything to help him out.

"Jim, it's okay. You said you trust me, and you can trust me completely. What is this about? You seem to be worried. How can I be of help?" she asked earnestly.

He smiled.

"So, it's like this. Four years back when Henry became the CEO, he took an uncommon interest in my work. I had no idea why. I didn't and still don't like him much. He, however, kept tabs on my activities and then found out about my, umm...activities with the interns. He then came to meet me and threatened to throw me out. I have always been a little short-tempered and back then, my temper got the better of me. I told him to get lost, to throw me out and see if I cared. It would hit this company harder than me. That momentarily stunned him. He went away that day. He discussed my role with the other senior management members and realized that, what I was saying was not far from the truth. He came back to meet me. This time, in a more congenial manner. He still didn't apologize, but took a different tack. He told me to do a small thing for him and he would let me keep my job if I did it."

Jim took a pause for a deep breath before continuing.

"I had no reason to do it for him. I had nothing to fear from him. At most, I would lose this job, but it wouldn't really be difficult for me to find another one with my skills. I know I should have refused him that day, but I didn't. I regret getting myself into this mess even today," Jim admitted

"What did he want from you?" Tiffany asked curiously. She, too, had her own deep misgivings about Henry. In fact, she hated that misogynistic pig. Only a few months back she'd had a verbal standoff with him during an important meeting. Henry, who did not understand marketing very well, wanted to implement a campaign which would have been disastrous for the company. He didn't want to listen to her and even called her a 'a simple-minded girl.' Tiffany suspected, correctly, that Henry would not listen to her simply because she was a woman. That got her really riled up and they'd had a shouting match. She finally lost her temper and walked out warning him about the consequences. Luckily, the other senior managers who were able to understand Tiffany, convinced Henry of not going ahead with the campaign.

"He...well...he asked me to convince a girl to go alone with him for a weekend on a business trip." Jim replied, shaking his head as if in disbelief at his past actions.

Tiffany's mouth fell open, "And you said yes to this? What, do you moonlight as his pimp?"

Jim flinched as if she'd struck him. "Well, I wanted to try my...umm...hand at it. At that point in time it was more of a lark. Also, I could choose any girl. So, I was sure I could convince someone who would consider this as a stepping stone on her career path to bigger and better things. So yes, I agreed. Remember Jill, that intern from the procurement division? I managed to convince her, and she was actually excited about going through with it. I thought nothing more about it and thought that was the end of it. Unfortunately, Henry had other intentions. He wanted this arrangement to become an annual thing so he asked me to get someone else again the next year. I unfortunately, knew just the right girl and did it again for him. I started having serious doubts about Henry even then. But I confess, since it did not affect me directly, I was never too bothered about it."

"Last year was when the shit got out of hand. Instead of letting me select the girl who might want to go through with this, Henry gave me a name and asked me to get her to agree. At first, I flatly refused. He asked me to at least try and that there was no pressure. I took it up as a challenge to test my convincing abilities. It was Jean from marketing that time. Well, I did manage to convince her but after that time I politely asked Henry not to be part of this stupidity."

"Suddenly got a conscience? Or a spine? How could you, Jim? For all the gossip that goes around about you in this place, I have always heard that you treat your "girls" right. I know that you even got a new position for Mindy after she was fired," Tiffany said.

Jim shifted guiltily in his seat. She had no idea where Mindy was or what his pet was doing, and now was not the time to enlighten her. Jim also did not want to tell her his reasons for asking out of Henry's little game.

When Jean had come back, she came to meet Jim. In his office she had lost it. She had broken down, sobbing. Henry had been absolutely obnoxious with her, treating her like a street prostitute. One of the nights, Henry had drunk far too much, and things really got out of control. He'd asked Jean to do things she was absolutely uncomfortable with. Backed into a tight corner, she had no option but to comply unconditionally. Jim consoled her, even apologized to her. He placed a few calls and got Jean a new job immediately. He asked her to quit and put this behind her forever. He also promised her, Henry would get his comeuppance and when that happened, he would let Jean know.

"This year, Henry gave me another name. Henry wants me to get that girl specifically, and even threatened me when I said no," Jim said simply, staring straight into her eyes.

"Who's the girl?" asked Tiffany, knowing or at least guessing the name. She stared right back into his eyes, refusing to drop her gaze even for a second.

"You!"

Tiffany sat bolt upright in her seat. At this moment, she despised the man sitting in front of him. She felt disgusted with Jim and utterly betrayed by him.

"So, is that why you're here? You think you march in here, work your hocus pocus on me, and make me go with him? Were all these efforts for Henry? Was the fucking retreat a warm up act to this? Jim, what the fucking hell do you take me for? You bastard!" Tiffany shouted losing control over herself.

"Is that what you think of me? Would I ever-?"

Tiffany cut him, "Don't you fucking dare take the injured act with me. You are fucking as bad as that Henry asshole. No! In many ways, you're much worse than him. Tell me, why the hell are you here, if not to pimp me out to Henry?! You fucking bastard!!"

Jim remained calm. He knew he deserved the shouting at he was getting. In a way, he was happy that Tiffany was venting her anger at him. It meant he meant a lot to her. It felt like a great weight of guilt had lifted up from his shoulders.

"Henry left on his trip on Saturday. Which is why he isn't going to come in today! And seeing that you are here in front of me unaware of any of this, I am sure I have not set you up with Henry."

Tiffany was surprised but still angry, "So what? You got another innocent intern to go with him and get fucked over?"

"No. Whatever you think of me, and though I deserve it, I want nothing more to do with it anymore. Henry is in for a surprise. There is a big shock waiting for him there and when he returns tomorrow, he is going to be pissed off," Jim finished with a smirk.

"What-?" Tiffany started asking but Jim cut her off.

"You don't need to know that yet. Just believe that his time is coming to an end. Everything is planned." Jim said mysteriously. Tiffany frowned, and her shoulders drooped a little.

Tiffany felt her anger abating. Try as she might, she couldn't stay angry with Jim for long. She was already feeling a growing need to be near him. To touch him, to let his hands roam all over her body. She stood up from her chair and walked over to sit on the table in front of him. She was naked from the waist down. She spread her legs to let him see her glistening cleft. Jim smiled at the brazen temptress that had become Tiffany's new nature.

He moved his hand and positioned it on her thigh. With his thumb he began to rub her clit. She cooed softly. She wanted answers, but more than that she needed him. She bent forward over his hand and planted a deep kiss on his lips. He kissed her back with equal passion. It was a long time before they both broke the kiss.

"Tell me," she husked, "Why are you here?"

"I'm here to ask for something much more from you. I'm here to see if you can trust me completely!"

He told her his entire plan. This was something he had been scheming about over the last so many years. With every sentence he spoke, her eyes got wider and wider. Then he also told her what he wanted to do and how she could help. Once he finished, he looked straight into her eyes and waited. She looked a little fearful but admiring all the same. He could tell she was still digesting all the news but was impressed all the same.

"So, you mean to say that the anonymous buyer..." she let her voice trail off, not completing the question.

"Yes," was all Jim said. He waited for her to speak. Tiffany was overwhelmed with all the information. She took her time before replying.

"Oh, Jim, you're asking too much of me. You know the current situation I'm in. I simply cannot afford to lose this job. If you fail, it will be both our necks on the line—"

"Tiffany, believe me, I will never endanger you. I wouldn't be here if I wasn't sure. I'm here because there is nowhere else to go. Trust me!" Jim said.

"Let me finish, Jim. Even if Ted would have asked this from me after ten years of marriage, I would have refused him. However, you're different. I simply can't seem to say no. For you I'll do it...but only for you. After all, this new life, this freedom, and even my new-found sexuality are all gifts from you," She grabbed his hand and pushed it over her leaking pussy.

"Tiffany, I don't know what to say..." Jim started.

"Then fucking shut up. Just remove your pants and give me what is mine. What I have been craving desperately!" said Tiffany, with desperation in her voice.

"This office is soundproof?"

"Yes. Like every other office in this organization, as you very well know."

She jumped on him and began kissing him wildly. Jim kissed her back with equal passion. Her legs wrapped around him and his hands held her up. Their mouths worked against each other as they kissed again, deeply trying to suck each other dry. She fumbled and got down, immediately unbuckling his pants and opening the zipper. She pulled out his cock, all nine inches of it standing straight needing her attention. She began to stroke him and then sat down to take it in her ready mouth. All this happened faster than Jim could've responded to. Immediately, as he felt her tongue on his hard cock, he felt a shudder pass through his body.

"Oh! Fucking hell, Tiffany! How much have I missed you!" he began moaning with pleasure with his eyes closed.