Jack and Diane

This story was inspired by "Tough Love," a 2012 story by graymangazer in which a husband down on his luck lets himself be controlled and eventually enslaved by his wife and her boss. While the initial premise and some of the original set-up is very similar to that story, the rest is completely different, with a different story line, different characters and of course, a different ending.

Thank you for all the comments and feedback on my previous posts and I sincerely hope you enjoy this story. For those who are wondering, yes, I am working on the next chapter in the "Revenge in Advance" saga... And please remember, this is a work of fiction.

*****

Jack Ketterer watched as workers cleared the last of the furnishings out of the building once owned by Ross Holdings, the company where he and his former wife, Diane, both worked. He smiled as he took pictures of the items being moved out of the building, knowing he would use them to humiliate David Ross, the former CEO and founder of the company now paying his debt to society along with Diane.

It started innocently enough. Diane once worked for Jack as his secretary but he and others saw something in her, mentored her and before long, she was his equal. They took an instant liking to each other and despite her being several years his junior, got married after a months-long engagement. Life, at least as far as Jack was concerned, was perfect. He had the perfect job, the perfect wife and everything else fell into place.

That is, until the day Jack lost his job. He was told it was because of the recession and given a hefty severance package. That, along with the monthly dividends he received from a huge trust fund set up by his grandparents, kept their heads above water. Jack approached Diane about contributing to the household budget, but she balked, claiming that she would take care of it if only he would give her control of the finances and his trust fund.

That surprised Jack, who saw his marriage as a corporation made up of two equal partners. So much for that, he thought. Perhaps it was a good thing that his parents made her sign a prenuptial agreement that kept her away from the trust.

The job search was also not going well for Jack. He would get interviews but was always told the same thing - either he didn't have the right skill set or they needed someone with more experience. It all sounded like bullshit to him, making him believe that someone was blackballing him.

Then he learned that Diane had been given a promotion and hired someone to take his old job. That didn't sit too well with him at all.

"Dammit, Diane, that job meant so much to me. Why couldn't you at least give me a shot at it?" he asked.

"Fuck off, Jack. It's not my fault you lost your job," she said. Her tone softened after she saw the look of shock on Jack's face. "I'm sorry, Jack. Look, let me talk with Barbara in HR and see what we can come up with, okay?"

"Thanks, Diane," he said, "I appreciate it."

A few days later, Diane approached Jack at the dinner table.

"I talked with Barbara and she said Ann really needs someone to take care of the files in the cave. It's not much, only minimum wage, but at least it would be a foot in the door and you'd have some benefits again."

"Thanks, Diane, I appreciate it. At this point, I'd take just about anything. You mentioned benefits. Am I not already listed on your benefits?"

"Well no, Jack, you lost your benefits when you lost your job and I haven't been able to add you because the open enrollment period hasn't come around again," she said. Jack accepted that for now but wondered to himself why she wouldn't have listed him when she first got promoted.

"Also," he added, "didn't OSHA declare the cave unfit for human habitation?" The "cave," as it was called, was a dark, dusty airless basement that was freezing cold in the winter and unbearably hot in the summer. It had been a bone of contention with state and federal environmental agencies since there were still pipes covered in asbestos and the company refused to get the hazardous material removed due to the high cost of remediation.

"Well, you can clean it up and make it work," Diane told him. "By the way, if you accept the position, you will start Monday, right after the annual company gala."

"I'll take it for now, at least until something better comes along," he said.

"What, you're not going to stay there after everything I went through to get you that job?" Diane asked.

"Well, no, Diane, I'm not staying in a dead-end minimum wage job in a death trap for the rest of my career. You honestly didn't expect I would, did you?"

"Maybe not," Diane said quietly. "I just thought you might show a bit more appreciation for all I've done for you. It wasn't easy getting this set up for you."

That Friday, they attended the annual corporate gala and listened as David announced a banner year for the company. Max Schell, the chairman of the board of directors, also gave a toast, thanking everyone for their hard work and dedication to the company. He raised his glass and looked directly at Jack with a smile on his face.

Jack's attention, however, was on his lovely wife, who wore a short satin dress with nothing underneath. He couldn't wait to get her home so he could sample her freshly shaved pussy.

After the speeches and accolades, Jack was approached by a former co-worker who said he had questions about one of his old accounts.

"Good grief, this is a party," Jack said. "Can't it wait?" Diane waved him off, promising to be there when he got back. Jack grabbed his drink and headed out. Looking back, he saw David approach Diane.

"What is the sexiest woman in the company doing sitting here all by herself?" David asked. "Doesn't Ketterer know how dangerous that is?"

"Fending off the assholes trying to hit on me," she said as she turned to face the man behind her. "I'm sorry, Mr. Ross, I didn't know it was you."

"That's okay, Diane, no apologies necessary," he said, sitting down next to her. Diane took in the older man's sudden closeness, noticing the power and confidence he exuded. He wasn't the best-looking man, but there was an air about him that intrigued her.

"Wouldn't your wife take exception to you hitting up on another woman?" she asked.

"I'm not married, but some would say I'm married to the company," he said.

"How boring," Diane responded. "What about love, family, children?"

"I have everything I could ever need - power, money, prestige, you name it. If there's something else I want I just take it," he said.

"And what do you want now?" Diane asked.

"Why, you, of course." Diane laughed.

"What, you think that because you're the boss you can just take someone's wife?" she asked.

"You misunderstand me, Diane. Actually, I find that while I can just take what I want, sexy women included, I find it more interesting and fun to get people to give me what I want, willingly," he said. "Have you ever heard the old story about the frog?"

"I'm not following you," Diane said.

"If you take a frog and throw it into hot water, it jumps out. But if you take that same frog and put it in cold water, then slowly turn up the heat, by the time the frog knows what's happening it's too late. The same thing applies to men. Just put the right amount of pressure on the right place at the right time and before you know it, he'll happily give you everything he has - even his very right to exist."

"And who is it you're looking to 'cook' now?" she asked. David pointed at her husband, Jack.

"Your husband, actually," he said. "And I'd like you to help me in my little experiment."

"Oh really?" Diane asked. "You obviously don't know my husband very well."

"Tell me, Diane," David said, "How's his job hunting been going? I know it hasn't gone well and I also know he's decided to take you up on your offer to work in the cave. Haven't you ever wondered why he hasn't been able to secure something better by now?"

"I figured it was the recession," she said.

"Well, that may have played a role, but the truth is, I've been doing little things behind the scenes to sabotage his job hunt. Nothing illegal, mind you, just dropping little hints," he said. "Besides, who do you think laid him off to begin with? And who do you think promoted you?"

"Why would you do that?" Diane asked.

"Well, call it collecting on an old debt. Also, because he has something I want," David said. "You, for starters. And then there's that trust fund of his. Has he told you that it's worth more than 500 million dollars?"

"Yes, he told me that when we first married," Diane said. "But he only gets monthly dividend checks and it's set up so that no one, not even me, can get it. Are you telling me you want him to willingly give you his money? Is that what this is all about?"

"Well, yes and no," David said. "Actually, I want him to give you that money, and I'd be lying if I said I wouldn't appreciate a good chunk of it. But like I told you, I'm after something else. Think about it, though. Working together, we can get him to give you everything he has. You would have complete control over him - his money, his possessions, even his life. And he would give them all to you without reservation. In short, he would be your willing slave. What do you think?"

"I think it's time I took my husband home. This has all been very entertaining, Mr. Ross, but I'm not someone to do that to my husband."

"Just think about it, Diane. We'll talk later."

Diane thought about what David said the whole way home. She didn't want to hurt her husband, but something about David's proposal hit a nerve. She could finally have everything she wanted, plus a husband completely under her thumb. And she wasn't stupid. She knew David wanted her body as well, but he wanted Jack to willingly give her to him.

"Penny for your thoughts," Jack said to Diane after they made love that night.

"Jack, tell me again, how much is your trust fund worth?" she asked.

"I've told you before, Diane, it has a total net worth of more than 500 million dollars. Why?"

"I'm just curious. With all that money, why are you willing to work for minimum wage? Why aren't you working for your folks? Maybe you could start your own company," she said.

"I thought about that," I said. "I could have gone to work for my Dad and I still might. I just wanted to know if I could make it on my own. I don't want to get a job simply because I'm Frank Ketterer's son. Also, I wanted to get some experience outside the family business."

"I see," she said. "And who gets the trust fund if something happens to you?"

"There's mechanisms in place to ensure it remains in the family in the unlikely event something like that happens. Why? Are you and David plotting my demise?"

"Oh, no," she said. "Don't be silly. I love you. Don't you trust me?"

"It's not about trust, Di," Jack said. "It's about protecting what more than two generations of my family worked so hard to build.

"By the way, I saw you talking with David tonight," I said. "What was that all about?"

"Nothing, really, just small talk," she said. "Why?"

"Just be careful with him, Diane. I don't trust him. You know he used to work for my family before he started his own company?"

"I didn't know that," she said. "What happened?"

"Don't know. Dad never said anything but I know he and my mom hate his guts. He warned me to keep an eye on him. Seriously, Di, watch yourself with him. He's slick and I've seen how he gets people to give him what he wants," Jack said.

Diane wrapped her arms around Jack. "I'll be careful, Jack, promise. I do love you, please remember that."

"I love you too, Di. Goodnight," he said, holding his wife tight. His mind was now racing, wondering what David had told her. He finally drifted off to sleep.

Jack spent the next week cleaning up the dusty, asbestos-ridden death trap he was expected to work in. He removed several bins of dusty, dirty old empty boxes along with the remains of dead rodents and fixed up his "office," which was really nothing more than a broom closet along one wall.

Afterwards, he went to the gym, where he worked out with Jake, a security guard he had known for years. He and Jake would often grab a beer at the pub next door before calling it a night. On Wednesday, Jake handed him a flash drive.

"You'd better take a look at this, Jack," he said. That night on his computer, Jack learned his life and his marriage was effectively over.

Earlier that day, Diane received a summons to David's office in her email. She knew what it meant, and realized that she had to either obey or be destroyed herself. She made her way to his office where she was immediately ushered in.

"Come in, Diane," he said, ushering her to a chair in front of his desk. "Would you like a cup of coffee?"

"No, thank you, I'm fine," she said.

"Have you given any thought to what we discussed earlier?" he asked.

"Not really, Mr. Ross. I thought you were just thinking out loud. I didn't believe that you were serious."

"Oh, I'm very serious, Diane. And believe me, I'll make it all worth your while."

"Just for the sake of argument, what would you do?" she asked. He sat back, smiling.

"Well, most of what I might do would just be background - sabotaging his accounts, that kind of thing. You would be the one doing the real work."

"Like what?" she asked.

"For starters, you would cut him off from any sex whatsoever. On top of that, you would humiliate him, publicly if at all possible, yank his chain, if you will. Make him feel worthless. Put down his work product when you can. You see, a man's ego is based essentially on two things - his work and his , um, manhood, if you will. If he's made to feel that he's worthless as a worker and worthless as a man, he'll agree to pretty much anything."

"David, I'm curious about something," she said.

"Sure. Anything."

"Jack said you used to work for his family. Is this some kind of revenge for something that happened back then?"

"Well, that might play a role in this. I'm curious to see if your husband is half the man his father was back then. Of course, I didn't have the resources then I do now. And I certainly didn't have you. Does that make sense?" he asked.

"Yeah, I think so," Diane said. "So it's not just Jack you're going after. It's his family as well, isn't it? Maybe even his family's business."

"You are a very perceptive woman, Diane," he said. "Together, you and I can end up controlling a multi-billion dollar empire. Including Ketterer Industries."

"What would I need to do?" she asked.

"Spend his money like there's no tomorrow. Make him go broke if you can. Like I said earlier, cut him off from any sex, humiliate him as much as you can. Treat him like dirt here at work. I'll make sure he answers directly to you. Just keep putting on the pressure and eventually, he'll sign over everything to you. His money, his trust fund, whatever controlling shares he may have in his father's business, everything. He'll be completely reliant on you for everything. At some point, I'll fire him. Then you can find something really demeaning for him to do. Maybe I could hire him on as a janitor or something."

"And if I refuse?" Diane asked.

"Something tells me you won't refuse," David said. "Besides, I think you're too smart to turn me down. Once you get a taste of the power only I can give you, you'll want more. If you agree, you'll get another promotion, effective immediately, along with a 100 percent raise. You'll answer only to me, and everyone else will answer to you."

"What makes you think you'll be able to get Jack to do what you want?"

David pulled out a small brown bottle with an eyedropper.

"This," he said. "It's an enhanced version of a drug used to transition men undergoing gender reassignment surgery. One drop of this every day and in a few weeks, Jack will be more female than male. His penis and testicles will shrink to nothing, he'll lose muscle mass, get weaker over time and even develop breasts."

"What?" Diane asked. "Isn't that illegal?"

David shrugged his shoulders. "Maybe, technically, but no one has to know. Remember what I told you about the frog? By the time Jack realizes what's going on, he'll be so emasculated he'll do anything to keep you happy. Even sign over his entire life to you. You will control him completely, mind, soul and body."

"Is it reversible?" Diane asked. "I'm not going to hurt my husband."

"As long as the antidote is given within the first six weeks, yes. Beyond that, he may as well go through with the surgery and become a woman.

"Once he's signed everything over, you divorce him. File for 'irreconcilable differences.' In addition to what you already have, you'll get half of his entire fortune. And Jack will finish life as a woman. Maybe you could hire him - or her - on as a domestic servant."

"And what would I have to do?" Diane asked.

"I think you know," David said.

She knew, alright. She considered her options. Either go along with David and hurt her husband temporarily until she gets what she wants or face David's wrath. In her mind, she reasoned that if she went along with David in the short term she could buy enough time to get Jack out of harm's way. She loved her husband, but, she admitted to herself, she loved the idea of power. And if she could stick it to his family - the family that made her sign that stupid prenuptial agreement - so much the better.

"Okay," she said. "I'll do it. When do we start?"

"How about right now?" he asked. Diane nodded her head, stood up and began removing her clothes. Once naked, she walked around his desk and stood in front of him. He stood up and faced her. She dropped to her knees, unzipped his trousers and pulled out his semi-erect cock.

She loved sucking her husband's cock, and this was only the second one she had ever seen up close. He wasn't any bigger than Jack by any means, but it was attached to a man with power, not a minimum wage loser like Jack. She opened her mouth and took him in, giving him the kind of blowjob she usually gave her husband, even swallowing his load.

She wiped her mouth and perched herself on his desk, opened her legs and offered her shaved pussy to him. He smiled and drove his still-erect penis into her wet pussy, fucking her to orgasm. After filling her with his seed, he took her left hand in his, looked at her wedding ring and, taking his cock out of her, anointed it with his semen. She smiled and licked the gooey liquid off her diamond ring as he pulled his trousers back on and motioned her back to her chair.

"Tomorrow, you report to your new office, which happens to be right next to mine," he said. "I expect you to wear short dresses or skirts with nothing underneath, and of course, no wedding rings. There'll be no pictures of your husband and nothing to remind yourself that you're married. I also expect that we'll get together at least three times a day to, er, go over the day's business, if you know what I mean.

"Additionally, I expect you to give Jack a drop of this every day," he said, handing her the bottle. "It's odorless, colorless and tasteless so you can put it in anything - water, coffee, food, anything. One drop and one drop only every day. Any more than that and he could have a stroke or a heart attack. Any questions?"

"No," Diane said quietly, realizing that she had just cheated on her husband for the first time while agreeing to destroy him as a man. The guilt ate at her, but only until she thought about the power she would eventually get. David always followed through with his promises, she thought.

Jack felt as though he had been punched in the stomach as he watched his "loving" wife agree to help David destroy him while sealing the deal with her body. Worse yet was the pain he felt watching David smear his cum on her wedding ring as his wife smiled - the ring he gave her as a symbol of their union on the day she promised to forsake all others for him. Jake put a hand on his shoulder and offered him another beer.