Dominating the Boss 44 (Patreon)

Corporate retreats had certain times that they could be fun — my adventures with Umi were the evidence of that — unfortunately, that concept of fun didn’t extend to the extended event dinners, where most of the upper management had to go and brag about how successful the company was and how amazingly generous the company was to share that opportunity with people like them… 

Unfortunately, as one of those members of upper management, that included me as well. 

Ordinarily, I might have found a way to skip it, but when the heiress of the company suddenly decided to crash the party, it was not exactly the best strategy. So, I went there, putting on my best fake-enthusiastic face as I bragged about the great things we achieved, and promised everything short of another moon landing for the next year before I took my seat. 

Face time with the owners was never to be missed. 

After all, the truth of the upper management was like being a magician. There were a lot of tricks, smokes and mirrors, and skill, but the biggest asset was to have a willing audience, ready to engage with the nonsense of the management. 

Amusingly, it didn’t matter if they were just lapping whatever I told, or trying to disprove it. A magician’s best friend was the people who tried to unravel his tricks while watching his show, allowing the misdirection to happen. 

Hence, I did my best to look affable and wise for the daughter of the owner — an old owner who would eventually end up in the dirt, leaving the company to her. 

I didn’t expect to be too successful. 

“… it’s a fascinating breakdown of the five forces. What a novel way to approach market analysis,” Dorothy said as she took another sip of her wine, her voice a touch too cheerful, showing that she was tipsy and not drunk. 

Which, annoyingly, made her enthusiasm toward the business theory even more unbearable. She was just like every graduate that had just left the business school, thinking that they had suddenly learned the true meaning of success…

No question why most of them ended up doing nothing worthwhile as a part of huge internationals rather than building their own companies and getting rich. 

I didn’t tell her that. Instead, I had responded to her with all the bullshit I had learned after a lifetime of working with management consultants, salespeople, and other legal conmen, and she ate that nonsense up. 

She was an overeager fit brunette, the kind that I enjoyed seducing and breaking down — Umi being a great example — but unfortunately, her identity made her too much of a troubling target. 

There was something as too much risk, so I played along, even sending a warning glare to a waiter and sending him away when he came to replenish the wine. 

Unfortunately, the waiter was incompetent enough to be seen on his way to retreat. “Another bottle,” Dorothy called, which he brought despite my warning gesture, costing himself a huge tip. 

When her speech ended, I caught Natalie’s gaze and called her to the table, accompanied by her beautiful long-term girlfriend. 

Who had carried a little gift from me? 

They were a good way to distract Dorothy while I extracted myself from the situation. 

“Oh, lady of the hour is here,” Dorothy said as she poured a glass of wine to her, and was about to pour one to Jenny, only to be stopped with a gesture. “Sorry, I forgot about pregnancy,” Dorothy said with a blush.  

“Don’t worry, it’s easy to forget when looking at her,” I said, smiling softly as I gave an exaggerated look of appreciation … though I didn’t need to fake it. Wearing a sexy green dress that was just loose enough to cover up the tiny bump she was developing, Jenny looked incredible, especially with her cleavage displaying just the perfect amount of her pregnancy breasts to attain a tasteful sexiness. 

“Thanks, you’re always so sweet … when you’re not being sexy,” Jenny said as she leaned down and kissed me on the lips, too long to be a playful joke, no doubt encouraged by the location of the table that allowed us to stay hidden from the crowd due to some clever placement. 

Natalie flinched, understandably so as she received a pointed gaze from me. One that lasted only for a moment, but conveyed a long punishment. 

She clearly forgot to prepare Jenny about the identity of Dorothy. 

A huge strategic mistake, one that could ruin all the work I had been putting into the situation. I couldn’t look like a degenerate who was having an affair with the girlfriend of my direct manager. 

Being one was not the problem. 

I just couldn’t look like it. 

I threw another warning glare to Natalie, one that suggested her solve that immediately. Unfortunately, Dorothy’s angry blush suggested she wanted to talk that immediately. 

I decided to preempt that. “Thank you for being such a loving person, Jenny,” I said even as I turned my head in a way Dorothy couldn’t see, and mouthed her to play along. Luckily, while she could be too trusting at times — a fact that both Natalie and I used to our benefit more than once — she was still smart. 

Certainly smart enough to know that I wouldn’t look alarmed for nothing. 

Then, before the tipsy heiress of the company I worked for could explode, I made a point of leaning down to kiss her belly. “It makes me proud to be the sperm donor of the beautiful baby you will raise together. And it’s beautiful that you want to keep me included in the baby’s life and make them feel loved by a father as well as two mothers,” I said. 

Jenny’s eyes widened, not by love, but surprise as she turned to look at Dorothy. She knew me well enough that I hated acting like this … and only someone really important could make me act like this. 

“Oh, I didn’t know that. Such a beautiful way of building a family. How beautiful,” Dorothy said, her tipsiness working to our benefit. “You’re such a nice man for making such a sacrifice, Nathan,” she added as she put her hand on my shoulder. 

“Please keep it a secret. We don’t want the rest of the company to know. You know how closed-minded and bigoted people could be,” I said, with absolutely no problem misleading her about the nature of my fears. 

Whatever it took to keep her from suddenly digging around morality clauses. I trusted my contract to hold, because ultimately, it was something that was pushed by a penny-pinching CEO. She wouldn’t escalate the situation that would result in a lengthy legal battle that would cost the company ten times the money. 

That didn’t apply to Dorothy. A few extra million in legal costs wouldn’t matter to her. 

Rich and idealistic was a dangerous combination. 

Luckily, she was also determined to prove herself as progressive, making her easily swallow the situation rather than poking it too much, like why Jenny was giving open-mouthed kisses to their sperm donor in the middle of a company event. 

I sat back, and Natalie managed to whisper a few details while disguising it as flirting, and we went back to the safer topics. Since I had my scotch, I couldn’t drink wine without being suspicious, and Jenny was pregnant, so the task of keeping Dorothy sober for her flight fell on Natalie, making sure to drink most of the bottle. 

“Maybe we should call it a night,” I said as I looked at Dorothy, remembering that she had mentioned something about a flight. “You have your flight, right?” 

“Oh, you remembered,” Dorothy answered, her slightly smug smile suggesting she had misread the nature of my understanding.  Worse, she put her hand on my arm playfully, flirting a little. She had been shy at first, but as the night progressed, it continued to change. “But don’t worry, I canceled the flight and called for my private plane. I can stay a while more.” 

“How fascinating. I was afraid that I had to cut our discussion short,” I said, keeping my expression straight, and suppressing my annoyance about the extension.

I might have had a lot of practice playing to the veneer of the rich and the incompetent, but Dorothy was just young and enthusiastic enough to make it a real chore. Worse, getting her drunk and letting her loose in a strip club was not an available hospitality strategy. 

Another hour, and most of the employees were gone, leaving our concealed table the only one while Dorothy did her best to flirt with me without being too obvious. Luckily, at some point, Jenny decided to keep me entertained by playing footsie. And, as a pilates and yoga trainer, she knew exactly how to use her feet to the best effect as she rubbed my bulge. 

“I can’t believe how amazing it is talking with you. Most of the board is filled with stuffy old white men, who think they always deserve the best. They are so greedy and sexist, not to mention incompetent and boring,” Dorothy complained, unwittingly targeting me. Lucky, I thought that description pretty accurately described me — except the incompetent and boring part, of course. 

Worse, she wasn’t drunk, just excited. We nodded, hoping that she would end the night. 

“You know what, follow me,” she suddenly said and stood up, walking away with all the confidence a young entitled woman could exude, not even bothering to ask about our opinion. Natalie followed immediately, while I acted gentlemanly and helped Jenny to stand up.  

“We can probably excuse your disappearance,” I whispered to Jenny. 

She shook her head. “No, I rather follow her. And, we can always bail later using it as an excuse,” Jenny said. 

“You’re the best,” I said, cupping her ass as I kissed her. 

“And you’re so bad. Never missing an opportunity to cup a feel,” she said, but her giggle showed that she didn’t mind. 

We caught up with them in the corridor and followed Dorothy … until she stood at the entrance of a strip club. “Let’s end the night just like those stuffy old men,” she said as she walked inside. 

Helpless, we followed.