Dominating the Boss 45 (Patreon)

“Why don’t you go to your girlfriend while I go and make a few arrangements,” I said to Jenny. 

“Why?” she asked, but I just gave her a pointed glare, and she walked away, leaving me in the corridor to make some arrangements. 

Dorothy’s enthusiasm suggested to me that she had no idea how a strip club actually worked, and I had no doubt that, if left alone, she would just go sit in front of the main stage. Which was bad enough under normal circumstances, but I had no intention of chasing away a bunch of horny idiots who would try their luck with the only free ladies in the club. 

Worse, the strip club staff wasn’t really equipped to measure and treat her for her spending capabilities, for one simple reason. The personnel was not really familiar with the female clientele enough to quickly assess her clothing and put a rough price tag. Three of them looked like a bored bachelorette party that decided to visit a normal strip club rather than a male one to spice up their night … often meant little to no spending. 

My situation was different. My clothing was significantly cheaper than what she had been wearing, but I ‘carelessly’ lifted my hand near a waitress, letting her get a good glimpse of it, letting her realize that it was not a fake. 

A five-figure watch was a good indicator of spending potential, especially when it fit well with my business casual clothing, signaling that I had other, more formal pieces in my collection. Luckily, the place was high-class enough to care about such stuff. 

She immediately gave a signal, and a manager — a sexy woman in her thirties who wore too much makeup for my taste — walked toward me quickly. 

“Welcome to our establishment, sir. How can I help you,” she said. 

I sighed as I pulled out my wallet, and pulled a nice bundle of cash, while also flashing my platinum credit card. “I want your best room, preferably with some soundproofing. Make sure to send your best dancers, and say them to keep the brunette happy above all others. Virgin cocktails only, but make sure they don’t mention it, or you’ll say goodbye to your tip,” I said, choosing to give her an explicit warning. 

Ordinarily, warnings about holding back the tip were a good way to get the worst experience possible, but not when accompanied by a preemptive tip as well. 

Together, they told my situation much better than words could. I was about to entertain an important guest, and no mistakes were allowed. 

“Yes, sir,” she said, her flirty attitude gone and replaced with professionalism, with just a hint of surprise. After all, while the ordinary customers generated a steady cash flow, there were two kinds of customers that generated real profit for such places. Young athletes with too much money and willing to show off, and entertainment aspect of the business side. 

The fact that our client was a young woman was just a small detail, easily ignored. 

With those orders delivered, I went to catch up with the girls, who, as I predicted, moved toward the main stage, uncaring of the hungry glares they awakened despite the strippers. I could already see five different men trying to talk with the bartender to send some drinks and try their luck. 

Luckily, I didn’t misread the professionalism of the manager, and soon, a sexy waitress arrived at our side. “Please, this way, sir,” she said as she started walking in front of us, our hips swaying. 

Dorothy’s eyes were locked on her hips for a moment, but her expression was not desire but jealousy. It didn’t surprise me, as I was able to read her lack of attraction to her own gender quickly, but it would have made the night much easier if I could just call a nice blonde — or two — to keep her distracted all night. 

“Wow, are all strip clubs this nice,” Dorothy said as she entered the room, though her expression was more disappointed than excited about that. “I thought they were supposed to be seedier.” 

“Sorry about that, but I’m an old man, and I like my comfort,” I said, happy to throw that as an excuse rather than trying to deal with the risks of a seedy club — especially the ones that were attended by real criminals and not just rich kids that think themselves as dangerous. 

I had no intention of calling a favor from one of my less-reputable friends to resolve the inevitable crisis that would follow. 

She looked disappointed, but luckily, not enough to push for her luck as I sat on the small couch in the corner. I didn’t like the way Dorothy was getting too touchy-feely, and it was better to put some distance without looking like it. 

I gestured for Natalie to take the seat in the middle, leaving the couch on the one at the right for Dorothy. 

Unfortunately, there was no single chair, as each was designed to allow at least three people — making sure the dancers had their range of movement during the lap dance, or accompanying the visitors with a drink. 

Unfortunately, it left me with an unwelcome challenge when Dorothy chose to ignore that seat arrangement and sat next to me. 

Which was something I was afraid of, but I hoped it wouldn’t be the case. Of course, I had thought to ask Natalie and Jenny to sit with me, which would have filled the couch … but would give the trick away, making it pointless. 

The whole point was to keep her happy without creating some unnecessary entanglements, a fact that started to get harder and harder as the night progressed. 

Admittedly, it was my fault. I treated her in the usual manner I dealt with my bosses and important clients. And, lost in my usual habits of managing the upper management with nonsense, I forget to factor in a very important fact. 

That I was catering to a young, impressionable woman, not too different than Umi, and somehow, she misunderstood the whole point. 

Ordinarily, it wouldn’t be a problem. She wouldn’t be the first twenty-something that entertained me for a few nights … but her position made it very difficult. 

Worse, she was a spoiled billionaire, and I had no idea how she would react to even a mild rejection — and I wasn’t willing to test that unless it turned too vital. 

Hopefully, the dancers would be enough to distract her. 

Before she could start talking, the door opened, and two entered. A waitress, carrying a large tray filled with a nice spread of cocktails and shots, each colorful. Accompanying her was a sexy pink-haired dancer with an ass to die for, dressed as a police officer. Clearly one of the top earners, the perfect sway of her hips to show her incredible skill. 

I was familiar with strippers as much as I was familiar with my scotch. 

Benefits of entering the world of business in the late eighties. 

Dorothy reached for the drink, but I was even faster, taking two shots quickly, making sure that they had no alcohol as I ordered. 

It was better to be safe than sorry. 

“First time in the strip club,” I said to Dorothy while Jenny talked with the waitress, no doubt asking for a virgin cocktail, not wanting her to see that communication. 

The waitress looked at me, and I nodded to her, telling her that it was okay to share the content details with Jenny. 

“Yes, it’s so exciting,” Dorothy said right after she took a shot as well, which I would have appreciated more without her hand landing on my thigh ‘accidentally’. 

Admittedly, my annoyance was strictly intellectual. On a more primal level, I was enjoying the attention she was showing. It was an amusing feeling to be wooed so directly by a sexy young woman. 

Meanwhile, Jenny looked at me questioningly about the cocktails, and I gestured to Dorothy, using a moment she chugged another shot aggressively to nod toward her, signaling to them that I was trying to keep Dorothy as sober as possible. 

Once again glad that they were smart enough to play along with just a clue. Jenny deserved a reward, and Natalie…

Well, she managed to earn back enough credit to make her punishment a fun one. 

Meanwhile, our pink-haired dancer started to move freely, a lean forward giving us a deep view of her cleavage. To my surprise, despite her insistence on dragging us to a strip club, Dorothy reacted to the view with a surprising blush … showing that she was not exactly ready for it. 

Good, I thought even as I caught her gaze and smiled. “It’s customary to watch the dancer, or they’ll feel neglected,” I said, goading her.

“R-right,” she stammered, and followed my suggestion, but not before she took another shot, unaware that she wouldn’t find the courage she expected at the bottom of those drinks. 

Soon, she would overwhelmed with her shyness, use her meeting tomorrow as an excuse, and leave. 

It was a foolproof plan. 

But then … why was I feeling like I had forgotten something really important…