Chapter 33

“Cool!” Then in a goofy voice, he mimics a fictitious customer like he’s in a diner. “Pardon me, but I’ll take the Sausage and White Gravy Lunch Special please.” In many ways, Will is an old soul with a calm demeanor and maturity, but I like it when he shows his youthful side too. It lets me know he’s relaxed and being himself; another quality that makes him so attractive in his own special way.

“Do any of the guys ever get pushy, or ask for more?”

“No, they’ve all been really nice. I did have one that wanted to check out my ass.”

“But I thought you didn’t do anal?”

“I don’t. He just wanted to kiss and lick my asshole; I was fine with it. Should I not be letting clients do that?”

“No, it’s fine. If you’re okay with the fun, then all’s well. But remember, Anal Play is technically an extra they should be paying for.”

“Gotcha.”

“Are there any aspects you find more difficult than others?”

He thinks for a moment, then says, “Keeping my ego in check. Three months ago, girls barely knew I existed ... and, yeah, I know part of it is my fault for being so introverted. But going from my only sexual activity being jacking off and self-sucking to now having all kinds of—”

“Wait, what?” I interrupt him. “Did you just say self-sucking?”

“Yeah,” he grins, “it’s kind of a hidden talent I have.”

“Really! I’m intrigued. I would love to see you do that.”

“Okay, but how about later? I’m still recovering from...” he waves his hand over his parts, “ ... you know.”

“Absolutely! I’ve heard about guys that can do that, even watched videos online, but I’ve never actually seen it for real.” This kid is full of surprises - fun surprises as I’m continually discovering. “Anyhow, go on with what you were saying.”

“For me, going from a nonexistent sex life to now having all kinds of people wanting to touch me, suck me, and have me fuck them is surreal. I feel like an overnight mega-rockstar or something. Daisy and you both warned me about not letting it go to my head and I completely understand that, but, damn, it’s harder than I thought. It’s like I’m walking around with a magically charmed penis in my pants that suddenly everyone wants.”

“And, that’s exactly how it is for escorts,” I concur. “For the girls, it’s their charmed pussies, asses, and boobs. This profession definitely has its own unique traits; once you put yourself out there in this manner, it seems like everyone wants you. So, yes, your ego must be kept in constant check. I’m not saying don’t enjoy the special attention, but always stay professional about what you do.” With that, I give him another squeeze. He’s still rock-solid if you can believe it! I’m sure my hand never letting go has something to do with it. “Trust me, Will, you’re on the right track and have nothing to worry about. Just the fact that you’re aware of potential ego issues tells me you’re being smart about it.”

“Thanks,” he grins, “but please tell me if I ever start getting a fat head and going off the rails.”

“No worries, that’s my job.”

In the real world, a forty-some-year-old superior having her newest, and much younger, employee at her house alone would no doubt be a strong case for raised eyebrows. And this is not even taking into consideration that we’re naked and what I just swallowed! The good thing is my other employees won’t be jealous because I’ve done these same things with every one of them, and will continue to do so. I deeply love all my girls, and now my one guy.

This service we provide thrives in its own reality and flies completely under the radar of what’s deemed normal, or conventional in the real world. Not to mention moral. My company provides companionship specializing in sexual interaction and satisfaction - for a price, of course. Being chief executive of such a business means I must ensure the services we offer are everything we advertise; in other words, I make it my duty to sample our product. You could say I’m not only the CEO, but also the head of Quality Control.

Maintaining this type of employer/employee relationship like no other company would dare definitely has its rewards and benefits. I make it a point to have every one of my escorts come here and have the time of their lives because they more than earn it. This beach house may be in my name but it’s for all of us, we built this. Every morning I’m amazed at this crazy life I find myself in, but I wouldn’t trade a second of it for anything.

Am I nothing more than a high-class pimp disguised as a professional businesswoman? In some people’s eyes, perhaps, but we operate at a professional level of discretion well above such a street-thug mark. Our escorts are qualified, healthy, clean of STDs, drug-free, and hold no criminal records. It happens that we live in a time and location where the world’s oldest profession is deemed illegal; I am not here to debate morality and laws, just do my best to quietly skirt around them without detection.

How does the old line go? Loose lips sink ships. Every day we run the risk of a client or an escort saying the wrong thing to the wrong person. As touchy as this sounds, it’s not as bad as one would think. We have many state and federal-level law-making politicians in our customer base, thus making them benefactors of the club. Needless to say, remaining discreet is in their best interest as well. See how well all things work together?