Page 5 of The Boss Dilemma


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“That’s the whole idea!”

I shake my head, adamant. “No way. The only place where this outfit would work would be a strip club, or a sex club or something. It’s completely…” I trail off, a flicker of alarm rising inside me as Jacquelyn nods excitedly. “Wait, what? You mean we’re going to a sex club? Oh, no. No way.”

“Oh, yes!” she crows. “You finally guessed it. It’s one of the most exclusive clubs in the entire city. You have to know a member to get an invite. And guess who I met at a party last weekend?”

I plop down on the edge of her bed. “An existing member.”

“You have to come with me,” Jacquelyn pleads, shaking the dress at me.

Can I even call it a dress? No. It’s fabric scraps, plain and simple. I hope she didn’t pay a lot of money for that, or she really overpaid per square inch.

“You have a reason to go,” I remind her. “And an actual invite. I don’t. And honestly, I don’t really know if I’m a sex club type of person.”

“You just need to give it a chance,” she shoots back, finally giving up on the outfit and rifling through the hangers in her closet instead. “I swear it will be good for you. You’ll forget all about Brad and your problems and everything else you’ve been worrying about.”

But now I’m worried about what exactly a sex club entails besides the obvious: sex. Will people just assume that I’m available if I’m there? How does it even work?

I don’t want to voice any of those questions in case Jacquelyn gets the wrong idea that I’m actually interested.

I heave a sigh and fall back on the soft duvet. Her apartment is small—a studio masquerading as a one-bedroom space—but it’s impressively decorated.

The lighting is warm and inviting, and I can tell Jacquelyn has had fun selecting the furniture and decor. It’s definitely leaning hard into the mid-century modern trend, but it feels like a home.

It tells me that Jacquelyn has been successful to be able to afford the rent in a city like San Francisco.

Successful and happy.

It’s useless to compare myself to my friend when we’re so different to begin with, but it’s hard not to. It makes me feel a lot like a failure to realize that I’m unsuccessful in both my career and in my social life.

Not to mention my love life.

I won’t know what to do if someone actually does approach me in the sex club. That’s how long it’s been since I was last single.

I dated Brad through my last year of college and then for the past few years after that. What does the dating scene even look like now?

“Fine,” I say suddenly, interrupting what has to be Jacquelyn’s fifth argument about why I should shimmy into something form-fitting and go to the sex club with her.

“‘Fine’ what?” she asks, brightening considerably. “‘Fine,’ you’re going to take a shot with me right now? Or ‘fine,’ you’re going to stop being so against having fun?”

I grimace, blowing out a breath. “Fine to both. To everything. To having a good time. But I’m not wearing that dress.”

“Yay! I have a ton of things for you to pick from,” Jacquelyn gushes, shaking an armful of hanging clothes in her closet. “Get in there. I’m going to go get our shots.”

It’s just a short dash to the kitchen, where glasses rattle around, but I’m already regretting my decision. Jacquelyn’s closet is so full of questionable fashion choices that I’m afraid I’m going to have to go back on my promise to go out with her. We got along fine in college, but even back then, she was more of a party girl than I am. I’m not sure we have the same definition of ‘fun’ anymore.

But I’m only going to be in San Francisco for a few days before I have to go back to Colorado and deal with unpacking the boxes of stuff that I hastily moved into the studio apartment I rented when I moved out of the place I was sharing with Brad. I should at least try to get out of my comfort zone a little while I’m here.

After perusing for a minute or two, I settle on a slinky black number that’s the most modest out of all her dresses. I tug off the comfortable jeans and t-shirt I’m wearing and slip it on quickly.

Unfortunately, I’m a bit curvier than her and so much taller that it only just covers my… uh, assets.

“Oh my god, perfect,” Jacquelyn gushes as she returns, thrusting a shot glass at me. “This is probably even better than the other one. You’re all legs. This dress will make them wonder what else you’ve got underneath it.”

“They won’t have to wonder very much,” I mutter, tugging on the hem.

“I guess I’ll just wear the strappy one.” Jacquelyn grins, holding up her own glass. “Now, cheers.”

We clink our glasses together and then drink. The burn of the liquor stays with me as Jacquelyn gets dressed and we finish getting ready. Then we take a cab across the city to the sex club, which looks, from the outside, like any other club, all flashing lights and velvet ropes.

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