Pleasing the Boss

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Chapter 43

Still drinking, we continue on with our game of truth or dare. Choosing truth, I ask Anna to tell one of her biggest sexual fantasies. She thinks long and hard about it.

“Umm, I think it would probably be having sex with people watching or having sex in public. It’s so taboo and the thought of it makes me nervous, but I think I’d love it.”

I force a giggle. I honestly can’t see Anna having sex at all let alone having sex in public. She’s a tough cookie at work, but she is the sweetest person I know. She has this innocent look about her, but I suppose that’s what makes her better.

After answering, she excuses herself to the bathroom while I grab another slice of pizza. Leaning against the counter, I look throw Spotify to find a new playlist and I hear Anna come out.

“Um, Thea.”

“Yeah,” I say with a mouth full of food.

“What are these? You were out of tissue so I looked around and these fell from your linen closet.”

When I turn around, my heart drops into my vagina. In her hand are three of my club masks. I knew I should’ve thrown them away, but they are too pretty to so I was collecting them to maybe wear again.

“Um, they’re nothing. Just costume stuff.”

“For what?”

Damnit, Thea, make up a lie. Think. Think. Think.


“What are you hiding? Tell me.”

“I…I can’t.”

“Why not? It can’t be that bad. They are just masks.”

“I know, but I can’t tell. I’m sorry.”

Anna’s light expression fades and I immediately feel bad for having to be secretive to her. She’s been nothing but open and honest with me. I told myself that I needed someone to talk to about all of this, but I don’t know if I can trust Anna not to judge me.

I watch as she sits the masks down on a side take and carefully steps over to her bed. Sitting down, she looks at me awkwardly.

“Sooo, what do you want to do now?” She asks.

I can already tell that the night has been ruined. Anna probably thinks I don’t really consider her my friend if I can’t even tell her a secret. It’s a pretty big secret, but still.

“I don’t know. We could just watch a movie, I guess.” She shrugs a bit and I feel worst.

“Ugh! Fine, I’ll tell you, but you have to keep it a secret!”

Her eyes widen a bit as she realizes that it must be a juicy secret.

“I promise. I won’t tell a soul.” She shakes her head and I grab a bottle of white wine. We’re going to need it for the secret I have to tell.

I pop open the bottle and start chugging, feeling the need to gain a little more liquid courage before spilling the beans. When I’m done, I pass Anna the bottle and she confusingly starts chugging also. We work our way through half the bottle within minutes.

“Okay,” Anna wipes the corner of her mouth. “Start talking, missy.”

“Okay. Sooo, Ethan and I have been going to a secret sex club together.”

Anna’s eyes widen in shock and suddenly a smile spreads over her mouth.


And so I do. I tell her everything little detail about my experience at the club. I even tell her about Kate and the sex. I tell her about Troy. I tell her about the masks. No detail goes untold and when I’m done, she’s fanning herself with a paper plate from eating pizza.

“Holy shit, that sounds so fucking hot.”

“It really is, but the Troy situation has kind of turned me off of the club a little.”

“I understand. He’s a total jerk, but there has to be a reason for it. No one just attacks someone in the middle of a club for no reason.” She shrugs.


“Sooo, when are you going to take me?”

“Wai,t what?”

“You heard me. I want to go one day.”

Oh, God, I’ve created a monster. How do I possibly tell Ethan that Anna wants to go to the club with us? He’ll say hell no in a heartbeat.

“Uh, it’s kind of exclusive. I’m not the person to talk to about getting in.”

“Talk to Ethan for me.”

I already know for a fact that Ethan isn’t going to let one of his employees go to a sex club with him, but I’m having a hard time telling Anna no. I shouldn’t have told her. I was too busy worrying about her judging me, but didn’t think about that fact that she may be interested. Too interested, apparently.

“I will, but don’t be surprised if he says no. You work for him and he doesn’t want to let the club life mix with his professional life. Please understand.”

Anna lets some of her enthusiasm fades and she nods.

“Gotcha. Just please talk to him.”

“Okay. I will.”

We continue on with our fun sleepover by eating more snacks and finally getting to those movies. Shutting off the lights, we crawl into our sleeping bag beds and start a scary movie. As we’re covering our eyes and yelping at the tv, I see Anna looking at me out of the corner of her eye. I can only imagine what’s going through her head at the moment. Is she thinking about the club or is she thinking about me? That body shot seemed a tad bit intense for her. I really don’t need another Kate on my hands. Speaking of, I haven’t heard from her in days. I’m not concerned or anything, but it seems a little weird for her. She used to text me on the daily.

I brush off the thought and give my attention to the tv. Anna and I manage to work out way through three movies before 3am hits and we’re completely tired. She helps me put off the snacks and food up before we slide down into our sleeping bags.

Lying in the dark, I hear Anna breathing softly.


“Yeah.” I reply.

“Thanks for having this sleepover. I really needed it. It may not seem like it, but I don’t have a lot of friends.”

“Neither do I. You’re my only friend.”

“For some reason that makes me feel a little better.” She giggles softly.

“No problem. I’m glad you came.”

“I wouldn’t have missed it for the world. I know when we first met I came off as someone who has everything together, but I don’t. It’s hard to balance work and play sometimes.”

I totally get where she’s coming from. There’s a very thin line between work and play, especially when you’re playing with the same person you work with.

“I completely understand. I hope we get to spend more time together. I know I got a little tied up with Ethan, but I realized that I do need a friend to talk to about girl things. It’s hard keeping it bottled up.”

“I agree.”

Even in the dark, I can tell Anna is smiling and it makes me smile. I like that she’s so opposite from Kate in the friend category. Kate always seemed like everything needed a sexual undertone. Anna just seems so genuine. However, she can’t hide the fact that she likes me a little, but I like that. I like that she can’t hide from her own feelings. I’m not saying that I’m going to try anything with her. I’m just saying that it’s nice to be around someone a little more translucent than Ethan and Kate.

The room falls quiet for a moment until Anna speaks again.



“Can I ask you a question?”

“Yeah, sure.”

“What’s it like….being with another girl?”

And here we go.

“Uh, it’s pretty good.” I can’t help but laugh a little. I can’t believe I’m having this conversation right now. I don’t even label myself as lesbian or bisexual. Sex with Kate just happened. I’m attracted to her and everything, but I thought it was just a one girl thing. However, here’s Anna and I think she’s adorably sexy.

“Hm. I like girls a little, but I’ve never been with one. Do they have that at the club?”

“Girl on girl? Absolutely.”

Now that I know that she’s curious about her sexuality, I honestly believe that the club would be the perfect place to explore that. It’s still not going to fly with Ethan, but it’s worth a try if it could possibly help Anna.

“Cool. I hope I get to go.”

Deep down, I do too.

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