Owen
She’s rubbing her neck and giving me these sweet, pouty eyes. My cock is straining against my pants, and part of me hopes she doesn’t notice.
There’s another part, a naughty part, a dark part, that hopes she does. There’s a part of me that hopes she absolutely does notice my bulging erection and that she likes it.
I hope she sees it and she likes it and she wants it.
And it’s wrong.
It’s wrong for me to think that way.
I’m no good for Lillian, so I don’t even know why I’m playing this game. Only, that’s not exactly true, either. I do know why I’m playing. I’m playing because it’s Lillian. I’m playing because she’s perfect and beautiful all the right ways.
There’s an innocence about her, a sweetness, and it draws me in. Like a moth to a flame, I can’t get enough of her. I can’t get close enough.
It’s easy for me to justify not pursuing her. I’m her boss, after all, and I’m a virgin. That’s weird to women. It’s weird and it’s strange and the idea that I’m waiting for someone I love, someone that I care about, doesn’t make sense to most people.
Somehow, I don’t think Lillian would be freaked out if I told her the truth about me. I don’t think she’d be upset if I confessed that I’m a 30-something virgin who has never met anyone worth fucking.
Anyone worth sleeping with.
Anyone worth making love to.
Until her.
Now, instead of telling her that I like her, that I want to date her, that I want to pursue her, I’m wimping out once again. I’m playing this game where I pretend to be ambivalent, when in actuality, I’m anything but.
I don’t want to be her friend or just her boss.
I want more.
Still, she doesn’t spend a lot of time flirting with me. She hasn’t done anything to lead me on. We shared one sweet, ridiculously romantic kiss at the holiday party last year, but then we both pretended it hadn’t happened.
Maybe she was tipsy and forgot.
Maybe I didn’t do a good job kissing her.
I’m not sure.
I should have taken a chance and asked her out back then, but I didn’t want her to feel pressured to go out with me. I flaked out. I got scared. It was only a kiss, and I worried I was reading too much into it.
Kissing her was the best part of my year.
Now, I’m finally ready to pursue her. She might break my heart, but I don’t care anymore. It’s a risk I’m willing to take. I’m finally ready to show her she’s the one for me. She’s perfect. She’s everything I’ve always dreamed of and even though I’m not perfect, even though I’m no good for her, I want a chance.
I want one shot.
I want to prove to her that I can be the man she needs me to be.
For weeks I’ve been working up the courage to ask her out. It’s stupid because I’m a lawyer. I’m good at dealing with people. I’m direct. I’m determined.
When it comes to her, though, I’ve never been more scared of rejection, and I think that makes me weak.
I feel like it makes me weak.
I know it makes me weak.
Tonight is the night, I tell myself. Tonight is the night when everything changes between me and Lillian. Tonight is the night when I show her I care, when I show her she’s gorgeous, when I show her how important she is.
Tonight’s the night.
She might reject me. There’s a chance. She might break my heart and tell me we have to be neutral colleagues, and I’ll deal with that if it happens.
But there’s a chance she won’t say that.
There’s a chance she’ll give us a shot.
“I don’t know if I know that,” she whispers, finally answering my question.
“You don’t have to whisper. It’s just the two of us here.”
“I know I don’t have to,” she whispers again.
“Then why are you?”
“It seems appropriate.”
“Don’t be scared of me.”
“I’m not. I’m just a little nervous.”
“Why are you nervous?”
“Because you’re you,” she says. “Because you’re Owen Westerluck.”
“You say that like it’s a bad thing.”
“It’s not, but I want whiskey.”
I pour her a glass. I hand it to her. She takes it and smells it, then sips slowly.
“It’s good.”
“Of course it is.”
“Aren’t you going to have some?”
I hold up my own glass.
“To the night,” I say.
“To us,” she says.
We sip our drinks quietly, slowly, then Lillian sits down at my desk.
“What are you doing?”
“I believe you promised me a game,” she says.
“I promised you a game, but you’re in my seat.”
“You have your rules and I have mine,” she says. “And rule number one is that I get to sit in your chair.”
“Is that so?” I ask.
“Oh yes,” Lillian says, and then she smiles brightly. Her happiness fills the room and for a minute, I forget about everything but making her laugh, making her smile, making her feel good.
“And where should I sit?”
She points to one of the chairs across from the desk, the ones my clients sit in.
“I think one of those will do. Don’t worry. You won’t be sitting for long.”
“What if I choose truth?”
“I didn’t think you were the kind of man to back down from a challenge, Owen. I’m disappointed.”
“I’ll never disappoint you, Lillian.”
She pauses for a long time. Something flashes across her face. A look of surprise? Understanding? Acceptance? I can’t tell.
But then she just nods and says, “I know. So what’ll it be, Owen? Truth or Dare?”