“Show me what panties you’re wearing today, since you decided not to wear the ones I assigned,” Asher says.
I had no idea what he’d say next, but I certainly didn’t think it would be that. I hesitate, my heart pounding in my chest.
I was fooling myself to think I could waltz in here and tell him I wasn’t ready to be his… whatever… in addition to his mentee. Obviously it’s both or neither.
I really want to explain to him that I’m open to the idea of taking this… relationship… to another level, but that I’m not quite ready yet. But he hasn’t let me. It seemed he was about to kick me out of his office— fire me?— but now he’s telling me to spread my legs.
I have to admit, I’ve been so turned on since I entered his office. Hell, I’ve been turned on ever since I’d discovered the black lingerie in the envelope, or even before that— when I was first chosen as his mentee.
There’s something exciting and mysterious about it all and I don’t know why I can’t just give in to my baser instincts and go with it.
“Madilyn, did you not hear my instruction?” Asher asks me.
I realize I haven’t said anything. Or done anything. I feel frozen, over- thinking everything as usual.
“I’m obliged to explain to you that what goes on between you and me— or what doesn’t— has no bearing on your job. You received the firm’s offer to be an associate, and you accepted it. Your job security here at the firm, like any other associate’s, depends only on your job performance and input from all the firm partners.”
I nod.
It’s good to know he’s not going to fire me no matter what I choose to do. But it doesn’t help me figure out if I want to do… this… or not.
“You seem nervous,” Asher says, giving me a sly smile. “Let’s play a game.”
I just look at him, surprised yet again at this suggestion.
“I like games,” he tells me. “Games have rules. Games have winners and losers. Do you like games?”
I want to shrug, but I nod.
He seems to take that as a good sign.
“The game is that if I guess the color of your underwear, you have to show me.” His smile turns playful, almost innocent looking. “I only get one guess. It’s winner take all, or nothing.”
“Okay,” I say, before giving myself time to think it through.
I don’t want to give my brain time to take over my emotions and actions, like it always wants to.
I think I have good odds of winning this game. I doubt he will guess the color of my underwear. He probably thinks white or pink. But I can’t help but silently root for him anyway.
There’s something plaintive and hopeful in his voice, in his eyes. He comes across as tough and powerful, but I feel something lurking just underneath.
Some vulnerability of some kind, or some need for me to be vulnerable with him.
My head says no, but my panties are already soaking wet, and I know that if they had a voice, they’d vote yes.
“Red,” he says, with a big grin on his face, as if he knows he’s right without needing any confirmation. “Your panties are red.”
“How did you…?” I ask, but he shakes his head.
“No. We had a deal. Show me.”
I part my knees, which I now realize I’ve been dying to do ever since the first time he’d asked me to.
“I can’t see.”
I raise my skirt, showing him my red panties.
“That’s more like it. What do you say?”
“Yes, Boss.”
He stares at my red panties as I spread my legs wide for him and I can’t help but feel self-conscious. I wonder if there are any telltale signs of my desire for him, despite my best intentions to keep it hidden. Is my clit engorged? Do I have wetness seeping out of me?
“Come here,” he says, and I realize it doesn’t matter if he can tell just by looking. He clearly wants to find out by touching.
I stand up and walk over to his side of the desk, as if in a trance. An excited, yet slightly humiliated one.
“Yes, Boss.”
“Keep your skirt up, so I can see those red panties.”
I do as I’m told.
When I’m standing beside him, he pinches my clit, hard and without hesitation, as if it’s what he’s been wanting to do all along.
And I realize it’s exactly what I’ve been wanting him to do all along too. It feels so good and so satisfying to give up my power and control to him. I want him to keep going but I remain obediently silent.
“I wanted to talk to you while you were wearing the outfit I gave you,” he tells me.
His fingers press on my clit, through the lacy material of my underwear.
“I don’t know why you chose to play games with me,” he says, “when you obviously want to do what I command.”
He looks at his finger, which I can see is dripping with my wetness. And then he places back into my panties, closer to my opening this time.
“This is your punishment,” he says, as he pinches my clit and my hole with his finger.
I stifle a moan. All I want is for him to pull my panties to the side and finger me. And then I want him to do a lot more to me.
But he doesn’t. He just plays with my pussy through my underwear. It’s hard and rough, and I love it.
“We were going to have a nice chat about your thoughts and questions having to do with my cases,” he tells me. “We were going to work on things together and build a mutually satisfying relationship. I was going to be your mentor. And you were going to be my pet.”
He pushes his finger into me, but it’s still on top of my underwear. I can see now that he’s not going to give me what I want. And it’s all because I didn’t give him what he wanted. Which was for me to be his pet.
The “P” file.
It makes sense now. I hadn’t billed any time into it. And it appears that now I never will.
He’s still playing with my clit, and I’m close to coming. I moan, my lips parting for him like my legs just did, obeying his every command and responding to his every move.
I’m so glad I gave into him. I’m so glad he’s playing with my pussy. I’m so glad I’m about to come…
But he doesn’t let me. He removes his hand just as I approach climax. As if he knows my body better than I do.
I exhale, trying hard not to whine.
I want to say Please, Boss. More, Boss.
But I don’t. I know he would deny me and I already feel stupid standing here with my pussy dripping wet for him and my need for him as exposed and vulnerable as my body is.
He spanks my clit, hard but not too hard.
And then he says, “It was nice working with you, Madilyn. But I need a mentee who can follow directions. I’ll talk to the partners about having you reassigned.”
“I. But—”
My projects. His cases. All that time I’d spent working for him last night. My near orgasm.
I can’t even think of where to start with my protests, but he doesn’t give me a chance.
“Shhh.”
He holds up a finger in front of his lips. The same one that had just been in my pussy. Then he turns to his computer, as if ready to start his day’s work.
“The door is that way.”
And just like that, my brief rise and fall as the hand-picked mentee of Asher Marks, the firm’s billionaire founding father, is complete.
I really should have worn that outfit he gave me.