So that’s it then. No more distractions. Maybe I need a good break from relationships of any kind in order to focus on work.
I’ll take this break with Jimmy, which somehow I’ll successfully turn into a permanent break up. As time goes on, it will get easier for him, and he’ll understand. Maybe he’ll even meet someone new.
And I’ll let Asher know that I need to keep things professional at least for now. I feel an obvious aching— physically and emotionally— that I can’t help but dwell on.
Deep inside, I want to wear that outfit for Asher. I want to know what he’ll do to me in it.
I slip my finger underneath my skirt and feel myself soaked with dampness. I can’t help but touch myself, imagining that it’s Asher instead of me. I’m sure he’d know how to touch me, kiss me, fuck me the right way. The way I’ve been wanting Jimmy to for all this time.
But I need to stay focused on my goals. I get up and wash my hands, and then settle back down to work, not giving myself the satisfaction of an orgasm. Maybe after I finish these assignments. Maybe after I see Asher tomorrow, as I’m sure I’ll have a lot of pent- up sexual frustration.
I’ll just tell him I’m not sure yet. That maybe we should wait until I’ve proven myself professionally before we explore anything… personal.
Because I just can’t risk opening myself up to anyone right now. Especially someone with that much power to make or break my career. I can only trust myself. Only rely on myself.
Asher will have to understand.
Won’t he?
Chapter 18 – Asher
At 6:50 a.m., there’s a knock on my office door.
Oh good, she’s early.
I’m glad that Madilyn St. Clair knows not to leave me waiting again.
“Come in,” I tell her, which is a superfluous instruction, since the door is already open. She’d knocked on the part that was wide open. “Lock the door behind you.”
“Yes, Boss.”
Now it’s my turn to lick my lips. Things are starting off exactly the way I’d planned. She’s wearing a black skirt suit just as I’d instructed.
“Sit down.”
She approaches the chair in front of my desk and lowers herself into it, looking a bit hesitant. She has the accordion file in her hands.
“Did you complete all the assignments I gave you?” I ask her.
“I reviewed all the case files and prepared memorandums for each one, Boss,” she says, removing some printed pages from the top of the folder. “They summarize the case history to date, based on my review of the docketing statement as you instructed. When the file included any pleadings or depositions, I also reviewed and summarized those. And I included any questions or thoughts I had throughout my review.”
She places the memorandums she’d prepared on my desk, and looks up at me eagerly, but still with a bit of hesitation in her eyes.
And now I think I understand why.
I’m hoping I’m wrong, but I don’t like the quick turn that our meeting is taking.
Sure, she’s done an impressive job. I don’t even have to look at her work to know that. I leave the memos on the desk, barely giving her the satisfaction of seeing me look at them. From her own account, which I believe because I know she’s bright and hard working or I never would have hired her to work at my firm, she’s summarized the docketing statements and she’s even gone above and beyond my instructions, by reviewing other case documents and including her analysis.
She did it all in a limited amount of time— she’d left my office at six o’clock last night, meaning she’d prepared all of this in about thirteen hours. Since she doesn’t look like she’s lacking in sleep, she must have worked fast and she must know what she’s doing when it comes to basic legal tasks.
Madilyn St. Clair will definitely make a good associate, and a good mentee.
But I want her for something more.
And I’m beginning to realize that she doesn’t want to give it to me.
“You only partially answered my question,” I inform her.
She looks at me, as if she’s afraid to say anything.
I’d asked her whether she’d completed all the assignments I gave her and she’d only mentioned the five cases. Not the sixth assignment.
“I’m interested in your work, and in discussing these cases,” I tell her, nodding at the memorandums on my desk, and not even trying to hide the fact that I’m losing my fucking patience with her. “But there’s a specific way I like to work.”
She swallows.
“There was a sixth assignment,” I remind her.
She nods and looks down at the file in her lap.
“I hope you have dressed as I instructed, as that’s the only way this meeting can continue.”
“Mr. Marks, I—” she begins, but I cut her off.
“Boss.”
“Boss. I. I need to talk to you. I need to explain—”
I feel blood rushing to my face, and I do my best to contain my anger.
I can’t believe I chose wrong. She’s resisted my instruction. How could my judgment have been so off?
“There’s nothing to explain,” I tell her. “There’s only a very specific way I can work with you, and no other way will suffice. So all that remains is the question of whether or not you’ve complied with all my instructions.”
Damn her, for making me have to explain myself further. That’s all I’m going to say. I’ve already given away too much already, to someone who clearly doesn’t deserve it. She can’t even follow one simple direction of mine, yet she dares to have the audacity to want to work with me.
“Boss. If you could just listen to what I need to explain—”
“I’m not interested in listening to you. Or to your feeble explanations,” I tell her, trying hard to keep from raising my voice too high, from giving myself away.
My cock is swelling in my pants, dying to escape and find release. It’s becoming clear that’s not going to happen. And the damn thing has a mind of its own. It appears to be excited that she’s resisting. It clearly wants me to do whatever it takes to persuade her.
But I won’t do that. I know to listen to my brain over my fucking cock. I stupidly decide to hope against hope that there’s still a chance.
“What I’m interested in is seeing what you’re wearing under that suit,” I tell her. “Ms. St. Clair, please spread your legs for me, and show me what’s under your skirt.”
She moves her knees apart from each other, almost like a reflex. My cock rises even higher, ready to start being satisfied.
I love her curvy hips and plush ass. Her full breasts and small waist. And now I’m going to get to see her wearing the black little number I ordered especially for her. I can’t wait.
But then she stops. And she takes out the manila envelope from the accordion folder and puts it on the desk, on top of the memorandums.
“Boss, I did all the assignments except for that one,” she says, truly seeming remorseful. “I’m sorry.”
Her head hangs in shame, and her voice sounds repentant. “I’m just not ready, right now, at this time, to—”
She’s trying to make me wait again. She must get off on it. It must be some sick pleasure of hers, and now she’s torturing me with how she tricked me. How she did the assignments, came in here at the assigned time— even wore the damn suit skirt as I’d requested— but didn’t wear the outfit I’d given her and instructed her to wear.
“If you’re incapable of following simple instructions,” I tell her, “then there’s nothing worth talking about. I don’t know why you would do the rest of the assignments and not this one. This was the most important one.”
“Oh. I—”
She falls silent, and I realize she actually thought that we could proceed if she was unwilling to accept all the terms of working with me.
I knew that Madilyn St. Clair was different from the normal women I employ as associates. I even had a feeling that she was different from th
ose whom I had chosen to mentor in the past. But she can’t actually be so innocent and naïve as to think she could pick and choose which parts of this working relationship she wanted and which she didn’t. She has to be arrogant, cruel, teasing, taunting me.
I have to end this right here. I have to end this for good. I can’t let her know she holds any power or sway over me.
And yet.
There’s the way she appears remorseful, almost supplicant. The way she really does seem confused, innocent. And the way she had started to open up her legs for me.
I know she wants to let me in. I just have to break her down a little bit more.
I ask myself if I should give her a fucking second chance.
No. I never have and can’t start now. I must remember the rules I’ve set for myself, and for the relationships I establish. It’s worked until now and I’m not going to let Madilyn St. Clair change that.
But I can see how far I can push her, before casting her aside and choosing someone else. It’s the least I deserve, for spending so much time and energy researching her, choosing her, giving her so many damned instructions that she incorrectly thinks are up for her picking and choosing as to which ones to follow.
I feel the blood cursing through my hungry cock, and I decide to throw it some crumbs. It’ll have to wait for a more pliant associate to be fully satisfied. But I bet I can get a little something out of Madilyn St. Clair right now before parting ways with her for good.
Chapter 19 – Madilyn
“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 it 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 alrea
dy 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.
Chapter 20 – Asher
Once Madilyn leaves, I run my fingers under my nose. They’re still wet with her juices, and I can smell the sweet, expectant scent.
I can’t help but taste her juices on my finger. Delicious. Just like she would be if she had played along better. I would be eating her up right now and she would love it.
The game we had played was an easy win for me, and that’s why I had suggested it. I was almost sure she would be wearing red panties.
Madilyn St. Clair is someone who cares about image and prestige, but she has a fucking naughty, adventurous streak she rarely wants to admit or indulge. She plays by the rules, although she secretly wants to rebel. So she wears conservative business suits with cute red panties underneath. I knew that about her before I really knew it.
If only I had followed all my rules, and had only played games I was sure I could win. Instead, I’d had to play games that took me in over my head. I only wanted to see and touch what I knew I could have, if I were only willing to give her more chances. But now, I find myself wanting more.
Enough, I tell myself. Time to get to work.
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