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 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.
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.
But I can’t concentrate. I do some mindless deposition preparation and then I scan the Internet for the latest news— just as a distraction.
Finally, eleven a.m. arrives. Over lunch, I usually run with a small group of other guys at the firm. A few partners, an associate named Matt to whom I give quite a few projects, and Mike, the firm’s IT guy.
But today, I go to the firm’s gym earlier than usual, before the time that we usually meet up to run. I change into my running clothes and then decide to take a loop around Tingley Beach instead of our group’s normal route to the Country Club and back.
I just want to be by myself. I need to clear my head, which has been torturing me almost as much as my cock, ever since Madilyn left my office this morning.
All my cock wanted to do was see and then enter her beautiful exposed pussy. I almost think she would have let me. Clearly apologetic— and clearly turned on— she’d let me play with her, slap her, tease her. And she’d clearly wanted more.
But I didn’t. I can’t.
I just wanted to show her who was in control. All that she could have had by playing by my rules.
My rules are in place for a very specific reason. I had to put them in place after everything I went through with my ex-wife.
My buddies tried to warn me about her, but I wouldn’t listen. I guess I had to find out the hard way how women can be so cruel and heartless.
“She’s just like your mother,” Ron would say to me, when I’d complain about whatever the latest thing was that my wife had said or done to me.
“I don’t want to talk about my mother,” I’d tell him.
But really, I didn’t want to talk about my wife.
I thought I’d come to terms with the kind of person my mother was and why. I’m a rational, analytical man, and if I can logically understand something, then I can deal with it.
My mother was the way she was because my father left her when I was a baby. She had a series of short- lasting relationships with other men, but I think she was always waiting for him to come back.
And in the meantime, she took her misery out on me. My father never came back. He never cared about her. Or me. It made sense to me that she saw me in him and wanted to get back at him by being cruel to me.
But my ex-wife had never made any sense to me, as much as I tried to figure her out. She seemed to enjoy being cold and calculating for no reason. Until it all ended and we finally got divorced.
So I started playing the field. And because it was a game I set up rules. To protect myself from any more cruel women wishing to play with my heart and jerk me around.
I no longer have a weak spot for women who treat me like crap. I make sure of it.
As I come around a bend near the duck pond, a little train is passing by, full of kids and their mothers. It’s a trolley- type train, made to look like a real one, that takes them around the zoo, botanical gardens, and Biopark.
A boy who looks to be about four years old waves at me and as he does, a small toy train— a miniature version of the one he is riding on— slips out of his hand. The look on his face changes from pure joy to sad frustration. He cries, pointing to the toy train on the ground but his mother looks ahead, oblivious to the fact that he had just dropped it out the window.
I pick up the toy train and run along after the real trolley. When I catch up to the boy he sticks his head out of the trolley window and stops crying. A glimmer of hope passes over his face— that perhaps his toy isn’t lost for good— and he smiles at me again, but more hesitantly than when he was gleefully waving at me.
I hand him his toy train and he grasps onto it. His big, excited grin re-appears.
He claps and says “Thank you!” in garbled child talk. His mom finally looks out at me and, realizing what had happened, smiles and thanks me as well.
I wave stupidly and turn back in the direction in which I had been running as the train and its young rider— now firmly grasping his toy— head out of sight.
I’m left with a feeling of emptiness. When I’m honest with myself, I know that although I have a successful career and more money than I ever thought was possible for one man to have, I realized a long time ago that I’m incapable of maintaining a solid relationship.
So I construct ones at work that are the best replacement I can think of. I make sure they suit my needs— and even the needs of the other party— without taking over too much of my life or leaving me open to mistreatment.
I usually take a long time to choose the associate who will play that role for however long it lasts, until we both move on to something new. I am rarely wrong. But this time, I was.
And now it is fucking with my head and making me re-think everything about my life and this “game” I thought I liked to play.
Sometimes, my newest choice resists a bit at first and I don’t mind that so much. I even like it since I like a challenge.
I thought I had struck gold with Madilyn, after she didn’t jump at my first command but she still seemed eager and ready to please. I thought she was the perfect mix of reluctant yet eager.
But I guess it was too good to be true. Even though I spent a lot of time and energy on Madilyn, I know I have to let her go. Cut my losses and move on. Just like I do in any other business or legal deal that turns sour.
I can’t give anyone the power to disobey my simple instructions. I know it’s a slippery slope and that next they’ll be playing with my head and my heart.
I don’t give anyone that opportunity. Especially not someone as unpredictable as Madilyn St. Clair, no matter how irresistible she might be.
Chapter 21 – Madilyn
ONE WEEK LATER
I knock on the door of Janice Maloney, a partner at the firm. I’m not here of my own volition. Rather, earlier this morning, my computer lit up with a notification that I had an instant message from Asher.
I jumped with nervous excitement, not only because I was glad to hear from Asher, but also because I was glad to hear from anyone about anything. All last week I had sat at my desk in my cubicle with nothing to work on.
I was beginning to fear that even though Asher said I wouldn’t be fired for refusing to be his “pet” or whatever it was exactly that he wanted me to be, that in reality I would have no chance at the firm because I had refused.
I’ve been miserable all week and Jimmy has been bugging me about getting together to talk. I’ve put him
off, but this morning I finally responded to his email, agreeing to meet with him.
It’s not that I want to get back together. Experiencing whatever it was that I briefly experienced with Asher has shown me that I need to be done with Jimmy for good. I need to find something like what I could have with Asher, except with someone I can actually have it with without wrecking my career.
When it comes to Jimmy, I just want closure. And since nothing is happening in my professional life, I figure I should at least take some control over my personal life.
The Barbies often walk by my cubicle and giggle, as if I’m some pariah cluttering up this space. Or some rejected associate who couldn’t figure out when it was time to throw my resume on Monster.com and start looking for another job— which is probably closer to the truth.
This morning after I saw the notification flash on my screen, I’d anxiously clicked on the instant message. I didn’t even care how desperate I looked since no one ever seemed to be paying attention to me anyway.
Asher Marks: Please go see Janice Maloney. She will now be working with you in the mentorship role.
My heart sank. I suppose I’d hoped against hope for another chance with Asher. Sure, he’d told me he could no longer have me as his mentee, or “pet,” or whatever.
But then he’d played with my pussy and made it throb and drip for him. He couldn’t deny that there was something there between us. Could he?
I still feel I’m in some kind of shock that it all happened so quickly like that and that now it’s really over. I can’t help but admit to myself that I’ve been pining for Asher. His look, his smell, his touch.
Why couldn’t I have just worn the fucking outfit? It’s not like I didn’t put myself on display for him after all. And it’s not like I didn’t enjoy it. In fact, I’d enjoyed it much more than I thought I would even in my fantasies.
I guess I’m being reassigned to Janice. I’m pretty sure she’s Mandy’s mentor, and that Mandy isn’t too happy about it. I’d overheard her in the firm cafeteria telling the other Barbies that Janice was “flighty.” “A real space cadet” were her exact words.
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