Take Me, Boss: A Bad Boy Office Romance

by Juliana Conners

  “There is no more mentor/ mentee relationship re-assignment, temporary or otherwise,” I’d told Mandy. “I have no interest in working with someone so cruel about other people. For the last time, please leave my office.”

  “You’ll be sorry,” she’d sputtered, picking up her designer purse and leaving my office in a huff.

  She’d stopped short of the doorway, as if struck by a good idea.

  “What if I tell everyone you sexually harassed me?” she asked.

  “I’d tell them it was quite the opposite,” I spat back.

  She turned away again, shaking her head, and left my office. I’m reminded of why I always think carefully before choosing— and thus having to reject— any potential pet. They have the tendency to become irrational and unpredictable. Usually I make certain all the rules are in place before making any moves.

  But I’d let Madilyn throw me off my game, without doing enough to make sure the game had even gotten started in the first place.

  It dawned on me that I may have lost the chance to work with the one associate who was enough of a challenge for me. And, even though it goes against my rules— not to mention my better instincts— I decided to do something out of the ordinary.

  I sent the lingerie she’d left here back to her.

  After all, what are rules if they’re not meant to be broken?

  And what’s the use of finding my perfect pet if it doesn’t involve putting up a little bit of a fight for her?

  But now it’s just a matter of seeing whether Madilyn wants to accept my invitation to join the game again. As I watch her working intently, I start to doubt that she’ll be a willing player.

  I hate that she has any fucking power or control over me. I need to remind her who’s boss and take back the reins. But first I need to see how she responds to my latest summons.

  Chapter 28 – Madilyn

  It’s late and all the paralegals have gone home. But I’m still here in Cubicle Hell working on Janice’s deposition summaries. I haven’t decided what to do about Asher.

  Out of inertia— or perhaps stubbornness— I’ve continued carrying out my plan to work hard for Janice, even at her busywork, so that if I need an out I have one.

  And yet.

  During lunch, I’d gone home and taken my dog Lucia for a jog to clear my head. Or so I told myself. Maybe it was really just an excuse to shower. To shave my legs. And to put on the black lingerie.

  I’d looked at myself in the full- length mirror, wondering if I could actually go through with this. The lingerie is damn hot, and made me look like a billionaire myself. I’d decided hell yeah, I can do this.

  I’d put on my same black skirt suit over the lingerie and then I’d returned to the office. I knew better than to approach Asher again. He wants to be the one to approach me. To give me commands and make me follow them.

  I’ve learned this about him, and accepted it. And, much to my surprise, I even like it.

  So I’ve been sitting here for the rest of the day, half telling myself I still have an escape plan— and even working at it— but mostly waiting for some sort of sign, some signal, some command, from Asher.

  My blazer is slung across the back of my chair, since no one else is around, and my shoes are off. My back hurts from slouching over in the inexpensive computer chairs the paralegals use.

  Just as I’m about to give up on Asher ever contacting me and decide to head home, I see the flashing notification of a new intra-office instant message. I click on it.

  Asher Marks: Have you decided to be my pet?

  I hesitate. But then I tell myself not to wait too long, lest I blow my chance yet again. I feel desperate, almost humiliated. And I love it.

  Madilyn St. Clair: Yes, Boss.

  Asher Marks: Prove it.

  Madilyn St. Clair: Yes, Boss.

  I stand up, ready to go up to his office. But the notification light flashes again.

  Asher Marks: Stay there.

  Madilyn St. Clair: Yes, Boss.

  Asher Marks: I want to see what you decided to wear for me before I decide whether or not this arrangement will continue.

  Well that’s confusing, I think. How can I…?

  But then another message appears.

  Asher Marks: Unbutton your blouse and show me your bra. But only if it’s the one I gave you and told you to wear. And only if you’re willing to do as I say from now on.

  What the hell?

  I turn around, wondering if he’s come down to my floor. I don’t see anyone. I turn back to the computer.

  Asher Marks: Just do it. Unbutton your blouse. Don’t question me. Don’t make me regret anything ever again.

  Madilyn St. Clair: Yes, Boss.

  I add:

  Madilyn St. Clair: I’m sorry. It won’t happen again.

  And then I unbutton my blouse. Just the top three buttons.

  Asher Marks: Further.

  I unbutton it all the way, and then, remembering, I type:

  Madilyn St. Clair: Yes, Boss.

  Asher Marks: Take it off.

  I swallow, careful not to look too reluctant, because I’m assuming he can see me.

  But how?

  My heart pounds as I think about the possibility of someone coming in. Either a lawyer to pick up a file from their paralegal’s desk, another paralegal who forgot something and needed to come back for it, or even the night janitorial crew.

  How humiliating.

  I can feel myself wetter than I ever thought I could get.

  Apparently I’m not opposed to a little bit of humiliation.

  I take my shirt off.

  I’m standing in the empty room, in only a black bra.

  Asher Marks: Show me your nipples. I bought you a bra capable of that for a reason.

  Without even hesitating, I unsnap the portion of the bra that covers my right nipple, and then my left.

  Asher Marks: Play with them while I watch you. Tell me you’re my pet.

  Madilyn St. Clair: Yes, Boss. I’m your pet.

  Asher Marks: Say it out loud while you play with your nipples.

  I take my nipples in between my fingers and rub them. They’re so hard and erect, and it feels so good.

  “I’m your pet,” I tell him, out loud, wherever he is. “I’m your pet, Boss.”

  Asher Marks: Very good. I can see you’ve decided to follow my instructions. And I have one more for you.

  Madilyn St. Clair: Yes Boss?

  Asher Marks: Put your blazer on— and only your blazer— and come to my office immediately.

  Finally.

  I thought he had planned to leave me here, playing with my nipples all night without getting to see him. I don’t think I could bear that kind of torture if he decided to tease me again like last time.

  Madilyn St. Clair: Yes, Boss. Your pet is coming to you.

  I gather my blazer and throw it over me, gripping it tight against my near- naked chest.

  Hurrying to the elevator, I keep my blazer clutched around me, looking around to make sure no one is here. I’d be mortified if anyone saw me like this, but I guess that’s part of the excitement. And part of Asher’s game.

  I’m a willing pawn now, playing along without knowing— or even caring— what the end game is.

  Chapter 29 – Asher

  Here she is, in my office.

  Madilyn St. Clair: the associate I’d researched, hired, and planned to make my newest pet. But whom I wasn’t sure I would ever fucking see in my office again. And certainly not like this.

  She looks vulnerable and submissive with a blazer barely covering her breasts and their exposed nipples that she’d just played with for me while I watched.

  She locks the door and then gives me a shy smile.

  “Sit down,” I tell her, my voice stern and commanding.

  “Yes, Boss,” she says, and she does.

  “Now show me what you were supposed to wear for me, but refused.”

  She spreads her legs for me agai
n, this time revealing the blank lingerie I had carefully chosen for her.

  I love when she does what I want.

  I’m glad she’s finally listening to me now and being submissive.

  “And take off your blazer.”

  “Yes, Boss.”

  She lets it fall to the floor. Her nipples are in plain view. I admire their erect pointiness, and her luscious curves as a whole before continuing, afraid of letting her see how impressed I am.

  “Come over here,” I finally say.

  “Yes, Boss.”

  She walks over to my side of the desk and I say, “Closer.”

  Her perfect tits are right in front of my face. I want to touch them but I don’t. Because this time when I touch her I want it to sting. To be memorable. So that she never forgets who’s in charge.

  I unsnap the covering on the crotch part of the panties and expose her pussy to my impatient eyes.

  It’s clean shaven. She had definitely decided to be my pet.

  I had wanted to taste her pussy. But now I feel that my position is too weak. She had obviously figured that I would take her back. Give her another chance.

  I can’t let her know that she was right. I return to my rules once again. I need to teach her a lesson. And make her pleasure me without returning the favor in full.

  “Turn around and bend over,” I command her.

  She leans over on my desk and I lift up her skirt.

  I take a moment to admire her heart shaped ass, fully exposed for my viewing pleasure. But I don’t say anything, or allow myself to linger too long on what I know is pure perfection.

  I take the thong part of her panties in my hand and move it over to the side. Her pussy is right in front of my face and she’s dripping wet.

  “I can see how much you like this.”

  Her beautiful pussy is throbbing, just waiting for me to enter it. But I don’t plan to give her that satisfaction just yet.

  “You didn’t do what I wanted last time,” I remind her.

  “I’m sorry, Boss.”

  I stretch her panties tight around her while I slap a firm hand on her right butt cheek.

  “Ouch!” she cries, involuntarily.

  I slap the other side, and she tenses up, but doesn’t say anything. She just sucks in a deep breath. I squeeze her ass cheek, which feels firm but malleable in my hand.

  I rub my finger up and down her clit, and she shivers. I know she wants me to do more. I almost feel myself giving in to her desire and my urge to feel myself deep inside her.

  But I remember my rules. I may have forgotten or bent most of them for her before and I’m even breaking too many now. I shouldn’t be going this far yet. I shouldn’t be giving her so much control.

  I want her so bad. I want her in a way I’ve never wanted anyone. I can’t even think.

  I need to take charge quickly. But I still need a release that I would usually be disciplined enough to wait longer for.

  I squeeze her clit and say, “Get on your knees and show me how much you want to be my pet.”

  I unzip my pants and she kneels down in front of me, eagerly grabbing my cock and beginning to pump its shaft while she licks its head. Her sparkling blue eyes look up at me with a mixture of innocence and naughtiness.

  I grab a hold of her nipples and twist them in my fingers. As she sucks on the top of my cock and then takes me all the way deep inside her mouth, I lean my head back so that she can’t see the look on my face.

  I know it’s a look of vulnerability, of letting go and giving in to whatever it is that she is doing to me— and however she is doing it so well. I had no idea a virgin could give such a good blowjob.

  I give in to my basest of desires while realizing she’s fulfilling something deep inside me that I didn’t know I needed. I feel my cock start to swell in her mouth, as she pushes it all the way inside her throat.

  “Madilyn, Madilyn, Madilyn,” I moan, as my cock pulses and throbs.

  Too late, I remember my rule about not saying their names. I can’t give them too much power.

  But she’s not like the ones who came before her. Something about her has overtaken me the way I thought I would overtake her.

  “My pet, my pet…” I groan, as my cum shoots into her mouth.

  I’m breaking all my rules for her and she doesn’t even know it. She laps up my cum and swallows it, but some of it still drips down her chin and neck.

  “That’s a good little pet,” I tell her, taking my cock out of her mouth and rubbing it all over her face, the way I’d meant to do before I’d cum inside her mouth.

  But it had felt so good. It was the release I’d needed.

  And it’s opened up something in me that I didn’t even know was there.

  Chapter 30 – Madilyn

  THE NEXT DAY

  Every boss knows he’s not supposed to fuck his employee. But Asher Marks is known for doing things he’s not supposed to do. And it looks like I’m one of those forbidden things he wants to do. The thing that surprises me is how bad I want to do it too.

  Today I had worn my red panties that he likes along with a black and white lace bra. When I was getting dressed this morning I just knew that today is the day I will lose my virginity. My older, experienced, powerful boss will take it and I’ll let him and I’ll probably regret it afterwards but I sure will enjoy it in the moment.

  But first, there’s something I need to do. And that is talk to him.

  He had messaged me to come to his office at six p.m. to talk about the Schwartz Capital case. But I go up at 5:45. The hallway is empty. The senior partners rarely have to work late. And their assistants are the most experienced and useful so they get the benefit of getting to go home earlier than a lot of the other assistants on other floors.

  I sit on Asher’s desk, much like Mandy was on that dreadful day I’d overheard her. But this time I’m in charge.

  He walks in at five to six, obviously having been at the firm gym. He’s wearing a wife-beater and running shorts and he’s a sweaty mess. There’s a shower at the firm gym but he obviously hadn’t been planning to fuck me tonight because he didn’t use it.

  The look of shock that crosses his face confirms my suspicion.

  “Madilyn,” he says, quickly shutting the door behind him and locking it. “You’re early. And you’re on my desk.”

  “Yes, Boss,” I tell him, trying not to smile at his shocked face.

  I know he’s surprised but I need to accept that I’m no pushover. I enjoy being submissive and I even like the power imbalance in our relationship, if it’s even a relationship. But if I’m going to lose my virginity to him, I need him to hear me out.

  “I wasn’t planning to…” he says, looking around as if other people might be in the room. He clearly doesn’t like when he’s not the one in charge.

  “I was planning to go over some things in the Swartz case,” he finally says.

  “I know,” I tell him. “And we can do that if you want. We can do anything you want, Boss.”

  A look of pleasure crosses his face and I know that he likes the way I call him boss and tell him he can do what he wants.

  “I just wanted to tell you that I’m not like the girls you’ve had in the past. If you want to be with me, you’re going to have to accept that.”

  “I know,” he says, quickly, as if he’s already thought about it.

  He purses his lip and a crease appears across his forehead. I can tell that he doesn’t exactly like the way things are going so I decide to make it a little easier on him.

  I open my legs a bit so that he can see my red panties.

  “I appreciate the way you stood up to me to Mandy,” I tell him. “I’m glad you didn’t see me as some secret, dirty fling.”

  “Mandy is a horrible human being,” he tells me, stepping closer and running his hands along my knees and then my inner thighs.

  It starts to drive me crazy but I try to stay focused.

  “I’m sorry I tried to repla
ce you with her temporarily,” he says. “But it didn’t work out. She wasn’t you.”

  He kisses me and I feel a wave of heat wash through my entire body. Then he pulls away and looks me up and down, his hands traveling all over me just as much as his eyes are. I love the smell of his natural sweat and the way it looks when it glistens on his hardened muscles.

  I can see a tattoo peeking through his shirt opening and I love the fact that he has ink on his chest. I never thought I would like a guy with a tattoo but it suits him perfectly.

  “You’re beautiful,” he says. “I love every inch of you. Everything that Mandy said was just out of jealousy.”

  He pushes me back on his desk and then he spreads my legs open wide. He gets down on his hands and knees and pulls my panties to the side.

  “You have made me come completely fucking undone,” he says. “Do you have any idea what you do to me? I think I may have met my match.”

  I raise my head a bit to smile at him as he begins to lick my pussy. His tender kisses on my clit turn into heavy pressure from his tongue and he licks my clit up and down and then begins to suck on it.

  “Oh my God,” I whimper, the best fantasies from my wildest imagination coming true. I lie back and let him alternate between teasing my clit with his lips and then pushing his tongue into my wet opening.

  “I feel so good.”

  I grab onto his thick hair as he takes my clit in his mouth and chews and sucks on it to the point where I can barely stand it.

  “I’m coming,” I tell him, lifting up my hips so that my pussy meets his mouth even more as his tongue strokes my hole and his lips suck on my clit. “It feels amazing. I can’t breathe…”