Knock Me Up, Boss: A Bad Boy Office Romance

by Juliana Conners

  So I did what I had to do: I got far, far away.

  All the way to the South Pole, in fact.

  Nolan, a climbing friend of mine, had been bugging me for months to join him on a yacht based expedition of the Antarctic Peninsula that he’d been planning to take this week.

  Initially I’d told him to just borrow my yacht and go without me, because I would be too busy with work. But that was only half true.

  Sure, I have a big trial coming up in the Schwartz Capital case, for which I really should be preparing. I hope that Madilyn is as good of an associate as she is a pet, because I’m entrusting her with the case in my absence. She just doesn’t know the specifics or length of my absence, or the level at which I’m entrusting her.

  The main reason I’d told Nolan I couldn’t go on this trip was that I was expecting to be grooming my next pet. Madilyn. But everything with her happened much more quickly than I’d anticipated; much more quickly than it usually does. And I didn’t know what to do to slow it down, except to tell Nolan to count me in on his trip.

  Now, though, I’m wondering if it was really such a good idea. I’m off my game in every aspect of my life.

  Sure, the trip has been great, and the scenery has been breathtaking so far. Nolan and some of his finance buddies and I had boarded in Ushuaia and departed for Drake Passage, sailing Port Williams, Chile. We’d enjoyed a short climb in Port Lockroy and then a longer climb on Mt. Lopez, on Doumer Island.

  We’d headed down the Graham Coast, as far as Prospect Point, and we’d just spent two days skiing and climbing, but it didn’t clear my head like it normally does. And I had a scary slip off of a secure hold, which isn’t like me at all.

  “Dude, are you all right?” Nolan had asked, as he helped me up.

  “Yeah, I’m just not feeling too great,” I’d told him.

  He looked at me funny.

  “The last time you slipped during a climb—”

  “It’s nothing like that,” I’d quickly protested, knowing he was thinking of my divorce.

  My ex-wife and I had tried for a long time to make it work, but when we finally called it quits, the break up really fucked with my head.

  It’s nothing like that at all, I’d repeated mentally, as if trying to convince myself it was true as much as I was trying to convince Nolan.

  “Have you even talked to her lately?” he asked, raising a concerned eyebrow.

  “No. No, I haven’t.”

  Which was true, although I’d left some details out, that he didn’t need to know about. My ex-wife did call me last week but that’s nothing out of the ordinary.

  She likes to call every time the new associates start working because she knows I might be choosing a new pet. She has a ridiculous theory that I’m only using them as substitutes for her, and none of them are good enough so I have to keep “churning and burning through them,” as she puts it. She thinks I purposefully pick pets that aren’t right for me so that I don’t get attached to them.

  Even years after our divorce, she still likes to be cruel to me. I know that she’s not correct in her theory.

  I know that my pets are my diversion, and that the reason I rotate them rather quickly is so that I don’t get close enough to them to allow any of them to hurt me the way she did. It’s easier and more fun that way and she’s just jealous and angry that I’m no longer available to be her emotional punching bag.

  I ignored her call, not wanting to get into it with her. Usually I show myself I’m the bigger person by picking up the phone and telling her to fuck off, but right now I don’t want to deal with her. I have enough on my plate.

  I’m sure she’ll continue to call. But I’m too far away to be reached so she can just listen to the phone ring and ring and ring. For the first time since our divorce, I really think I’m fucking over her.

  If only it wasn’t because of Madilyn. Madilyn who apparently isn’t over her own ex.

  “All right, man,” Nolan had finally relented. “But maybe you need some rest.”

  “Yeah, I agree,” I’d said, and come back here to the yacht.

  Lounging comfortably on the couch, I take out my iPad and access my secret file of former pets. None of them had hesitated to dress up— or undress— and pose for me. All of them do exactly what I want, when I want them to. All of them, except for Madilyn.

  Damn her. I scroll through the leather- and lingerie- clad pets of my past but I don’t feel any of the emotions that looking at them usually evokes. There’s no power. There’s no sense of control. There’s just the desire to see Madilyn rather than any of them.

  What the hell am I doing out here in Antarctica, running away from my fucking problems? I need to face them.

  But I know that if I go back to the office, I’ll have sex with Madilyn again. And if I have sex with her after knowing how she betrayed me, it’ll be too late to back out. I’ll be a sucker. And I hate being a sucker.

  But maybe it’s already too late. Maybe I’m already a sucker.

  Because I do something I’ve never done before in my life: I delete the photos of my past pets.

  That seems to seal something I already knew deep inside me.

  Madilyn is the one for me. As scary as it is, I have to face it.

  I power off my iPad and walk out to the deck of the yacht. I squint into the snowy mountains, where Nolan and his friends have nothing on their minds except climbing to the top of the white peaks.

  It was a mistake to come on this trip. All I can think of is showing Madilyn the views, teaching her how to climb or ski, if she doesn’t already know how. I’ve never felt this way about another pet. I’ve always been able to separate work, climbing and play.

  I know I have to head back and deal with whatever looms in front of me. Just like when I’m climbing.

  Our plan for this trip was to eventually work our way back north to Paradise Harbour and be in position to sail back to South America for a ski tour around Danco and Ronge Islands. We’re supposed to sail back to Port Williams and go for an overnight hike in the mountains behind the town before departing for home from Ushuaia.

  But I can’t stay for all of that. I need to get back to Madilyn.

  I phone my private helicopter to come pick me up once I dock. And I leave a message for Nolan. I know he’ll understand, even though he’ll know that I’ve let a woman fuck with my head.

  He’ll just think it’s a different woman— the same one that has been doing it for decades, but for some strange reason my ex-wife no longer seems to have any power over me. Apparently the space that was taken up for years in my mind and heart has been replaced by my new associate, mentee and pet, Madilyn St. Clair.

  I just have to give her an ultimatum. Choose Jimmy or me. I’m not sure I can forgive her for lying to me. But maybe if I punish her for doing it, I’ll have some motivation to try.

  Chapter 34 – Madilyn

  I’ve come to work early because I have nothing better to do these days. Nervous excitement often wakes me up even earlier than usual, and by the time I’ve finished walking Lucia, there’s nothing else to do but get dressed— with Asher in mind, as always— and head into work.

  The good news is that my billable hours are really high this month. And I’ve covered just about everything possible in the Schwartz Capital case.

  The bad news is that I’ve worked myself out of work. I’m beginning to fear that if Asher doesn’t return soon, I’ll have to go begging Janice for more boring deposition transcripts to summarize.

  In Asher’s absence and ever since getting the call from his “wife,” I’ve done some thinking. I’m not sure she even is his wife. I haven’t heard a thing about her and I sure had heard a lot of other things about him before I met him. I Googled him and didn’t see anything about a wife.

  Maybe she’s just someone who is jealous and starting problems. She could even be Mandy, for all I know. And even if he has a wife, maybe they’ve been separated for a long time. Maybe they’ve had an open r
elationship or other agreements. I certainly know about on again off again relationships. Who am I to judge?

  Perhaps these are all my desperate attempts to reconcile my desire for him with my disgust at him for lying to me. But I also know that life is never perfect. While Asher has been gone I realized I still needed to change quite a bit about my life.

  When I got home after seeing Asher the last time we were together— the first time I’ve ever made love— I saw an annoying post on my Facebook wall from Jimmy. He was trying to act like everything was great between us and sucker me back into being with him again.

  Suddenly my old feelings of guilt and obligation just evaporated. I realized he’d been playing me for his own reasons and I shouldn’t feel bad about wanting it to be over for good. I’d never made that decision before I met Asher, but I know now that it’s for the best.

  I’d called Jimmy up and said, “This has got to stop.”

  “What does?” he’d asked innocently.

  “Delete that picture from Facebook,” I told him. “You said it was for your mom.”

  “It was, but you looked so beautiful in it that I also thought I’d…”

  “Jimmy, it doesn’t matter. I’m blocking you from Facebook.”

  “What? You said you wanted to be friends. You said that maybe in the future…”

  “No,” I’d told him. “There is no future for us. Sometimes people come into your life for a certain reason and then it no longer works out. I appreciate you being there for me when my dad died. But it shouldn’t have turned into such a long and unsatisfying relationship. We should have let it go a long time ago.”

  “It wasn’t unsatisfying for me,” he’d said, pouting.

  “Jimmy, we never even had sex.”

  And there it was: the truth of the matter plain as day, more apparent than it was during all of those counseling sessions that never went anywhere.

  “We’re just not right for each other and that’s okay,” I’d told him. “Good bye.”

  “Good bye,” he’d said, and I knew this time it was for good.

  I’ve had such a feeling of lightness and relief since then. I don’t know what will happen with Asher and me but I know that the experience of being with him has changed me for the better. Life is too short to be stuck in a bad relationship. I want the excitement and adrenaline of what I have with Asher, or nothing at all.

  But now, it’s time to work. There’s a big trial coming up and I have no idea where Asher even is.

  I have to start a pot of coffee, since no one else is around to make it. I sit down with my cup after waiting for it to brew, and I see a flashing instant message notification.

  I freeze, both of my hands gripping my coffee mug. I finally remember how to remove one of them, and place it on the mouse to click on the message.

  Asher Marks: Miss me?

  Madilyn St. Clair: Yes, Boss.

  Asher Marks: How much?

  I pause. Enough that I’ve been masturbating every night— and sometimes in the bathroom at work— wondering if you’ll ever fuck me again. Enough that my thoughts have been all consumed by you. Enough to nearly memorize every line in every transcript of every hearing in the Schwartz Capital case.

  But I can’t tell him all of that. So I look around, making sure no one else has come in, and then I unbutton my blouse. I reveal a flash of the black bra he bought me— which I’ve been wearing every day since I last saw him, being careful to hand wash it and line dry it at home.

  Asher Marks: That’s it?

  I unsnap the covering of my bra, exposing a nipple.

  Asher Marks: That’s better. Now open the top drawer of your desk.

  Startled, I pull open the drawer. I don’t see anything except my usual assortment of office supplies and hair ties. Then I hear a notification of a new text message.

  Asher Marks: Under your desk organizer.

  I pull up the plastic desk organizer and there it is.

  A pink feather.

  I know that nothing should surprise me about Asher anymore, but I have no idea when he put this here, or how. I suppose he just arrived at the office even earlier than I did.

  Asher Marks: You know what to do with it.

  I look around again, starting to get fearful that some other early bird will walk in. An eager beaver paralegal. I’m already the talk of the office, but that would just completely solidify my reputation.

  Asher Marks: Hurry up, Pet.

  Madilyn St. Clair: Yes, Boss.

  I lightly place the feather up against my nipple. It instantly stands at attention. I rub the feather up and down, loving the soft and fluffy sensation against my skin.

  Asher Marks: And the other one.

  I unsnap the other bra covering and move the feather back and forth between both of my nipples.

  I’d forgotten to type my complicity, but then I remember that he can hear me, so I say, “Yes, Boss,” out loud.

  Asher Marks: Are you ready for your training session?

  “Yes, Boss.”

  Asher Marks: Put the feather in your mouth and come to me just as you are. Don’t cover yourself. You’re all mine. And I don’t care who knows it.

  What about you? I want to ask. Are you all mine too?

  But I don’t.

  It’s his turn to be in charge and I’m just glad he’s back. I’ve never felt so compliant or submissive before. But I’ve never enjoyed any other feeling this much, either.

  I take a deep breath but I say “Yes, Boss” and stand up obediently, before he gets angry. I don’t want to do anything to ruin this upcoming encounter that I had been fearing wouldn’t happen. And that I hope will still happen.

  I walk quickly to the elevator, with the pink feather in my mouth and my nipples exposed to whoever might pass by. Luckily, it’s still early, and no one’s around.

  But there’s no way that Asher could know that. He’s taking a big risk and he obviously wants me in on it. I suppose he can pull strings if I’m caught but my heart still pounds as I head up to his floor.

  The air conditioner blasts my nipples, causing them to stand up even straighter still. It blows my feather every which way.

  I’m afraid of an early appearance by a secretary— I know that some of them come in after their kids leave for school, and leave early in the afternoons to pick them up— but no one’s here. Perhaps Asher has a way to tell them not to come in yet. Or perhaps he just doesn’t care.

  I think about the phone call from his “wife” and turn cynical. I’m sure that knowing that someone can catch us is all part of his sick and twisted game, just like I am.

  And yet, I’m so excited as I approach his office that I almost float right in. The door is open, and when he sees me he nods. It’s a quick gesture— his eyes move down to the floor and back up again— but I know what he wants me to do.

  I shut and lock his door and then I get on my hands and knees. With the feather still in my mouth, I crawl across the floor to his desk.

  “Very good, Pet,” he says, tilting my face up to his.

  It’s obvious that he’s impressed.

  He takes the feather from my mouth and rubs it on my breasts, much like I was just doing downstairs, except that now it feels even better. I shiver, and he says, “What have you learned about the Schwartz Capital case in my absence?”

  “The company was incorporated in 1992,” I begin, as he smiles and takes one of my nipples in between his fingers. He rubs my nipple while also brushing it lightly with the feather.

  Now he’s as obviously impressed by my case knowledge as he was by my submission, so I continue my litany of facts. At one point I say, “The co-founder’s son and cousin had a difference of opinion as to how…” and he pinches my nipple, hard, causing me to stop mid-sentence.

  “Owww!” I exclaim.

  “The co-founder’s son and nephew had a difference of opinion,” he corrects me.

  “Yes. Sorry, Boss.”

  I continue reciting the facts I�
�d memorized, as he strokes my nipples approvingly.

  “Stand up,” he says, although I’m not done reciting.

  “Yes, Boss.”

  He unbuttons the rest of my blouse and then removes it. He looks at my breasts as if he’s going to return to fondling them, but instead he unzips my skirt and lets it fall to the floor. I’m only wearing his lingerie and my heels.

  Then he unsnaps the covering on my panties.

  “You’ve been wearing this the whole time I’ve been gone?” he asks me.

  “Yes, Boss.”

  “What a good little pet,” he says, running a finger along my pussy. “You’ll be rewarded for your loyalty.”

  I stare back at him, trying hard to catch my breath.

  I want him to pick me up and lay me down on his desk, but I know better than to make any requests.

  He says, “Turn around.”

  “Yes, Boss.”

  “And continue.”

  “Yes, Boss.”

  It’s getting harder to remember everything I’d learned about the case. All I want is for him to lay me down on his desk and fuck me. But I do my best to continue with the background facts.

  He pulls my thong over to the side, so that I’m completely exposed to him.

  My back is mostly turned to him, but I can see a bit with my peripheral vision and I’m pretty sure he’s removing his tie. Just when I think he’s going to undress and finally take me, he surprises me once again by tying one of my ankles to the leg of his desk.

  “Keep telling me what you’ve learned,” he commands.

  “Yes, Boss.”

  I begin to talk about the proceedings in the case, starting with the Complaint being filed. It’s not exactly pillow talk, but it seems to be doing the trick. I can hear his breath quicken behind me.

  He walks over to a door that appears to be a closet, where he must keep extra ties and blazers for court. He comes back with two more ties and ties my other ankle to the leg of his desk chair.