Knock Me Up, Boss: A Bad Boy Office Romance

by Juliana Conners

  But what if I did wear it? How would I feel when he wants to see me in it?

  Naughtiness.

  He wants to do things to me that Jimmy never has. I can only imagine what he’d do to me when he sees me in this outfit…

  Suddenly, Jimmy bursts through the door, adding fear to the mixture of emotions I’m feeling.

  I jump. Then I shove the envelope into the accordion file and stuff the other folders in the file as well.

  I try to look nonchalant. I remember I’m upset with Jimmy. I remember he has no business barging in on my life. And that whatever is going on with Asher has nothing to do with him.

  But I also remember that we’re supposed to talk, and talking to Jimmy is the last thing I want to do right now. My head is still spinning from Asher’s latest and most interesting instructions. I know I have to deal with the issue that’s in front of me but all I really want to do is think about what Asher wants to do with me in that outfit.

  Chapter 16 – Madilyn

  Jimmy sits down in the chair next to me, seeming not to notice the files or what I was doing, thank goodness. He doesn’t say anything, likely expecting me to ask him where he’s been or what he’s thinking.

  The old Madilyn would have done that. But that was before we broke up. I don’t want to lead the conversation for once. He’s the one who was calling me incessantly at work. He’s the one who wanted to talk.

  “Madilyn, I know you didn’t want me to be here tonight, and I tried to stay away, but I just have to talk to you,” he finally says.

  “Okay. Go ahead,” I tell him.

  My mind is set; I don’t want his words to soften my resolve. But he has to hit me where it hurts.

  “Do you remember the day we met?” he asks.

  Of course I do. The day I met him was the worst day of my life and, back when things were kind of good between Jimmy and me, I also used to think it was the best day of my life too.

  My father had just died. On Valentine’s Day, of all days. Being single, I was in the grocery store buying sweets to comfort myself with when I got the phone call from my mother. He died from a completely unexpected heart attack. Just the kind of thing fate likes to deal out as a cold, cruel twist.

  My father was always very athletic and healthy. He ran marathons and would constantly tell me I should watch my weight, slim down a bit, eat less and exercise more.

  To be honest, it was annoying. I’d tried to tell him I accepted myself for who I was and that I felt he judged me based on appearances instead of health, since I’d never had anything wrong with me medically. But he always insisted I should try harder.

  I think he wanted a skinny, pretty daughter who liked to work out and care how about looking like some fashion model. I would never be that type of person. And it hurt, because in every other way, I wanted to be like my dad.

  My father had a successful career as a financial planner. I admired his ambition. He always encouraged my education and career goals— unlike my mom, who was a homemaker who thought women should stay home with their children, and who questioned why I was even going to college.

  My dad was always proud of my educational achievements and professional aspirations, but clearly they weren’t enough for him. He also wanted my physical appearance to be different. To be his definition of “perfect,” which isn’t as objective as getting straight A’s or being first chair in the symphony.

  I resisted all attempts of being something I’m not physically. But I guess that’s why I’ve always worked so hard at school. I had to prove to myself that I was worthy for other reasons aside from looks. I had to prove my dad wrong. And it’s hard for me to give up any control because I always need to be the smartest, brightest and best at anything that I do have control over— namely, my intellect and ambition.

  But regardless of our differences, I loved my dad. And that day in the grocery story, my mom wailed into the phone.

  “He had just run a 50 mile race,” my mom was saying into the phone. “I always told him he was running too much. That couldn’t have been good for his body, his heart. But he never listened to me. Your father was so stubborn and pig-headed…”

  “Mom!” I’d interrupted, leaning against a display full of reduced priced items and grasping a metal rack to steady myself.

  To this day, I remember how the shelf felt cold and sturdy in my hand, and how I was relieved to focus on that texture instead of my mom’s words. I know it’s stupid, but the rack just felt steady compared to the whirlwind news my mom had just delivered. I felt lonely, sad and afraid, and I never wanted to let it go.

  “Mom. I’m in a store. I can’t really deal with hearing about your resentments towards Dad right now. Can I call you back once I’ve had a chance to…”

  “Oh, you can’t deal with hearing me talk about it?” she’d exploded, yelling at me through the phone. Despite my best efforts to hold back my tears, they started flowing. “You’re not the one who has to live in this house after he up and died on me like that, without ever thanking me for all the things I’ve done for him. You’re not the one who devoted your life to him for thirty-five years!”

  If I hadn’t been so upset, I would have rolled my eyes. Leave it to Mom to be overly dramatic and make everything about her.

  Here she was claiming to have devoted her life to him. Even though she and my dad had had a tumultuous relationship for most of my adolescence and adulthood. Even though each of them was always complaining about the other to me and both of them had told me they would get divorced if their religion allowed it.

  I could see right through her. I knew that she stayed with him not only out of obligation but also out of fear. She had never worked anywhere, never knew how to save or spend money, didn’t even know how to balance a checkbook. She would have no clue what to do without him.

  And he stayed with her out of financial fears as well. He had admitted as much when he told me he’d gone to see a divorce lawyer but was advised that he’d have to pay her alimony and half of his retirement savings. And so, with religion being his ostensible excuse or not, it made more financial sense for him to stay miserably married than to divorce.

  I never wanted to be like them. I didn’t want to have to depend on anyone for my financial survival. Nor did I want to have to financially support someone I didn’t love.

  So I had vowed not to entangle myself financially with anyone, or even to commit to the point where it could become an issue. I also thought I had dealt with my problems with my parents and separated my emotions enough that I could talk to them without letting it affect me too much.

  But unlike the grocery shelf I had been leaning on that day when I received the call about my dad, I’m not made of steel. Nothing could have prepared me for my father’s death, and my mother’s anger at me although I suppose neither thing should have surprised me. Parents die. My mom rages. But still.

  And then there was Jimmy. Apparently a stock boy had seen me in shambles and had told Jimmy, the assistant manager of the store. And that twist of fate started our long and convoluted relationship.

  That one vulnerable moment led me to a series of other moments, which brought us to the here and now. The point at which I am trying to break up with him and he is trying to convince me not to, by reminding me of what originally brought us together. And as usual I am feeling guilty because I know he was there for me when no one else was.

  Meanwhile, a seductive piece of lingerie from my new mentor lies hidden in plain sight on the kitchen counter where I once wanted Jimmy to rip off my suit, tie me up, and take me. This time is different from the other times.

  Because I know what real raw lust feels like, and I know I don’t have that for Jimmy. I have it for Asher, even though I know I shouldn’t. It feels so good to be bad and I don’t want to go back to my boring life with Jimmy.

  Chapter 17 – Madilyn

  Jimmy came over to me that day in the store, to find out why a woman was leaning on his display shelf and crying her eyes ou
t. He was very kind to me, and I will never forget that about him, even though this is the end of us.

  “It’s okay,” he’d told me that day, as I’d crumbled into his arms.

  In any other situation, it would be weird. In fact, it would have been totally understandable if he’d have been weirded out. But he wasn’t. He’d hugged me and patted my shoulder.

  “Everything will be okay,” he’d repeated.

  I’d looked into his kind, soft eyes. He was clearly trying to make me feel better, but all I’d felt was sadness and anger.

  “Everything will not be okay,” I’d told him. “My father died. And my mother is crazy. And I’ve spent my twenties trying not to be like her. Trying to show her I don’t need a man, I don’t need anyone. And now… I don’t have anyone. And I do need someone.”

  “How about a stranger who happens to help manage this grocery store?” Jimmy had asked, without missing a beat, and I couldn’t help but laugh.

  “Well… that’s definitely someone,” I’d told him.

  From then on, we were inseparable. Some would probably say we’d rushed things, but it had felt right at the time. Jimmy had cooked for me, cleaned for me, brushed my hair for me when I didn’t have the strength to do any of that for myself.

  He did everything but fuck me.

  He’d even flown with me to Maryland for my dad’s funeral.

  “Look who finally got a boyfriend,” my mom had remarked snidely.

  But I’d just ignored her. I’d felt comfortable with Jimmy by my side, more confident around her while holding his hand.

  I suppose from the beginning that Jimmy’s and my relationship had always been more paternalistic than romantic. He liked that I needed him, and I liked that I could just let go and give in to the feeling of needing someone for once.

  But it clearly hadn’t been meant to last. Had it?

  “Jimmy,” I say now, looking into his eyes, remembering that first day between us in the grocery store. “I really appreciate everything you’ve done for me. I just think we might have… outgrown each other.”

  “So now that you’ve graduated law school and moved on to some big, fancy job, you don’t need me anymore?” His eyes look hurt. He isn’t even trying to hide his pain. “You’re just going to leave me in the dust.”

  I sigh. He knows it’s not like that. Doesn’t he?

  I think with guilt about the naughtiest lingerie I’ve ever seen that is laying on my counter and that I was seriously considering wearing for Asher up until this very moment. I’m not leaving Jimmy in the dust to move on to some depraved relationship with my new boss, am I?

  “Jimmy, you know I’ve been feeling this way for some time. Far before I started this job.”

  Before I met Asher. Before I was… propositioned? In one of the strangest ways ever?

  He nods, and I appreciate the fact that he’s being rational.

  “All those therapy sessions with Mary, all the ‘talks’ we’ve tried to have…” I remind him. “We’ve done our best, but we just haven’t been happy, you know?”

  “I guess you haven’t been, but I have.”

  He stands up and crosses the room to pour himself a glass of water.

  I don’t think he’s telling the truth. If he were happy, he would have been more into me sexually. He would have had sex with me by now. And I would have liked it or at least thought it could be good. The fact that we haven’t done that speaks volumes.

  But I feel so torn. I see my future choices spread out in front of me: a predictable, yet stable life with Jimmy. Or an unpredictable, exciting diversion with Asher.

  I shake my head.

  Not Asher.

  Not like that.

  The whole point was to concentrate on my new career. And Asher would get in the way of that. Even more than Jimmy did.

  “Can you just take a moment and think about this before making any quick decisions you might regret?” Jimmy pleads with me. “I’ll stay at my brother’s. I’ll go tonight. But can we just call it a temporary break? While we think things through? Figure out how to work on things, maybe?”

  I drum my fingers on the table. I like that he said he’ll stay elsewhere tonight. I have a lot of work to do. And maybe he’s right— I’m in no mental state to be making life- changing decisions.

  “Okay, Jimmy,” I tell him, shrugging my shoulders. “We’ll just do that for now, then.”

  “Thank you so much.” He walks back to me and throws his arms around my shoulders.

  I awkwardly return his half hug.

  “How was your first day of work?” he asks me.

  “It was… interesting,” I say, honestly. “And I actually already have assignments.”

  “Okay. Well great. I’ll let you get to that then.”

  He sets down his water glass and turns to leave.

  “Jimmy?” I ask.

  He straightens his shoulders, and I feel another pang of guilt as I realize he thinks I’m going to say, “Just stay,” or something along those lines.

  “Please don’t call me any more at work. We can talk after hours but I need to concentrate while I’m there.”

  “Of course,” he says, sounding disappointed. “And I’m sorry. I was just really worked up.”

  He heads out the door, and I take out the first of the five files, to begin my task of summarizing.

  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 d
epositions, 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.”