Please Boss: A Bad Boy Office Romance

by Juliana Conners

  He raises his eyebrows at me, as if pleased to hear my answer.

  “Sir, I’m—” I start to stand up and introduce myself properly, but just like everyone else who has been in here today, he is already walking away.

  Except he didn’t even tell me his name.

  I know that my two goals of having sex for the first time and doing well at my new career mean that I can’t sleep with anyone from work. Like everyone else in the world, I must have a rule not to sleep with co-workers. But as I stare at his well-toned ass as he walks away from me, I can’t help wishing I could find some loophole to that universal rule.

  Chapter 3 – Madilyn

  Just as soon as the handsome, mysterious, authoritative man walks away, my phone starts ringing again.

  Shit.

  I’d managed to switch it to vibrate but it still sounds really loud. I hit “ignore” again as fast as I can and look around to see if he is disappointed again. But he’s already gone.

  I don’t know whether to be sad about that or happy that he left so quickly that he didn’t know I’m already getting another call so soon after he told me no phone calls are allowed in here.

  Mostly, I’m relieved he’s gone before the office drama I thought I had dealt with at home followed me to work. I had made it my goal to break up with Jimmy before I started working here and I’d done my best to accomplish that goal.

  I’d tried to break things to Jimmy nicely.

  Yesterday I’d told him, “Look, it’s just not working.”

  It was an understatement, to say the least. Some of my friends have wondered how I made it to the age of twenty-three while dating someone on again, off again for three of those last years and still remaining a virgin. To make the situation even crazier, we had even started living together without sleeping together. And of course everyone always wants to know how we pulled that one off.

  I always tell them that it just didn’t feel right to me, implying that the timing didn’t feel right or that we were waiting for marriage. But that's because the real reason is so much more embarrassing: Jimmy never seemed into having sex with me. We would fool around and I would push for more or suggest it and he would say he had a headache or was stressed from his job as associate store manager.

  Meanwhile I was working my ass off in law school and as a law clerk and I began to crave sexual release that he just had never been wanting to give me.

  I thought that if I invited him to live with me in the townhouse I was renting that the proximity of being near each other and the seriousness of the relationship would make it more natural for us to start having sex. But instead the opposite happened: I think I made him feel claustrophobic and as if I was putting too much pressure on him.

  I began to feel stupid practically begging him to have sex with me when he always resisted my advances. I wondered if he was gay or asexual but he watched porn featuring women and straight couples. So I began to feel that the problem was that he's just not that into me or for some reason he lacks the ability to have sexual intimacy with a real life partner.

  We had even gone to couples’ counseling— who does that when they’re not married, engaged, or even having sex? Mary, our round faced, curly haired counselor who reminded me of a Cabbage Patch Doll had told us we were living more like brother and sister than like a couple and she urged us to consider progressing into a “sexual relationship.”

  She assigned us homework from a book called Hot Monogamy for Dummies that instructions to write out our perfect sexual fantasy with our partner.

  I’d spent over an hour describing mine. The essence of it was this:

  I’ll come home from work and he’ll rip off my clothes and fuck me hard on the kitchen table.

  I’ll say, “Don’t be so rough,” and then I’ll say, “Just kidding, keep being as rough as you want.”

  He’ll turn me over and tie my hands to the kitchen chair so he can spread my legs, grab my ass, and fuck me from behind.

  We’ll come together, his warm, juicy liquid filling me up and dripping out of me onto the table after he takes his cock out of me…

  Imagine my surprise when we arrived at our next session and I saw Jimmy’s description of his perfect sexual fantasy with me:

  It’s late and we get into bed to cuddle. The lights are off and there’s slow music playing. I kiss her and then insert a finger into her and then we have sex. Then we fall asleep.

  That was it. That was the entirety of the best vision of our sex life that he could dream up and write down.

  And that’s when it dawned on me that things are never going to change. We’ve been together off and on for four years but we’d never even had sex, and the sex we wanted to have with each other hadn’t even matched up.

  I had told my sister about couples’ counseling and about how shocked Jimmy had looked about my sexual fantasy.

  “At first we both wanted to save ourselves for marriage but now it’s like, how can I marry someone when I don’t even know if the sex will be any good?”

  “I think he has some weird sort of virgin/ whore mentality going on,” my sister said, diagnosing not only Jimmy but also the state of our relationship more honestly and accurately one minute after hearing about that session than Mary had been able to do after months of counseling. “I just think he isn’t able to see you as anything other than his white dress- wearing future bride.”

  “He’s never going to be able to defile me the way that I’ve come to realize I need,” I’d admitted to her.

  “You should just jump his bones,” she’d said. “I’m sure he wouldn’t protest.”

  “He might,” I tell her. “Just like the look on his face showed me he was protesting against my perfect sex fantasy.”

  And to be honest, I didn’t even want to have sex with him anymore. That’s when I’d decided to break up with him for good and lose my virginity to someone else. Someone whose fantasies and real-life tastes might be more in tune with my own. And that’s when I’d gone on this mission to lose my virginity to the right person. Or at least a person who would know how to take it from me the right way.

  All this time of living in an unsatisfactory sexual relationship has taken its toll. I’ve wanted to call it off for a long time, and last night was my chance. It was yet another sexless, boring day, when Jimmy had told me after dinner that he was going to “hit the sack” early. (That was his phrase— not mine. Sometimes he talks like an old man. And he even insisted on sleeping in the guest bedroom because he didn’t want to “soil” our future marriage bed.)

  Realizing that I should have said something a long time ago, I decided to speak up last night. I’d been trying to work up the courage to do it for a while, and I was frustrated enough that it was the perfect time. In fact, the first time he had ever gone to bed without having sex with me should have been the last time.

  “Jimmy. I can’t do this anymore.”

  I’d never been so relieved to finally be able to utter those words, but he looked crushed.

  “Let’s sleep on it,” he’d said, in his usual non- confrontational style. “You might feel differently in the morning.”

  This morning, I did not feel differently. I strapped a leash on my dog Lucia, as I do most mornings, and took her for a jog.

  Thinking that maybe Jimmy wasn’t as sexually into me as he used to be because I’d gained a few pounds, I’d taken up jogging a while ago. It didn’t make Jimmy become any more interested in me sexually, and it didn’t help me lose weight— I like New Mexican food a bit too much to make sure my diet matches my strict exercise regimen— but the jogging routine helped me clear my head and have time to myself.

  This morning, I’d thought about how long and hard I’d worked to get to this place in my career. I’d gone straight from kindergarten through law school. I’d made Law Review— an elite panel of law students chosen to write and edit legal articles for the school’s legal journal— and I’d gotten good grades.

  I’d gotten a pretty good
summer clerkship and this very good permanent associate job offer. All that mattered now was doing a good job at my new job, climbing the associate ladder to partnership and being a successful lawyer.

  I didn’t want to let my old relationship problems get in the way of my new career.

  When I got back home, I dressed in my most expensive and best- looking suit— the same one I’d worn when I’d interviewed and gotten this job— and told myself in the mirror that I could do it. Today was my day.

  Jimmy was awake and he looked at me hopefully. I know him too well to hope that he would be the one to bring up last night’s break- up, even though I also knew it was on his mind.

  It was clear that it would be up to me to keep doing the dirty work.

  “Jimmy,” I said, trying to sound kind but business- like. “Do you have somewhere to go? Your brother’s?”

  “I— I thought—”

  He’d looked down at the carpet but he didn’t say anything further.

  “I’ll probably stay late at work today, since it’s my first day and all,” I told him.

  I wanted to say that while I knew he worked today, I thought it would be best if he could get his essential things together after work while I was still gone, and stay with his brother overnight.

  But I didn’t want to be cruel. I was hoping he would read in between the lines.

  “I have to go now,” I told him, rather than discussing it any further.

  “Have a good first day,” he’d told me, his eyes still downcast.

  And now he’s calling me, twice in a row, when I’m not supposed to be taking calls here in Cubicle Hell, even though there’s not much else for me to be doing.

  I finally accept the writing on the wall: he’s not going to leave me alone until I talk to him more bluntly about what I want, or more like what I don’t want. I know I had to get it over with. And then I’ll be free to fantasize guilt-free about Mr. Mystery Man.

  I’ll just insert him into the fantasy I wrote for Mary. From the way that he raised his eyebrows at me when I called him “Yes, Boss,” I think Mr. Mystery Man would appreciate my fantasy a lot better than Jimmy did. And he’d probably be able to help me out with it in real life, too, if it weren’t for the fact that we’re co-workers.

  Chapter 4 – Madilyn

  I excuse myself from Cubicle Hell— although the paralegals rushing around are too busy to notice or care that I’m leaving— and head down the fifteenth floor hallway to try to find somewhere private to talk.

  The only place I can find is the bathroom, so I lock myself into the furthest stall and call him.

  And that’s where I still am now.

  He answers on the first ring.

  “Madilyn,” he says, his voice sounding as if he hadn’t slept all night.

  Since we don’t even actually sleep in the same room, it’s very possible that he hadn’t slept a lot and I hadn’t known about it. But I can’t give in to feeling guilty and stopping myself from doing what I need to do.

  “Thank you for calling me back,” he says. “I just had to talk to you—”

  “Jimmy,” I hiss, in a hoarse whisper.

  No one else is in the bathroom, but I don’t know when anyone might come in. “I’m at work. Aren’t you, too?”

  “I can’t go to work. I’m too upset. My stomach hurts. Just tell me it’ll be okay. Please don’t break up with me.”

  “Jimmy,” I tell him. “It’s really for the best. You can find someone you’re more… into. Compatible with. Attracted to.”

  “I’m into you,” he insists. “I know I haven’t always shown it…”

  That’s for sure, I think, but I don’t say anything.

  “But I’ll try harder. Mary can help us.”

  I can’t count the number of times he’s promised that. And our sessions with Mary only seem to be making our problems— and their lack of a realistic solution— even more obvious to me.

  “Jimmy, I have to go,” I whisper into the phone. “Please don’t call me at work anymore today.”

  “Just promise me you’ll talk to me later.”

  “Fine,” I tell him, just to get him off the phone.

  I lean back onto the wall behind me and breathe a sigh of relief. At least I’ve gotten him off my back for now. I won’t get in trouble from Mr. Mystery Man any more.

  Although, I have to admit I’d like to get into trouble if it involves that rugged, handsome stranger. Maybe he’ll spank me.

  I smile as I surprise myself with the thoughts. I’d vowed to be more open to things sexually, and I suppose that means in my fantasies as well. I reach down between my legs and feel the wetness dripping out. Just one thought of that sexy stranger and the way he made me want to say “Yes, Boss” even though he’s not my Boss fills me with delight and intrigue.

  I rub myself gently while thinking about unbuttoning that shirt he so casually wears. I want to rub my pussy all over his chest. I can’t believe I’m even thinking of these things. I imagine myself straddling him and sliding up and down his big, muscular, toned chest and entire body with my wet pussy.

  I’m really wet now and decide to go all the way with my fantasy. I imagine that his cock is huge and that I slide down onto it and lower myself on top of it. In my mind I ride his hard cock while in real life I rub my clit until I’m coming. I’m gasping for air and holding onto the side of the stall with my free hand, wishing I knew his name so that I could call it out even in my mind, determined to find it out so that I can…

  Mmmmmm, I moan under my breath, not even caring that I just made myself come in a bathroom stall on my first day of work. I don’t care that this isn’t like me— I love giving into it. I can only imagine what I might do if that handsome man so much as touched me with the tip of his finger. I think I would go wild and just stick it in my mouth and just start sucking on it.

  I’m really hoping I can see this man again and that somehow he can fulfill these crazy fantasies I have without us getting into trouble at work. And if not, at least I can think about it and make myself feel better than Jimmy ever could.

  Chapter 5 – Madilyn

  After my private daydreaming session involving the man whose name I don’t even know, I’m full of pleasure and the sweet feeling of release and I'm ready to re-start this day. Then I hear the bathroom door open and the sound of women laughing as they enter the bathroom.

  Shit.

  I can tell through looking through the slim cracks between the door hinges of the stall that they’ve congregated in front of the mirror. They must have just gotten to work and decided to finish their primping together here in the bathroom.

  I wonder if they could have possibly overheard any of my “me time.” But at least they couldn’t have been anywhere close to the bathroom soon enough to hear my conversation with Jimmy. I don’t know which would have been more embarrassing.

  I decide they seem oblivious and that they don’t even know I’m in here. I quickly pull up my feet so that just in case they heard anything, they can’t see my shoes and later identify me as the sad sack in the bathroom who was trying to break up with her boyfriend on her first day of work. Or the horny lady who couldn’t even wait until her first day of work was over to get off by thinking about some guy she doesn’t even know.

  “I wasn’t sure how early to get here before the start of new associate orientation,” one of the women says.

  I squint through the crack between the door and the stall to see who she is. I vaguely recognize her and one of the other women from a mixer the firm threw last week so that the new associates could get to know each other.

  Most of them had been summer clerks here at the firm last year, so I was one of the few new people, and I’m not very good at getting to know people.

  I think her name is Tara and she has hair as blonde and legs as long as Barbie’s. In fact, they all three look like some version of Barbie or one of her friends.

  I know the third woman a bit better because she was in my cla
ss section of law school. But that doesn’t mean we were friendly.

  I had thought the era of mean girls ended in high school. In law school, however, I found that we as a class had apparently regressed back to middle school. There were cliques, there were post-finals celebrations that rivaled college frat parties and there were definitely mean girls. I tried to avoid the “mean girls” and keep my head in the books while they threw themed parties or networking events.

  And now, on my first day at the law firm of Marks, Sanchez & Reed, I’m learning that mean girls are still alive and well. But it seems to be par for the course for my first day at my new job, my new career, my new forever.

  Just as I was surprised that “mean girls” rule the law firm world just as much as they did the middle school lunch cafeteria, I’m also surprised by how many young, attractive females become successful associates at large firms.

  I know I should count myself among them but I’m sure they don’t. Although I’m young, I’m curvier and bustier than most of them, and I don’t care about plastering my face with tons of makeup or doing my hair in the latest style.

  “I’ve heard that the orientation is I boring,” says another of the girls— Candace, the one with whom I’d shared law school classes— “So I downloaded some of the most recent issues of Vogue onto my iPad. What did we learn in law school, if not to always be prepared?”