Knock Me Up, Boss: A Bad Boy Office Romance

by Juliana Conners

  I decide I will make it easy for him. I will act like everything is all right, and surely that will fix things. If I behave as though nothing had happened between us, everything has to return to some semblance of normal.

  But it doesn’t.

  He starts to find excuses to come to my office. He begins missing meetings. He stays late to see me or comes in early, hoping to catch me before I start my workday.

  I’m flattered by the attention, but I know things will be coming to a head soon. He makes himself so present, so available, that I have a feeling we’re either going to surrender to the urge again— and this time we’ll go all the way— or I’ll have to leave my job because the temptation is just too strong.

  Chapter 20– Carolina

  A week later, urges win.

  Garrett asked me a couple days ago to black out today— Thursday evening— to work late on a project. I’m still naively entertaining the notion that it could be for strictly professional reasons. He has been doing quite well maintaining his focus and staying away from me except when our work dictates that we spend time close to one another.

  I do my best to remain cool and unaffected by his presence, but as time goes on, I can feel my resolve slipping. If I am to keep my job, this meeting has to be just like any other. I had blocked out the evening, as requested, and by the time Thursday evening is here, Garrett and my attraction to him are the last things on the agenda.

  It really has been an extremely busy day, so working into the late evening on the project seemed the natural order of things. And it is. When I make my way to Garrett’s office, I discover that he had set out several folders for us to review, and things start out rather businesslike.

  “Okay, read me the case summary that the law clerks typed up for us,” he commands, leaning back in his high-backed leather chair.

  I read. He’s engrossed in the summary, even asking me to go back a few sentences and repeat myself a few times. He asks me to go to Lexis to find a case, which I do. It’s all very much on the level.

  Then, as I find a particularly valuable piece of info, I yell out, “Garrett, hey wait! This is precedent setting. This will prove the plaintiff’s case. Our client will be able to win!”

  He steps up behind me to read the screen over my shoulder. I turn back to see his reaction, and it happens.

  The look he gives me lasts a second too long, and then he’s kissing me as if there is no other woman on the planet. I stand up, and he takes me into his arms. Even though we’ve had only one brief encounter, he feels strong, familiar, and safe.

  As we kiss, I pull off his tie and begin unbuttoning his shirt. I slip my hands inside it and run them along his muscled, tattooed pecs and around to his back, his skin warm and smooth beneath my fingertips. As I continue to undress him, he takes my shirt off, and then my bra and my skirt.

  I stand before him in only a skimpy pair of black panties while he wears only his boxers. When he meets my gaze, I can feel that this wasn’t the same as it was the first time. There is no going back now. And I don’t want to go back.

  But as he holds me and we kiss, I know we can’t be foolish.

  “Do you have a condom, Garrett?” I ask.

  It’s been a long time since I’ve had to worry about protection. In my recent past, with Jake, I’d been worried about the opposite— trying to conceive.

  He frowns. “I’m not sure.”

  “Well, find out,” I protest.

  I don’t know who he’s been with, and I have to protect myself.

  “It’s okay, I’ll pull out.”

  “No… that’s not it.” I bite my lip, frustrated.

  I really don’t want to go into my whole history, just to explain to him that it’s not pregnancy I’m worried about. It’s STDs.

  He walks over to his jacket and begins feeling around in the pocket.

  There is no middle ground here. This has been weeks of holding back, holding out, putting aside raw feelings. I need him to have a condom, so that this can happen.

  “Hold on,” he says. “I think I feel one. Yes. I do. I have a condom.”

  It looks pretty old, which definitely isn’t ideal, but the fact that he has anything— old condom or new condom— is a good thing. Better than nothing.

  He returns to me and we begin to kiss once more. I can feel his thick hard cock pressing against my stomach, and I want him inside me so badly I can hardly breathe. I push his boxers down and take his cock in both of my hands. I stroke him until he is rock hard, and then I take the condom from him and roll it over the length of his shaft. He kisses me hard and then turns me around and bends me over his huge mahogany and oak desk.

  I pull my panties down and lets them drop the floor, offering myself to him. They’re bikini style, and my pussy is shaved.

  Clearly I’ve been wanting him, waiting for him, even though I’ve been denying that fact to myself. Torturing myself telling myself I can’t have him, when all along I could have. And now I finally am.

  He caresses my ass and then positions himself directly behind me. My pussy is quivering with anticipation, I want him so badly.

  He reaches between my legs and finds my clit with the tip of his cock. He rubs himself against me, sending shockwaves through my body.

  “Just fuck me, please, Garrett,” I whimper.

  “You want this inside you?” he teases, rubbing himself all over my ass.

  “Yes,” I gasp, nearly begging.

  He pulls back and then finally puts the tip of his cock at the opening to my pussy. He teases me a bit more, gently sliding the head of it in and out of me, while I moan and beg him some more.

  “Please Garrett, please put it all the way inside me.”

  And then, with a single full thrust, he’s inside me. He feels so good. It’s been months and months since I’ve been with a man fully. It’s so perfect, I think I might burst.

  He pulls back nearly completely and then drives himself into me again and again, his pace first slow and sensuous, then faster and more frantic. Before long, he is groaning and panting, and I knew he was going to come.

  I felt my own orgasm rising, when suddenly he pulls out. I lay against the smooth wood of his desk, my orgasm just out of reach. I turn to see what had happened, and he looks concerned.

  “What’s wrong?” I asks.

  “It broke.”

  “What?”

  “It broke. The condom broke.”

  “But you pulled out, right?”

  “Um, eventually.”

  “Well, obviously eventually. I mean you pulled out…”

  “Um, I don’t know. No… I came.”

  “Shit!”

  I feel distraught. But how can I blame him? It wasn’t his fault at all, but after years of trying to get pregnant, the last thing on my mind is daily birth control like the pill or an IUD. The chances of me getting pregnant are infinitesimal.

  He really has nothing to worry about. He hugs me and kisses my neck, and I turn and hold him close, admiring the tattoos lining his chest.

  “Listen, don’t worry. I don’t even think I can get pregnant. My doctor said women with endometriosis have a very hard time, almost always needing IVF. My ex husband and I have been through all of the fertility specialists and still nothing worked. That’s why he’s my ex husband. Well, one of the reasons anyway. But seriously, don’t worry.”

  “Are you on the Pill?”

  “No, but honestly, I can’t get pregnant. Really. The chances are pretty low.”

  “STDs? Should I be concerned?”

  “Of course not. Clean as a whistle. Uh, you are too, I hope.”

  “Yeah. Although this is a conversation we probably should have had pre-sex.”

  “But no, no of course,” I tell him, scrambling to reassure him, even though it’s not my fault the condom broke, either. “No STDs. Look, if you are really worried, you should know that my ex husband, whom I loved very much, left me because we tried and tried to get pregnant and couldn’t. We ev
en tried IVF, and it never worked. The doctors said the chances of success were less than ten percent given we had exhausted all avenues… Ugh, TMI. Sorry.”

  I cross my arms across my bare breasts, suddenly feeling very exposed and self-conscious.

  “No, no it’s okay,” he says, sounding truly apologetic. “I’m sorry that happened to you.”

  “I’m just telling you so you don’t worry for the next month. I promise, it’s fine.”

  But leaning against his chest, I feel like crying. To my horror, a large tear drips out of my eye. And it isn’t like last time when it’s from being completely satisfied. Instead, I feel the sorrow of the last six months of my life overflowing, in a way that I just can’t stop.

  Holy crap, I’m so embarrassed, is all I can manage to think, but he takes me in his arms and holds me, and says, “It’s okay, go ahead and cry. You’re safe with me. I’ve got you.”

  Those are the most reassuring words I’ve ever heard. I lean into him and let myself cry, completely giving into all the feelings of fear, loneliness and sorrow that have been welled up within me for so long. And it feels so completely right.

  Chapter 21 – Garrett

  My poor, distraught Carolina. I hold her in my arms and let her cry on me, wishing I could do more to help. I wish I could kill the bastard who left her just because they couldn’t get pregnant. What a complete asshole.

  I look down at her pretty face and smooth the hair out of her tear-filled eyes. She grasps onto me in a way that’s primal, sexual. Despite my best intentions, I feel ready to go again. My cock rises up, hard and at attention.

  “Oh, my God,” she says, reaching down to grab a hold of it. “You are definitely hard again.”

  “I’ve wanted you for so long,” I admit, leaning down to kiss her head. “And you didn’t even get to finish coming. Let me back in you. Please.”

  She looks up at me, a bit hesitant, and it makes me want her all the more.

  I take off my tie and bind her wrists to my chair. She’s laying ass up on my desk, and she isn’t protesting.

  “The damage has already been done,” I tell her, meaning the broken condom. “But just in case it hasn’t, there are other ways we could…”

  “Really?” she asks, craning her neck to look back at me. “I’ve never…”

  “You’ve never had anal sex before?” I ask her.

  She shakes her head.

  I suppose she wouldn’t have had a need to, since she was trying to procreate. And now, the opposite plan is our goal.

  “Let me take your asshole for your very first time,” I tell her.

  Now it’s my turn to beg.

  I place my hands on her ass checks and stretch them out so that I can see her pulsating asshole. She doesn’t say yes or no, but she’s not really in a position to say anything, tied up on my desk, at my mercy, like she is.

  I put a finger into her ass hole and she jumps a bit, but I grab a hold of her ass cheek once again.

  “Spread your legs further,” I command her, and she does, my compliant assistant. I love seeing her entire naked body, pussy and ass, spread out before me. I smack her pussy with one hand while fingering her asshole with the other.

  When she tries to jerk away, I smack one of her ass checks, and then another, until she’s moaning underneath my touch.

  “Are you trying to disobey your boss?” I ask her.

  “No, I’m not,” she says, as I bring my cock close to her perfect ass hole.

  I spit on it for lubrication and I rub her clit while the head of my cock is up against her ass hole. She’s dripping wet for me, so I take some of her juices and rub them all over my cock.

  Then I push my cock into her ass hole, and both of us moan together.

  “That feels so good,” I tell her, as I slide it into her ass. “I’m taking your anal virginity.”

  “Take it, Boss,” she says, rubbing up against me, giving into me now and letting me do what I want with her.

  I push in and out of her asshole as I rub her clit. She puts her head down on the desk, in the throes of ecstasy. I’m glad she’s able to come now, fully.

  “I’m coming. Garrett, I’m coming,” she calls out, as I thrust in and out of her ass hole while plunging my fingers deep into her pussy.

  And suddenly I’m coming too, filling up her ass hole with my load. When both of us are finished, I pull my cock out of her and watch the pocket of cum I left there drip out of her. It’s a perfect creampie, and I put it in her.

  Both of us are sweaty and messy, breathing heavy now. I take a deep breath, realizing what I’ve just done, and she appears to be realizing the same thing.

  I’ve fucked my secretary. In her pussy and in her ass. With a broken condom, and then no condom at all.

  Holy fuck.

  I pick up her clothes from the floor and hand them to her, and we both get dressed.

  I can’t stop thinking about the risk of her getting pregnant. I know she meant every word she said, but that doesn’t change the fact that she could get pregnant. She isn’t necessarily infertile. I try not to let my concern show, but I have a feeling that I fail. And I also have a feeling that she’s having the very same concerns.

  I decide the best policy is openness. As she’s getting dressed, I lean into her.

  “You know, Carolina, I am in hot water with the partners already. Truly, I can’t afford to get into any more trouble. We just… I just took such a giant risk. But there is something about you. I don’t know. You make me feel like I would take that kind of risk. I would leap first. For you, it was worth it. I shouldn’t have done it and put you at risk too, but it’s going to be okay.”

  “Are you he saying this is it?” she asks.

  “God, no. Whatever gave you that idea?”

  We are clearly on two different pages, as that wasn’t at all what I had mean.

  “I don’t know, that’s just the impression I got from what you just said,” she replies.

  She’s fully dressed now. She smiles and hugs me and goes to walk out of my office.

  I feel like she might be walking out of my life for good. I clearly said something wrong. I’m not used to feeling so powerless. I don’t know what to say.

  As the door swings shut, I sit alone in my office. I’m thrilled to have found someone like Carolina, and I don’t know why I didn’t just tell her that. The words caught in my throat. I was afraid to be too vulnerable, and now it’s too late. I have a bad feeling she thinks that we had made a mistake, or at least she thinks I think that, when in fact I’m thinking quite the opposite.

  Chapter 22 – Carolina

  1 Week Later

  Once we’d had sex, Garrett’s whole demeanor changed. He seemed to avoid me at all costs. Sure, I still work for him, but he keeps everything strictly professional now.

  I suppose it was for the best. I’m not looking for anything serious. Still, all those texts. It seemed as if he could have fallen for me, but it must not be the case.

  In a way, it’s a relief, but I walk around the office each day feeling like I have a huge secret, and it’s weighing on me. I finally confide in Erin.

  “Please, be sworn to secrecy,” I tell her.

  “Of course,” she promises. “I won’t tell a soul.”

  “Not even Claude,” I whisper, although he’s not at his desk; he’s on a lunch break.

  “That’ll be difficult and I feel bad leaving out the third member of our secret society,” Erin says. “But I promise not to tell.”

  “You know that Garrett will be in big trouble with the partners and I could likely lose my job,” I tell her.

  “Yeah, and he would be back to being grumpy all the time about his incompetent male assistants,” she replies. “So, we wouldn’t want that.”

  I laugh, glad for the comic relief. I’m so glad to have made a good friend here.

  She seems to think he wanted to be with me but that I didn’t want it, yet every time I press, asking if she knows anything, she says
no, of course not. Part of me hopes he has confided in her, but apparently, he has not.

  And why would he? It would be very unprofessional for him to divulge his private life to the firm receptionist, especially when that private life involves his having had sex with a female employee. I guess I still had hoped he might have, because he didn’t seem to make the best professional decisions.

  I convince myself that it’s not to be, but I can’t believe how easily he seems to have gotten over me. It’s like in high school when you finally sleep with the jerk and he never calls, but this wasn’t high school. We are both adults. Still, I assure myself it’s for the best.

  I wish I could talk to one of my other new friends about the situation, but I’m afraid of their reactions. I don’t want to get Garrett in trouble, even accidentally. Plus, they have bigger news to pay attention to. Ruby has had her baby.

  I call and congratulate her, and she sounds tired, like all new mothers probably do.

  “Thanks, Carolina,” she mumbles, sleepily. “We’ll have to catch up soon.”

  “Of course,” I tell her, knowing that my issue with Garrett takes a seat on the far back burner compared to her new arrival.

  Every time I see Madilyn and Katie, they’re talking about Ruby’s and Cameron’s baby: telling me what the little one is up to and how long labor took and a bunch of other facts that scare me. Sure, I’m happy for Ruby, but I’ll be even happier once my period comes, as I can’t even imagine going through all of that.

  ***

  As another week passes following our encounter, I try to immerse myself into my work and I refuse to think about Garrett in any way but professionally.

  He doesn’t make that an easy goal. I sometimes find him sitting at his desk with his office door open, gazing at me as I sit at my desk with my office door open— which is the way I usually have it unless I’m on the phone or in a meeting, in case he needs anything— typing briefs or making phone calls.

  If I meet his gaze, he turns away as though he hasn’t just been staring at me. Yet, when I’m near him, whereas in the past he had joked around with me and been friendly, he is now professional to the point that it’s painful.