Knock Me Up, Boss: A Bad Boy Office Romance

by Juliana Conners

  I look at him, knowing that he’ll continue if I don’t press too hard.

  “My ex and I went to a lot of different fertility doctors, trying to get pregnant. We never could. They didn’t really know why. She blamed me. Everything was my fault. She became so cruel. I couldn’t take it anymore.”

  I nod.

  “It’s for the best that we didn’t have a baby,” he says. “I don’t even know if I wanted one.”

  He starts to say more but stops. And I start to feel more. I didn’t think I wanted kids before but maybe it was just because I was with Jimmy. With Asher, I feel like the possibilities are endless.

  I squeeze his hand.

  “I understand. Thank you for telling me.”

  “I’m glad we got that cleared out of the way,” he says, and we both breathe a sigh of relief.

  “Oh my god.”

  I see someone walking in and quickly remove my hand from Asher’s.

  “What?” He turns around and sees who I’m looking at. It’s Janice. And she’s looking straight at us.

  “Hello, Janice,” he says loudly, nodding in her direction.

  She gives a strained smile and says, “Hello Asher. Hello Madilyn.”

  “Oh my God.”

  I just wish I could die of embarrassment. I know that everyone knows we don’t have a strictly business “relationship” but now it’s going to be quite public.

  “Don’t worry about her,” Asher says between his teeth and he flashes her another fake smile. “She’s just jealous. She wanted to be with me way back before I even got with my wife. She’s never gotten over it.”

  I can barely suppress my laughter.

  “We’re just on a business dinner, discussing preparation for the Swartz case,” he says. “That’s all she needs to know.”

  “Yeah, I always wear fishnet stockings to business dinners with my boss,” I tell him.

  I wink at him.

  His foot touches mine under the table and I lift mine up in return. It’s like we’re in middle school, playing footsies.

  He rubs his leg up against mine and says, "I really do like those pantyhose. It's nice to see you in something different from the normal office wear. And I have a special surprise for you.”

  He takes something out of his wallet and flashes it at me. It’s a room key card.

  “Really?” I ask, my excitement rising.

  "I thought we needed to spend some more time together. We have a big case we have to work long and hard on, after all."

  Now it’s his turn to wink, as I know we’re both thinking of what else is long and hard. My heart races at the thought of having a hotel room to ourselves. We've only ever made love at work in his office. Tonight we're taking things to a whole new level. I guess I had expected and hoped for as much— hence the sexy underwear— but I really didn’t know what to expect. To have a room to ourselves is something altogether new and different.

  The waiter returns and Asher orders us dessert. He reaches his hand under the table and places it in between my legs. At various points while talking to the waiter about which dessert we should get, he places his fingers under my panties and inserts them into my pussy, which continually becomes wetter and wetter for him. He also rubs my clit. I swear it causes me to squirm a little bit, but if the waiter notices, he doesn't mind. I keep sneaking peeks at the table where Janice has been seated across the room, but she seems to be purposefully trying to not look over in our direction.

  “We’ll have the tiramisu,” Asher finally decides.

  As the waiter walks away, with a quick flick of his wrist Asher drops the room key card under the table.

  "Oh look at that. Oops. I've dropped something. See?"

  He holds up an end of the tablecloth and at the same time, with his leg nudges my left leg further apart from my right leg.

  Then he raises a mischievous eyebrow and bends down to look under the table. As he does so, he moves my panties away from my pussy, so that it's exposed to him.

  “Oh where oh where could I have put it?” he asks.

  I can’t believe how brazen he’s being. But I love it. I had never in my life imagined showing my pussy to my boss at a nice restaurant but because it was his idea, I don't even mind. In fact, I'm filled with a strange excitement.

  Asher inserts a finger into and out of my pussy several times while he continues to look around under the table for the card.

  Then he says, “I see it and it’s on your side of the table. Do you think you could help me out with that?"

  I quickly look around but don't see the waiter anywhere in sight, and Janice still isn’t looking in our direction. I duck under the table and crawl towards the key card, my ass sticking up in the air for Asher to see under the table. I pull my skirt up high, so that he can get a good look. My underwear are still over to the side where he had pulled them before fingering me, so that my ass and pussy are naked. As I crawl, however, my panties slide back a bit, almost back into their original place.

  "I have your card, Boss," I say sweetly. "It's right under here."

  "You'd better return it to me then," Asher says.

  I turn so that my ass is facing him again and to my surprise he reaches under the table and pulls my underwear back over to the side and uses the strap to pull me back close to him. Surprised, I sit down with my ass on his shoes, and then, feeling as if this is my cue to do something sexy, rub my ass up and down on his leg.

  "You really are a good associate," says Asher, nudging me back up onto all fours with his shoe, and inserting a finger into my pussy as he does. I can't believe how bold he's being— even bolder than he is at the office.

  I lean back into his finger and he says, "I can tell you like helping me find my key card and whatever else I need you to do," while he plays with my asshole with his thumb. He is really enjoying himself, having his way with my exposed pussy and ass, and I let him play until he's good and ready to be done. Then he reaches a hand under the table and squeezes my right nipple and then my left. I begin to wish that we were the only people in the restaurant, because I could do this all night.

  "You assist in any way possible," Asher says. "And you happily go the extra mile to make your boss happy."

  Finally he pinches my ass and lightly slaps my ass as my cue to stand back up. I pull my panties back to their rightful place and pull my skirt back down and then sit back up at the table. I glance around, incredulous that no one noticed this obvious sexual display, but everyone seems to be eating their dinner as normal. The waiter is walking over to us with our dessert, so Asher had told me to get up just in time.

  “We need to eat this dessert fast and then have fun with this key card that you so graciously rescued,” Asher says. “I'm so glad it wasn't lost for good."

  Chapter 38 – Madilyn

  At long last, Asher and I are finally alone. In the elevator from the restaurant floor of the resort to our room, he fingers me repeatedly while kissing my neck and the top of my breasts.

  “I’m so happy we get to do this,” I tell him.

  When the elevator door opens, Asher picks me up and carries me with my legs around him to our room. He opens the door to a spacious master suite and it's immediately clear that he'd been in here earlier, before meeting me for dinner. There are handcuffs tied to the bedposts, a blindfold, and a scarf.

  "Welcome to my lair," he says, and laughs. "I thought you might need to be taught a lesson in here. But you learned it all on your own."

  "I still have a lot to learn." I drop down on all fours again and take off his belt and his pants, cradling his big cock as I do. I take off his underwear and put his cock into my mouth.

  "Yes you do," he says, pulling my head back by my hair as he fucks my mouth. "You have to get it deeper in there, all the way down, the way I like it."

  He takes off my shirt and plays with my nipples while I go down on him. Then he moans and stands me up.

  "Playtime is over," he says, his voice low and deep. "And now I get t
o do what I want with you. You're my pet and I’m your boss. You belong to me and have to do what I say now."

  “Yes, Boss,” I tell him, my knees trembling with anticipation.

  He pushes me down on the bed and says, "Roll over." I had expected him to tie my wrists up with the handcuffs, but not from behind like this. I’m a little bit scared because I’ve never done anything like this before but I trust him. He puts my left wrist in the handcuffs, and all I can see is the pillow beneath me.

  I turn around with my free arm and try to look back at him.

  “Let me take charge,” he says, and takes the scarf and ties it around my mouth. "Just lie there and take it like my good little pet. I've seen how dirty and filthy you can be, and I’m claiming you as my own."

  He puts the blindfold on me, not that it does much in this position, where I'm already facing only the pillow. Then he ties up my right wrist, and my ankles down at the bottom of the bed, using pieces of the rope that stretch out since my legs don't reach that far.

  He takes off my heels, skirt and underwear but leaves my stockings on.

  "Do you like being my pet?" he asks, climbing on top of me and laying his whole body on top of mine.

  I nod into the pillow.

  Yes, Boss, I think, since I can’t say it.

  He sits back and spanks my ass, hard, sure to leave a mark.

  "Did you like it when I fingered your pussy in public?"

  I nod, and he puts his finger into my pussy again and twists it around.

  "And did you like it when I played with your ass in public?"

  I nod again, he spanks me and then plays with my ass, his fingers moving around the edges and slightly inside and back out of it.

  "Well your boss just can’t help himself, whenever he sees this sweet little ass you have,” he says, putting his finger into my ass and playing with it.

  Then he says, "Will you let your boss do whatever he wants to his pet?"

  I nod into the pillow, thinking Yes, Boss.

  Please, Boss.

  More, Boss.

  He puts his dick on top of my ass. He spanks my ass with his cock, which feels strangely nice.

  "That's my good little pet. I love when you let me do whatever I want. But I want your pussy. Just like when I took your virginity.”

  He puts on a condom and then slides his cock into my pussy. It seems to go in easier this time, despite its size and I guess I’m getting used to it. It still hurts a little bit, but I like the pain.

  “I love it when my whole cock is in your pussy,” he says. “I'm going to go until I come.”

  He pulls out his cock and then puts it into my pussy over and over again, thrusting it into me. It’s exciting to be tied up while he does this, and completely helpless in his arms.

  I want to tell him I’m coming, but I can’t so I just moan into the pillow.

  "That's a good little pet," he says, slapping my ass a bit more softly, and then pulling my hair. "You're my good little pet, coming for me. And now here I come. I'm coming."

  He lifts his cock out of my pussy and yanks off the condom, spraying my back with his cum. He makes a long line up and down my back and ass.

  "There you go. That's my pet. I needed to claim you. You’re only mine and no one else’s.”

  He unties me and says, "Now let me clean up my dirty little pet.”

  There's a large Jacuzzi bathtub and two-person shower in the master suite and we get into it together. I lean my head back, relaxing, and he says, "Not so fast. There's one more surprise for you."

  He takes the shower head down and sprays it into my pussy. He holds my ass up high while licking my clit while the water hits my hole. It feels so good for his tongue to lick all over my clit while the water pulses into the rest of my pussy. I come so fast that it feels like my whole body is melting into his.

  "There you go," he says, turning off the shower head and scooping me into his arms as the jets hit us from all angles. "Now we’ve officially consummated our relationship the right way.

  I lean back and relax, wanting to know what exactly he might mean by “relationship,” but I’m too scared to ask. I don’t want to mess up a good thing. So I just relax and enjoy what I feel is the best night of my entire life.

  Chapter 39 – Asher

  THE NEXT DAY

  Lately I’ve been on a natural high better than the ones I get from climbing mountains or running a lot.

  I’m used to getting what I want, but I’m not used to liking it so much.

  I’m on cloud nine at work, ready to kick ass, take names and make a ton of money in the Schwartz case and loving that things are working out so well for Madilyn and me.

  And then I get a phone call.

  “Darling, how you are doing?” A familiar and annoying voice asks me on the other end.

  It’s my fucking ex-wife.

  “Stop calling me,” I tell her.

  “Well, well, well,” she says. “Look who finally grew a backbone.”

  I hate it, but she’s fucking right. I should have told her off a long time ago.

  “I was just wanting to let you know I heard some rumors about this newest pet of yours,” she says. “In the past you’ve liked to have your fun but you’ve kept it discreet. This time apparently you’ve pushed the envelope a little too far.”

  “What are you talking about?” I ask her, irritated.

  “Oh, don’t you know that Janice and I talk?” she asks, and I shake my head.

  No, I didn’t know that. But it makes a lot of fucking sense. Two of my least favorite people, colluding against me because they have nothing better to do than to try to ruin me.

  “We’ve kept in touch ever since the divorce,” she says. “Apparently she thinks you’ve been a very bad boy around the office. And not even the founding partner can get away with that forever.”

  “What are you talking about?” I ask her again.

  “Oh nothing,” she says, nearly signing the words. She’s gleeful with pleasure. “I just wanted to call and say don’t forget I warned you that you could never be happy trying to replace me with these naïve little ‘pets’ of yours. Tu-ta-lo.”

  She hangs up before I can get another word in.

  What the fuck?

  I don’t know what she’s fucking talking about, but I know it can’t be good if it involves Janice. Leave it to Janice to try to ruin my life. And leave it to my ex-wife to gloat about it.

  I head down the hall to go warn Madilyn that something’s amiss. I don’t really know what is happening but I want an excuse to see her. And I know she’d appreciate the heads up.

  But as soon as I get to the lobby, Ron Sanchez is standing there, as if he was debating whether to come to my office or not.

  “Oh, hello Asher,” he says, looking down at his shoes. “I was just coming to let you know you’re needed in Conference Room A. I thought I should come tell you myself.”

  “I’m needed in…”

  What the hell?

  I can’t even finish asking the question because it’s so ludicrous. They’re acting as if I’m a brand new associate getting in trouble for filing something wrong. Not the head and founder of this fucking firm.

  “What is going on, Ron?” I ask, upset that he’s approaching me this way.

  “Let’s just go to the Conference Room,” Ron says. “The head of HR is there and he can explain further.”

  The head of HR? I hired that fucking moron. He’s so scared of me he never looks twice at me. But suddenly he’s so important that he has to tell me something that Ron can’t?

  “Whatever, Ron,” I say, beating him to the elevator before I beat him up which is what I feel like doing. “So much for thirty years of friendship. If this is how you’re going to treat me.”

  Chapter 40– Madilyn

  I haven’t been in my new office very long and already I’m being called out of it and to Conference Room A.

  Great.

  I just knew it was bad news when Janice s
howed up at the restaurant. She’s always had it in for Asher and we just gave her the perfect excuse to bust us.

  I knew that being with Asher caused a risk for me at work. I just didn’t think it would happen so soon, especially after it was kind of openly known and accepted that he indulged himself in dalliances.

  As I obediently follow the HR manager into the Conference Room, I look around and see that Asher is already here. His eyes say “Don’t say anything,” and I wasn’t planning to. He nods at me and somehow despite this shit show I feel that he will protect me, that I will be safe.

  Suddenly Mandy Calderon walks in and smiles at me smugly. I glare at her. She sits down beside Janice and I guess they’ve suddenly become best friends. Cameron Sanchez is here but other than that it’s just Asher and me and the HR manager. At least I’m not being publicly shamed. Or at least not yet.

  “We’re here today because of very serious accusations of sexual harassment,” the HR manager says, looking down at the paper in his lap as if he can’t bear to accuse us directly.

  “On what grounds?” Asher demands.

  “Mandy here says you have sexually harassed her,” Janice says, patting Mandy’s knee as if she’s a little kid who needs someone to stick up for her. Meanwhile Mandy is giving me a gloating look like she just won some contest.

  “I most certainly have not,” Asher says.

  “And I saw you and Ms. St. Clair at the Alcove last night,” Janice continues, shooting me a disapproving look. “And it did not look like a business dinner.”

  Mandy’s eyes nearly bulge out. Apparently it’s the first time she’s heard that Asher took me to the Alcove. Now it’s my turn to win the contest I hadn’t even known I’d entered.

  “Let’s take one accusation at a time,” the HR manager says. “Ms. Calderon, what exactly are you alleging Mr. Marks did to you?”

  “What did he do to me?” Mandy explodes. “He did… well, he did nothing. What he did was pick Madilyn over me.”

  I have to try hard to contain my laughter. I raise my eyebrows at Asher, stunned that she just said that.