Knock Me Up, Boss: A Bad Boy Office Romance

by Juliana Conners

  I sigh, still not completely able to believe that I’m actually admitting it.

  “Well no wonder!” She exclaims.

  Her face is full only of understanding, and solidarity. I’m relieved.

  “I would be afraid of heights too, if that happened to me!” she says.

  Suddenly I have an overwhelming feeling, as if the fear is being lifted from me. I’d been too afraid to ever tell anyone else this story, and I’d just made sure to avoid places that made me fearful of heights.

  But maybe what I truly needed was someone else to truly understand and sympathize with my experience.

  Maybe what I truly need is Chelsea.

  Chapter 27 – Chelsea

  “I can’t believe your childhood was so bad,” I say.

  And then I grimace at my own remark.

  “Oh my god. That wasn’t a good thing to say. I’m sorry. I’m just a bit shell shocked by what you just told me.”

  He laughs, and I’m relieved that I didn’t offend him.

  “Completely understandable,” he says. “But I didn’t tell you to be all woe is me. There were some good times too. My dad and I always played a lot of football together. He actually played for the Wildcats, back when…”

  He pauses.

  “…the team was actually good,” I finish for him, knowing he didn’t want to say it.

  “Exactly,” he says. “And I mean that as no offense to your dad. He’s a great coach but the talent just isn’t there and once a team goes downhill, no good athlete wants to play there.”

  “I know.”

  Poor Dad. I’m glad at least he’s having a winning season now that Wesley has joined the team.

  “Anyway,” Wesley continues. “It’s been hard to have to grow up as the child of someone who sees themselves as this star athlete. There was a lot of pressure. But there were definitely good times too.”

  “I understand,” I tell him. “I’m Coach Thompson’s daughter, after all. Everyone thinks I’m only the head cheerleader because of him. Yet he thinks I can always work harder, no matter what I do or how much success I legitimately earn. So I can’t win either way. And I have a brother who could probably tell a similar story. He plays football too.”

  “I totally get it,” Wesley says. “And I know you work hard. Every day I watch you working your ass off. But not really— because it’s still there and I still love it.”

  I laugh, trying not to blush.

  “I guess part of the reason I told you is that, since you had the unfortunate experience of seeing my parents in action, you know what it looks like to have unhappy parents,” he continues.

  “What do you mean?” I ask.

  “Just that if your dad has found happiness, you should be happy for him. It’s much better than having an unhappy dad.”

  “I see,” I tell him.

  I appreciate what he’s trying to say, but I don’t think the two comparisons are exactly the same. My dad was happy. With my mom. They rarely fought and when they did, they were quick to make up.

  But I get what he means about being happy for my dad and I’m determined to try to do it, especially now that I see what the alternative looks like.

  “Thanks,” I say, but I can’t even get the word all the way out because he’s kissing me.

  “Psychotherapy time is over,” he announces.

  I laugh, but I’m starting to get turned on. Which is odd, considering the very serious conversation we’d just been having.

  “I want to see your body again,” he whispers, one of his arms pulling me into a standing position while the other tugs at my pants. Now I’m standing up in front of him while he’s still sitting on the bed. “I need to be inside you, finally.”

  “I want you inside me,” I say, as he takes off my clothes.

  “You are so fucking gorgeous,” he says.

  He spins me around and runs his hands over my butt cheeks. He squeezes them gently.

  “You’ve got the most perfect ass. Full and firm. I’ve loved how your body looks ever since the first time I saw you on that football field,” he says.

  Then he turns me back around and slides his finger into me while he puts one of my nipples into his mouth. I know he can feel my juices dripping out onto his hand as he fingers me and rubs my clit. I’m so wet and I want him so badly.

  He stands up to take his own clothes off, kissing and touching me the entire time. I squeeze his muscular forearms, mesmerized by how cut and buff his body is. I can’t get over his chiseled chest and washboard abs. I’d never understood the point of tattoos, but now I love how his decorate his biceps and triceps.

  This is it.

  My heart pounds fast as if it can hear the Universe announcing that it’s time.

  As Wesley sucks my nipple and continues to play with me, I can’t get over the fact that I’m about to lose my virginity to the hottest guy I’ve ever seen.

  Then he says, “Here, let me do something I’ve been thinking about since I first met you.”

  He guides me towards the bed and stays standing at the foot of it. I’m on all fours looking back at him as he squeezes my ass once again. I never thought I’d like the doggy style position— especially not for my first time— but I’m so turned on that it feels perfect right now.

  I love the way he’s staring at my body. And I love how his huge cock is inching towards me.

  “God, you have the most perfect pussy,” he says. Then he adds, “I’ll go slow.”

  I can feel the tip of his cock on my pussy. He holds my hips while he gently slides it into me. In this position— or maybe it’s just because of how wet and ready I am— I’m completely opened up and it goes in much more smoothly than I’d always imagined it would for my first time.

  I’d expected pain or fear but I just fear complete abandonment and pleasure.

  “That feels so good,” I moan, as he pushes it all the way inside me.

  “Oh my god,” he says, groaning as he thrusts in and out of me now. “Chelsea. This is amazing.”

  He spreads me completely open, and I lean back into him, wanting— no, needing— his cock all the way inside me. He pumps harder, saying, “Is this okay?” but I’m sighing, gasping, holding onto his pillows for support as I feel a tidal wave of pleasure crashing over me.

  “I’m coming,” I tell him, collapsing my head into the pillow as he continues to thrust himself into me.

  “Good,” he says, grabbing my hips and ass even tighter. “Come on my cock.”

  “Wesley, Wesley, Wesley.”

  All I can manage to do is moan his name as I come.

  He slows down a bit, letting me catch my breath while still working my pussy.

  I’ve never felt this good in my entire life.

  I can feel him pulsing inside me and then he speeds up once again, his hands moving up to grab my breasts as he pumps harder and harder with his cock.

  “Yes,” I say, moving my hips along with him, back and forth on his bed while he fucks me. “I love how you fuck me.”

  “I love how you fuck me too…” he begins, but trails off, his breath becoming heavier.

  Another wave ripples through me as his cock pulsates inside me and I realize we’re going to come at the same time.

  “You’re making me come again,” I say, as I feel him coming too.

  “Oh my god. Chelsea. God.”

  We both moan, our animal instincts taking over instead of words, and then he collapses on the bed beside me. He puts his arm around me and I say, “Thank you.”

  He opens an eye and smiles, saying, “Thank you?”

  “Yeah, that was a dumb thing to say.” I smile sheepishly. “I just… that was really nice. It was perfect.”

  “I’m glad you liked it.” He kisses my neck and I snuggle closer up against him. “As you can tell, so did I. And that’s an understatement.”

  “I think I held off on doing that for so long because after a while it had become this big Thing I Hadn’t Done,” I confess to h
im. “And I was scared that it wouldn’t live up to the incredibly high expectations I’d built up for it.”

  “I hope I helped disprove your fears,” Wesley says.

  “It wasn’t scary at all.”

  “Good.”

  “It was amazing.”

  I’m exhausted yet also exhilarated. I feel like pushing this elation to a whole new level. I want to keep the momentum going, even though I now know that a perfect sex session is impossible to beat.

  But suddenly I get an idea that might come close.

  Chapter 28 – Wesley

  Now that was some incredible sex.

  I’m glad Chelsea enjoyed it, because I want to do it again. And again.

  “Sometimes our fears are scarier in our minds than they are in reality,” Chelsea says.

  “True,” I tell her, glad that she wasn’t scared while we were making love.

  “That’s why I think we should go back to the amusement park.”

  “What?”

  I look at her like she’s grown an extra head.

  “I know you thought bringing me here to have sex was going to get you out of it,” she laughs. “But I think it’s your turn to do something for the first time with me…”

  “Oh, I see how it is,” I tell her, laughing, but I’m nervous.

  “Look, I understand your hesitation,” she says, “and I don’t want to rush you into anything. But we could start small. By the time we get back to the park, I doubt we’d have enough time to wait in line and ride The Beast anyway. There’s a smaller, less popular roller coaster you could start off with.”

  “Is there, now?” I ask, knowing that I’m going to have to do this.

  What kind of a fucking badass will I be in her eyes if I can’t even ride the dinkiest roller coaster in the park?

  “Let’s go,” she says, raising her sexy body from the bed and searching for her clothes. “I’m not ready to stop having fun yet today.”

  “All right, all right,” I tell her, getting up a lot less enthusiastically than she is. “But you’re the only person on the planet I’d do this for.”

  “I know the feeling,” she says, flashing me her gorgeous grin.

  And that right there is enough to make me agree to do any outrageous thing with her, including facing my fear of heights.

  ***

  Chelsea takes my hand as we’re in line for The Rattler.

  “Are you sure you want to do this?” she asks.

  I shrug in what I hope is a nonchalant way.

  “No, but I’m more sure than I’ve been in the past, and that has to mean something, right?”

  The Rattler looms high and menacing above us and I start to doubt that it’s any friendlier than The Beast. The line is long and gives me plenty of time to think about changing my mind but I don’t.

  I try to make lighthearted banter with Chelsea and to tell myself that this is nothing. And although I’m still scared, I’m not nearly as scared as I used to be.

  Finally we approach the front of the line and I smile, looking more confident than I feel as we’re ushered into the loading area and sit down in the seats.

  We buckle in, and then as the ride begins everyone— including Chelsea— lifts their arms over their heads.

  I lift my arms too, the cool night air hitting my face in a breeze of fear mixed with excitement. And then the machine lurches forward, dropping us down and pushing us faster into oblivion.

  “Holy fuck!” I yell, squeezing Chelsea’s hand above us in the air.

  I’m embarrassed but then I realize that Chelsea is yelling the same thing, and so is everyone else on the ride.

  Everyone is scared, and that’s the point. If it hadn’t been for Chelsea, I’d never have realized this one basic fact: I’m not the only person who might be afraid while riding a roller coaster. I was just the only person too pussy to try riding one until now.

  She’s already been teaching me so much: how to fish, how to ride a roller coaster. How to open up and trust someone.

  Maybe this could actually work.

  But as The Rattler embarks on its long, fast descent, my heart jumps up into my throat and I scream in terror along with all the other passengers, but for an additional reason. Because I think:

  What if I’m falling too hard?

  What if it’s too late to get off this ride that I never should have gotten on in the first place?

  I don’t know that I was ready to ride a roller coaster and I don’t know that I’m ready for whatever is in store with Chelsea. With both of them, it’s too damn easy to start out, yet so damn hard to not freak out during the ride.

  And I don’t know how I’ll manage to get off either ride once it’s started. I hate fucking losing control and it’s clear that I already have.

  Chapter 29 – Chelsea

  I’m surprised to see my dad’s car in the driveway when I get home from my secret amusement park date with Wesley.

  I let myself into the house as quickly and quietly as possible, hoping he’s already in bed. I don’t want to answer any suspicious questions. I just want to curl up under the covers and reminisce about everything that’s happened today.

  But he clears his throat and calls out, “Chelsea?” from his study that’s just off the main entranceway.

  Great.

  “Yeah Dad?”

  “Can you come in here please?”

  “Okay.”

  I sigh and walk towards the door, feeling thirteen years old. My mind rushes with possibilities: Maybe he was at Taylor’s mom’s house and Taylor was there, even though she’d agreed to be my alibi. Maybe he just plans to grill me about the details of my day. Why must I get the Grand Inquisition every time I go out?

  But when I open his door he’s staring in frustration at his computer screen.

  “I’m glad you’re home. I could really use your help.”

  “Oh okay,” I tell him, relieved. He looks up at me a bit quizzically, so I add, “I’m surprised you’re home. I thought you would be…”

  I trail off as he continues to look at me funny.

  “I mean, how was your day?” I conclude.

  “It was fine,” he says, with a slight smile on his face. “How was yours?”

  “It was fine. What’d you do?”

  “Not much. What’d you do?”

  “Not much.”

  “I like this plan of keeping our personal lives a little private,” he says, and I quickly nod my head in agreement.

  I guess now that my dad’s been getting hot and heavy with Taylor’s mom, he recognizes the value of privacy.

  “Me too,” I say quickly, definitely not wanting to disagree with the need for privacy between us. “So what is it that you need help with? And why are you working so late? You should be watching Cheers, not cooped up working in your home office on the weekend.”

  Dad laughs. He loves to watch old Cheers re-runs that play on Friday nights.

  “It’s nothing too hard, or at least it’s not supposed to be,” he says. “The academic department upgraded its software across the board and they want me to rearrange my files according to their new fancy system. But I’m a dummy when it comes to computers. I feel really behind, and I haven’t had a lot of time to try to learn the new methods due to… personal factors.”

  “Of course,” I agree.

  “So I got home a bit early tonight and decided I’d try to catch up over this weekend, so I don’t have to go hat in hand to the administration and tell them I don’t know what I’m doing and haven’t bothered to learn it yet. But this thing is so damn tricky.”

  “Okay, let me see what you’re supposed to do,” I tell him, walking up behind his desk chair and peering at his computer screen.

  “This database has a folder for each player, and I’m supposed to move all their documents into each folder,” he says. “Their physical exam results, medical records for check-ups and injuries, their contracts, their disciplinary warnings, their stats, that sort of thing. I’v
e always just kept everything together in one big file that I search when I need something. It’s worked just fine for me in the past, but no, now everyone has to follow this same system.”

  He’s visibly worked up, a bead of sweat appearing just above his brow as his face turns red.

  “It’s okay, Dad,” I say, getting a bit closer so that I can see the database better.

  I place a hand on his shoulder. “I can figure it out.”

  “Do you need this chair?” he asks me, gesturing to the desk chair he’s sitting in. “Or the keyboard?”

  “Yeah, Dad, why don’t you go get yourself a glass of wine and take a little break. You can even catch a Cheers episode if you want. I’ll try my hand at this database and once I figure out how to use it, I’ll show you. That way you’ll know for the future, okay?”

  “Thanks, honey,” he says, standing up and stretching. “I knew you’d be able to help.”

  He leaves the room, whistling the Cheers theme song, and I sit down at his desk. It only takes a few points and clicks for me to figure out the database, which is much easier than the way my dad has been “organizing”— or not— his files.

  I can see why the administration wanted him to upgrade to the new system. They’d probably never be able to figure his out if they needed something.

  I decide to type up instructions in terms of steps he can follow when I’m not around. That only takes me a few minutes, and I don’t want to disrupt his Cheers episode.

  I lean back and sigh, thinking about Wesley’s hands all over my body…

  And then I see his name on a folder in the database, ready to accept his documents. Maybe I should just do one as an example, I think, my palms feeling sweaty.

  Before I can talk myself out of it, I run a search on his name to find his files the way my dad says he does it. Sure enough, a few documents come up: a short physical fitness file, some other boring and generic procedural documents that all the players have to sign, a contract, and then quite a few disciplinary files, which appear to have transferred with Wesley from his former college.