Bigshot Boss: A Bad Boy Office Romance

by Cat Carmine

“Can you keep your voice down?” I haven’t even been in the office twenty minutes and she’s already harassing me about my date with Mister Bigshot.

  “What, you don’t want anyone knowing you have a date tonight?”

  “Sloane!” I plead, looking around to see if anyone heard her. Jim glances over at us but then looks away, apparently uninterested in our antics.

  “Come on, I want details! It’s been a lifetime since I went on a date. I need to live vicariously.”

  “I don’t mind talking about it, just not in front of the whole office.” I’m the newest one on the team and people are still getting to know me — the last thing I want to do is develop a reputation as anything less than serious. Despite my distaste for Charlene, this is basically my dream job and I intend to rock it.

  Sloane pouts. “Fine. Coffee later, then.” She leans over to look at the time on my computer monitor. “We’ll go at ten o’clock sharp. I need caffeine and gossip.”

  “Fine,” I agree, laughing. I’m pretty sure she wouldn’t let me say no even if I wanted to.

  I work as diligently as I can for the next hour, even though my mind is having a hard time focusing on the words in front of me. My stomach is already knotted in anticipation of tonight.

  When Sloane pops her head into my cubicle again, I’m actually grateful for the distraction.

  “Let’s go,” she says but I’m already hopping up out of my chair.

  As soon as the elevator door closes behind us, Sloane is on me.

  “Are you going to sleep with him?”

  “Sloane!” I act appalled, although the idea has definitely occurred to me. In fact, it’s been the only thing running through my mind for the last few days, ever since I agreed to the date. Would I sleep with him? Would he even want to once he met me?

  “Come on,” Sloane says, checking her reflection in the mirrored wall of the elevator and and tucking a stray strand of wavy blonde hair behind her ear. “You’re a modern woman. You’re allowed to have sex on the first date.”

  “I know. I just … I don’t want to disappoint him.”

  “Psh. Men are never disappointed about getting to have sex.”

  Ha. If only she knew.

  “It’s just that I think he’s probably more experienced than I am.” I hesitate. “I’ve only ever been with one guy,” I admit.

  “The ex-boyfriend?” Sloane has heard me mention him a few times.

  “Matt. Yeah.” I take a deep breath. “I don’t think he thought I was very good at it.”

  We step outside. Sloane squints but I don’t know if it’s at me or at the harsh sunlight. We both pull on our sunglasses. “Good at what?”

  “It.” I hiss the word, praying she won’t make me say it.

  Sloane stops dead in her tracks. “Oh, sweet Jesus. What makes you think that?”

  I hesitate, but then finally spit it out. “He told me.”

  “He…what?” Sloane sputters in disbelief. If I wasn’t so mortified, it might actually be funny.

  Instead I nod pathetically. “It was part of why we broke up,” I whisper. “He said I had no imagination. No … passion.”

  It’s humiliating to admit. Almost as humiliating as it was to hear those words coming out of Matt’s mouth… and that had nearly broken me.

  I’d met him just after getting out of college, and he’d seemed like the perfect guy. Very sweet and handsome enough, and with a good job in finance — exactly the kind of guy I always thought my parents hoped I’d end up with some day. But as the months went on, he seemed to get more and more annoyed with the things I did. He’d complain about the time I spent with Ally, the nights I had to work late. We stopped going on dates. Then we stopped having sex. Then he stopped calling altogether. When I finally managed to get him to agree to meet with me, he told me impatiently that I bored him, and that he could never love someone who was so inherently dull.

  I had cried for a month. And eventually I had to admit that it wasn’t because I was all that terribly sad about Matt. (He was a bit boring too, when you got right down to it). I cried because I was afraid he was right. That I was fundamentally boring. That I had no passion. That I would never stir a man the way other women could.

  Sloane hands me my coffee. “Look, honey. Relationships take two people to work and two people to fail. If you weren’t passionate it’s because he didn’t make you feel passionate.”

  I’m glad I have my sunglasses on so she can’t see the grateful tears welling up in my eyes. It feels good to finally tell someone about Matt. I don’t know if I necessarily believe her, but it feels good to put it out there into the world. Get some air on it.

  “Now,” Sloane says, once we’re out of the coffee shop again. “I think you’re lucky to be rid of that loser. I think what you really need is to get back on the horse. And I think your internet lover is just the way to do that.”

  I can’t help but laugh. “Oh God, don’t call him my internet lover. That sounds so gross.”

  “Fine. Your online boyfriend? Your cyber hunk? Oh, I know, your digital dreamboat.”

  “Please just stop talking.”

  Sloane elbows me as she laughs. “I’m sorry. I’ll be serious. And I seriously think you should stop worrying and just get yours. Even if it doesn’t work out long term with this guy, it’ll be good to get your confidence back.”

  “Maybe,” I allow, thinking about her words. “Maybe.”

  Can I do that though? Just let go for a night? I have no idea, but I have a feeling I’m going to find out, one way or another.

  After all, Mister Bigshot doesn’t seem like the type to take no for an answer.

  That evening, I spend a ridiculous amount of time getting ready. We had made plans to meet at L’amour, a French restaurant on the east side. I model about eight different outfits for Ally and even though she insists each one is fine, I still end up changing three more times. I finally settle on a simple black sheath dress with a thin gold belt.

  Remembering my conversation with Sloane, I take the extra time to shave my legs. Just in case. I’m not presuming anything … but just in case.

  Once I’ve done my make-up and spritzed a soft perfume behind my ears, I lean over to give Ally a kiss goodbye.

  “Have an amazing time,” she says. “Text me if you need anything. And if you’re going to be late.”

  She winks and I groan. Why is everyone assuming I’m just going to fall into bed with this guy?

  I take a cab to the restaurant so I won’t have to navigate the train in these heels, which are about three inches higher than anything I’ve worn before. When the driver pulls up in front of L’Amour, I take a deep breath. The cab driver is watching me in the rearview mirror.

  “Can I ask you something?” I ask, before I get out.

  “Sure.”

  “Do I look like a boring person to you?”

  He rolls his eyes. “Lady, I don’t know. I drive a cab.”

  “Right,” I say, embarrassed. I start to get out of the car.

  “Hey,” he says, leaning over. “You’ve got nice legs. I’ll give you that.” He’s smiling.

  “Thanks.” I shake my head as I get out of the cab. What is wrong with me? This date has gotten into my head in a way that is seriously starting to scare me.

  I want to say that Mister Bigshot is just a little online fling, but the truth is, I enjoy his messages. They’re sweet and sexy and funny. He’s sweet and sexy and funny.

  And in a perfect world, he’s someone I could develop real feelings for.

  But there’s only one way to find out for sure. I take another deep breath and pull open the heavy wooden door of the restaurant. The hostess, a beautiful dark-skinned woman in an ivory satin dress, gives me a cool smile.

  “I have a reservation. Under L.M.” For Lovemail, he’d explained.

  “Of course. Your other party is already here.”

  I suck in my breath. This is really happening.

  The hostess turns on her heel and s
tarts to walk back into the restaurant. I scurry to keep up. The restaurant is dark and crowded and my eyes rove wildly around the room, trying to find a table with a single man, trying to figure out which one might be him.

  Then I stop.

  Freeze.

  The hostess keeps walking but I can’t move a muscle. The rest of the room seems to fade away until all I can hear is my own heartbeat, thudding in my ears.

  And the only thing I can see is him.

  Mister Bigshot.

  Only that isn’t how I know him.

  I know him as Trent Whittaker.

  9

  Trent

  I check my phone. Still nothing new from Luke. Instead I flip back to the article in the Post, the one that pointed out how many retail stores we’d closed this year and that speculated that Loft & Barn was going to post a loss this quarter, for the first time in our ten year history.

  I keep coming back to the section of the article that talks about the 2,500 people who work in our three hundred retail locations, the two hundred people who work in our head offices here in Chicago. I think about all those people, and how their livelihoods all depend on me and Luke keeping this company profitable. I don’t always like the decisions I have to make, but I’m always thinking about the people who work under me, about what I can do to make sure their jobs are safe. Even if that means getting them to work unpaid overtime once in a while.

  Thank God I have this date tonight to distract me. Finally meeting SweetVixen will give me a good excuse to just put all this other stuff aside for a while.

  I look through my closet, hoping inspiration will strike. The Hugo Boss suit? The Armani? Or should I go more casual with jeans and a blazer? Which would she like better?

  I want to give myself a shake. This is ridiculous. Since when do I worry about which of my clothes a woman will like better?

  Well, I know the answer to that, don’t I?

  Not since Lara.

  I shake my head. She’s the last person I want to think about tonight. Tonight is about finally getting to bang the woman who’s been teasing me all month long. No more, no less.

  Then why the fuck am I stressing over what suit to wear?

  I grab the slim cut black Calvin Klein and slam the closet door shut. Who’s stressing? I’m not stressing. I’m going to wear this suit and I’m going to look damn good in it and that’s the end of it.

  I still have time before I had to leave, so I grab a beer out of the fridge. Just to take the edge off.

  I take a long swig, cursing myself again for letting this correspondence drag on for as long as it has. Never again. I would get this SweetVixen out of my system and then it was back to my regularly scheduled programming: find a hot woman online, one who had more than two brain cells to rub together, take her to dinner, take her home, never see her again.

  That system has been working for me just fine for the last five years, and I see no reason to change things up now.

  I scan the apartment with a critical eye, trying to imagine how it would appear to a woman. No porn accidentally lying around? No remnants of ex-girlfriends?

  But of course, the apartment is spotless, thanks to Agata, my cleaning lady.

  It’s also a virtual showcase for the history of Loft & Barn. I have all of Luke’s best pieces here — the rich espresso leather chesterfield from three years ago, the walnut nesting tables from our second year in business, the pedestal table and the wingback chairs. Most of this stuff isn’t even available anymore and would be considered collector’s items. I would probably get ten times what we originally sold them for — or I could, if I wasn’t so attached to them. I’m damn proud of the company Luke and I have built, and my brother is the most visionary man I know.

  I hate that I’m crippling his vision by taking the company in this new more mainstream direction.

  I finish off my beer and say another silent prayer that he’s able to pull something together soon. We have to knock it out of the park with this collection. I can already feel Lara’s glee at being able to pan us — and there’s no way I’m going to let that happen.

  By that time I’m more than ready to get out of the house … and more than ready to finally meet my SweetVixen. I text Ted, my driver, and let him know to bring the car around, check my reflection in the mirror one more time, and then hit the elevator.

  L’amour is bustling, as it always is. It’s impossible to get reservations here, unless of course you’re me — in which case it’s only slightly less impossible. I wanted to go all out tonight — again, something I can’t really explain. I just feel like I have to impress SweetVixen. You know, show her that I can wine and dine her as well as any man, that I’m more than just a filthy mouth and a stiff cock.

  Though I’m definitely both of those things too.

  I’m a little early getting to the restaurant, so I’m not surprised to find that she’s not there yet. The hostess shows me to my table, and it doesn’t escape my attention how much she wriggles her hips in front of me as we walk through the restaurant. She’s very attractive — dark skin and a slinky white dress — and normally I’d be all over that, but today it does nothing to stir me.

  There’s only one woman on my mind right now. And one woman I want on my cock tonight.

  I order a bottle of Beaujolais and ask for two glasses. SweetVixen had mentioned once that she liked fruity reds, so I hope she’ll enjoy this one.

  I realize that I still don’t even know her real name yet. I find myself wondering what it will be — something worldly and sexy, no doubt. Alexandra, perhaps, or Celeste. Francesca.

  When the wine arrives, I taste a sample and then have the server pour me a glass which I savor slowly while I wait. I take out my phone and start going through my endless stream of work emails while I try to kill time until she gets there.

  Eventually I get caught up in what I’m doing and barely notice how much time has passed. I’m flying through my emails, ticking things off my to-do list, and then I stop.

  I don’t know why. Something makes me look up.

  That’s when I see her.

  SweetVixen.

  I don’t know how I know it’s her, but I do, as sure as I know my own name.

  She hasn’t noticed me yet so I watch her as she follows the hostess towards my table.

  She doesn’t look anything like what I expected — or like my usual type. I usually date blondes, tall and sleek. This girl is short, even with the five-inch heels she’s toddling on. She’s curvy and soft in all the right places, and she has dark chestnut hair that’s pulled back off her face.

  She’s beautiful. She isn’t exotic or worldly looking — not the Francesca or Isabella I was picturing. Instead, she’s beautiful the way your first love is beautiful. She’s the girl next door, the high school sweetheart.

  She’s the girl you marry.

  The thought hits me like a ton of bricks and I have to shake my head. When I look up, she’s staring at me. She’s stopped, maybe ten feet away from my table, and she’s looking at me with such an expression of stricken horror that I almost laugh.

  That is, until she turns around and runs out of the restaurant.

  I mean, she can’t quite run in those heels, but she walks at the fastest clip she can manage.

  I try to get up and go after her but the tables are wedged so close together that I almost crash into the couple seated next to me. I throw out an apology but by the time I get out of the restaurant, she’s gone. I stand out there, surveying the busy street, but she’s nowhere to be seen.

  Somehow my SweetVixen has just vanished.

  I don’t go home right away. Instead I stay and drink the fucking five hundred dollar bottle of wine I ordered. I look around the bar and think about picking up another woman while I’m here, but the truth is, I don’t want another woman.

  I want her.

  Seeing her tonight has only reinforced how much I want her. She isn’t the woman I’ve been picturing, but somehow that makes it even
better. To be perfectly honest, I probably wouldn’t have noticed this woman if I’d seen her on the street. But knowing she’d written those nasty emails … that she’d taken those pictures … it drove me crazy.

  By the time I get home, I’m drunk, pissed, and horny. A triple threat. I flip open my laptop so hard the screen almost snaps off, and then I load up Lovemail.

  I find her messages and search for one that has photo attachments. I find a good one right away — not surprising, when there are so many to choose from. This one is a picture of her leaning over a bed, naked ass facing the camera. I can just make out her pink pussy lips peeking through between her soft thighs.

  My cock is already rock-hard and I’m reaching down with one hand to undo my zipper and unleash it. I grip my dick in my fist and stroke slowly as I look at her picture. It was a hot picture to begin with, and now that I’ve seen the face that goes with it, I like it even more.

  I jerk my cock slowly as I read the message she’d sent with this photo. All about letting me bend her over my desk and take her from behind. Sweet Jesus.

  I can already picture how sweet she’d be, the soft little mewling noises she’d make. My dick throbs in my fist as I stroke it harder, faster. I imagine sliding into her tight pussy, the way she’d feel wrapped around me. So warm. So wet. So tight. So perfect.

  I look at her picture again and imagine smacking those soft cheeks, the way they’d turn bright pink under my palm. The way she’d cry out. The way I’d reach around and thumb her clit. The way she’d clench her pussy around me even tighter.

  My fist is working furiously now and it only takes a couple more strokes before I’m bucking my hips and shooting hot ropes of cum right onto my desk. I’m shocked by how much there is — it seems to just keep coming out of me, wave after wave.

  When it’s over, I expect to feel better but I don’t. I still feel frustrated.

  I don’t want my hand. I want her.

  I pull up our most recent string of correspondence and fire off a message to her before I can change my mind.