Her Boss: A Billionaire and Virgin Romance

by Roxeanne Rolling

  “I’ve never had one,” I say.

  Marty chuckles and sips his drink, and his gaze falls back onto his phone.

  “Hot piece of ass, huh?” he says, showing me his phone.

  It’s a model that I happen to already be personally acquainted with, if you want to put it that way. It was a one time thing, as all my relationships are. I like it that way. It’s easy. No mess. No complications. Just an exchange.

  I nod my head stiffly.

  “Damn,” says Marty. “You already slept with her, didn’t you?”

  I shrug. I don’t like to kiss and tell.

  “I can see it in your eyes,” he says, winking at me.

  Marty’s hair is slicked back and his shirt is unbuttoned, showing a tuft of his chest hair. Even though he’s dressed to the nines, he can’t help coming off a bit sleazy, in a way. It’s weird, since he was practically born in restaurants like this, or at least raised in them.

  There’s hardly anyone else in here, since not many people can afford this kind of place.

  A team of waiters arrive and deliver the plates. It turns out a full English breakfast is just some sausages, beans, toast, an egg, tomato slices, and something I can’t identify. I laugh when I see such a “common” breakfast delivered on the ornate plates of the restaurant.

  “So what am I going to do about this whole media disaster?” I say.

  “Just embrace it,” says Marty, digging into his breakfast. “Who cares what people think? All press is good press, right? The Douchebag Billionaire—it has a certain ring to it, don’t you think?”

  I laugh.

  I never have cared what people think of me, anyway. I’ll send the old lady a check for triple the amount of her wheelchair and be done with it. Screw the reporters and everyone else.

  We finish our breakfast and have another couple cups of coffee and a few laughs together. I pay the bill, and we head out. Marty’s off to the beach for the day, to hang out with the slew of models who hover around him whenever he lets them.

  “Come on,” he says. “It’ll be fun. Did I show you the picture of the last time? That one with the red hair?”

  “I’ll pass,” I say.

  I can get women when I want them. I don’t need Marty’s help.

  “Later, then,” he says.

  I get into my Porsche, shift into first, and zoom on out of the parking garage. The Maserati is in the shop, but that’s fine with me. It’s good to get back into the Porsche. It’s a real classic, and it drives like nothing else. Why the hell have I been driving the Maserati for the last week?

  San Francisco is all around me, separated from me just by my tinted windows, my windshield. The engine purrs as I downshift, slowing down as I approach a stoplight.

  I easily classify the people here into groups: the wanna-be hackers, the “made” techies, the “real” San Francisco residents, who resent the techies, the service class… Everyone is divided by their jobs, by their ambitions.

  Me? I’ve got it all, right?

  I’m separate from the rest of them. Money does that to you.

  Lily

  “Any good tips today?” I say as Hailey comes into my room, sighing, and holding her back. She’s wearing her work t-shirt, and her forehead is sweaty, holding her bangs in place.

  “Ugh,” says Hailey, flopping herself down on my floor, sitting with her back against the bare wall. “Don’t ask me about it.”

  “Sorry,” I say, trying to sound sympathetic, but it’s a little hard after my strange day at work.

  “What about your day?” says Hailey. “You get to code like you wanted to?”

  “No,” I say. “I was supposed to be reading this instead.”

  I hold out the thick work binder that I brought home with me, even though I’m pretty sure it’s supposed to stay in the office. After all, it has the words “FOR IN-OFFICE USE ONLY” printed in huge letters on the front.

  “Ugh,” says Hailey. “Looks like your day wasn’t much better than mine. So they’re going to let you code eventually, though?

  “I don’t think so,” I say, explaining a little of what Jim/James told me.

  Hailey’s not too sympathetic, though, which is understandable, considering how back breaking her job can be for so little money.

  “At least you get a good salary,” she says.

  “Yeah,” I say. “But I haven’t told you the craziest thing of all from today.”

  “It’s about a boy?” she says, her eyes taking on that classic Hailey look.

  “How’d you know?” I say.

  “I can just tell. From your tone of voice. Your body language.”

  Shit, I didn’t realize I was giving so much away. I was hoping to avoid telling her that I’m somehow unbearably attracted to this picture of Ryan Hudson. After all, he is the douchebag billionaire, possible one of the most hated men in all of San Francisco.

  “Look,” I say, holding open the binder to the page that shows his photo. “Ryan Hudson is my boss. He owns the whole company. He started it all.”

  Hailey bursts out laughing. “How did you not realize he was your boss? Didn’t they tell you about the company? And you’re like the queen of research. I thought you would have searched the shit out of the company you’re going to work for?”

  “I guess I just didn’t care,” I say. “It seemed like such a boring company… I don’t know. I thought I’d be working for something else. I know I should be thrilled with the money, but now it’s like I won’t even be coding…”

  “Let’s get back to your boss,” says Hailey, sitting up a little, a mischievous twinkle in her eye.

  “Huh?”

  “Well,” says Hailey, her voice turning coy. “He’s pretty hot, isn’t he?”

  “I don’t know,” I say. “I hadn’t really noticed…”

  “Come on,” says Hailey, swatting my leg lightly with a magazine. “Just because you’re a virgin doesn’t mean you can’t find guys sexy or hot.”

  “Shhh,” I say, putting my finger to my lips.

  “They’re not going to hear,” says Hailey, referring to our housemates. “They’re not even here.”

  “Where are they, anyway?” I still don’t think I’ve met half of them.

  “Partying, probably,” says Hailey.

  “They haven’t been here in days, though.”

  Hailey shrugs. “Long parties.”

  “I just don’t want anyone else to know,” I say.

  “It’s nothing to be embarrassed about,” says Hailey. “I mean, we’ve talked about it before, and you know it’s no big deal, either way…”

  “I know, I know,” I say. “I just… it didn’t bother me for a while, but now it’s like I’m not a real adult or something, having never had sex.”

  “Plus you’re missing out on a lot of fun… if it’s good sex, that is.”

  “What makes it good?”

  “You’ll know, trust me.”

  My imagination starts to run wild, and it just so happens that Ryan Hudson is featured prominently in my imagination. But that’s just a wild fantasy. A billionaire and me? That’s completely crazy.

  “We’ve just got to get you laid,” says Hailey. “That’s going to end this whole torment of yours. It’ll make things so much easier.”

  I’m thinking of Ryan Hudson when I say it. I don’t know why I say it. It just comes out: “Let’s do it,” I say.

  Hailey looks at me with surprise. “You serious?” she says. “I thought you wanted to meet the right guy and all that.”

  “Screw that,” I say, this newfound reckless confidence overtaking me in a way I didn’t think possible. All I know is that it somehow has to do with how much I’ve been fantasizing about Ryan Hudson, the douchebag billionaire, and my boss… to the point where I actually broke the rules and took that binder home with me, even though, of course, I can get his pictures online.

  “Wow,” says Hailey. “Are you serious?”

  “Very. Let’s go out tonight and j
ust get it over with. I don’t care if it’s good or not. I just want to get it done once and for all.”

  But as I’m saying this, I’m already getting cold feet.

  What, I’m going to just march into some bar, walk up to a guy, and tell him to take my virginity? Or maybe I shouldn’t tell him at all. Maybe it would freak him out.

  “Don’t worry about it,” says Hailey, reading my anxiety correctly on my face. “It’s going to be fine. We’ll try to find someone who’s not too much of an asshole. Let’s eat, and then go out tonight. There’s a nice bar that’s not too grody or anything.”

  “I don’t know about this,” I say. “Maybe it’s not such a good idea after all.”

  Hailey sighs. “You’ve been talking about this for so long,” she says. “How it’s interfering with your life and everything, how you don’t feel like a real adult. I think you’re right, I think it’s time to just get it over with. Then you can move on to dating and real relationships and all that stuff.”

  “But I never pictured it like this,” I say.

  “We haven’t even gone to the bar yet,” she says. “You’re not in some guy’s bed yet.”

  “But you know what I mean. I just thought… I don’t know, I’d be in a relationship or something.”

  “At this point, your virginity is just holding you back from actually dating anyone. And you have to do that to get into a relationship.”

  “You’re right,” I say. “Fine, let’s do it.”

  “Great!” says Hailey. “You hardly ever come out with me. This’ll be fun! A girl’s night out. And don’t worry, I’ll keep an eye on you, and help you choose the guy.”

  “You think it’s going to be that easy?” I say. “I mean, maybe we should just concentrate on having fun, and see what happens. I mean, how do we know someone’s just going to want to… have sex with me like that?”

  Hailey looks me up and down and scoffs.

  “You’re gorgeous,” she says. “Guys are going to be drooling all over you. You see? You haven’t been out in such a long time… too long.”

  I blush a little. I’ve never been super confident in my appearance, especially now that I’m starting to um, blossom, like this, with all my curves growing bigger.

  “I don’t know,” I say again.

  “We’re going,” says Hailey, putting a note of finality in the conversation.

  She heads back to her room, and I swallow hard, gulping. There’s a cold feeling of nervousness and anxiety in my stomach. What have I gotten myself into? I’m not ready for this.

  To take my mind off things, I open up some computer code that I’ve been working on, just as an exercise for myself, and I let my mind sink deep into the C++ code, letting the algorithms, loops, and variables overtake me. Hey, it’s a way to get my mind off potentially losing my virginity to some idiot stranger.

  Ryan

  I’m back in my Mission District house, in my personal gym.

  I’ve stripped off my shirt, and I’m wearing short gym shorts that go about halfway down my thighs, to give me more movement when working out.

  My home gym has a treadmill which I hardly use, but it’s also got a complete set of free weights. When I started getting into weight lifting, I used the machines, because that’s what I saw everyone else at the gym doing. But I soon found the freedom and toughness I was looking for, that real grit, in free weights.

  I’ve got a top of the line squat rack and a separate bench press bench. Lately, I’ve been getting into Olympic lifts, though, and I have a complete set of everything. I’m not messing around with this, the way other rich guys do. They spend a half hour on the treadmill and call it a day—they did their duty for the doctor. Me, this is the one place where my life isn’t easy anymore. And I long for that struggle. That’s what I love about weight lifting—it’s just me against the metal, against the weight that never changes no matter how much I’ve got in the bank. I can either lift it or I can’t.

  I squat down, gripping the cold steel bar beneath me. I rotate my hands to a classic grip, letting the texture of the metal bite into my flesh a little. It’s good to have callouses. It’s good to feel a little discomfort, even pain. It keeps things real.

  With perfect form, watching my body in the mirror, I quickly pull the weight up to my stomach and then over my head, holding it up, executing the clean and jerk perfectly. I step back and throw the 200 pounds down on the ground. This is just a warm up, but I’ll work up to my max.

  An hour goes by, my mind completely clear, completely lost in the weights. The house is silent.

  When I’m done, I head into the kitchen in my gym shorts and pour myself a glass of organic milk from the refrigerator.

  I pull down my gym shorts, just because I can, and walk to the shower buck naked, my cock hanging before me like a pendulum.

  With the hot water showering down on me, my cock starts to grow, as if on its own accord. I let my hand brush against it, and can’t help but gripping it in my fist.

  But why not settle for the real thing?

  I make a snap decision. The same one I’ve made a thousand times before. It’s not like I have a job to go to.

  I’m going to hit the bars, pick up a hot piece of ass, and lay her down naked on my bed. Or, if I’m in the mood for something quicker, maybe we’ll fuck in the bathroom. I’ve been known to do worse.

  In another twenty minutes, it’s dark outside, and I’m dressed, seated in my Porsche bucket seat, and roaring out onto the road.

  The bar is called Bow Tie, a semi upscale place where people hang out, sipping martinis and trying to act richer than they actually are. It’s a hell of a lot different than the dive bars I used to hang out in when I was just getting my start, working on my algorithm.

  There’s not much action yet in the bar. A couple women give me glances, and while they’re quite attractive, wearing low cut dresses that hug their bodies, there’s just not that special spark there. I need that. I long for that, and crave it. That moment of connection, however brief. That’s what does it for me. Well, that and a banging body.

  I sip a glass of whiskey and chat with the bartender while I wait for the place to fill up.

  “It’s been a while since you’ve been around here,” he says while wiping down the bar, as bartenders always seem to do. (I think it appears more professional if they’re always doing something, rather than just standing there.)

  “You know how it is,” I say vaguely.

  “A lot of work, huh?”

  “Not exactly,” I say. “I spent some time down in the Bahamas, but it got boring.”

  “Sounds like a problem I’d like to have,” he says, giving me a grin.

  “Not a lot of action here, tonight?” I say.

  He shrugs. “Maybe not tonight. It’s a Tuesday, after all.”

  “Tuesday? Really?”

  He gives me a wink and goes to attend to another customer.

  I guess I really am a playboy billionaire, or whatever it is people like to call me. Apparently I don’t even realize what day of the week it is. Not because I’m out of it, or not organized, but simply because the days of the week don’t mean much to me. It’s not like I have to do something different on Tuesdays.

  The bar is a fancy enough place, with an expensive looking bar. Everything has that elegant look to it. I think they renovate it every year, so that it keeps that “fresh” look and never appears dated. That’s what keeps the customers coming back and blowing a sizable portion of their paychecks on a night out.

  As always in San Francisco, there’s a guy next to me on his laptop. I spot some code on his screen, probably Python, judging by the structure of the syntax, even though I can’t see the code because of a little bit of glare on his screen.

  He catches me looking over in his direction.

  “Working on an app,” he says.

  I size him up. He’s one of these typical coder guys you see here. They’re practically swarming the city like insects. When I first ca
me here to run my startup, it wasn’t quite like this. The city was still weirder, stranger, and more interesting. But there’ve been a lot of good changes too. Places like this bar wouldn’t exist, for instance.

  “Startup?” I say.

  He nods his bearded head excitedly and launches into an incredibly boring explanation of exactly what he’s trying to do. He’s a little pudgy, overweight, and already balding, even though he’s in his early twenties.

  He’s got no idea who he’s talking to, obviously, because he’s talking to me like I’m not a coder myself, although frankly he’s doing a horrible job explaining what he’s trying to do. I don’t have the heart to tell him that the central piece of his project has already been done, likely a thousand times better and more efficiently, almost a decade ago. And the surface functions of his app are completely worthless. No one’s going to buy it: a dog walker app. Tells you where you pick up their crap, or something like that, or where the nearest available dumpster is.

  “Sounds interesting,” I say, thinking that I need to get out of here as fast as possible.

  I glance around the bar again. There’s no one who hits me with what I’m looking for.

  Shit, I was looking for something new tonight.

  I grab my phone and start scrolling through my contacts list. There are women listed under names such as “Hot red head from tennis” or “That ass from the gym.”

  Horribly degrading, I know. But how else am I going to have any idea who they are? Like I care if it’s degrading anyway. It’s not like they’re going to see their name. And if they do, that’s their problem, right? They can make of it what they want.

  My thumb flies past at least fifty women who would drop whatever they’re doing, their boyfriends included, for the chance to fuck my brains out tonight. And they wouldn’t expect anything of it. I chuckle when I think of the “douchebag billionaire” term thrown at me. Do people think that bothers me? Now that I’ve got my head on straight, it doesn’t matter one bit to me.