Her Boss: A Billionaire and Virgin Romance

by Roxeanne Rolling

“I want you to… fuck me,” she says.

  “Wait,” I say. “Don’t worry. I’ll give you what you need.”

  I kiss her again on her neck, and move my left hand to cup her breast in my hand.

  She moans, and her neck turns, her head turning back to me. I press my face against hers, devouring her mouth with mine.

  So much for taking it slow. The delicate touch of my mouth now becomes a vicious kiss, my tongue lapping her up. Our tongues are pressed together.

  “I need you,” she says, breaking away from my kiss. Both my hands are on her breasts. Her nipples are rock hard, and I let my fingers trace them, enjoying them, savoring them.

  “What happened to the nervous girl at the bar?” I growl in her ear. “Now you want me.”

  “I wanted you then,” she says. “How did you know I was nervous?”

  “I knew,” I say simply. “What’s your name?”

  “Lily,” she says.

  “You know my name?”

  She nods.

  That’s enough for me.

  Her dress is around her ankles, and I cup her ass cheeks with my palms. She’s wearing skimpy lace underwear that I enjoy for a moment, feeling it under my hands, before yanking it down in one swift motion, exposing her delicious ass.

  I unbuckle my belt, which falls down heavily with a clank. Unzipping my pants with one swift motion, I reach in and free my cock, which is fully erect, ready to burst, just screaming at me for the satisfaction it craves.

  A moment later, a condom is on my cock, and my swollen cock head is pressed against her ass, not quite near her pussy. I relish the sensation for a moment, as I guide her body down towards the bed. She pushes herself down even further, smushing her breasts against the mattress. I gaze down her long, beautiful back, and admire her ass.

  So much for going slow, I tell myself.

  She turns her head to look at me.

  Her lipsticked mouth is pursed, and her eyes shine, and for a moment I regret not letting her go down on me first before fucking her.

  She opens her mouth for a moment, and at first I think she wants my cock in her mouth. Hell, I’d go for that.

  But now it looks like she’s about to say something.

  My body is pressed against her ass. My cock is yearning, swollen and aching beyond anything I’ve ever felt before.

  Nothing comes out of her mouth.

  I pause for a moment.

  “What is it?” I growl.

  “I’ve never…”

  She pauses again.

  “You’ve never what?”

  “I’ve never done this before.”

  “You’ve never done it like this before?” I say, thinking she’s talking about me taking her from behind, which is strange, since as far as I know it’s a common enough sex position.

  “I’ve never had sex before.”

  “You’re a virgin?” I growl back, feeling my lips turn up at the corners. A string of filthy, delicious thoughts fill my head: untamed virgin flesh. She’s going to be tight, fucking tight. I’m going to be the first to conquer her beautiful virgin body.

  “Yes,” she says, barely able to get the words out.

  “I’ll be gentle,” I growl.

  “I think I need to go slow,” she says.

  “That’s fine,” I say, forcing myself to step back away from her. My cock practically screams out when I take it away from where it’s pressed into her ass cheeks.

  I pause for a moment to remove my shirt, my pants, my socks, and my shoes, and now I get onto the bed next to her. She’s still folded over the edge of the bed, her legs looking long as they stretch down to the floor, where her toes barely connect with the ground.

  I turn next to her, facing her head. Her hair is hanging loosely over one eye, and she looks up at me, her eyes seemingly filled with something… something I can’t quite capture.

  “I can’t do it,” she says.

  “I’ll be gentle,” I say.

  “I can’t… it’s just too much. I don’t even know you.”

  I shrug.

  “That’s fine,” I say.

  My cock is positively aching. It’s still rock hard.

  But she’s made up her mind.

  Lily

  Ryan offered to fix me a cup of tea, but I felt so foolish I just needed to get out of there as fast as possible. I got dressed in an awkward silence, and he called me a taxi to take me home.

  “What happened?” says Hailey, as soon as she sees my face.

  I walk right into her room, lean against her wall, and let my body slide down until I’m sitting crouched on the floor, with my head in my hands.

  “I couldn’t do it,” I say.

  “Why? What happened? He found out you’re his employee or something?”

  “I don’t know,” I say slowly.

  At this point in the night, I no longer feel remotely sexy. I don’t feel the way Ryan made me feel for those brief moments, when he so clearly wanted me.

  “It’s the whole virgin thing? Or something else?”

  I nod my head. “A little of everything,” I say. “It’s not like I’m not ready to do it, but… I don’t know. He’s hot…”

  “Smolderingly hot,” adds Hailey, pretending to fan herself.

  “That’s not helping,” I say.

  “Sorry.”

  “And he made me feel things I’ve never felt before… he’s, I don’t know, a real man.”

  “You can say that again.”

  “Hailey,” I say, admonishing her.

  This time she’s quiet.

  “I mean, I’m ready to just get this done with… That’s how I felt earlier tonight. But now, I really want it.”

  “You really want to lose it?” she says. “You mean you want to finally have sex?”

  I nod my head. “It must be incredible,” I say.

  “If he’s good.”

  “And I’m sure Ryan Hudson is extremely good. But he’s just such a dick.”

  “Well it’s not like you’re going to marry him.”

  “It just didn’t feel right,” I say.

  “Well,” says Hailey. “That’s totally within your right. I mean, it’s good you’re sure of your feelings. I’d say you did the right thing.”

  “Really? I thought you were going to give me a stern talking to, telling me that I have to march back over there and let him have his way with me.”

  “No,” says Hailey, shaking her head. “Nothing like that. I think you did the right thing. Maybe this whole ‘being picked up in a bar’ thing isn’t for you.

  “I’m beginning to think it isn’t,” I say.

  “Don’t worry,” says Hailey. “The right guy will come along. Something will happen.”

  I nod my head, but I’m thinking it won’t ever happen. Why can’t I just be like Hailey, and enjoy myself for once? What the hell is wrong with me?

  “Sorry,” says Hailey as her phone buzzes.

  She picks it up and a grin forms on her face as she reads the text message.

  “Something funny?” I say, thinking that if I hear it, it might cheer me up.

  She shakes her head. “It’s from Dan.”

  Dan’s one of her late night hook ups, a friends with benefits type of situation.

  Nothing could make me feel worse right now. It’s like a slap in the face, exposing my own emotional “problems” or whatever they are.

  Hailey types something on her phone, and then the phone buzzes again as she receives yet another message from Dan.

  This time she giggles and blushes.

  “Sorry,” says Hailey. “But I think I’m going to…”

  “It’s fine,” I say. “You going over to his place?”

  “Yeah,” says Hailey. “But, like, I’ll totally stay if you need someone to talk to.”

  “Don’t worry,” I say. “It’s completely fine. Really.” Of course, it’s not completely fine, but it’s not like I’m going to try to screw up Hailey’s life too.

  �
�You’re the best,” says Hailey. “And it’ll be fine. Don’t worry.”

  Hailey’s still dressed in the skimpy dress that she wore earlier tonight at the bar.

  She gets up, exposing quite a bit of leg, not to mention her breasts, grabs her purse somewhat sheepishly, and is out the door quicker than I could have imagined.

  Now I’m alone.

  In my room, I pull off the dress, which is somewhat wrinkled now after what it’s been through. I carefully hang it up and pull on an old t-shirt and some more normal underwear. I just have one pair of fancy underwear, and I wore that tonight—it’s not like I’m going to sleep in it.

  I turn off the lights and crawl into bed, but I know the moment my head hits the pillow I won’t be able to sleep.

  The night seems to keep replaying before my closed eyes—the luxurious bar, the type I never go to. Then Ryan’s luxury house, where even the garage was nice. Not that I saw much of the house at all, but everything was just super fancy, super expensive looking. Where I live must be like the polar opposite of his place.

  I pick up my pillow and put it over my head, letting my head rest on the bare mattress, somehow thinking that this is going to change my thought pattern, but of course it does nothing. My head is just so full of anxiety and shame right now that nothing helps, not even trying to meditate by paying careful attention to my breathing. I could never get that trick to work anyway—my mind just wanders back to what it was thinking about before. Maybe I’m not doing it right.

  And now I think about Hailey over at Dan’s house, giggling up a storm, having the time of her life on some sexy romp with no strings attached.

  I was so close to having sex with Ryan, and the weird thing is I was so turned on. I can vividly remember how he made me feel, how it felt having his body so close to mine.

  I need to distract myself. I can’t spend all night lying awake having an anxiety attack about how sexually attracted I am to my boss, and how I still couldn’t actually do it.

  There were so many reasons not to, though. I have to remind myself of this, over and over again.

  Oh, crap.

  He’s my boss.

  And yet, he doesn’t have any idea I’m one of his employees.

  That could be wrong.

  The thought that relaxes me is: he never comes to the office.

  Thank God for that, that’s for sure.

  I get up and flick on the light. I’m going to do what I do best: immerse myself in my work.

  But I don’t mean that stupid binder they gave me. If they want to tell me I have to read crap like that all day, then that’s what I’ll do. I won’t touch a compiler at work, but at home I can do what I want, right?

  Once he heard that I was really into coding, my cubicle neighbor gave me a USB drive with the code for the algorithm on it.

  “Everyone has it,” he says. “Don’t worry. It’s not like it’s top secret or anything. It’s actually open, in a sense, but not open-source, because Hudson still has to make money on it.”

  “So that means that if someone finds a problem with it, they could easily write their own algorithm that would directly compete with this one, right?” I asked him.

  “Sure,” he said, chuckling. “But no one can. No one ever has. And that’s because it’s perfect programming. Perfect logic. No one can ever beat it. Ever.”

  Well, I’d still like to take a look at it, I think to myself.

  After all, one of the first things I learned when I started diving into all this is that nothing can ever be perfect. Nothing with computers, that is. People think it’s all math, and that math is all perfect. But actually, it all relies on human logic, and as I saw tonight, human logic can often be faulty.

  I’m up until the early hours of the morning, completely immersed in the files on the USB drive. I have to admit that Ryan Hudson’s programming is perfect. And the algorithm… well, I can’t even begin to wrap my head around it, let alone criticize it. He does things that I’ve never seen done anywhere, things I’ve never even heard of.

  It’s a strange sensation, reading the code written by the man who almost took my virginity tonight. In a way, it’s kind of like reading a book or poem he wrote. Programming, really, is a lot like writing—you have to make things consistent and precise, but they still have to all have important functions. Everything still has to do its job.

  Finally, I cut the lights. I’m more confused than when I started. I thought maybe I’d learn something about the algorithm, but I’m not even sure I found the algorithm. Maybe I’m over my head with all this programming stuff. I’m certainly over my head with casual hook ups, or sex in general.

  Ryan

  I can still taste her on my lips. I can still picture her body lying before me, the gorgeous, perfect curve of her back, her plump ass pressed against my cock… my cock grows partially hard again just remembering the image.

  I’m still sore from yesterday’s workout. I tend to push myself too hard, but that’s just part of my personality. Hell, that’s what’s gotten me as far as it has.

  It’s a weird sensation waking up alone without a “friend” in the bed next to me, ready and eager for a second or third round before I send her home.

  It’s not until my second cup of coffee that I remember what happened before I met the unobtainable virgin goddess last night. My cock swells just remembering her, but I force my thoughts back to the conversation in the bar with that app programmer.

  He was saying there’s a new algorithm out.

  A second later, I’ve got a laptop out, and I’m finding every article I can on it. The code isn’t freely available, but that shouldn’t be a problem. Even though I’m not programming these days, I still have friends who might be able to help me out with that. I need to get this code as soon as possible. If these benchmark speed scores that the articles are reporting are anything close to true, then my company’s in big trouble.

  My entire company is my algorithm. I haven’t been to the office in years.

  I don’t know or care what they do there, so long as there’s an office, and they sell the algorithm to some new companies each year, for enterprise use. But the algorithm basically sells itself. It’s just a website, and people can pay for the use of it. The whole thing is free, but pirating hasn’t been much of a problem, because people find out quick enough that it’s more cost effective to use the algorithm with the proper framework around it, rather than trying to build their own, like scaffolding that keeps falling down no matter how many times you try to put it back up.

  The articles I read say the creator of the new algorithm is a guy named Simmons.

  I’m not panicking, the way some people would. Nothing makes me panic.

  But it’s certainly a serious situation.

  Time to hit the office. Time to meet with the staff, for the first time in years. Many of them I’ve never even met, and I don’t remember the names of the people who were there.

  There was one guy named Jim, or maybe it was James, who’s been programming for years. He helped me with some of the algorithm framework, back when I was getting things set up. A fresh pair of eyes is always good. Maybe he can give me some insights.

  I may be a great coder, but I do know when to ask for help. Programming is usually a collaborative project. I just happen to be good enough at it that I don’t usually need anyone’s help.

  Half an hour later, I’m on the road in my car, wearing a suit, heading towards the office.

  For a moment, I have a flash of amnesia: where’s the office again?

  But I let intuition take me there, driving down once-familiar streets.

  The office building is by itself in a small complex. Now I remember why I stopped coming here—it’s too drab. The whole place just screams: office. There’s never anything fun going on. There aren’t ever any girls. No parties, no fun. Just dull, drab work—the kind of thing I’ve spent my life avoiding at all costs. And now that I can, what’s the point of being rich if you have to come t
o the office all the time?

  I almost turn the car around and head back home. I’ve got enough money, anyway. I don’t really need to keep making money on the algorithm, do I?

  But more money means more fun.

  Plus, there’s a bit of pride. Something that I’ve always felt about my code. I can’t let it get beat. I just can’t.

  The interior of the office is nice, if a little dated. Nothing flashy, just a normal high class office.

  “Can I help you?” says the secretary, a woman on a swivel chair behind a huge desk.

  I wonder what she does all day.

  How does this office even function for years unattended like this?

  “I need to speak to a programmer here,” I say. “I think his name is Jim, or maybe James… or maybe Jerry. Older guy… he’s been programming for years.”

  “Oh,” she says. “We don’t get many requests like this. Are you interested in using the Sisyphus Algorithm for business applications?”

  I shake my head. “I’m Ryan Hudson.”

  “Oh!” she says, looking like she’s about to fall out of her chair in shock. Her mouth hangs open, and I can almost see the “oh” exclamation hanging comically in the air.

  “I’ll go see if I can find him myself,” I say.

  I walk past her, since she’s still not speaking. That’s not a problem. I always get what I want, regardless of anyone’s reaction. It doesn’t bother me in the least that people are going to be surprised to see me here, or that I haven’t been here in years. But I’m Ryan Hudson. I don’t owe anyone excuses, no matter what. Without me, none of these people would have the cushy jobs they have today

  Heads turn in the office as I walk past rows of cubicles.

  “That’s him,” someone whispers.

  “Who?”

  “Ryan Hudson.”

  “Ryan Hudson!” come the whispered exclamations of surprise.

  There’s a manager here for sure, someone with an office who keeps all these cubicle dwellers in check. I can’t remember their names, or their faces. I’m not interested in speaking with some managerial person now, though. I need a programmer.

  Ah, there he is.

  I can spot his rumpled shirt and slouched back all the way down the row of cubicles. No doubt he’s still got the coffee stains on his shirt. I wonder if it’s the same shirt that he wore when I last saw him.