Taming Cupid

by Emily Bishop

  “Sleep well,” he types.

  Oh my. A little pop up tells me he’s left the chat room, which is convenient. Now I don’t have to sit and wonder why he isn’t saying anything. I’ll have to let Booker know that’s a great feature. I suppress a yawn as I set my phone down. I’m too tired to look at anything else tonight. Instead, I slide into bed, with images of what Master might look like.

  I bet he’s way cuter than Booker Knight.

  Chapter Four

  Booker

  I stare at my phone sitting there on my desk, begging to be checked.

  Has she written anything?

  I’m a complete idiot for caring, of course. I want to tell myself it’s just about the work, the research of the product, but over the past few days, I’ve found that speaking with Angel has become a bit of a highlight to my day.

  She might be the first human connection I’ve ever made. And I’ve never met her.

  I’m not sure it’s possible for me to be any more pathetic. The phone dings, and I nearly jump out of my seat.

  Get it the fuck together, man.

  I lift my phone and open the app. There, beautiful in all its glory, is a fresh message from Angel.

  “Do you ever feel alone even when you’re in a crowd?”

  I wonder where she is. Is she at the theater? A party? It’s a Friday night, so it makes perfect sense that she would be out on the town. Most normal people are. Those people don’t work day in and day out, but they also don’t have a billion dollars.

  I do.

  I tap on the chat box and start typing. “Depends. When one is in a roomful of friends, it can be the most fulfilling experience in the world. When one is surrounded by strangers with no one to talk to, then absolutely. I make it a point not to put myself in the latter situation.”

  “You’re smart,” she writes back.

  I try and imagine what she looks like. With a name like Angel, I can’t help but conjure up an image of a petite blonde, her long hair streaming down her shoulders, clad all in white. Based on our conversations, Angel seems like an innocent woman, a kind woman. She’s not like anyone I’ve ever met, but I realize on some level it’s because she has no idea who I am either. If she knew, would she treat me the same?

  My office door opens. “Are you seriously working on a Friday night?” Kieran plops on my sofa and lifts his eyebrows at me. I set my phone on the desk and cross my arms.

  “Are you seriously questioning my work ethic, after everything we’ve been through?”

  “Yes. Yes, I am.” Kieran grabs a pen from my desk and toys with it. He’s always been fidgety. I learned a while ago how to avoid being affected by his shifty energy, but when I’m tired or annoyed, it’s harder to ignore.

  “Well, I’m a company owner. That’s why. You don’t need any other answer.”

  “Bo, you’ve already made your billion dollars. You know what the point of making money is?”

  “To be able to pay assassins so they can knock off annoying friends?”

  “To enjoy your life, pal.” Kieran leans forward and glances at my computer.

  “You’re not even doing anything important. Let’s go to the bar down the street. Let loose a little. Have some fun. Have a drink near other human beings. Maybe even talk to one!”

  “I don’t bother speaking with other human beings. They are a waste of my time.”

  Except for Angel. For some reason, I can talk with her. Angel is never a burden and always an excitement. This is a new concept for me, and I’m the first to admit I enjoy it.

  Kieran sighs with dramatic flair as he leans deeper into the sofa. “OK, what about this? A good number of your staff like to go to that place for drinks and comradery. Don’t you want to make connections with your team? For heaven’s sake, I’m pretty sure they’re all afraid of you.”

  “Good,” I reply. The last thing I want to do is let loose around my inferiors. How will I get their respect if I’m chugging a beer alongside them?

  “Bo, this is the twenty-first century. People respect a boss who mingles, who wants to engage and be a part of his team. You could lose valuable members if you don’t humanize yourself a bit more.”

  I glare at him. I want him to be wrong, but he sounds terribly convincing. I’m not so archaic that I haven’t read all the major management books. I know what a good manager is supposed to be. Problem is, I didn’t get to where I am today by relying on others. Now that I’ve gotten big enough to need them, perhaps I need to crack open some more of those modern management books.

  “Fine,” I say on an exhale. “But you’re buying.”

  “How fair is that? You’re the rich one.”

  “Ha,” I say. “Come on. Let’s get this over with. Go on ahead. I’ll meet you at the elevator.”

  “Sweet.” Kieran claps his hands together then trots right out of the office. I pick up my phone and open the chat.

  “I imagine you would be impossible not to talk to in a crowded room. I’d make sure you smiled the entire night.”

  It’s a bit of a line, but I’ve opted to be truthful with Angel. I don’t know what’s going to become of this whole thing, but the element of confessing myself anonymously to a stranger helps me open up a little easier. I don’t normally do well talking to other people about anything but business.

  It’s just safer that way.

  I see her typing, so I wait to step out of the office.

  “I’m already smiling because you’re with me. Thank you for that. I don’t feel so alone anymore.”

  I can’t help the grin that spreads across my face at that admission. It feels good to make a woman happy. I’ve never really given myself the chance to. In my life, women are disposable. Usually, they’re after the money or the parties. If they’re hot enough, I allow it.

  For a time.

  Then when I tire of them, I discard them. It’s not complicated. It’s not even emotional. I ensure that each woman understands exactly what she’s getting into, and more often than not, she’s fine with it. It’s been an agreement that’s worked well for me. I get mine. They get theirs. We part ways as indifferent acquaintances.

  No complicated emotions. No baggage. Just sex and money. Just the way life is.

  I type back a quick “good,” then head out the door. If I don’t move soon, Kieran might try to drag me out, and that will end badly for us both. I join him at the elevator and together we make our way down to the main lobby.

  The bar is a few short blocks away. It’s upscale, the booze top-shelf. When we walk in, I recognize a number of familiar faces, but they all turn right toward Kieran.

  “Kieran! Mr. Knight! You guys came out!”

  I think that guy’s name is Rick. Honestly, not 100 percent on that. He writes great code, though. I should make sure I know him. Maybe Kieran isn’t so far off the mark on this one.

  “Hell, yeah, we did!” Kieran holds up his hand and high fives Rick, the two of them jovial as they head to the bar for a drink. My phone dings, and I pull it out of my pocket.

  “There’s something so gross about meeting someone in a bar. All anyone wants by the end of the night is sex.”

  I consider my response carefully. Then I decide to simply go with honesty. “What’s so wrong with that? Sex is fulfilling. It’s necessary for human life to thrive. Don’t tell me you’re not a fan of a good romp.”

  I might be acting a little too forward, but I’ve decided to be myself. Might as well ask the questions I want, say what I want to say. After all, what’s the consequence? The loss of an internet stranger?

  Tragic.

  I glance up and scan the bar. I recognize Lucy chatting up a man in a booth. Across from her, Sasha is sitting on her phone, completely absorbed.

  And she called me a millennial. Ha.

  A new message pops up, and I’m distracted once again.

  “Sex is fulfilling, yes, but when it’s not tied to emotion, when there is no connection, what’s the point?”

  I laugh
before I respond. “The point is it feels good. Clearly, you’ve never had great sex before. I might have to show you the ropes.”

  There is a pause before she responds, and I imagine her blushing, wherever she is. I wonder if the people around her notice I’ve made her blush.

  “And how would you propose to do that, exactly? We still haven’t answered the questions to unveil our pictures. I have no idea who you are, or where you are.”

  “That’s where sexting comes in,” I type.

  “Never tried it. Is it good?”

  I love that I’m her first possible sext partner. Sexting is something I happen to excel at. Dirty talk is one of the funnest parts of intercourse.

  “It’s outstanding. You get to pleasure yourself, so you know exactly how you like it, but you get to imagine the other person doing it to you. It’s often the best of both worlds, perhaps even better than real sex at times.”

  “Are you seriously going to sit on your phone all night now?” Kieran approaches me with a drink in hand, and I take it from him. Whiskey on the rocks, just as I like it. I take a sip and relish in the heat that goes all the way down.

  “Don’t worry about me. Go entertain yourself,” I tell him.

  He rolls his eyes at me. “You are a child,” he says, then walks away. I’m glad he’s gone. I look back at my phone. There’s a message there.

  “I wouldn’t know. I’m actually still a virgin.”

  My dick stirs at the thought. If this woman really is a virgin, untouched by any other man… what I wouldn’t give to teach her what sex can be like. She would never know bad sex a day in her life.

  What a turn-on.

  “There he is! In the corner! Let’s make him talk to us!”

  Kieran speaks to a small group of uncomfortable workers, and I narrow my eyes at him as I stand and make my way for the bathroom. I’m just about there when I bump into someone.

  “Ack! Can people learn how to not walk into people around here…?” When Sasha’s eyes meet mine, they narrow. “Ah, should have known it would be you. Can you stop literally running into me, please?”

  “That’s no way to talk to your boss,” I snip.

  I can tell she’s had a drink or two. Her cheeks are rosy, her hair slightly disheveled. She looks flushed and flustered, though I can only imagine it’s because of my presence outside of work. I generally frazzle women wherever I go. It’s a curse.

  “We’re not at work. In here, you’re not my boss.”

  “Keep believing that and see where it gets you.”

  “Keep running into me and see where it gets you,” she counters.

  Liquid courage. I can’t blame her for that. The truth is, in this back hallway, she smells really good. Hey eyes are bright, her hair luminous in the light of the bar. I’m reaching a point where I can’t hide the fact that I’m attracted to her, and that is a problem.

  “Good night, Miss Ellis.”

  “Good night, Mr. Knight,” she says as she strides past me.

  I watch her retreating backside for only a moment before I pull my phone back out.

  Why hasn’t Angel said anything else?

  Chapter Five

  Sasha

  As I claim a seat on the subway, I hear that telltale sound from my phone, and my stomach erupts with butterflies.

  Master! I didn’t hear from him much after we talked about sexting. I was scared to tell him that I’m a virgin, but then I thought, what the hell? If he’s turned off by that, I don’t want to be with him anyway, and if he isn’t… well.

  Dare I think I’ve met my match? Through an online dating app I’m testing for work? I repress a gleeful laugh at the thought of it. It makes for a perfect story, really, but the truth is there’s no story to tell. Once the pictures are revealed and the fairytale ends, I imagine we’ll go back to living our regular lives, perhaps slightly changed by the experience.

  If I hope for better, I might get my heart broken. Keeping my heart safe was what’s generally kept me a virgin all these years, but it’s also kept me from the agonizing pain of a broken heart. I watched enough of my siblings go through that to want to put myself through it.

  I can be smarter.

  Still, I can’t help but wonder if sexting with Master is a way around all that. It’s personal, of course. Intimate. But it’s not real. The connection may be there, but it’s not at the same time.

  I can’t help but be intrigued.

  I unlock my phone to check my message.

  “Good morning, beautiful Angel. I hope you have a fantastic day.”

  Swoon.

  I tap the screen and reply. “Good morning to you! You have a nice day, and don’t get into too much trouble.”

  “I’m afraid trouble is my middle name. Perhaps I give away too much about my identity by telling you so.”

  I laugh, and an older woman casts an admonishing glance in my direction. I pick up my pace as I stride into my building and press the button for the elevator, still not looking up from my phone.

  “You certainly have. I now know exactly who you are, mystery Master. You’ve given yourself away far too easily.”

  “And here I thought I was being so sly. I’ll have to get better.”

  “Oh, I don’t know,” I text. “You’re doing pretty well so far.”

  “Do you like this app?” he asks.

  I hesitate. I don’t want to tell him I’m only on it to do research for work. Somehow, this thing has turned into so much more. What if he hates me for basically using him as market research? Is that what I’m doing?

  Why do I feel so guilty?

  “I do,” I write back. “I think it’s a unique take on the dating scene. Of course, once the big reveal happens, we might not be so happy.”

  “Why?” he posts back. “Because you think I’ll be ugly?”

  “No,” I write back. “I just think it will be interesting to see how this all pans out. It’s an entirely new experience for me.”

  The elevator doors open, and I drop my phone to my side. If there’s one thing I’ve learned in this office, it’s that I have to pay attention where I’m walking. One never knows when the boss is around to try and knock one down “on accident.”

  Accident my rear. That man has pummeled into me almost every time we’ve crossed paths. Either he’s incredibly clumsy, or he’s out to get me. I tend to think it’s the second one.

  The coast is clear all the way to my office. I unlock the door and step inside, relishing my own private space. When I sit down and pull my phone back up, Master’s response is waiting for me.

  “Are you ready to try some of the questions? That way, you can reveal a little more of my picture. We really get to test our trust today.”

  A fluttering of nerves shimmers across my skin as I consider it. That’s the whole point of the app, right? To get to the end? To see if one can connect on a physical level after doing so on an emotional level? I can’t very well say I’ve researched the app if I only go in halfway.

  “Let’s do it,” I type, and I hold my breath as he prepares a question for me to answer. When it appears, I hold my breath.

  “What was your childhood like?”

  I grin. That’s a bit of a softball question. I type in my response.

  “Normal. I’m one of six siblings from a small town in Pennsylvania. My parents love each other, even now, and generally, I led a pretty sheltered life. My siblings were my best friends, and we spent most of our time playing together. I befriended a few children outside of that, but I was OK with what we had. It was nice.”

  When I press send, the app gives me the option to write my own question for him. I type in a question, then press send.

  “What do you do for a living?”

  It’s innocent enough. I probably could have gotten more in-depth. Do I really want to ask about politics, religion? What his views on having children are? What if I don’t like the answer, and the bubble is popped?

  No. I want to keep things a little more
simple, for now at least. His response comes in. I glance up at my door, but no one walks by. I feel a little guilty playing with Master on a dating app at my work, but I remind myself that this is part of the work. I’m simply researching. That’s all.

  “I run my own company. I work in the technology field.”

  The answer is short, and it tells me little to nothing. Still, I watch as the blur on his image clears up ever so slightly. Not enough for me to discern any features, but it’s one step closer to finding out who Master is.

  I can’t help but be a little curious, after all the talking we’ve done. His second question pops up, and I read it.

  “If I were to ask you to sext with me through this platform, would you do it?”

  I should be creeped out by that question. I’m almost a little ashamed of myself for not feeling exactly that. Instead, I’m intrigued. He’s piqued my interest in that arena. Who better to practice it with than a self-proclaimed expert?

  Not that I would know any better anyway. I consider my answer.

  “I would, under the condition that you explain to me the ground rules, and I can opt out at any time I feel uncomfortable.”

  I don’t get a chance to see his reply, because the box to ask my own question comes up. I inhale, and take a plunge, feeling brave.

  “What would you do to me, if I were with you right now?”

  My heart beats a little faster as I wait for his reply. When it arrives, I hold my breath as I read.

  “First, I would make sure you’re comfortable and make myself aware of any ground rules you may have. Then I would slide your panties down your legs and toss them on the floor before lifting you up onto my desk. I’d pull your legs wide apart, open you up to me, and I would slide one finger down the center of your body, stopping right at your tight little virgin entrance. I would start slowly. First, I’d insert my pinky, then switch out each of my fingers until I was certain you could stretch out enough to accept my dick in your pussy. Before I’d take you, I would lick you, inside and around, all over your box, until your legs were shaking with need. Only then would I slide into you, and fuck you on my desk.”

  I can hardly breathe, reading that. My vagina tingles at his words, and he’s so graphic I can nearly feel what he’s described as I read.