The Billionaire’s CamGirl

by Wylder, Penny

  The Billionaire’s CamGirl

  Penny Wylder

  Copyright © 2019 Penny Wylder

  All rights reserved. Except as permitted under the U.S. Copyright Act of 1976, no part of this publication may be reproduced, distributed, or transmitted in any form or by any means without prior written permission of the author.

  This is a work of fiction. Names, places, characters and incidents are either products of the author's imagination or used fictitiously and any resemblance to actual persons, living or dead, or businesses, organizations, or locales, is completely coincidental.

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  Contents

  1. Weaver

  2. Weaver

  3. Weaver

  4. Weaver

  5. Weaver

  6. Weaver

  7. Chris

  8. Weaver

  9. Weaver

  10. Chris

  11. Weaver

  12. Weaver

  13. Chris

  14. Weaver

  15. Chris

  16. Weaver

  Epilogue

  Getting Her Back

  Books By Penny Wylder

  1

  Weaver

  Take down the straps of that camisole. I want to see them hanging down your shoulders.

  The text appears in the bubble at the corner of the Sugar Girl website. It always amuses me, the things that turn a guy on. Wear this color, not that color. Put your hair in a high ponytail; now whip it around. Touch yourself, very, very slowly. Slower. Sometimes I feel more like a sociologist studying human sexuality than a cam-girl climbing her way out of debt.

  It’s been four months of steady work on the Sugar Girl platform. After a year of waitressing jobs and the high cost of living in New York City, I’d decided to take the bull by the horns and start making some serious money. In college I’d had dreams of starting my own business, opening up a hip youth hostel, nothing too ambitious, just a sweet spot with a dozen rooms for bargain conscious tourists in Brooklyn. My business plan had been my culminating project in hospitality school, but after I graduated, I realized how completely naïve I had been. Despite putting in long hours at a SoHo hotel’s trendiest restaurant, contributing to its new (and successful, I might add) marketing campaign which went beyond my job description, it was clear I had no future there. I wouldn’t be moving up that corporate ladder. Unfortunately, I came to that conclusion after I was thousands of dollars in debt and on the verge of homelessness. Sure, I could have been thriftier. I was on my own for the first time and I did spend beyond my means, but mostly it was the high cost of city living and the awful pay from the restaurant that did me in. Oh, and the manager’s insistence that he get a cut of our tips.

  So, when my lease was up, and the landlord had no intention of renewing it, I’d moved all my boxes into my mom’s basement. My mom wouldn’t have minded if I’d moved back in, but I knew she was barely able to keep on the lights herself, and I didn’t want to add my own financial issues to her stress. After all, part of my motivation is to help her, and I knew I couldn’t do it from my old childhood bedroom, eating her groceries, and most likely falling into the old habits of my teenage years. I decided I needed a plan. A plan to make money and make money quick. I wasn’t going to find another shitty apartment I could barely afford and hop from restaurant to bar suffering customers’ abuse to barely scrape by; I’d work my ass off for a year, pay down my debts, save, and then put my business plan in motion. It turned out the most effective way to earn lots of money quick was working my ass off by using my ass. And my tits. And my Oh baby, yes baby, right there baby face. Bonus: I didn’t even have to get out of bed to do it.

  I applied to be a cam-girl on the most popular and lucrative webcam site on the internet, Sugar Girl. They only accept about five percent of applicants, so I was thrilled when they put me on their roster. It felt a little weird at first, accepting that this was who I’d be for a while. I mean, no little girl dreams about taking her clothes off for total strangers when she grows up, much less doing the things that I’ve been doing over the past few months. But I was backed into a corner and I had no choice but to take care of myself.

  Take it off now. Pinch your nipples.

  WildCaptain types. He’s been my client since day one. In fact, he’s my only client now. The first night I had access to my webcam page was pretty bizarre. After I moved out of my apartment and quit my job, I took a last-minute trip to Paris. It was mostly to support the opening of my best friend’s restaurant, but it was also my last hurrah before getting to hard work for a solid year. When I returned to New York and landed at JFK airport, I had no place to go, so I checked into a dirt-cheap room in a pretty unsavory motel. Everything I owned was in my mother’s house except for my bags from Paris and my laptop. I didn’t want to waste any time, so once my account was live, I thought, no time like the present. I tried my best to set the stage in the squalid room. I hung a scarf over the busted-up headboard and stripped the bed of its disgusting and tacky bedspread so I’d be displayed on the crisp(ish) white linens. I drank half a bottle of wine because, let’s face it, I needed a little bit of liquid courage, and I logged on. And I waited. And waited.

  I must have dozed off because an hour or so later I heard a ping. I checked my browser window and saw a message from WildCaptain.

  Are you available?

  And that was the beginning. It certainly helped that I was jetlagged and half-drunk that night. The exhaustion and wine quieted my nerves, and my first session went better than I expected. It also helped—a lot– that I’d just come back from Paris where I’d had the most mind-blowing one-night stand of my life. It was easy to take off my top, to touch myself, because I imagined the man behind the screen was Chris, a sexy stranger who’d fucked me senseless just nights before. WildCaptain was my steady client for the entire week, and the money I made from his sessions and tips alone allowed me to rent a bedroom in a friend’s apartment.

  The next week WildCaptain made me an offer I couldn’t refuse. He wanted an exclusive. After a few back and forth emails with Sugar Girl, I learned that this wasn’t entirely creepy. Some guys liked the idea of having their own personal performer, and they were usually guys who could afford to pay. Sugar Girl advised me to take it, and I was able to set my own price for the private arrangement. And if ever things got weird, Sugar Girl would block him. In exchange for a hefty fee, my profile was made private to assure him that I really was his and his alone.

  So here I am. Playing with my nipples on my bed, my laptop in front of me, no longer in a friend’s extra room but in a swank apartment of my own. And it isn’t creepy. In fact, it’s a turn on. I feel free with my body and comfortable with the stranger behind those dialogue bubbles. As I rub my nipples, feeling them harden into peaks under my fingertips, I can feel my panties getting wet, and watch my computer screen, waiting and hoping for him to tell me to touch myself.

  How does that feel?

  “I feel this all through my body,” I say to the computer. I’d always imagined I’d use some sort of weird “sexy” voice, but there isn’t any need to act. I use my regular voice with WildCaptain, and it seems to do the trick. It’s clear what he thinks is sexy is watching me, the real me, following his commands, getting worked up, making the noises that I naturally make when I’m turned on, coming for him on camera.

  “Tell me what you want?” I ask.

  Hand down your panties. Show me how wet you are.

  Those are the magic words, and I so badly wish I could hear them in his own voice. See his mouth forming the filthy words that turn me on. I slide my hands from my breasts down my tummy and under my panties. I slide two fingers up and down my seam, gathering the moisture poo
ling there, and also taking a few sneaky passes over my clit, screaming for attention.

  I said show me.

  He can get bossy sometimes. I pull my hands out from my panties, pressing my fingertips together, and then pulling them apart, showing him the string of fluid stretching between. I wish I could hear his reaction.

  Rub your wet fingers over your nipple.

  I rub the moisture on my nipple, and it tingles in the cool air. I snake my other hand back to my pussy, even though I don’t have permission.

  “I wish I could hear your voice,” I say. “I wish I could see you pumping your hard cock.”

  Trust me, I don’t look as good as you. Take off your panties.

  I feel goosebumps rise on my skin and I know we’re getting into the homestretch. Sure, the client’s pleasure is what this is all about, but after the first couple of weeks chatting with WildCaptain, I haven’t ever ended a session without coming. Before we had our exclusive agreement, I took a few other calls from random guys, and each of those sessions ended in minutes. They were thrifty and fast. As soon as they came, they’d disconnect. In fact, I hardly had to do more than take off my bra and reach into my panties before click, the session ended without even a goodbye. This arrangement with WildCaptain isn’t only a money-maker, it’s fun, too.

  I wriggle out of my panties and throw them off the bed, out of range of my laptop’s camera. They land neatly on a potted plant and I giggle. The left side of my bedroom, where the Captain’s eyes could never venture, is a total mess. For months now I’ve pushed everything off my bed onto the floor there.

  What’s so funny? I saw that little smirk.

  “It would ruin the fantasy if I told you,” I say. “Trust me. You don’t want to know about the mess off screen.”

  Do you want to know about the mess I’m about to make on my fist? You look so fucking hot. I could stroke myself for hours looking at your tight body. Lay down now. I want to watch you come.

  I recline on my bed and brush two fingers over my clit. It feels hot and swollen and so ready for attention. I turn my head so I’m staring directly at the camera.

  “I could go for hours too,” I say. “Want to play a little game and see who can last longest?”

  I wish, but I have a plane to catch in a half hour.

  It always seems like he’s flying off someplace. I don’t know what he does for a living, but I know he makes buckets of money and travels most days of the week.

  I’ve been rubbing my clit leisurely, every few seconds dipping my finger into my pussy and sweeping back up. The rhythm is so good, and I can feel my orgasm building. My toes are curling in my sheets and my knees are now splayed to the side. As my fingers speed up and warmth creeps up my spine, I know it won’t be much longer before I come.

  Tell me what you’re thinking.

  “I’m thinking about you, with your thick cock in your hand. I’m imagining tracing my tongue over it and tasting you. The sounds you’d make. I want to feel…” I can’t go on. My words devolve into moans and pants as my hand works faster between my legs. And I am imagining him, all those things I’d said. As much as he is my meal ticket and client, he’s also my only sexual outlet, and even though I don’t know what he looks like, all my fantasies and daydreams are attached to him. On and off camera.

  As I touch myself, I think of him sitting in front of his computer, his hand furiously stroking up and over the head of his cock, his feet firmly grounded on the floor as the tension builds in his body. I imagine the strained grunts as he gets closer, his head thrown back and his fist speeding up. As my orgasm starts to black out my vision, I imagine him shooting his cum onto his belly, pumping out the last few strokes of almost painful pleasure. And as I watch him come in my mind’s eye, I let go, my orgasm crashes over me in waves again and again, and a predictable image flashes behind my eyes: it’s the ghost of Chris’s profile, illuminated by the soft blue glow of a computer screen. It’s there for an instant, and then gone. My back arches up off the bed, and I stare at the camera, because if I can’t see him, I want him to see me, to see what he’s doing to me.

  I roll over onto my side, bringing the sheet with me. I’m covered in a light sheen of perspiration, and now that playtime is over, I feel chilly. I stare at the dialogue box, waiting to hear from him. I figure he’s cleaning himself up. I wonder where he is? In a high-rise apartment? The airport lounge bathroom? His fancy office?

  I’ll never get tired of watching you come. I’ve gotta run. I’m cutting it very close—you're a bad influence.

  “Well get going, then,” I say. “Think of me, lying in my bed and drifting off to sleep as you rush through the airport and security last minute. Au revoir.” I blow him a kiss and wave a little goodbye.

  Thanks, Echo. By the way, check your inbox. I’ll see you soon.

  Then he’s logged off and I’m alone again. I pull my laptop closer and click the little mail icon in the corner of the Sugar Girl window. There is a message from Captain. One of over a dozen from the past few months. “For your files” is the subject line and attached to the message is an article about a chain of youth hostels in Europe. Captain knows a little bit about my life, and though I try to keep most details private, I’d let it slip that I’d studied hotel management and dreamed of getting back into that field. As a frequent traveler, he sends me pictures of interesting hotel concepts and articles like this.

  Lately though, I’ve wondered if it’s getting too fun and too personal. He and I have started chatting when I’m fully clothed, and that seems unfair to me. Sugar Girl says as long as he logs in, he’ll be charged, and although I mention this to him several times, he tells me firmly that he isn’t concerned with the charges, and I shouldn’t be either. The first time it happened accidently. I had a horrible cold and instead of declining the session, I accidentally accepted it. I tried to keep to the usual ritual, but after a series of bed quaking sneezes he started recommending different cold remedies to me and we ended up talking for an hour as the pile of tissues grew by my side. After that, it seemed to open the gateway to more frequent contact, and the Candy Girl app made it easy to stay in touch with messaging and emails. So, receiving the article from Captain isn’t unusual, but coupled with my happy post-orgasm feeling and all the fun I had performing for him, I’m starting to hear warning bells about this relationship.

  My privacy is important to me, and no one knows I’m making money this way. It isn’t that I feel ashamed, but I know if my mother found out she’d be beyond devastated. I told her I was working for a travel app and made up some tech sounding mumbo-jumbo. Her eyes glazed over halfway through my bullshit explanation and she hasn’t asked for any details since.

  She worked so hard to put me through college, an opportunity she never had herself. Through my college years, she worked her usual day job as a secretary at an accounting firm, and at night she picked up shifts at her brother’s bar in Brooklyn, taking the train from Long Island into the city at night, and then doing it over again the next morning to her office job. She sacrificed for me, even taking out another mortgage on her house. For my future. I can’t look her in the eye and tell her this is how I’m earning a living, on my back with my tits out. She won’t understand. And I know she struggles to make ends meet, delaying retirement because of the debt she took out for me. I want this for myself but also for her future. If I can just get enough money, I know I can open a successful business and take away some of the financial stress. I told her I was working for a travel app and made up some tech sounding mumbo-jumbo. Her eyes glazed over halfway through my bullshit explanation and she hasn’t asked for any details since.

  This is a temporary situation, I remind myself. With my money from Sugar Girl and Captain’s generous tips, I’ll have enough money saved by the end of the year to start implementing my business plan. But that’s why it’s important to think carefully about getting close to him. Once I save up enough money, I want to leave this chapter of my life behind. As much as I look for
ward to moving on, it’s beginning to sting that I’ll be leaving him behind, too.

  2

  Weaver

  My phone is vibrating under my chin. After my session with Captain, I fell asleep looking through real estate listings in Brooklyn. I’m still thousands of dollars away from buying or leasing a space for my business but looking through available properties is good research and keeps me focused on my future. I look up and toward the window. It’s still dark outside, but I can see dawn out on the horizon.

  I rub my eyes and will them to focus on the incoming text message. It’s from Kate, my best friend and old college roommate. Her restaurant in Paris is having some minor renovations done, and she’s coming to New York to visit. She told me she was traveling to see me, but I know the largest wine and food convention is being hosted in the city that weekend, too. I don’t begrudge her that. In fact, her success inspires me. If Kate can fulfill her dreams, so can I.

  I’ll see you at the airport in two days, bitch!!!! I emailed you my flight info.

  I text back immediately that it’s a plan. I’m so excited to see Kate. These past few months we’ve barely touched base more than a handful of times. Her work schedule is intense, and with a six-hour time difference, it’s nearly impossible to speak on the phone. I feel guilty thinking it, but it is a bit of a relief that we’ve grown distant. The last time I saw Kate at her restaurant opening in Paris, I hadn’t exactly been honest with her about my plans. She knew I’d been struggling, but she didn’t know exactly how badly. When she asked me what I’d been up to, I didn’t want to put a damper on her big night, so I fudged the truth a bit. I didn’t tell her I had no apartment to return to when I got back to New York, and I certainly didn't tell her that I'd maxxed out the last of my credit cards on my plane ticket to Paris. I’d kept the spotlight steadily on her, where it belonged that weekend, and when she asked about work, I told her I was going into business for myself and omitted exactly what type of business I was pursuing.