Chapter Text
It was a typical Monday afternoon. Penelope was sitting at her desk about to ask her boss for a raise. She had been working for Mr. Colin Bridgerton for the last four years and recently she took the position as his assistant when his previous assistant left to go on maternity leave for the next few months.
It has taken Penelope a lot of courage to get to this point—asking for a better salary. It was only last week that she got a letter from her landlady letting her know that her rent was past due. She was only 300 dollars short on her last paycheck and after informing—Beatrice—her landlady, of her situation, Penelope was then given a warning and told to have it next time or she’d risk getting kicked out.
She wasn’t sure how she was going to pay that and eat too. Her fridge was nearly empty.
She let out a long sigh and stood from her desk. It just so happened that her desk was right outside her boss’s office, she could see him on the phone.
Maybe this isn’t a good time?
No…
Just try.
Penelope walked into his office after knocking on his door and seeing him nudge his head—motioning for her to enter.
“I know this, Fife, get last week’s budget report on my desk on Wednesday.” He snipped into the receiver, “And don’t waste my time,” after that, he hung up his phone and leaned back in his chair, directing his attention to her. “Pen, is there something you need?”
Back out now.
“No…I mean yes—I mean–”
He raised a brow. “Well? Which is it?”
Penelope took a deep breath and quickly replied, “Yes. I um… I was going to ask if it were possible that I could… get a raise? I’ve just been working here for a long time and this position has broadened my skills but I need—”
“No.” Colin said dryly.
“But-”
“Is that all?”
And he’s not evening going to say why? Bastard.
“Yes.”
“Close my door on your way out.”
That evening, Penelope found herself sipping a margarita with her two friends, Rae and Gen, who were in the middle of a conversation about their work day.
“I had this guy come in asking for one singular rose. He was handsome.” Rae announced, sipping from her glass.
Gen chuckled and slowly shook her head. “Yeah, that one rose was probably for his partner.”
“And while I think that’s actually so beautiful, it wasn’t like I was flirting—just admiring.”
Gen rolled her eyes and glanced towards Penelope. “Penelope, how was work? You look defeated.”
“I am defeated.” Penelope replied, shoving her half-empty glass away and sitting back in her seat. “I asked for a raise and my bastard boss told me no without an explanation. I mean I thought the company was doing good. I was short 300 dollars on my last check and my landlady gave me a warning.”
“What a jerk.” Rae remarked, tapping her fingers against the table.
“Why don’t you try to find a side gig? You know something that will cover that 300 and then maybe a little extra cash to do what you want?”
A side gig…?
“I don’t know if—”
“Oh my god.” Rae said suddenly, causing them both to look at her in surprise.
“What?” Penelope blinked.
“Listen, my sister’s friend has a side gig, I could give you her number! She could probably help you start right away.”
“What? Really?” Penelope leaned forward, raising one brow in curiosity. “What is it?”
“Okay… it might be a little out of your comfort zone but… what about doing spicy videos?”
“Spicy videos?”
“Yeah, It’s a whole website, I forgot the name but I’ll ask Harper. And there’s memberships for your monthly subscribers and you get paid instantly depending on subscriptions.”
She assumed Harper was Rae’s sister’s friend.
“I don’t know if that’s something I can do… Rae.” Penelope shook her head and shrugged, “I mean… would anyone actually find me attractive? And I feel like that requires confidence I don’t have…”
Rae gave her a knowing grin and tilted her head to the side. “Well, I believe you’re beautiful. I think you’d make bank. It would definitely teach you to be more comfortable in your skin and you can set your own schedule too. Just… think about it okay? I’ll still send you Harper’s number.”
“Okay…” Penelope fidgeted with the sequence on her dress. “I’ll think about it.”
“Good.”
Gen placed her hand on Penelope’s shoulder. “It’ll be okay, and she’s one-hundred percent correct—you are fucking beautiful.”
Heat found Penelope’s cheeks and she shoved a strand of hair behind her ear. “Thank you.”
They all raised their glasses for a toast to Penelope’s success.
The following work day, Penelope was in another meeting, she grabbed her notebook and flipped it open and jotted down some notes.
Then her mind wandered to what Rae had said. When she had gotten home the previous night, Rae sent her Harper’s number just like she said she would and she saved it to her contacts.
Nerves pooled her stomach. What would she even have to do? Strip tease? She didn’t even have a proper camera—but her laptop camera might work for now. Was she actually considering this?
“Miss Featherington.”
Colin’s voice pulled her from her thoughts. She looked up from her notebook. “Yes, sir?”
“Did you write down the last of what I said?”
Penelope looked down at her notes but—she wasn’t sure if that was everything; she zoned out and—
“I’ll take that as a no.” Colin looked around the room, before stating in a firm voice, “please make sure you all are paying attention, I’m not going to waste my time if none of you have the attention span.” He turned and continued his speech on product development.
Bastard.
Penelope’s cheeks burned with embarrassment. She pushed her fingers through her hair and sighed. She tried not letting what he said get to her. She knew Colin wasn’t a fan of crying or emotions because it was clear that he didn’t have feelings or emotions or—a soul. She wasn’t going to let him win.
After work, Penelope got ready for the night and laid out on her bed, staring at the ceiling. How was she going to deal with this for the next few months? Her boss was a grade A asshole, arrogant and ignorant and rude and—
Her phone buzzed next to her on the bed.
She picked it up and looked at the screen.
BOSSY BASTARD: We have a super early meeting at 6AM. It was decided at the last minute. Don’t be late.
Penelope: 👌
BOSSY BASTARD: Stop with the emojis.
She rolled her eyes and tossed her phone on the other end of the bed.
Right after she took the assistant position. Colin and her exchanged numbers for work related things. So he could contact her directly if needed. He said it was required.
So, Penelope gave him the perfect contact name.
She got the job right out of College. She was a sales associate for the last four years until three weeks ago—she volunteered to be his assistant, and thought there was going to be some sort of increase in her salary. She was wrong.
Penelope glanced over at the living room table. She noticed a few papers scattered on top. Her bills. God, so many bills. She only had a few weeks left to pay what she owes on rent in addition to next month's rent.
She was drowning in debt too.
Then it hit her like a thunderbolt from the sky.
The side gig.
The one Rae told her about. She had Harper’s number.
Penelope sat up, grabbed her phone and sent Harper a text.
Penelope: Rae mentioned your side gig.
Why was she so nervous? She was shaking. She could see her thumbs shaking over her phone keyboard.
A few seconds later, her phone buzzed in her hand.
Harper: Sure thing! You’re Penelope, right? She filled me in a little about your situation. I can explain the gist of it and send you the link for the website if you’d like?
This was it.
Do it.
Penelope: That’s me. I’ve never done this before so that would be helpful. Thank you.
Harper: That’s perfectly fine! Everyone starts somewhere. So, first things first, the website is legit. It’s for women to post only. And of course you’ll have customers.
Penelope: Customers?
Harper: Yes. So, first you create your page, and set up your prices. There’s a Standard subscription and a Premium subscription and you have to post a preview (one time free-30 second video post) to get started. The standard is what men pay to be able to access basic content—like one-to-three minute videos or just pictures that you choose to post. The premium content ranges between videos to pictures to personal requests and direct messaging. It’s all on the website.
Penelope: So I can set my own pricing and limit what I want to post? On my own terms?
Harper: You can only limit what you want to post for standard pricing. Like what’s restricted unless your customers upgrade to premium. Premium is an open-concept. If a premium customer wants you to do something specific they’ll send you the money and it’ll stay on hold until you accept or reject their request. After you complete the request, it’ll approve and pay you instantly. Premium customers can also request via DM which means they can keep sending you money and ask you directly what they want instead of you just getting the request once in your inbox. Pricing for both subscriptions is up to you—only there’s a pricing limit. Standard is from 5 to 50 dollars and Premium is 55 to 200 dollars, you can set your price within that range. Standard payment is every month and Premium is every month and instantly per request. The free video post is the 30 second preview/introduction to your page. It’s going to get people to subscribe for more.
Penelope: Sounds intriguing.
Harper: Really?
Penelope: No, I'm nervous.
Harper: Haha. Nothing to be nervous about. You’re in control. This is your page.
Harper: Any questions?
Penelope: What if I get asked to do something that’s uncomfortable for me?
Harper: Then you can refuse the request. You don’t have to accept a request. And if you feel uncomfortable with certain people then you can block or report them. The company is pretty good about creating a safe environment for you.
That’s a relief.
After a few minutes of consideration, Penelope typed out a response.
Fuck it.
Penelope: Okay. I’m in.
Harper: Perf. *Hyperlink* Sign up and let me know if you need anything else.
Penelope: Thank you!
Penelope clicked the link and it took her to the website.
Whistledown’s Ladies?
That’s the name of the website?
She tapped the sign up button and filled out her information.
It brought her to the Subscription pricing section.
Premium and Standard.
She thought about it for a moment and typed out a price for both.
Premium: 150$/month/per requests
Standard: 25$/month
That’ll do.
She was going to need those Premium subscription requests like she needed air to breathe. But was she willing to do what they asked? She’d have to be careful not to show her face and angle her computer screen just right but—there’s no way she could afford not to.
After she finished adding her bank info and setting up her profile, her username, PFeathers96 was the only thing she could think of. It’ll have to be good enough. She tapped save.
Now, for her first post. It was a free post. The preview to attract customers.
What should she do? Show her shoulder? Bite her lip seductively? God, how the fuck was she going to do this? Was she even capable of being sexy?
Penelope closed her eyes and took a deep breath. Once she felt her nerves fade away, she tapped her screen off and tossed her phone then grabbed her laptop from her work bag and set it on her lap. She signed back into the website and clicked Add a new post.
Just do what feels natural.
Penelope placed the laptop on the bed in front of her and angled the camera down so it didn’t show her eyes. She clicked record for a thirty-second video and slowly unbuttoned her silk pajama top—not fully removing it or revealing her breasts—and teasingly bit into her lower lip, then she slowly lowered one of her hands down to the band of her matching silk pajama shorts, just when her fingertips dipped below the fabric, the video stopped.
She rewatched the video, one time. Two times. Three times. Are people going to find this sexy? Was she going to have to start looking for a sturdy box to sleep in?
She hadn’t gotten laid in a long time, which meant she was touch-starved and horny. She’d touch herself at night occasionally and that came like second nature—but this was different. She was going to be watched over and over and over again.
But, she was getting paid. People were going to have to pay to see her content.
It’ll be okay just tap the post button.
See what happens.
Probably nothing. Maybe this was all going to be for nothing and—
No.
Stop that.
It’s not a waste. Just try.
Penelope took another deep breath and then quickly tapped the post button.
Gah! She did it! Penelope closed her laptop and fell back against her pillows.
She leaned over and grabbed her phone then texted Harper.
Penelope: Just finished the sign up process and uploaded the preview video.
Harper: That’s fantastic! You’ll get customers in no time, I’m sure. For now, get some rest. :)
Penelope: Will do. Thanks again.
Harper: Of course! Good night!
It wasn’t too long after that conversation that she drifted off into a deep sleep.
The sun shining in her face woke her. She peeked her eyes open and looked around her tiny one bedroom apartment. Why didn’t her alarm go off?
She sat up and pushed her finger through her hair when she glanced next to her to find her phone. She tapped the screen but it didn’t turn on. Her phone was dead and—-
Wait.
What time is it?
She opened her laptop and it was 9:34AM.
Fuck.
She was very late. Three and a half hours late. Fired. She was going to get fired.
She scrambled out of bed and hurriedly got dressed and brushed and tied her hair up in a ponytail. She slipped on her shoes and packed her laptop and phone in her work bag, and ran out the door.
She managed to haul a cab and paid the driver what was left in her wallet when she arrived. She got to the elevator and took it to the 23rd floor to their office.
As she exited the elevator, she wasn’t paying attention and ran into a wall or—something hard like a wall.
Wait.
She looked up and met eyes with her boss. Who looked furious. Because of course he was.
He grabbed her hand and led her to his office. He slammed the door behind them and turned to look at her. “Do you ever do what you’re told? I told you to not be late.”
“I’m sorry I—“
“Do you take this job seriously, Pen? Or is this some kind of way to pass the time?” He crossed his arms over his chest and shook his head. “This isn’t how an assistant is supposed to handle things.”
Penelope clenched her fist. “I know it looks bad but I—“
“Give me one reason why I shouldn’t fire you.”
She couldn’t. God, she really couldn’t. He was insufferable.
“I tried to get here but my alarm didn’t go off because my phone died and you haven’t been making my life any fucking easier so what do you expect me to do? My world doesn’t revolve around you.”
Fuck.
She shouldn’t have said that.
“Excuse me?” He arched his brow and then he walked over to her. She dropped her bag to the floor when her lower back met the edge of his desk and he was towering over her like a giant tree. “Would you like to repeat that?”
Well, might as well just say how she’s been feeling—especially if he’s going to fire her anyway.
“I said… my world doesn’t revolve around you. If you want to fire me, fine. But, good luck finding someone else who will put up with your attitude.”
They stayed in silence until Colin clicked his tongue, averted his cold stare and stepped away. “Don’t let it happen again.”
Huh?
“What?”
“Pen, don’t make me repeat myself, just go get settled and get ready for our next meeting in ten minutes.”
She blinked at him as he sat down in his chair and opened his laptop.
“Why are you still standing there?” He asked firmly. “Close my door on your way out.”
Penelope grabbed her bag and left his office.
She sat down at her desk and stared into space while she registered what just happened.
What the fuck was that?
A few moments later, she grabs her phone out of her bag and plugs it with an extra charger she keeps in her desk.
Then she remembers what she did last night.
Penelope hadn’t checked yet to see if she had any new subscribers. She’ll have to check later.
After the next meeting, she sits back down at her desk and turns on her phone.
Once it powers on to her Home Screen—notifications pop up.
2 missed calls.
5 new messages.
She tapped the text message notifications.
BOSSY BASTARD: I thought I told you not to be late. Why aren’t you here? It’s starting now.
BOSSY BASTARD: This is incredibly unprofessional and I am very disappointed.
BOSSY BASTARD: Was this your way of quitting? No call, No show?
BOSSY BASTARD: Pen. Answer my call.
BOSSY BASTARD: Please.
That last text was the first time she’d ever seen this man use the word please. In any context.
What a strange man.
After a long day of catching up on paperwork and scheduling meetings for the rest of the week, Penelope made it home. She grabbed her laptop and her phone from her work bag then tossed the bag on the floor next to her bed. She climbed in under the covers and opened her laptop.
She signed into her page and clicked her notifications icon in the top right corner.
10 new standard subscribers.
1 new premium subscriber.
Woah.
No fucking way.
It worked.
What does she do now? Post something for her standard customers? Wait for a request for the premium request?
Penelope pushed her laptop off her lap and got out of bed. She needs to.
She remembered what Harper told her about how she was in control.
She let out a sigh and relaxed her shoulders.
Okay, first, shower then find something sexy to put on.
Oh god, did she even own any lingerie?
Penelope walked over to her dresser drawers and dug through them until she found a lingerie set she hadn't worn in weeks. It was clean. It would have to do for now.
She showered and changed into it, letting her wet hair cascade over her shoulders and breasts. Maybe a lipstick or gloss? She wasn’t going to show her whole face, just her lips. She grabbed a ChapStick from her nightstand, rolled it over her lips and rubbed them together.
Then suddenly she got a notification from her laptop.
What?
She walked over, sat down on the edge of her bed and pulled her laptop into her lap and looked at her page. A red exclamation mark was next to the text bubble icon at the top of her screen. Could this be…?
She clicked the chat bubble icon.
LoneTraveler91 is requesting to chat with you…
What? Is this the premium customer?
She clicked accept and the chat opened.
LoneTraveler91 sent 150$ (Hold) — Request: “Send me a picture of your tits.” (Accept) or (Reject)
What kind of picture? Like without a bra?
PFeathers96: With or without a bra?
LoneTraveler91: Doesn’t matter.
Okay, she could do that.
Request Accepted.
Penelope adjusted her laptop screen to show only her cleavage spilling out of her lacy blue bra and snapped a picture then clicked send.
150$ has been credited to your account.
LoneTraveler91: Fuck.
Penelope’s heart was in her mouth, her nerves pooled in her belly. That was it?
The chat dinged again.
LoneTraveler91 sent 150$ (Hold) — Request: “Video of you touching yourself.” (Accept) or (Reject)
Oh. That was fast.
But, for how long? And, it was just to this guy not everyone else. That’s not bad. This was doable.
Penelope took a deep breath and typed out her question.
PFeathers96: For how long?
LoneTraveler91: However long it takes you to come.
LoneTraveler91: I want the sound on. I want to hear from you.
Penelope felt blood rush to her cheeks. This was so incredibly new to her. Someone wanting to hear her come was… definitely different. She didn’t even know how she sounded. There was something comforting in knowing that this person had no idea who she was. They’d never meet in real life and she’d never have to worry about any awkward conversations after that. She could do this.
Request Accepted.
Penelope propped her laptop up on her nightstand and angled just right to get her body length and not her face, the lighting was alright, thankfully she had a nice laptop camera.
She then clicked the record button.
Penelope slid her hand down her abdomen until she came to the band of her knickers then dipped her fingers underneath.
She nibbled on her bottom lip as she slid her fingers along her seam and teased her clit. Her back arched off the mattress and she moaned. “Ah…yes…”
Her movements became faster and faster and she was on the very brink, her pussy throbbed, aching to be filled. “Mm…oh…” but she only had her fingers. She never used toys. Not that she didn’t want to but because she couldn’t afford them and she was so close to being thrown out on the street she didn’t have time to care about pleasure.
Penelope hasn’t done this in a few days, work had been keeping her busy and she needed an orgasm. Desperately.
She clenched and brows knitted together, she was so close. She circled her clit faster and faster and then her back arched— “I need—Ahh!”
She came so hard she felt dizzy, and squeezed her thighs together. But she still felt herself flutter and throb.
Her legs were shaking when she reached over to stop the recording, then in two more clicks she hit send.
150$ has been credited to your account.
LoneTraveler91: Fucking perfect.
Penelope decided to take advantage of her current state and snap a picture of her body with her hand under the front of her knickers, her back arching off the mattress and posted it for her Standard Subscribers.
The chat dinged again not even eight minutes later and she opened it.
LoneTraveler91: I just thought you should know that I came so hard my vision blurred. Have a good night.
Penelope wasn’t sure what to say, she'd still been in a daze from her orgasm, but at least she had the 300$ she needed for rent.
And yeah, she could definitely get used to this.