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Sterling Stories profile
Sterling Stories
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Sterling Stories
I write erotic literature! Mainly femdom and feminization themed, but I don't limit myself to just those topics. Finished stories can generally be found on LushStories, https://www.lushstories.com/profile/SamanthaJackson/stories
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Sterling Stories

Story index


To help with navigating through my stories and make it a little easier for new visitors to find stories they might like, I decided to make a spreadsheet of my stories, along with their most notable tags and some extra information regarding the type of story, the only availability, and their links. In the event of a "freemium" story, I have included both the free and the premium link, as the stories are slightly different from one another (extended and/or uncensored).

I'll update the list whenever I publish a new story (or whenever I feel like teasing a new title).

Thank you so much for your continued support! Love you all <3

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Displaying posts with tag Announcement.Reset Filter
Sterling Stories
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 An Unexpected Proposal [Preview + announcement]

Being tight on money, it was an offer that couldn't be refused.

PSA: For health reasons, I sadly need to take a break from writing. I aim to continue writing when I recover, but I cannot put an estimate on when that will be. I will still be around, and you can still contact me on Discord, Twitter, or even here, as always. I just won't be writing stories while I recover.

----
"Well, there goes another one," Harry said in defeat as he left the warehouse and headed for the bus stop. It was the third job he quit within its probationary month. The third job in a row in which Harry thought he finally found a job he could keep up with, only to end up struggling regardless and throwing in the towel after one week, if not earlier.

The end of the month was nearing, and the bills for utility, rent, and many other necessary 'subscriptions' were soon to come in. While walking, Harry checked his mobile banking app, despite already knowing the answer. He simply did not have enough money to afford all of his bills. Frustrated, he wondered if he could still borrow money from some of his friends or family, but it wasn't the first time he had to ask for financial help, and he feared his luck was running out.

Sitting on the bench at the bus stop, Harry opened one chat after the next, wondering if he could ask this person for help, and how. But eventually, Harry put his phone away, as it only made him more worried and desperate. With restless feet, he looked around, hoping to find any kind of distraction. Dropped coins on the sidewalk, a job opening taped to a window, the number plate of a car passing by... anything to take his thoughts away. But nothing seemed to help.

When the bus finally arrived, Harry got in and put his hands in his pockets, looking for his travel card, but he could not find it. "I seem to have misplaced my travel card," he apologized to the bus driver.

"Not my problem," the bus driver responded impatiently. "Rules are rules, and I cannot make exceptions. Pay, or leave."

Harry sighed loudly. Could this day get any worse? He thought to himself as he turned to exit the bus.

"I'll pay for him," a voice interjected.

Harry turned around in surprise and found himself looking at a tall, black-haired, middle-aged woman dressed in black. Her clothing and jewelry style seemed very expensive. Harry wondered why this woman was even taking the bus, as he imagined she could easily afford her own private chauffeur. Perhaps she wanted to make an environmental statement, Harry thought to himself.

The woman paid Harry's fare and asked him to sit with her as she walked to a secluded area in the back of the bus.

"Thank you, ma'am," Harry said humbly as they sat down. It remained quiet for a few seconds as the bus started driving again.

"Well," the woman said in anticipation. "You're not just going to sit here in silence, are you? Tell me a little about yourself!"

"Uhm," Harry said as his eyes darted around the corners of his eyes. "What would you like to know?"

"Let's start with your name," the woman smiled. "I'm Cindy, by the way."

"H-Harry," Harry stammered. "My name is Harry."

"Well, Harry, how did you get on this bus? Do you often take this bus? Where are you headed? Where did you come from? You had better not be getting out any of the next few stops already. I'm intrigued to know more," Cindy laughed.

"I uhm... I started a new job here recently. But I quit today because it was just not working out," Harry sighed. "For now, I'm headed back home. Soon I'll probably have to pack up and move in with my parents again, though. Because at this rate, I won't be able to afford the rent much longer."

"Oh," Cindy said. She paused for a moment before reaching into her black jacket, procuring a briefcase-shaped wallet, opening it, and taking out a business card. She held it in her hands for a few seconds, studying the card in thought, before handing it to Harry, saying, "If you're in a bind, I might be able to help you out."

Harry inspected the business card. There was an abstract logo, Cindy's name, a phone number, and an address, but no indication anywhere that said what her company even does. Confused, Harry stared at the card. "What exactly is it you do?" He asked.

"I organize fetish parties for rich businessmen," Cindy replied nonchalantly. "They have been wanting to try some new things, but I could never find the right person for the role... until now." She smiled.

Harry stood up abruptly. "Sorry, I'm not interested," he said as his face turned flush.

"My apologies for misjudging, then," Cindy said. She crossed her legs and looked out of the window. "Good luck with your rent. You're welcome to give me a call if you change your mind... I wouldn't wait too long, though."

Harry hesitated. He knew he desperately needed money, but this seemed... a bit too shady. Still, he could not walk away before asking Cindy a final question. "How much does it pay?"

"More than enough to pay your rent," Cindy said, still refusing to make eye contact.

Harry looked around and considered his options for a couple of seconds before sitting back down. "Alright," he sighed. "I guess I could use the money... Maybe I'm interested after all."

Cindy turned back around to face Harry. "Great!" She said with a slight smile. "Basically, all you have to do is to put on a latex suit and be the plaything of three well-off businessmen for a single night. Do that to their satisfaction, and you'll receive 500 dollars-"

"500 dollars?" Harry interrupted. "That doesn't cover my rent at all!" He stood up again to leave, but Cindy grabbed his arm tightly.

"500 dollars from each of them," Cindy continued. "It would help if you'd just let me finish... Anyway, that means 1500 dollars for... maybe 5 hours of work. I doubt you could find any other job that could pay you that much for a single day's work."

"And how often is this?" Harry asked hesitantly.

"If you do a good job, and they want you back, once or twice every month," Cindy said. "Worst case scenario: you don't live up to their expectations, earn half, and that's that. Giving you a little extra time to sort your finances out. Best case: you only work for 10 hours a month, and get to spend the rest of your days however you please!"

"And when do I start?" Harry asked. 

"You can drop by tonight at my place for your assessment; it's the address on the card. I'll take your measurements, sort out your clothing, and give you some pointers for the event, which will take place the week after."

"And this event is at your place too?"

"No. The event itself will take place at a private sex dungeon," Cindy clarified. "But I'll bring you there myself, blindfolded, of course. This is purely to protect my clients' identities. Once inside, I'll remove your blindfold, so you can see what you are doing, while the clients will wear masquerade masks."

"And what exactly am I supposed to do?" Harry asked.

"You're the entertainment. So, entertain!" Cindy winked. "Although, the clients usually make it pretty clear what they want, so don't sweat it. Just do as they ask with a bit of enthusiasm, fake it if you have to, and you'll be fine. During the event, I'll observe from behind a one-way mirror, to ensure the safety of 'my merchandise', and afterward, I'll take you back home and give you your payment. If you are requested back for another event, I'll give you a ring."

"And if I don't want to go again?" Harry asked.

"Then you're off the list," Cindy said matter-of-factly. "No hard feelings or resentments. You'll be free to go. But it also means you will not be able to work with us again. Once you're out, you're out."

"Hmm," Harry hummed in thought. "Alright. I'll give it a shot. It's not going to be anything too extreme, right?"

"Oh, no. Not at all!" Cindy said. "Maybe just a little, but everyone's safety and hygiene will be safeguarded at all times."

Suddenly, Cindy stood up. "Well, this is my stop!" She said. "See you tonight. 8 PM sharp, don't be late." As she walked to the bus's exit, it came to a halt and the doors opened, despite being nowhere near any kind of bus stop. Cindy got out, and the bus continued its journey as if nothing had happened. 
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