The Pleasure Girl … [F20] [brothel] [virgin] [sex worker][series][Fsub] … part 1 – Short Sex Story

*I have been writing this story for many years for my own enjoyment but decided today, my 5 year cake day, to distribute it on this sub. If anyone likes it / if it gets a positive reaction, I will hopefully post part II, III, and so forth. There’s not much in terms of a plot, to be perfectly honest. But if you like plotless debauchery, you’ve come to the right place.*


Everyone in the city and on the planet knew about the Manor. Everyone knew that the Manor was the house to go to for the most talented and the most gorgeous girls. The Manor served only the most elite customers from its location a few miles outside the city limits. The 32 pleasure girls, all in their early 20’s, were all incredibly gorgeous and all incredibly talented. Moreover, they all did their work with unmatched enthusiasm and each girl could attest to being a proud slut with cheerful zest and verve and energy.

Separate from the main house was the living quarters for the girls. Each girl shared a bedroom and a full bathroom with a roommate. Their meals were prepared by by master chefs. During the day, they exercised, read, socialized or made trips into the city to visit family and friends, and engaged in numerous hobbies. Each night, they were paid generously for their excellent work. The girls were all quite rich by the time they retired. The Manor’s owner , Mr. Drake, was a multi-billionaire. The girls lived luxuriously and peacefully. Each girl had full control of their respective accounts and the books were kept meticulously by the house’s team of private accountants.

The girls were happy to be living and working at the Manor. It did not do company with girls who did not want to do what they were doing for a living. If a girl did not feel that she could handle this profession and do so with cheerful zest and verve and energy, then they shouldn’t be a pleasure girl.

The Manor was open six nights a week and not every girl worked every night. They each had their own four night per week schedule. The atmosphere inside the Manor was comfortable, clean, understated but warm, rich in color without being gaudy. When they weren’t working, the girls wore whatever they wanted: regular street clothes, dresses, skirts. When they were working, they wore their short silk robes – bras and panties were optional. A team of servants worked behind the scenes throughout the nights: changing beds, serving food during meals, among other tasks.

Jenni, 20 years old, was hoping to join the Manor’s “family” of pleasure girls. She was unique and not simply because she did not have any experience with selling her body for money. Jenni was a virgin.

She’d attended the university for one year on a full scholarship, having graduated a year early from college. But there was something missing from her life, and she wasn’t entirely sure what it was… She spent long hours in meditative silence, thinking about what she wanted from life. She requested and received a voluntary suspension of her scholarship and left her city for the first time on a worldwide backpacking trip. She had an amazing time in the eighteen cities that she visited over an entire year. She met a lot of foreign men who wanted to take her to bed but she didn’t go farther than making out.

When she returned home, she found that her father had fallen ill. The doctors were doing their best to prolong his life but it was clear that they were fighting a losing battle. Jenni was extremely close to both of her parents and treasured her final months with her father. To his credit, he kept his and everyone’s spirits up and maintained his sense of humor up until the end. He had at all times encouraged her to challenge herself and to do things even if they were not just scary, but heart stopping terrifying.

Before her worldwide trip, she had joked about visiting a nude beach with no intention of actually going. Her father had told her that he had visited a nude beach when he was about her age. “It didn’t turn me into a nudist, but I had a great time regardless,” he said. She probably wouldn’t have gone on the trip with its many adventures (kayaking, rock climbing, expansive hikes, nude beach sunbathing, surfing, scuba diving) if not for her father’s advice. She told him that she wasn’t sure she wanted to return to university. He told her that he’d like her to finish but she should feel no obligation to do so because of what he wanted. They had a very sad and, at times, very joyful time for his final eight months.

After four long months of mourning alongside her mother, she returned to the university and graduated the following year, way ahead of schedule. She was now a university graduate at only 20 years old. She considered pursuing a higher degree then decided she didn’t want to go back to university. She wanted to seek out more adventure. She considered another worldwide trip but dismissed it. She procured an excellent job at a non-profit office and moved into her first apartment on her own.

The idea of the Manor struck her suddenly, while she was in the shower. She first dismissed it as absurd. She was a virgin after all – why would the most popular pleasure girl house be interested in a girl who didn’t know anything about having sex? Well, she wondered to herself, maybe they’d be interested in hiring me for exactly that reason? It would certainly be an crazy adventure. She could write a book about the experience!, she wondered. There had been published interviews with pleasure girls before, but Jenni wasn’t aware of any first-person book on the subject. What would happen to a virgin who decided to become a whore? How does a good girl turn into the ultimate example of a bad girl? Such a book could easily be a bestseller. And it would certainly be an crazy adventure.

The more she wondered about it, the more it terrified and intrigued her, simultaneously. She spent several months contemplating the idea and writing about it. She knew that pleasure girls were known for being extraordinarily gorgeous with fantastic bodies – and she wondered that she was gorgeous and she loved her body, especially her round, firm and large breasts. In the last year, her breasts had inexplicably, unexpectedly grown from a C to D. They were 34D, according to the woman who measured her for by her new bra size, and Jenni loved her new boobs.

She wasn’t shy about showing off her body when she went out to clubs with her friends and she received a lot of appreciative looks when she would go out jogging. From the Manor’s reputation, she knew a girl had to be gorgeous and young in order to work there. While not conceited, she was proud of her tightly curved, fit body. She possessed exotic green eyes and rich blonde hair. All in all, without too much conceit, she wondered she was gorgeous.

The ultimate question was whether or not she could transform from a virgin into a sex goddess. She didn’t know if she had a talent for sex…but she wondered she could learn—or be taught—how to be good in bed. She’d never even been entirely naked with a man before. She’d had a total of one serious boyfriend at college, and there had been a couple instances where he had removed her shirt and then her bra. She’d given this boyfriend a very brief hand job – once, through his shorts, while they were making out, and not to its completion. The subject of sex hadn’t ever come up. So she’d never actually seen a man’s penis in the course of her life. Yet despite all of this, the idea dominated her mind. She finally decided to take the leap. She had no idea what she was doing or what she was getting herself into, only that the urge was strong and she needed to let it loose.

If someone answered the door, she was gonna say, in the bravest voice she could muster, “I would like to work here – as one of the girls, please.” Although she was sure that it would be difficult, she believed with all of her inner strength that she could step into this terribly strange new life. She had no idea if she was going about this right way. She didn’t know anyone who had visited the Manor who could answer her myriad of questions about how it operated. When Jenni was still in college, a classmate claimed to have been there, but no one really believed him.

Jenni paid for a carriage to take her to the city walls and then she walked the rest of the way to the Manor. There were guards at the front gate but when Jenni walked up, one of them immediately opened the door for her. The guard simply waved her through. She was wearing a simple pink dress that showed off quite a lot of her legs. It also emphasized her breasts by showing off her lovely cleavage. She’d personally altered it to show more of the top of her breasts and more thigh. Her mother didn’t know anything about this trip, of course. No one knew. She’d left the house wearing a different set of clothes so there would be no questions about where she’d be going in such a fancy (and sexy) dress. She found a public restroom where she’d changed. She’d received a lot of leers walking down the street.

After a moment, a servant answered the door. The servant, a non-descript middle-aged woman, opened the door wide as if Jenni could simply walk right in.

“Yes?” the servant said. “Can I help you?”

“Hello,” Jenni said. “I was, I mean… I am… uh…Her voice suddenly sounded very small. What was she doing here? Was she insane? Was she really trying to do this?

“I wanted to know if it would be possible for me to work here … as a pleasure girl?” It wasn’t exactly what she planned to say, but it got her point across anyway.

“You will need to make an appointment via Mr. Drake’s secretary. She can be contacted at this address.” The servant handed Jenni a company card with an address printed on it.

“I see,” Jenni said. “Thank you.”

“Who’s at the door, Marta?” a voice said, coming from somewhere inside, beyond Jenni’s field of vision.

“It’s a girl interested in working here, sir,” the servant replied. “I was just telling that she should make an appointment via your secretary.”

Mr. Drake came to the door, glanced at Jenni, and smiled. “Well, exceptions can be made. I have a few minutes to talk right now.”

A few minutes later, Jenni found herself sitting in a chair in Mr. Drake’s office. Mr. Drake was sitting on a dark mahogany desk while Jenni sat on a high-backed cushioned chair in front of him. The paneled walls were decorated with paintings of landscapes and seascapes, a framed antique star chart, and a large clock. Against the back wall of the office, there was a large dark red sofa. Jenni was glad that it was behind her, otherwise she wouldn’t have been able to stop looking at it. After making some small talk about the weather, he started in with asking her questions.

“How old are you?” Mr. Drake asked.

“I’m 20,” Jenni said.

“If you don’t mind my asking – how tall are you and how much do you weigh? Your breasts appear to be stunning. What is your bra size?”

She told him both numbers, accurately. She was 5’8” and weighed 120 pounds. Her breasts were 34C. Mr. Drake either didn’t notice or chose to ignore her shy tone. Mr. Drake crossed his fingers on the desk in front of him.

“May I see your body please?” he asked.

Jenni had expected this but wasn’t entirely prepared for the actual moment. It wasn’t surprising at all that he wanted to see her naked. She wondered of it as taking off most of her clothes at the beach, during the summer. Of course, she’d be wearing a bikini on the beach and Mr. Drake wanted to see her entire naked body.

“Of course,” Jenni said.

She wondered about telling him that she was a virgin—but after a moment’s contemplation, she decided to wait. She rose from the chair, took a deep breath that she hoped he didn’t notice, and very deliberately pushed her dress off her shoulders then pushed it the way off, letting it fall to the floor, leaving her in her bra and panties. She didn’t need him to ask her to remove her bra—she did so—but she left her panties on. She stood in front of Mr. Drake, her full proud breasts exposed.

“Your body is magnificent,” Mr. Drake said. “Amazing, truly.” Jenni swallowed. Ever since entering the office and noticing the wide sofa, part of her expected that any minute, he was gonna grab her, throw her down on the sofa, tear off her dress, and roughly take her like a…well, like a pleasure girl. This hadn’t happened, but it seemed like it might happen now. She braced herself, terrified. Would she even have the chance to squeak out her confession? In his frenzied rush to fuck her, would he even hear her? He still had to remove his clothes, but all that she had left was a small swatch of silk covering her vagina.

“Please remove your underwear,” he said, polite as ever. “And please lie down on the sofa behind you.”

She started to speak, and only a squeak came out. She began again. “Sir, are we going to have sex?”

“We are going to fuck,” he said. She paused just long enough. “Is there a problem?” he inquired.

“No, sir.”

“Well then?”

“It’s just that…I’m a virgin, sir,” Jenni said.

Mr. Drake was clearly shocked. “Really? You’re actually a virgin?”

“Yes sir,” Jenni said. “But we can still fuck … if you want to.” She looked down at her panties. “I just wanted to make sure you knew.”

“May I ask you a few more questions, please?” Jenni nodded. “How many boyfriends have you had?”

“Two,” she replied.

“Were either of them serious?”

“No, sir. Not really.”

“How far have you gone with a boyfriend, or any man?”

“I gave my boyfriend a handjob a few times, while we were in bed together,” Gwen replied.

“When you gave this handjob, were you naked?”

“My blouse and my bra were off. But we didn’t go any farther than that.”

“Did he cum during these instances where you gave him a handjob?”

“No, sir.”

“You promise me that you’re telling the truth, that you’re really a virgin?”

“I promise, sir.”

“Jenni, you will pardon me for asking this question, but I must ask it. Why do you want to be a pleasure girl?”

She was completely honest with him when she answered: she was doing this because she was desperate for an exciting life. More than anything, she sought an unconventional life. She was interested in the experiences, and for the adventures, and because it was a totally crazy thing for her to do.

“Jenni,” Mr. Drake said, slowly, “I honestly do not know if a virgin will be able to become a pleasure girl. But this is how I suggest that we proceed, you are free to accept or refuse this proposal. I propose that you return here a couple of nights from now. We will prepare you to lose your virginity, as a pleasure girl. I will invite some of the most wealthy of our clients in a room and you will lose your virginity to one of those men. We’ll hold an auction, and you will be joined upstairs by the highest bidder.”

“You will only have that one ‘appointment’ on that first night. You will be paid the same percentage that every girl here earns: 87 percent of however much the man pays for you in this auction. You can decide at any time not to go through with it, even if the man is already in the bedroom with you, even if he’s about to fuck you, even after he’s started. At any time, you will be able to tell him to stop. If you decide to go through with it, you will be welcomed here as a pleasure girl. If, anytime after your initiation, you decide that a pleasure girl’s life is not for you, we will not and cannot force you to stay. What do you think?”

“I think I can do it, sir,” Jenni said, slowly, hesitantly. She did not know if she could do this. In fact, she had no idea how she was able to say ‘yes’ to all of that.

“Then I will see you tomorrow night,” Mr. Drake said.

After she got dressed, she was driven back into the edge of her neighborhood in a carriage paid for by Mr. Drake. Another carriage would return her to the Manor the following night. She would start her work at the Manor the next evening after that.

Once Jenni returned to her apartment, she began packing her clothes and other personal effects. In addition to the clothes and underwear, she packed some personal items: a framed picture of her with her parents, a necklace she’d received on her sixteenth birthday, a pair of earrings that her best friend gave her when they graduated from college. She also traveled to her mother’s house and invited them out to dinner. She told her mother that she had acquired a new job in a nearby city.

She’d be working as the personal assistant to an millionaire. This story was suggested to her by Mr. Drake before she left the Manor. The new job began the next day, she told her mother, and that’s why she had to move away quickly. The job paid well, she said, and she would have a new apartment. She would be able to visit often, she said, and she would be perfectly safe. Her mother congratulated her on the job and Jenni felt so strange about lying to her. But she couldn’t tell her the truth, not yet, at least.

The following evening, when she emerged from the carriage in front of the separate adjacent building that housed the pleasure girls’ living quarters, Mr. Drake was there to greet her. “Welcome,” he said. “Let me show you to your bedroom.” He noticed her suitcase and asked a servant to take it for her.

“Your roommate will be Mia—but both of you have a lot of space to yourself. It’s a large room.” Mr. Drake said. “Mia is working right now. You’ll meet her and the rest of the girls later. They all know about your arrival and they’re excited to meet you.”

Mr. Drake led her on a tour of the entire living quarters building, with stops to visit the atrium, the gardens, the indoor and outdoor pools/jacuzzis, the spa/sauna (with professional masseuses on staff), the library, the studio spaces (for the girls who were also artists), the music room, tennis courts, the salon, a theater space, a ballet studio, the coffee shop, the fully stocked kitchen, the billiards room, and the gym. The bathrooms were appointed with marble. The beds featured the world’s finest linen and superbly comfortable mattresses. For the duration of the tour, Jenni’s nervousness was temporarily replaced with awe. While Jenni had expected it to be fancy, she hadn’t expected such luxuries.

The tour ended with Mr. Drake leaving Jenni sitting on her bed in her new bedroom. A servant appeared holding a tray with a cup and saucer.

“I’ve had the kitchen prepare a tea for you. I think it may help you relax so that you can sleep. We need you well rested, since you will have a full schedule tomorrow. Good night.”

Jenni drank the delicious tea slowly. She didn’t think she was gonna be able to sleep, due to her nervousness that was quickly approaching terror and the rush of ideas in her mind, but the tea did its job. She was sleeping peacefully within fifteen minutes of closing her eyes.


End of Part I.

NSFW: yes

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