The Pleasure Girl … [F20] [brothel] [virgin][auction][sex worker][masturbation][series][Fsub] … part 2

[ Please read part 1 before proceeding (see profile). ]

The next morning, Jenni’s preparations began, as soon as she woke up. In her bedroom’s closet, she found a selection of dresses and skirts (some sexy, some benign), silk robes and a small chest of drawers with bras and panties, some plain, some colorful and small and sexy. She ate a small breakfast alone and met some of the other girls, who were all friendly and welcoming. She bathed with servants attending her, using special soaps and bath salts, making her skin more smooth and supple. Her legs were shaved and treated with lotions. Her hair was cut (just a little bit) and styled so it curled some at her shoulders.

After the haircut, her hair was shampooed again, extensively. Her pubic hair was neatened with a tiny pair of scissors and (painless) wax. She thought the small triangle of neat hair looked cute. She had a brief checkup with a female doctor who verified that she was healthy enough for sexual activity (she was) and she also verified that Jenni was, in fact, a virgin. The doctor also supplied her with a single pill that would keep Jenni from becoming pregnant.

“Are there any side effects?” she asked Mr. Drake, tentatively.

“There’s a couple, actually, I’m glad you asked. It happens to help keep your pussy tight. And wet.”

Jenni was stunned. “Are you joking, sir?” she asked.

“No, I’m entirely serious,” he said, smiling. “You can ask the other girls.”

After all of her appointments, she was escorted back to Mr. Drake’s office. “It’s remarkable,” Mr. Drake said. “I didn’t think you could look even more beautiful than when I first met you.”

“Thank you, sir.”

“Are you nervous?”

“Yes, sir. Very nervous.”

“Don’t be. You’ll do just fine. I guarantee that everything will go smoothly. For now, please return to your room and rest. I’ll come get you when it’s time to start. … Oh! I nearly forgot to tell you this. All of the girls adopt a new name when they become a pleasure girl. So you need to decide on what new name you want for yourself?”

She took a moment during her day to ask Mia one of the pressing questions that had been weighing on her mind: “What position do you think he’ll want me to be in?”

“Probably missionary. You know what missionary is, right?”

“Yes… But…this might be a really stupid question…but how far apart should I spread my legs for him? I don’t want to do it wrong, I don’t want him to have to correct me.”

“It depends on the girl and on the customer. But we’re about the same height, let me show you how I do it.” Mia laid down on her bed and spread her legs a several feet apart, her knees arched and her pelvis tilted up. Jenni copied the position from her bed.

“If the customer wants to treat you like you’re an experienced pleasure girl, he might want to fuck you doggy-style. I doubt he will, but it’s possible. I assume you know what that is?”

Jenni did but asked Mia to show her the position anyway. Jenni imitated her again, and Mia got on the bed with her to pass on some additional tips.

“Stay like you are right now. Are you comfortable with my touching you for a second? I want to show you how the customers will touch you when they’re doing you in doggy, okay?”

“Yes, okay…”

“The customer will either put his hands here,” Mia put her hands on either side of Jenni’s waist. “Or if he might grab your boobs.” Mia did not touch Jenni’s chest. “You might have to tell a customer to not be so rough if his hands go there. If he wants to go ’cowboy’ — that’s what I call it — he’ll grab you here.” Mia put her hands on Jenni’s shoulders. “And some girls like this, some girls don’t, but you’re sometimes going to get your hair tugged on when a customer is fucking you from behind. Just so you know.”

“If you don’t mind my asking – what was your first appointment like?” Jenni asked another girl, Laci, later in the day.

“Oh, I was terrified!” Laci replied. “I’d never been fucked by a complete stranger before my first night as a pleasure girl. And I was scared he’d be too rough or he’d have a monster cock or he’d want me in some bizarre position or I wouldn’t be able to make him cum … but my first appointment was so much fun! The customer was more than satisfied and I was super happy and ready move on to my second customer. You’ll find out once you start working – we have the most amazing job in the world!”

A couple hours later, Mr. Drake reappeared at her bedroom door. A half hour before, a servant arrived to apply light makeup and lipstick. Jenni was wearing her robe and nothing else, as instructed by the servant, who was passing along instructions from Mr. Drake.

“Are you ready?” Mr. Drake asked.

“Yes, sir,” she said. “As ready as I’ll ever be.”

“Don’t worry. You’re going to be great. Have you decided on a name for yourself?”

“I thought I could be Gwen?” Jenni said.

“Excellent choice. It’s a naturally sexy name. Follow me, please.”

“Let’s run down what’s going to happen tonight. Please tell me, step-by-step, so I know that you understand.”

“Yes, sir… I’m going to stand on a stage … where everyone will be able to see me. You’re going to give a brief statement and then ask me to take off my robe. Then I’ll give the short speech that you asked me to memorize. After that, one of the girls escorts me out, I’ll wait upstairs while the auction is conducted.”

“Then?”

“Then … the winner of the auction will meet me upstairs, I’ll do whatever he asks me to do… he’ll be the first person to have sex with me.”

Mr. Drake smiled. “I was hoping you’d be a bit more explicit.”

“Oh, sorry,” Jenni giggled, despite herself. She often giggled when she was extremely nervous.

“Well…this man will be the first person to put his cock in my pussy and fuck me… “

She literally had to stop herself from using the clinical words; she couldn’t recall ever using the words ‘pussy’ or ‘cock’ before. Gods, she was so scared… How did she ever think she could do this? Yet it was happening! It was all happening!

“I’m really scared, Mr. Drake,” she said.

“I know you are,” he said. “But believe me, everything is going to be just perfect. There’s going to be about fifty of our most wealthy clients in the audience for you. I would like you to remember: if you need the winner of your auction to stop for any reason at any point, regardless of how far you’ve gone, you can use the stop word – ‘drake’ – and he will stop as soon as possible. This is an option, but if you decide to use it, you will obviously be halting your pleasure girl career immediately. But I don’t think you’re going to back out. You’re going to be one of the most famous girls in the country in a matter of minutes.”

Mr. Drake opened the door for her and she walked inside. The room was empty except for the two of them and a pleasure girl named Laci who Gwen had met earlier in the day.

Laci squeezed Jenni’s hand. “This is it,” Laci said, smiling and squeezing Jenni’s hand. “You’ll only have to be up there for a few minutes. Then I’ll take you upstairs to the bedroom. We can go slow if you need to walk slowly. I’m sure your auction isn’t going to be a quick affair.”

“I can’t believe I’m really about to do this…” Jenni whispered. “It’s going to be fine, as smooth as silk,” Laci whispered back.

“Avoid looking down at your feet,” she added. “Pick a spot at the back of the room and focus there. Be confident. Also, when you’re naked, arch your back and push out your chest. It’ll make you look super hot.” She quickly kissed Jenni on the forehead. “This part will be over before you know it, trust me.”

Mr. Drake led her toward the stage. She walked up the couple of stairs and then onto the stage, with Mr. Drake next to her. “Any questions before we begin?” he asked. Jenni shook her head. Mr. Drake produced a small whistle from his pocket and blew it once.

A moment later, the double doors on the opposite side of the room were opened by a servant and a large crowd of men entered. Immediately, all eyes were on her.

Oh my gods, she thought, all of these men are going to be competing for me! Me! My body! And in a minute, Mr. Drake is going to ask me to take off my robe! I’m going to be totally naked in front of all of these men! And one of them is going to have sex with me! Gods, what am I doing here? !

“Gentlemen, it is my extreme pleasure to introduce Gwen to all of you.”

She scanned the crowd, hoping she didn’t look as terrified as she felt. Most of the men were much older than her, although there were a few who appeared to be in their 20’s.

“We are looking forward to adding Gwen to our family of pleasure girls, but first, as you will all know, there is the little matter of her virginity. Her virginity is the reason we are gathered here today for this special event. I’m sure all of you would like to see her as she’ll appear on the bed tonight and for many nights to come. Gwen – would you please take off your robe?”

Gwen took a deep breath, untied the sash and removed her robe, letting it fall to the floor. A murmur of approval went through the audience. She was entirely naked in front of all of the men who all stared at her body. She thought about taking off her jeans and shirt at the beach when she was wearing a bikini underneath her regular clothes. This really wasn’t that much different, was it? She wished that she had the courage to strike a sexy pose in front of them, but she did remember to arch her back (just a little) to accentuate her large round breasts.

“My friends, we can all see that she has a remarkably beautiful face and an equally beautiful body,” Mr. Drake said. “And if you are the winning bidder, she will be yours for the hour. You may do whatever you would like to her, as long as you adhere to our house’s rules and as long as you take her virginity. I will start the bidding in just a moment. But before we begin, Gwen has something that she would like to say. Gwen?”

“Thank you all for attending my auction tonight,” Gwen said, her voice shaking only a little. “As Mr. Drake stated, I am indeed a virgin. One of you will have the honor of being the first person to take me to bed, initiating me into the life of a pleasure girl. For the majority of you who won’t be joining me upstairs tonight, I look forward to a future appointment with you, after tonight’s activities.”

The men actually applauded. Gwen nodded to the crowd and resisted the urge to cover her breasts with one arm and her pussy with her hand.

“Now,” Mr. Drake said. “Laci will be escorting Gwen upstairs so she doesn’t have to stay here and listen to all of this competition. She will be waiting for you upstairs, I promise you.”

Gwen stepped off of the stage and Laci placed the robe back around her shoulders. Part of her wanted to leave the robe untied and open, but she decided against it, tying the robe around her with its sash. They walked together out of the room through the nearest door, without having to walk through the thick crowd.

“Okay, so that hard part’s over,” Laci said to Gwen as soon as they had exited the room through a door behind the stage. “And everything went well, right?”

“Right.”

“Now all you have to do is ‘hurry up and wait.’ You looked fantastic up there. Incredibly sexy.”

“I don’t know if I felt sexy? I think all of them could tell how scared I am.”

“I assure you,” Laci said, “They expect you to be nervous. And they’re not going to mind…”

The two girls walked toward the bedrooms together. “Did you get a good look at the men? Were any of them young? Or were they all old or middle-aged?” Gwen asked.

“From what I saw, a few of them were in their 30’s,” Laci said. “I didn’t study the crowd too closely.”

“I was thinking last night that it would be easier if he was handsome and young, but then I realized that if it was an older guy, he might be slower and more gentle?”

“Well, in my experience, you can never really tell the bedroom personality of a customer just by looking at him,” Laci said. “I’m frequently surprised.”

“I noticed some Black men in the crowd … Is it … Is it true that they’re particularly, um, girthy?”

Laci smiled, comfortingly. “I had the same question when I started here, only because I grew up in a small town. The answer to your question is ‘sometimes’ … and not any more often than guys of other races.”

“Do you…gods, I can’t believe I’m asking this … Do you think he’d shoot his cum in my mouth if I asked him to?”

Laci seemed mildly surprised by the question.

“Wow. Um… well… I’m think he’d probably do it if you asked,” she said. “Have you ever had someone cum in your mouth before?”

“No, never. I just thought that as long as I’m trying … as long as I’m becoming a pleasure girl tonight, I should try to do as much as I can…to get it out of the way…?”

“You should do what feels right for you,” Laci said. “but don’t make it too overwhelming for yourself.”

“Will he want to put it – his cock in my mouth before he fucks me?”

“I’m guessing you haven’t ever done that before either?”

Gwen shook her head.

“If I was to guess, I don’t think he’ll be interested in getting a blowjob. He’ll probably want to start fucking you as soon as possible.”

Laci opened the door to a lavish bedroom, accented with dark blues. Gwen’s attention immediately focused on the huge bed. She sat down on the bed, feeling like her whole body was shaking. Laci sat down next to her.

“I … I don’t think I’m going to be very good.”

Laci smiled kindly. “Don’t worry. You’re going to do great. Just remember to breathe when he’s about to start. You’ll want to hold your breath, but don’t. Feel free to scream if you need to, if it hurts really bad. I can almost guarantee you that he won’t mind if you have to scream.”

Laci hugged her and stood from the bed. “My best advice is to try to have fun. I’ll see you later, after you’re finished, okay?”

As soon as Laci closed the door behind her, Gwen stood and tried to open it again, half-expecting that it would be locked from the outside. It wasn’t locked.

Gwen appraised her surroundings. She looked at the bed where, in a matter of minutes, a man would fuck her for her first time. She closed her eyes and imagined herself there, her legs spread wide and the auction winner’s body atop hers, pumping away madly at her pussy. She would be expected to please him, do whatever he wanted, fuck him back passionately. Any lack of enthusiasm, any hesitancy, any complaining, any missteps, he would almost certainly let Mr. Drake know. And she didn’t want to disappoint.

Where should she be when the man arrived? Should she sit down on the bed? Should she already be naked and lying on the bed? Should she strike a seductive pose for her first customer to see as he entered the room? She stretched herself across the bed like a cat, extending her arms over her head. No … She wanted to be able to look him in the eyes when he entered the room. She got up and stood at the foot of the bed, interlocked her fingers behind her head and jutted out her chest. She felt silly.

Her whole day had been meticulously planned out, even down to the time she had to relax before the night began. Now she had no idea what to do. She wouldn’t know what to do when her first customer actually arrived, but she expected that he would … take control of the situation. How long did she have to wait? If it took more than an hour… would she back down? She could escape. She could get him to stop at any point. Mr. Drake had given her the stop word, so she could get him to stop, even after he’d put his…his cock inside her … pussy. She’d have to get used to using those words, instead of the clean, clinical terms. Pussy. Cock. Fucking. A cock fucking her pussy. How much longer was it going to be? Auctions were supposed to be quick, weren’t they? How much was someone going to pay for her? Hundreds? Thousands? Thousands for (at most) an hour with her, although part of her knew that it wouldn’t take an hour for the man to finish.

She decided it would be better if he didn’t have to tell her to lie down on the bed. Gwen laid down, in the middle of the bed. Her robe stayed on, for now. She wouldn’t be wearing it for very much longer. She wondered how big the man’s cock would be. She wondered if it was going to hurt and if so, how badly would it hurt? A few of her girl friends had lost their virginity. Some said that it hurt like hell. Some said that it was the most pleasurable experience of their lives. Gwen didn’t know who had been telling the truth and who was exaggerating. What would her friends say if they knew where she was right now? They wouldn’t believe it. Would the man be slow and gentle with her … or would he be rough? In other words, would he treat her like a virgin or a pleasure girl? Right now, she was both. Not for very much longer.

An idea came to her: something that she could do while she was waiting, that might make help her initiation. She would have spent some time thinking about it, but there was no time for thorough contemplation. Her right hand moved between her legs, and with a couple fingers, she spread the lips of her pussy. Her other hand immediately followed and found her clit. This was something she’d tried before, ever since she first started having boyfriends. She rubbed and stroked, focusing on her clit, but slowly. She felt herself getting wet. She deliberately remained as still as possible as she rubbed herself, not wanting to look disheveled. Quiet moans escaped her mouth. She began rubbing a little faster, with hardly realizing she was doing so. She was still focused and beginning to get close to an orgasm when a man entered the room.

Source: reddit.com/r/Erotica/comments/x1wv0k/the_pleasure_girl_f20_brothel_virginauctionsex