The Pleasure Girl … [F20] [F42][brothel][loss of virginity][auction winner][virgin] [sex worker][series][Fsub] … part 3

[[Part 1.]](https://www.reddit.com/r/eroticliterature/comments/w7dzy4/the_pleasure_girl_f20_brothel_virgin_sex/)

[[Part 2.]](https://www.reddit.com/r/eroticliterature/comments/wrmhnp/the_pleasure_girl_f20_brothel_virginauctionsex/)

“Oh! Hello! Hi. … Hi…” she said, shyly. “This is a little awkward! I was … getting ready for you…”

Absurdly, as she stumbled over her words, she simultaneously thought “doesn’t anyone knock any more?” But why should he have knocked? A pleasure girl wasn’t apt to receive that courtesy. He was as likely to knock as he was likely to ask her permission before he started to fuck her!

“I can see that,” he said, smiling. “Thank you for thinking ahead.”

“You’re welcome,” Gwen said. She shivered, visibly.

“Are you scared?”

“A little,” she said.

He arched an eyebrow at her.

“Okay, I’m really, really scared. Fucking terrified.”

“There’s no need to be scared at all, Gwen.”

Gwen giggled. “That’s easy for you to say. You’re not about to lose your virginity to a total stranger!”

The man laughed as well.

“We’re both going to have an excellent time tonight,” he said.

“I hope so,” Gwen replied.

He had a nice smile, she thought. She judged that he was in his late 30’s or early 40’s. Tall. Dark blonde hair. Wearing an expensive-looking, tailored suit. Clean shaven. No wedding ring. Handsome.

“You can get underneath the covers if you want…” he added. “it’s a little cold in here.

“Thank you, I’m okay,” she said. “Even if I was cold, I won’t be for much longer, right?” She giggled again.

“If you don’t mind my asking,” she said, hesitantly, “how much did you pay for me, sir?”

He began taking off his clothes, starting with his jacket and tie, and stated the number.

Gwen gasped then giggled, in spite of herself. “That much?” she said. “Wow. I didn’t think it would be that much. Seriously. And … I bet you plan on getting your money’s worth, aren’t you?”

“Indeed.”

“Congratulations, sir,” Gwen said. “Mr. Drake suggested that I should congratulate you. I … sincerely hope you have an excellent time with me tonight.”

“Thank you,” the man said. “But I don’t think this is time for conversation. I think we must get down to business, so to speak.”

“Sorry, I really talk too much when I’m nervous …”

“No need to apologize,” he smiled at her again.

“So … what … what would you like for me to do first?” she asked.

Her voice quivered, despite her best attempts to sound confident. She was almost positive that he was going to ask her to get down on her knees and prepare to suck his cock, something she’d never done before. She readied herself to tell him as much. She’d warn him to not expect a very competent blowjob.

“Please take off your robe, I’ll be joining you in a minute. I want to get a good look at you before we get started…”

Gwen followed his instructions then dropped the tiny silk robe next to the bed. Without thinking, she crossed her legs at her ankles. She looked down at her breasts, knowing that he was looking at her.

“Have you ever had sex with a virgin before?” Gwen asked. “Or am I your first?”

“You’ll be my first,” he said.

They locked eyes for a moment and he must have seen the fear behind hers. Her whole body felt like it was quivering.

“Are you absolutely ready for what will be happening a few minutes from now?” he asked, in a kind voice. “In a few minutes, you’re going to lose your virginity.”

“Yes, I’m ready, sir. I’m very scared. But I’m ready.”

“As far as changing your mind at the last minute – or even after the last minute – I know you have the right to stop me from proceeding at any point but I don’t think you’re going to.”

“No, I’m won’t tell you to stop,” she confirmed. “I’m just hoping that I’m not going to be terrible… I just don’t know how it’s going to go. I’m scared you’re going to be disappointed.”

“I won’t be disappointed because you’re going to be perfect, Gwen,” he said. “With a body as beautiful as yours, there is no way you could be anything but perfect.”

As he spoke, he finished taking off his clothes, leaving his underwear for last. Now that he was all but naked, she could see how strong and fit he was. He removed his boxers and for the first time in her young life, Gwen saw a naked man’s cock. It was veined, thick, long – she estimated it at about seven inches.

She’d seen pictures in books and she’d seen the outline of her boyfriend’s erect penis through the fabric of his underwear, but never one in real life, so raw. She couldn’t take her eyes off of it. It looked so big. How was something so big going to possibly fit inside of her?

“Oh my goodness,” she said. “That’s … that’s very impressive. Would you believe that this is only the second cock I’ve ever seen in real life?”

He looked incredulous.

“Really!” she asserted. “I gave my university boyfriend a handjob a few times. But he never came. Ridiculous, right? … Is it okay if I touch it?”

“Of course.”

Gwen moved so that she was sitting on the side of the bed. Cautiously, she reached out her hand to touch his cock lightly, running her fingers across it.

“Oh my gods… it’s so thick — and so hard! I can’t believe this is going to be inside of me…”

Gods, could she do this? How much would it hurt? Would he even listen to her if she asked him to be gentle? She could still back out of this. No harm in changing her mind! She could tell him “No, I’m sorry, I can’t do this!” right now before jumping off the bed and wrapping the covers around her. And he’d have to stop. He’d be tremendously frustrated, with all of his sexual energy unspent — but this man didn’t have seem to have a particularly unkind demeanor. In fact, he seemed kind and caring. But that didn’t mean that he would be kind and caring once he started to fuck her! She knew damn well that men magically became partially deaf when in the heat of sex.

She thought about asking if he wanted her to use her mouth on him — then almost immediately decided against it. She knew that she’d have to learn how to give a blowjob very soon, but it seemed ridiculous for her to volunteer for another forbidding task in the middle of her terrifying initiation.

“Please promise me you’ll be gentle…” Gwen said, moving her hand away from his cock. She moved back to the center of the bed, sitting up against the headboard. “I… I want to make sure you feel good. You should feel good. You paid a lot for me after all… But I’m really scared… I just hope I’m able to please you…”

“You’re going to be amazing, Gwen. And I’ll do my best to be gentle,” he said. “I don’t want to hurt you, but it may be inevitable…”

“I know.” She sighed and giggled a little at her own increasing nervousness. “My friends in university, the ones who lost their virginity, some said it hurt like hell, and others said it–”

“Shhhhh,” he said, interrupting her with a whisper. “Lie back down and spread your legs, please. Wide.”

Oh no! Oh fuck! She could have remembered to do this without his having to ask! She cursed herself inwardly. She should have remembered to do it, instead of rambling nonsense about her friends losing her virginity. But she was so nervous! Terrified — and strangely excited at the same time.

As instructed, she spread her legs wide, her knees bent, remembering Mia’s lesson. Their width must have met with his approval. She thought he’d tell her to spread them wider or that he’d even move them further apart if he thought she was being too timid.

“Like this?” she said, her voice sounding small.

“Perfect. I must pause to point out that you have the most beautiful pussy I’ve ever seen in my life.” He was stroking his cock with his hand now but Gwen hardly noticed.

“Thank you,” Gwen said, blushing. “But I bet that’s what you say to all the girls whose virginity you win in a pleasure girl house auction,” she added, her nervous giggle returning.

He laughed and slowly moved so he was on top of her, their bodies touching.

“Oh! Oh my goodness! Hello,” Gwen blurted out, not knowing what else to say.

“Hello there,” he said. He kissed her softly on her mouth.

She was more terrified than she’d ever been in her life. Her heart felt like it was going to explode out of her chest. Her nipples became hard as they brushed against the man’s chest. She could feel his cock against her thigh. It was so close now. She felt like he must be able to feel her fear, just as she was able to feel the heat coming off his body. She couldn’t back down. More importantly, she didn’t want to back down. She was going to go through with this. He was going to turn her into a pleasure girl.

He kissed her again, passionately, and she kissed him back. Her body was trembling. She felt his thighs press hers so that they were just a little bit wider. Gwen moved against him, just as she’d done when making out with one of her boyfriends on a bed. Except she hadn’t ever been entirely naked, of course. She squirmed and moved so her breasts rubbed up against him as they kissed. Her pussy, still wet from her attentions before his arrival, became even more wet.

He bent his face down and kissed her neck, gently nuzzling. Gwen moaned softly, feeling her pussy becoming even wetter. She was simultaneously so scared and so turned on; she’d never felt anything like this before. He put his hands and then his mouth on her breasts, massaging and kissing them, even gently sucking on her nipples.

She suddenly wondered if he’d want them to change position before he finished. Before he finished… Oh gods, what would happen when he came?! Would he want to cum in her mouth? She was going to ask him if he was going to do that, but she’d totally forgotten! Would she be able to take his cum in her mouth without gagging? How much cum would there be? Maybe he would pull out and cum on her breasts? Or on her face?

He kissed her on her mouth again and drew himself closer to her. “Lift your knees, just a little bit more, please,” he said and she obeyed.

He broke their kiss and she felt him press his thick cock against the light pink lips of her pussy. There was no mistaking it for anything but what it was. “That’s his cock on the edge of my pussy!” she thought. “His cock. Oh gods! Oh my gods!”

Part of her wanted to tell him to stop immediately but a more logical and stronger part of her knew the truth: it was too late to stop now. She was going to go through with this. She kept her eyes on his. He looked down at her intently.

“Are you ready?” he asked.

“Yes…” Gwen said, her voice sounding very small to herself.

“Oh gods, it’s so close now! No turning back!” Gwen thought to herself. “It’s really going to happen! Any moment now! Don’t scream, don’t scream, please don’t…”

Gwen cried out as his cock parted the lips of her pussy and entered her. Days before this moment, she’d vowed to herself that she wouldn’t scream. She’d held on to his thought, despite Laci’s advice. But she let out a short scream now, because it hurt so badly! The pain was unreal! Beyond anything she could imagined!

Moving very slowly, he pushed more of his cock into her. Gwen whimpered and bit her lower lip, desperately holding back a scream.

“Oh gods!” she gasped as he moved further still. She wanted to scream out again now, at the top of her lungs, as loud as she could, but she managed to stop herself by gritting her teeth. She could feel how deliberate he was being, moving his cock into her slowly, rather than driving his whole length into her with one hard thrust. He hadn’t even started really fucking her yet! He was only concerned with slowly moving his cock all of the way into her. This was only the prologue!

“Oh gods oh gods oh gods!” she whispered and let out another cry of pain.

He sealed her mouth with a kiss and she kissed him back desperately. She moaned into his mouth, holding back yet another scream. He broke the kiss and she bit down on her lower lip again. She looked up at him with her eyes alternatively wide and scrunched as she contended with the pain. She realized that her pussy was getting incredibly wet from him being inside of her.

Moving slowly, he withdrew, but only partially, then, moving very deliberately, he pushed into her again. She cried out repeatedly. She didn’t feel like she could stop crying out!

She realized his entire cock was now inside her! Inside her pussy! It was so fucking big! She could feel all of it, every inch of him! Now that he was inside her, he was going to fuck her! She was helpless to his cock, open for whatever he wanted to do with her.

“It’s so fucking big, sir!” she cried out.

“I know, Gwen,” he said. “I know… You’re doing so great…” He held himself inside her, still not yet moving, letting her body get used to its invader.

“I’m not a virgin anymore!” she thought to herself, even though this was absurdly obvious. “This anonymous man has paid for and taken my virginity! And I’m a pleasure girl now. I’m a whore! A whore! And I’m going to be fucked by so many strangers and take all of their cum, starting with this man on top of me right now!”

These thoughts were actually a relief, because she now felt that she could never go back from being Gwen. Even though it hurt so much, it somehow felt like the worst of it was over. She was still scared, but not scared about losing her virginity because it was most definitely gone.

He began to move inside her, fucking her. He moved slowly, rhythmically thrusting in and out of her wet pussy. Every inch of her body felt like it was covered in sweat. She moaned loudly in rhythm with his thrusts and these steady moans were accompanied by tiny quiet cries from the pain. She was incapable of stopping herself.

She’d expected it to hurt, but not this much. It was indescribable! She’d thought her girl friends had been exaggerating when they’d described feeling like they were being torn apart, but clearly they’d been telling the truth. She could feel her tiny pussy stretching and contracting around his cock with each thrust into her. It hurt so much, but … shockingly, through the pain, there was a degree of pleasure too! It was confusing and terrifying!

She hoped the man was enjoying her, despite her discomfort. He deserved to get his money’s worth; he’d paid so much for her! From the expression on his face and his grunts of approval, she thought he was having a good time.

“Unnh! Unnh! Unnh! Oh gods! Oh gods, oh, it hurts! It hurts so much!” she cried out. He responded by intensely kissing her. She kissed him back with equal fierceness.

“Do you want to stop?” he asked, looking concerned. But he continued his thrusting into her as he spoke. She was sure he knew what her answer would be without his having to ask.

“No, no, don’t stop, keep going, please keep going, I can take it! Oh gods! Ohh! Ohhhh my gods! Fuck! Ohh! Unnhh!”

“You’re amazing, Gwen!” he said. “Everyone is going to be so fucking proud of you!”

“I’m going to be … proud of me too!” she gasped out. For the moment, she was experiencing so much at once, she didn’t have any room for pride. “I can’t believe this is … really happening! I can’t believe … you’re inside me! Inside … my … pussy!”

She took his cock obediently, like the pleasure girl she now was. She moved with him, lifting her hips to meet his slow thrusts. She squirmed against him in a way she hoped was pleasing. She wanted to participate; she didn’t want to just lie there. After all, she was a pleasure girl now!

“Your tight — your tight pussy feels so freaking amazing!” he said.

“Oh! Thank you! I didn’t realize …I was so small! I didn’t know I was so small! Oh! Oh! Oh gods! Oh gods! Oh my gods! Oh fuck! Unnhh!!”

“You’re perfect, Gwen, you’re so goddamn brave!”

It still really hurt, although maybe not as much as when they first started. Whereas before she’d had her eyes scrunched closed from the pain, her eyes were open, looking up at him as he was looking down at her. Her mouth was open, as she continued to moan. When she wasn’t moaning, she was panting, entirely out of breath. She hadn’t stopped gasping and moaning and crying out since they had started. He was out of breath too and his brow was covered in sweat.

“Oh gods! Your cock is so fucking big, sir! I can’t believe I’m really doing this! I don’t even know your name!”

He bent down to nuzzle her neck and breasts with his mouth. He suddenly began thrusting into her much faster and harder than before.

Gwen screamed and the scream became a continuous moan. Her hands gripped the bedsheets. Her body moved with his thrusts and it was all she could do to keep from banging into the bed’s headboard. She panted and moaned and little screams continued to escape from her mouth.

Later, she realized that he wasn’t going that fast at all, especially in comparison to her future customers. He could have fucked her much harder than he did. But at the time, it felt like he was going to make her lose consciousness.

“Oh gods, oh gods, oh gods! Oh oh oh oh oh ohhhh!” she moaned.

Suddenly, he stopped moving, with his cock buried entirely inside of her.

Gwen squinted up at him, confused.

“Why did you stop?” she asked. “Did you cum? I didn’t feel you cum. Shouldn’t I have felt it?”

“I was getting too close,” he muttered. “I didn’t want to cum, not quite yet.”

“Oh… When you’re ready to … start fucking me again, can you please go slower? I don’t know if I can handle you going so fast… Please?”

“Oh Gwen… I’m so sorry! I was going so hard with you for a moment there…I lost myself for a bit. Are you doing ok?”

“Yes…” she replied. She winced and then smiled weakly up at him. He quickly kissed her and resumed his slow strokes into her pussy.

“It still hurts,” Gwen added. “But I’m okay. How are you?”

“I’m in heaven, Gwen. You’re amazing. So fucking hot And so fucking beautiful.”

Gwen moaned in response, as he continued to fuck her. “Should I encourage him to cum?” she wondered to herself. “Or should I just let him go until he’s ready to cum?” She knew about dirty talk, although she’d never tried it with any of her boyfriends.

“Gwen, when I finish, where do you want me to cum?” he asked, as if reading her mind.

She was more than a bit surprised by his question.

“Sir…” she said quietly. “You can cum … wherever you’d … like. You’re in charge. I’m … here for your pleaaahh – pleasure!”

“I know,” he said, running his fingers down the outside of one of her legs and tucking a lock of hair behind her left ear, “but where would you like me to cum?”

She suddenly kissed him, genuinely moved by the question, as dirty as it was.

“Cum inside me, sir,” she whispered. “Cum inside my pussy.”

Looking back, it was like a switch was thrown in his brain when she said those words — her first time talking dirty. His thrusts picked up speed again, accelerating with each stroke into her.

Had she given him a wrong answer? Should she have told him to cum in her mouth? It still hurt, but gods, it felt good too! It was too much! She felt overwhelmed from all of the conflicting sensations! She felt like she was going to lose her mind, her body felt so hot all over! It was like her body was about to catch fire!

“Oh gods, oh gods, oh gods! Oh oh oh oh oh ohhhh!! Oh gods! Ohhhh!!” Her body jumped and writhed and squirmed beneath his and she surprised herself with a brief but intense orgasm.

“Oh fuck!” she exclaimed, gasping out the words. “That was fucking amazing. I just came! I can’t believe I just came…!”

Somehow, she expected that he would slow down again, but he didn’t. And she didn’t want him to do so! His current pace was really great, actually! She found that she didn’t want him to stop fucking her like this! She thought about attempting to get the words out. She didn’t know if she could. The orgasm had temporarily affected her speech!

“Besides, I don’t know if a brand-new pleasure girl should be telling the customer what to do!” she thought.

“Keep fucking me, sir!” she thought to herself instead. “Don’t stop, sir! Please don’t stop! You can fuck me as hard as you want, just please don’t stop! Don’t stop! Don’t stop! I want you to make me cum again!”

“Oh fuck! Fuck!” he groaned and she felt his body tense.

At the same time, she felt his cum flood her pussy. She felt his cock spurt inside of her multiple times, shooting his load into her; it felt like her pussy was going to overflow with cum.

“Oh my gods!” she moaned, looking into his fierce eyes. “There’s so much!”

As he came, he drove into her a few more times, obviously desperate to keep going.

Once it was clear that he’d shot all of his cum into her, he slowly withdrew his cock from her. Her tight pussy made a soft wet noise as it released his cock. He moved off of her and turned around so he was lying next to her.

“Wow…” Gwen murmured, fascinated by all the sensations she was feeling, all simultaneously. She felt like she was still floating on the high from her orgasm and she felt so hot from his having cum inside of her. She could feel some of the cum escaping out of her – a thoroughly strange sensation but she couldn’t deny how hot it felt.

“That was … That was the most intense experience of my life…”

“It was pretty fucking intense for me too, Gwen,” he said. “Wonderfully so.”

He reached out his arm to draw her close to him. She readily nestled up to him, resting her exhausted head on his heaving chest. She wiggled against him, enjoying the feeling of her breasts, her nipples still very much hard, against his body.

In that moment, absurdly, she actually felt love for this man who had paid for the privilege of taking her virginity. She didn’t know his name and didn’t know if she’d see him again after tonight, but a part of her loved him all the same. Perhaps it was just the aftermath of the orgasm affecting her brain.

“Did you have a good time, sir?” she asked, knowing very well that he had. But it was a question she’d always imagined herself asking after losing her virginity in a pleasure girl house.

“Of course. Absolutely. Five hundred percent. You were so incredibly amazing, Gwen,” he replied. “I knew it was going to be something extraordinary, but this exceeded my expectations. Thank you.”

“You’re welcome,” she said. She felt his cum continue to drip out of her aching pussy. She wondered how her pussy would feel when she was getting ready for bed after a full night of work. There would be more complete strangers with the full intention of penetrating her with their cocks. The thought was both exciting and terrifying.

He kissed her tenderly on the mouth.

“I’m sorry it hurt so much,” he said.

“That’s ok,” Gwen replied. “It was inevitable. I’m glad you were my first, sir. You were very courteous.”

He kissed her again. “I think you’re going to be a remarkable pleasure girl, Gwen. You’re so brave to have done this tonight.”

She blushed, ridiculously.

“I can’t believe I’m actually blushing in front of you! It’s not like you just took my virginity!”

They laughed quietly and then the two of them lay together in silence for several minutes. Then he moved very slowly out of bed, leaving her among the covers.

“I’m going to go take a shower,” he said, gathering up his clothes and putting on a robe provided for the customers. “I only wish I could see you again on your first full night of work. Hell, I’d settle for just getting to watch you at work with your first customers.”

She sat up in bed. “You’re welcome to come back that night,” she said. “I’d like to see you again… It’s an open house night, so I won’t have any appointments. I can arrange it, somehow, that you’re the first customer that I see?”

“And you won’t even have to tell me to spread my legs for you,” she added, giggling.

She was thinking that it would be nice to see a friendly face tomorrow night. He was less of a stranger than the other men who would be taking her upstairs in a matter of hours.

He laughed as well. “I would if I could, Gwen, believe me. But I live overseas and I’m headed back there tomorrow. Hopefully you’ll still be here next time I have to be here for business.”

“I hope so too, sir,” Gwen said.

He returned to the bed and kissed her goodbye.

“Have fun tomorrow night,” he said. “Promise me you’ll make all of your customers as happy as you made me tonight.”

“I’ll do my best,” Gwen replied.

The customer left the room, closing the door behind him. Gwen wondered if she would ever see him again.

[to be continued… far from the end].

Source: reddit.com/r/eroticliterature/comments/x1n8wp/the_pleasure_girl_f20_f42brothelloss_of