A whole week had passed since her aunt’s funeral and just two days since her ‘date’ with Eric. But two days was not enough for Sophie to come to terms with what she had done. She had lain awake at night, wondering how she could have been so wrong about herself. If you had asked her a week ago if she’d ever have sex for money, she would have cursed you. Now she cursed herself, called herself a whore or worse. A whore however, did not make as much money as she would by fulfilling her aunt’s last three contacts. A whore just got paid for sex, Sophie did so much more. ‘Fantasy fulfilment’ her aunt had called it. Sophie wasn’t sure whether that made it better or worse. If she was being honest with herself however, what bothered her most was not being paid for sex. It was the fact that she had enjoyed it; not just the sex, but the taboo feeling she got by being paid for it. She had two more contracts to fulfil and she did not feel guilty about that, she looked forward to them. She’d meet one of the other two clients after work today. ‘You should be ashamed.’ She told herself when she found out how wet and excited she got, just by thinking of meeting this stranger. But her self-scolding only turned her on even more. ‘Just wait.’ She said to herself. ‘They won’t all be like Eric. Who knows what this guy wants to do to you. And the contract is already signed, you have no way to stop him.’ This did make Sophie hesitate. What if the other contracts did contain some dark, perverted fantasies of these strange men? She could try to convince them to annul the contract. But that hadn’t worked with Eric, it might not work with the others either. Like this, the whole day running up to the meeting, her emotions bounced back and forth between shame, excitement and fear.
The second customer Sophie would service as her aunt’s replacement had invited her to his home. Sophie was quite nervous going to a stranger’s house, but since he already had a contract with her, there would be no reason for him to harm her in any way. The house she arrived at was quite ordinary, in the middle of a residential area. It made her feel more at ease, believing any man who lived here would be a normal, every-day person. When he opened the door for her, she was strengthened in that belief. The middle-aged man had short grey hair, wore faded jeans and a simple blue sweater. Sophie imagined he was a bit older than Eric had been. This did not make her feel uncomfortable, in fact, she thought it would be weird if one of her customers would be closer to her own age. The man shook her hand and invited her in. “Would you like a drink?” He asked her after guiding her to the living room. It was quite messy and Sophie had to clear away a collection of old magazines before she could sit down in the sofa.
“Yes, please.” She said. “Some water would be fine.” The man left her alone to get the drinks, which gave Sophie the time to look around the room. The furniture looked old-fashioned, like something the man had inherited from his parents or grandparents. There was an old scratching post in the corner of the room, but no cat around. A laptop stood half-opened on the coffee table; Sophie fought the urge to look at what the man had been doing before her arrival.
“So, what I this about?” The man asked when he returned with two glasses of water. He looked slightly nervous, just like Eric had been. These men were used to secrecy when dealing with her aunt. He did not understand Sophie’s role in all of this.
“I’m afraid I have some bad news.” Sophie said. She had again chosen to give the news in person. “My name is Sophie and a little over a week ago, my aunt passed away.” She paused for a moment. “You know my aunt of course, because you had a contract with her.”
The man hesitated. “I’m sorry for your loss.” He said. “I’ve known your aunt for quite a while. I might’ve been just one of her customers, but I believe we were close regardless.”
Sophie nodded. “Of course.” She said. “I’m sorry to be the bearer of such bad news.”
The man smiled sadly. “It’s okay.” He said. “My name is George by the way.” He hesitated again. “Do you know, what kind of work your aunt did?”
“Yes.” Sophie said. The man blushed. “That’s the other reason I’m here. You still have an open contract with my aunt and we need to discuss how we’re going to handle that. You see, after my aunt passed away, I took over the company.”
The man stared at her open-mouthed. “You took over?” He asked. “How does that work?”
Sophie blushed slightly. “Well, you contract wasn’t really with my aunt. It was with her company. Now that I have inherited the company, it is my duty to fulfil any contracts that are still open.”
The man was smiling now, probably already imagining Sophie doing whatever it was he had paid her aunt for. “So, you mean you take her place?” He asked.
“Well, that depends on you.” Sophie said. This was the point where she should convince him to annul the contract. But she didn’t really want to. The fear she’d felt before was diminished by how normal and safe she felt around this simple man. Only the excitement remained. “You have the right to break the contract because I’m not the original person that made up the contract. You can claim my lack of experience as a legal reason to demand your money back.”
The man was still smiling. “But if I don’t.” He said. “You will take your aunt’s place and fulfil the contract?” He asked. “Why don’t you break the contract yourself?”
Sophie blushed. “Unlike you, I don’t have an acceptable motive to break the contract.”
The man frowned. “So you have no choice?” He asked. That doesn’t seem very fair.”
“Well, I did not have to take over the company of course.” Sophie explained. “I just had to make a choice to inherit what would be left after disbanding it, or take over the company and with it the running contracts.”
The man was smiling again. “So you knew you would have to fulfil the contracts. Or did you hope you could convince me to ask for my money back?”
“I hoped I wouldn’t have to do anything.” Sophie admitted.
The man smiled fondly. “It’s okay. If you want me to annul the contract, I will. I’m not going to do anything to you that you don’t want me to.”
“But I don’t know what you want to do.” Sophie said. She blushed, it was hard to admit to herself she had come to enjoy these things; it was even harder to admit it to a stranger. “If it’s not too bad, I wouldn’t mind I guess. But my aunt kept all the contracts locked away and I don’t know what’s in them.”
The man clapped his hands. “Aha, of course! I’ll get my copy and let you read it.”
Sophie blushed deeply. The man had given her the choice; she could have just accepted his proposal and this contract would be done with. It had been her own damn curiosity that had gotten the better of her. She wanted to know what was in that contract. ‘Just read it.’ She told herself. ‘You can still back out later.’
When the man returned with the contract, Sophie was glad she’d asked to read it first. This contract was nothing like the one she had done with Eric. This wasn’t a date; it was a perverted roleplaying plot. There was not much sex involved, but beside the degrading role she’d play; he wanted to spank her as well. Nervously Sophie looked up at the man she had thought was so innocent. Behind that every-day face some perverted desires were hidden. “I’m not sure I want to do this.” She said.
The man sighed. “I feared you might say that.” He said. “Have you done any of the other contracts?”
Sophie blushed. “Just one.” She said. “But that was just sex, nothing special.”
“How did it make you feel?” He asked.
“Well, I was nervous at first.” Sophie admitted. “But I kind of liked it in the end.” She blushed deeply, wondering why she was telling this stranger all of this.
“Maybe you’ll come to enjoy this as well.” The man said. “Many women enjoy spanking as a sexual activity. It can be quite arousing.”
Sophie bit her lip. “What about the roleplay?” She asked. It wasn’t really the spanking that bothered her most. Like most young women she had a healthy fascination with some kinkier fantasies.
“Don’t tell me you’ve never had fantasies like that.” The man said. “The reason I like to roleplay them is because that’s the only way to ever experience them. I would never actually do those things with someone who wasn’t pretending.”
Sophie blushed. Had she ever had such fantasies? It had been a long time since she’d been in a situation like the girl in this man’s fantasy. She might have fantasised about these things however. Perhaps that’s why she found it so disturbing in the first place. “I guess roleplaying these fantasies with my aunt helped you deal with them in a healthy way.” Sophie said hesitantly.
The man smiled broadly. “I guess you could say that. So, would you mind helping me as well, Sophie?” He asked.
Sophie nodded nervously.
“Great.” The man said. “Do you have time tomorrow after work? Just show up at the address that’s in the contract. I’ll send you a copy.”
“Sure.” Sophie said. She did not understand what had changed her mind, but somehow agreeing to help him fulfil his fantasies, had turned her on greatly. “I’ll see you then.”
The following day, Sophie took a quick trip home after work. Her aunt had owned a huge collection of outfits to wear for her work and Sophie had gone by her house to pick one after her meeting with George. Today, she pulled on the knee-high white stockings, the white cotton panties, the short tartan skirt, the simple white blouse and the dark-blue tie. Looking in the mirror she saw a girl that had outgrown her school-outfit: the shirt just a bit too short, the blouse too tight around the bust. Sophie wasn’t sixteen anymore of course. On a woman her age the outfit wasn’t just cute anymore, it was sexy as well. She wondered for a moment how it would have looked on her forty-something aunt. She blushed. George must love the fact that she would replace her, at least Sophie looked slightly passable as a naughty schoolgirl. She’d put her hair in a braid and removed all her make-up to make the effect even more believable. Sophie used to own an outfit very similar to this one. Putting it on had reminded her of her own time in school. George had been right; she did have memories of some very inappropriate fantasies during that time.
Sophie put on a long coat before leaving, she couldn’t bear anyone seeing her in that outfit. She took public transport to the school building where George worked. It felt very wrong that a man with fantasies as these actually worked at a school. But as long as they were just fantasies – something he roleplayed with grown women like herself – it shouldn’t pose a problem. The building was empty of course, all the other teachers and the students had gone home. The door was open like George had promised. Nervously, Sophie made her way through the empty hallways. She hadn’t been to a school in years, but she remembered the smell. She followed George’s instructions to a classroom where a light was still burning.
“Come in.” George’s voice sounded after Sophie knocked on the door. “Take a seat, Sophie.” He said. “You’re the only one in detention today.”
Sophie blushed and took a seat on the first row. she couldn’t remember ever have gotten detention when she’d actually gone to school still. It was an odd experience.
“I’m sir Reynolds.” George said. “You don’t get any classes from me, but I’ve heard from my colleagues that you’re an exemplary student, Sophie. Good grades, perfect attendance, good behaviour.”
Sophie nodded. “Yes, Sir.” She said. Having read the contract, she knew where this was going.
“So how did a student like you end up in detention?” George asked.
This part was her responsibility in the roleplay. George wanted her to come up with it herself. He didn’t know yet what he was going to spank her for. “I just tried to be helpful, Sir.” Sophie said, pretending to believe there was still a way to convince the teacher she was innocent. She was playing a role after all.
“Who were you trying to help, Sophie?” The teacher asked.
“My classmates.” Sophie said. “I just made some of their homework for them.” She blushed. “I might have made them pay me for it too.”
The teacher raised an eyebrow. “You might have?” He asked.
Sophie blushed. “I did, Sir.” She said. Just like she had accepted money for sex in real life, she now pretended to have accepted money for something she shouldn’t have done. She hoped the spanking would feel more real if it was for something similar as what she’d actually done. Not that she wanted a spanking of course, not really.
“Not only is it wrong to ask for money from your classmates, Sophie.” He teacher said. “You’re also not helping them. If they don’t do their own homework, they’ll never improve in class. All you’re doing is holding them back and taking advantage of them.”
Sophie blushed. “Yes sir. I realize that now.”
“Well, it’s a bit too late now, isn’t it?” The teacher said. “Normally in detention we make the students do their homework or give them extra assignments. Seeing how you seem to like doing homework and your grades are already very high, that won’t do for you. We’ll have to think of something else.”
Sophie bit her lip. She knew exactly what that something else was going to be of course; but the innocent school girl she was playing did not. “Like what, Sir?” She asked.
“I think a girl like yourself needs something different.” The teacher said. “Something that will remind her thoroughly of her behaviour so that she will never do it again. Something more old fashioned than homework or writing lines. I’m sure I’ll never have to see you in detention again after a good firm spanking.”
Sophie blushed deeply, partly played; but partly genuine as well, as she imagined this spanking to be for her recent real-life behaviour as well. “But you can’t do that, Sir.” She said. “They don’t give spankings in school anymore.”
“For you, I’m willing to make an exception.” The teacher said. “You’re going to come to the front of the class, accept your punishment and then you’ll be free to go home.”
Sophie stood up from her desk and walked to the front of the empty classroom. George was standing right beside the large, wooden teacher’s desk. “I won’t do it again, Sir.” She promised.
“I sure hope not.” The teacher said. “Now, bend over my desk, please.”
Sophie blushed as she stood in front of the wooden desk. It was quite high, up to her hips. She had to stand on her toes to be able to bend over it, her bottom was up high in the air. The skirt of her schoolgirl outfit was just long enough to cover her behind, nothing more. It felt surreal standing there like this. She was about to let this man spank her. She was letting him do it because he had paid her; and she was letting him do it because she let men like him pay her for things like this. She suddenly doubted her idea would work. How was she going to learn anything from this spanking, if she was at the same time doing what she was getting spanked for in the first place?
George lifted her short skirt and folded it across her back, exposing her cute bottom to the empty classroom. “I’m happy to see you’re wearing regulation panties, Sophie.” He said. “But unfortunately for you, that means they have to come down as well, they offer too much protection the way they cover your entire bottom.”
Sophie blushed deeply as the teacher pulled down her panties, all the way to her knees. She hadn’t felt this shy around Eric, but by the time he had undressed her, she’d been deeply aroused and been playing his girlfriend for a whole evening. George was still a stranger and pretending to be her teacher, not her boyfriend. Being exposed to him felt a lot more embarrassing; and exposed she was, bent over his desk the way she was.
George softly stroked her bottom. His fingers gently probed her flesh, exploring between her cheeks and even feeling her pussy. Sophie was sure no schoolgirl had ever been spanked like this; not on their bare bottom and definitely not touched so intimately. It was just a fantasy however, and like George, the fantasy deeply aroused her. It was true, sometime long ago, Sophie had fantasied about being at her teacher’s mercy like this. When George smacked her bottom firmly, she moaned softly in reply. Slowly George smacked her bottom, firm full-armed swings. Sophie moaned deeply as her behind grew warm and sensitive. A soft sting built up as George placed a hand on her lower back to hold her down on the desk. Firmly in his grasp, the speed of the spanking increased, the pain in Sophie’s bottom building. George had been right, this could be enjoyable, but the sting quickly built up and Sophie found herself squealing and moaning in pain. The combination of pain and excitement made it hard to think, she found herself in a new, different mind-set, completely under George’s control. She knew that this naughty schoolgirl would do anything her teacher desired of her.
Sophie moaned deeply as George paused the spanking. He rubbed her bottom firmly, his fingers digging between her lips, feeling how wet she was. “Are you learning something, young lady?” He asked.
“Yes.” Sophie whispered. She was learning, learning to enjoy a good spanking.
The teacher smacked her behind. “Yes who?” He asked.
“Yes, Sir.” Sophie said. She no longer cared that she was getting paid for this spanking. This was exactly what she deserved for being a naughty girl that accepted money for sex. The fact that she was doing it again didn’t change that. It just meant she deserved it even more.
George spanked her again. Even harder this time. Sophie squealed and then cursed softly. Her bottom was on fire and she was kicking her legs uncontrollably. Her cheeks bounced beneath the palm of George’s hand, they coloured bright red. Tears were rolling down her cheeks by the end of it, from the pain and embarrassment for how naughty she’d been. But still, deep inside she knew she would probably do it again. There was still a third contract. She deserved this and even more.
When her teacher stopped the spanking again, Sophie reached back to soothe her burning bottom. She lay panting on his desk, unable to catch her breath.
“I’m going to make sure you’re never going to forget this lesson, young lady.” George said. “I’m going to continue this right away with my ruler.”
Sophie blushed. Part of her wanted not to say anything; to just lay down and accept her punishment. She was curious about the ruler and what it would do to her. But that was not what was in the contract. “Please, Sir.” She begged. George had already picked up the long wooden ruler and placed it against her bottom. He wouldn’t use it of course, that was not in the contract. “I learned my lesson, anything but the ruler, please.”
George put the ruler away and walked around the desk, sitting down in the teacher’s chair. “Stand up and come over here.” He said. Sophie did as she was told, walking around the desk and leaving her panties behind on the floor. “Are you going to be a good girl and do exactly as you’re told, Sophie?” George asked her.
“I’m going to need you to prove that to me, otherwise I’m going to have to use the ruler, do you understand?”
“Yes, Sir.” Sophie said.
“Very well then.” The teacher said. “Get on your knees.” He unzipped his trousers and took out his hard, erect cock as Sophie knelt down in front of him. “Suck it.” He said.
Sophie blushed. This was exactly what she’d been spanked for. George didn’t know that of course. He thought they were just roleplaying and her role right now was to suck his dick. He’d paid her for that. Sophie took him in her mouth. She could feel his heartbeat on her tongue, taste his excitement. At that moment she decided, if this was what she had to get spanked for, it was worth it. All the pain in her bottom, the embarrassment of bending over his desk; the shame in accepting money for sex; it was all worth it for this feeling of arousal, the kinky pleasure in doing something forbidden. She sucked George’s cock until he was moaning and grunting, until his juices erupted into her mouth and then she sucked out every last drop of it.
“Good girl.” The teacher said. “I see you have learned your lesson.” He waited for a moment while Sophie stood up, smiling slightly as he watched her rub her sore bottom. “Better get dressed now. Detention is over, you should head home straight away.”
Sophie blushed scarlet as she got on the bus, relying on public transport again. She imagined everyone would be able to see what had happened to her. Her coat covered her embarrassing outfit, but – like her skirt – it was short. The bus seats were not very soft and she found herself squirming in her seat. She wasn’t going home straight away either, that wasn’t what George had meant. There was still a part of the contract to be fulfilled. It didn’t take long until she arrived at George’s house. He would be there already, using his car he had beaten her to it. She had the keys to the house. “I’m home.” She said as she entered.
“You’re late.” George said as she entered the hallway. “What happened?”
Sophie blushed. “I had to stay after school… In detention.”
George frowned, pretending to be upset. “What did you do that got you into detention, young lady?”
Blushingly, Sophie told the same story again, this time to the man who was pretending to be her stepfather. The teacher roleplay had been bad, but this was even worse. Sophie did not understand how anyone could have sexual fantasies like this one, she surely never had. There was nothing she could do about it now of course; it was certainly not worth it to back out now.
“Well, you certainly deserved to be held after class for what you did.” Her ‘stepfather’ said. “I can’t believe you’d try to sell homework to your classmates.” He paused for a moment. “You know the rules, young lady. Get your stuff, whatever punishment you got at school you get at home as well, you better start writing.”
Sophie bit her lip. “I didn’t have to write lines.” She said.
George raised an eyebrow. “No? Then what do they have you do in detention these days?”
Blushingly Sophie raised her skirt like the contract told her to. The redness of her cheeks was visible even through the white cotton panties she wore. “I got a spanking.”
George laughed. “Well, I guess, some teachers still know what to do with naughty young girls like yourself.” He took Sophie by the wrist and pulled her into the living room. “Get over here.” He said.
Sophie struggled. “No, you can’t.” She said.
“I can and I will.” George replied. He pulled her over his lap on the sofa and flipped up her dress. “The same punishment you got at school, you’ll get from me.“ The white panties were quickly pulled down and George smacked her already sore, red bottom. Sophie moaned and begged, but the pain in her behind was quickly renewed as George relentlessly spanked her behind.
The intimacy of the living room and George’s lap instead of the hard, wooden desk, turned her on greatly. Sophie ignored the fact that George was pretending to be her stepfather, instead she tried to enjoy the spanking. It hurt a lot, but somehow less than before. Without being bend over and with her bottom already used to the punishment, the pain was more tolerable. While the smacks kept coming and Sophie moaned and squealed in pain, she was at the same time deeply aroused, wet with excitement for the things she’d done and experienced today. When George finally stopped and sent her to her room – a guest room they were pretending was hers – she went eagerly. Alone in her room, she dropped on the bed. She heard George come up the stairs as she was rubbing her poor, sore bottom. She heard him open the door to her room, but pretended she didn’t. George was pretending to be a dirty old man spying on his step-daughter. In Sophie’s mind he was just a stranger, sneaking a peek at her while she soothed her embarrassingly red bottom. Sophie did not pretend to be excited from her spanking, she was wet and deeply aroused; not for the reasons George was imagining, but neither of them really cared what the other was thinking at this point. Sophie rolled on her back. She softly stroked the lips of her pussy and pushed a finger inside of her. As the last part of her contract, Sophie would masturbate while George looked through the crack by the door, spying on his ‘stepdaughter’ who was secretly aroused by her spanking. Ignoring George’s perverted fantasy, Sophie had no need to fake her excitement. It wasn’t long until she was gasping for breath, her body shuddering in climax as George looked on.
“Can we make another agreement?” George asked. It had been nearly an hour since Sophie had fulfilled her contract. George had let her use his bathroom to clean up, but her bottom still hurt quite a lot.
“No, sorry.” Sophie said. “I’m just fulfilling the last contracts form my aunt. “
“Really?” George asked. “After today I thought you might change your mind. I’m sure you enjoyed yourself, didn’t you?”
Sophie hesitated. “Well, yes.” She said.
“Then why not?” George asked. “You’re really good too, very genuine in your reactions. Even better than your aunt was.”
Sophie blushed. Of course she had seemed genuine, she’d been truly aroused and truly felt she deserved the spanking he had given her. “I just don’t feel comfortable doing this kind of thing.” She said.
“Well, doesn’t that make it more fun?” George asked. “Besides, you won’t be bound by previously made contracts like this one. If we make a new one and you don’t like it, you don’t have to sign it, or we can change it so you do like it.”
Sophie bit her lip. They could make a contract where she didn’t have to pretend to be his stepdaughter. She didn’t mind the student-teacher thing that much and the spanking certainly had been interesting. “I don’t know.” She said. “I’ll have to think about it.”
George smiled. “I’m sure you’ll be able to come up with a roleplay that works for the both of us. Personally, I’d love to spank that cute bottom of yours anytime, no matter what the story is behind it.” Sophie blushed deeply. “Just let me know when you’re ready.” He said.
Sophie nodded. “I’ll think about it.” She promised.