2 comments/ 47577 views/ 36 favorites Good Girl Sara By: HeyAll It was her first week as a newly hired assistant editor for a major fashion magazine. A strong resume and plenty of internships helped Sara land the coveted job only a few years after graduating from a prestigious university. She was close to her dream job of becoming a staff writer. Writing was her calling in life. She was certain of that. Both of her parents were writers; her dad wrote stage productions, and her mom wrote children's books. As always, Sara dressed sharp. She had to, since she was working for a place that revolved around fashion. Her personal philosophy on style was to be classy, yet sassy, while remaining professional. That consisted of heels, stockings, office skirts, and buttoned up tops. Sara put her purse down on the desk and leaned back in her chair, breathing a sigh of relief. It was her goal to show everyone that she was always on time, and that she worked harder than everyone else. Reputation was very important to her. "Busy morning?" Chloe asked from the other desk. The office area was loose and relaxed. It was common for people to be walking around and having normal conversations. From the moment Sara first landed the job, Chloe had been her close friend. Chloe was almost like a mentor, even though they were a few years apart in age. But Chloe had been there a lot longer. "I don't think I'll ever get used to living in the city," Sara replied. "My god, it's crazy." "You'll get used to it. We all do." *** They usually ate lunch at the same place. A small Mexican restaurant where people waited in line for something quick to be served. After they got their food, they sat at an outside table under the sun. "I think the boss really likes you," Chloe said while eating. "He usually doesn't give a shit about the new employees." Sara smiled and shook her head. "We said 'hi' a few times. That doesn't mean anything." "Yeah, but he usually doesn't say 'hi' to lower level employees. Especially assistant editors like us." "I was the one who said 'hi' first. What's he going to do? Be a giant prick and ignore me?" Chloe shrugged and took another bite of her lunch. "I don't know. I just think he treats you better than most of the new employees. I'm good at reading body-language. I know all about this stuff." "Well, hopefully I can use it to my advantage then." "Got anything in mind?" "I want to be a staff writer someday," Sara replied. "For this place, that'll take years and years. There's a long line of talented writers who are dying to work for Mr. Halpern." "But it's all about who you know right? Maybe I'll drop off some writing samples for Mr. Halpern to look at." Chloe smiled, "Yeah, you and a hundred other people." "How many job solicitations do you think he gets every day?" "I don't know. But I hear it's a lot. He's got crazy connections in the fashion and magazine world. I've heard it takes years to become a staff writer. And that's if you're lucky, and if you're an extremely good writer. Halpern has crazy standards, as you already know." "Oh..." "Have you thought about applying to become a writer somewhere else?" Chloe asked. "It's crossed my mind. But I'm already an employee here. This company is my ideal place to work, without a doubt." Chloe gave a sympathetic nod. "Like I said, Mr. Halpern seems to like you. Maybe you'll get special treatment." There was a quiet sadness on Sara's face. She nodded and accepted the fact that she was a small fish swimming in a big ocean. "Look, can you keep a secret?" Chloe asked. "Sure I can." "I mean, this is a big freaking deal. If I tell you something, do you swear to never tell anyone that I've told you?" Sara's interest was peaked. "Yeah, I swear." "I'm serious. You can never tell anyone I've told you this. Ever. Until the end of time." "Just tell me already," Sara replied, annoyed. "Alright, well, before you started working here, my old supervisor was an editor here. A big time editor. She was fired for embezzlement of corporate cash. It's a long story, but she was bitter about the whole thing. She says she didn't do it. Anyway, she told me a secret one night." Sara leaned it. "I'm listening." "Apparently, there's something called the Good Girl's Club in the fashion industry. It's super secretive. And it's highly exclusive." "What do they do?" "They give each other preferential treatment," Chloe explained. "You know, it's like if you want a high profile job at a magazine, or as a reporter, or even as a model, you'll go to the front of the line." "How come I've never heard of this?" "Like I said, it's super secretive. Apparently, the initiation is providing sexual services." "Sounds like a conspiracy theory," Sara replied with a skeptical tone. "You even said, the person who told you this was bitter. Maybe she was just spreading rumors to get back at the company." "Maybe. But she sounded pretty convincing. I'm rarely ever wrong in judging human emotions." They went back to eating. Things were quiet for a while, especially as Sara processed the strange rumor of a private club. "Do you really think it's true?" Sara asked hesitantly. "The whole club thing. It makes it easier to get a promotion, right?" Chloe smiled, "I don't know. Why don't you ask?" *** The managing editor of the magazine, Mr. Halpern, was a notoriously intense boss. He had a sharp demeanor and was quick to scold his employees. He was in his mid 40's, stylishly dressed, and highly intelligent with an overly ambitious attitude. That was how he became the managing editor of one of the most influential fashion magazines in the world. He had been informed by his secretary that someone was waiting for him in the lobby. Someone without an appointment. He had extra time, so he agreed to the impromptu meeting, which he normally didn't do. Sara entered the room with a blatantly forced confidence. The confidence wasn't fooling anyone. She was a nervous wreck deep down. "What's your name again?" he asked, standing up. "Sara. I'm a new assistant editor here." They shook hands. "Have a seat." When Sara sat down in front of Mr. Halpern's desk, her eyes briefly surveyed some of the accolades and awards which were displayed. She even caught glimpses of some of the pictures on his desk, which included photos of Mr. Halpern with celebrities, big time fashion models, and even a few politicians. "Just so we're clear, I normally don't do this," he said. "Do what?" "Meet in my office without an appointment. I'm a very busy man. But, since you're new, I'll make an exception." "Thank you so much," she smiled nervously. "Did you come here to sit down? Or did you have something in mind?" "Well, I'm a new assistant editor here. However, my dream is to eventually become a writer for this magazine. You know, like write articles, things like that." He gave an annoyed look. "I know what a magazine writer does. You don't have to explain that to me." "Sorry. I'm a little nervous." "Don't be." Sara quickly took a deep breath. "Anyway, my goal is to become a fashion writer. I'd like to cover new trends, report on fashion shows, give advice, and so forth. The manager who hired me said that I have talent." "This city is filled with people who have writing talent," he replied coldly. "What makes you so special?" For a split second, Sara completely froze. The boss was a much bigger prick than she had expected. Visiting the boss might have been the biggest mistake of her life, she thought. When she finally realized that she had a stupid look on her face, she tried her best to snap back to reality. "Maybe I'm not as talented as others," she quickly backtracked. "But I'm loyal to you, and this company." He gave a long cold expression. "If you're not as talented as others, why should you still be employed here? Maybe I should fire you right now?" Signs of perspiration formed underneath Sara's shirt and her forehead. "I...I don't know." "Give me a reason why I should keep you employed." She gulped. And in a moment of complete desperation, she threw the hail mary pass, almost without thinking. "I know about the Good Girl's Club." He raised an eyebrow. "Do you?" "Yes," she replied, thinking it saved her job. "And what exactly do you know about it? Tell me." "I know that it involves a lot of people in the fashion world. And I know that it helps with job connections." Mr. Halpern stood, and Sara was unsure of what to do. For a moment, he didn't say anything. He turned around and looked through the window towards the outside view. Thinking. "Are you interested in joining?" he finally spoke. The question had caught Sara completely off guard. She really had no idea what the club was, let alone being prepared to join it. "Yes," she blurted out, unsure of what would happen next. "Very well. But first, you have to tell me how you found out. Who was your source? Who leaked the information?" The perspiration in Sara's body continued. She could feel the tiny beads of sweat begin to form underneath her shirt. "It was something I overheard." "I don't believe you Sara," he replied confidently. "Tell me the truth. Or else you're fired." She gulped. "What's going to happen to the person that told me?" "It depends." "On?" "The circumstances. I'm not a cruel man. I can be a little strict, but I try to be fair." "Do you promise you won't fire her?" Sara asked. He thought for a few seconds. "Fine. Her job is safe. And I won't mention this conversation to anyone." "Chloe told me about it during lunch. We were talking about my desire to be a writer here, and she told me. She thinks it's a rumor from a former boss. She doesn't know if it's real. I swear. Please don't fire us." Mr. Halpern turned around to face Sara. "Both of your jobs are safe," he said. "As long as this remains private." Sara breathed a sigh of relief. "Oh thank you." "I like you Sara. I see great potential in you. That's why I'm willing to accommodate you. However, confidentiality is a big part of this arrangement. If I can't trust you, then you cannot join. Understood?" "Yes, I understand." "Now go. Tell your friend Chloe that the club was just a big nasty rumor. Nothing more. She can never know. Tomorrow, come to the main conference room, first thing in the morning. We have a few things to discuss." "Okay. Thank you so much for this opportunity, Mr. Halpern." "Don't thank me. You haven't passed the initiation yet." A realization had sunk in Sara. Judging by the look on Mr. Halpern's face, she knew she was in for a few surprises. *** That night. Sara laid on her couch watching Game of Thrones. Despite the nudity, treachery, and violence, all Sara could think about was the meeting with Mr. Halpern. It had been the most awkward moment of her life. She wondered where the next meeting would lead, and what they were going to discuss. She also felt bad about lying to Chloe. She told her office friend that Mr. Halpern admonished her for even suggesting such a thing. But it was for the best. If Sara didn't lie to Chloe, then both of them would have been fired. Before long, her eyes were closing before the episode ended. She turned off the television and went to the bedroom, making a mental note to finish that episode later. The stresses of the day had left her exhausted beyond belief. *** Early morning. The conference area was well known. It was a long room which was frequently used for high level meetings. It was where all the major decisions were made. It was where all the big deals were closed. It was even the place where big name celebrities and models were courted. Sara took the elevator and went to the proper floor. Surprisingly, it was mostly empty except for a few people and a receptionist. The floor wasn't hard to navigate. She followed the signs on the wall and headed towards the conference room, where the door was slightly open. She peeked inside and saw Mr. Halpern standing alone. After a few knocks on the door for courtesy, Sara entered. "Close the door," he said. Sara closed the door, and they were alone. There were a few pieces of paper placed neatly on the table, along with a pen. "What's that?" she asked. They were still far apart, and Sara walked towards the boss. "They're a few legal documents for you to sign, if you want. Don't worry, everything is written in plain English, so it's simple to understand. I'm not trying to trick you." Sara's eyes glanced down at the separate documents. The font was large. Each page only consisted of one or two paragraphs. The writing was in basic form, and there was no legal terminology. "What is it for?" she asked, still glancing at the pages. "Nondisclosure agreements. It says that everything that happens between us remains private. It's really that simple. I'll give you time to read it. We can continue this conversation tomorrow if you decide to think about it." After a few more seconds of glancing through the pages, Sara grabbed the pen and quickly signed her name on each of the documents. When she finished, she put the pen down and looked at her boss. "There. It's done." "Are you sure you want to go through with this?" he asked. "I'm sure. My dream is to become a writer here. Whatever you want to discuss, I won't tell anyone. It'll be our secret." "And Chloe? Will you tell her?" Sara shook her head. "I told her yesterday that the club thing wasn't true." "Did she believe it?" "She did." Mr. Halpern reached over to collect the papers. Then he folded it and placed it neatly inside of his jacket pocket. "So, you wish to join the infamous Good Girl's Club. But you don't know exactly what it is. How interesting." "I'm very motivated to succeed," she gulped. His eyes looked over her body. He noted that she was well dressed, particularly for that day. He liked that she had dressed extra sharply for him. "Slid your panties down. Give them to me." Those words caused Sara to reflexively tighten her muscles. "Why?" she asked. "Because it's part of the initiation. Do you want to join or not?" "Of course I do." He looked down at her skirt. "Then show me you're interested." The look in his eyes was serious, and so was the tone in his voice. Sara knew that there was no way around it. It was humiliating, especially as they stood by the window. There was a large office building nearby. Anyone from the other building could have easily looked to see Sara undressing. But it was worth the risk. Sara reached below and slid her panties down, trying her very best not to expose any of her private parts. Once the panties were around her ankles, she stepped out of it, and she held the panties in her hand. "Give them to me," he said with his hand extended. She reached over and placed her panties in his hand. "Now turn around," he added. Model yourself for me. You look great in that skirt." "I'm not very good at modeling," she admitted. "Just give it a try. I'm not going to criticise you." With a hint of embarrassment, Sara gave a slow and awkward twirl. But not too hard. She didn't want her office skirt to fly up. It looked painfully bad, and any professional model would have laughed at Sara's horrendous moves. "Was that okay?" she asked, hoping it would be over. Mr. Halpern sat down in a leather chair and leaned back, which was a clear sign that they weren't even close to being finished. "You have a cute bottom," he complimented. "Turn around and show me the back of your skirt." Sara listened and turned around. She faced the other end of the room thinking it was less embarrassing since she didn't have to look at her boss anymore. She prayed that no one in the other office building was looking at the awkward conference room encounter. "Now pull your skirt," he said. "Pull it forward so that I can see the shape of your rear end." Her fingers wrapped around the bottom of her skirt, then she pulled it forward, giving her boss a clear outline of her bottom. She wondered what the shape looked like. She wondered what Mr. Halpern must have been thinking. "Do you like it?" she asked, then immediately regretting it because it sounded like she was enjoying the moment. "You have a lovely figure. I've noticed it since the day you started working here." "Thank you." Sara was still holding her dress to reveal the shape of her rear end. She held the position, wondering how much longer she would have to do it. "Now lift your skirt," he said. Sara tried to think of the quickest excuse possible to get out of the situation. But she couldn't think of one. "I'm not wearing any panties," she said, as if that would somehow help. "I know. It's finally time I see your bottom." "Why?" "Are you questioning me?" "No." "Then do it," he said. Sara lifted the dress, praying that no one in the nearby office building was looking. She was too scared to check. Even though the room was set to a comfortable temperature, Sara could still feel the cool area on her private parts. In a strange way, she could feel Mr. Halpern's eyes roaming across her round shapely bottom. "Very nice," he said. "That was excellent. You may cover yourself now." She quickly pulled her skirt down, then turned around, almost too embarrassed to look him in the eyes. "That was weird," she said. "Don't be ashamed. You have such a beautiful backside." She blushed. Feeling kind of proud of her hard-earned body, especially her toned legs. "Thanks. I do a lot of aerobics at the gym." "Have you enjoyed this?" he asked, eyebrow raised. "Do you like being a secret exhibitionist for me?" She gestured to the window. "Who knows who else might be watching." "Ignore them," he smiled. "Just focus on me. Did you enjoy showing your beautiful rear end to me?" "It was interesting. Am I part of the club now?" "What's the rush? The initiation process is usually quite lengthy. And for good reason. Think of all the perks you'll be receiving." Sara nodded. "What else do I have to do?" "Don't wear panties in the office anymore. I like you better without panties. Also, try wearing smaller skirts. Show off those incredible legs." "But...people would notice that I'm not wearing..." "Don't worry about anyone else," he replied sharply. "The only opinion that matters is mine. Understood?" "Yes." "I might check at any time. And if you're wearing panties, the deal is off." She nodded. "Okay." "You'll be receiving further instructions soon. And I expect total compliance. If you do this, then you'll be rewarded for your good deeds." "Thank you sir." Mr. Halpern put the panties in his pocket. "You can go now. I'm keeping your panties as a souvenir." After another nod, Sara left the conference room. When she left, she could still feel her boss's eyes glaring at her bottom. It was strange walking down the hall without any panties on. She felt exposed. A wrong move could expose her private parts by accident. It was an unusual rush. *** Days passed. Then a week. Then two weeks. Sara became restless with her boss. She tried to muster the courage to go talk to him. But she figured it would only lead to more humiliation. Soon after their first 'meeting,' Sara began to doubt the whole thing. The Good Girl's Club was probably a dumb rumor, and Mr. Halpern was sleazy enough to take advantage of a naive young employee, she thought to herself. What a jerk. Nevertheless, she continued to follow the instruction. After their meeting, she stopped wearing panties to work. It was a feeling she quickly became accustomed to. It was thrilling and nerve wracking at times. Other times, she had completely forgotten about it. The worst moments were outside the building. If there was a cool breeze, she felt the air brush against her vagina. She worried that the wind would blow her skirt up, then everyone would see her privates. Good Girl Sara Sara had also bought a new set of office skirts. Same style. But a few inches shorter. Her old skirts were knee length. Her new skirts were just above the knee. She liked the sexy look of her new skirts. But she was annoyed by the catcalling on the street, and the gawks from her male colleagues. She wondered if her female colleagues had lost any respect for her, but then again, they worked for a fashion magazine. *** Sara was hard at work editing someone's article. By her standards, the article was shit. It pained her that she was a much better writer than the person she was editing for. Even worse, Sara was obligated to fix the article, and the untalented writer would receive all the credit. Deep down, Sara figured that the author was probably blowing someone at the management level. It was the only rational explanation. With a few seconds of daydreaming at her desk, Sara wondered if she would also blow someone for a chance to become a writer for that magazine. "Busy?" a woman's voice said. Sara snapped back to reality and saw Ellen, the chief financial officer for the magazine. Even in her 50's, that woman could still outstyle most of the younger employees, any day of the week. "I was just taking a break from editing. My eyes were getting tired." Ellen smiled, "I know what that's like. Believe me, staring at numbers all day can be rough." "I know what you mean." "You're probably wondering what I'm doing here." "Yeah, I don't think we've formally met before." "That's because I don't associate with assistant editors," Ellen said with an arrogant smirk. "However, Mr. Halpern has told me all about you." The mood of the conversation suddenly changed, and Sara's eyes widened. "He has?" "Oh yes, everything," Ellen replied. "I've got an important meeting soon, but I wanted to personally deliver something. So here it is." Ellen handed Sara a small package. It was an unmarked plain box, which was fairly light in weight. "What is it?" Sara asked. "Open it later. No one can ever know. Remember, you've signed several confidentiality agreements." Sara held the package and looked at Ellen with a surprised expression. "Are you part of the...you know...the good..." "I don't discuss rumors with new employees," Ellen winked before leaving. The awkward moment was over when the chief financial officer walked away. Sara was left holding the package. She knew that Chloe would be returning at any moment, so she got up and headed to the bathroom. Sara went inside the bathroom stall and sat down. She opened the box to see a small 3-inch oval device, which was smoothly shaped, alongside a small container of lubrication. There was a letter underneath. She picked it up and read the note: Sara, I've been admiring you from a distance. So far, you're doing an excellent job. As for the contents of the box, they are simple to use. Apply the lubrication inside of your anus. Twist the small device, and it will gently vibrate. Insert the vibrating device inside of your anus for the rest of the day. It will be uncomfortable, but you'll soon be accustomed to it. Come to my office at 4 pm and I'll remove it. Will you be a good girl? x Mr. Halpern For a brief moment, she didn't know how to feel. The whole thing was escalating to a point which made her nervous. But the wetness between her legs disagreed. She was aroused. There was no doubt about it. And she wanted the promotion more than anything. Sara put the box on the floor and held the small lubrication in her hand. She opened it and squeezed it onto the tip of her finger. Then came the weird part. She briefly sat up and lifted her skirt. Then she pushed the tip of her index finger inside of her anus. Nothing had ever gone inside of her anus before. Several guys had asked, but she always declined. But for Mr. Halpern, she was willing to make an exception, as she lubricated her own ass with her index finger. At least her finger was thin, she thought. It was uncomfortable, and when the job was done, she pulled out. She used toilet paper to clean the lube from her finger, then she tossed it inside the toilet to flush later. Next, she picked up the small 3-inch vibrator. Even though it was short, it was fairly thick, which made it dreadful to think about. It had a long string on the bottom so it could be pulled out. At least she didn't have to worry about the device getting stuck in her ass. There was no point in waiting. She needed to get back to work so she could finish editing the horribly written article. She twisted the object, making it vibrate gently. Then she reached below and pressed it against the ring of her anus. It was very uncomfortable as she expected, but the lube made it easy. It was a bizarre sensation feeling the vibrations against her little hole. But it also felt good. It stimulated nerve endings she didn't know existed. After the ring of her anus adjusted, she pushed the device deep inside of her rectum, stretching her canal. More nerves were being stimulated by the vibrations inside of her ass, and it slowly started to feel good, despite the tight stretching feeling. When she stood up, it only became more uncomfortable. But she had no choice but to get used to it. Sara adjusted her dress, then she collected the box so she could throw it away. She returned to her desk and tried to focus on work, even with the device buzzing inside of her delicate anus. *** By the time she was done for the day, her anus felt sore beyond belief. She rushed to Mr. Halpern's office to get the vibrator out of her ass. The secretary at the front desk turned her attention to Sara as she approached. "Mr. Halpern is expecting you," the secretary said. "Feel free to enter his office when you're ready." Sara gave a forced smile, with her anus sore. "Thank you so much." When Sara opened the door, she expected Mr. Halpern to be alone at his desk. Instead, there were three other men. Men she had never seen before. They sat in a circle having a discussion. All of them were square older white men in suits, who looked like they were clueless about modern fashion. "Sara, welcome," Mr. Halpern said. "I'd like you to meet some hedge fund managers that we're partnering with. We were just discussing you. I told them you'd be coming at any moment. Sorry, our meeting ran a little long." "Hello," Sara said with a painfully shy demeanor. "Nice meeting you all." "Unfortunately, this meeting will last another hour. So these men will have to watch our little process." Sara looked at the old men. "Do they have to?" "Well, I'm afraid I've already told them about it. And they're all very eager to watch a pretty young thing like you." The hedge fund managers all agreed, offering encouraging words to Sara, telling her not to be shy, and that she's very beautiful. Sara did her best to show a brave face, and to not let them know how humiliated she was, but it was a failed attempt. "Fine," she finally said. "Can we get this over with?" "Of course. Now bend over my desk. Keep your bottom pointed towards our new friends." Sara walked passed the men and she put her hands on the desk. She wanted to finish the experience as soon as possible. Then leave as quickly as possible. The boss stood and brazenly flipped over the bottom of Sara's skirt, leaving her bare butt completely exposed. Sara felt humiliated as the hedge fund managers made little comments to each other. "Oh my," Mr. Halpern said. "You're dripping wet. I'm surprised there aren't any stains on your skirt." "Can you please remove it already?" "What's the rush?" "It hurts," she replied. "Very well." Mr. Halpern pulled the string and removed the small vibrator from her ass. It gave a stinging sensation as it vibrated its way out of Sara's tight anus. It was a feeling of relief when the object was fully removed. Sara tried to stand, but Mr. Halpern put his hand on Sara's back. "Stay where you are," he said. "We're not done yet." She remained bent over, with all the men looking at her naked bottom and wet pussy. "Are you a virgin down there?" he asked. "Yes." "Not even a finger?" "I've had fingers in there," she admitted. "But nothing as large as that vibrating thing." "Anal virgins are my favorite. I'm sure my friends here agree." The hedge fund managers all agreed, giving a clear sign that they were enjoying the show so far. "What happens now?" she asked, hands still on the desk. "Hold still. I want to feel your tightness." Mr. Halpern pushed two of his fingers inside of the anus. The lubrication was still there, giving an easy entrance. He pushed all the way, feeling the tight grip of her rectum. Then he moved his fingers around. In and out. Back and forth. The only thing Sara could do was squirm as her anus was being violated. The fingers pulled out. Before Sara could relax, Mr. Halpern used his other hand to touch her pussy. He rubbed the pussy and felt her wetness. "You can turn around now," he said. When Sara stood up, she pushed her skirt back down to cover herself. Then she turned around to face the men, who were all staring at her with lust filled eyes. It was a humiliating and degrading experience. Mr. Halpern held out his wet finger. "This came from your pussy. Clear wet fluids. I wonder why." "I was aroused," she admitted. "Why?" "I don't know. I've never done anything like this before." "So you enjoy having your anus played with?" he asked rhetorically. "Do you enjoy being an obedient good girl for me?' "I guess so." He nodded. "You can leave now. Our next meeting will be in a few days. I'll have more surprises for you." When it was done, Sara did her best to be polite to her boss, and to the guests. She said 'bye' to them and quickly left. She brisked past the secretary, wondering if the secretary knew what happened. *** The moment Sara got back to her apartment, she immediately went to the freezer for some ice, which she wrapped in a towel. She placed everything on her dining room chair and sat on it. It was uncomfortable. Especially the hard edges of the ice. But she thought it would help relieve the soreness in her ass. By the time she undressed and went to the shower, she finally paid attention to her badly neglected pussy. The aching in her ass took the attention away from her constantly wet vagina. But as her ass began to recover, the sensations in her pussy became more apparent. She was aroused. Still. Sara used the water pressure from the showerhead to spray her vagina. She focused on the clitoris, which was her favorite pleasure spot. Then she rubbed herself. For reasons she couldn't understand, the day's experience was unusually erotic. She thought about the men watching her in Mr. Halpern's office. It wasn't like she was going to see them again anyway. So she tried not to be overly embarrassed about it. Thinking about it had made her orgasm. A nice sparkling orgasm. *** Days later. When Sara arrived at the office, she went to her desk, saying 'hello' to Chloe in the process. At that point, the two had become very close friends. It made Sara feel bad that she kept secrets from Chloe, but it was for the best. There was a note on Sara's desk. She didn't mention it to Chloe, and she only read the note after Chloe left for a cup of coffee. She opened the note, which was written in the same handwriting as the previous note she had received: Are you ready to be a Good Girl? I think it's time. Come to the main conference room at 10 am sharp. There's someone I'd like you to meet. It's a lovely surprise for you. This is the final phase of initiation. Don't keep us waiting. After she read it, she folded the note and tossed it in a nearby trash. She didn't want to risk anyone seeing it. Her pussy became wet. Her heartbeat rose. After the past few weeks, Mr. Halpern proved to be a man of many surprises. Sara had no idea what to expect. She tried to keep busy for the next hour. It was tough. Whenever Chloe spoke, she tried her best to act interested, but she wasn't. All she thought about was the surprise, whatever it was. At exactly 9:50 am, Sara told Chloe that she had something to do, and excused herself. She wasn't sure if Chloe believed it or not, but there weren't any questions asked. Sara went to the elevator and to the conference room. She was never very good at waiting for surprises. She always wanted everything right away. When she reached the conference room, she saw Mr. Halpern standing next to a tall sexy blond. They were both looking through the window, talking to each other. When they heard the door open, they both turned to look at Sara. "Sara, I'm glad you could make it," Mr. Halpern smiled. "Please, close the door. Have you met Victoria?" After Sara closed the door, she walked towards her boss and got a much better look at the guest. It only took a second for Sara to recognize Victoria, who was a famous model who had successfully become a big time actress. The woman was tall, young, and stylish in the perfect sassy way. Sara was immediately star struck. "You're...you're..." "I'm Victoria." The actress smiled and extended her hand for a handshake. They shook hands. Victoria was always flattered when a fan would gush. "I see you're familiar with Victoria's work," Mr. Halpern said to Sara. "I figured you would. Most young women your age are enamored with Victoria, and rightfully so. She has many admirable attributes." "I'm such a huge fan," Sara replied, still awestruck by the meeting. "Good, because Victoria is going to grace the cover of our big upcoming summer magazine. We were just discussing some details. Anyway, I'll let Victoria do the rest of the talking. I have other business to attend." "Okay," Sara replied, nearly speechless. Before Mr. Halpern left, he put his lips to Sara's ear. "This is your final task." With that said, Mr. Halpern left the conference room, closing the door on his way out. There was a brief moment of awkward silence as Sara was left alone with the famous actress. "Mr. Halpern has said a lot of positive things about you," Victoria smiled. "Oh? Like what?" "This and that. Mainly your anal training." Sara's face turned flush. The anal 'training' was the last thing she expected to hear from such a famous person. For some naive reason, Sara thought she was going to be assigned an important writing job. But it all made sense. Mr. Halpern wasn't done with her ass yet. "It's been an interesting process," Sara replied with some embarrassment. "Please, don't be shy about it. A lot of prominent women in our industry have gone through the same thing." "Are you part of the Good..." "I've never heard of such thing," Victoria politely interrupted. "Oh, right. Of course not." "Do you know why you're here?" Sara shrugged. "I was hoping it was for my first writing assignment. I'm currently an assistant editor. But I guess Mr. Halpern has other things in mind." "You'll be a writer someday soon. Mr. Halpern is a fair man if you play by his rules." "Did you work here before?" "Not exactly," the actress replied. "But I've done a lot of modeling for him many years ago. We have business history together." "So what do you want with me?" "To complete your training," Victoria said openly. "Mr. Halpern mentioned that he was training someone new, and I insisted on finishing it. I've never done anything like that before, so I thought it sounded like a fun opportunity. Besides, I'm a lot more gentle than he is. So I think you'll appreciate it." Sara's eyes widened. If she understood the situation correctly, she was about to lose her anal virginity to her favorite movie actress. It was the last thing she ever could have expected, and it made her wet. "Anything for you. I mean, sure, if you want." Victoria smiled, "You're cute when you're nervous. But relax. This is entirely up to you. No one is forcing you. However, I know that you secretly enjoy this in some way. Mr. Halpern told me that you were a sopping mess in his office." Sara nodded. "The byproduct of his little toy." "That little vibrator?" the actress teased. "How painful." "Tell me about it." "Is your anus still sore?" "Not anymore." "Wonderful, because we're going to take things a step further," Victoria replied. "A big step further. You're an ass virgin, right?" "Correct." "Not after today." Sara gulped, feeling nervous for what was about to happen. It was something she had accepted long ago, but it was finally coming true, and with a gorgeous celebrity no less. "I'm ready." Victoria raised an eyebrow. "Are you sure?" "I am." "Touch yourself between the legs. Underneath your skirt. Then show me your fingers." Sara did what she was told, reaching beneath the skirt to touch between her labia. She felt the moisture. Then she lifted her hand to show Victoria the extent of her wetness. Victoria smiled, "You're right. You are ready." The famous actress took a few steps forward, until both women were face to face. They looked each other in the eyes during the sexually tense moment. "What now?" Sara asked after the long moment of silence. "It's time for you to assume the official position for your initiation. Hands on the table. Stand where the boss usually sits. Keep your butt sticking out." Sara went to the head of the table, where Mr. Halpern usually sat when he conducted big meetings. She put both hands on the table. Then stuck her butt out. Her head turned to the big windows, looking towards the nearby office building. "Are you afraid someone might see?" Victoria asked with a playful tone. "Kind of. I mean, aren't you nervous too? You're famous. Someone might recognize you." "At this distance, I doubt anyone would recognize my face. Besides, I find the whole exhibitionist thing kind of hot. Don't forget that I'm an actress and model. I love being watched." Those words struck Sara when she realized that Victoria didn't mind if office employees were going to watch. "I guess it's kind of hot." "That's the spirit," Victoria said. "Now spread your legs for me. I'm going to lubricate your ass." The big moment was coming. Sara spread her legs. Then she felt Victoria lift the bottom of her small office skirt, exposing her rear end. It was more comforting knowing that she was going to be penetrated by a kind-hearted woman, rather than her jerk boss Mr. Halpern. But at the same time, it was also embarrassing knowing that she was going to be penetrated by her favorite movie star. Sara kept her hands on the table and her eyes forward. She heard a container being placed on the boss's seat, then she heard it being opened. Then she heard a bottle cap being opened. A finger rubbed a cold substance around the ring of her anus. It was a soft womanly touch. Something that Sara appreciated, and helped the process be more comfortable. After the finger applied a gentle coating of lube around Sara's anus, the finger pushed inside and entered her rectum. Sara gasped, but maintained her composure. "You're doing such a good job," Victoria said, continuing to lubricate the tight little asshole. "Such a brave girl." The finger pulled out, and Victoria went back to her supplies. "Are you going to keep using your fingers?" Sara asked. "That's won't be sufficient." "Then what?" "Have you ever been pleasured by a strap-on?" Sara eyes flung open. "No. How big is it?" "Fairly big. I'm sorry. But believe me, this is much better than having to deal with Mr. Halpern. He took my anal virginity, and it was pretty painful." Even though the two women had recently met, Sara felt a kinship between them. Deep down, Sara felt as though Victoria was like a protective older sister, which helped her to relax. Good Girl Sara "Okay. Let's get on with it." Sara heard the sound of Victoria wearing the strap-on. It was scary since she couldn't see how big the object was. But that might have been a good thing. Nerves were building in her stomach. Her fingers gripped the table. The anticipation was over when Sara felt the smooth surface of the sex toy pressing in between her butt cheeks. "Can you use one hand to spread yourself?" Victoria politely asked. Sara reached back with her right hand to spread her butt cheek, and Victoria spread the other cheek, leaving Sara's anus completely vulnerable. The tip of the sex toy was pressed directly against the ring of Sara's anus. After a push, the sex toy penetrated the tight opening. "Oh, gosh," Sara gasped. "It's okay. It's okay sweetie. Be strong. It's almost over. You're going to enjoy it soon, I promise." Sara tried to relax. She heard the container of lube being opened again, even while the tip of the strap-on was still inside of her ass. More lube was being applied, thank god, she thought. There was another push and the sex toy went even deeper in her anus. It entered slowly. One inch at a time. Slowly. Carefully. Stretching her rectum. "That's it," Victoria said lovingly. "Show me what a good girl you are. Such a good, brave, girl." Sara was slightly peeved at the condescending tone, but the gesture was appreciated. She tried her best to relax her ass and body, and it helped with the insertion. The foreign object entered another inch, and Sara wondered just how big that thing was. "Almost there," Victoria continued. "We're almost there." At that point, both women let go of Sara's butt cheeks. It didn't need to be held open anymore. The sex toy was already deep in her ass. Victoria used both hands to hold Sara tightly by the waist. Another push, and the sex toy went much further than Sara could have imagined, making her gasp. "Be a good girl," Victoria said in a soothing voice. "It's almost all the way in. Don't fight it. Enjoy it." The final push was tough. In one swift motion, Victoria had the sex toy all the way inside of Sara's asshole. Her crotch was pressed against Sara's butt. "Oh my god," Sara gasped. Sara's ass felt impossibly full. She was stretched beyond belief. It didn't feel normal. It didn't feel natural. But there were nerve endings being stimulated in ways she couldn't have imagined. The sex toy slowly slid out when Victoria pulled back, but that was a false hope, as the famous actress gave another push. It was no longer about insertion, or fitting the big sex toy in Sara's ass. It was about sex and lust. Victoria held Sara's hips tightly and began to fuck. It wasn't romantic or sensual like Sara's past relationships. Sara's encounter with Victoria was only about lust, and getting her ass fucked. Sara tried her best to relax. The pain and aching never went away. But it began to feel good once her asshole adjusted to the size. The thrusts became harder. Sara panted loudly from the pleasure, giving an occasional whimper from the pain. Sara leaned her face down on the conference table. Her arms were too tired to hold herself up. As she pressed her face on the table, she looked through the window and saw a group of office workings staring, while Sara was getting sodomized by a famous actress. They looked like young men, relaxing during their break. They wore nice suits. They were pointing and laughing at the free sex show. "Oh my god," Sara said, trying to stand upright while the strap-on was still buried in her ass. "They're watching! Take it out!" Before Sara could stand, Victoria put her hand on Sara's shoulders, while temporarily stopping the thrusts. "We can end this if you want," Victoria said in Sara's ear. "But you'll fail the test. You've come too far to stop now. Think about it." "But...but...they're watching me..." Sara's eyes remained fixated on the men watching in the other building. "Let them watch," Victoria said, lust in her voice. "I think it's hot. Who cares what those losers think. They can jerk off later for all I care." Sara laid her face back down. "Fine." When Victoria continued, she went even faster. The famous actress and model began to fuck in a way that rivaled most male porn stars. It was painful to Sara's ass. It made loud noises in the room. Slapping noises from their bodies touching. Squishy noises from the excessive amount of lube. Sara cried out loud. Victoria reached underneath with one hand and played with Sara's clit. The pussy was dripping wet, and Victoria knew it would probably drip onto the carpet later. But that was for the cleaning people to worry about later. "Cum for me," Victoria said. "I want you to cum. I want you to orgasm from your ass being pounded." "Ahhh..." Sara gasped. "It hurts!" The famous celebrity pounded even harder and rubbed the clit even faster. "Focus on the pleasure. That's it. Be a good girl for me. Cum the way a good girl should." Sara screamed at the top of her lungs as the pleasure from her ass and clitoris became too much. Her toes curled inside of her heels, and her fingers squeezed the hard surface of the table. Her eyes widened and her lips quivered. Her entire body stiffened as the waves of pleasure flowed through her body. Then she suddenly relaxed. Victoria stopped what she was doing, and slowly pulled out, leaving a strange gaping feeling in Sara's rectum. Suddenly, Sara felt empty inside, but she was glad it had been removed. Both women struggled to catch their breaths, especially Sara who was breathing heavily. She pulled her skirt down and turned to face Victoria, who was naked below the waist, while wearing a large strap-on. "Jeez, how big is that freaking thing?" Sara asked, breathing heavily. "A nice 7 inches. Not a bad way to lose your anal virginity." Sara stumbled back, then she sat on a leather chair. "God, that orgasm. The feeling in my ass is still there." Victoria smiled, "Well, Good Girl Sara, it's a feeling you'll get used to. Because with your upcoming promotions, your ass will be put to good use." The famous actress removed the strap-on and put it away, while standing bare bottomed in the conference room. Sara was still too stunned (and sore) to move, while she watched the actress fix her clothes. Before Victoria left, she explained how much fun she had, and how much she enjoyed taking Sara's anal virginity, and welcomed her to the club. They kissed on the lips, and Victoria left while Sara was smiling. The End ***** Your votes & comments are appreciated.