The Sissy Factory free porn video

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The chime of a doorbell informed Felix that his first applicant arrived. For some reason he felt a little nervous. 'I got through everything with Caravel City,' he told himself quietly, 'but this gives me the jitters? What's up with that?' Thinking back to the events of the past two months Felix was largely amazed that he wasn't caught, although there were certainly a couple close calls. Cat getting arrested, for one, didn't really help matters. Fortunately Felix was able to successfully purge the nanobots from her system and completely wipe her memories, leaving her stuck as Carl Snow, the unfortunate bastard who got caught insider trading...again. Money soon became tight for Felix and his girls. Although all had vanilla jobs it wasn't enough to make ends meet and continue to pay for upgrades to the nanobots. Brooding in his compound one day he thought of a possible solution. With all the other girls busy he decided to test his idea with Anna, a sissy he converted with more conventional methods before everything that happened in Caravel City. He and his partner flew out to Forreston, on the mainland about 6 hours away, and bought a decent two-story house to start his new venture. Felix heard Anna answer the front door with a warm greeting, her raven black hair absorbing all light which approached. Felix smirked as he thought of the outfit she wore, a catsuit which appeared to be "wet", matching boots with a heel, and a blue headband to hold back her hair. A choker with a large sapphire sat right over her Adam's apple, to conceal her true sexual nature and to compliment the rest of the outfit. From the small part of the conversation he could tell the applicant sounded nervous, but no doubt Anna was working to put him at ease. "Sir, Mr. Chung is here for his appointment," Anna announced up the stairs. Felix stood up, adjusted his black polo tucked into crisp jeans, and made his way out of the office and down the stairs. He was slightly relieved to see that Mr. Chung resembled the photos he had seen online and happy that he found someone finally worth his time. Felix reached the bottom of the stairs and smiled, extending a hand to the young man. "Mr. Chung, it's finally good to meet you," he said, making direct eye contact as he did so. "Uh, thank you Mr. Cassidy," he replied, returning the handshake. "And please, just call me Eric." "Alright, Eric, let's go ahead and have a seat on the couches here," Felix indicated. As the two men settled in Anna remained standing, hands folded in front of her. "Can Anna get you anything to drink?" "Just water would be fine," Eric said weakly. Anna nodded and headed towards the kitchen, the sound of her boots echoing throughout the house. "Relax Eric," Felix said reassuringly. "She's my business partner. Everything we discuss today will strictly remain between the three of us." Hearing his promise Eric visibly let his shoulders slump a little, sinking back into the couch. Moments later Anna returned with a glass of ice water and sat down next to Felix, crossing her lands and taking out a notepad as she did so. "Great, now we can start," Felix declared. "Now I won't force you to embarrass yourself Eric, so let's just get this out in the open: you have considerable experience dressing as a woman, correct?" Eric took a sip of water and nodded quietly. "I've been doing it since I got to college. So, about five years now?" Felix nodded while Anna began to scribble some notes. "Good. And from the pictures you have on BioMania, you certainly look the part of a passable female. Tell me, how is your job going?" Eric set the glass on a nearby coffee table, adjusting his posture nervously. "Rather shitty," he admitted. "I wish I could find something else that pays better, but the economy just sucks too bad right now for me to even be caught looking." "Well I've got a business proposition for you," Felix countered, narrowing his eyes slightly. "I want you to model for me." Eric sat silently for a moment and asked, slightly confused, "You mean...just for one shoot?" Felix chuckled slightly. "No, I mean as a career. Part-time, of course. As a model I can offer you $200 a shoot, more if a client asks for something special." Eric brightened up after hearing the offer. "Oh wow, that would be awesome. I don't really have a lot to clothing to dress with though." "We are actively working on expanding our wardrobe," Anna chimed in, happy at her contribution to the idea. While Felix certainly had some sense of taste Anna knew better and was fortunately able to help make positive investments for clothing. "Indeed," Felix smiled, glancing over at Anna. "The more this operation expands the more clothing we can bring in and offer our models. Eventually we might get to the point that we can offer a free outfit to our contract models every month." "Contract model?" "Right, you would be coming in as a "freelance" model, or basically shooting whenever you want. Which is fine. However we want to have a guarantee that we can constantly get new content. So if you sign a contract you would be required to shoot a certain number of scenes and videos per year, depending on the compensation and benefits you're looking for." "Oh I certainly couldn't be a contract model," Eric protested. "No worries," Felix held his hands up defensively. "That's not an option we're offering right away. First we have to get a solid clientele base built up and then we can look at contract models. At that point you're pretty much making full feature films, which have much higher, and lucrative, production values." Eric nodded, taking the information in. "So you said I would most be able to do a trial shoot today?" "Correct," Anna replied, opening a folder and taking out several sheets of paper. "This is a model release form, informing you that photographs will be taken of an explicit nature and published to a website. You do understand that you're essentially making porn, right?" "Yep," Eric swallowed, "But wait, I'm not going to show my male face or anything correct?" "You will not," Anna answered. "We cannot guarantee that you won't be figured out, however. Which is what this second from is for, stating that we are not responsible if you potentially lose your job as a result of working with us." Eric scanned the document carefully. Felix crept to the edge of the couch, wondering if Eric would still agree. Seeing him sign his name on the dotted line forced a small grin to Felix's face. 'This could work after all,' he thought happily. Anna gave Felix a warm smile in return, sharing hissentiment. "Okay, anything else?" Eric beamed. "I think that's everything," Anna said, looking over the paperwork carefully. "Alright, if you follow me to the bathroom I'll get you cleaned up for your first shoot while Felix sets up the equipment." *** In the bathroom Anna had Eric discard all clothing and shower, removing all body hair in the process. Afterward she led him down to the hall to a room which was sealed shut with a heavy door, a thumb pad utilized at the entrance. She swiped her thumb across the display, which turned blue and sounded a tone of approval, causing the door to slide open. Anna led Eric into what he probably thought was the largest closet he had ever seen. Rows upon rows of shirts, dresses, blouses, accessories, and shoes were behind display cases, stretching across all of the walls. Lights gradually became bright, allowed Eric to look around in absolute amazement. A stairway leading down caused him to think more clothing combinations were possible. Eric walked towards a nearby display case which held a number of wigs, appearing to be of rather high quality. "This is amazing!" he exclaimed. "Everything is certainly nicer than anything I have at home! How did you guys afford all of this?" "Mr. Cassidy made a serious investment into our wardrobe holdings based on my recommendations," Anna explained. "After all, the customers and our models have to love their options, right?" "Yeah, but it's going to take forever for me to find something to wear," Eric said. "Not with this," Anna replied as she pointed to a terminal in front of her. Eric walked over and saw what she was referring to. An iPad was turned on and showed a number of clothing combinations, changing the display every couple of seconds. "First thing you need to do is set up a profile," Anna instructed. "That way everytime you do a shoot you won't have to enter your measurements over and over again." Eric did as he was told, typing in his name and measurements. On the section for 'Preformer Name' he paused, unsure of what should be used. "I never thought about a stage name," he admitted, turning towards Anna for advice. "Let's keep it reasonable," she suggested. "Perhaps feminizing your first name and picking a different last name?" Eric nodded and pondered the question for a second longer before entering his final answer and pushing submit. "Welcome," a computerized voice sounded from some unknown speaker. "Cool, you're in," Anna smiled. "Now for the outfit. You can pick one of the themes the computer suggests or do something custom. Everything you can select we have in your size, so go ahead and choose what you think is best." Eric shifted the various articles of clothing back and forth across the screen, wondering what should be the theme of his first shoot. After contemplating the problem for a moment longer he decided on an outfit. He stepped back a little so Anna could approve of his choice. "Oh, nice," she exclaimed, "that really goes with your figure. Do you want to have butt and breast implants for this?" "That's an option?!" Eric asked, totally shocked by the revelation. "Yep. Just hit the 'next' icon and you see the options available." The choices were indeed impressive. Eric has the potential to have either a small ass or a complete bubble butt, and tiny breast to a voluptuous chest. While he was intrigued by the possibilities he declined the opportunity. "I think it kind of kills the mood for this setting, especially if it's going to be in the living room," Eric explained. "I agree," Anna nodded. "In that case just touch the 'render' icon and the outfit will be retrieved." Eric pushed the appropriate icon and unseen mechanical arms suddenly shifted around the display cases, selecting the series of clothing items he selected and dropping them into a chute below. Directly behind the display was a receiving table where all the items appeared from the bottom, in a neat row. After everything gathered together Anna walked over to the table and beckoned for Eric to join her. "Let's get you ready for the first shoot." *** Felix had finished setting up the equipment for the shoot and was busy on his phone, booking some additional applicants for interviews and screening others to determine if they were worthy enough of advancing to the next stage. 'Looking like we may have a home run with Eric,' Felix noted quietly, 'but we're going to need more models to just open the website. And if start off updating once a week we'll need probably five models on staff just in case one gets sick or backs out or something. So if I can get Eric to do three shoots that means the others will only need-' "Mr. Cassidy," Anna interrupted Felix's train of thought, causing him to jump slightly. "May I present to you our first performer, Erica Lee!" She extended a hand towards the wall that Erica hid behind and the model timidly walking out to be inspected by Felix. He let out a low whistle, impressed by what he saw. "Well look at you," he laughed. "You certainly make quite the girl...'Erica'." "Th--thank you," she replied shyly. Erica was dressed in a tight white polo shirt and jean shorts, which went well with her body size. Makeup allowed the young man to be completely passable, easily hiding any blemishes and working with naturally soft features to cause him to appear exactly like a young woman. The wig he chose was a shoulder- length cut that was a light brown in color and worked with his facial and head dimensions. His green eyes shined brightly, aided by an appropriate amount of pink eye shadow complimented by similar lip gloss. As Felix continued his inspection he noticed a pink-colored headband on top of Erica's hair. Finger and toenails were painted a bright blue to provide a different color but Erica wore wedge shoes with a bright pink strap across her foot, the shoes giving her about two inches more in height. She slowly turned to allow Felix to get a full view. Towards the end she struck a couple stereotypical model poses, eliciting a laugh from all three people in the room. "Well you clearly pass," Felix announced proudly. "And since you're eager to model let's get started." Erica nodded and walked over to the couch and, upon seeing a magazine, picked it up and began reading. "Perfect!" Felix coached, beginning to snap pictures. Anna reviewed the photos and adjusted the lighting as necessary to get the perfect images. After a few minutes she walked into the kitchen and returned with a lollipop, handing it to Erica. She immediately began sucking on the candy playfully, her tongue wrapped around the sugar globe. Felix moved in close for these shots, snapping them quickly and moving back to observe the entire seen. "There you go," he encouraged her. "Think 'Girl Next Door' right now." Erica nodded, posing for a couple extra shots. "Now here comes the fun part," Anna said, licking her lips slightly in anticipation. "Why don't you lift up that pillow next to you?" Erica did as she was told and gave a surprised look on her face upon seeing the dildo that was hidden underneath. "Wow," she commented. "I definitely don't think I've ever used one this big before." "Mmm," Anna moaned slightly. "I guess there's a first time for everything, right?" She winked at Felix, demonstrating that she remembered her own initiation process fondly. Felix smirked and returned to the task at hand, snapping more shots of his new model. Erica gently licked the tip of the dildo, putting in her mouth and looking innocently at the camera. Felix's reaction was to snap a number of photos in quick succession, pleased at the level of talent she was displaying. "Now I think it's time for things to get a little bit more interesting," Felix ordered. Erica nodded and faced away from the camera, beginning a small strip tease. Her shorts quickly came off, revealing a bright blue set of panties. A noticeable bulge could be seen underneath the soft fabric. "Do you want me to keep my clit covered or exposed?" she asked, biting her bottom lip nervously. Before responding Felix took a few shots of her scared expression. "Do whatever makes you the most comfortable," Felix replied, remaining focused on his task. "And I can tell you what doesn't feel comfortable," Anna said, walking over to the couch. "Using a dildo in a dry asshole." Anna's right hand was covered by a latex glove with lubricant, ready to prep Erica for her insertion. "I'm going to have a little bit of fun first," she whispered in Erica's ear, eliciting a sigh of anticipation from the trans woman. The duo shared a passionate kiss, tongues locked in an ever-increasing fury. With two fingers Anna pushed Erica's panties to the side, exposing her eager butt. Slowly Anna inserted a lube-covered finger into Erica, eliciting a cry of pleasure and pain. "That's it," Anna cooed encouragingly, "take it. Take it like the *woman* you are." "Yes..." Erica moaned. Her hips began to thrust back slightly at the sensation, giving Felix new material to capture. The bulge in Erica's panties also grew in response, reflecting the state of bliss she currently found herself in. After sufficiently preparing their new model Anna stepped back. "Don't worry," she smiled, "there will be plenty of time for us to play in the future. Time to finish your debut." Erica nodded and with her back still turned towards the equipment she positioned the dildo at the edge of her ass and began the process of insertion. The sensations which radiated from her bum caused her to moan loudly, eager to go farther but remembered the need for patience. Erica's downward thrusts increased in frequency, matching the upward force from the dildo. Beginning to lose her sense of place Erica grasped at her chest, revealing that she didn't wear a bra. Playing and pinching with her nipples Erica let out one loud, feminine moan and her entire body shook, indicating a climax from anal stimulation. After leaning against the back of the couch for a couple minutes she straightened her hair and clothing, turning back around to face Felix and Anna. "So, how did I do?" she asked nervously. "Flawless," was the first adjective that popped in Felix's head. "I think you're going to have a very bright future with us, Erica." *** Months after opening The Sissy Factory continued to make steady progress. By carefully recruiting and controlling public knowledge of his operation Felix cultivated a group dedicated models who frequently worked to produce content. Contrary to his previous position Felix began to take models under contract, with the understanding that they must produce explicit sexual scenes. Erica stood as the natural choice for becoming the first contract model; shortly after her promotion she had the first opportunity to practice. "Come in, Mr. Gaines," Anna smiled as she opened the front door, "we have been expecting you." "Thank you," he replied nervously. George Gaines was uncertain as to whether the offer he received from Felix was legitimate or some sort of police sting. His casual business suit indicated a sense of professionalism, although the wrinkled shirt spoke otherwise. A receding hairline and large stomach gave him the perfect appearance of being a "daddy". After surveying the house and realizing he wasn't set up George visibly relaxed and continued the conversation with Anna. "Looks like an interesting setup you have here," George commented. "You conceived of this idea yourself?" "Actually it was Felix Cassidy," Anna explained. "I'm his executive assistant." "I see. Are you potentially available as one of the girls around here?" Anna moved in close to George and whispered seductively "no, I'm the boss's girl. Besides, you couldn't handle me. What we do have on the other hand," Anna called as she walked away, motioning for George to follow, "are a number of sissies who should be able to meet your needs." Once the pair reached the door to the storage room Anna used the keypad and ushered George inside. She led the client over to the same terminal and began her explanation. "This terminal houses all of our model information, clothing options, and potential scenarios. You were already pre-registered with an account, so all you need to do is confirm that everything on the screen is correct." George looked it over and nodded. Pressing confirm he was surprised to hear "Welcome, Mr. Gaines," from a computerized voice. "That's impressive," he gasped. "It gets even better," Anna smiled. "So first you need to select your model. Unfortunately we only have one model available for sex, if that's what you're interested in. Her name is Erica Lee." "She's beautiful," George remarked, studying her profile intently. "I'll take her." Anna continued her explanation. "Now you will need to select what it is that you want to do with Erica. You can choose the scenario based on the rooms we have available." "Would a classroom be one of those options?" "Of course," Anna replied, showing him the proper icon to select. "Do you want Erica to wear a schoolgirl's uniform as well?" "Yes," George replied eagerly. "Now for the last part, you need to describe briefly the scenario you want to enact with her. Are there any specific dialogue points you want her to mention? Try to keep those to a minimum; we try to prevent our girls from memorizing too many lines." After thinking carefully George typed his specifications into the program submitted the information. "Bid approved," the computerized voice announced. Mechanical arms worked to gather the necessary clothing and props. "The room you selected has a two-way mirror to allow anyone with the proper key code to view what's going on inside. The only persons who have this code are myself and Mr. Cassidy. I must warn you, however, that Mr. Cassidy is meeting with a number of clients today and the possibility exists that he show them what you and Ms. Lee are doing. Do you consent to having your performance viewed by others?" George pondered for a minute and shook his head. "I don't see it being an issue. I...I kind of like the idea of being watched anyway." "Very well," Anna smiled. "If you follow me I'll lead you back to the reception room to enjoy some refreshments while we prepare Erica and the room for your encounter." *** George sat at his desk, grading papers from the quiz students took earlier in the day. A knock at the door broke concentration. "Come in," he called out, looking up from his papers. Erica slipped into the classroom and quickly closed the door behind her, standing directly in front of George's desk. She wore a white button-up t-shirt which showed her tight stomach. A plaid red and blue skirt sat low on her hips. Her Converse sneakers and knee-high socks completed the lower portion of her outfit. Red eye shadow and a light lip gloss comprised most of her makeup. Erica's hair remained straight and fell to her shoulders, but with light streaks of blonde running through it and a red butterfly clip holding back her bangs. "Hi Mr. Gaines," she stated seductively, "I was wondering if I would be able to make up the quiz I missed earlier?" Annoyed at her audacity George shook his head no and went back to grading. "You know the policy Miss Lee. Quizzes cannot be made up. No exceptions." "But sir! I've already missed five quizzes for the semester. If I don't take this one then I'll--" "Automatically failed for the semester," George finished. "I know, I'm the one who wrote the damn syllabus after all." Erica put her books down and leaned in towards George. Her B-cup breasts strained against the shirt she wore, giving him the perfect view of her cleavage. "Mr. Gaines, please! I can't fail another class! My parents would force me to drop out of S.F.U. and I don't want to go back home!" "Well, I must say that you dress the part. A shame you don't act like it," George smirked, rising from his desk and coming around to the other side to approach Erica. "Excuse me?!" she challenged, unsure of where this was going. "You know what class this is," George stated plainly. "And I know you aren't really a *she*. Is that right?" Erica backed up into an empty desk, utterly shocked that someone figured out her secret. "How did...?" "Oh please," George laughed, "did you really think I wouldn't notice? So admit it, you aren't a female are you?" Looking down at the ground Erica mumbled, "no sir." "But you dress like a girl, don't you "Erica"?" "Yes sir." "So what does that make you?" "A sissy, sir," Erica said quietly. "That's correct. Now there is a way for you to pass my class. But you must follow all of my instructions. Can you do that?" Erica's face brightened upon hearing the offer. "Yes, I'll do anything Mr. Gaines." The professor studied her for a moment and moved to retrieve something from his desk. "Bend over in front of my desk," he ordered. *** "The entire arrangement regarding The Sissy Factory centers around choice," Felix explained to the handful of investors being given a tour of the facilities. Felix smiled to himself as he used the term "investors" loosely. A collection of horny businessmen, lawyers, and government officials wanted to delve into their deeper sexual fantasies. Providing money to Felix Cassidy was merely a means to an end. "Choice in what way?" one of the investors piped up. "Creating the perfect scene," Felix answered, picking an iPad from the table and handing it to the guest who stood closest to him. "For those sissies seeking to be seen and taped, they can choose their outfits, the location, and the premise of the shoot. Still and video photography options are available. There is an option for the shoot to remain private or disclosed in the future for the website we're currently building." "You're building a website as well? That's quite an ambitious strategy. Most of what you create probably isn't considered usable by the internet community though." "That's where I have to disagree with you sir," Felix responded, unlocking the tablet and opening the program which enabled the selection of clothing and accessories. "All of the items our sissies can dress in are of the highest quality. We recently added a number of make-up artists and stylists to ensure that each sissy can live out their fantasies the way they imagined them. As you can see from the tablet we have over 1,000 wigs, blouses, skirts, and dresses to choose from. Being able to cater to virtually anything that's asked for." "Will there be a chance for viewers to select which outfits the...sissies...will wear?" the first investor asked. The annoyance of the man's question wasn't evident based on the wide grin Felix wore. "Oh we have something better. Follow me gentleman." Turning down another hallway Felix stopped the group in front of a mirror. "Not only can customers select what outfit the sissies wear," he continued, pressing a sequence on a nearby keypad. The mirror suddenly turned into a viewing glass for the next room, causing the investors to gasp at the scene they were witnessing. "Some of them can even become participants themselves," Felix finished. The room appeared to be a small classroom, stereotypical for porn movies. The words "Human Sexuality 101" and "Mr. Gaines" were written neatly in one corner of the chalkboard, along with various posters scattered about the room. The eyes of the investors, however, were drawn to the student bent over in front of the teacher's desk, her butt red from the constant smacks of a ruler. A man appearing to be in his late 40s and balding had one hand on the girl's back while the other held the ruler, striking her backside as she incessantly repeated a mantra. "I love being a sissy girl," *SWAT*. "Being a sissy means that I'm a good girl," *SMACK*. "I must always perform well enough to earn an A," *SMACK*. "Only the best girls get an A in Mr. Gaines's class," *SWAT*. Minutes into the session most of the viewers realized that the girl had a sizeable bulge growing in her panties, gaining sexual pleasure from the force being applied to her ass. Most nodded in approval while one of the investors, standing in the middle of all the others, rubbed his crotch and began to breathe heavily. 'Well it's good to see that Erica isn't the only one with the growing bulge,' Felix smirked. "So our clients can select the sissy's wardrobe, the location, and what they want to happen. This information is given to the sissy early enough before their interaction so it can be internalized. Thus they can act it out with as few flaws as possible and bring the fantasy to life for both participants." "Time for your oral examination, Miss Lee," Mr. Gaines ordered greedily, unzipping his pants and parting his brief to reveal a swollen cock. "Yes Mr. Gaines," Erica replied happily, instantly dropping to her knees and viciously sucking the head of her teacher's cock. Satisfied that he provided enough of a peep show Felix keyed in a sequence again and returned the two-way mirror to normal. "Using the program on the tablet, the sissies or clients can create "bids", or a basic description of what they want. Members to our...organization...in addition to our registered sissies can browse the bids that are put up and select the ones that appeal to them. A bid that someone actually carries out is called an "interaction"; all interactions take place on our property. Participants are screened for diseases and drugs before being allowed to participate." "So how exactly do you make money, if a client or sissy chooses to not have their interaction recorded?" a third investor asked. "We charge a fee for every interaction," Felix answered, "for testing, maintenance of the facilities and clothing, payment for the sissy, and other necessary operating costs. These can run up to about $800 for the most basic bid, $1200 or more for complex ones. Recording interactions will reduce the price by half, regardless of what the bid is actually about. We can easily make up for the "lost" profit in internet sales." "Is there a chance for online viewers to submit bids?" Felix, taken back by the question, managed to produce a smooth answer. "Not initially, for two reasons. One, this is technically still in the testing stages, although as you can see," Felix trailed off as he keyed in the sequence for the two-way mirror, showing Erica, now naked except for her sneakers and knee-high socks, being absolutely rammed by Mr. Gaines. Her sissified moans carried noise throughout the hallway, unaware that her performance was being actively evaluated by others. "We have the potential to really make this take off the ground," Felix finished, shutting of the view for a second time. "The other reason for not taking bids from the audience is that it creates an intense desire for viewers, something which can be exploited." "Exploited in what way?" investor number two asked. "That's something I'd rather keep as a trade secret," Felix hesitated, "yet I assure you that the plan can work with proper financial support. And that is what I ask of you gentlemen. A contribution of $10,000 from each of you can make this experiment sustainable. To demonstrate the Factory's gratitude for your extreme generosity I offer you all an interaction with any scenario and up to two of our models being used once per month, no extra charges, for 12 months. This will be combined on top of receiving a reimbursement rate of 145% after the company goes public in approximately a year and six free interactions with our models per fiscal year. Any questions?" "Yes, I have one," the first investor asked. "Are you sure that all the sissies that you hire are willing to put the necessary passion into their work?" On instinct Felix keyed in the code for the two-way mirror, revealing Erica squatting down in front of a sweaty Mr. Gaines, stroking her clit furiously. "Please give me your cum Mr. Gaines," she begged hungrily. Unable to hold back any longer the teacher complied, shooting a thick stream on the sissy's face. The orgasm seemed to last for five minutes as thick white wads landed across Erica's face, caking her lips in the sticky goo. When Mr. Gaines was finished he sighed with content and said, "I think in your case you deserve an A, young lady." Felix shut off the mirror for the last time. "Any *other* questions?" *** The investors chatted amongst themselves as they exited The Sissy Factory, unsure of what Felix had to offer. A disappointed Felix watched them leave one of the men turned back around and approached him. "Excuse me Mr. Cassidy," he apologized, "but I had a question for you." Felix straightened his posture and smiled. "Sure thing. What can I help you with?" "How capable are you to answering the needs of prospective clients?" "So long as the request is reasonable I believe it can be accommodated," Felix stated matter-of-factly. "For more complex requests it would take a couple days to find the proper person, props, and setting." "Most of the investors are a little unsure of you really catering to the needs of clients. Although I must confess that their tastes are a little...eccentric, including my own. We all decided that we'll either invest in this project together or not at all. I don't want to disclose the exact number of us who are still on the fence but I assure you it's manageable if you demonstrate the proper competency. So I decided to offer you a little challenge." "Oh?" Felix raised an eyebrow. "What did you have in mind?" "I had a fantasy I would love to have acted out by one of your models. I'll send you the details in an email later on this afternoon. I want to be able to do it this Friday. If you can make it happen I'll speak to the undecided group of investors and convince them to buy in." Felix thought for a moment and then nodded. "Deal." "Fantastic," the investor replied. "And good luck. This one might be a little over the top." *** Felix studied the set carefully, impressed by the work of his construction crew in a short amount of time. "So are you sure this is going to work?" he asked the foreman. "Si," Emilio replied, wiping his hands on a towel. Felix spent a considerable amount of time finding a construction crew and tech team willing to carry out his projects and ask a minimal number of questions. Combined with the opportunity to enjoy some of the girls and Felix found a group of men able to meet the needs of clients on short notice, even if they appeared to be borderline ridiculous. "Most of the machine is prefabricated; we simply needed to ensure a sufficient power supply is available to run it." "How much time do we have?" "About 3 hours, sir," Emilio said confidently, "and we have capacity for 20 persons, just as the client requested." Tapping a button on his headset Felix called out to Anna. "How does the rest of the crew look?" he asked nervously. "Everything is just about set, Commander," she replied from another room in the house. "All personnel have been briefed and are simply waiting to take their places." Checking his watch Felix was relieved to see things were slightly ahead of schedule. "Excellent work Emilio. Tell your men they will be rewarded handsomely for pulling off a miracle." Felix walked away to prepare for the next phase of the plan. "And if this works out the way I hope," he called over his shoulder, "I might even *triple* their pay for today!" *** The passengers for the flight to Caravel City stood impatiently in line, eager to get their voyage underway. Flight attendants smiled and checked boarding passes, welcoming everyone to the waiting plane. Michael Jacobs let out a nervous laugh after realizing he was the last passenger that was boarding. "I hope there isn't any bad luck on being the last person to get on a plane!" he joked. A flight attendant whose nametag read Maria, smiled reassuringly and replied, "Of course not sir. In fact," she stopped for a moment, scanning his boarding pass and handing it back to him, "sometimes the last passenger gets *really* lucky." She winked mischievously and prepared to board the plane behind Michael. Jacobs felt a tingle as he observed the young woman's frame from the corner of his eye. She didn't really have much in regards to breasts but her ass was definitely noticeable, perfect for her slender frame. Based on the skin complexion Michael thought she was Hispanic. Her jet black hair was pulled into a neat bun and a string of pearls with matching earrings served as her primary jewelry pieces. Her nails were well maintained and were painted dark blue, to match the uniform she wore. Maria's shiny black heels stood at about 4 inches in height; he wondered if they were regulation but decided it definitely wasn't worth complaining about to management. Maria sealed the door shut behind her and assisted passengers to their seats. The first class cabin provided a considerable amount of luxury, essential for the flight ahead. Moments after everyone was settled an announcement crackled over the speakers. "Good afternoon ladies and gentlemen, this is your captain speaking. We will be taking off from Forreston on route to Caravel City, which should be about a 6 hour flight. Weather looks good so the flight should be relatively smooth. I'd like to thank you all for flying with us today. Flight attendants please make final preparations for takeoff." The attendants complied with the order, strapping themselves down in seats in preparation for takeoff. A light vibration surged throughout the cabin as the plane roared to life. Michael settled back in his seat as he prepared himself for the long journey ahead. After the plane taxied to the edge of the runway Michael straightened in his chair, eager to experience the takeoff. The craft quickly picked up speed, the airport zooming by the small window to his right. The pilot eased the plane into the air, defying gravity and pressing the passengers into their seats. After a couple minutes the sensation passed and the plane slowly leveled off at cruising altitude. "Thank you for your patience ladies and gentlemen," the pilot announced, "we have reached cruising altitude and you are now free to use electronics and move about the cabin. We are on schedule to reach Caravel City at 8:35 PM." A crescendo of seatbelts could be heard unsnapping as occupants relaxed and began to occupy their time on the flight. Michael pulled out a book he brought with him, a biography on Marquis de Sade. About a half-hour into the flight Maria approached his seat with a beverage cart. "Can I offer you something to drink, Mr. Jacobs?" she asked politely. Michael looked up from his task and smiled at the young woman. "Yes, perhaps a glass of Moscato, if you have any?" "Why of course sir," she replied, pulling out the proper bottle. As Maria poured the beverage Michael studied her carefully. "I must say you are a very attractive woman, Mrs. Maria--" "It's *Ms.* Santos," she corrected politely, handing the glass to Michael, "and thank you sir. I really can't admit this kind of thing but," she leaned in closer so only Mr. Jacobs could hear what she was going to say next, "you aren't so bad looking yourself." "That must the spirit of de Sade which has taken hold of you my dear," Michael replied, leaning even closer to Maria. "de Sade?" she questioned. "I don't think I've heard of him. What does he write about?" "Sexual freedom," Michael answered. "Oh my Mr. Jacobs," she whispered quietly, "I don't think I'm comfortable talking about sex with an absolute stranger!" "Ah but that's part of the thrill Ms. Santos. And I must say that I find your body absolutely...ravishing." "Ex...excuse me," Maria said nervously, "I have to attend to the other passengers." The attendant moved away from Michael and continued her work. For most of the flight she avoided being in Mr. Jacob's presence, slightly disturbed yet interested in their brief conversation. She found herself teasing Michael more as the journey wore on. Bending over in his view so that he could view her ass, leaning forward when speaking to another customer so he could see amble cleavage, and licking her lips seductively when they two made eye contact. Unable to control her growing curiosity any longer she approach Michael and whispered, "Meet me in the bathroom in 10 minutes. Make sure no one sees you go in there." He nodded and watched her hips sway towards the back of the cabin. Before she stepped into the open bathroom stall she looked over her shoulder, winked at her budding paramour, and disappeared inside. Mr. Jacobs studied his watch intently, eager for the minutes to count by. After a sufficient amount of time passed Michael slowly stood up and made his way to the back of the first class area. When it appeared as though no one noticed what he was doing he quickly slipped inside of the bathroom. Michael locked the door to the bathroom stall, leaving him and Maria standing close to each other in the confined space. "The Marquis once said," Michael began, pressing himself onto Maria. He gently began to kiss her neck; despite her protests he continued with his physical touch and flirtatious speech. "'Sex is as important as eating or drinking and we ought to allow the one appetite to be satisfied with as little restraint or false modesty as the other'. Do you believe this is true, Ms. Santos?" "I...I...," she sighed as Michael found the perfect spot on her neck, sending shivers down her spine. "I've never found someone who could appreciate me...or please me...because I'm different." "Impossible!" Michael protested. "I would do nothing but ravish you at every opportunity. Let's see if I know how to please you. And you said that you are different? In what way?" Between his kisses and caresses Maria found herself unable to answer Michael's challenge. He slowly sank to his knees, directly in front of Maria's crotch and took a deep sniff. "Mmm," he cooed, "it seems like someone does want this after all. I'll prove that you're no different from any other woman!" In that moment Michael pushed her skirt halfway up her thighs and yanked down her black underwear to reveal her more intimate side. "Well, that's what makes me different," she whispered nervously. Michael remained silent, staring at Maria's 7-inch cock directly in front of his face. The balls were on the small side but the width of the cock made her special clit more than a mouthful. "This...," Michael finally said after a moment, "...is going to be much more fun than I imagined." He instantly took the tip into his mouth, running his tongue around the head. Maria fought hard to stifle a gasp of pleasure, surprised by the reaction of Mr. Jacobs. His hands roamed across Maria's chest, eventually reaching the buttons on her suit jacket. Fumbling around with them Maria decided to help provide access, careful to ensure she didn't rip the jacket in the process. She repeated the same procedure with her blouse until a black bra was revealed. Michael pushed the bra up slightly, exposing flesh to the cold air and he began to tweak her nipples, which quickly became stiff from stimulation. Maria's eyes rolled back as her head rested against the side of the bathroom wall. Michael gradually began to take more of Maria's cock into his mouth, establishing a bobbing rhythm on her member. Turbulence began to rock the plane, causing more of Maria's clit to slip into Michael's mouth. Surprised by the sudden sensation he gagged slightly; feeling him struggle with her dick caused something to snap inside of Maria and she soon began to take charge of the situation. "Do you like being a cocksucker, Michael?" she asked. "Please," he said in between breaths, "call me Mr. Jacobs." "I'll call you whatever I please," Maria smiled wickedly. "In fact, I think I'll just call you 'bitch', because that's what you are. A little," she grunted, pushing him mouth back onto her dick, "cocksucking," she grunted again, her hands moving to the back of his head to better control the motion, "BITCH." At that point Maria forced Michael's head completely onto her cock, causing him to gag violently. After a second of this she released him and bent down, whispering a threat in his ear. "You better stop making so much noise bitch," she warned, "because you can get me in serious trouble. And I can do the same to you." "Wh...what would you do to me?" Michael asked nervously. Maria let out a quiet laugh. "There are cameras all around this bathroom. You wouldn't want me to show a video of your cock sucking skills to everyone that you know, would you?" Absolute terror filled Michael's eyes. "Please!" he quietly begged, "don't do that! I'll do anything you want!" "Then you better make me cum. And fast," she replied, forcing his head back down on her. Maria's hips began to smack into Michael's face, becoming increasingly turned on by the gagging sounds her new mate was making. Michael closed his eyes and concentrated on breathing out of his nose to ensure he didn't pass out. Thick lines of saliva pour from the corners of his mouth, landing on the floor of the airplane bathroom. After a few more minutes Maria looked down at Michael and laughed at what she saw. "Oh please don't tell me you can't help touching yourself," she declared, noticing that Michael groped his crotch fiercely. "Mmph mmm mmm mphm mphm" Michael responded, determined to remain as quiet as possible to ensure the other passengers couldn't hear. "I really want to fuck you in the ass," Maria said through clenched teeth, "but we don't have much time. Guess that means you're going to have to swallow my load. "Please Maria, give it--" Maria struck Michael hard across the face. "What did you call me?!" "I thought that was your name--" A second blow to the face cut him short. "*Bitches* like you don't get to call me that. What is my name?!" Maria slapped her rigid cock against Michael's face, causing him to lose concentration. "Mi...Mistress," he begged quietly, "please, can I..." "Can you what?" she challenged. "Please give me your hot cum Mistress," Michael begged. "I love being your bitch, forced to suck your thick clity. Can I please take your load in my mouth?" In response Maria shoved the head of her cock into Michael's mouth and stroked the shaft rapidly. Seconds later her work was rewarded with a geyser of semen pouring into Mr. Jacob's mouth. Her entire body shook violently as she fought to remain quiet. By the time she finished Michael's mouth was full of her seed. Frustrated at what Michael failed to do instinctively Maria hauled Michael to his feet and shoved him against the bathroom door, a hand wrapped tightly around his throat. She leaned in closed and whispered into his ear, "Swallow." Mr. Jacobs complied with her command, struggling past the grip on his neck but ultimately accomplishing his task. Maria ran a tongue across Michael's lips, consuming the light amount of seed which rested on the outside of his mouth. "I'm going to leave first," she decided, straightening her skirt and blouse in the process. "Take a couple minutes to clean yourself up and then leave after me. Understood?" "Yes mistress," Michael replied quietly, remaining pressed against the bathroom door. "When we land, you are to follow me to my hotel room. I haven't been completely satisfied and that's something you're going to answer for." "Yes mistress," Michael said again, looking down at the floor in disappointment. "There's one more thing," Maria added, turning towards a locked compartment on the opposite wall. She quickly spun the proper combination to unlock the box and withdrew a chastity device. "I don't want you to play with your pathetic cock anymore," Maria explained. Ms. Santos unceremoniously opened the front of Michael's pants, inserting his manhood in the restrictive chamber and locking it with a resounding click. Michael looked down and saw a small lock keeping the device inaccessible to anyone who didn't have the key. The thrill of being locked up caused his penis to strain uncomfortably against the mechanism, keeping his fleshly ambitions in check. "Looks like you need it after all," Maria said mockingly. "Don't take too long, in case someone else needs to use the bathroom." "Yes mistress," Michael replied instantly. Mr. Jacobs shifted to the side to allow Maria to slip out, pants and underwear still around his ankles. Michael could feel his own dick strain against his suit pants, slightly stained with saliva. The ability to still taste the strong flavor of Maria's semen sent shivers down Michael's spine. 'How did the situation get out of control so quickly?' Michael wondered to himself as he fixed his pants and shirt, making every effort to appear as normal as possible. 'I...I can't believe I loved it,' he finally admitted. An impulsive taste of his lips confirmed his previous assertion. '*Every* minute of it." When finished he took a deep breath and opened the door, scanning the first class cabin. Maria stood at the front of the plane, retrieving something for a passenger while others chatted quietly or slept. Michael was relieved to see no one staring him down based on hearing any noises; he quickly slipped back into his seat and stretched, suddenly feeling the metallic chastity device press against his thighs. The sensation caused him to jerk slightly, grabbing the attention of another flight attendant. "Is everything okay sir?" she asked with genuine concern. "It sounded as though you were a little sick in the bathroom." "Yeah, I'm alright," Michael replied weakly. "I thought I was going to lose it for a moment but I managed to hold it all down." Out of the corner of his eye he could see Maria smiling wickedly, a hand moving towards her crotch and squeezing it gently. "Well I'm glad everything is okay," she smiled. "The pilot said this wasn't going to be a rough ride but sometimes these things come out of nowhere." 'You could say that again,' Michael thought darkly. "Attention ladies and gentleman, this is your captain speaking. We are now on final approach towards Caravel City, if you will please fasten your seatbelts and turn off all electronics we should be touching down in a matter of minutes." All of the passengers complied with the directive, happy that the flight was finally coming to an end. As the plane touched down and taxied to the main gate Michael felt a mixture of fear and anticipation hit him. Once the plane powered down he gathered his luggage an exited the plane. Maria stood at the entrance, bidding farewell to the guests. "Thank you for flying with us today," she told Michael innocently. "I hope you enjoyed the ride." The strong taste of Maria's semen reminded Michael him of his most pleasurable experience. *** As the simulator powered down Felix and the tech crew monitoring things from the control room erupted in applause, pleased they were able to pull of the feat. "I thought the idea was crazy," Felix said to Anna over the noise, "but we just might be crazier for doing it!" In response Anna planted a deep kiss on Felix's lips then joined the other in the celebration. In less than a day Felix was able to find, set up, and calibrate an airline cockpit with a fake first class section. Calling up all the actors he had under contract and on reserve, sufficiently briefing them on their role, and hoping they wouldn't screw it up caused him to worry constantly. The biggest challenge was Maria, or Mark Santos. Unbeknownst to Michael, Mark never considered himself to be the dominant type in sexual interactions so his encounter with Michael was virgin territory. Yet Felix was amazed at Mark's...or Maria's...ability to embrace the challenge and pull it off well. Felix walked quickly out of the control room and met Michael standing alone outside of the entrance to the simulator. When Felix was within arm's length Michael grinned and extended a hand. "I must admit," he said, "I had my doubts as to whether this type of thing could actually work. But you, Mr. Cassidy, are absolutely something else!" Felix returned the gesture with a strong handshake. "So everything was up to your standards, Mr. Jacobs?" "Absolutely my boy!" he roared. "Everything flowed smoothly. The dialogue, timing of the pilot, the actions of other actors on board. And don't even get me started on Maria! She has such talent! Are you sure you don't have professionals working for you?" "To be honest sir," Felix moved closer and lowered his voice, "This was Maria's first scene with us. We only brought her on board six days ago." Michael looked absolutely stunned. "Really? And how long did it take for you to get the cockpit replica and the model of a first-class cabin?" "A little over a day. The two pieces weren't actually made to go together so my tech crew had to fuse them and change some wiring in order to make it work." "You could've completely fooled me son!" Mr. Jacobs boasted. "Shit, I'm so excited I need to take this chastity thing off before my dick bursts." As he hobbled towards the bathroom he called over his shoulder to Felix. "You've got your pledge for funding and then some Mr. Cassidy! Damn fine job your people did today. Anything you need just let me know!" *** "Between your presentation and the special request we fulfilled for Mr. Jacobs it appears as though you won the investors over, Commander," Anna stated, reading information from an iPad while walking quickly alongside Felix. "All ten targets agreed to finance the operation, yielding $100,000 in instant capital. In addition to that the investors are working on providing more money if we meet certain service targets. There's a potential to expand our monetary holdings to half a million dollars." "Good, seeing as how we've already starting using it," he mentioned, nodding his head towards the construction taking place at the back of the house. With the money Felix saved from Caravel City and the new cash flow from investors he was able to add extensively onto the house, transforming it from a modest abode into a sizeable estate. The main house was still separated by a considerable distance, ensuring that the construction work could continue without disturbing the operation of The Sissy Factory. As the duo entered the back of the house Felix stopped to ask Anna more questions. "What's the status on our strategic reserve of content?" "We're about 65% complete," Anna noted after searching for the information on her tablet. "At the rate we're acquiring new material for the website we are on schedule to launch at the beginning of August." "Good," Felix nodded, letting the information wash over him. "And the man I am meeting with regarding the Factory...we were able to push the appointment up to today, right?" A doorbell served as the answer to Felix's question. He suddenly became a little nervous, hoping that the meeting would end on a positive note. "Relax," Anna whispered before pecking Felix on the lips, "you're going to knock this out of the park like the other investors." The assistant walked quickly to the front door, her heels clicking as they came in contact with the tile floor. Felix walked into the living room just as George Gaines entered, allowing Anna to take his coat. "Ah, Mr. Gaines. Thank you for coming on short notice," Felix apologetically stated. "Not an issue," George admitted. "Anna said that you needed something from me?" "I wanted to get your opinion on the operation I've got here, Mr. Gaines," Felix said. "Sure, as long as it doesn't affect my ability to come back here in the future," George chuckled "Of course not," Felix replied defensively, "yet because you're one of our more frequent and interesting customers I certainly value the insight a man such as yourself could provide." "I heard that you were planning on transforming your operation into an adult content website?" George queried. "That's correct," Felix admitted, "but I hope you can keep that secret under wraps for a couple more weeks." "So, what exactly would make this different from other websites that offer transsexual content?" George wondered impatiently. "Ideally we want to produce content at an above average rate compared to other websites with transsexual content," Felix explained, "websites offering standard content usually publish daily; we want to match that." "Pretty difficult to do for a website which only has fetish content." "We are still working on building up the strategic reserve of videos and movies. The location helps; Forreston has a high population of persons that define themselves as transsexual or would consider having sexual interaction with one." "I can't imagine that you're going to just have a mass casting call to get the content you need?" George queried. "So that means you have something else in mind. I'm assuming it's prostitution. Come to think of it, that's more of less what this operation is, right?" "The more appropriate term," Felix retorted, "is "escort service". Forreston allows for bunny ranches, despite the fact that none have been established before. Part of the process of gathering content is for people to live out their fantasies, both as a transsexual and having relations with one. Those that consent to having their escapades recorded and published on our website will receive a portion of the profits." "Royalties, you mean," George corrected, "and content done with amateurs doesn't really yield high profit margins anyway?" "If by amateur you're referring to that shaky camera bullshit, then you're right," Felix smirked, "however this has far higher production values. We are looking to add professional makeup artists, tech crews, and photographers. The actors are going to remain amateurs. That is, until they perform enough to be considered pros." George, suddenly intrigued by the idea, continued to question Felix's business plan. "I still don't quite understand what makes this different from any other website." Felix leaned in close and whispered the answer. "The difference is *passion*. Part of the reason why these transsexuals dress, why they interact with males and females, why they are willing to show all of this in front of strangers and cameras is because they're passionate about it. It is the way they define themselves and their sexuality. This entire city is like a powder keg. The population that likes transsexualism is high, yet the number of people against it is still greater. That makes it difficult for the trans population to express themselves as easily as cisgender couples. So there they sit, their desires, their fetishes, gathering in greater numbers, waiting for just the right spark." "And that's the spark you think you're providing," George concluded. "Why hasn't someone come and done this before?" "Money is the key problem. It costs a great deal of money to get the resources necessary for a high-quality transformation. Thanks to some of my other work I've got just that. Another issue is timing. The general public hasn't been accepting of this type of lifestyle until very recently. Any efforts to have clubs or meeting places, or physical icons, would be destroyed. If they wound up murdered the police wouldn't go far into investigating. Yet that concept is changing too. The key thing to all of this is to corner the market. Preventing...professional...studios in the adult industry from making a move on this sort of thing. This city's transsexual fetish needs must be fulfilled by The Sissy Factory only." "So you'll need someone who can generate new marketing strategies. Stay ahead of the curve as to avoid utilizing dirty tactics to get the same results. A clean nose means the authorities and the city government won't delve too closely into the details of the operation." Felix nodded. "Anything else?" "Extensive business contacts within the city would also be crucial," George continued, "someone who can get supplies and personnel in at relatively lower rates. Security is also important, not only for the facilities but the actors. So building a network of guards and police officers who are pro-Factory will ensure that anyone who conducts business with us is safe. Some officers are certainly willing to do this voluntarily so it's still possible to avoid the darker methods. Yet to sort it all out will require a decent amount of intelligence gathering." "And do you have anyone in mind with these credentials?" "Well I have the ability to carry out the intel operations, and I do have a solid number of business contacts, so--" "So that means I can count on your contribution," Felix grinned. "What exactly do you think I can do?" Felix gestured to the house around him. "I want you to run this." George remained silent for a moment, unsure of the best way to respond. "Why me?" "I've got other interests I'm working developing. I need a partner I can trust to maintain the operation here and make a profit. We have investors but none of them can think outside of their pants and run things efficiently. You, on the other hand, have the business sense and the interest. I think you're just the right man to handle the operation and oversee its expansion." George continued to remain silent. "Anna and I will remain in Forreston for a couple weeks after the official launch of the website." "That means you won't really become the face of the company," George offered. "Isn't that something you'd want?" "No," Felix responded gruffly, "because in my case this kind of publicity can be rather...bothersome to the future plans I have in mind." "So you need someone operating the business who wouldn't mind that publicity. Of course," George said hesitantly, "that kind of publicity can ruin reputations to the point that I can't find a lot of legitimate work if this little venture doesn't work out." "As COO of The Sissy Factory," Felix countered, handing George a small stack of papers from the nearby coffee table, "you will receive a termination package which should ensure you are well taken care of in the event that the operation ceases." George displayed genuine shock on his face. "Wait, really? That's amazing. I accept. But I don't want you to think that it's just because of the money. I mean--" "You weren't just trying to watch your own ass," Felix interrupted, "but a legitimate business claim. And that's something I respect. So long as you keep up the same vigilance in regards to *our* new business interest." "I'd give you nothing less sir," George said with a smile. *** George stood at the top of the staircase to see Felix and Anna off. "The Factory will be in good hands Commander," offering a hand to his new boss. Felix nodded and accepted the hand. "Oh I know it will be. Plenty of professionals around you. Not to mention the new Mrs. Gaines to serve as your executive assistant." Upon hearing her new title Erica emerged from a side room, straightening her hair. "Why of course, Commander," she smiled, "I wouldn't have it any other way. And again, thank you." "For what?" Felix asked quizzically. "This opportunity. I never thought I would be able to get a chance to be femme, living out this lifestyle and making a permanent transition. That's all possible thanks to you." "A *permanent* transition?" Anna raised her eyebrows. "Yes," Erica replied with excitement. "I decided last night to undergo HRT." "Well that's fantastic!" Anna squealed, hugging Erica in the process. "I'm really happy for you." "Thank you," she said shyly. Turning towards Felix she asked, "I hope you two won't become strangers to the Factory?" "Of course not," Felix reassured her. "We'll certainly stop through often. After all, we're family now. It's not healthy to leave family hanging for a really long time. Unfortunately our flight leaves shortly so we should really be going. Good luck with everything here." After exchanging a few last goodbyes and hugs, Felix and Anna made their way down the stairs and to the front of the house. "Hard to believe we're moving on so soon," Anna lamented. "Yeah but it's necessary," Felix replied, adjusting the bag strap resting on his shoulder. "There are plenty of other projects that must be carried out." "Are you going to clue me in on them?" Anna asked sweetly, grabbing Felix's hand and kissing him on the cheek. "I'll explain on the flight. What I can tell you now is we've got to find a headmistress." "A headmistress? Of what?" Felix smiled wickedly as he reached the front door. "A university."

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THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
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Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

3 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

3 years ago
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The Young Sissy Chapter 3

I was running through an empty parking lot...looking for someone, or something, but I wasn't sure who I was looking for...or what. All I knew that was no matter how hard I looked, how far off into the distance I stared, all I saw was miles and miles of concrete. It was an oppressive emptiness, the vastness of the open space crushing me. I fell to my knees in despair. I don't know why I was looking anymore...everything I had seen up to this point was testament to the futility of hope. At...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

2 years ago
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The 150 Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

4 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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The Reawakening of Sissy Jackson

The Reawakening of Sissy Jackson By Cassandra Morgan The memories came at night, when his consciousness was not on guard to stop them. A little boy, rushing across the playground to his mother. She laughs and picked him up, kisses him on his lips. He is a small boy, frail, too weak to play ball sports with the other kids. He plays on the swings...but not too high. He plays hopscotch. He plays jump rope. The mommy does not care. She likes having her little boy close to him, and if...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

3 years ago
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The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

2 years ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

2 years ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

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