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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 App. Rick quickly gave up reading the details and just started scrolling to the end to hit "OK" so he could actually start using the App. The Sissy App "guaranteed to provide you the utmost sissy experience utilizing cross-platform software synergies," whatever that meant, thought Rick. The program, however, introduced multiple breaks and user prompts to ensure that the key points of the User License Agreement were understood. Rick's eyebrows raised when he started reading the privacy section. "Users will provide data, to include images, personal health information, geolocation information, employment and wage information, addresses, phone numbers, e-mail addresses, and other information directly to the Sissy App, which will securely transmit the data to GRA Software Corporation's secure servers using unbreakable end-to-end encryption, ensuing your privacy and the security of your information." "That's good," thought Rick, as he continued to scroll, "at least my data won't be accessible to anyone." Rick continued to read:"several privacy prompts will display as you progress through the Sissy App program, which will give you to opportunity to share additional information with the App to improve your user experience. These are not required for program completion, but will significantly enhance your experience." Odd. Rick already knew about the $300 non-refundable requirement for the App, which was a lot of money up-front, but the App did not have a subscription fee, and did not require a monthly credit card bill. "Users will select a Mistress or Master to assist them as they work through the Sissy App Program. The Mistress or Master will not interact directly with the user until later in the program. As users complete challenges, a Mistress or Master will audit the sissy's completion and determine compliance with the program. Corrective actions will be administered when an audit determines noncompliance." "That sounds interesting," thought Rick, "someone will be reviewing how I complete tasks in the App?" "Noncompliance will result in corrective actions, which must be resolved to the Mistress or Master's satisfaction. The Sissy App is a one-time program- once a user signs up, they must complete the program. If a user fails to address noncompliance and complete the program, the App will uninstall and the user will not be able to re-install the App. Geolocation, user data, and other user-provided information will be used to ensure identity resolution." Rick was concerned about that section- he would not be able to quit and re-start once he began the program, apparently. He continued reading the "Installation Requirements" section: "The App requires a smartphone, a PC, and a FitBit device to function. You must register all of these devices with the Sissy App upon installation." That was easy enough. Rick had a FitBit -still in the box- given as a gift to him from a previous (and long-gone) girlfriend. Rick was not exactly in shape, and had found little use for the device. He charged up the FitBit, and installed the Sissy App on his PC. He continued reading the never-ending user agreement: "The Sissy App will provide you updates, tasks, and challenges throughout the day, however, upon installation you will be able to block off hours for work, school, and other time to ensure the App does not interfere with your life. GRA Software Corporation maintains the highest standards of information security and will ensure that the data you provide through this App is protected by robust encryption. Any photos you take through the SissyPhoto function will not be stored on your device, but will securely upload to the GRA Software Corporation server." Rick found this reassuring, and continued to (what he thought) was the end of the user agreement. "GRA Software Corporation requires a Non Disclosure Agreement (NDA) to continue with the installation of the Sissy App. This NDA will be signed by you and submitted to us digitally." Rick had never heard of an App requiring a non-disclosure agreement, and read on: "The NDA will ensure your experience with the Sissy App will be unparalleled, and also ensures that information about the App will not be leaked to GRA Software Corporation competitors or the general public. Despite the high standards of information maintained by the GRA Software Corporation, we cannot maintain the integrity of the data you provide in the event of a NDA violation." Rick paused there, noting the implicit threat in the user agreement to leak any information provided to the App if they (somehow) figured out he leaked information about the program. He had noticed, though the sissy-related forums that he frequently and desperately perused, that there had been an uptick of disclosures of sissy information recently. Many closeted sissies had their information stolen and posted to forums, revealing the men dressed in women's clothes, often in compromising positions. Rick shuddered- he did not want this to happen to him. This made sense to Rick, as he first learned about the App through comments on Tumblr and Reddit, and not any formal advertising. Comments he saw were very vague, just that the App was "amazing" and would "change your life." Rick was 28 years old, with black hair and a slight build. He had had several off-and-on relationships since graduating from a middle-tier college with a degree in business. Several girlfriends, but nothing serious. He had been alone for about 8 months in a small apartment. Since college, however, he had discovered a cornucopia of online porn that more than satisfied his need for sex- the most interesting to him, of course, being sissies. He had stumbled across sites like fictionmania and later reddit r/sissyhypno and Tumblr, which had connected him to a world of sissy porn. Rick did not consider himself gay, but was entranced with the idea of a man giving up their masculinity- often under the orders of someone else. This steady diet of porn helped him through long periods without female companionship, and introduced him to the intricate mix of websites dedicated to the publication of this material. He frequented all of them, including hypno sites, and eventually ran across some oblique comments on the Sissy App. He thought this was fascinating, having seen some rudimentary attempts at sissy training programs online already. Comments were all vague, however, which Rick now understood. He tracked down the App, which was hidden quite well on a darkweb site, and installed it. He transferred the required $300 registration fee to a pre-paid credit card, to ensure his anonymity, and downloaded it, just to see for himself how it would work. Rick decided that he had already gone this far, and electronically signed the NDA and proceed with the installation. He also finalized the user agreement, and was presented with the Sissy App Welcome Screen on his PC. A very-pink background appeared on his PC and phone as the App booted up. "Welcome to the Sissy App! Please enter your sissy name." Rick smirked and entered "Ricki." "Thank you!" "Please select if you prefer a Master or Mistress to guide you through the program." Rick selected a mistress. He wasn't gay, afterall. "Thank you!" "Please wait a moment as the App collects some data." Rick saw a spinning wheel as the App processed. "Please put on your FitBit device." Rick put it on, and watched as the App registered it. A pop-up notification appeared. "Sissy Tip: Always wear your FitBit. Never take it off unless you have to charge it. Mistress will monitor for compliance." Rick was mildly concerned about this, but another menu appeared on the App. "FitBit detected. You can access your health information from the SissyVitals tab of the Sissy App." Rick hit "OK" as another notification popped up. "Please enter height/weight data." Rick entered his 5 foot 7 inch height and 170 weight. "Thank you! Please enter sexual history data." Rick went through the menu and answered the questions. How many sexual partners have you had? 3. "Have you ever slept with a man?" no. "Have you ever had a threesome?" no. "Have you ever had a foursome?" no. " Have you ever had anal sex?" no. " Have you ever let someone have anal sex with you?" no. "Have you ever given cunnilingus?" yes. "Have you ever given fellatio?" no. "When did you lose your virginity?" 20. Rick detailed his rather-boring sexual history to the App, feeling a bit ashamed of his lack of a track record with the opposite sex. Once that was complete the App asked him about his work, how much money he made, and where he worked. It asked him about the nearest mall to his house, where he bought gas and groceries, and where his doctor's office was. Rick was given the opportunity to set the hours the App would be active. He had a 9-5 cubicle job as an insurance adjuster that more- than paid the bills, but left him unfilled. He set his "work" hours as 8-6 to cover his commute. Rick found all of this boring, as he glanced at the clock and realized he had been installing this App for the last 2 and a half hours. Finally, the App informed him the installation was complete, and that the program would begin immediately. A pop-up appeared on his phone. "Sissy Task: Take a Selfie. Use the SissyPhoto button and take a picture of yourself now. Task expires in 15 minutes." Rick jumped up-- the App already gave him something to do-- just take a picture, easy enough. He pressed the SissyPhoto button, which activated his phone camera. He took a quick selfie, was given the opportunity to review it, and then submitted it. A pop-up with a large green check mark appeared: "Competed Sissy Task: Take a Selfie. Time remaining: 11: 34. Great Job, Sweetie!" Rick exhaled. He checked out the rest of the App functions. The phone App interface was bright pink, and had several buttons on the bottom of the screen, for SissyPhoto, SissyVitals, SissyStats, and a few others that were grayed out. He clicked "SissyStats" and a menu popped up that displayed his height/weight, and several grayed out fields. As he was reviewing the other features, another pop-up appeared: "Sissy Tip: The Sissy App will provide you messages and updates during the hours you specified. Keep your smartphone close for updates!" Rick took that advice, and went to his kitchen to make a sandwich. He ate, and then settled down to watch TV in his apartment, putting on football. At about 8PM, his phone buzzed. He looked at the screen and was greeted with: "Sissy Task: Watch Porn! View a 10 minute clip of any porn you want. You must do this on your smartphone or PC, or any device you have installed and configured the Sissy App. Task expires in 4 hours." Rick chuckled. That's it? Easy. He opened up a browser on his PC, went to pornhub, and watched a blond get railed for the required 10 minutes while jerking off. He finished up, watched some more TV, and went to bed. Before he went to sleep his FitBit and phone buzzed. "Sissy Quiz: Did you orgasm? Yes or No?" Rick clicked yes, and the App opened to the main screen, where the SissyStats tab was highlighted. A pop-up stated "visit SissyStats for updates on your Sissy progress." He looked at the tab, and below his height/weight information one of the grayed-out tabs read "Last Orgasm: 10:45 SAT 1 July, 2016." Rick went to sleep with a grin on his face. The next morning Rick woke up and made breakfast. As he drank his coffee, his FitBit and phone buzzed. "Sissy Tip: Exercise is a key part of your Sissy Day! No one likes a fat sissy! You must keep an eye on your diet and exercise each day, in accordance with the instruction from the Sissy App." Rick eyed the bacon he just made, but went back to his phone. "Sissy Task: Walk one mile today. Task expires in 12 hours." "Well, that's easy enough," thought Rick, "just a mile, and maybe I can cut back on some of the junk food, would make me healthier anyway." Rick ate one slice of bacon and threw the rest away, and took a long walk in the park next to his apartment complex. When he returned he was cooling down in his living room when his phone buzzed. "Completed! Sissy Task: Walk one mile today. Great job, sweetie!" Rick liked seeing the green check mark. He hit "OK." "Sissy Task: Shave Everything. No one likes hairy sissies. You need to shave off all of that nasty body hair. Take a shower or a bath and shave your legs, arms, armpits, chest, and crotch. Sissies need razors and feminine shaving cream. This task expires in 6 hours. Do you have these available (Yes/No)." Rick recoiled. He really did not want to shave his entire body. He figured he could get around this requirement-- he selected "no" on the menu. "Sissy Task: Purchase feminine razors and shaving cream. This task expires in 4 hours." "Shit. How is the App going to know I even bought this stuff?" wondered Rick. He then glanced at his FitBit. "They could figure it out if I travel, though...." Rick's mid flew... how could he avoid this? Before he could think his phone buzzed again. "Sissy Task: Take a selfie before you go shopping. No matter what you buy, if you go out shopping you must take a selfie, every time. Mistress is watching. Take a selfie using SissyPhoto before you leave to buy your razors." Rick was concerned at this point. His mind raced-- it was a Sunday, he had to go to work the next day. He rationalized: No one would know if he shaved anything under his suit, right? He figured this would let him test the extent of the App, so he snapped a selfie, got in his car, and drove to the nearby drugstore to buy his items. Walking into the drugstore, Rick noticed the self-checkout lanes, and made a note to bee-line for them once he found the items he needed. He found some raspberry-scented shaving gel and pink razors, and quickly paid for them and left the store. Upon returning home, he took a shower, but found it very difficult to shave with the water running. Shutting it off intermittently, Rick shaved his toes, legs, chest, and armpits very slowly and carefully. He then (carefully) shaved his balls and his cock. Rick had never shaved his ass before, and shaved around it, but avoided anything directly near his asshole. He emerged from the shower denuded, and rubbed some lotion he bought at the store over his newly-shaved skin. He had never felt the smoothness that his legs and chest had now, and actually enjoyed it. His phone buzzed a few hours later. "Sissy Quiz: Did you buy the required shaving items?" Yes. Rick selected. "Completed: Sissy Task: Purchase feminine razors and shaving cream. Good job, honey." "Sissy Quiz: Did you shave Everything? legs, arms, armpits, chest, and crotch?" Yes. Rick selected. "Verification required: Take a selfie of your full body (with face), and a closeup of your cock." Rick panicked, but realized he had followed the instructions. He took the required selfies and submitted them to the App. He breathed a sign of relief and tried to enjoy the rest of his weekend. He made dinner and watched a movie, when his phone buzzed later in the evening: "Sissy Task: Watch Porn! View a 10 minute clip of any porn you want. Task expires in 4 hours." Rick obliged, and watched a few clips of lesbians banging each other with strapons. His phone buzzed right before he fell asleep: "Sissy Quiz: Did you orgasm? Yes or No?" Rick selected "Yes." Two days with the App and it seemed to focus on physical fitness and porn. He became very excited as he received a cascade of green checkmarks for his completed tasks at the end of the day, their "ka-ching" tone was especially pleasing to his ears. Rick thought this wasn't the worst App he ever downloaded, and resolved to stick with it a while to see where it went. He checked out reddit comments on users of the Sissy App, which were very few and not descriptive (probably due to the NDA), but effusively positive. Rick went to sleep, unsure of how this would all work with his full time job. Week 1. Rick's FitBit buzzed him awake at 6AM, his phone stating stoically: "Sissy Task: Walk 2 miles. This task expires in 2 hours." Rick groaned and rolled out of bed, put on his old running shoes, and followed the App's instructions. Rick was never an "in shape" person, had a bad diet, and never really focused on his health. He walked 2 miles around the park next to his apartment complex, and returned at 6:50, took a shower, and went to work. True to the App's user agreement, it did not bother Rick during work hours, which drug on forever for Rick, who was eager to get home to see what was in store for him next. Rick arrived back at his apartment at 5:45. He changed out of his suit, and flopped in front of the TV. His phone buzzed at 6:15. "Sissy Task: Shave Everything. No one likes hairy sissies. Take a shower or a bath and shave your legs, arms, armpits, chest, and crotch. This task expires in 4 hours." "Sissy Tip: Ladylike Diet: Remember, no one likes a fat sissy. Look at what you are eating, and make sure you have a small amount of protein (a chick breast or fish), some vegetables, and fruits. Stay away from anything processed, sugars, alcohol, and unnecessary fats." Rick was concerned about this, but quickly thought: "How is the App going to know what I eat?" Rick figured he could easily keep eating what he pleased, but the photo requirement would necessitate him continuing the shaving regimen. He took a shower and shaved, ate a quick dinner of leftover hotwings and sliders, and plopped back down in front of the TV. The App buzzed again, requesting a selfie of his shaving results. Rick complied. "Sissy Task: Watch Porn! View a 10 minute clip of shemale porn. Task expires in 4 hours." Rick raised an eyebrow at this, but figured "what the heck." He had viewed tonss of shemale porn in the past, and it was prominent on Tumblr and Reddit sites he visited. He opened his browser on the PC and viewed the clips as required, masturbating furiously. "Sissy Quiz: Did you orgasm? Yes or No?" Rick selected "Yes." and was about to go to sleep when his phone buzzed again. "Sissy Task: Watch Sissy Hypno! View the provided hypno videos in the Sissy App on your PC. Use headphones, dim your lights, and ensure there are no noises or other interference with your experience. Task expires in 2 hours." Rick, surprised at this new requirement, went to his PC and opened the links. He sat in the comfortable chair in front of his widescreen 20 inch HD monitor, put on his Bose headphones, and watched the videos the App provided. Rick had seen some of this material spliced up in other hypno vids he watched online in the past, but the underlying soundtrack in the one he watched tonight transfixed him. Par for the course, the hypno vid hit themes of "obey your mistress," "you are a sissy," and "submit," nothing Rick had not heard before in other "hypnos" he had run across on the Internet. After completing watching the one hour video series- which seemed to flash by in no time- a green check mark popped up. "Completed: Sissy Task: Watch Sissy Hypno! Good Job, Fairy!" Rick made his way to bed and fell asleep, unaware that his computer speakers seemed to emit a constant noise at night while the Sissy App was open. The rest of the week fell into a pattern. Exercise in the mornings. The App alternated walking, running, and in-place exercising every day. On Tuesday, the App guided Rick through a set of lower-body and abdominal exercises, which left him winded and sore the next morning. Rick was doing squats, bended knee lifts, lunges, crunches, and other exercises at 6AM, per the App's instructions. 2 mile walks evolved to 1 mile run & 1 mile walks, to 2 mile runs & 1 mile walks. The App, obviously using FitBit data to track compliance with the exercise regimen, monitored Rick's successful completion of these challenges, and awarded him the coveted green check marks for completing his assignments. Rick became ecstatic each time he saw the green check marks animating in the App. The App continued to leave him alone at work, but would routinely buzz around 6PM, tasking Rick to do his daily shaving, porn, and hypno watching. The hypno video and audio files left him zoned out after watching them, having much more of an impact than the usual sissy hypnos he had previously viewed online. The files used trance music coupled with multiple tracks of feminine chanting that Rick could barely make out. "Submit. Submit to all of the tasks the App provides. Good sissies submit to the App. You are a good sissy. Good sissies obey their Mistress. Good sissies obey the App...." On Thursday, Rick got an notice: "Sissy Audit: Mistress reviewed your activity and on FRIDAY 7 July 2016, Ricki went shopping without providing selfie. Sissy is reminded to ALWAYS provide a selfie prior to shopping. Results of this audit: Sissy is required to do 100 extra squats as punishment. This task expires in 1 hour." Rick was incensed-- what was the App talking about? He thought back to what he had done that day, and realized he had gone to the gas station on the way back from work. Had the App figured out his routine already? His legs sore already from the previous day's lower-body workout requirements, Rick did the required exercises and updated the App, the FitBit, no doubt, providing confirmatory data. After one week using the App, Rick had gotten use to the exercise, the shaving, and the porn watching requirements. Rick got a bit of a thrill knowing that he was connected to this as-yet-unseen Mistress that was guiding his actions, but knew that most of the day-to-day requirements he was completing were from a software program. The fact that he was-in reality- submitting to a machine made the entire enterprise a bit hotter for Rick. He complied with all of the other instructions given by the App, and fell asleep on Sunday night as usual to the hypno files. "You are a sissy slut. Sissy sluts submit to Mistress. Anything the App tells you to do, you will do without questioning. Questioning the App is Bad. Good sissies do not do Bad Things. Questioning the App is Bad. Good sissies do not do Bad Things. Good sissies obey Mistress... Week 2: Rick's FitBit buzzed him awake on the Monday morning of his second week in the program, instructing him to do a series of squats and ab exercises. The App displayed several videos of fitness models doing various squats and leg raises, all wearing tight yoga pants or booty shorts. Rick got through them, wearing old gym shorts and ratty t- shirts. He showered, got dressed, and went to work. When he got home, the App buzzed him, asking: "Sissy Quiz: What type of workout clothes should a sissy own?" Rick hit OK and proceeded. "Should a sissy's workout clothes be loose, or skin tight?" Rick selected "skin tight." "Should a sissy's workout clothes be dark colors, or bright colors (and almost always pink!) Rick selected "bright colors (and almost always pink!)" "Sissy Task: Provide a photo of your workout clothes. This task expires in 1 hour." Rick quickly figured out where this was going, and used SissyPhoto to snap a picture of his workout clothes. He knew that he would be instructed to buy new workout clothes eventually, and stood by for the order. Rick went to work as usual during his second week in the program. No major changes or updates occurred, but on Friday he did get a message: "Sissy Task: Buy new workout clothes. Buy 3 sets. Tops and bottoms should be skin tight, and in bright colors, almost always pink. Take a selfie in one of your new outfits. Task expires in 4 hours." Just home from work after a long week, Rick groaned, but got himself together to go to the mall to buy the required items. Just as he was heading out the door he remembered the selfie requirement, and snapped a selfie in the mirror by his door in his small apartment. Rick went to the nearby mall and went to an athletic apparel store. He quickly perused the female section of the athletic apparel and selected a few outfits he thought met the standards the App outlined. 3 small t- shirts, pink, pink sweat bands for his wrists and head, 3 pairs yoga pants, skin tight medium. Rick quickly bought the items, the cashier looked completely detached and uninterested. He returned home and quickly unpacked his purchases, putting on one of the female small pink t-shirts and taking off his pants and underwear and donning the black yoga pants. He looked at himself in the mirror, chuckled to himself, and took a selfie, submitting it to the App. "Sissy Tip: Always exercise in your sissy apparel! You never know when Mistress will request a photo!" Rick grimaced and took note of the tip. He listened to his required hypno files, watched shemale porn as directed, and went to sleep. "You love to exercise in your girly apparel. You will not notice people staring at you. Your sissy apparel is the most comfortable exercise wear you have ever worn. You will feel odd and strange wearing loose baggy exercise clothing. You want to wear tight clothing when exercising. Skin tight. You want to wear bright colors when exercising to ensure visibility. Pink is an ideal color to wear. All sissies love to wear pink. You are a sissy. Sissies obey Mistress....." The rest of the week went normally until Saturday, when his phone buzzed. "Sissy Task: Purchase Panties. Go to the mall and buy 6 pairs of pink panties in your size- the sexier the better! Provide a photo of your newest pair! Task expires in 4 hours." Crap. Rick was looking forward to a tranquil Saturday. Instead, he quickly got dressed and headed to the mall. Once there, he bee lined to Victoria's Secret and searched for the underwear section. Never having looked for underwear for one of his girlfriends, this was a new experience for Rick as he entered the store and began to look around in the darkly-lit store. A perky blond salesgirl approached him and inquired "sir so you need any help, what are you looking for?" Off balance, Rick replied, "I'm, um, looking for a present for my girlfriend... underwear...?" It ended like a question even though Rick meant it as a statement. The blonde salesgirl smiled, "of course! What are you looking for? A thong, brief, high-waist-cut, or bikini cut brief?" Rick didn't know any of those terms, but knew what a bikini was and went with that. "Yes," he stumbled, "a bikini-brief. A few of them if they are available." The blond salesgirl smiled again, "You betcha! I've got a nice selection over here." She directed Rick to a bin under one of the store's display tables that had various assortments of panties. Rick quickly selected briefs that he thought would fit him- large- and quickly paid and left. Once back in his apartment, he put on a pair of the pink panties, and snapped a selfie with the App. Minutes later, his phone buzzed. "Sissy Audit: Mistress reviewed your activity and on SATURDAY 13 July 2016, Ricki went shopping without providing selfie. Sissy is reminded to ALWAYS provide a selfie prior to shopping. Results of this audit: Sissy is required to skip the next meal as punishment." Dammit! Rick couldn't believe he forgot again to snap a selfie before leaving the house to shop. He made a mental note to not forget this again, as the App was obviously using the location data provided by his cell phone and the FitBit to track his movements. This was more pervasive than he realized... At the same time he wondered how the App would know he skipped a meal, but decided to forgo dinner just in case. He did his required hypno and porn watching and went to sleep. "....always wear your panties. Good sissies wear panties. Panties are worn at all times. Obey your Mistress. Mistress commands you to wear panties....." The next day, Rick was shaken awake, hungry, by his phone's buzzing. "Sissy Task: Throw out your male underwear. You will only wear your panties from now on. If you need more, you will buy more. You will not wear male underwear again. You will provide a photo of your male underwear in the trash. Task will expire in 1 hour." The buzzing woke Rick up early Sunday morning as he read the pop-up message. His underwear drawer had the usual mix of boxer shorts and other male underwear. The new feminine underwear he purchased yesterday were still in the pink striped Victoria's Secret bag by his bed in his apartment. "what is the App going to really know here," Rick thought. He took a handful of his oldest underwear, and tossed it in the garbage, snapping a photo of it with SissyPhoto. He stashed the rest of his boxers in a bag in his closet, and put the VS undies in his underwear drawer. Rick then did his required exercise for the day, a 2 mile run and 1-mile walk in the park. He wore his (tight) pink t-shirt and yoga pants, which earned him a few stares from men and women alike. Rick noted this, but for some reason was not overly concerned about it, and decided to stick it out. Later, he went to the grocery store in his street clothes (remembering to snap a selfie before leaving) and bought some food for the week, buying lean proteins like chicken breasts and tilapia, as well as a range of veggies. Rick returned to his apartment, ate dinner, watched his hypnos, and stood by for his normal evening porn task from the Sissy App. When it arrived, it raised his eyebrows: "Sissy Task: Watch Porn! View a 10 minute clip of gay male porn. Task expires in 4 hours." Rick had never watched exclusively gay porn before, but the App had made its pronouncement. He opened a browser on his PC, went to pornhub, and complied. With some embarrassment, he awaited the next popup. "Sissy Quiz: Did you orgasm? Yes or No?" Rick sheepishly selected "yes" and went to sleep, listening to his soft hypno tracks. Week 3. The third week in the program proceeded as Rick expected it to. He continued the shaving regimen, and submitted the required photos of his bare form. He became more and more comfortable with not having body hair, and began to enjoy the smoothness of his legs and chest. He continued following the diet and exercise guidelines of the App, and was required to re-submit his weight data on a weekly basis. Rick weighed himself and found that he was now at 160 pounds- down 10 pounds from 3 weeks ago. The SissyStats tab had updated fields now not only on his last orgasm dates, but also his clothes, stating that he was in panties. His workouts remained challenging but constant, requiring many hours of sweat to successfully complete. Rick noticed his legs and abs becoming more defined while the lack of weights to his upper body resulted in muscle atrophy and leaner arms, shoulders, and chest. His diet was also improving his mood at work, making him more engaged and energetic. Rick continued to listen to the hypno files and videos each day, as well as adhere to the instructions for viewing porn in the evenings. It remained a mix of shemale and gay porn, which Rick voraciously consumed. Rick loved seeing the big green check marks on the App, and relished in completing each challenge the App laid out for him. He became religious in snapping selfies before leaving the house, just in case he went shopping later in the day, and took more care in his appearance each time. Then he received a package in the mail. "Sissy Task: Open your package." Rick hesitantly opened the package that arrived on his doorstep. He opened the nondescript cardboard box - it was a small box that contained a "CB 6000" chastity device in its packaging. The device itself was a series of clear plastic rings with a piece obviously meant to fit over the penis. The device had some sort of computer chip appended to it by its locking mechanism. The package also had a series of small numbered locks. Rick looked at all of this and immediately had serious second thoughts about his downloading of the Sissy App in the first place. Before these thoughts could percolate, his phone buzzed. "Sissy Task: Put on your chastity cage. This task expires in 15 minutes." Shit. Rick immediately began fiddling with the instructions, and started to move the required rings over his shaved pubis, shoving one smooth ball, and then another, through the base ring of the chastity device. After that, he put in the required rods, and attached it to the piece meant to fit over the head of his penis. His only problem was that he was so turned on by the process, his penis had become erect in the chastity cage. Rick nervously glanced at the clock, showing only 5 minutes left for this task. His mind raced- what could he use to reduce his erection? Ice! He ran to the freezer and grabbed a handful of ice cubes, applying them directly against his cock- which shocked his senses but began to reduce the erection. 3 minutes. Rick fumbled with the rods and finally got the main piece in line, snapping it into place and locking it. He took a photo and submitted it to the App. His phone buzzed "Completed: Sissy Task: Put on your chastity cage. Good job, Slut." "Sissy Audit: Mistress reviewed your activity and Ricki failed to secure her chastity device in time. Results of this audit: Reading assignment: Sissy is required to read this month's Elle magazine and answer questions to determine compliance. This task expires in 1 hour." Shit shit shit. Elle magazine? What the hell is that? Rick knew he had to go buy it, which meant going shopping. He threw on his pants and a t-shirt, remembering as he rushed out the door to snap a selfie with SissyPhoto, and raced to his car. He quickly bought the magazine at a nearby Barnes and Noble bookshop, and stayed in the shop reading as much as possible as the minutes clicked down to the task's completion date. The fact that a nervous young man locked in chastity was obsessively reading a women's fashion magazine in a bookstore on a Saturday afternoon drew little attention, despite Rick's racing mind. His phone buzzed at the hour mark. "Sissy Quiz: press to continue." Rick pressed the notification and was greeted with a 40 question quiz on this month's Elle magazine. He was asked specifics on makeup shades, dress colors and lengths, hairstyles, and numerous questions on high heeled shoes prominently featured in the magazine. Luckily he had the magazine right there and frequently referred to it, flipping through it repeatedly to address the questions the Sissy App put to him. Finally, a pop-up appeared. "Completed: Sissy Quiz: 35/40 questions answered correctly. Good job, sweetheart- hope you enjoyed those high heels. Take the magazine with you." Flustered, but with a huge sigh of relief, Rick composed himself in the bookstore and stood up to leave. His cock stirred in his pants against the chastity cage, and he was exceptionally horny after this latest trial. "I can just take this thing off when I get home," he thought. As he was leaving, a voice caught his attention over his shoulder. "I've never seen someone read Elle that intently before, are you in the fashion industry?" Rick turned around and noticed a lovely 5 foot 8 brunette with large blue eyes staring at him. She wore dark stockings with a gray skirt and suede heels, along with a blue tight sweater top and a colorful red scarf. Rick sputtered. "umm, no, I'm just trying to keep up on the latest trends, for the fall." The brunette shot him a quizzical look, but smirked. "Well, my name is Mona, and I'm a women's fashion designed. I'm not sure what you do Mr...." "Rick! Rick Matthews." "Mr. Rick Matthews, but if it involves ladies fashion and fall, I'm interested. I run a small boutique in town, but I'd love to be in the pages of Elle one day." She slipped him her office's card, "Restricted Fashions"--Stop by if you'd like to see more." She spun around and sauntered off, her well appointed figure lingering in Rick's field of view. Rick gulped as he wisher her goodbye, but his mind quickly focused back on the task at hand: this damned App! When he got back to his apartment, he breathed a sigh of relief, when his phone buzzed. "Completed: Sissy Task: Put on your chastity cage." Thank God I finished that, Rick thought, pausing to wonder how the App knew he put on his chastity device. He wondered if the chip in the cage somehow sent a signal to the App. He wasn't sure... "Sissy Tip: You chastity device has a numbered lock to correspond to your key. To verify your chastity, you must provide a picture when you lock your device, showing the locked device with the numbered lock visible. Next, you must place your key in a glass of water -the amount of which will be determined by your chastity length. That glass must be placed in your freezer, and is subject to random inspections while you are locked in chastity. To summarize, each time you are locked in chastity, you must submit 2 photos: one of your device, and one of the key in the required amount of water in your freezer. "Sissy Task: Lock yourself in chastity for 24 hours. Freeze your key in 1/4th cup of water. Submit a photo of the locked device with the numbered lock visible, and a photo of the key in the required amount of water in your freezer. This task expires in 15 minutes. OK, Rick thought, easy enough, he already had the device on. He ditched his jeans and went into his bathroom, trying to get a good angle on the clear chastity device hugging his shaved pubis. He snapped the photo and submitted it in the Sissy App, and then went to his kitchen, grabbing a glass measuring cup and placing the chastity key inside, filling it to the ?th cup level. He placed it in the freezer, took and submitted another photo, and collapsed on his couch. "What the hell am I doing?" thought Rick. "I'm driving myself nuts here over some piece of software... who knows if there is even a real Mistress on the other end? I should just stop this now..." Rick realized that the thought was counter productive-- he was extraordinarily horny, and had only been doing the program a few weeks- - who knows where this could take him? Plus, he was healthier than ever. His phone buzzed, distracting him from his misgivings. "Sissy Task: Watch porn! Watch any porn you want for 30 minutes. This task expires in 4 hours." Rick groaned-- he was locked in chastity! How could he watch porn and beat off with his dick locked? He examined the cage around his shaved cock, which tightly compressed and hugged his penis against his torso. There was no way he could get erect with this on. He could just unlock it, though... He glanced at the fridge, knowing the key was still in the freezer and probably not yet even frozen. Rick paused... maybe this was the App testing him. He decided to give it a chance and follow the instructions-- he'd get to take the cage off tomorrow anyway. He opened his browser and started perusing hot blondes in latex for the required time. After finishing, he took a cold shower, and put in headphones listening to his sissy hypno track as he went to bed. The track was relaxing, with a meditation-spa theme with a barely audible female voice chanting in the background. "you are a sissy. Sissies comply with their instructions. You will obey your Mistress. Sissies wear panties, bras, and stockings. Sissies take the utmost care in their personal appearance. You are a sissy. You will take the utmost care in your personal appearance. You will have your nails done. You will have your hair styled. You will wear the sexy, feminine outfits your Mistress chooses...." Rick awoke to his buzzing FitBit again and followed the App's instructions through a grueling squat and leg raise routine, finishing with situps, ab extensions, and crunches. He wore his yoga pants and tight pink t-shirt , sweating through both of them on the floor of his apartment. He showered, shaved, and went to work. He found it difficult to focus at work with his dick locked in the chastity cage, as each glance from a female coworker led Rick to believe they had somehow figured out his secret. Linda from accounting pulled him aside to ask several technical questions on a recent report he submitted, and Rick stumbled over himself to respond, finding himself fixated on her makeup, tits, dress, pantyhose, and high heels. Finally, 5PM rolled around and Rick got ready to leave the office. His phone buzzed as he was getting up from his cubicle. "Sissy Task: Verify compliance with the dress code: Provide a photo of your sissy panties. This task expires in 1 hour and 2 minutes." Rick sweated-- I thought the App wasn't supposed to contact me during work hours? He ran to the bathroom, slamming a stall door shut. OK, Rick thought, I'm following the instructions, I've just got to get this done and go home. He pulled his pants off and snapped an awkward selfie with his super cute (super cute? Where did that come from?) Victoria's Secret pink panties with black polka dots. Someone else was in the bathroom, so Rick waited to for him to leave before exiting. Back at home, Rick changed clothes and flopped on his couch, turning on the E! Network to watch the latest celebrity gossip. He kept an eye on his phone, which buzzed an hour later. "Sissy Task Completed: 24 hours in Chastity: Unlock yourself." Elated, Rick took the glass out of the freezer and ran it under hot water in the sink. As the small amount of ice thawed, he saw a new update in the App. A red dot with a "1" in white lettering appeared over the SissyStats menu. He checked it and he saw new previously- grayed headings were available, including "Total time in chastity- 24 hours," "Current Status- unlocked." the App buzzed. "Sissy Task: Watch porn! Watch gay porn for 30 minutes. This task expires in 1 hour." Oh come on! As Rick impatiently waited for the water to melt the ice, he vented that the first porn he would watch as he relieved a day's worth of stress was 2 dudes. Screw this, Rick thought, how is the App going to figure this out? The key was finally free from the ice, and Rick quickly unlocked his CB 6000, pulled his chair up to his computer, and was jerking away to a hot tattooed brunette getting railed within 5 minutes. Finishing up, Rick flopped back on his couch to finish out the night peacefully watching his TV. Suddenly, both his FitBit, Smartphone, and PC dinged. "Congratulations! 30 Days in the Sissy App Program!" Rick hit OK on his phone in the App. Another pop-up appeared. "Its been a long road, but you've been doing great! Your SissyStats and SissyVitals report tremendous progress! You've lost 15 pounds since beginning the program, and are on track for even greater success! Mistress is proud of you! More challenges lie ahead, keep up the good work!" Rick was gratified as he saw the App praising his progress. After dismissing the notification, a new alert popped up: "Privacy Escalation Request: The chastity device you wore this week was purchased with the $300 down payment required for App registration. Many other purchases will be required for you to successfully complete the SissyApp program. While the App can provide you the links and product information for future necessary equipment, it will vastly improve your user experience if SissyApp makes the purchases on your behalf! Just like your chastity device was securely ordered and delivered to you, all purchases for subsequent equipment will be through the Sissy App secure servers, and will arrive to your home in nondescript packaging. We will require your credit card information, but the Sissy App- via the SissyChat function- will update you each time a purchase is made. You can cancel, provide new card information, or adjust this at any time. Please make a choice." Good sissies submit to the App. "Where did that thought come from?" Rick thought. The logic made sense, he did not want to have to order any of this sissy stuff on his regular Amazon account. He clicked through the "account update" menu in the Sissy App and entered his credit card information. A new menu item appeared in the bright pink App- SissyChat. 2 new notifications were available- Rick clicked on it, and it appeared to be a WhatsApp-like interface for messaging. 2 messages from SissyApp Admin were waiting- one congratulated him for registering his credit card, and another informed him a $121 dollar purchase was made on his behalf. Rick wondered what that was... but, still basking in his post-orgasmic glow he put his headphones in and listened to the sissy hypno track provided by the App and dozed off on his couch. "All sissies obey their Mistress. You must obey your Mistress. You must wear your chastity belt when Mistress commands you. You must dress in sexy clothes to please men. You must wear panties, bras, stockings, and heels. You are a sissy...." Week 4. Rick's weekend flew by and he found himself back at work on Monday morning. The App continued to track and progress his exercise routing-- that morning he had run 3 miles and had a light breakfast of some fresh fruit and black coffee. Later in the day, he checked the SissyApp and saw a new menu item appeared: SissyCalendar. He clicked on it and saw an update for the coming Friday "Sissy Date." He stopped in his tracks, suddenly sweating, and clicked on the calendar entry for 7PM on Friday. It read "Date with Candi." Under additional information, it only displayed: "Information will be updated on Friday." Who was Candi? What was this? Rick became very worried, and thought about it non-stop on his way home from work. No additional advice was forthcoming from the App. On Wednesday, Rick received another troubling update: "Sissy Task: Lock yourself in chastity for 72 hours. Freeze your key in 4 cups of water. Submit a photo of the locked device with the numbered lock visible, and a photo of the key in the required amount of water in your freezer. This task expires in 15 minutes." The chastity device had sat unused in his nightstand for the last few days, but Rick quickly dug it out and snapped and locked it in place, much faster than his initial attempt. He submitted the required pics to the App. He then looked at the calendar and his clock. "I'm going to be locked up during the date?!" He said aloud. Rick languished in the device for the rest of the night, and all day Thursday and Friday. The App still required him to watch porn each night, and to listen to the increasingly unnoticeable sissy hypno tracks. Rick found himself listening to the techno sissy hypno tracks during his morning workout routines anyway. Rick found himself frustrated, on-edge, and desperately waiting for a release. On Friday afternoon, his phone buzzed, indicating an update on SissyCalendar. It read "Date with Candi- 7PM, Starbucks on 224 Sycamore Street. Wear Pink." "Sissy Tip: Sissies love to go on dates, even if it is with another sissy! Sissies must be supervised while together by a Mistress or Master, as they tend to fuck and suck each other (and anyone else!) when left unattended! Dates between sissies will be chaperoned by Mistress via the SissyApp." Rick was nervous- he had not been on a date in 8 months- and the last one was with a girl! He drove home quickly, and when he got into his apartment, his phone buzzed. "Sissy Tip: Dating can be stressful for sissies, but just remember to relax and have a good time. Mistress will be watching and will provide you instructions as needed. If this is your first date, just try to get to know one another." Rick looked through his clothing and could not find anything pink other than the workout t-shirts. He glanced at the clock- just after 6PM. He knew the mall was across the street from the Starbucks, and quickly snapped a selfie and hopped in his car. At the mall, he quickly bought a pink button-up dress shirt, tucked it into his slacks, leaving his gray dress shirt he wore to work that day in the changing room. He arrived at the Starbucks a bit flustered and flushed, but at precisely 7PM. He glanced at the buzzing SissyApp, which displayed an updated SissyCalendar. The calendar invite displayed Candi's SissyStats! It included her(?) height/weight, last orgasm (Tuesday), Current chastity status (locked), and the menu noted panties, bra, and stockings (Rick's only had panties... he thought). Engrossed, he saw that a selfie from Candi was also in the Calendar update, a fresh-faced girl(?) in a tight pink polo shirt. He snapped his head up as he looked around outside of the Starbucks- "If I have Candi's SissyStats, she has mine!" Rick realized. He did not see Candi outside, and ducked into the coffee shop. Rick quickly spotted Candi in the corner and went over to introduce himself. Candi stood up, a with a thin frame, probably about 120 pounds at 5 feet 5 inches. She had a slim frame, with A-cup breasts, and long brown hair with streaks of blond highlights. Her face was made up, with eyeliner, dark eye shadow, and pink lip gloss. She was dressed in tight tan pants with the pink polo, wearing high heeled brown sandals and a FitBit with a pink band. "Hi Ricki, I'm Candi. That's not my real name, you know." He said in a low tone. They ordered iced coffees and sat down in the quiet corner of the shop. "Is this your first date on the App?" Ricki asked. "No," Candi replied, "I've been on few others. The App uses location data -I think- to pair up sissies that live nearby. I live right over on Maple Ave." Rick knew the apartment complex- Candi was about 10 minutes away from him. "Why did you download the App?" Ricki asked. "I don't know, but I've been using it for 6 weeks. It totally changed my life. I'm more in touch with myself now than I've ever been. I'm getting out and meeting people, I'm in great shape... it just required some... tradeoffs." Rick knew the answer to the question, but asked it anyway, "What tradeoffs?" "The ability to control your own life. I tried to control my own life, I ended up with a dead-end job, no girlfriend... All I had to do was submit to Master and now I'm happy and focused!" "Master..." Rick repeated... "have you met him?" "Oh no, you don't get to meet your Master or Mistress until you've proved yourself to the Program. We're like not even close yet, I think." "Your SissyStats... you're... locked up right now?" Rick whispered. "Oh yeah. Sissies aren't allowed on dates with each other if we're not in chastity." Candi replied. She tapped her phone, "Master is listening right now. He listens to everything. We need to be chaperoned to ensure we behave..." Candi eyed Rick up and down. Rick sipped his drink, glancing nervously at the open SissyApp on his phone. "How does the App know we.... do the tasks... the ones where it might not be able to know?" Candi looked at him directly, her blue eyes highlighted with a very subtle sparkle of some kind on her lids. "The Program knows. Sissies must submit to the Program." "Does it... make you fuck random people?" Ricki asked nervously. "The App doesn't make you do anything," Candi laughed, "it gives you tasks and challenges. Some of them you complete, some you can't. It's about you as a person, drawing out what's really inside, you know." Rick was slightly relieved by the answer, but also wondered what exactly the App would draw out of him if he stuck with it. Candi and Ricki continued to chat for over an hour, when both of their phones buzzed at the same time. "Sissy Task: Wrap up your date. Don't forget to kiss goodnight." "Master doesn't let dates go on too long," Candi said, "especially first dates. I had a nice time talking with you, Ricki, I hope we get to see each other again." "Likewise, Candi, thanks for spending time with me." They glanced nervously at each other as they rose to leave. Outside of the Starbucks, Candi stepped in close and gave him a kiss on his cheek, which he reciprocated. "Good night, sweetie." She(?) made her way into the dark parking lot. Rick exhaled-- He had found the date both exhilarating and deeply confusing. It felt so good to share his sissy desires with someone else- even a random stranger from the Internet- and discuss his deepest secrets with someone openly. He had girlfriends in the past, but never felt like he could discuss the aspects of his sissy indulgences and interests. As he drove home, he replayed the meeting in his mind. Once at home he quickly opened the SissyApp to determine how much time he had left in chastity, pulling out the bowl from the freezer and running it under hot water as soon as possible to obtain the key. When the timer on the App clicked from 00:01 to 00:00, he unlocked himself and desperately masturbated to clips of two shemales fucking each other. He thunderously came after his 5 days in chastity. "Sissy Quiz: Did you orgasm? Yes or No?" "Hell yeah, I did," Rick thought triumphantly, basking in post-orgasmic bliss. He clicked though the next Sissy Assignment to listen to his required hypnos, and and quickly went to sleep listening to trance music softly thump. In the background, he barely heard the chanting. "You love other sissies. Other sissies are your best girlfriends. You trust other sissies. You can tell them your secrets. Other sissies love you, and want to play with you. Sissies are your girlfriends. Sissies are sexy. Mistress commands you to date other sissies when she pleases to please her. You must obey your Mistress...." The next morning Rick awoke and went through his exercise and shaving routine, but was looking forward to relaxing after a long frustrating week in chastity. He paused after his shower and admired his reflection in the mirror. The Program was really showing results, he had dropped quite a bit of weight, leaving him at 155 pounds, but he had lost quite a bit of muscle and definition in his upper body, as he strictly followed the App's guidance to avoid lifting heavy objects and focus on stretching and flexibility in his workout routines. His legs, however, were more well-defined now, and his stomach started to show some definition around his abs. Rick put on a pair of jeans over his panties and turned on the TV, eating a handful of strawberries as his only breakfast. His phone buzzed. "Sissy Assignment: Buy a bra. 4 pink or flesh-colored bras, to be exact, at the local mall. This task expires in 6 hours." Rick rolled his eyes, "I guess I should have known this was going to happen eventually." He grumbled. He paced his apartment deciding his next move. This was almost stereotypical of sissy stories he read online. Sissy gets sent to the lingerie shop and gets humiliated by the shop girls as her Mistress watches. Shop girls torture the sissy as she is strapped into more and more lingerie, stockings, corsets, heels, and long opera-length gloves. They force the sissy down at a vanity and attach a long blond wig to her head, then they do her makeup, then before you know it she's fucking and sucking... Rick paused, as his fantasy was playing out a bit quicker- and smuttier- than he imagined. He also noted his rock hard cock. He had to deal with both of these situations. A few pornhub clips, a selfie, and an hour later, a flushed Rick arrived at the local mall and headed into Victoria's Secret. He had the entire story planned out in his head, and he watched several online videos on bra sizing. He had measured his chest size before he left, and he would just tell the shop girl that he was buying a few pairs for his girlfriend. That was believable, right? Guys buy lingerie for their girlfriends all the time. He was greeted by a perky salesgirl at the door, and he quickly found a table with bras and looked through it, finding his size. Grabbing the smallest cup size that matched his chest measurements, he headed to the register to pay. With his back story ready, he approached the blonde cashier with trepidation, she eyed the pile of bras he laid on the table. And rang them up. With heavy undertones of boredom, she completed the purchase and roboticly called out "next in line." Rick was out of the store with his bag of bras in 8 minutes. That was it? Too easy, he thought. He made his way out of the mall when his phone buzzed again. "Sissy Assignment: Meet and Greet! The SissyApp has detected another sissy in your immediate area. Go say hi! This task expires in 15 minutes. Meet at a central location, like the JAMBA JUICE." What the hell? Rick looked around, not knowing how the App figured this out or what to do next. He glanced at his FitBit, and realized the geolocation software must have matched them together. "Sissy Tip: You'll meet many sissies through the SissyApp. Mistress directs you to always greet new sissies with "hello sweetheart." They will reply back, "hi sweetie." This is how you know you are approaching fellow sissies. "Sissy Tip: shaking hands is fine when initially meeting fellow sissies (you'll soon be doing more than that!) but you MUST hug sissies you have met before, for at least 5 seconds (no cheating, Mistress is always watching!). "Sissy Tip: sissies always hug and kiss each other goodbye." He looked back at the Sissy App, and say the SissyCalendar had an alert. A new appointment had appeared for the "Meet and Greet" task- he clicked it and pulled up the SissyStats card. "Haley. last orgasm (Friday), Current chastity status (locked), buttplug (small), panties, bra, and stockings." the photo was of a girl(?) with a smooth face, long blonde hair, and a green shirt. He looked around, and quickly saw the sissy holding a smarthone similarly looking round. She had on tight dark pants and high heeled black leather shoes, with a tight green shirt that closely hugged her B-cup breasts. "Hello sweatheart." Rick said a bit awkwardly. "Hi sweetie!" "Haley" energetically replied, shaking his hand. Rick noticed the finely manicured nails with a clear coat of polish. "Ricki it is soooo nice to meet you, what are you up to today?" Rick(i) glanced down at his bag. "I'm buying my first bra, the App told me to do it this morning." "How do you know it fits? Did you try it on?" Rick decided to mis-direct, as he saw the sissy was really, really, excited to see him. "ummm... no but the salesgirl was nice. I sized it at home," "OhmyGod, you have to try it on before you buy it? Did you go to Vicki? Which girl was it? Sylvia the brunette, she's great! Or was it Donna? Michelle?" "umm... I'm not sure..." "Come here- we've got to see if this fits or not, we might as well, right girlfriend!" The last word stuck in Rick's head for some reason and he lost focus for a second, long enough for Haley to grab his arm and pull him into the nearby bathroom. "let me help you with the shirt." Haley said, pulling Rick's dark t-shirt over his head and looking at his smooth chest. "you look great! What are you, like 5 weeks on the App?" He grabbed the bra and fitted it around Rick, fitting the clasp in the back. He stepped back to observe. "Not bad! You should get some other colors, you know, for variety. Once you get home the App will tell you to start wearing them every day." "every day!?" Rick said "what about work?" He knew a bra would be visible under his work dress shirt. "No, Mistress knows we need to maintain our day jobs until we're further along in the Program. You do need to wear one at all other times though. See, mine's on now." He placed Rick's hand on his chest and he felt the bra. His phone buzzed. "Uh Oh, we're almost done here, Meet and Greets are only supposed to be 15 minutes and one of us is unlocked today!" He winked at Rick, "Lucky you! I'll say goodbye, come here." Rick hugged the sissy for what he felt was a bit too long, they pecked each other on the cheek, and Haley slipped out of the bathroom leaving Rick stunned and confused by himself in a stall with a pink bra on. "what the hell... just happened?" Rick thought. His phone buzzed with green check marks on his successful completion of the Meet and Greet task. Dazed and unsure of himself, Rick headed home, pink bra on under his t-shirt. The following day Rick awoke to a buzzing SissyApp. He had a message in SissyChat saying that 48 dollars had been billed to his credit card, and he had a SissyCalendar appointment for a nearby salon. The calendar said to dress appropriately, whatever that meant. Rick assumed that meant bra and panties, following his chat with Haley yesterday. He took a selfie and headed out. At the salon, he checked in with the receptionist. "Are you Ricky? We've got your appointment information right here, come on back." Rick was surprised, but assumed the App (or someone? Mistress?) had made the appointment for him and paid on his behalf. "Up in the chair, mister," the short Asian attendant snapped, "take off shoes and socks." Rick removed his shoes, and the lady got to work buffing his feet and trimming his toenails. "reservation say toes bright pink, that ok?" Rick nodded sheepishly as the lady started to work. He walked out of the salon later with a bag containing a manicure kit, and bottles of pink and clear nail polish for touch-ups. Week 5. Rick deeply exhaled after finishing his 4 mile run. He sat on the grass in the early Monday morning light stretching in his yoga pants and pink t-shirt. He was glad the App made him do this in the morning, so less people would see him. He had thrown out his old running shoes and replaced them with super cute pink trainers. He stretched his aching legs, and went though a stretch and ab exercise routine step by step as dictated to him by the SissyApp. He jogged back to his apartment after stretching, and turned on the E! Network while stripping our of his damp tight clothes before his shower. He went though his daily shower and shaving routing, when a thought popped into his head. He should stick a finger in his ass. Not sure where that thought came from, Rick continued to wash. No one would know. He should try it. Rick waived a bit, and eventually slid a slick digit in, and back out again. He quickly washed off and finished up, unsure of the origin of that particular urge. As he got dressed for work, his phone buzzed. "Sissy Task: Lock yourself in chastity for 5 days. Freeze your key in 8 cups of water. Submit a photo of the locked device with the numbered lock visible, and a photo of the key in the required amount of water in your freezer. This task expires in 15 minutes." Holy crap, Rick thought, that was the longest time locked up yet. Why was he even still doing this? He looked at himself in the mirror- smooth and in panties- and almost without thinking clicked the device into place. I must obey Mistress. As the thought popped into his head, he snapped the required pictures, froze the key, and went to work. On Friday, he awoke to a SissyCalendar alert. It read "Date with Candi- 7PM, Your apartment. Go to the grocery store, buy lettuce, cherry tomatoes, avocado, and a raspberry vinaigrette dressing. Remember to dress appropriately." Rick was excited and concerned. He was actually looking forward to speaking with the mysterious Candi again- they had hit it off last time but were constrained by the App's geolocation data-driven supervision. At the same time, he was incredibly horny and frustrated after a week in the chastity device, checking his SissyStats to see he could unlock the device at 10PM that night. He was unsure what Mistress would require or what the App would eventually make him do. The work day dragged on for Rick as he anxiously eyed the clock. Later in his apartment, Rick showered and changed, putting on fresh pair of pink panties, a pink striped bra, and a polo shirt and jeans. His phone buzzed "Sissy Tip: Remember how to properly greet a sissy girlfriend!" Rick checked idly Candi's SissyStats card on the SissyCalendar page and "Candi. Height (5'5'') Weight (140) last orgasm (W