Sissy 101: Intro To Sissy Sluts free porn video

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Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description catalog. I did a search for the classes by name and they did show up, but I was unable to access the course descriptions without a password. My curiosity piqued, I entered my email address and clicked on the "Forgot my password" link. A web confirmation popped up saying that my password information had been sent to the primary account holder at RobertCEO@Robert DavisIndustries. Now I was really confused. Robert the CEO at Robert Davis Industries is my father. As if reading my mind, a text message suddenly appeared on my phone screen. It was from Miss Godhead, my father's long-time personal assistant. "Michael," it read, "Your father would like to meet with you today at 4:15pm to discuss your university schedule. Do not be late." As was usually the case with anything to do with my father, it was assumed that I would obey any command without question. A calendar event was automatically added to my schedule. I mindlessly clicked on the accept button for the mysterious meeting listed as SISGEN101/SISHYP/161. I arrived at my father's downtown office almost a full hour early. I signed in and Miss Godhead came down to the lobby to escort me upstairs. "Michael, let's get a look at you," she exclaimed with a big smile as she crossed the lobby and gave me a big hug, grinding her breasts into me as we hugged. "The last time I saw you, you were just a boy." She glanced down at my crotch and I realized that I was rock hard. She smiled. "Apparently you're all grown up now." She led me toward the elevators without any further comment. I followed her like a dog in heat. You have to understand that Miss Godhead (or Miss Good Head as I prefer to call her during the many times I've masturbated with her in my mind) has the body of a porn star and simply exudes raw sex appeal with her every movement. I have never met a sexier woman than my father's personal assistant. For one thing, she's taller than me, even without her ever-present stiletto heels. Put them together and she towers over me and is so imposing that I would never even consider not doing anything she asks of me. I'm sure I'm not alone in this, and I'm guessing that it's a big part of why she's been so successful as my father's personal assistant all these years. If her height isn't enough, Miss Good Head could also be called Miss Big Boobs. I don't know her cup size, but it's up there. It's impossible not to get lost in her deep cleavage. She knows this and always wears lacy bras and low cut blouses that make her into a wet dream come true for any man who happens to be attracted to big boobs--in other words, just about every man in the world loves to leer at Miss Godhead, not just this horny 19 year old. She has a porn star body and wears clothes to match. I've always considered her face to be that of a sexy librarian who is just waiting to rip off her glasses and let down her hair in some horny schoolboy's fantasy. Needless to say, I had been fantasizing about my father's personal assistant ever since I was old enough to get an erection. Miss Godhead smiled as if she was reading my mind. She held the door to the corporate elevator for me. I kept my hands covering my crotch as the elevator doors closed and we started to ascend. "You know, Michael," she said without even turning to look at me, "there's no reason to be embarrassed. I am aware of how men look at me. I consider it to be a compliment." She turned toward me and I realized that she had unbuttoned her blouse. "You've always had a thing for me, yes?" she asked as she hit the elevator stop key and input a numerical code that turned off the automatic emergency alarm. She didn't wait for a reply, but sank to her knees and began to unbuckle my pants. "Like I said, I take it as a compliment." She fished my cock out of my pants. It was already twitching and threatening to explode. She looked up into my eyes and smiled before turning her attention to my manhood. "All grown up," she said as her tongue snaked over the head of my cock. She devoured me whole. My cock disappeared completely down her throat and I immediately started to buck as her tongue glided up and down my shaft. One hand began kneading my balls while the other snaked its way to my ass. I felt her manicured nails scraping at my rosebud for just a second before plunging into my nether passage. That was all it took. I exploded down her throat before she could send a second finger up my ass. Miss Good Head more than lived up to her fantasy name and kept her mouth tightly locked around my cock until she coaxed out my last few drops of cum. She looked up at me and opened her mouth to show me that it was filled with my deposit. She smiled, closed her mouth, and swallowed it all down. She licked her lips. It was the sexiest thing I have ever witnessed. She stood and buttoned up her blouse as if nothing unusual had happened. "Consider that to be my graduation present," she said. "Do well in your studies, young man, and I might just willing to give you more presents in the future." The elevator started moving before I could respond. God knows that I couldn't think of anything to say--this was my adolescent fantasy come true and I was stuck, overwhelmed by what had just happened. In fact, it was almost a problem as Miss Godhead gave a quick look down at my groin to remind me that my pants were still pooled around my ankles. The elevator chimed its arrival and I scrambled to pull up my pants and look presentable before embarrassing myself in front of my father's staff. The doors opened to the top floor and I was greeted by another wet dream come to life. God knows that my father knows how to pick his staff--almost all of them are extremely hot young women who dress like strippers rather than what you would expect from a Fortune 500 company. Miss Godhead passed me off to a secretary named Kumiko and told me to wait in the reception area until my father was ready for me. A Japanese schoolgirl fantasy come to life approached and led me to the waiting area. She asked if I wanted a something to drink, and then blushed as she added, "perhaps a sports drink to replace your fluids, Sir" I was confused until I realized that there was an elevator security monitor feed directly above her desk. My heart sank as I realized that my father's entire support staff had probably just watched me get a blowjob from Miss Godhead on the elevator ride up. Now it was my turn to blush. I stammered, looking for an explanation, but Kumiko brushed it all aside. "Don't worry, young Master. We see far more than that all the time." She stifled a tiny giggle before adding, "I usually have the honor of escorting our guests up to this floor." The word "escorting" dripped with innuendo. Kumiko went and sat at her desk with her head bowed. It was a bit strange, as she spread out her skirt and carefully lowered herself onto her perch. Her breath caught in her throat as she sat. She kept peeking up at me as she nibbled on her pen. I couldn't take my eyes off of her, and she seemed to know it. Was she bobbing up and down in her seat? It almost looked as if she was having sex with some unseen lover hiding underneath her desk. Of course, that was crazy, especially in a respected business office like this. But then again, why was she breathing so strangely? Why was she absentmindedly rubbing her nipples? And what was up with the soft moans that I would occasionally hear coming from her direction. I didn't even try to hide my curiosity. I stood up and went to the reception desk. Kumiko lifted the back of her skirt and showed me that she was impaled on a dildo that was as thick as my wrist. The pole was bolted securely to her chair and disappeared deep into her very- stretched out ass, which allowed Kumiko to slowly bounce up and down as I watched. The phone rang and Kumiko answered, speaking in what I assume was Japanese. She didn't stop riding her dildo during the phone call. My mind was racing and I began to wonder if she spent her entire day mounted on this penis. I was obviously rubbing myself by this time, despite the fact that I had just cum ten minutes earlier. Kumiko noticed my erection, and giggled seductively as she began to bounce up and down more vigorously for my pleasure. It was only when she began to moan in ecstasy at the top of her lungs that I realized that we were in public. Embarrassed and worried that my father would find out, I left her and went to sit back down. Kumiko pouted when I stepped away and stopped fucking herself on the chair. She had the cutest little frown. After a moment's hesitation, she removed something from her drawer that was wrapped in an ornately embroidered silk handkerchief. She stood up (there was an audible pop as she rose) and she stepped over to close the reception area door before kneeling down at my feet, bowing her head and offering the wrapped- wrapped package to me. "If I may be so bold, Sir," she said as I unwrapped the package, "I think you might enjoy these." They were a series of metal balls connected by a steel cable. Kumiko could see the confusion on my face, so she explained that they were "Anal beads, Sir. Some gentlemen prefer to keep these lodged in their rear passage during the day. It keeps them on edge and ready for whatever is to come." I still wasn't sure what was going on, but Kumiko stood and helped me to my feet. She led me over to her desk and then stepped around behind me and undid my pants. Then with surprising authority, she bent me across the desk. I could see the dildo mounted to her desk chair. It was huge! I wondered how such a small woman could manage to fit such a monster cock inside of her? Kumiko lowered my pants and underwear. She licked her fingers so that they were good and wet, then she slowly slid three digits into my ass and began stretching me out until I was loose enough for the metal balls to enter. I closed my eyes as I enjoyed the strange sensations playing out in my rear passage. It felt like heaven and I began to fantasize about what it would feel like to ride Kumiko's giant work dildo. My eyes rolled back up into my head as Kumiko pulled out her fingers and began working her tongue past my wide-open sphincter. I almost came as the anal balls were slowly-but-insistently forced up inside me. I've never felt fuller, or hornier in my life. I began to stroke my cock and was just about to shoot my load across the reception desk when the door flew open and Miss Godhead strode into the room. She grabbed Kumiko by the hair and threw her to the floor. Kumiko whimpered in fear as Miss Godhead glared at me and took a wooden paddle from a desk drawer. Kumiko submissively stood and stepped past me as she bent over her desk. She raised her skirt to reveal her glorious bottom, and her tiny baby cock wrapped up tightly in a metal cage of some sorts. I stared in disbelief. I heard the paddle whoosh down as Miss Godhead tore into Kumiko's exposed flesh with a mighty blow. I was about to start masturbating at the sight, but I suddenly realized the door was open and the rest of the office staff had gathered around to watch Kumiko being punished. I stared in a mixture of disbelief and lust as the scene unfolded in front of me. Miss Godhead didn't let my latest fantasy play out. "Take those filthy thing out of your ass before your father finds out," she demanded. Before I could react, one of the secretaries came forward and pulled the balls out before helping me get back into my clothes. With a jerk of her head Miss Godhead motioned the secretary to take me into my father's office. She stopped me just before I left the room. "There are two types of people in this world, Michael," she spat out in between blows down on Kumiko's now bright-red ass. "Those who are Masters and those who serve the Masters." She wheeled towards me. "If you choose to act like a servant, a slut like sissy Kumiko here, you'll be treated as such." Dragging Kumiko by the balls, she threw her to the ground. Kumiko screamed in agony. Two secretaries were right there with rolls of some sort of heavy tape. They lifted Kumiko to her feet and began to encase her in a solid mummification wrap. Kumiko had her head bowed as she tried to stop her tears. Within moments she had been totally encased in the tape. She was cocooned from head to toe save for her nostrils, and unable to move even a finger. Miss Godhead strode toward me and pushed me out the room. "Don't forget what you saw here today. You're the Master's son. Act like your Father, not some dumb sissy slut!" With that she closed the door, leaving Kumiko's fate to my imagination. One of the secretaries had followed me out of the room. She helped me get my clothing back into a presentable state. "Don't worry, Sir," she said as she dropped to her knees and began buckling up my pants. "Your father has big plans for you," she smiled up at me and added, "Follow his lead and you'll have plenty of time to play with your own stable of sluts like Kumiko." "Well, not Kumiko," she added after a moment's hesitation. "That whore will be in some seedy brothel by tonight, but some other sissy slut more appropriate to your standing for sure." She leaned forward and placed a long kiss on my crotch. Then, rising without another word of explanation she led me into my father's office. Dad was on the phone, but he motioned me to sit while he finished up his call. It was the first opportunity that I'd had to stop and think since I had arrived. Okay, I asked myself, what the fuck was going on? I've always known that my father was a very wealthy and respected CEO. I've always suspected that he had a thing going with some women on the side. Heck, mother even seemed to know this and was okay with everything. But an entire office staffed with sexy secretaries? Some of them sissies? It was almost unbelievable, although my cock did jump at the fantasy vision of Miss Godhead parading around like some corporate madam overseeing an office full of willing whores. It dawned on me that my father has offices in London, Geneva, Tokyo and Dubai. Does he keep offices staffed full of sluts all over the world? Needless to say, I was suddenly, and for the first time, very interested in knowing more about what my father did for a living. The door opened and Miss Godhead came in. Her head was bowed. It dawned on me that she was just another slut for my father to use as well. Talk about a radical re-working of my adolescent fantasies! Once again, I noticed that my cock was tenting my pants. I glanced over at Miss Godhead for relief, but she kept her head bowed. "For God's sake, Michael," my father suddenly said, "Get a hold of yourself." I jumped and quickly adjusted myself so that my erection wasn't quite so noticeable. Father sat in the chair across from me. He looked me straight in the eyes and took a moment to collect his thoughts before beginning. "Michael," he said, "I'm a very successful man. And before you start your university education, I'd like to share one of the secrets to my success." He snapped his fingers and Miss Godhead stepped over and immediately began disrobing. I couldn't take my eyes off of her amazing body. Her massive breasts burst free of her bra, and I wondered if having to haul around so much weight everyday would be painful. I wondered what it might be like to have my own set of big titties. I smiled at the thought. My father pulled me back in to the matter at hand. "Most people never see past this slut's breasts, so they don't appreciate her real secret." Miss Godhead shimmied out of her skirt, revealing her own cock locked up in a metal cage and tucked away behind some frilly pink panties. Miss Godhead was a guy! Despite the cage, I could tell that he was a guy with a very big cock to boot. Of course it's hard to call it a cock when it's stuffed in a pair of panties. My father gave me a moment to take it all in before continuing. "I met Stephen here in college. He was a skinny kid who was my math tutor, but I knew right away that he would do much better in this world if he were to become a she." He looked up at Miss Godhead and smirked as she was standing there with her head bowed, trying in vain to control her breathing. "Isn't that right, Stevie?" he asked and Miss Godhead immediately responded, "Yes, Master. I am forever in your debt for making me into your big-titted sissy cum dump." "And how do you prove your gratitude?" he asked. Once again, the reply came immediately. "I will do anything and everything Master demands of me, without question or hesitation." "And she has," my father said while turning back to me. Without breaking eye contact, he snapped his fingers and said "Urinal." Miss Godhead dropped to her knees and lovingly fished my father's cock out of his pants. She opened her mouth wide and my father began to fill it full of his piss. Miss Godhead didn't spill a drop as she swallowed it all down as if she were put on this earth to be my father's private toilet. When he was finished, Miss Godhead leaned forward and licked him clean before zipping up his pants and moving off until she was next required. There was a sadistic grin plastered across my father's face as he turned back to me. "The history of this world is dominated by men who are served by devoted servants. The days of slavery are over, but it's still possible to find servants who will willingly devote themselves and help you forge your path in life." "It's time to discuss your university education," he said, "and to let you in on some family secrets." He reached over and pushed a button on his desk. The doors opened and the entire office staff walked in. All fourteen secretaries were completely naked. All of them were goddesses in physical form. All of them also had tiny proof that they had started out as boys before they were caged and transformed into my father's sissy staff. "I keep several dozen sissies here in the city, and another sixty or so in my foreign offices." I was flabbergasted and unable to respond. "They are all well cared for, happy and devoted to me." Isn't that right, my beautiful sissy sluts?" In unison, all of the office staff responded with a memorized response, "Yes, Master. Thank you for rescuing us from our old lives and turning us into your personal sissy sluts. We are yours to command." "See," said, "I'm a hero. They love me and are devoted to me because I saved them all from their wasted lives as pathetic men." The staff nodded its head in collective agreement. My father dismissed them all with a wave of his hands. He said, "Playtime for the next thirty minutes," and the entire staff popped up and began to giggle and chatter like excited schoolgirls. "But," he stopped them as they were leaving the office, "have fun, but I'm setting the alarm to level six." Their eyes widened with fear as they left the room. They didn't close the office doors, so I watched as the entire staff pulled dildos and other toys from their desks before dropping to the floor in a full- fledged sissy orgy. It was impossible to concentrate on what my father was saying, knowing what was happening just a few feet outside the door. He led me back to my chair and continued. "So, you see I've taken the liberty of signing you up for some exclusive courses--I think you'll find these to be more interesting than biology or psychology." I nodded my head dumbly. "I've joined with a few other, select partners to provide a proper education for promising young men who will go far with the help of a sissy support staff," father smiled down at me. "We will introduce you to your first sissy and teach you how to train her to your specific needs." "I don't know what you kids are into these days, and I don't really care," he continued, "but with a well trained sissy, you can do anything you want." Father leaned forward and whispered conspiratorially, "I have a colleague in Dubai who is experimenting with extreme medical surgeries and hormone treatments for his sluts. He is literally turning his entire collection into a heard of lactating cows." My eyes must have popped open in horror because father laughed at my reaction. "Tell you what," he said, " let's just get you set up with a sissy to blow you at night and we'll take it from there." I nodded in relief. "So you're signed up for General Sissy Studies and also a course in Sissy Hypnosis." I looked puzzled, so he explained the advantage of having a sissy who has been hypnotized to always do your bidding. "You can make her do anything, no matter how disturbing," he chuckled as he stood and called one of his sluts back into the office. He walked over and whispered something into the sissy's ear and she was suddenly overcome with a physical reaction. Her stance changed. Her voice lowered and she began to cry. "Michael," my father said, "meet sissy slut richard, one of the best cocksuckers I have ever used." Why? Why are you doing this to me?" sissy richard choked out in between sobs. Miss Godhead strode forward and slapped her full across the face. The sissy collapsed to the ground with a look of anguish on her face. "I never wanted this!" she cried out. Father wasn't moved at all. "And occasionally," he said, "sissy hypnosis is very useful if you need to remove a rival." The sissy wailed. "It was just a business deal!" Father spat back at him, "And now you know to never, ever cross me, even for a tiny deal! Isn't that right, sissy richard?" Sissy richard nodded her head in assent. Father took a moment to calm down before continuing. "richard," he said while raising the sissy to his feet. "You have served me for 17 years now, but it's time for you to go." Sissy richard immediately began to protest. "Where will I go, Sir? Please, let me stay." My father snapped his fingers and the sissy was immediately silent, although trembling. "No, the decision has been made, although the final outcome is still in play." An evil grin played across my father's face. "You get to choose. I can box you up and send you to a friend in Bulgaria who needs somebody to take care of his animals. And I mean take care of all of his animals' needs, which means that you will become a breeding bitch on his farm." "Or, I could hypnotize you into becoming one of farm animals. How would you like to spend the rest of your days as a pony girl, pulling you new master around in a cart, plowing his fields, maybe even racing for him." "Of course," he added, "I'm guessing that you'd end up being a mare for some of his real horses. I can't imagine that you'd last very long like that." Tears were streaming down sissy richard's face. My father pulled a handkerchief from his suit pocket and offered it to the sissy. "Or, I can put you back into hypnosis and send you back into the world as just another sissy slut. With your surgeries, you easily pass and could certainly get a job as a bar tender or a waitress. Perhaps a street whore. Maybe even get married one day." The grin re-appeared again, "I could put you back under so that you spend your days thinking that you have always been a sissy, although I will probably leave you with a hypnotic suggestion or two that will make you always horny, and uncontrollably sexually attracted to, let's say, homeless bums." He laughed, "Like drop to you knees in the middle of the street to blow any bum you see." If that troubled sissy richard, it didn't show at all. "Yes, Sir. Thank you, Sir," she said. Please do anything you want to me, just let me go back to being my true sissy self, and please, Sir, don't send me to the animal farm." "Are you certain, Richard?" my father needled. "I could make you like being used as a farm bitch?" "Please, Sir. No. Make me a bum loving slut instead." There was a long pause before the sissy continued. "I am sorry for ever having troubled you, Master," she said. "I will do whatever you demand. Send me to the farm, or wherever you wish. I am a dumb sissy cum dump who deserves whatever you choose for me." A look of triumph flashed across my father's face. "I will show you mercy, but you have to prove that you really want me to do this to you." sissy richard bowed his head and said, "Yes, Sir. Anything you want." Father walked around his desk and pulled out a knife. He handed it to the sissy. "Slut," my father said, "go to the ladies room and chop off your sissy clitty and stones. Take Miss Godhead with you to help." sissy richard stared at the knife in horror. "Cut off my balls," she said. "And your penis," my father corrected. "The whole thing," the sissy squeaked, "then you'll return my hypnotism programming and let me live out the rest of my days as a mindless sissy bimbo?" sissy richard went white in the face, but then a smile crept across his face. "Yes, Sir," he said, "I'll be a real woman after I get rid of this ugly sissy stick." He bowed and left, holding the knife as if it was a sacred relic. Turning to Miss Godhead, father whispered, "Get Dr. Belcher here first so the dumb slut doesn't kill herself." Miss Godhead asked, "Should I just have the doctor do the castration?" "No," my father replied firmly. I want richard to do it of his own accord, unless he changes his mind and decides to become the farm bitch." Father smiled. "No worries, all of you have a self-preservation hypnotic command." Should a sissy genuinely try to harm herself, she will black out before anything happens." The sadistic look was back on his face. "Wait until the dumb slut goes catatonic, then call Dr. Belcher up to do the job correctly." Miss Godhead bowed and started to leave. Father stopped her with an added thought, "let's make sure that the entire staff is there to witness sissy's castration." Miss Godhead left, and my father excused himself for a moment while he opened an app on his phone. "Can't let them have too much fun," he said and pushed a button on the phone. The office was suddenly filled with screaming sissies. Father laughed in pleasure. "I keep them locked in chastities at all times," he explained, and those chastities are always hooked up to an electrical device which helps to remind them of their proper place in life." He pushed the button again. The whole staff screamed once again. "This is level six," he explained. "The tend to pass out if I turn up the juice much higher." When I still looked confused, father pressed the button once again. Over the top of the screams, he explained that by pressing this button, every one of his sissies would immediately be forced to her knees and wracked with searing pain. "It reminds the sluts that I can put them on their knees at any time I choose. For any reason I choose." Father pushed a button and several TV monitors in his office turned on. There were multiple video feeds from his overseas offices in London, Dubai and so on. Every monitor showed an office full of sexy secretaries rolling on the ground in agony as their groins were filled with electrical pulses coming from my father's phone. These women had no idea why they were being shocked, but they certainly knew that it was all part of being a sissy slut for my father. It was no surprise that I was rock hard once again at the thought that one day I might have a room full of sexy sissies waiting to do my bidding. I very much wanted to learn all of my father's secrets. Dad saw this change come over my face. "Good boy," he said. "I've got a lot to teach you." He led me to the couch and pushed a button next to the armrest. The cushions retracted to reveal two beautiful female faces poking through holes in the seat. They immediately stuck out their tongues and my father instructed me to take off my pants. "Can't tell you how many deals I've closed on this couch," he said. We sat, and the couch sissies immediately began licking our asses, insistently trying to snake their tongues past our sphincters. I was so lost in the sensation that I didn't notice that the other sissies had entered the room. Some came bearing drinks and cigars. Most dropped to their knees and began to lick and kiss us from cock to toe. Father smiled paternally. "Now, let's talk about college..."

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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...

1 year 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...

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...

2 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."...

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...

1 year 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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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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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm 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 Doctor Shirley Williams. 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 Jamie Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen 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...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

2 years ago
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Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) 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...

1 year ago
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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...

2 years ago
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Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

1 year ago
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Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

3 years ago
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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
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Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

3 years ago
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Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
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Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve 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....

4 years ago
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Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

2 years ago
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Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

2 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

1 year ago
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Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

3 years ago
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Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

1 year ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

3 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

3 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - 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; Doctor Shirley Williams: 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...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

2 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - 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...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

1 year ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

1 year ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

2 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

1 year ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - 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 Jamie, ...

1 year ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

3 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

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