Sissy School Art

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Ellis Fairchilde had just been elected school sissy by staff and pupils at Presswell High. There were three votes for Peter Whitless and one for Brad Chambers, but that left four hundred and twenty-six in favour of the quiet, fragile and undeniably effeminate Ellis. 
His mother was delighted at the news. It elevated her in one stroke to a new prominence at the High School and in the social life of the neighbourhood, since Ellis would be in great demand at dozens of events around town. As for Ellis, he collapsed in class when the news was brought, and had to be carried by two grinning guys to Miss Ratchett's office, where smelling salts brought him round to the reality of his new life. 
On Sunday night, the uniform package was delivered by Miss Archworthy, the chief secretary of the school. Before she had got as far as the living room, Ellis burst into tears, and was sent to his room while his mother shared a few words with the secretary about her son's induction at the following day's college assembly. "Here is your invite," declared the po-faced spinster. "The ceremony will be attended by the Lord Mayor and Lady Mayoress, as well as invited guests and parents." She didn't say so, but she could have added: 'all eager to see the early moments of the new sissy's experience.' "Don't worry, Mrs Fairchilde," Miss Archworthy continued, "there will be nurses present to bring him round if he collapses. Everything will be done to ensure that he will fulfil all his duties of undressing and exposure." The visitor gave the boy's mother a sheaf of dressing instructions, and explained the intricacies of the boy's uniform and the importance of wearing it correctly for maximum public effect. Ellis was brought down to listen to the school secretary before she left. 
"I hope you are aware of how lovely you are to look, boy" she said. "Everyone expects you to look very girlish in your uniform, and above all, you must be very effeminate . Is that clear?" 
Ellis's tears overcame him again. "Say 'Yes, Miss Archworthy,' " insisted his mother, and the boy gurgled as best he could as his head nodded. Then, when the visitor had gone, the wailing boy was taken straight up to his bedroom, where the pink dust covers containing his new uniform hung along the front of his closet and over his chair. In one minute, he was standing naked in front of his mother, the cool air caressing his soft flesh and smooth skin. He was a boy with no body hair except a whisp above his little penis, and his mother kept that smoothly razored every evening while she was bathing him. 
"We have to start with girls deodorant," said his mother, shaking the canister as she read the leaflet. The fragrance filled the room as she rolled Princess Pru wetly all over his body and worked it into his skin. "Then we start with the pretty garter belt and nylon stockings." 
"Mummy, I don't want to be th-th-the thchool thithy," Ellis lisped, his voice breaking into another wail. 
"Nonsense dear. Hold your foot still for your nylon stocking." The fully fashioned stockings slid with liquid grace up his legs and were soon attached to his lace trimmed garters. "Hmm, what are these two shorter garters ending in ribbons, for?" She consulted the guide. "Ah, how sweet, they hold your little penis up high. It says your penis must be stiffened and standing straight up all day while you are wearing your sissy uniform." She put down the leaflet and held Ellis's penis in both hands. "Mummy will help her little boy's pencil to stand up for its pretty ribbons, darling." 
Her fingers were soft and effective, slipping up and down the length of his member, while his warbling softened into a helpless kind of murmuring and then into a breathless silence. 
"There, darling, he's standing up nicely. It isn't difficult being a sissy is it." She wrapped the pink ribbons under the knob of his penis and did them into a bow which kept it tensed and standing to attention. "Next we have your sissy breasts and brassiere, darling, all in one. Arms in here for me." 
Ellis wilted with a moan of emotion as the big brassiere cups approached his chest and settled into position like two big mounds of satin covered flesh. His mother spent so long fastening him into it between his shoulder blades that he could tell it was on him to stay. It was terrifying. They made him feel so feminine. His penis stiffened a little bit higher in its ribbons as he gazed down at his bust through his tears, but his shame doubled in agony as he heard the sizzle of the silky net petticoat he had to wear. 
"Arms up, darling... higher, right above your head. That's right," and the frothy tiers of silk and nylon spread horrifyingly around his head and dropped onto his bust, so that his mother had to slide and slither them to and fro to bring the shoulder ribbons down and the full width of his petticoat frills down to his waist. Ohhh, it was so wi-i-ide... and so hi-i-igh! He was petticoated like a little girl. The next thing was a cream silk blouse on a hanger, and Ellis watched his mother undoing the buttons down the front. 
"Aren't you lucky, darling. Look at the lovely blouse you'll be wearing at school tomorrow," as his arms slid humiliatingly through the big puffed sleeves. 
"Mummy, pleathe don't make me wear the thithy blouthe," he cried, his voice descending again into a wail. His penis was rigidly stiff in front of him and he felt utterly defeated as his mother fastened his blouse buttons down the front. "And look, darling. The blouse has a beautiful girly silk scarf, to fasten under here like this," and she checked the diagram on her instructions. "Oh look, sweetheart, it gathers under the silk like this and holds your blouse collar up all round your pretty face. Isn't that sweet?" 
The tears burst from Ellis's eyes and ran down his cheeks inside his silk collar, especially since his mother couldn't wait to put his skirt on for him to see what he would look like in his full uniform. He lifted his arms into the pink satin lining and it hissed down his blouse and onto his petticoat, where the pink pleats opened out wide so that the skirt lay softly over his petticoat, leaving just a few inches of white silk frills still visible all round. 
"Oh how clever, darling," sang his mother. "Your sissy school skirt buttons onto your blouse... here at the front, and here at the back. Now Ellis dear, there's no need to cry quite so loudly. Let me get you fully buttoned up, and then we can see how you look in the mirror." 
But Ellis was in no condition to wait a moment longer. It was the wideness of his pretty skirt, and the way it buttoned onto his sissy blouse that was too much for him, and his ribboned penis jerked up, reaching for his satin skirt lining, through his petticoat frills, and started to jism its helplessness in squirts of cream again and again, which only proved that everyone was right to vote for effeminate Ellis to be dressed in such a sweet and girlish school sissy uniform.




This was originally posted by Feminization-stories, who has since deactivated their account. They gave permission for people to reupload their stories. I was a bit upset. I leaned up against the counter of the "diner" we had set up in the lower school cafeteria. Every year, high school students put on a "sock hop" for the fourth graders. We would set up the gym and cafeteria with 50s decorations, played old music, and let the kids dance and have fun. The cafeteria had been turned into a diner where girls would serve the kids milkshakes and hamburgers, while the gym had a dance floor and some carnival games the kids could play. We also would set up a stage for some of the more musically-inclined high schoolers to play 50s tunes for the little kids to enjoy. Last year, Alan Klein and his band played a great collection of Elvis songs and totally killed it. There was also karaoke on the stage, where the fourth graders could try their hands at singing some 50s' classics for a chance to
Hi! My name is Felicia, and let me tell you about my brother Sam's bet. This story happened two years ago when I was 17. I had waist long light brown hair, green eyes and an average looking body. My 15-year-old brother was the same height as me with brown eyes and short dark brown hair. 
I had my 4 closest friends around for a slumber party, Becky, Mary, Alison and Laura. It was around midnight and we were watching a film that Laura had brought. We were just chatting about how boring the movie was before we heard a discreet thump at the door. Quickly, Mary jumped up and opened it in an instant, causing Sam on the other side to lose his balan
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This was originally posted by Feminization-stories, who has since deactivated their account. They gave permission for people to reupload their stories.
I had just hit the best homerun of my life. I tore through the bases, not watching the ball as it soared above the head of the outfielder. As I reached third base, the pitcher had gotten the ball. I could risk it all, or play it safe. I decided to go for it. As I sprinted toward home plate, the pitcher threw the ball to the catcher with incredible accuracy. I slid onto the base, just before the ball found its home in the catcher's mitt. The crowd roared. I had won the tournament for the team. I, Wade Peters, was a hero.
The horrible ringing of the alarm clock woke me from my slumber. My eyes opened to stare into the soft pink ceiling.
The dream ended, and the nightmare begun.
I rolled out of my large pink bed, throwing the stuffed animals I slept with aside as I walked over to the pink dresser in the corner of my room. I opened the top drawer to peruse my collection of panties selecting a ruffled white pair. Next, I pulled a pair of white stockings up my legs, feeling the smooth caress of the silk against my hairless legs. Then, I went into the bathroom to begin my vanity routine. After I had brushed my teeth, I applied multiple skin-softening oils and creams to my face and rubbed my armpits with women's deodorant. Now I was ready to get started on my makeup. I broke out the makeup kit from the closet behind me and got to work. When I was done, I inspected myself in the mirror. My eyelashes were long and curled, giving a nice feminine look to my brown eyes. My lips were coated in a thick helping of red lipstick. Blush sat lightly on my cheeks, and all of the rough edges of my face had been softened by an extensive use of foundation and bronzer.
I turned my attention to my long black hair, trying to get it into the perfect high feminine ponytail. I patted my ponytail multiple times, checking to see if it had the appropriate girlish bounce and volume. Satisfied, I stepped into the large walk-in closet to get my school uniform. Inside the closet were a plethora of girly dresses and skirts. I selected a blue skirt and a white blouse with long, flowing sleeves and frilled shoulders. I pulled the skirt up around my waist and buttoned up my blouse as I went to grab my next article of clothing. A pink jumper with a male symbol on the back went over the blouse, serving as a stinging reminder to my male status. I grabbed a pink ribbon from the shelf and tied it in a big floppy bow around my neck. I looked at myself in the mirror and primped my outfit to perfection. I slid on a pair of black maryjanes as I took in my helplessly feminine room. The walls and ceiling were all painted in a feminine soft pink. In one corner, a full bed with a pink bedspread was placed. On the bed were multiple fluffy pillows and stuffed animals to reinforce my new prissy status. A fluffy pink carpet rested on the floor, and the large pink dresser against the wall stood as a reminder of my constant femininity. The large mirror on the wall housed a hidden camera that recorded my every action, forcing me to complete my feminine routine every morning or face punishment.
I should probably explain my situation. For the past month, I've been attending the Academy for Petulant Males, or the APM. The APM's existence is completely secret, but it shares a building with a prestigious fashion school, the Alhama School of Fashion and Design, an extremely selective all-girls boarding school. The schools are located on a relatively unknown island off the west coast of America. At the APM, the boys are fully immersed in a sissified lifestyle. They suffer constant punishment and humiliation from both the adults at the school and the female students they share the building with, who are actively encouraged to bully, haze, and torture their male counterparts as much as they like. When I arrived at the APM, I had been sent there by my mother after I was caught smoking with my friends outside of the baseball diamond. She thought that sending me to a correctional school would be the best choice to turn me into a functioning member of society. When I arrived at the school, I was surprised at how grand it looked. The twenty-three boys were taken into a large room, where we were instructed to strip off all of our clothes. This was when I knew something wasn't right here. We then walked through a door and into an auditorium full of jeering girls, and were forced to march down the row and receive an item from Ms. Tracey, the school's headmistress. That item was a pair of panties, which we were forced to put on and stand in front of the girls as they hurled insults at us.
Later, we were taken to the school beautician, Mrs. Stork. Mrs. Stork and her team of skilled salon assistants gave every boy a makeover, involving a new feminine hairdo and full makeup, along with the complete removal of all body hair. Us boys were mortified as we were forced to change into our new school uniform. The facilities at the APM are ridiculously nice. A massive costuming warehouse is available, with many custom sissy outfits coming straight from the shadowy S.I.S.S. Institute, ready to force their ridiculous frills and ruffles onto an unsuspecting boy. Normally, the boys' school uniform is as I described as I prepared myself for the morning, but some weeks Ms. Tracey will announce a costumed theme for the week, with each costume bringing new rules and conditions for us to follow. Stepford week put us all in housewife dresses, fluffy petticoats, and pearl necklaces, addressing each woman we met as 'ma'am' and cooking and serving meals to the girls during mealtimes. Baby week was awful nonstop humiliation, the boys being taunted by the girls as they struggled to waddle down the hall while wearing multiple diapers. During every sissy's weekly disciplinary report, Ms. Sharp, the head of discipline, can decide to modify your outfit for additional humiliation if you've been acting up. Additionally, any girl can request to "Sponsor" a sissy and choose his outfit for a week. If you think we would get used to the humiliation, we don't. The constant changing into new humiliating outfits keeps us from becoming used to one. The school gives weekly tours to visitor groups who walk the halls and laugh at the sissy boys, keeping our shame fresh as our egos are being damaged by the gazes of new tormentors every time.
The school functions on a rigid mark system for discipline. A sissy gets a mark for being out of line or breaking etiquette in any way. This could mean not chewing their food 21 times before swallowing, failing to apply proper makeup and beauty treatments, failing to curtsey before a superior, forgetting elements of their outfit for the week, and so on. At the end of the week, each sissy goes to Ms. Sharp for a disciplinary evaluation. Ms. Sharp reviews both the camera footage of the sissy that week and written "marks" that could be submitted by girls or teachers any time. Very few, and the boy will be allowed to have a "boy day" that week, meaning they can wear male clothing provided to them by the school for that week. Many, and the boy will be put into a special outfit that week, selected by Ms. Sharp to be the most painful and deliciously embarrassing for the boy in question. We will also be given seasonal outfits on certain days. During warm summer days, the boys have the option of dressing like spoiled teen sluts in crop tops and yoga pants. During the winter, I was put in a fur pom-pom shaped hat, mittens, a scarf, and a fur-fringed dress with a multitude of petticoats by a group of girls who demanded I bundle up for the winter. The girls at the school attend normal high school classes; Algebra, English, Art, along with classes about fashion. The sissies, on the other hand, took classes like "Being ladylike 1", "Ballroom Dancing", "History of Damsels in Distress", and so on. I was forced onto the cheerleading team by Ms. Tracey, where we don ridiculously skimpy outfits and perform incredibly humiliating dances with pink pom-poms in our hands. It was hell, and the administration at the APM made sure we always remembered our place as males. They didn't want to turn us into girls, just the most feminine, humiliated boys we could be.
I walked down the pink hallway. I moved with a measured gait, placing one foot in front of the other and swaying my hips to be in perfect feminine form. As I walked into the building's extensive cafeteria, I saw many girls and sissies rushing to breakfast. I stepped into the cafeteria to see that a banquet was laid out before me. Eggs, bacon, sausage, toast, stacks of pancakes, all sat on large platters, their delicious aromas wafting through my nostrils, sending me into ecstasy. it was glorious. My mouth started to water as I stared at the massive table with its assortment of delicious food atop it. A voice broke my trance.
"What are you looking at, pansy boy?" A girl sitting at the table said smugly to me. My hands grabbed my skirt and my knee bobbed in a quick curtsey before I walked over to the smaller pink tables in the corner of the room. I sat down on the pink stools, making sure to smooth my skirts and straighten my posture, and looked at what was on the table. A feast of white rice, carrots, celery, cherries, chickpeas, pomegranates and alfalfa stared coldly back at me. The boys at APM were deprived of all meat, only allowed to eat foods, mostly vegetables, with high estrogen content. It was tantalizing to see the girls munching away at their protein-packed breakfast while I shoveled another spoonful of cold rice into my mouth. A hand slammed my back and I recoiled, letting loose a girlish shriek as my plate clattered to the floor.
"Sissy!" Shouted the voice of Ally Bachman. Ally was a girl I had known in middle school who just happened to attend the same academy I now occupied. I remained silent, making sure to chew my food the required 21 times before swallowing.
"Oh Wanda!" Ally yelled again. "We have to have a little chat!" I remained still, taking a slow sip
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