Perry was feeling pretty good about himself as he walked home from school. That morning had been the big debate between his Boys School and the nearby Girls School. The topic had been woman’s liberation, and he had done a real job on his opponent. It wasn’t a tough subject for Perry to debate–girls should stay at home and do girl’s stuff and that was all there was to it. For that matter, it wasn’t hard to beat a girl in anything anyway.
He grinned as he thought about some of the lines he had thrown out during the debate. “Girls grow up playing sissy’s games with dolls and pretending to be mommy’s…..and that’s all they’re good for! They play dress up all day long, trying on frilly clothes that are of no use except to make them look like dolls themselves anyway! And if they’re not doing that they want to shop for new clothes all day long! Put a girl in a real job and all they do is worry if their stockings have a run in them, or if their makeup is on straight! All they want to do is practice how to look pretty so they can trap a man someday into supporting them, and they can stay home and play dolls with real kids!” That last line really got to the girls in the audience. Boy did they boo and hiss!
As he rounded the corner and started up his street he suddenly came face to face with his adversary that day. Janet seemed to be upset and spoke first. “Oh Perry, I’m so glad to see you. I’ve locked myself out of my house and can’t get in,” she whimpered girlishly. “Do you think you can help me, please?” To Perry, this was just another example of how stupid girls were. Always getting into trouble and needing a guy to come to the rescue. He played his chivalrous role to the hilt. “Sure, what do you want me to do?”
“There’s a ladder in the garage–you can use it to get into my bedroom window. It’s too heavy for me to lift.” Perry could not help rubbing it in as he hefted the ladder up to her window. “What happened to your woman’s lib, huh? I thought girls could do anything guys could? It’s just like I said this afternoon: `A girl is no match for a guy.’” As he climbed the ladder and reached the slightly opened window Janet smiled wickedly behind his back and replied, “Oh I don’t know about that.” Perry swung his leg through the window and disappeared from view.
Two hours later Perry was standing before a mirror, tears forming in the corners of his fifteen year old eyes. He was dressed like a girl and was surrounded by a giggling Janet and three of her classmates. It had all happened like this: Once in her room he was immediately jumped by Janet’s friends who had been waiting for him. Despite his best efforts he was instantly overcome. As the girls finished tying his arms and legs Janet appeared at the door with a big pair of scissors. “Well, Perry dear, it seems that girls can be a match for boys, don’t you think?” she sneered. “What’s going on here,” Perry shouted. “Let me up now or I’ll . . .” “You’ll what, sweetie?” Catherine laughed. “You think you’re so smart, and boys are so much better than girls. Well we think you’re wrong, and you’re about to find out just how wrong you are. You think you know so much about what it’s like to be a girl? Well, you’re going to find out just what its like to be a little girlie sissy, and there’s nothing your big macho ego can do to stop us!”
Perry started to scream and shout, but his ranting only resulted in a gagging. He was lifted to his feet, while the girls teasingly covered him body with Nair. “We’re going to get rid of all that nasty hair Perry so that you’ll be smooth all over, just like a girl,” Katie giggled. The girls untied his bonds and pushed him into the shower. When he was finished his body was indeed rid of hair, including his crotch. The girls dried him off and liberally dusted his now hairless form with sweet smelling powder. His bonds and gag were now unnecessary. The girls knew they had him, that there was nowhere he could go in his condition and without any male clothes. He knew it too.
Perry allowed the girls to lead him back to Janet’s room. His mind frantically searched for a way out of this embarrassment but he drew a blank. He froze in his tracks when he saw the clothes laid out for him on the bed. Sally picked up a pair of pink rumba panties, dripping with row upon row of lace ruffles and bows. “Would you like to put on your little panties now sweetheart?” she inquired, her voice tinged with sarcasm. “No, please no, don’t make me wear them, don’t . . .” he whined. “Oh yes you will wear them,” Janet added with a wide smile, “Unless you want us to make you walk out through the front door like that,” she threatened. “You think girls are second class citizens. Well its about time you found out what its like to be one. And by the time we’re through with you, you will be one,” she lectured.
The panties were slowly pulled up his legs. “Oh look girls,” Catherine cried. “Perry likes his sissy little panties!” Perry was shamed beyond belief as he stood there before the four laughing girls. A pink vest, matching his panties, was pulled over his head, and as he lowered his arms a bright flash blinded his eyes. Katie smiled broadly from behind her Polaroid camera. She waved the slowly developing print before his face and teased, “Now if you don’t behave like a proper young lady we just may have to show this at school little Petty.” The girls crowded around as the print developed and laughed uproariously at the incriminating photo, with the clearly evident bulge at the front of Perry’s panties. “She looks too cute to be a boy anymore,” said Janet. “Let’s call her something really sweet and feminine. How about Prissy?” Another round of laughter and giggles filled the room as they unanimously agreed that Prissy was a highly appropriate name.
The girls proceeded to dress the trapped boy, giggling and teasing him further with each article of girlish clothing, and taking more pictures along the way. “This is your pretty petticoat Prissy darling. See how stiff the taffeta layers are? They’ll make your darling dress stand up beautifully. And isn’t the lace trim just the sweetest?”, they mocked.
Pink anklets and black Mary Jane’s were placed upon his feet and then the girls readied the dress. “Now Prissy darling, I know you must be very excited about wearing such a lovely little sissy dress as this one. I want you to tell us how much you want to wear it and thank all of us for helping you be such a pretty little girl”, Janet teased.
Perry balked. He hadn’t said a word during the entire ordeal, and couldn’t find it in himself to betray his masculinity. “All right then, I guess you need a further lesson in being a good girl,” Janet responded. The girls marched the sissified boy over to the vanity bench and sat him down. Catherine and Sally each took one of his hands and began filing his nails, and then coated them with bright pink polish. “You see Prissy dear, I wasn’t going to paint your nails, but since you still don’t feel girlish enough you left me no choice,” Janet tittered as the polish dried. “I don’t plan to pierce your ears or give you a perm either, but if you don’t learn your lessons soon I may just have to do that too,” she threatened.
The girls had a hard time keeping quiet during Prissy’s speech, but convulsed with laughter when he finished. Unfortunately for Prissy his performance lacked polish, and he was required to repeat it several more times, until he finally concluded it without the written draft for assistance.
Janet then led Prissy and the others down to the living room. The girls enjoyed themselves immensely, instructing the submissive little girl/boy in proper feminine mannerisms–how to walk with a swish, how to sit gracefully, fluffing out her petticoats, and especially, how to curtsey demurely. The girls even ordered him to lift his skirt and petticoats and place his panties on display before them, revealing for the camera the swelling at the front of his panties, and the dark spot forming near the waistline. Perry did not resist this continuing humiliation, even though more pictures were taken and the girls were nearly dying of laughter–if only in the hope the girls would tire of the game and let him go. Janet had promised he’d be out of the dress in a couple of hours, but time seemed to crawl for him. He was finally ordered to stand before them with his hands clasped demurely in front of his waist. Janet spoke next.
“Prissy darling, it’s now time for you to repent for your inexcusable behavior today at school. A very nasty boy named Perry said a lot of awful things about girls, and we think you’re to blame. But we’re not mean people–we want to give you a second chance. My parents are gone for the weekend and you’re going to learn all about what it’s like to be a girl for us beginning right now, just like you said in your cute little performance in the bedroom. You’re off to a good start, but we’ve just scratched the surface. For the next few days we’re going to bring you through all of the stages of being a girl, and we expect your full cooperation. That means that IN EVERY WAY YOU WILL ACT AS A GIRL. Not as a boy pretending to be a girl, BUT AS A GIRL. We’ll help you out, but if you don’t satisfy us you’ll receive demerits, and you’ll be punished if too many accumulate. Do you understand?”
Perry stood there dumfounded again. “You . . . you mean I have to do this all weekend?” “That’s one demerit,” grinned Katie.
More tears formed on Perry’s face as the enormity of what he faced sank in. “Do you understand?” repeated Janet.
“But, but you said I could have my clothes back in a few hours…….Please, can’t we talk about this, please?” implored Perry, now feeling as if the quicksand he had climbed into through the window was nearing his neck.
“And that’s two demerits,” joined in Catherine. “We warned her.”
“I think we should put her back in diapers,” said Sally. “She’s obviously not as advanced as we had thought.”
“I said you could change out of that dress. I didn’t say you could put your boy’s clothes back on, did I?” sneered Janet. “Now do you understand, or do you continue to accumulate demerits?”
Perry nearly broke out sobbing, but he got the message. “Yes, Janet, I understand,” he whispered.
“Great,” smiled Janet. “Your going to be our little sister Prissy, and act as a six year old girl until we’ve decided that you’ve advanced enough to grow up some. But just in case you have any other ideas, I think you ought to watch some television with us.” Katie turned the TV set on, and slipped a video tape into the VCR. And there, in all his glory, stood Prissy, reciting how much he adored to dress, and act, like a little girl sissy! The girls all erupted in a cacophony of laughter as Prissy stared, dumfounded, into the TV set.
“You…..you…..” he stammered, but couldn’t get out the words. “That’s right, Prissy!” crowed Sally. “You were looking into a two way mirror, and we had a camera on the other side!”
“So you’d better take us seriously”, joined in Catherine. I’m sure you’d just love to have this tape circulate around at school, huh? Can you imagine? Macho man Perry telling all the world how much he adores being a sissy and wearing his frilly pink dress!”
Prissy stood there before the girls, tears again forming in his eyes. Only this time they came down in torrents. He bowed his head and wept. His skirt was so full he couldn’t hold his hands at his side. It seemed automatic to place them neatly at his waist, the white purse over his wrist gently resting on the front of his pink skirt. He was the perfect image of a little girl sissy, and as he realized it, the tears flowed even more heavily.
“You’re not behaving Prissy”, warned Janet. “Bad boys being punished in dresses cry like sissies. But real little girls like wearing such pretty clothes, and acting as if they love every minute of it. Now stop it this instant or you’ll get enough demerits to be punished!”
Her speech merely caused his tears to increase further, and Janet declared that a punishment was indeed in order. Still sobbing, Katie and Catherine grabbed Prissy’s wrists and pulled him down over Janet’s lap. His skirt and petticoat were raised high up his back, revealing the pink rumba panties in all of their glory. Janet slipped the panties down Prissy’s legs, and began to slap his bare bottom, while Katie and Catherine maintained their grip, preventing him from escaping.
“You’d best learn now that your only chance of ever being a boy again is to behave LIKE A GIRL NOW ! After ten slaps Prissy gave up all effort to escape, and passively lay there, receiving his spanking like a submissive little girl, wildly flailing his legs as if to ward off the blows. Janet finally stopped, and, after his panties were restored and his skirt and petticoat lowered, Prissy was released to stand once again before the four triumphant girls.
“Now. Unless you want a repeat of that performance, I suggest you demonstrate to us that you are ready to act as you are dressed!” declared Janet. Prissy paused, shifting his weight from one leg to the other, trying to get some relief for his sore bottom. Finally, in desperation, and not knowing quite what to say, he whispered that he wanted to play with dolls. “I didn’t hear that”, said Sally. “Speak up now Prissy”, she gloated. “Please, may I play with my dollies?” he inquired in a slightly louder voice. “You can do better than that”, encouraged Sally. “Now try again.” Eventually, after asking in a higher pitched, feminine voice for his precious little dollies so that he could play house and pretend to be the mommy, the girls relented.
And with that a group of dolls was produced and Prissy sat on the floor before her older sisters and played house, much to the girls’ fine amusement. Prissy’s efforts were not exactly satisfactory however, and the demerits began to accumulate, most of them attributable to Prissy’s sullen demeanor. “Little girls should be enthusiastic when they play with their pretty dollies, Prissy,” instructed Catherine. “You seem more like a naughty little boy who’s being punished,” she grinned. The tenth demerit occurred when Prissy was cradling a doll and his “clitty” exploded from the pressure of the doll resting in his lap. He fell back on the floor and moaned.
“Your first lesson, Prissy, is on how to present a neat appearance as you walk to school”, said Janet. She took him by the arm, and marched him to the front door. “You are to walk down to the Girls School, go up to the front door, and try to get in. Of course, its Saturday and it will be locked. So just turn around and walk back here. It’s only about a quarter of a mile each way. You should be back in 10 to 15 minutes”, she said with a smile.
“But it’s Saturday! No girl wears a school uniform on Saturday!” cried Prissy. He immediately bit his tongue as Janet retorted, “Well this girl does, and that outburst is worth a punishment in itself you little sissy. For that, you can make two trips, the second to the Boys School!”
Prissy wanted to shout and scream objections, but quickly realized it would only make things worse. In short order, Janet opened the door, and Prissy was on his way down the walk and up the sidewalk. The four girls followed at a distance behind him, trying to conceal their giggles and glee at the sight of the feminized boy swishing down the street, skirts swaying from side to side, as if his life depended on it.
Prissy reached the Girls School without incident, although he was certain the occupants in every car that passed him were scrutinizing his out of place school clothing. The Boys School was in the opposite direction from Janet’s house than the Girls School, so he dutifully retraced his steps, past the house, and on towards the grounds of his OWN school. As he approached the building he nearly stopped dead in his tracks upon viewing a group of boys playing catch on the front lawn of the school. He turned and looked at Janet and the others, pleading with his eyes to be allowed to go no further. Janet’s smile told him otherwise. He quickly imagined Janet forcing him to go up and talk to the boys, and decided he had no choice.
With his chin buried in his chest he swished on up the walk and tried the door as required. He turned and speeded up his walk down the steps, hoping to get off the grounds without attracting any attention. But the boy nearest to him noticed this odd sight, and turned to stare, just as one of the others threw the ball. It flew passed its intended target, and rolled on the grass, stopping at Prissy’s feet. The ball startled him, and he stopped for a moment. As he started back down the walk, the boy yelled out, “Hey sister!” Prissy looked up as if to say “Do you mean me?” “Throw me the ball, will ya?”
Janet and the others were standing at the corner, eating it all up. Prissy looked dumbly at the ball, and then comprehended that he’d better throw it back or the guy would come over, and he could attract even more attention. The ball players were a good distance from Prissy, and although Perry could easily throw that far, it would give him away as well. So he took the ball and threw it limply from the shoulder, with his weight on the front foot, trying his best to toss the ball like a girl. Worse yet, the unaccustomed motion caused Prissy’s skirt to fly up in the rear as his body twisted in the throw, exposing the white ruffles on his panties to the boys! The dying quail flew only half-way to the boy in the yard, who ran up to grab it, while Prissy hurried on back down the sidewalk. “Nice panties you got there sweetheart!” yelled one of the boys, as Prissy charged ahead, his face beet red, and not daring to look back.
Prissy returned as fast as possible to Janet’s. But the girls took their time, and he was forced to stand on the front steps and wait for them. Much to his relief they finally arrived and let him back in to the relative safety of the house. While Prissy stood there before them, holding his books like a school girl, the girls had a big laugh at the entire episode, and especially at his girlish efforts to throw the ball that ended in revealing his panties to the boys.
Jennifer stood over Perry, with hands on hips. “That deserves a another punishment Prissy. Little girls don’t mess their panties like that when playing with dolls,” she scolded.
Sally again produced the camcorder and required Prissy to lip-sync “I Enjoy Being a Girl” for the camera as a punishment. At the close of the song he had to curtsey and smile for the camera.
It was getting late and Jennifer decided that if Prissy was to spend the weekend arrangements with his Mother would have to be made. “We’re going to allow you to talk like a boy for a few minutes, Prissy. I’m going to call your Mother and want you to tell her that you’ll be spending the weekend with my family at our cabin. She’ll want to know what you’ll be wearing…just tell her that we have plenty of clothes for you to wear!”
The phone call went much easier that Perry expected, and he shortly found himself back in Jennifer’s bedroom with the prospect of spending the entire weekend under the control of the girls.
Sally renewed her idea that diapers were appropriate for such a baby. “She wet her sweet little panties, didn’t she?” This time the girls all agreed, and Perry was given a bubble bath, followed by the girls powdering his body. “Lay down on this mat Prissy,” directed Jennifer. Perry reclined, on the rubber mat laid out on her bed, trying again to cover himself. “Stop that Prissy! You’re a baby girl now, and little baby girls don’t try to cover themselves up,” scolded Karen. “She’s acting like a boy again. That’s another demerit!”
Jennifer rolled Perry over on his stomach and tied his wrists behind him to ensure his cooperation. When he was rolled back he could no longer defend himself from the girl’s assault.
Perry moaned as they manipulated him, but tried to stay quiet for fear of another demerit. His bottom was lifted and Chrissy slid a large, bulky diaper underneath his bottom, fastening it with two large pink safety pins.
The girls brought out Perry’s baby clothes, and he couldn’t help but wonder where they were getting these strange costumes. Like the little girl’s dress, the baby dress was pink, ruffled, and lacy, only more so. And it was short….short enough so that the rows of lace on his rubber baby panties were always clearly displayed beneath the layers of ruffled petticoats. A bonnet was placed over his curly blonde wig, and pink booties tied onto his feet. He was christened “Baby Prissy”, and again taken downstairs for more games.
Baby Prissy was ordered to sit in the middle of the floor as more videotape was taken. “As Baby Prissy you have a few new things to remember,” instructed Jennifer. “Little baby girls don’t talk, and they can only crawl around. And they love to suck on a pacifier when they don’t have their bottle. Would you like your pacifier now Baby Prissy?” she teased. Knowing there was no choice Perry slowly nodded his head. Karen produced a large pink pacifier, certainly adult sized, and placed it near Baby Prissy’s mouth. Perry gasped! It was shaped like an erect penis! He momentarily pulled back, but Karen pushed it forward into his mouth anyway. “This will help train Baby Prissy so that when she grows up she’ll be used to sucking a cock!” laughed Karen. “And I noticed your flinch there Baby Prissy. That’s another demerit.”
The evening progressed, with Prissy sitting on the floor for the amusement of the girls, dressed like a little baby, alternately taking his bottle or pacifier, and constantly being humiliated by the comments thrown in his direction.
“Ooooooh….Baby Prissy”, teased Sally. “I’ll bet you just can’t wait to grow up to be a big girl like us, hmmmmmm? You’ll look so cute in some high heels like these!” And she pranced about in a circle around him on her four inch heels while Prissy lay there on his back, sucking on his pacifier and looking up her long legs to the shadows underneath her short skirt.
It was finally bedtime. The girls took Prissy up to Jennifer’s parent’s bedroom where he was dressed in a long pink silk nightgown. Jennifer drew drawstrings at the hem and wrists, trapping his feet and hands inside.
The girls were up at the crack of dawn so as not to miss a moment of the day ahead. Prissy’s feet were freed from the nightgown long enough for him to walk down to the kitchen, where he was re-imprisoned in the silk gown, and seated at the table. With his hands still tied in the gown, he had no choice but to sit quietly while the girls fed him his bottle and baby food. The four captures had each donned sheer baby doll nighties which did little to hide their charms from him as he sat miserably at the table with a bottle stuck in his mouth and the conversation turned to the day ahead.
“Prissy still seems to be awfully babyish, but we do only have the weekend…..she can’t remain an infant forever”, mused Chrissy as she leaned over and gave Prissy a wet kiss on the cheek.
“Let’s give her dance lessons!” cried Sally. “We could put her in a darling little tutu and teach her to dance the Nutcracker!” she giggled with a gleam in her eye.
“No”, disagreed Karen. “I think she’ll fit into my old Girl Scout’s uniform. She can go door to door and sell cookies!”
“They’re both good ideas, but I think Prissy needs some schooling today” Jennifer stated. “I have just the outfit for her, and I’m sure she’ll appreciate the lessons she can learn from such devoted teachers as ourselves. After all, she’s got a lot of junk to unlearn, isn’t that right Prissy?” she added as she pulled the empty bottle from Prissy’s mouth and smiled sweetly into his downcast face.
Prissy was eventually led from the table and back upstairs, where he was undressed and bathed by the four gleeful girls. Chrissy held the tip of his penis in her hands and scrubbed his groin with a cloth. “My, my, Prissy…..your little pee-pee got such a workout yesterday, didn’t it? But don’t worry. I don’t think it’s broken…..yet!” Prissy hung his head in shame. He had lost all control to these girls, and could do nothing at this point but submit to their indignities. If only they were merely threatening about making him go out in a Girl Scout’s uniform!
After the bath Prissy was led back into Jennifer’s room to be dressed. Laid out on the bed for him was a school girl’s uniform: white blouse, blue and green plaid skirt, knee high’s, mary jane’s and accessories. The underwear was suitably white, although more frilly than what a school girl would ordinarily wear, he figured, and the bra he wore was padded out to an A cup. A bow was pinned into his blonde wig….this one falling in a straight page boy. Only light makeup was applied, and when he was finally presented to himself in the mirror by the victorious girls he couldn’t believe that he looked so feminine. The blouse was buttoned to his neck, which was adorned with a floppy black bow. His breasts gave a hint of pubescent girlhood, and his legs adorned with socks and shoes, were fully exposed below the knee length, pleated skirt. Prissy, the school girl had been created.
Prissy was led back downstairs, where he was handed a small pile of books, and a purse to sling over one shoulder. He earned another demerit when he attempted to hold the books down against his hip, like a boy, instead of cradling them in his arms against his breasts, like a girl.
Meanwhile, Karen unwrapped another tampon, while Sally raised Prissy’s skirt and slip, and lowered his panties. Jennifer maintained her grip on Prissy’s ears, as Karen slowly pushed the tampon applicator into Prissy’s rectum. He grunted and squirmed, but was held fast between her legs. Jennifer squeezed his ears hard, and Prissy resumed manipulating the tampon while Karen repeated identical maneuvers on him.
Chrissy unwrapped another tampon and squeezed next to Jennifer as she placed it in Prissy’s free hand. Soon he was fucking both girls with the tampons, while Karen continued to push and pull the third tampon in and out of his *******. As Jennifer and Chrissy began to moan in unison, Sally reached under Prissy’s skirt and wrapped her fingers around his erect penis, softly and slowly rubbing it through his nylon panties.
“Are you enjoying your hygiene lesson, Prissy?” asked Sally as her hand lingered on his penis. “Don’t you feel just like a real girl now?” she teased. Within moments the two girls grunted and cried out, reaching a simultaneous orgasm. Just as Prissy was about to come though, Sally removed her hand and left him frustrated. “Oh no, Prissy dear”, she chided. “You’ll have to wait your turn.” Jennifer and Chrissy switched places with Sally and Karen, and the entire routine was repeated until they too had come while standing within inches of Prissy’s face.
All four satisfied girls then sat on the floor in front of Prissy, their glistening pussies staring back at his face only a few feet away. With a tampon still stuck in his rear, Prissy was required to sit down on the floor facing them, pushing the tampon in even further. Jennifer smiled, and told Prissy to jerk off for them, “And I want you to tell us how much you’re enjoying your lessons as a sissy, Prissy!”
As if in slow motion, Prissy grasped his prick through the panties, and rubbed it up and down. “I’m having a log of fun”, he said listlessly, in response to Jennifer’s prompting. “You’d better do better than that or you’ll end up learning how to be a little school girl cocksucker”, she warned. And so, his efforts began to improve. As gobs of cum splattered against his panties Prissy wailed “Ooooh! I’m so glad I’m a sissy! Please make me be a girl always!” As his wave of ecstasy crested he crumpled to the floor, slowly weeping at the degradation forced upon him.
It was now midday, and after cleaning themselves up, the girls fixed a quick lunch, and then prepared for Prissy’s afternoon outing. Jennifer described her plans as Prissy slowly picked at the small salad the girls had served him.
“As you probably know Prissy, the Girls School is hosting the Spring Sophomore Prom tonight. Since you’ve learned your lessons so well this morning, I think it’s finally time for you to grow up some more. But you can’t attend the Prom without a dress, now, can you?” she asked, without expecting an answer. Prissy’s shoulders slumped. He had no clothes. He had no way to escape. And even if he did, there was the videotape. He said nothing as he waited to hear his fate.
“And you can’t very well go shopping in your precious little school girls clothes. We’ll have to find you something more appropriate” Catherine added.
The group returned to Janet’s room where yet another outfit was produced, seemingly from no where, for Prissy to don. It was a short, white lace dress, narrow at the waist, and large enough to allow for a B cup bra and falsies. The skirt was decorated with three lace tiers that flared out from his waist. Prissy wore white lingerie, including a garter belt and nude stockings, French style panties, and, for the first time a waist cincher which pulled his stomach in several inches. The 3 inch white leather pumps they placed upon his feet caused him problems until the girls afforded some instruction, and observed him practice mincing around the room, much to their delight. “Prissy, I do declare! You must really be a girl, you look so swishy and sweet!” Sally laughed.
Prissy’s makeup was heavier than before, and the girls re-did his nails, gluing inch long tabs to his fingertips, and painting them bright pink, to match his lipstick. He also wore a new wig, this one in a very full, curly, teenage style, flowing down well past his shoulders in pretty curls. Lauren perfume was added, and Prissy was handed a white leather purse to carry. Katie grinned as she showed Prissy the tampon in the purse, “Just in case `your time of the month’ arrives while we’re shopping!” The other girls also changed into dressier outfits, although they weren’t nearly as fancy as Prissy’s. And off they went in Sally’s parents car to the mall to shop for a prom dress.
Five girls, wearing pretty dresses, attracts a crowd anywhere, and the mall on a Saturday afternoon is certainly no exception. Prissy was placed in the middle of the group, and one step forward from the other girls so that they could observe him and laugh as he swished down the tile floor, heels clicking, purse swinging from his shoulder, and his limp wrist dangling from his arm. “Isn’t this just what a girl likes to do to waste her Saturday, Prissy. Shopping for a new dress!” giggled Katie. Prissy blushed as they approached a large group of boys standing about with the sole purpose to scope out the good looking girls. As he passed the boys one of them reached out and pinched him, causing his companions to squeal with giggles as Prissy wiggled his hips while walking away from the boys, softly rubbing the spot where he had been pinched.
They finally reached their destination, “The Miss Teen Gown Shop.” Prissy was ushered inside where row upon row of prom gowns of all description were displayed. The place was crowded with at least 15 other girls, many with their mothers, there to purchase last minute outfits for the Prom. Janet steered Prissy over to a rack full of long pink, lacy gowns, with full skirts, to be worn over layers of petticoats. “Wouldn’t you look adorable in this one Prissy?” cried out Chrissy, hold one of the dresses up in front of the trapped, feminized boy. A mini debate ensued amongst the girls, each vying to find the frilliest dress for Prissy to wear.
While the group was standing there, another girl approached and greeted Janet. Prissy caught the new girl’s eye and nearly sank through the floor. It was his girlfriend, Susie! “Hi, Susie”, said Janet. “What brings you out here today? I thought you were going to the prom with Perry, and already had your dress?” she added, giving Prissy the eye.
“That lousy little bee! After the debate yesterday I was so mad I went home and tore the damn thing to shreds. I haven’t been able to reach him since then, but I don’t care. You couldn’t pay me enough money to show up at the Prom with him”, she fumed. “Anyway, I have a new date. Hank Meyers asked me to go with him.
Janet turned to Prissy, and said “Susie, I’d like you to meet my cousin, Prissy. She’s in town for the weekend, and we’re here to get her a dress so she can come to the Prom too.” Prissy reached out her hand to limply shake Susie’s in greeting, his cheeks blushing rosily at having to appear in a dress before his girlfriend. He tried to avoid any eye contact with her that might reveal his true identity.
The girls returned their attention to picking out a dress, and finally selected one. They all agreed it was the most feminine dress in the store, a pink chiffon dream, full of lace ruffles, bows, and requiring three petticoats underneath to fill out the skirt. “That’s the dress I was going to wear for Perry”, said Susie. “But I won’t buy it again. I’ve already chosen something else.” “Well I think it’s the perfect dress for Prissy then, don’t you agree girls?” asked Janet, with a knowing smile.
Janet marched Prissy into a dressing room to try on the dress, leaving the others waiting outside. While Prissy was struggling with the mountains of skirts surrounding his legs, Katie, Sally, and Catherine were having a quiet talk with Susie outside. When Prissy made his entrance back into the store, Susie stood with the others, a new smile playing out on her lips. Prissy swished back and forth before the large, triple mirrors as the other girls cheered him on, offering compliments on how the dress brought out his “natural” girlishness. There was no doubt as to which dress to buy after that, but the shopping wasn’t over.
After confirming prior arrangements for payment on the dress and petticoats, which Prissy did not understand, Janet led the group to several other stores to purchase accessories, including matching pink 4 1/2 inch heels, pink lace fingerless gloves, a pink satin clutch purse, and jewelry. Susie joined the crowd for the balance of the shopping trip, offering many suggestions on how to make Prissy look her prettiest. As for Prissy, she tried to avoid Susie at all costs, but the others wouldn’t permit it. So he was forced to act the part of an excitable teenage girl before her, happily purchasing all of the necessary finery for a memorable night at the Prom!
The final stop was an earring booth in the center of the mall. Janet inquired if they had any clip-on earrings for Prissy, but was told “I’m sorry miss, we only sell earrings for pierced ears here. But we can pierce the young lady’s ears right now if she likes.” Prissy started to protest but realized he was swimming against the tide. And with Susie there, and not in the know, he couldn’t very well speak his true fears, even if he dared. “Oooh, but it hurts so much”, he whined, trying the last defense available. “Nonsense”, said Susie. “Your ears will look so much prettier too. And the boys just love pierced ears on a girl. That’s what that wretched Perry used to say anyway!” So while the five girls stood back to watch, Prissy swept her skirt against her thighs, and sat down with knees and ankles together, to await his branding as a confirmed sissy. Pierced earrings, in BOTH ears!
A lovely pair of gold drop earrings was chosen in addition to gold studs, and Prissy was warned to wear the dropped pair for only a short time tonight lest she damage the new holes.
It was late in the afternoon when Prissy arrived back at Janet’s to prepare for the Prom. Since this was only the sophomore Prom, it was not unusual for girls to attend without dates. So at least, Prissy thought, he would escape the indignity of attending on the arm of a classmate. None of the other girls had dates either, preferring to attend alone and try out their luck on the eligible boys at the dance. The house was a flurry of activity as the four girls and one boy competed for space before the mirror in order to primp and preen. Prissy didn’t do much primping and preening however. He had four girls to do it for him!
More videotape was taken of Prissy modeling his stunningly feminine pink gown, and the group posed before a camera set with an automatic timer as well before they left. While Janet and her friends were by no means unattractive, there was no doubt that Prissy was the star. His dress was like a Scarlet O’Hara ball gown, so wide was the skirt. The girls had plucked and fussed with each ruffle until it lay just so over the multitude of petticoats. His makeup was more dramatic than ever. Dark mascara and eyeliner, bright pink lips, and a porcelain complexion amply highlighted with powder and blush graced his face. The girls had spent nearly an hour on his eyes, blending various colors on the lids until they sparkled and shined. His wig from the afternoon had been re-done, and was now piled in a cascade of curls flowing down from where it was gathered in the rear, with wispy bangs covering his forehead. Prissy looked like a pink Prom Princess!
Unfortunately for Prissy, Sally had determined that he was just starting his “period”, and a tampon and applicator was inserted into his rectum before the petticoats were lowered into place. The effect was to create an even more pronounced swish in Prissy’s walk, which the girls agreed made his skirt and petticoat sway very sweetly.
As they approached the door to the gymnasium, Janet stuck the knife in even further. “Now’s your chance to prove just how much you truly like being a sissy, Prissy. Remember how girls `practice how to look pretty so they can trap a man someday into supporting them, and they can stay home and play dolls with real kids!’” she teased? “Well now’s your chance to practice. You’ve got the prettiest dress at the Prom, and we wouldn’t want it to go to waste now, would we? So I don’t want any wallflower acts tonight, although somehow I don’t think you’ll have to worry about that. If I see you sitting alone in a corner I’m going to show that videotape to everyone here.” And she opened her purse to reveal that she had indeed brought the tape with her!
Prissy’s heart was beating a mile a minute as he walked into the decorated gymnasium. The Prom was in full swing, girls and boys dancing on the floor, and milling about the room in many groups. Prissy grasped his skirts in both hands, while still managing to hold his pink satin clutch purse, and stepped girlishly into the room.
Prissy didn’t like the way things were going, but hung tenaciously to his resolve to get out of this situation as soon as possible. With seemingly the millionth curtsey of the day, he sweetly inquired, “Would you like something to drink, Miss Susie?” “But of course, dear. I’ll have a Coke please”, she replied with a wide smile, that turned into a smirk. With a swish of skirts, Prissy turned and went back to the kitchen to fetch the drink. As he returned and served Susie the doorbell rang again.
“Oh, that must be the others”, Susie explained. “I told some of the girls where I’d be. I hope you don’t mind if they drop over too.”
“Not in the least. I’ve got my little maid to assist, and I’m sure it will be no problem at all, right Prissy?” replied Janet. Without any alternatives Prissy agreed, and admitted ten more girls, all of whom he knew from the neighborhood, and whom he had met the night before at the Prom. The throng exploded with laughter as they viewed Prissy, who greeted each in due course with a curtsey, took their wraps, and admitted them into the large living room to join the others. Janet and Susie noted the frazzled look on Prissy’s face as he tried to perform his maidenly tasks and serve such a large group. It seemed he spent more time gracefully curtseying to all of the girls, following Janet’s instructions to the letter, than anything else. And the girls just loved seeing him do it too!
With the additional duties, Prissy forgot entirely about checking his appearance. Within the hour, a small run appeared at the base of each leg, just where Catherine had carefully cut a strand from the stockings while Prissy had been blindfolded and dressed. The wiggle in Prissy’s walk, and the constant pressure from curtseying, exacerbated the runs, and within a few minutes they had crawled up the back of each leg to the top of his stockings, protruding from beneath his frilled, starched petticoats. Once refreshments had been served to each guest, Susie, whom Prissy still thought was unaware of his true identity, called the problem to Prissy’s attention.
“Oh my, Prissy, dear. You’ve got a run in each of your lovely stockings”, she exclaimed, in mock concern. Prissy froze and turned his head to look down at his legs. His face fell as he saw the long runners going up the full length of each stocking. Janet joined in the fun as all of the girls crowded about to see Prissy’s legs. “My goodness! They must be the longest runs I’ve ever seen!” She pulled a tape measure from her pocket, and declared both runs to be 30 inches long. Janet stood back up, and smilingly stared straight into the sissified boy’s horrified face.
“BUT YOU CAN’T!” he screamed in his boy’s voice, stamping his foot. “I WON’T DO IT!” he wailed. Susie stepped back in artificial surprise. “Why you’re not a girl at all! You’re a BOY!” she shrieked. Prissy tried to run from the room, but he was easily outmatched by the large group of girls, and after a brief struggle, found himself standing in the center of a circle of snickering teenage girls. Janet stepped forward and announced to the gathering, “Ladies, may I present Mr. Macho Man himself, none other than Perry, the great debater!” Prissy buried his hands in his face and wept openly as his true identity was apparently revealed for the first time to the assembled girls. Their taunts and jeers were unbearable as he stood before them, his eyes closed to keep their triumphant faces from view, but unable to avoid hearing their deriding comments.
Things eventually quieted down some, and Prissy’s sobbing slowed. Of course, his lipstick had been smeared by his hands, and another day was thus added to his girlish purgatory. Sally produced fresh stockings, and Prissy was required to lift his petticoats, undo his stockings, and replace them before the girls. He found the unfamiliar task was made even more difficult by his long nails.
Prissy was in the midst of serving another round of drinks when the doorbell rang yet another time. Janet offered to get it, since Prissy was busy being a good little “Sissy Maid”. Prissy finished curtseying to the guests after serving the sodas, and turned to see his Mother and older sister, Patty standing with Janet.
“MOM! GET ME OUT OF HERE!” he shouted, again reverting to his male personality. He was shocked to hear her reply.
“And why should I, Prissy. Don’t you like being a girl?”, she teased, while Patty screeched in laughter at her brother’s appearance as a “Sissy Maid”. “I think you’ve amply demonstrated this weekend just what a stupid dupe a male can be. First, you offend every woman by your wretched performance in that debate. Then, you allow yourself to be trapped like this. And you’ve plainly shown just how weak willed you are by adopting the ways of a girl in just one weekend! Didn’t I tell you it would be easy Janet?”
Prissy couldn’t believe his ears! His mother was behind the whole thing? It was unbelievable! “That’s right, sweetie”, she continued. “When I heard you practicing your debate this past week I knew you badly needed an education about ladies and girls. But you’re so thick you couldn’t figure any of it out. Where do you think Janet got all of these clothes? Who do you think arranged to pay for your lovely Prom Dress? And did you think Susie showed up at the gown shop by coincidence, or might a little birdie have told her? You couldn’t even tell that all of these girls knew who you were last night while you carried on like a sweet and lovely Prom Princess with your new boyfriend! And I’ll bet you’re too stupid to realize that your friends here put a cut in your hose earlier to cause those runs up your leg. Oh….by the way, I’m afraid you’ve got two more lovely sets on those stockings as well. I guess you need more practice in `worrying about your stockings’. But that’s ok, because you’re going to have plenty. By my count, you’ve got at least 121 days of practice ahead of you!” And the Head Mistress of the Girls School will be only too happy to keep an eye out on your pretty legs while you spend those days in classes there! But I wouldn’t worry about school too much. You might also want to think about how much time it will take you to earn enough money working as a maid to repay me for your new wardrobe!”
Prissy lost all hope as Janet and Susie dragged him upstairs to change. It seemed the girls wanted to see Prissy play with his dollies “like a good little sissy” while they watched a certain videotape!
He was immediately greeted by Susie with gushing enthusiasm. Indeed, Susie had a whole group of other girls in tow as she approached Janet and her charge. Susie carried the introductions, gleefully noting that Prissy was wearing the dress that she was going to wear for Perry, before he insulted her, and every girl, during the debate yesterday. It was one thing to act like a sissy in front of Janet as his other tormentresses. But now Prissy realized he had to be 110 per cent a girl to avoid detection. But to have to do so in front of Jennifer, Sally, Catherine, and Katie, who knew he was a boy, was just terrible.
Prissy giggled, and laughed. The other girls drew him into conversations about which boys were the cutest, and seemed to collapse into fits of giggles throughout the chat. Without knowing any better, Prissy figured this is what girls must be like when together in a group, so he joined in the fun, as best as possible, in order to maintain his deception. But that seemed to encourage the girls even more, and left Prissy wondering if they all weren’t soft in the head. Being so concerned with himself, and how he had to act, he failed to recognize their fun at his expense, although he was painfully aware of how degrading it all was.
“So com’on, Prissy”, said one girl. “Who’s is the cutest boy here?” she giggled. Prissy scoped the room, wondering what to say. He caught the look of several classmates, and realized how dangerous this was. “Oh, I don’t know. I guess that boy over there is pretty cute” he finally responded, not knowing who to pick, or what to say. The girls squealed, as he pointed out Timothy Fredericks, the quarterback of the football team. “Well let’s see if we can’t introduce you then”, said Susie as she grabbed Prissy’s arm and the two of the swished over in his direction.
“Timothy, I’d like you to meet Jennifer’s cousin, Prissy. She’s a guest here tonight, and was just telling all us girls how cute she thinks you look” Susie said by way of introduction. “Well, you’re a pretty cute babe yourself”, he replied admiringly. Prissy blushed to the roots of his hair at Susie’s revelation, and stood there in his pink prom dress, speechless. “Why don’t you two get to know each other better”, Susie added, and quickly turned and left Prissy in front of Timothy. Prissy was too occupied to notice the large group of girls back with Janet and the others, laughing uproariously at his situation.
Timothy knew a cute girl when he saw one (or at least he thought he did!) and wasted no time in taking Prissy out on the dance floor. To make matters worse, it was a slow dance, and Prissy found he had to place his arms around Timothy’s neck, and allow him to crush his skirt against the boy so that they could be cheek to cheek. In the process, the skirt and petticoats were pressed against Prissy’s nylon’s causing him to erect again. Prissy caught Jennifer’s eye as Timothy slowly twirled him around the dance floor. She gave him a big wink, and a large grin as she lifted the video tape slightly from her purse, and watched as Prissy was held helplessly in Timothy’s arms.
Timothy became an ardent admirer all evening long, and Prissy could do nothing to deter his interest. In between dances, and during breaks, he was constantly at Prissy’s side, holding hands, or placing his arm around Prissy’s small, cinched waist. By the end of the night, Prissy had danced with several other boys, all of them classmates, and none of whom appeared to recognize him in the least. But Timothy was persistent, and managed to keep most of the dances for himself. When Timothy and Prissy were named Prince and Princess of the Prom, the crowd went wild, especially a large contingent of girls standing with Jennifer!
As Prom Princess, Prissy was required to tour the entire gymnasium on Timothy’s arm to the applause of the whole gathering. Jealous girls looked on, and Prissy was so concerned with the exposure he nearly fled the room. But somehow he gathered himself, and minced along, waving his gloved hand like a beauty queen, his skirts swishing with each movement, the tampon, seemingly permanently wedged into his bottom, adding an additional wiggle to his hips with each step.
When the evening neared its end, Prissy found himself in Timothy’s arms again, slowly swirling on the dance floor for the last dance of the night. Timothy maneuvered Prissy into a dark corner, and as the song ended, tilted Prissy’s head up to his, and planted a long, deep kiss, on Prissy’s glossy pink lips. Having spent the last 24 hours as a girl, there was little he could do but respond to the kiss. To do otherwise would only risk detection, he feared. But OOOHHH! To kiss another boy like that! While wearing a pink prom dress, and with Janet and the other girls watching!
Of course, Timothy insisted on driving Prissy home, and Janet readily assented. Prissy looked at her with wide eyes, begging her not to do this to him. But Susie thought it was a great idea. “I’m so glad I was able to bring you two together”, she said with a broad smile. Prissy could do nothing but rest her head on Timothy’s shoulder as he held her tightly about the waist. “Don’t be too late now”, Janet called out as Timothy helped Prissy into his father’s car, and drove off.
Two hours later, Prissy was returned to Janet’s house. The girls had changed into negligees, and were waiting up for him. They immediately pestered him with questions about what had happened with Tom. Prissy’s makeup was smeared, and he looked dazed as the girls made him stand in the center of the room, and relate what had happened. He stood there briefly, and then burst into tears. “He was horrid!” he cried as he buried his face in his hands.
“Ooh. Don’t cry now dear. Since you’re having a hard time verbalizing your experience, Prissy, why don’t’ we just act it out.”
Janet and company slept late Sunday morning. When Prissy finally awoke, he shuddered and nearly felt nauseous at all he had endured yesterday. He had been forced to give a blowjob to the “Prom Prince”……and then forced to reenact it for Janet and the others! And all the time while dressed, and ACTING as a teenage Prom Princess!
He was utterly despaired as Janet pulled him out of bed and dragged him to the bathroom. “It’s only Sunday, Prissy. You still have a full day as a sissy yet ahead”, she gloated. After a bubble bath, Janet slipped a sheer pink negligee on him, and led Prissy back to the bedroom to be dressed once again. Katie, Catherine, and Sally were waiting for him.
“Since you’re all grown up now Prissy, we’ve decided that you should learn some skills that will help you be a working girl some day”, said Janet. “But we want your outfit to be more of a surprise than the others. So before we put any clothes on you, we’re going to do your makeup and hair.” The girls sat Prissy at the vanity and worked him over. Compared with his makeup from the night before, he now appeared more grown up…..even glamorous. The pink lips and nails from Saturday became bright red on Sunday. Yet another long blonde wig was securely pinned to his head, the masses of curls sweeping down over his shoulders, halfway down his back. All of this was performed with a towel draped over the mirror so that Prissy couldn’t see the details of the girls’ work. “You’re going to be sooooo darling when we’re finished”, Catherine laughed as the girls finished up.
Janet finally took a black scarf and tied it around Prissy’s head so as to prevent him from seeing the remainder of the transformation, but not so tightly as to mess his makeup. Panties, a real boned corset, stockings, heels, and bra followed in short order. A slip, unlike any Prissy had worn so far was drawn up his legs, and a dress was carefully dropped over his wig and zipped up the rear. He could feel the girls making final adjustments, fiddling with his hair, and tying a bow at the rear of his waist. Last, his feet were crammed into the highest heels he’d yet worn…..a full five inches!
Later that morning, Prissy was instructed to prepare and serve brunch. The girls casually sat about the table reading the Sunday paper as Prissy slaved away, setting the places, cooking the food, and then serving his “employers”. The girls frequently took opportunities to have Prissy wait hand and foot on them, despite the fact that he was already quite busy with his appointed tasks. “Prissy, would you be a dear and hand me the sports section of the paper”, asked Katie with a wide grin on her pretty face. Of course, Prissy answered “Yes Miss Katie”, and minced in from the kitchen. He paused at the doorway and curtsied as required, swished over to where Katie was seated, and lifted the paper from the table only a foot away from her, placing it carefully in her hand. Prissy curtsied again, and demurely inquired, “Will that be all, Miss?” Upon receiving her acknowledgment, and the brief conversation being at an end, he dutifully curtsied, walked back to the doorway with the small steps forced upon him by the high heeled pumps, turned and performed yet another curtsey before leaving the room to continue with the brunch preparations. A few seconds later, Catherine wanted the television section, or some other small request was made, and the entire ritual was repeated again for the amusement of the girls. Even though it had been several hours since they had first dressed Prissy as their maid, the girls couldn’t help but giggle and laugh as they watched him prance about.
Seemingly hundreds of curtsies later, brunch was eventually completed, and Prissy was put to work straightening out the living room, first vacuuming the floor, and then cleaning the tables and lamps with a feather duster. He was becoming increasingly confident of his ability to weather this ordeal when the doorbell rang.
“Prissy hon, will you get that please?” asked Janet, who was in fact seated only a few feet from the door at the time. “And don’t forget to greet whomever it is with a curtsey!” A flash of fear crossed Prissy’s face as he considered the implications of appearing in these clothes before others. But he was clearly without a vote in the matter, and performed his curtsey ceremonies in reply to Miss Janet’s request before crossing to the door and opening it. A beaming Susie greeted Prissy as he swung the door open.
“Hello Prissy! My isn’t that the cutest little outfit though?” Susie said in greeting, as she walked inside and looked Prissy over from head to toe. “Prissy, maids curtsey when they greet guests at the door, or have you already forgotten?” Janet called out. Submitting to what was rapidly becoming “Curtsey Madness”, Prissy gathered his senses and quickly grasped his skirts and bent his knees to Susie, all the while trying to figure out what was going on. Susie charged past him to join the others in the living room.
“I thought you told me Prissy was your cousin Janet. I didn’t know she was also your maid”, Susie goaded. Janet and the others remained silent, and Prissy finally figured that it was left up to him to explain his subservient status. “Oh this. Janet and I like to make bets a lot. I lost the last one and I’m her maid today as a result”, Prissy said, trying to act casually about the whole matter. “Well whatever the reason, Prissy, don’t start thinking you’re just `one of the girls’ while wearing your precious little outfit. Don’t forget your place!” Janet responded. She continued, “And don’t forget to ask my guest is she’d like some refreshments.”
