Peter 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 Peter 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. Jennifer seemed to be upset and spoke first. “Oh Peter, 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 Peter, 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.” Peter 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 Jennifer smiled wickedly behind his back and replied, “Oh I don’t know about that.” Peter swung his leg through the window and disappeared from view.
Two hours later Peter was standing before a mirror, tears forming in the corners of his fifteen year old eyes. He was dressed like a six year old girl and was surrounded by a giggling Jennifer and three of her classmates. It had all happened like this: Once in her room he was immediately jumped by Jennifer’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 Jennifer appeared at the door with a big pair of scissors. “Well, Peter dear, it seems that girls can be a match for boys, don’t you think?” she sneered. “What’s going on here,” Peter shouted. “Let me up now or I’ll . . .” “You’ll what, sweetie?” Chrissy 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!”
Peter started to scream and shout, but his ranting only resulted in a gagging. Jennifer took off her black lace panties and ceremoniously stuffed them in his mouth, tying them securely in place with a scarf. He was lifted to his feet, his clothing swiftly cut off his body, and he stood there naked and bound while the girls teasingly covered him body with Nair. “We’re going to get rid of all that nasty hair Peter so that you’ll be smooth all over, just like a girl,” Karen 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 naked condition and without any male clothes. He knew it too.
Peter allowed the girls to lead him back to Jennifer’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,” Jennifer 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, and to Peter’s horror, as the soft material glided against his smooth skin he felt his penis harden. “Oh look girls,” Chrissy cried. “Peter likes his sissy little panties!” Peter was shamed beyond belief as he stood there before the four laughing girls, his hard-on bulging against the front of his pink lacy panties. A pink vest, matching his panties, was pulled over his head, and as he lowered his arms a bright flash blinded his eyes. Karen 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 Peter’s panties. “She looks too cute to be a boy anymore,” said Jennifer. “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”, Jennifer teased.
Peter 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,” Jennifer responded. The girls marched the sissified boy over to the vanity bench and sat him down. Chrissy 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,” Jennifer 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.
Prissy was led back to the bed where the dress lay and was again given the opportunity to humiliate himself. He took it, stumbling over the words. “Oh Jennifer, its such a pretty little dress. Can I please put it on and show you what a good little girl I can be?” The girls made him repeat this several times, first in a feminine lisping voice, and then followed by a curtsey to each of his tormentors. Finally satisfied, the girls drew the short, pink, little girl’s party dress down over his head and buttoned it up the back, its short skirt billowing out over the stiff, rustling petticoat. A wide pink sash was added. Prissy was required to pirouette for the girls, and another fit of giggles ensued when they spied his hard penis underneath the frilly panties. Prissy was then led back over to the vanity for her makeup.
“Little girls like you don’t usually wear much makeup Prissy, but since you seem to have some trouble adjusting to being a sissy, we think it’s appropriate,” laughed Karen. In short order the girls applied makeup, mascara, blusher, eye shadow, and bright, glossy pink lipstick to his features. Jennifer triumphantly pinned a blonde wig covered with sausage curls to his head, and placed a large pink bow at the rear. As the final touch he was given a tiny white patent leather purse to slip neatly over his wrist. With that, Peter, now Prissy, was placed in front of the mirror to view his new image. If the clothes and laughing girls were not enough, his humiliation was complete as tears began to form, and drop down his cheeks. He was the perfect image of a little sissy girl.
“Look girls”, Chrissy cried out, “Prissy even cries like a little sissy!” Peter tried to turn away from the extraordinarily effeminate image in the mirror but was grabbed by the girls and forced to stand before his embarrassing reflection. He finally gave up his struggle and stood there passively. As he stared at the mirror he could not ignore the hardness between his legs. Combined with the humiliation heaped upon him by his tormentors, he was utterly confused by his arousal and unable to defend his masculinity.
After several minutes, during which the girls crowded around him, primping his hair and fluffing out the lacy ruffles on his dress, Jennifer and the girls stepped back, leaving Prissy alone to view himself in the mirror. Jennifer instructed Prissy to open his purse and take out the paper inside.
“I want you to read what’s on the paper, Prissy, and look up in the mirror while you do so….as if you had a big audience out there” Jennifer giggled. Prissy unfolded the paper and glanced down at the prepared speech.
“Oh com’on Jennifer! Haven’t you had enough of your fun?” he wailed after reading several of the lines.
“Not in the least….but I’ll tell you what. You read your lines, and do your best to sound like a pretty little sissy girl such as you look right now, and you’ll only have to wear that dress for a few more hours today”, Jennifer replied. “But if you don’t, things will only get worse!” she threatened.
Prissy composed himself, and read through the short speech to familiarize himself with it. Ugh! How was he going to say all of this stuff? Finally, with further prompting from the girls, he readied himself before the mirror, performed a curtsies instructed at the top of the page, and began.
“Hello. My name is Prissy, but you may have remembered me from earlier today when I pretended to be a boy named Peter, and debated about woman’s rights at school. A lot of girls were mad about the things I said, but I’m not here to apologize for it. I think everything I said was true, and I know, because I just love to dress up and be a pretty little sissy named Prissy! I hate wearing ugly boys clothes, and can’t wait for every chance to wear darling clothes, like this adorable dress, and do all of the things I talked about today at school, like play dress up, and house with my dollies, go shopping, and try to look my prettiest for the boys. But wearing pretty dresses isn’t enough for me. I love to wear all of the frilly little undies too, like my ruffled panties (Prissy turned his back to the mirror and flipped up his skirts to reveal the many layers of white lace on his pantied bottom), my sweet lace frilled petticoats (Prissy lifted his skirt in front to reveal the layers of lacy taffeta), and special touches like my makeup, nail polish, and this cute little ribbon bow in my hair. I don’t know why the girls got so upset. I’d much rather be a little sissy girl than a boy!” Prissy concluded by blowing a kiss to the mirror, and dropping another deep curtsey to himself.
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.
Jennifer 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. Peter 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. Jennifer 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. Jennifer spoke next.
“Prissy darling, it’s now time for you to repent for your inexcusable behavior today at school. A very nasty boy named Peter 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?”
Peter stood there dumfounded again. “You . . . you mean I have to do this all weekend?” “That’s one demerit,” grinned Karen.
More tears formed on Peter’s face as the enormity of what he faced sank in. “Do you understand?” repeated Jennifer.
“But, but you said I could have my clothes back in a few hours…….Please, can’t we talk about this, please?” implored Peter, now feeling as if the quicksand he had climbed into through the window was nearing his neck.
“And that’s two demerits,” joined in Chrissy. “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 Jennifer. “Now do you understand, or do you continue to accumulate demerits?”
Peter nearly broke out sobbing, but he got the message. “Yes, Jennifer, I understand,” he whispered.
“Great,” smiled Jennifer. “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.” Karen 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 Chrissy. I’m sure you’d just love to have this tape circulate around at school, huh? Can you imagine? Macho man Peter 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 Jennifer. “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 Jennifer declared that a punishment was indeed in order. Still sobbing, Karen and Chrissy grabbed Prissy’s wrists and pulled him down over Jennifer’s lap. His skirt and petticoat were raised high up his back, revealing the pink rumba panties in all of their glory. Jennifer slipped the panties down Prissy’s legs, and began to slap his bare bottom, while Karen and Chrissy 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. Jennifer 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 Jennifer. Prissy paused, shifting his weight from one leg to the other, trying to get some relief for his sore bottom. His erection, which had not subsided since he first wore the pink rumba panties in the bedroom, seemed like it was on fire as well. 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 Chrissy. “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, rubbing the doll against his penis to increase the ecstasy of the experience.
Jennifer stood over Peter, 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. Karen wanted Peter to lift his skirt and petticoats, drop his panties, and scoop some of the cum into his mouth. But Jennifer interrupted her. “No, Prissy is still a little girl. She’ll have to grow up a little bit before that!”
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 Peter 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 Peter was given a bubble bath, followed by the girls powdering his body. “Lay down on this mat Prissy,” directed Jennifer. Peter reclined, naked, on the rubber mat laid out on her bed, trying again to cover his nudity. “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!” “Besides”, added Sally, “We like looking at your little pee-pee.”
Jennifer rolled Peter over on his stomach and tied his wrists behind him to ensure his cooperation. When he was rolled back he could no longer defend his genitals from the girl’s assault. His hairless prick began to harden again as Sally held the tip of it between her fingers and slowly twisted it back and forth. “Such a cute, itty, bitty, pee-pee”, she cooed, as Jennifer slowly oiled the shaft, his balls, and his puckered anus with Baby Lotion. Peter 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 Peter’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 Peter slowly nodded his head. Karen produced a large pink pacifier, certainly adult sized, and placed it near Baby Prissy’s mouth. Peter 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 sexy 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 all stripped naked before him and climbed under the sheets to sleep with their “Baby Prissy.” Peter couldn’t resist them as they stroked his body through the soft silk of the nightgown. He came three times in his diapers before they all drifted off to sleep.
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.
“Your first lesson, Prissy, is on how to present a neat appearance as you walk to school”, said Jennifer. 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 Jennifer 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, Jennifer 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 Jennifer’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 Jennifer and the others, pleading with his eyes to be allowed to go no further. Jennifer’s smile told him otherwise. He quickly imagined Jennifer 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?”
Jennifer 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 Peter 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 Jennifer’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. Then Jennifer announced the next lesson: FEMININE HYGIENE!
Prissy was seated in a chair in the living room while all four teenage girls undressed before him until they were each naked. “I’m sure you’re aware that all girls have a period, Prissy. Have you had your first one yet?” Jennifer inquired with a smile. “No”, he replied. “Well this is a vagina…..you know, the part of a girl’s body that boys call cunts! You’ve never used that word, have you Prissy?”
He shook his head, wondering what they could do if he had admitted the truth. “That’s good. Now, get down on your hands and knees, and look at our vaginas up real close.” In a daze, Prissy got on his hands and knees and leaned his head in towards Jennifer’s bush. As he got closer he couldn’t help but notice the musky odor that emanated from between her legs. Jennifer grabbed his ears and held him closer, until he was only inches from her crotch. Prissy repeated this examination on each girl in turn.
With Prissy still on the floor, Jennifer reached into a bag and brought out a box of tampons. “I’ll bet you haven’t ever used a tampon before either, have you Prissy?” “Oh I don’t know about that”, joined in Sally, with a wide smile. “I’ll bet Prissy plays with tampons all the time.”
Jennifer laughed, and unwrapped the tampon, handing it to Prissy. “Now, Prissy darling, this part takes some practice. I want you to slide the tampon into my vagina, nice and slow.” She grabbed him by the ears again, and held him close, so that he had a bird’s eye view of her lips as they parted to accept the tampon. “In and out now Prissy, nice and slow”, she moaned. “Wiggle it around a little. That’s it. Oh…..oh…..what a good little sissy you are Prissy.”
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” Chrissy added.
The group returned to Jennifer’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. Karen 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 Karen. 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. Jennifer 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 Jennifer. Prissy caught the new girl’s eye and nearly sank through the floor. It was his girlfriend, Susie! “Hi, Susie”, said Jennifer. “What brings you out here today? I thought you were going to the prom with Peter, and already had your dress?” she added, giving Prissy the eye.
“That lousy little ****! After the debate yesterday I was so mad I went home and tore the **** thing to shreds. Somebody ought to castrate that *******! 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.
Jennifer 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 Peter”, 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 Jennifer, with a knowing smile.
Jennifer 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, Karen, Sally, and Chrissy 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, Jennifer 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. Jennifer 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 ****-head Peter 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 Jennifer’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 Jennifer 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, Jennifer 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.
He was immediately greeted by Susie with gushing enthusiasm. Indeed, Susie had a whole group of other girls in tow as she approached Jennifer and her charge. Susie carried the introductions, gleefully noting that Prissy was wearing the dress that she was going to wear for Peter, before he insulted her, and every girl, during the debate yesterday. It was one thing to act like a sissy in front of Jennifer 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, Chrissy, and Karen, 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 Tom 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.
“Tom, 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 Tom. Prissy was too occupied to notice the large group of girls back with Jennifer and the others, laughing uproariously at his situation.
Tom 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 Tom’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 Tom 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 Tom’s arms.
Tom 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 Tom was persistent, and managed to keep most of the dances for himself. When Tom 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 Tom’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 Tom’s arms again, slowly swirling on the dance floor for the last dance of the night. Tom 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 Jennifer and the other girls watching! Their tongues mingled, and even through the skirts and petticoats, Prissy could feel Tom’s large erection bulging under his pants.
Of course, Tom insisted on driving Prissy home, and Jennifer 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 Tom’s shoulder as he held her tightly about the waist. “Don’t be too late now”, Jennifer called out as Tom helped Prissy into his father’s car, and drove off.
Two hours later, Prissy was returned to Jennifer’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.” She produced a 16 inch double ended rubber dildo, painted to look like an erect cock on both ends, and placed one end in her pussy. Karen and Sally took Prissy’s arms and forced him to his knees before Jennifer. “Com’on, Prissy. Show us how you sucked Tom’s cock!” ordered Chrissy, as she grabbed his head and forced his mouth onto the dildo. After several moments, Prissy stopped sobbing, and then resisting, and Karen and Sally released his arms. He grasped the dildo with his pink tipped fingers reaching out from the pink fingerless lace gloves, and began to deep throat the dildo while the girls urged him on. Karen and Sally reached down and swished Prissy’s chiffon skirts and petticoats back and forth over his legs, while Chrissy whispered into his ear, “That’s it, Prissy, show us what a sissy Prom Princess cocksucker you are!” Several more hours later, after Prissy had sucked the “cock” of each girl, they retired and quickly fell asleep.
Jennifer 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 Jennifer and the others! And all the time while dressed, and ACTING as a teenage Prom Princess!
He was utterly despaired as Jennifer 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, and a check to assure that Prissy was still hairless, Jennifer slipped a sheer pink negligee on him, and led Prissy back to the bedroom to be dressed once again. Karen, Chrissy, 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 Jennifer. “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”, Chrissy laughed as the girls finished up.
Jennifer 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!
With a girl on each wrist, Prissy tripped over to the full length mirror and the black scarf was removed. He blinked his long lashes and stared at the image of a sexy, pretty, French Maid! The girls rolled on the floor with laughter as they saw his surprised and alarmed look.
Prissy wore the authentic uniform of an alluring, flirtatious French Maid. The black satin dress was trimmed in white lace around the scooped neckline, short puffed sleeves, and hem of the very short skirt, which was held out at a wide angle by stiff, short, white petticoats. A white taffeta, full bibbed apron lay on the front of the dress, and appeared like a pinafore due to the wide lace ruffles that trimmed the straps over Prissy’s shoulders, and met at the rear waistline in a large bow. His waist was neat and trim, due to the compression of the boned, black satin corset the girls had forced him to wear, and its cups were filled with silicone, C cup falsies which jiggled and swayed with every movement. Prissy’s black patent leather pumps were indeed five inches tall, perching his feet on heels tips smaller than a pencil eraser. His hose was sheer black silk, with a seam running up the back, and the tops of the stockings and garters could be seen just underneath the skimpy skirt. A lacy cap had been pinned into the curly mane of long blonde hair, and he again wore the dangling gold earrings from the previous evening. His makeup was spectacular: bright red lips, dark, dramatic eyes, and brightly rouged cheeks. Prissy’s inch long nails had been replaced with inch and a half, narrow, red spikes, and she had been liberally perfumed. The dress and makeup created such a new look that Prissy looked like an entirely different person than the Prom Princess from the night before.
Jennifer regained her composure sufficiently to turn Prissy around and bend him over revealing a multitude of white lace ruffles on the sheer nylons panties covering his bottom. The final touches were the words embroidered in black script on the front of his apron: “Sissy Maid”.
Prissy again found himself at a loss to gain any control over the situation. And as on Friday afternoon, he stood submissively before the mirror and allowed the girls to crowd about, teasing and laughing at his effeminate image. He was ordered to model his uniform for them, allowing his hands to dangle limply from his wrists, or primping his hair, and further instruction in walking with heels, ensued. Of course Prissy was only in the second day of her period, and a tampon had been inserted by Karen while dressing him. “If you’ll stop trying to take large steps like a boy, Prissy, you’ll have no problem swishing about in your pretty shoes!” coached Chrissy. Having experienced wearing heels for hours the day before, Prissy was soon mincing about in the five inch spikes without too much difficulty.
Jennifer ultimately quieted her friends down, and stood Prissy in front of the mirror once more while she explained his duties for the day. “Now you’re a grown up girl Prissy. See how much progress you’ve made in such a short time? Today you’ll serve us as our maid. We tried to think of some other suitable position for you, but none came to mind!” she teased. “So from now on you will address each of us by our name, preceded by the title `Miss’. That’s a nice sweet way for a maid to address pretty girls like us, don’t you think? The rules are that you don’t speak unless spoken to. When you do speak you will always do so in an appropriately girlish and respectful voice. You will curtsey each and every time you are spoken to, and each and every time you enter or leave a room. The earlier rules also apply. You are a GIRL! And a serving GIRL at that! Anything that belies your femininity or subservience will result in demerits, and punishment. Oh, and one last thing. Remember in your little speech on Friday? When you told everyone how when a girl gets a real job `All she does is worry if her stockings have runs, or if her makeup is on straight!’ Well you’ve got a real job now, and we expect the same from you. I’m afraid that if you get a run in your stockings we’ll have to extend your time in skirts though. What do you say girls? How about one more day as a girl for each inch of a run in her precious stockings?” “Sure”, replied Sally. “And that should go for her makeup too. If her lipstick needs a touch up and we have to point it out to her I think she should get another day as well!” “Right”, added Jennifer. “But remember Prissy, if you perform as expected, and required, we’ll even give you the videotape and pictures we took. But until then, you’re on duty, got it, Miss Prissy?”
Prissy stood there and easily realized the challenge he was faced with. But somehow he saw a light at the end of the tunnel. It’s only one more day, he thought. If I can handle this I’ll get the tape back and can put this entire weekend behind me. And of course, there was revenge. He didn’t know how, or when, but he knew he would have his. Grasping his skirts with both hands, Prissy dropped a neat little curtsey, and said “Yes, Miss Jennifer. I understand”, in a girlishly high voice that sent the others into a fit of laughter. Of course, if he scowled or expressed any displeasure at all, he knew he’d be punished. Prissy figured he was learning their game. So he stood there quietly, hands folded neatly on his apron, and waited for their next command.
Bathing and dressing four girls is a lot of work, and Prissy learned that first hand in the next 2 1/2 hours. Starting with Jennifer, he carefully undressed each one, drew a warm bath, bathed and sponged their ENTIRE bodies, dried and powdered them, performed a pedicure and manicure, and assisted in dressing the girls. He knew he was continuously in danger of violating one of their rules, and was mindful to constantly check his lipstick, and carefully protect his stockings from any contact that might cause a run. He had been given a compact mirror and lipstick which Prissy placed in a small pocket in his apron. The girls got quite a thrill from observing him follow his own description of the working girl, pausing every few minutes to pull out his mirror and check his lipstick, and occasionally adding another luscious red coating to his lips as additional protection.
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 Karen with a wide grin on her pretty face. Of course, Prissy answered “Yes Miss Karen”, and minced in from the kitchen. He paused at the doorway and curtsied as required, swished over to where Karen 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, Chrissy 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 Jennifer, 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 Jennifer’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?” Jennifer 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 Jennifer. I didn’t know she was also your maid”, Susie goaded. Jennifer and the others remained silent, and Prissy finally figured that it was left up to him to explain his subservient status. “Oh this. Jennifer 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!” Jennifer responded. She continued, “And don’t forget to ask my guest is she’d like some refreshments.”
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 Jennifer. 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. Jennifer 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 Jennifer’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 Chrissy 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. Jennifer 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. Jennifer 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. Jennifer stepped forward and announced to the gathering, “Ladies, may I present Mr. Macho Man himself, none other than Peter, 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. Jennifer 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 Jennifer.
“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 Jennifer?”
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 Jennifer 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 Jennifer 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!