Note From Sapphire:
Somehow the text copy of this story that has been on the site became corrupted, and was incomplete until now. I want to thank " Baby Kim " of " Sissy Kiss " website for sending me this complete story to offer it for our readers.
The Story of Prissy
by Linda Lafrance
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
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",
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.
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
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?"
"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
"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
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.
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
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
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
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
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.
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
"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
"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
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
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
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 asshole. 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,
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 shit! After
the debate yesterday I was so mad I went home and tore the damn thing to
shreds. Somebody ought to castrate that asshole! 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 shit-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
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
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
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
"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
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:
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
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
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
"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
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
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!