Miss Prissy Paunceworth - Chapter II, Prissy's First School Day
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This is a female authoritarian sissy boy story, although with a softer
touch than most. There is sugar and spice and (mostly) everything sissy-
nice! So, if lots of frilly outfits, swishy behavior and a little kinky
sex are your thing, please read on. If not, thanks for looking anyway.
Miss Prissy Paunceworth
It is also a purely fictional fantasy work. No references are intended
to portray any actual persons, places or events whether past or present.
This chapter is rated R, but future chapters will be rated X. Please be
of appropriate age or be gone!
Chapter II – Prissy's First School Day
Moving his sleepy body under the soft covers Peter sensed change. Never
had he slept with such dreams. It was almost as if some sexy woman was
whispering in his ear all night.
His last dream had startled him awake. In it, he was dressed in the most
amazing frilly outfit and was actually kissing another similarly dressed
boy - and loving all of it!
The softness across his titties and the smooth feeling about his bottom
felt so very nice. However, the sticky wetness about his front seemed
strange. His first thought was that he had wet his bed, but his fading
erection told him something far different.
Reality dawned as his eyes focused on the bright morning sum coming
through the fluffy organza curtains.
"Merstead Hall, sissy, Miss Tellit," all ran through his mind in a
flash. "What happened yesterday just could not be true! No way!"
However, the pink walls and over the top girlie trimmings of his room
confirmed where he was. His darling little babydoll night gown confirmed
what they had made him into.
"This is all too weird. What have I gotten into - heaven or hell?" he
"Good morning, my sweet prissy sissy," chirped Miss Tellit as she
entered Peter's room carrying a shopping bag.
"Ugh," sighed Peter.
"Remember, no speaking," admonished Miss Tellit. "And that is hardly the
proper way to greet your mistress! We have much to do to get you ready
for your fist school day. Up and at 'em, sis! You should feel much
better today. That little sedative Doctor D'Oley gave you yesterday
should have worn off."
Only half listening, and entirely missing the point, Peter was far more
interested in Miss Tellit. She was becoming his beautiful fairy
Today she was wearing a soft white silk notched collar blouse over a
pink chintz short skirt. Sandal colored stockings traveled down her long
shapely legs to a divine pair of pink high heels that excited Peter to
no end. Kissing her heels last night had been so thrilling!
Her blouse's sheer fabric showed the outline of the lace bra that lay
beneath its soft folds. Her long honey brown hair cascaded past her high
cheekbones down to her blouse's soft collar. The naughty remembrance of
kissing her small perfect breasts caused Peter's peenie to stir anew,
despite its very recent release.
"On my God," he thought, "I really did that! She actually let me suck on
As Peter rose from his bed he tried in vain to hide the little
'embarrassment' in his panties - now compounded by a stiffening peenie.
"Well, well, well, was my little sissy having some nice dreams?"
chuckled Miss Tillet, who was secretly delighted with the 'outcome' of
the young sissy's dreams.
"Not to worry, my dear," she continued. "It is perfectly natural for a
sissy to make little 'messies' in her panties. Now, put on your mules
and come along to the loo. But later we will want to know exactly what
you were dreaming of when your little peenie exploded!"
Peter responded with a deep blush that told Theodosia Tellit everything
she needed to know - or, more precisely, already knew.
Miss Tellit continued, "Peter, I will help you with your morning
preparations for this first week, but after that you will be on your
own. And, as we will demand perfection, you will be well advised to
learn both rapidly and thoroughly."
Arriving in the bathroom, she first put his hair up in a fluffy pink
shower cap and showed him how to tend to his newly pierced ears. Next,
she supervised Peter taking the pills the doctor had prescribed.
She then directly Peter to brush his teeth and scrub his face while she
opened the tub's faucets and added a vial of lilac scented oil. Those
tasks completed, she told him to take off his nightie and hand it to
her. Discarding the top in a nearby hamper, she carefully inspected the
"Oh, Peter, you really are such a sissy. You certainly did have quite an
'accident,'" she exclaimed. "Just look at all this sweet sissy cream.
It's still warm and all gooey. My-my, all this from such an itty-bitty
clitty! Whatever 'were' you dreaming about?"
With that, she scooped up a little semen with her index finger and
cooed, "Mmmm, so sweet."
Peter's heart began to pound as she slowly brought her finger to her
mouth to lick his sissy cream and then took her whole finger into her
mouth to softly suck off the remainder. The poor boy had never been
confronted with quite like it.
Still cooing, she said, "Peter, you are sooo tasty! I bet you want some
too. Don't you?"
Peter started to withdraw, but Miss Tellit's exaggerated frown quickly
arrested his retreat.
"You 'do' want to please your mistress, do you not, Peter?" she said.
"That's a good sissy." Scooping up another dollop from his panties with
her long elegant finger, she added, "Yes, now lick your yummy cummy like
the perfect little sissy you are."
A very reluctant Peter tentatively licked the pearly drop from her
finger, forcing back a gag reflex at its sticky salty taste.
"Good girl, now let's clean it all up. Show Mistress how much you like
it and I shall be well pleased, and you 'do' want to please your
mistress, do you not, Prissy?" she teased.
It took three additional scoops for Miss Tellit to finish. With the
final offering, she worked her long finger in and out of Peter's mouth.
"Yes, you like sucking my finger, don't you, sweet sissy? But of course
you do. All sissies adore sucking things. It just comes so naturally to
you, doesn't it?" she rhetorically asked, neither needing nor expecting
a reply from the gagged boy.
"Well, that's enough fun for now," she said. "First thing is to douche
Miss Tellit directed Peter through giving himself an enema followed by a
sweeter, slightly oily douche and then showed him proper feminine
Still both tasting and feeling his slick sissy cream in his mouth, Peter
dried off with a huge fluffy pink towel ("Pat, don't rub.") and applied
three different moisturizers - a special one for his titties and fanny,
another for his face and a final one for the rest of his body ("Caress
yourself with the creams - revel in the luxurious feeling.").
Lastly, Miss Tellit handed Peter a four-inch soft pink jellied tapered
tube with a flat base and flanged bottom. Its base tampered down to a
half-inch flange, after which it increased to a full inch before again
tampering off to a slim rounded head.
"Sweetie, it's time for your 'fanny friend.' Now be a good girl and put
it up your sissy pussy all by yourself. Here's some lubricant. I suggest
you first apply it to your little sissy hole and then the plug, itself.
Use a generous amount - we do want you to be comfy all day!"
She watched with satisfaction as a totally compliant Peter first
lubricated his rosebud and then the plug, adding, "I suggest you raise
one leg on the side of the tub as you insert it."
To Miss Tellit's absolute delight, Peter emitted the cutest little sissy
squeak as the plug went it.
Morning ablutions complete, Peter donned a white silk robe, slipped into
his mules and went to sit at the makeup vanity table ("Mind your
deportment as you sit. Right - now straight back, head up, arms tucked.
And stop rocking about on your 'friend,' you shameless hussy!").
"Now, Peter, I understand you were napping yesterday where these were
used, but it's time to do your morning tittie training. Watch carefully
as I put them on you."
First she opened up his robe and attached tiny electrode patches to each
side of his titties. Each patch was connected by a thin wire to a
control box mounted in the vanity-dressing table. Next she placed two
conic cylinders over his entire breast area. The cylinders were
connected by an elastic band that went about his chest and fastened
between the cones. Each cone had a thin hose extending from its tip to a
junction, to which Miss Tellit attached a single hose extending from a
pump also mounted in the dressing table.
"Most sissies find this very pleasant once they become accustomed to it.
Ready, here comes part one!" Miss Tellit said as she turned a dial on
Peter watched in near disbelief as his breasts slowly expanded in the
cylinders. They grew to an unbelievable size. It was all he could do not
to cry out in amazement.
As she turned a second dial, she said, "Now, part two."
The electrodes caused Peter's breasts to twitch. He was flabbergasted.
"No wonder my titties looked so big yesterday." he thought.
Reading his mind, Miss Tellit said, "Yes, Peter, this makes them grow.
Isn't it so exciting? Just think, soon you will have sissy titties all
of your very own!"
Peter just stared as the machine began to release the vacuum pressure
and his titties began to recede. When they had reduced about half way,
the suction again increased, seemingly pulling them even further out.
Miss Tellit broke Peter's tittie trance by saying, "Peter, I know it's
amazing, but we must turn to your makeup. Now, please do try to
She made up one side of his face and had Peter do the other. After three
tries, and a little touch up by Miss Tellit, he had it right - despite
the considerable distraction caused by the tittie machine, which
actually had become quite pleasurable to Peter.
"Good girl. Don't you just love your coral pink nails and lips?" Miss
Tellit exclaimed. Taking off his shower cap, she continued, "Now on to
your hair. Eugenia really did give you a wonderful cut and perm. Watch
how easily we can now manage you hair."
She showed Peter each step as his hair was very closely restored to the
salon-done barrette-held pageboy of the prior day.
Please with her work, Miss Tellit said, "Aren't you just the most
darling sissy on the face of the Earth! Now, let's get the tittie pumps
off and get you dressed for the day!"
His school uniform was exactly as the prior day's, but with one very
Miss Tellit showed him the proper way to don his white lace panties and
bra - making him try and try again until he could latch the bra behind
him perfectly. The satin and lace and tickled him in the most
distracting way, and he again marveled at how he filled out the bra's
The opaque sheer white knees socks with ruffled tops and satin bows were
next. Secretly Peter wished that he could wear full stockings attached
to garter like Miss Tellit. Black patent mary janes with one-inch heels
and pretty grosgrain ribbon bows on their toes quickly followed.
"Now, Peter, we have something new this morning that is to be part of
your regular uniform. As you may recall, Doctor D'Oley prescribed thorax
support. Well, your 'supporter' arrived late yesterday. Aren't you just
the lucky sissy!" she wickedly giggled, knowing full well what the
results would be for the poor hapless sissy.
Miss Tellit opened the bag she had carried in and produced at heavily
boned white satin garment. Peter knew instantly what it was - a corset!
Miss Tellit put the corset about his naturally slender waist and showed
Peter how to hook the metal clips in front.
Move over to the floor to ceiling mirror, Peter. Ah, perfect, now grab
hold of that bar hanging down from the ceiling. Yes, the one behind the
As Peter was stretched out she said, "Our goal for today is modest -
only three inches!" she exclaimed as she began tightening the laces at
Peter was amazed at how the garment drew his waist in. He actually saw
himself developing a more feminine figure. He also was having trouble
Eventually she quick tied the laces and said, "Now, let's check your
waist," said Miss Tellit as she pulled a cloth tape measure from one of
the vanity's drawers.
"Darn, only a little over two inches. We have more to go!"
Returning to the laces, she pulled anew, even putting her knee to
Peter's back. "Suck it in sweetie," she urged.
Peter could not suck anything in; he could barely breathe.
Miss Tellit again tied the corset off and re-measured.
"Excellent, three and a quarter inches! Let me finish off the ties and
then you can release the bar. Take shallow breaths. You will get used to
it in time. Now look at the results. See what a lovely girlie shape you
Despite his breathing difficulties, Peter was indeed very impressed. His
titties looked even larger and his hips had a more defined feminine
"See, it has places to attached garter suspenders," she teased, knowing
how fixated Peter was on stockings and garters. "Maybe when you are a
more grownup girl we can attach them to hold up some pretty stockings.
"Now, please put on your uniform."
Having trouble with the differently place buttons, Peter struggled into
his white, short sleeve, round collar polished cotton blouse. Because of
his new 'thorax support,' his charcoal shorts seemed easier to pull on.
He still had to struggle a bit with the side fastening of their tight
high waist. The elasticized silk gabardine fit about him like a panty
girdle until it flared out at his legs.
"Now put on your jewelry. It's over on your vanity, sweetie." Miss
Tellit instructed him.
Peter put on his girl's gold and pearl ring and added one pearl strand
under his round collar and another about his delicate, slim wrist. Last
was the gold and pearl anklet with its gold heart-shaped charm that had
'Sissy Prissy' written in bright pink enamel script on it, which,
because of the corset, required Miss Tellit's assistance. Everything
matched his new pearl ear studs.
Next was the starched white cotton and organza pinafore with its frilly
bib, tight waistline and petticoated short bottom.
Miss Tellit fussed with the organza bib straps that crisscrossed on his
back and the huge bow at his rear. Peter shamefully looked at the
embroidered cornflower blue script across its front that said 'Prissy is
"Well, sissy is as sissy does," he sighed to himself. "And life here is
definitely 'not' a box of chocolates. Well, maybe more like a boite of
Miss Tellit picked up on Peter's inner conflict and said, "Are we
troubled by how frilly we look this morning? Peter, you know what you
are, at least while you are here. We will discuss these and other
matters after breakfast."
"Peter, pick up your handbag and carefully check its contents for your
essential things. Failure to be properly dressed at all times will just
get you one of those troubling 'notations,' and being properly dressed
includes having your girlie essentials."
Peter checked it to find makeup, folding brush, hankie and the dreaded
P-Book all there.
"Remember to hold your handbag with limp wrist and only your thumb and
forefinger like a proper sissy. Now, under your desk you will find a
small messenger-type bag for your books and study materials. You see it
matches your handbag."
Peter picked it up and checked its contents as well - pad, pens, speech
training manual. Looking over the bag he noted that it was made from the
same white silk gabardine as his handbag and, like his pinafore, had
"Sissy Prissy" embroider on one side in cornflower blue. As if to
further drive home the point, this bag was trimmed in pink and blue
chains of frilly flowers.
Miss Tellit continued, "Put the strap over your head and then across
your chest. Be sure your name is facing out so everyone will know who
you are. And mind to not muss your hair.
"Good girl. Now I want you to go over to the large mirror and practice
your sissy pose," she added. "You might practice taking the book bag on
and off. It's trickier than you might think, especially while properly
holding your handbag and maintaining proper sissy deportment.
"Oh, when you enter the common room, there are book bag racks on your
left. Place your book bag there before entering the dining area."
Peter practiced before the mirror, slowly becoming transfixed at how
utterly girlie he appeared.
"Is there anything you have forgotten," asked Miss Tellit."
Peter, still fixated with the complete sissy image staring back at him
in the mirror, perfunctorily nodded 'no.' At the particular moment of
Miss Tellit's question he was enchanted by how his hair swayed over his
cute schoolgirl blouse collar.
"Excellent, then we're off. Peter, I shall eat with the staff and join
you after breakfast. You will find a seat with another student. They all
want to meet you! Smile and be gracious. However, be well advised that I
will keenly watch your deportment and manners.
"As a guidepost, remember this - if you feel as if your girlie
deportment is totally over-the-top, in reality it's probably just about
right. Anyway, there really is no such thing as a too girlie sissy
anyway, is there, my sweet?
"And Peter, you really are a quite spectacular sissy - more so than you
can even realize. Everyone will love you!"
"Oh, now 'that' really helps," thought Peter as they made their way
Miss Tellit, as planned, abandoned him at the entry way, again
mentioning that he should mind his girlie manners. Peter managed to
deposit his book bag in the rack in a semi-acceptable manner, composed
himself, and sallied forth.
Not unexpectedly, Peter was terrified as he crossed through the common
room and proceeded into the dining area. His progress did seem totally
over the top as his pinafore swished about him making a very distinct
rustling sound. Holding his handbag out with limp wrist and two fingers
was perhaps the most humiliating element. He was simply advertising what
a total pansy he had become.
Several students either nodded or said hello in the strangely stilted
voices dictated by the speech therapy program. A couple of younger girls
giggled before something, or someone, mysteriously silenced them.
Peter may have been mortified at the idea of mincing through public
rooms in his outrageous sissy outfit, but he was truly horrified of
being punished. He did manage a more than acceptable entrance - small,
mincing steps, hips swaying far more than he realized, arms in, wrists
limp, and smiles to everyone!
At the entrance to the dinning area he stopped and looked about. There
were about a dozen students and staff still eating. Only one table with
a lone pretty blond girl sitting at it appeared to have vacant seats.
Noticing Peter looking her way, the girl looked up and smiled at him.
"Well, here goes," Peter sighed to himself.
He minced over to be greeted with, "Good...mor...ning, sis...see,
plu...ease...sit...down," from her.
He nodded with a smile and managed to sit down as gracefully as his
frilly pinney and restrictive corset would allow. Peter emitted a small,
high pitched "eek" as the chair caused his little 'fanny friend' to
drive deeper into him, which caused the girl to stifle giggle behind her
upheld hand. Of course, Peter blushed anew.
"I...am...Win...nie...Too...good, she meticulously spoke out.
Peter noted that she was dressed in a similar uniform to his, but she
wore a short pleated charcoal schoolgirl's skirt. Her long blond hair
was pulled back in a ponytail. Her crystal blue eyes were stunning. He
figured her to be a year or two older than he.
Peter spotted some tablets of paper and a jar filled with pens in the
center of the table. He took the paper and pen and jotted down, 'Hi, I'm
Peter and new here.'
Winnie giggled, and wrote under his note, 'Of course U R new. No 1 could
miss such a perfect sissy! I am so happy you sat with me. U R sooo
pretty! I hope we can be friends!'
Although a little nonplussed by the obvious, but still stinging, sissy
reference, Peter nodded and smiled back as his food arrived. It was as
meager a meal as last night - whole grain cereal with blueberries and
"If they keep feeding me like this, I will lose the five pounds by
tomorrow," he thought. Then he considered how tight his corset was and
decided that maybe less food was a good call.
"Ah, what a lovely sight two pretty girls make," said Miss Tillet as she
approached Peter and Winnie carrying a coffee cup. Good morning, Winnie,
dear. How are you?"
Winnie stood to greet her, with Peter later stumbling up as well.
"Good...mor...ning, Miss...Tel...lit," she said. "I...am...well,
"I am well, thank you, my dear." Miss Tillet responded. "Oh, there's the
bell for morning class. Run along, sweetie, I have several things to
discuss with our new sissy."
After saying goodbye to Winnie and motioning for the two of them to sit
down, Miss Tillet took a sip of her coffee and began, "Okay Peter, this
is your first school day, and now I am now going to review our
objectives, methods and goals for the next month.
After we finish here, I will take you around the school so that you may
become better acquainted with the routine. Then you will join in a
truncated class mix. Tomorrow will be a regular Wednesday class day.
"I want you to listen carefully and take notes.
"It hardly takes a rocket scientist to realize that we are treating you
as a sissy. This is not an idle or capricious decision. I think you
realize at least one of the reasons why without further explanation.
"We will concentrate on three areas. One, your speech training; two,
your physical development; and three, achieving a better mutual
understanding of who and what you really are, or perhaps should be.
"Your speech training will be the regular regimen here at Merstead Hall.
It will start with basic vowel sounds, progress to forming syllables
with consonants, and then continue into whole words, phases and
sentences. We will ask you to use a higher register in your voice simply
because it fits into our plans. You simply must accept that.
"Your physical conditioning will have two objectives. Overall, we want
you to become better toned and more flexible. This will be done through
dance exercise. Specifically, you will develop a more fitting deportment
for a sissy. By necessity, basic deportment training will come first.
Again, at least for the next month, you simply must accept that as well.
The alternative, you will soon discover, is simply too painful.
"Lastly, we are going to immerse you into a sissy life. This is to allow
you to experience it fully. Peter, on one level you have been both
tormented and conflicted by your admittedly feminine appearance. This
conflict may well have caused, or at a minimum, exacerbated your
On another level you have found secret - well, only partially secret -
pleasures from it. For some time your mother has been aware of your
secret dressing, both in her clothes and your own, not-so-hidden stash.
However, she did not become fully aware of the extent of your dressing
until she contacted us and we placed surveillance video recorders about
"Now you are going to live out many of your dressing fantasies. We are
starting off with sissy clothes because they are a natural beginning
point. It is similar to dressing up a little girl to teach her
fundamentals of femininity. However, restrictive frilly sissy things
also impose certain elements of discipline that you will need whatever
the outcome of the next month may be.
"I don't want to respond to any of this right now. That is for your
little daily chats during the personal evaluation period. As I said, you
simply are to accept all these things as your life for the next month
and focus at the tasks at hand. Our rigorous discipline is to keep you
precisely focused - no more, no less."
Handing Peter a sheet of paper, she continued, "Now, let's look at your
"For week days you will see that Breakfast is served precisely at seven
o'clock. That does not mean either six fifty-nine or seven oh-one. From
eight o'clock to eleven you attend general group speech classes. At
eleven you have private speech drills that cover what you are learning
at the time. Lunch is at noon sharp. From one o'clock until two is
personal evaluation with the school psychologist, then back to speech
until four o'clock, and finally dance until five-thirty.
"You will bathe and dress for dinner at seven o'clock, study from eight
until nine and in bed with lights out promptly at ten o'clock. Starting
this evening, you will be wearing something more dressy to dinner, but
your uniform is required for the balance of the school day, except, of
"Wednesdays and Saturdays have the regular breakfast, speech class until
ten o'clock and dance until eleven-thirty. The afternoons will be
determined by the staff and me, as your tutor.
"Sundays have a late breakfast and are free - well, as 'free' as
directed by me. After class on Saturday your dress may vary, but it will
be consistent with your sissy persona.
"Oh, and Friday nights we do have to work off those nasty notations in
your little P-Book. I will give you instructions about that later.
"Now if you have any general questions, write them down on the pad
before you. If not, just nod your head."
Peter began scribbling madly on the paper before him and handed a sheet
from it to Miss Tellit.
"What happens at the end of the month?" he queried.
"Good question and one that will be discussed frequently with you as the
month progresses. However, in broad terms a decision as to your future
will be made. Your mother, but I doubt your father, will spend a weekend
here - or near here, at any rate. By that time, I dare say, you will
have a much better idea of just who and what you really are.
"And if you are wondering about the obvious, she does know about, and
approves of, your complete sissification. She will receive weekly
comprehensive reports as well as more frequent updates if necessary.
"Any further questions, sweetie?"
Peter, again somewhat befuddled, simply shook his head 'no.'
"Excellent, now for the tour. Please follow me and mind your deportment,
my dear. Oh, and leave your pinney on for now."
Walking back into the common room, they were encounter by the short
stout housekeeper, who appeared to be irritated.
"Miss Tellit, the sissy left her room in shambles." she announced.
"Oh, my, Hilda," said Miss Tellit, "I did ask her if she forgot
anything. I guess the poor dear was just too overwhelmed with all her
prissy sissy frills. Well, you know sissies and their pretty clothes! Do
you wish to make a 'notation' in her P-Book?"
Peter looked at Miss Tellit, his beautiful fairy princess, in total
disbelief at her transparent betrayal. Tears started to well in his
Hilda replied, "I most certainly do, and a strong one at that. You
should have seen the state her sleeping panties were in! Just
"Sissy, hand me your P-Book!"
With trembling hands and tears now in freefall, Peter fished into his
bag and handed her the horrid little red book. She took it and made at
least two notations.
"Trust me, sissy, come Friday you will feel everything I just wrote!"
she spat as she turned on her heel and departed. Peter was now softly
"Oh, now-now, Peter, learning can be so difficult at times," Miss Tellit
comforted. "It's only Tuesday, you best mind yourself for the balance of
the week or Friday evening will be most unpleasant!
"Now, gather yourself up. You need to repair your face."
After taking Peter to a nearby powder room and showing him how to do a
quick touch up, Miss Tellit led him to the main classroom. Before
entering, she said, "We'll sit in back and just observe for a while.
Starting tomorrow you will join the main class."
The class was interesting to Peter. The Headmistress, Doctor Learned,
was watching as individual students came before the class to recite
their current lessons.
Peter was simply awed by Lavinia Learned's presence. "Commanding," was
the word that came to his mind. She was over six feet tall in her spike
heels and regally turned out in her mid calf linen black pencil skirt
and crisply starched white cotton blouse. Her thick, full hair was a
silver color that almost appeared as platinum blond at first glance. It
was pulled up with a chignon about the nape of her neck. To Peter, her
piercing grey eyes seemed as if they could pierce six-inch armor plate.
Peter's heart jumped when she turned her back to the class to write
something on a chart. Above her black patent stiletto heels were full
fashion seamed stockings. She even wore an ankle bracelet with some sort
of charm on it, although Peter soberly doubted it was anything
resembling his anklet's charm.
Miss Tillet inwardly giggled at the sissy's predictable reaction and
then nudged him to leave. They proceeded about the ground floor of the
old estate. He was shown the soundproofed speech exercise rooms, common
areas and other rooms.
Peter loved the clicking of Miss Tellit's heels as she walked over the
hardwood and tile floors. He recalled making the same sound in his
mother's heels when he was left alone at home. He even once slept with a
pair of her heels next to his face.
Peter's attention to her heels did not go unnoticed by Miss Tellit.
"Wait until he gets a load of my heels this evening," she smiled to
Soon they went outside to an outer building that housed the dance
studio. Although he failed to fully appreciate it, Peter was looking at
a professional class facility. Mirrors were everywhere. Exercise rails
were attached to two walls and the hardwood floors gleamed like smooth,
Standing room, or stage, center was Madame Augusta d'Horscourt, Mistress
of Dance at Merstead.
She was another elegant slim woman of perhaps sixty with long white hair
done up in a ballerina's bun. Her eyes were a wonderful green color. She
was dressed in a flowing white mid calf ballerina's skirt over a white
"Well, here we have the new sissy!" she said. "Oh, Theo, she is a
beauty. I only hope she is as graceful as she is beautiful. You may pick
her up in and hour and a half, Theo.
"Sissy, we are going to spend the next few days just working on your
deportment. Next week you can put on your pretty tutu and join my corps
"Now, little one, put your bags on the table by the door and walk back
and forth from the table to the windows in your best sissy mince.
Continue doing it until I tell you to stop."
After putting his bag on the table, Peter began to parade back and forth
under Mistress d'Horscourt's watchful eyes. He made two trips back and
forth before she began prodding him to take smaller steps, sway his hips
and hold his arms in a proper sissy fashion.
After three more trips, she stopped Peter and said, "You must think
'prissy sissy', Peter. After all, it is who and what you are. Feel the
petticoats of your pinafore swish and sway as your walk. And I want you
to slow it down so that you may concentrate on each movement - much like
your speech training.
"Let's try it to music."
She went over and turned on an audio system. Soon the lilting tunes of
Swan Lake filled the room. "Good, now, little one, at half speed - back
and forth again," she commanded.
"Start slowly, and then follow the music, my little Odette! Feel the
music. Be my little sissy swan.
"Yes, you are getting it. A sissy can never be too delicate, too
effeminate, or too swishy. When you feel over-the-top, you are just
beginning to get it right. Exaggerated movement today will feel natural
After a seemingly endless number of repetitions, she said, "Now we will
work at your curtsey."
Madame d'Horscourt drilled Peter on the basics and then the finer points
of a proper curtsey for the next twenty minutes, which seemed an
eternity to the poor sissy. His little 'fanny friend' was particularly
distracting during the deep dips. Had it not been for his tight sissy
shorts, the 'friend' certainly would have been propelled from his
derriere. As it was, the dips caused it to slightly slide in and out in
a devilishly teasing manner.
At last, pleased with Peter's performance, she said. "Now, take a seat,
and I shall explain the next exercise."
Peter sunk into a straight chair at one side of the dance floor with
surprising grace. Every muscle in his body, and especially his feet, was
After a few minutes, Madame d'Horscourt said, "For the next exercise,
you will go out to the hallway, enter, mince, curtsey, mince, twirl, and
sit. Then rise, twirl again, mince curtsey again, and mince to the exit.
"You are about to have luncheon with the headmistress, and anything less
than a perfect performance may prove most troubling for you. Doctor
Learned demands perfection and will accept nothing less.
Peter did the routine until he thought he would collapse, but he did
learn to do it in an acceptable fashion.
"Peter, you have done well for today. Take a seat - in proper form, of
course, and rest for a bit. Then you must repair your face and
straighten out your pretty uniform and pinney.
"A word to the wise, my dear, never pass a mirror without checking your
appearance. When none is available, use the mirror in your powder
compact. This is your own responsibility, and do not let others rush
With a smile on her kindly face, Madame d'Horscourt continued, "I hear
you fell for the new girl trap of not making up your room this morning.
It was done to you, as with most new students, to make a point of
"This also applies to personal appearance. Perfection is of primary
importance - and hence, responsibility - to all students, and staff, at
Merstead Hall. This is especially true for sissies, for you have the
most demanding appearance of all.
"You have done well here today and should do well at lunch. You have
great natural grace, but we will talk more about that tomorrow. Now go
into the changing room and tend to your appearance. Do not, however, do
your lips. Come back here and I will show you how to repair yourself
after a meal."
Peter fixed himself up as best he could. Madame d'Horscourt made some
final adjustments and then instructed him on the fine art of polite face
and lipstick repair.
Miss Tellit returned just as Peter was finishing his last practice touch
"Hi, Augusta, how'd she do? I see you have been helping her in matters
other than dance."
"Indeed I have, Theo, just I did for you and many, many other girls,"
Madame d'Horscourt responded. "As to how she did, she actually was
brilliant. This one has very real potential. I dare say, that if she had
been trained from an earlier age, she could have become a first rate
"I see it's ten-to-twelve. You two best be one your way. It is not wise
to keep the headmistress waiting. Peter, mind what you have learned here
and you will do beautifully. I'll see you tomorrow."
Peter collected his book bag, straightened his pinney once again and
minced off behind Miss Tellit.
Entry to the common room and removal of his book bag was far easier this
time for Peter. Miss Tellit was on edge, herself. She had stopped twice
to inspect her appearance in mirror on the way to lunch, and her gait
had taken on more of a sissy-like mince.
However, far more concerned about his own performance, Peter barely took
notice of the subtle, but very real, change in Miss Tellit's demeanor.
At the entry to the dining area, Miss Tellit positioned Peter to her
left and instructed him to follow her movements. Side by side they
minced up to the far table where Lavonia Learned held court. Miss Tellit
gave the headmistress a little bob curtsey. Peter, following Madame
d'Horscourt's lesson, went into a deep, full curtsey, delicately bowing
his head and holding out the side hems of his pinafore.
"Well, I am impressed," the headmistress said. "For a sissy's first
school day that was a very presentable entry. Theodosia, dear, you look
as perfect as always. I love your heels. Girls, please have a seat."
They sat on either side of Doctor Learned. Miss Tellit sat with cat-like
grace. Peter managed a personal best as he lowered his petticoated rear
onto the chair - keeping his back ram-rod straight the entire time.
Lunch was immediately served. It was an excellent, if very small in
Peter's case, salade nicoise. He made sure that each bite was not larger
than a third of his fork, somewhat of a feat with the large red leaf
lettuce on his plate.
After a few bites, Doctor Learned asked Miss Tellit if she was pleased
with Peter's progress. The two of them chatted for a few minutes as if
Peter were not even at the table. Other than the few personal
pleasantries, they discussed Peter's situation in purely clinical terms.
Between his microscopic bites, Peter noticed a unique signet ring on the
headmistress' finger. Its emblem resembled an ancient crest.
As the conversation wound down, Doctor Learned asked if Peter's new
clothing had arrived.
"Many items, Ma'am," replied Miss Tellit. "I spent time while Peter was
in dance instruction to sort it out. She will have more than enough for
the next few days. I think you will be pleased with the one selected for
her introduction to the school this evening. More delivers are on their
"Excellent, Theodora." the headmistress replied. "And I expect some
direct shopping is planned?"
After Miss Tellit confirmed that several shopping trips were planned,
Doctor Learned turned to Peter and said, Prissy-Peter, please hand me
your P-Book. I wish to see what notations have been made thus far."
Peter initially panicked at the thought of more notations, but, with
great relief, took her at face value that see only wanted to look at it.
He fetched it from his handbag as gracefully as possible and handed it
"Only four notations so far, I see. That actually is not too terribly
bad. However, it only is Tuesday...
"Peter, you must understand that exacting discipline and complete
compliance with the program selected for each student here is an
absolute. And that absolute for you is that you are a sissy. You will
not act or play like a sissy, you will 'be' a sissy - twenty-four by
"There will be no deviation from this course for the next month. For
you, Prissy, that can either be quite pleasant, or horribly painful, but
comply you shall. I do hope you wisely choose the former and not
painfully choose the latter.
"Very well, I think we are concluded here, Theodora. Bring Prissy to my
office for her first voice work after her visit with Cordelia. You girls
Both Miss Tellit and Peter rose, curtsied and departed in matching sissy
gaits. Peter ran upstairs to remove his pinafore. After carefully
hanging it up, he checked his face, hair and uniform.
Looking at himself in the long mirror, it occurred to Peter that the
pinafore had given him a very different feeling with its frilly skirt
look. He missed it and felt somewhat uncomfortable in his shiny sissy
shorts that clung so tightly about his waist and hips. With his round
collar blouse, frilly knee socks and mary janes he knew that he
epitomized a sissy school boy - actually a very sissy school boy with
makeup, nail polish and long girl's hair.
His modest little titties in their frilly lace bra were clearly
noticeable under his blouse as he descended the stairs. It occurred to
him that, not only was he dressed as a sissy boy, but also he was being
deeply feminized. In addition to his titties, his clinched waist was
smaller than most girls and his derriere - with its little 'friend' was
puffed out in an almost obscene manner by the shorts.
After Peter retrieved his book bag, they walked to another part of the
old mansion to a door marked 'Cordelia C. Cutwell, Ph.D. - Chief
After knocking, they entered the oak paneled office. Doctor Cutwell
closed a large dossier marked 'P. Paunceworth,' rose to her feet from
behind a large mahogany partner's desk and said, "Good morning,
Theodosia, this must be Prissy Peter."
With the same slight bob-curtsey that she had given to the headmistress,
Miss Tellit replied, "Yes, Doctor Cutwell, indeed it is."
She was an elegant woman much in the mold of Lavinia Learned, but
perhaps ten years younger and with jet black hair and deep blue eyes. As
she came from behind her desk, Peter noticed she was wearing a similar
black long linen pencil skirt and tailored blouse, although Doctor
Cutwell's blouse was a pastel floral pattern made from fine silk with a
cravat style scarf tied at her neck.
The fact that she, like the headmistress, was wearing black patent
stilettos and seamed stockings hardly went unnoticed by the fetishistic
young sissy. She also wore a slim anklet with emblem charm about her
"Thank you, Theodosia; you may come back for her in an hour. Today we
are just going to get acquainted. I will do her baseline testing
tomorrow afternoon. Peter, please come over to the table by the window
so we may better chat."
Peter, taking the hint from Miss Tellit, felt compelled to give the
doctor a curtsey before mincing over to the table. He dainty sat in the
straight back chair, absently minding his non-existent petticoat.
After settling into her arm chair to Peter's left, Doctor Cutwell began.
"Peter, you may write down any comments on the tablet before you, but
today is going to be more of an orientation session and will not require
many responses, and most of those may be answered by a simple nod of
Peter noticed her hand exactly the same signet ring as Doctor Learned.
"Is this some sort secret sorority?" he pondered.
Doctor Cutwell noticed Peter studying her ring and commented, "Do you
like my ring, Peter?"
After Peter sheepishly nodded, she said, "It signifies membership in a
branch of a larger group that you may be introduced to someday, but that
is a long way from now. I do demand your complete attention, however
difficult that may be for a harebrained new sissy. I assure you that I
have ways of keeping your undivided attention if it flags again.
"Now, where was I? Oh, as Theodosia has told you, we have been studying
you for some time and advising your mother on various alternative
therapies for your condition.
"By the way, your mother is a remarkable woman. Doctor Learned and I
spent a lovely few days with her when she visited Merstead Hall a few
months ago. She both understood and appreciated our methods immediately.
In fact, this summer she is investigating some broader applications of
them with your father at a dear friend's Schloss in Switzerland. I dare
say that autumn shall bring many changes to the Paunceworth family.
"As to you, Peter, you are now into the alternative all parties thought
most appropriate for your condition. And there you shall remain for
thirty days. This had been decided, and you 'will' comply fully. I'm
sure that Doctor Learned mentioned the importance of discipline and
compliance when you took luncheon with her this noon.
"My role is really one of connecting the dots for you so that you
understand the brilliance and wisdom of the path selected for you.
Tomorrow I will conduct your first Sexual Preference Acuity Examination
that will, I'm sure, demonstrate many of these facts.
"Today, I want to cover only two things. The first is a review of how
you ended up at this institution and the second is to outline certain
"However, before we move forward, I must digress regarding my ground
rules. You 'will' be completely truthful with me, regardless of how
shameful or humiliating the subject. Prevarications will only earn you
some very painful notations in you P-Book, if not immediate punishment
from me on the spot. And that, my dear, is not an experience you will
"No answer is required here. The rules are simply what they are, and you
will follow them.
"You noticed the dossier on my desk; it is only part of a rather
thorough compendium about you. Cutting to the chase, Peter, you know
that how you are dressed in no accident. It may be shocking as to its
extent and abruptness, but as we all know, it certainly is 'not' a
random concept to you.
"First question, do you accept what I have just said?"
Peter's cheeks deeply blushed as he nodded his head in agreement.
"Excellent, you will find honesty is not only the best policy around
here. It is the 'only' policy!
"After reviewing Doctor D'Oley's report, this lifestyle may well be the
only suitable resolution of your unique characteristics. Frankly, Peter,
in many respects you came to us more female than male.
"Gender Identity Disorder, by itself, is a complex and powerful force.
One diagnostic criterion, if I may paraphrase from the DSM, is either
demonstrable evidence of persistent discomfort about one's assigned sex
or a sense of inappropriateness in the gender role of that sex. Peter,
your stammering may be a result of this painful conflict.
"However, when coupled with Congenital Adrenal Hyperplasia, it can be
devastating. Diana D'Oley's tests suggest you have CAH, which is a
medical term for impaired development of sexual characteristics.
Certainly your underdeveloped genitals and feminine breast support this
"In a less precise antiquated term that you may better understand, you
present medically as a near hermaphrodite - absent, of course, any
indication of full or partial female genitalia formation.
"Coupled together, these may well be the cause of your stammering. This
is what we shall explore over the next month. Time will tell.
"On those points, I have another question. Does being dressed in pretty
frilly things cause a form of peace for you? By 'peace,' I mean
serenity, not a sexual or fetishistic charge - we all know you get
Peter honestly thought for a few moments. It certainly did have a huge
sexual element. His peenie was stressfully erect most of the time now,
but was he happier?
Finally, he looked at Doctor Cutwell and slowly nodded his head 'yes.'
"Good girl," she continued, "personal awareness is always the first
positive step. Now, for another question, and this will require a
written response. What were you dreaming about this morning when you
ejaculated into your panties?"
Peter's entire body tensed. He was open to admitting that he loved being
dressed in the sissiest of sissy frocks, but kissing the other sissy boy
was so shameful.
His hand trembled as he took up the pen to write on the paper tablet.
Cordelia Cutwell read the signs perfectly and said, "Peter, first tell
me the part you are not ashamed of."
A relieved Peter scribbled down the fact that he loved being dressed in
frilly things, completely missing the Doctor's use of the word 'first.'
"Excellent, Peter, but we all know that you are a hopeless sissy with a
severe clothing fetish, don't we, my dear? Now, either hand me your P-
Book, or tell me what shameful thing drove you over the edge.
Tears began to flow from the young sissy's face. How could he admit such
a 'faggy' act? He also wondered just how much she knew about his past.
Doctor Cutwell interrupted his dilemma, "As this is your first session,
allow me help you a bit here because your sissy tears will not sway me
in the slightest. Peter, accept the fact that you are a sissy, plain and
simple. As we progress with our sessions I will demonstrate that simple
fact to you in many ways. But for this moment, just accept it.
"Now, sissies have special little fantasies, sometimes with other
people. It is normal for you, and we all expect it. Did your dream
involve another person?"
Tears still flowing, Peter nodded.
"Peter, I actually expected that. Now please tell me with whom."
With shaking pen, Peter wrote, 'Another pretty sissy boy. We were
Cordelia Cutwell actually was mildly shocked. She had expected the other
party would be Theo Tellit - not that she was far from his fantasy.
"This one is further along than we thought," she noted.
"Very good Peter, kissing another boy as beautiful and you would be a
delight for any sissy. You will come to realize that sissies really are
not men, so kissing another pretty sissy boy really is not a naughty
"Be glad, very glad, that you were a good girl and told me the truth.
The alternative would have been most unpleasant, and now you are on your
way to self discovery.
"Now, on to your assignment," she said as she handed Peter a pink silk
cover journal book. It came as no shock to Peter to notice the front had
'Prissy's Journal of Self Discovery' written on it in pretty white
"Each evening you will make two entries in your journal. One will be in
response to a homework question I, or others, assign. The second shall
be your observations from the day. This journal will become your
personal analytical biography.
"Your assignment for tonight is to write about one or two sissy-like
experiences you had before you came here. For example, wearing you
mother's things, interaction with other children, or what special outfit
you liked growing up. As to you daily observations, you may pick
anything that happened to you during the day. In the common room you
will find my mailbox. Please deposit the journal in it each morning on
your way to breakfast.
"You have a few minutes before Theodosia returns. Please sit here and
reflect on your entries for today. I will complete my session notes at
Peter stared at the open book and started recalling the many sissy
things he had done. There were far more than he had ever realized - and
some really were quite shameful.
Miss Tellit entered after knocking on the door and again curtsied to the
"She did very well, Theodosia." Doctor Cutwell said. "Please take her to
her next appointment. I look forward to reading her journal entries for
With another curtsey, Peter departed in Miss Tellit's wake as they
proceeded to the headmistress' office. The name on the door, 'Lavinia B.
Learned, Ph.D. – Headmistress,' was in the same gold lettering as Doctor
Cutwell's. They entered an outer office to be greeted by Doctor Learned
personal assistant, who turned out to be none other that Winifred
Toogood, who greeted the new arrivals with a broad smile and a
After typing something in her workstation, she parsed out syllabic
permission for Miss Tellit and Peter to enter the inner sanctum.
Doctor Learned's office was even more imposing than Doctor Cutwell's.
Off to one side was a grouping of three high stools that faced a mirror
and a chart. One stool was set up with a recording device.
As at lunch, Miss Tellit and Peter minced forward and curtsied.
"Ah, now we begin Prissy-Peter's voice training. Theodosia, please set
her up on the recording stool. I shall be with you momentarily," the
After Peter was comfortably perched on the stool most directly facing
the mirror and chart, Doctor Learned moved next to him and said,
"Prissy-Peter, we shall now teach you the basic vowel sounds. This will
serve as your exercise base to achieve two things: one, proper non-
stammering diction and, two, an appropriate register and pitch for a
For the next ninety minute the two women drilled first the long and
short vowel sounds and later an elevated pitch in Peter's voice. Time
after time they played back recordings and corrected him, often putting
their hands to his voice box to encourage a better modulated high
register sound. By then end of the session Peter was singing out vowels
sounds like a sweet little sissy bird.
Doctor Learned handed Peter a small plastic card with the phonic vowels
sounds printed on it, and said, "You will drill on this every day for
the next week. I will conduct group practice Thursday, and I expect
great improvement. In any of the practice rooms you will find recording
equipment to help you along."
After pressing a button on her desk summoning her assistant, she
continued, "That will suffice for today. Winnie, dear, it's such a
lovely day, please take Prissy-Peter outside and teach her the basics of
sign language. I wish to discuss some matters with Miss Tellit."
Prior to exiting, both Peter and Winnie turned to give the headmistress
their very best deep curtsey - Peter's being surprisingly similar to the
more experienced Winnie's.
Winnie led Peter out to a picnic table on the side lawn where she
drilled him for over an hour on the rudimentary signing of letters to
spell words. It was very basic, but it would allow Peter to at least
communicate on a limited basis before he was allowed to speak again.
Peter could not fail to appreciate how very pretty Winnie was. Not only
that, but she was wearing stockings, and Peter found himself again
trying to mentally will her skirt up so he could see what lingerie
treasures lay beneath. However, Karnack the Magnificent he was not.
Eventually Miss Tellit appeared and asked Winnie to take Peter to his
room and help him undo his 'thorax support,' which she eagerly accepted.
Turning to Peter, Miss Tellit said, "The Headmistress has decided that
you shall now be addressed as 'Prissy-Peter' from now on. None of us
really think that 'Peter' alone is terribly appropriate for such an
"Actually, we are all sure that you will soon be begging us to drop your
'Peter' entirely. In your case, it sounds almost as ridiculous as
calling you Dick!" she giggled. "Do you fancy 'Priscilla'? I think it's
a lovely name, and so much more appropriate.
"Anyway, now be off. I shall join you in a bit. Oh, and, Winnie, please
supervise removing Prissy-Peter's makeup and putting her hair up for her
bath. She also is scheduled for a breast pump, perhaps you would like to
see to that as well. She needs a full half hour. The devices are preset
to the proper settings. Just switch it on."
Peter was mortified. It was bad enough having Miss Tellit feminize him,
but Winnie was more of a peer. Then the thought of having her discover
the pathetic size of his peenie hit him and he started to withdraw
backwards from the two women.
"Prissy!" Miss Tellit snapped, "one scintilla of resistance from you,
and I shall spank you right here and now - and then refer the entire
matter to Doctor Learned."
A few tears welled in Peter's eyes as he accepted yet another defeat.
The idea of being taken over Miss Tellit's knee was strangely erotic to
him, but the thought of being dragged before the headmistress was
Winifred Toogood, however, was delighted beyond belief!
"Come...a...long...sis...see...boy," she commanded.
A meek and weepy Peter followed her to his room like a pouting puppy.
Once in his room, Winnie helped him out of his shorts and blouse and
then turned to inspect her new toy.
"Oh my God," she thought. "He's almost too girlie to even be a sissy!
Look at his boobies. They have to be at least an 'A' cup. Gosh, I
thought it was padding, but it's real! And, oh my God, that tiny thingy
in his panties!"
Peter stood before her red faced and weeping, realizing she was giving
him a thorough appraisal. Despite the intense humiliation, his peenie
was beginning to stir - and that would cause him even greater
Winnie was having a similar reaction as she felt her own panties dampen.
"This summer just got a whole lot better!" she smiled to herself.
"Pris..see...turn...so...I...can...un...lace," she said.
Remarking to herself that Peter may indeed have a slimmer waist than
her, she made quick work of undoing the corset and then motioned to
Peter's feet, saying, "Take...off...shoes...and...hose."
As Peter complied, she fetched his mules and a white silk kimono robe
from his closet for him to wear. She placed the mules at Peter's feet
and motioned for him to put them on. Winnie hung the robe in the
Winnie turned Peter around so they were facing one-another, and said,
As Peter once again mindlessly complied, she reached up and touched the
lace of his bra, prodding and testing the flesh that was underneath.
"Un...hook...bra," she next ordered.
Peter reached in back and effortlessly released the hooks, thanks to
both years of playing with his mother's lingerie and the practice from
Winnie slowly moved his shoulder straps off his shoulders and lowered
the bra. "Love...lee...tit...tees, sis...see!" she exclaimed as she
gently fondled them - much to Peter's distress. Mentally he was deeply
humiliated, but physically the erotic sensation caused his peenie to
actually throb. Neither reaction escaped the young woman's attention.
"I just have to see it. I cannot believe anything can be that small,"
she thought as her hand went down to Peter's lacy panties.
"Oh my God, even hard it's tiny," she exclaimed to herself.
"Sooo...small...a...pee...nee, but...a...nice...size...clitty!" she
Peter wanted to melt between the floorboards. This was the worst
humiliation yet to the hapless sissy. However, all three inches of his
pathetic sissy-pole remained urgently hard!
Realizing that she might exceed her privileges, Winnie ordered Peter to
sit down to receive his tittie treatment. She helped him attach the
breasts stimulators and pumps, instructing him how to do it himself the
next time. Once the machines were gently performing their magic, she
began showing Peter how to put his hair up in the shower cap and
properly remove his makeup and cleanse his face and newly pierced ears.
Winnie did, however, stretch her privileges a little more by making sure
that Peter got more than one glance up her skirt. It amused her to no
end to watch the sissy react to her stocking tops and garters.
"Sissies are sooo easy," she chuckled to herself.
Just as they were finishing up, and fortunately for Winnie, when her
short pleated skirt was in its proper place, Miss Tellit arrived.
Peter was surprised by Miss Tellit's appearance. It was so different.
Despite the early summer month, she was wearing a black leather
miniskirt with sheer white stockings. Black leather was one of Peter's
darkest fetish-fantasies. So overwhelming was the skirt, he only noted
that her blouse was crisply white and that her heels were shiny black
and very high.
"Excellent, our sissy seems ready. How much longer on the pumps?" she
Winnie held up three fingers. Miss Tellit smiled in approval and asked
Winnie to draw Peter's bath.
After checking Peter's progress and smiling again, she waited the
remaining couple of minutes. Her calculated closeness and leaning over
allowed Peter to glance at her blouse. It was crisp white polished
cotton with a large notched collar.
When she leaned forward he could see her white lace bra, and, after
having to catch his breath, noted that it only covered the bottom third
of her breast. Faint impressions of her nipples could actually be seen
through her blouse.
After the prescribed time was up, she removed the instruments, and told
Peter to go to the bathroom to remove his 'fanny friend,' douche, and
Peter gratefully retreated to the bathroom as he feared his sensory
overload might soon explode if he remained with Miss Tellit any longer.
While Peter was in his bubbly lilac scented tub he heard giggles coming
from the other room. Perking his ears, all that could catch were a few
phrases such as: "It...is...just...sooo...tiny," and "Oh my God, Winnie,
the sissy will adore this too!"
Clearly they were laying out his outfit for the evening...not to mention
the 'other' things they were discussing. Peter wanted to disappear down
the drain of the tub.
Miss Tellit poked her still grinning, and almost giggling, head in the
door and said, "Prissy, dry off, use your special lotions, powder up and
come out here. We are going to play sissy dress up this evening. You'll
Peter slipped on his mules and kimono and returned to his bedroom. He
was relieved that, at last, Winnie was leaving.
"Oh, Prissy-Peter, we have such a lovely outfit for you this evening.
Everyone will love you in it!" Miss Tellit gushed. "See the pretty pink
bra and panties on the bed. Aren't they lovely! Please put them on. They
have some very special features. Never mind the adorable negligee. It's
for later. Well, that is 'later,' if you are a very well behaved sissy."
Peter went over to the bed and picked up the lingerie. Never had he even
dreamed of such things! They were made from fine double-faced pink
satin. Peter was curious, though, about the small slit on the panties'
rear. He thought it might be a split seam, until he noticed that the
edges were carefully finished off with tiny piping.
"Oh my God," thought Peter as he began to tremble at the thought of
wearing them. Never had he seen such erotic panties!
The panties had more ruffles and white lace than Peter could ever have
dared imagine. Bows were everywhere. They slid up his smooth legs to
tightly fit about his waist. The leg holes were cut high on his thighs
and pulled the slippery satin over his derriere and front. There seemed
to be a bulge of fabric over his peenie.
Peter turned to the bra, which perfectly matched the panties, right down
to little openings - this time at his nipples. He lifted the bra over
his arms and up to his shoulders. As he moved to attach the rear hooks,
its flesh-forming shape fit and shaped his breasts just like his other
However, not only were his nipples were fully exposed through opening at
the tip of each cup, but they were complimented by trimming similar to
that on his panties. His nipples were surrounded and displayed by a ring
of frills and lace.
However, Peter's excellent sensory experience was only beginning.
"Peter," Miss Tellit said as she opened a new package of white opaque
hosiery. "Tonight you will wear something new - thigh high stay-up sissy
stockings with frilly tops. Aren't they 'to die for?' You may sit down
and pull them up. The pretty white satin bows face your rear.
"Mind that you don't ladder them, but then you 'HAVE' had practice
wearing your Mummy's stockings, haven't you, sweetie? When you fully
accept yourself as a fully petticoated sissy - and nothing but that, we
will allow you to wear your beloved garters. Frilly garter belts and
suspenders are for real sissy girls, not panty boy sissies in shorts."
"Good, don't you just love them? Now attach your cute little 'Prissy
Sissy' anklet and slip back into your mules. Then come over to the
When he arrived at the dressing vanity Miss Tellit was seated at its
small frilly bench. She had him remain standing while she reached into
the front of his panties.
"Peter, these panties have a very special feature - a little peenie
pouch. Just what every sissy dreams of!"
She maneuvered the bulge Peter had felt so that it covered his peenie in
a double sided satin bag, cinching its base tightly at the base of his
peenie and tessies.
If playing with his peenie was not enough, Miss Tellit devilishly let
her skirt rise up to display her stocking tops and white garter belt
suspenders to the tormented sissy. This time Peter fully appreciated her
black patent five inch pointed toe stiletto heels. Part of him wanted to
go to his knees and tenderly kiss the treasured erotic objects.
"Doesn't that feel just divine?" she cooed. "Now have a seat, I have
As Peter sat down he discovered just what the little pocket did. With
his every movement, the pouch caressed his tiny little pole causing a
sensual jolt to go through his entire body. He greatly feared that he
would never make it through dinner - let alone the entire evening -
Miss Tellit fully appreciated what the poor sissy was experiencing, and
continued to pile it on. "Now, sweetie, we are going to use a different
type of pump tonight. It's for your nipples."
She took two small cylinders and attached them to the breast pump's
hoses and told Peter to hold one over each of his nipples. Their
openings barely covered his areolae. When Miss Tellit turned on the
suction his nipples were pulled almost a full inch into the tube. Unlike
the full breast cones, the suction did not fluctuate. It was constant
and demanding, almost painful at first.
After a minute, she turned off the suction and had Peter reposition the
tubes. Turning the machine back on, Peter was aghast at the bizarre
distention it caused. It was even more pronounced this time.
Peter could not help to question the permanent effect the severe suction
would have. So much of what was happening to him seemed like it would
never be reversed. Whatever sliver of masculinity he even had was being
literally sucked from his body, not to mention his psyche.
Pleased with the tube's placement, Miss Tellit said, "Peter, you will
get used to the pull of the machine, and you will adore how sensitive it
makes your nipples. This treatment will now be part of your daily
"Now, we must turn to your makeup and hair. As tonight is a dress-up
evening and you are to be formally introduced to the school at dinner,
it will be more dramatic. I also want to do something a little different
with your hair. I want you to carefully observe the differences from
your more sedate daytime appearance."
For the next twenty minutes Miss Tellit fussed about Peter. When she was
done his eyes, they did indeed have a more pronounced, doe-eyed look
with much more liner, mascara and shadow than usual. Although still
coral pink, his lips had an extra gloss and penciled-in pink highlights.
His cheeks also had extra blush, giving him a slightly comical, but
very, very sissy look.
Miss Tellit used mousse and a curling iron to add extra bouncy curls to
his hair. At his left side part, where the plain uniform barrette
normally went, she placed a quite large pink taffeta bow mounted on a
She then removed Peter's nipple pumps. Peter was horrified at how
distended his nipples remained after the appliances were removed.
"Oh Prissy, you look so adorable! Look at how long and divine your
nipples are. True sissies all have huge nipples. They become a source of
great pride and pleasure to you girlie-boys.
"When I put you to bed I just might give you a little taste of that
wonderful sensation. That, of course, is only if you are a very, very
good sissy this evening.
"I think you look so cute, we just have to give you a sweet sissy scent.
Then you get to wear your first formal sissy outfit - and part of it
will be your very special treat. Aren't you just the lucky sissy
Peter was still dumbfounded by his nipples as she sprayed the most
flowery perfume about his neck, wrists and over his panties. Peter quite
liked the scent, not realizing - sissy that he was - that it was far too
Walking back from his closet with the most frilly confection Peter had
even seen, Miss Tillet effervescently said, "Now, Prissy, this outfit is
so 'YOU.' Come over to the bed and kick off you mules so we can get it
on you. An outfit this frilly belongs on only the prettiest of sissies.
And tonight, Prissy, you are just that!"
Peter could not take his eyes of the outfit. It was made from shiny
sheer pink taffeta with pink and white ruffles, lace and bows
everywhere. He was about to be dressed in the most frilly sissy outfit
in the world - at least 'the world' as Peter knew it at that time. His
tiny teapot, already in a considerable state of 'distress' in its
torturous pouch, almost lost its load right then and there.
Miss Tellit went behind Peter and held out the back buttoning top so
that he could slip his arms into it. Peter had tremors about his arms
and chest as the delicate fabric shimmered over him. As Miss Tellit did
up the many small cloth covered buttons the fabric closed over and
caressed his chest. The feeling across his elongated sensitive nipples
was a near epiphany for the poor sissy.
The sensory onslaught continued as she raised his shorts up his legs and
fitted them about his narrow waist. They had matching buttons up his
back that started below his derriere and continued up to the high, broad
"I think these small sweet back buttons just so define a sissy, don't
you Peter?" she teased. "Now, let's go over to the long mirror and I
will finish you off.
She positioned Peter so he could observe every detail as she proceeded
to take up satin ribbons that threaded through the bottom hem of each
pant leg and short sleeve. She pulled each ribbon tight and tied it off
at each side with a large fancy bow, allowing the ends to trail down his
legs and arms. The effect was to cause Peter's short pant legs and
sleeves to balloon out. She knew the puffiness would cause the taffeta
to make a very noticeable swishing sound as the sissy moved about.
Lastly she took two broad taffeta reinforced bands that were attached to
the rear of his high collar and tied them into a huge bow at the right
front of his neck, just opposite of his matching hair bow. Pleased with
the bow, she added his pearl necklace.
Miss Tellit handed Peter a pair of lace gloves and told him to slip his
long slender hands into them and then add his pearl bracelet. The gloves
had a broad delicate lace ruffle just above his slim wrists.
"Now, Prissy, it's time for your surprise," she said as she retrieved a
shoe box from the closet. Handing Peter the box, she continued, "Prissy-
Peter, open the box and put them on. They are your next step to full
Ignoring her reference to his ever-progressing emasculation, Peter
fixated on the box, knowing it contained shoe, but dreaming of higher
heels and slender shaped toes.
His dream came true - actually, better than true, and Peter could not
even disguise it from the greatly amused Miss Tellit.
With a shaking hand he took out one pump. It had a delicate four inch
heel and was made from pink satin that matched his outfit. The best part
was the huge pink satin bow on the toe.
As he brought it to his face to reflexively kiss it, Miss Tellit, said,
"Prissy, don't you dare get lipstick on your pretty new pump! However,
being that you adore kissing women's shoes so much, I will allow you to
kiss one of mine when you are finished dressing. Now, be a good sissy
and put them on."
As Peter sat on the vanity stool and slipped on the magnificent heels he
discovered that the taffeta of his frilly top rubbing against his
swollen sensitive nipples cause as much, if not more, distress as did
his peenie pouch. Taken together with his new high heels and longer
stockings, the boy was fast approaching a train wreck.
"Isn't it just so divine being a pampered frilly prissy sissy?
"Prissy-Peter, you 'know' it is so 'you'!" Miss Tellit remarked, driving
the nail in a little deeper.
"Now, let's get you into your special dressy pinafore and take some
pretty pictures for your mummy. Sweetie, come over to mirror and admire
Peter was mesmerized by the image looking back at him as Miss Tellit
slipped the sheer organza pinney over his shoulders and tied it in back
with the biggest bow yet.
"Here, Prissy, take your new bag and hold the pink chiffon hankie in
your other hand and strike your very best limp wristed sissy pose."
Peter needed no urging what-so-ever. He was somewhere in outer space
with his eyes traveling up and down his body, taking in every tiny
His light brown pageboy fell over the chin-high ruffled top of his tight
collar. The twin bows, one in his hair and the other on his collar
sparkled. The frilly transparent bib of his pinney allowed his distended
nipples to point outward in their silk traps. Its broad frilly shoulder
straps emphasized the puffiness of the short sleeves.
Given everything else, the 'Prissy Peter' embroidered on the left side
of the pinney's bib seemed almost normal. He wondered where all the talk
of changing his name to Priscilla would lead - secretly fully aware of
the answer, but failing to acknowledge it.
The short skirt portion of the pinafore flared out and ended with a
several rows of ruffles and lace just above the bottom bows on his pant
legs. Despite the fluffiness of its petti-type skirt, the apron allowed
him to see through to the outline of his very stiff peenie in its silken
Two of his long, thin, coral painted finger held the ribbon of a tiny
pink taffeta pouch bag in one hand and a delicate pink hankie in the
Returning to his sweet heels, Peter actually began to swoon. They looked
divine to him, especially with his mid-thigh white stockings with their
ruffled tops. He even turned to look at the bows behind them, which
looked divine with the huge organza pinney bow.
Oblivious to Peter, Miss Tellit had been snapping away with her camera
the whole time. She had planned on having him move about in his
swishiest manner, but Peter was now doing it all by himself. The sissy
was simply in a rapture all of his own. She made a note to discuss this
"Time to bring him back down to planet Earth," she thought.
"Prissy, one last thing," Miss Tellit said as she rose one of her heels
a few inches off the floor, allowing her leather skirt to rise over her
stocking top. "I want you to show respect for your mistress by placing a
perfect lipstick kiss mark on my toe. Then everyone at dinner will know
just what an obedient little sissy you have become - won't they,
Her shiny black spike heel focused Peter's attention. He dutifully knelt
and placed the mark of worship and submission on his mistress' foot.
"There now, wasn't that fun? Prissy, you are such a shoe fetishist.
Well, babycakes, you've arrived at just the right place for that, I can
assure you. Now, go over and fix your lips and pack up your handbag.
"And Prissy-Peter, you had better live fully up to your 'prissy' name.
You 'will' swish about exactly as you look - total over-the-top prissy
sissy. No gesture can be too swishy or effeminate.
Also, in case you haven't noticed it, when you move, you sound it. So
just 'be' it!
"How does that tacky Army ad go? 'Be all the sissy your can be?' That's
you tonight, babycakes!
"Anything less will embarrass me, and that, sweet cheeks, is definitely
'not' in your best interest. The slightest transgression will result in
a severe notation in your P-Book. And you do not want even to think
about a major transgression.
"However, proper behavior does have its rewards, and I have a very sweet
treat planned for you later this evening.
As they walked out, Peter did notice that the puffed out taffeta in his
pants and sleeves made a loud swishing sound. His every movement caused
it to occur. The befuddled sissy could no more escape the sound than the
manner in which he was dressed.
Going down the stairs caused even greater distress and torment to his
imprisoned peenie and exposed nipples.
"My God," Peter thought, "there simply is no escape from this!"
But then, did he really want it to end?
However, there was no end in sight, and it was about to get worse. Miss
Tellit led Peter through the common room, stopping to chat with students
and staff. Each time she made a point of not only presenting the finer
points of Peter's humiliating attire, but also pointing out the
perfectly formed lip marks on the toe of her sexy pump.
Peter did, almost by rote, uphold his end of the bargain. He minced, he
swished, and from every pore in his body he oozed pure prissy sissy.
Peter noticed that more than one student looked at Miss Tellit with
longing eyes. He also saw the elegant Doctors Learned and Cutwell off in
one corner carefully observing the proceedings.
Dinner eventually came and found Peter sitting at a table with the two
Doctors, Miss Tellit and Winnie. Miss Tellit was seated to the left of
Cordelia Cutwell, and Winnie to the right of Lavinia Learned. Peter
resided somewhat apart at the opposite side of table, seemingly the
object of their attention. Well, actually, the object of the entire
Poor Pete could barely eat because of his concerns about deportment and
his utterly humiliating appearance - made worse in Peter's muddled mind
by the fact that he loved how he looked.
Dinner did finish to Peter's great relief. However, it was a respite
short lived. Doctor Learned rose to her feet as Doctor Cutwell clinked
the side of her glass with a knife.
The Headmistress said, "Faculty, staff and students, I wish to present
our newest sissy student. You all have seen her mincing about. Now,
please welcome her to our student body. I give you Prissy-Peter!"
"Stand, twirl about as Madame d'Horscourt taught you and then give a
curtsey in each direction. I expect at least three of them - with cute
little sissy twirls between each curtsey!" Miss Tellit ordered.
Given the assemblage of raw female power, Peter simply rose and meekly,
but also perfectly, complied. The 'crowd' loved it and applauded his
each and every curtsey, often calling out what a perfect sissy he was.
Eventually it did end, and Peter was allowed to return to his bedroom.
Once there, Peter removed his pinafore and carefully hung it up in the
closet. He then sat down at the small ladies writing desk and opened his
pink journal as he contemplated Doctor Cutwell's two assignment
Peter was shocked at how easily his past experiences came to him,
including a couple shamefully naughty ones in particular. However, those
could wait for another day. Tonight, he decided, he would write about
that special childhood outfit he loved so much. It was in many ways like
He had loved wearing it until other children began teasing him too much.
He secretly cried for a week after his mother took it away. Shortly
thereafter, Peter began 'sampling' things from his mother's lingerie
The words flew off his pen, especially when he described the lovely
silky blue blouse and shorts he so adored.
Turning to the events of today, he first thought of how Winnie had
flirted with him earlier - well, at least the non-humiliating part of
it, but decided that might get both of them in trouble. Thinking back to
his first entry, he walked over to the long mirror to again inspect what
he was wearing. It was so much better than his old beloved blue shorts
He posed and twisted before the mirror as he assumed every over the top
limp wristed sissy movement he could imagine. Realizing that he well
might squirt in his panties, he reluctantly withdrew to complete his
journal, which would detail how much he liked the pretty pink sissy
outfit he was wearing in far more embarrassing detail than Peter ever
could have imagined admitting only thirty-six hours ago.
As Peter set his pen aside and closed his journal, his mind turned to
Miss Tellit. He wondered what delight she had planned for him this
evening as his mind bounced back and forth between her black leather
skirt, stiletto heels and memories of suckling her breast the prior
Thinking about her heels caused him to gaze once again at his beautiful
pumps. He was thus as she walked through the door. Peter immediately
noticed that her makeup seemed more striking, making her appear a little
older and a lot more assertive.
"Prissy have you completed your homework?" she asked. Seeing Peter nod
his head, she continued, "Very well, time to get you ready for bed and,
of course, your little treat. You must be a wreck after wearing all
these fancy, frilly things - not the mention those beautiful heels!
Everybody thinks you are the best sissy boy the school has ever had!
"Now stand up so I may unbutton your blouse and sissy shorts. Then we
must tend to your face. For now, I am going to allow you keep your heels
and stockings on. I think they will make your little reward that much
She removed Peter's top and shorts, leaving his pearl necklace in place,
and had him don the pretty short pink negligee that matched his bra and
panties. Moving to his vanity, Peter removed his gloves and bracelet and
cleansed his face before proceeding to the loo to brush his teeth and
take his pills.
He gave himself a final once-over. The bow was gone from his hair and it
gently fell over one eye in what Peter considered a very sexy manner.
His nipples were less distended, but remained very sensitive. Just
touching them caused all sorts of strange feeling to cascade about his
frail body. He could feel that he peenie pouch was quite damp. Its
torments over the past couple of hours had caused his tiny peanuts to
ache as never before. However, most of all he adored his sexy new heels
and wished that his little ensemble included a matching frilly garter
Peter's little moment was halted when Miss Tellit said, "Prissy, stop
admiring yourself and get in here."
Peter minced in to find Miss Tellit sitting on the side of his bed. Her
blouse was open to her waist, showing the edges of her bra. Her legs
were crossed and her skirt was practically up to her hips, fully
revealing her stockings and garters.
"Now, my little high heel fetishist, come worship you mistress's shoes.
Peter didn't need to be asked twice. He was on his knees in a flash,
caressing one and then the other heel with his hands and gently brushing
his lips against the cool slick shiny leather. His kiss mark from before
dinner remained fully intact. For reasons he could not possible fathom
at the time, he took great pride in it being there.
Miss Tellit kept encouraging him on by softly moaning and telling him
that he was where every sissy belonged - respectfully at her mistress'
Thinking it time to move on and worrying that the hapless sissy might
lose it merely by kissing her heels, Miss Tellit stood up and said,
"Prissy Pricilla, it is time for your real treat. Lie down in the center
of the bed on your back."
As Peter complied, she went over to the nightstand and took out four
long, reinforced lengths of white satin ribbon.
Looking over the supine Peter, she allowed him to get more than an
eyeful of her quarter bra and exposed hard nipples. She quietly ordered,
"Be my good little sissy and spread your arms and legs out. I am going
to tie them to the bed posts.
Despite knowing Peter was totally under her spell, she diverted his
attention by treating him to extra up-skirt and open blouse views to
insure his mindlessly compliance as she wove her bondage web. With
amazing speed she deftly bound each of his limbs to the nearest post,
finishing each with a pretty bow just beyond his reach.
"Another sweet satin prison for my young sissy," she cooed. "And the
real fun has yet to begin!"
Miss Tellit smiled as Peter lightly struggled in his spread eagle
bondage. She knew he was turned on by it. She knew that she certainly
was - as her thoughts briefly drifted off to Friday evening.
"Egad," she thought, "this one will be transitioned before the first
week is done." In a small way she wished he would resist more. "Well,
tomorrow we will just kick things up a notch!"
Again leaning over his face, she pulled her blouse back to fully display
her breasts. "Don't you love my breasts, Prissy Priscilla?" Moving her
hands to cup her breasts, she continued, "See how beautifully they fit
into this special bra."
Noticing that Peter was quite literally drooling, she pressed on, "Yes,
I can see how much you like them. But the question is do you want to
have titties just like them? I know you want them. Now I'm going to show
you how much pleasure they can bring."
She moved her head down to Peter's exposed nipples and gently blew on
"Yes, Priscilla, they are so sensitive...so nice," she whispered to him
as she placed her mouth over one of his nipples.
As she began to lick and gently suck the nipple, a pleasure the likes of
which Peter he had never dreamed of overcame him. He moaned in near
She switched nipples and pushed Peter even further down his orgasmic
After a few minutes of pleasuring his engorged nipples, she leaned over
to the nightstand and took out a latex glove and lubricant. Peter felt
the stimulation stop, but before he took any notice of why, Miss Tellit
was once again laying beside him sucking on his nearest nipple.
Coming off his bullet hard nipple for a moment, she whispered, "Now,
Priscilla, I am going to add another sensation. Just relax and let it
happen. After all, you certainly aren't going anywhere soon."
Miss Tellit snapped on the glove and squeezed out a generous supple of
lubricant. She found the slit in his panties and put her middle finger
through it. Peter tensed when she first touched his virgin love hole,
but relaxed as she moved her finger about his rosebud.
"Yes, Priscilla, you love it. All sissies love it. Welcome to your sissy
She gently forced her finger past his rosebud, causing him first to
tense, but then relax thanks to the preparation from his 'fanny friend.'
"Priscilla, you are about to have your first real girlie orgasm. Just
relax and allow the feeling to sweep through you entire body," she
whispered as he returned to sucking, and this time gently nibbling his
Peter needed no coaching, all his pent up sexual energy was being thrust
forward by Miss Tellit's erotic ministrations. Never had he felt
anything even close as wave after wave of pleasure pulsed through his
body and mind.
Miss Tellit inserted another finger up his love hole and increased her
rhythm. To the extent he could, he ground and gyrated his hips, trying
to meet Miss Tellit's every thrust, which cased the insidious peenie
pouch to embrace his tiny teapot without mercy.
When she finally twisted her fingers to massage Peter's 'g-spot,' he
simply lost it. He also spoke - flawlessly, without stammering. "Oooh
yeeesss!" he screamed. "Fuuuck meee! Fuuuck me haaard! I'm such a sissy
and need it!"
So powerful was his ejaculation in the peenie pouch that his frilly
panties above it actually moved.
Then he fainted. Even Miss Tellit was impressed with the ferocity of his
climax. She decided to leave him in sticky panties and satin bondage.
As she rose from the bed she looked up at the ceiling and winked. As she
quietly made her way over to the vanity to touch up her face before
leaving the sleeping sissy, she chuckled to herself, "That position
should help his dreams tonight."
"Well, anyway, 'his' dreams for now," she thought as she grabbed her
camera and silently left Peter's room.
Going back down the stairs, she made a mental note to call Auntie
Octavia in the morning. Things were progresses faster - and better -
Shortly thereafter Miss Tellit entered a darkened office. Soft music was
coming from unseen speakers. She found her way to an open breakfront
where a plasma monitor flickered with an infrared low-light image of
Peter sleeping. Pulling a keyboard and mouse shelf out, she caused a
drop down menu with MP3 selections listed to appear. She clicked on
Tuesday's selection and turned up the audio to check the transmission
quality from speakers hidden in Peter's frilly padded headboard.
Satisfied with Peter's status, she proceeded to download her camera's
pictures to Peter's personal file. She also emailed the file to her
Auntie Octavia. Tasks completed, she closed the breakfront and walked
over to a closet.
First taking out a hanger, she slipped out of her blouse and skirt, hung
them and returned the hanger to the closet. She exchanged her black
heels for an even higher white satin pair and pulled a floor length,
long sleeved sheer white negligee from the closet. After donning it, she
fluffed her hair over the robe, adjusted her pert breasts in their
quarter bra, and checked her stocking seams. Pleased with her
appearance, she turned toward the large desk at the other end of the
A dark shadow behind the desk said, "Well done, my pet. Now, come and
please your mistress as only you are able.
To be continued...
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