Crystal's StorySite

This is a female authoritarian sissy boy story, although with a softer touch than most. There is candy and spice and (mostly) everything sissy-nice! So, if lots of frilly outfits, swishy behavior and a little sex are your thing, please read on. If not, thanks for looking anyway.

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!


Miss Prissy Paunceworth

by sissystevie

Chapter I – Beginnings


The moment he walked in, she knew. All the markers were there.

"Yes, this one was perfect," a thoroughly delighted Theodosia Tellit thought.

Her critical eye examined him: narrow shoulders, slender arms and hands, legs to die for, and even long light brown hair. He was already feminine with that awkward grace all natural sissies have.

After the perfunctory new student introductions and orientations, she ran to call her aunt.


After bidding his mother farewell, a depressed Peter Paunceworth looked about his new surroundings and was neither happy, nor impressed.

His bedroom was tiny, to say the least. It must have been a servant's room - and from the pink walls, a maid's at that. The fluffy organza curtains and fussy girl's vanity were a little over the top. However, the bed, although also frilly in the extreme, looked nice enough. And the fashion magazines on the night stand reminded him of home.

"Shipped off again, while Mummy and Daddy spend the summer traveling to exotic places," he mused. "And this time to a school for retards! Well, maybe they can cure my not-so-little speech problem. That might improve my social life, but then 'anything' would improve my social life! But then, as if my stammering isn't enough, there's also my strange body..."

"Gee, this room really is a little weird. I know I wanted a single, but this looks like a girl's room - frilly vanity and all. Well, I guess the privacy's worth it. And there's an attached bath as well, even though it only has a tub and not a shower stall.

"Now, Peter me-boy, just who was that sexy woman? Miss Tilly or Tutty? She will definitely improve things around here."

A stirring in his pants told him that it was time to find some tissue and give Miss T-whatever her first 'salute.'

"I wonder what soft lacy underwear she's wearing," his mind fantasized more than questioned as he looked about the room for tissue paper.

Peter tended to consume a lot of tissue paper.


Merstead Hall was really a speech therapy clinic, not a school at all. It was located in a small New England village on Narragansett Bay. Its principal building was a rambling old Georgian revival house built by a sea captain in the clipper ship Asia trade.

Peter Paunceworth was here because he was a chronic stammerer. All too often his speech would complete block, rendering him unable to utter a single word. This had driven him into himself and his fantasies, which almost always revolved around sex.

The real reason Peter wanted a single room was that he also, barely at age sixteen, was a chronic masturbator.


After a surprisingly light dinner of clear jellied consommé and salad, he returned to his room to review the massive amount of school materials, which mostly meant rules and regulations. He was to remain silent at all times except when practicing sounds prescribed under the therapy.

"Gee," he thought, "no loss there. I never could speak to anyone other than to myself anyway.

"Well, maybe except that one time Mummy allowed me to wear her long silky nightgown and cuddle next to her... That was just before she started talking about this place."

He also would have to learn a basic form of sign language to communicate his basic needs as well as start to write his biography. Tomorrow he was to travel to Providence for a school medical exam.

Peter was a more than little alarmed by the prominent disclosure, fully acknowledged by his mother, that Merstead Hall could employ corporal punishment at its discretion.

The only good news was that Miss Tellit was to be his primary tutor. Peter was amazed to learn that only a couple of years ago Miss Tellit had been a student at Merstead Hall. She could only be a few years older than him.

Even better, during dinner she bent over several time to pick up additional school materials and he saw part of her bra. It was made from the sexiest delicate white lace.

Peter was well onto his way to a major crush on Theodosia Tellit - and he had the protruding peenie to prove it!

There was something about her that was curiously special. She was slender, with smallish breasts and almost an androgynous figure, but she carried herself in the most graceful, elegant manner. Her soft mezzo voice had a wonderful southern accent. Seeing her bra inflamed his brain, causing him to fantasize about her panties, and - heaven upon heaven - a matching garter belt.

Yes, Peter Paunceworth also had a huge lingerie fetish.

Taking some extra tissues, he crawled into bed. Much to Peter's surprise and delight, the Egyptian cotton sheets, despite being a pale pink, seemed like silk - it reminded him of Miss Tellit's lingerie, not that the boy needed any further encouragement whatsoever.

He never questioned what sort of 'school' would have such luxurious feminine bedding.


Arriving at breakfast the next morning, Peter was informed that he had to fast for his medical exam. Dejectedly he returned to his bedroom and sat on his bed, which according to school rules he had neatly made. Sitting on the frilly vanity stool just seemed too girlish. The magazines on the nightstand caught his eye, and he was well into the current month's "Vogue" when Miss Tellit arrived.

"Good morning, Peter," she beamed. "Time to go - please follow me to my car."

She was radiant in a floral print wrap skirt made from shiny chintz cotton and tight woman's tee shirt with cap short sleeves. The outline of her lacy bra was clearly visible through the sheer top, a fact not unnoticed by Peter.

In no time, they were speeding down the highway in Miss Tellit's sporty BMW convertible with its top down. Despite his gnawing stomach, it seemed a lovely warm summer's day and Peter relaxed in its embrace.

"Peter, did you start on your personal story last night?" Miss Tellit asked.

Not wanting to admit that he went to bed early and wanked twice thinking about the very person asking the question, Peter held his thumb and forefinger up to indicate 'a little.'

Theodosia Tellit smiled back in an understanding manner as she allowed her skirt to rise a bit further on her thighs. She, of course, understood exactly.

"Peter," she said, "after some adjustment, I'm sure everything will be just perfect. Not to worry. You are a unique child with unique problems, but then we have some very unique solutions."

Peter was too busy trying to use psychic kinetic energy to lift her skirt further to notice much of anything else, let alone the implications of what Miss Tellit was saying. What he had noticed was that she was wearing sandal hose, and he desperately needed to know what was holding them up.

"Well, maybe the wind from the open top will do the trick," he again wishfully thought.

Theodosia smoothed her shirt down with one hand, which brought a barely audible moan from Peter. However, the taunt skirt now revealed the outline of a suspender across her thigh, bringing another, somewhat louder, moan from poor tormented Peter.

"Oh my God," she IS wearing a garter belt!" he thought.

"They are all so very predicable!" she thought.

Changing pace, she continued, "Peter, we are almost there. Please be very cooperative with Doctor D'Oley and her staff. They will perform a very thorough physical exam. Some of the things may be new to you, but it is very important that we understand you complete physical condition. You will have check ups every two weeks while you are with us. A perfectly disciplined body builds self esteem, and self esteem will help your speech."

Arriving at the medial office building, they walked down a long corridor until reaching an office sign for Diana H. D'Oley, MD - Internal Medicine and Endocrinology.

The receptionist warmly greeted Miss Tellit and led Peter to an examination room where he was directed to remove his clothes and don a robe.

Peter was a little nonplussed by the short wrap robe, which was pale pink and made from a silk-like fabric. It certainly was not the usual ill fitting rough cotton medical garment. It also excited him - not a condition he really needed right then.

His erotic thoughts terminated quickly when a technician arrived to take blood samples. After drawing several vials, she directed Peter to the scales where his height and weight were taken.

"You are a small one," she idly commented. "Five foot-four and one-twenty."

After the technician left, an elegant lady in a starched lab coat entered. She was accompanied by a severely dressed stocky nurse whose circa 1950 starched uniform had a name badge identifying her as Mildred Manley, RN.

"Good morning Peter. I'm Doctor D'Oley and this is Nurse Manley. Please get up on the examination table and put your legs up in the stirrups."

The young boy awkwardly did so, vainly trying to maintain at least a modicum of modesty.

Doctor D'Oley opened his robe, completely baring his body.

"Mildred, let's strap him in and then take the pictures. After that we can get the baseline measurements."

"Wh-wh-wh-wh-why pi-pi-pi-pi-pi-pictures?" Peter stammered in protest as leather straps were quickly put about his wrists, legs and waist.

"Peter," the doctor snapped back, "we have to confirm your general good health and then establish certain performance baselines. Pictures are part of that.

"And you will recall that you are not to speak. Just nod, one way or the other, to answer my direct questions. Now be a good girl and do exactly as we say, or you 'will' be punished."

Peter gave her a weird look, but, recalling the corporal punishment option, wisely kept his own counsel despite being called and treated like a girl.

Nurse Manley snapped various picture starting with Peter's hair and moving down his body, part by part, to his feet.

"Okay, Mildred," the doctor said, "let's go - hair is twenty-five centimeters; ears, nice small size, three by four centimeters..."

She continued down Peter's body measuring everything, paying particular attention to his breasts, nipples, penis and testes. Returning to his breasts she prodded each, noting the fat and muscle content and then stimulating each nipple for yet another measurement.

The nipple stimulation caused poor Peter's small penis to engorge, which then was duly measured, to his great embarrassment.

The doctor clinically read off his measurements," The engorged clitoris is eight centimeters long and six in circumference. Stimulated areola is three point five across and nipple stem just shy of a full centimeter."

"Mildred," the doctor clinically commented, "observe the extensive gynecomastia, much of it extra-therapeutic. It is consistent when presented with the small genitalia and lack of body hair, isn't it? All in all, a remarkable condition for a sixteen year old, she very nearly presents as a pre-pubescent male. We shall have to mind hormonal levels with great care."

After snapping on latex gloves, Diana D'Oley lubricated and inserted a finger into Peter's rectum. Peter let out a surprisingly high pitched squeal.

"They really are all alike," the doctor chuckled before making several additional verbal observations for her nurse to record.

"Very well, Mildred, please mark the time and commence manipulating her nipples."

As Nurse Manley played with Peter's nipples between her thumbs and forefingers, Doctor D'Oley began massaging his prostrate gland.

Two minutes, ten seconds later, Peter came into a little specimen jar the doctor held over his penis.

The nurse cleaned up while Diana D'Oley wrote out several prescription slips.

"Mildred, please take care of these scripts and then get her dressed. I fear her rear may be a little sore, so please put her in some appropriate under things. Bring her to my office when you are done."

Leaving Peter bound to the table, Nurse Manley looked at the forms and walked to a cabinet to retrieve the medications. Four injections and two pills later, Peter was released.

Once on his somewhat unstable feet, the nurse handed Peter a pair of white lace and satin bikini underpants and tossed his old underpants and crew socks in the toxic waste receptacle.

"Wear these instead of those awful boy's shorts. Those socks are too ugly to be worn by a donkey. Then finish getting dressed and meet me in the hallway."

Peter was aghast, but meekly pulled the underpants up his legs to realize that they were actually panties. His mind was so clouded that he simply complied as if in a trance.

However, the panties did feel awfully nice on him.

Eventually entering Doctor D'Oley's office, he found Miss Tellit and her reviewing the examination notes.

"Ah, welcome back, Peter," Miss Tellit said as she motioned him to a seat next to her. Several vials of pills sat on the desk in front of her.

With everyone seated, Diana D'Oley began. "Okay, Peter, everything is just about what we expected. However, several changes must be made. We are starting you on a special regimen of vitamins and other healthy things that will bring your body into its proper shape. Miss Tellit has the pills you are to take until you return here in two weeks. You must also loss five pounds before your next visit here. One-hundred twenty pounds is too much for your frail frame.

"In the meantime, I want you to do two things. One, you need to take more meticulous care to your grooming. Your nails, hair and eyebrows are a disgrace. You will feel much better when they are properly minded to. Miss Tellit will guide you in these matters.

"When you leave here you will visit Miss Eugenia where the work will begin. I have already called her with instructions.

"Secondly, you must improve your deplorable deportment. Shuffling about with slouched back and shoulders is just plain unhealthy and screams of low esteem. I am ordering a thorax support and dance lessons to remedy these problems.

"Theo, when you order her cor..., er, 'thorax supporter,' please do pick up some better tailored shorts and top. The sooner she is properly cleaned up, the sooner recovery will occur.

"Any questions?"

Peter was so befuddled that all he could manage was a nod. His being referred to in feminine pronouns seemed weird, but not worth protesting. The doctor and nurse terrified him. Clearly these two women were not to be trifled with.

Miss Tellit air kissed the doctor and said, "Nope, Diana. Thanks for everything. It seems we have some chores for the afternoon."

She took the dazed Peter in hand and led him back to her car.

After driving a short distance, Miss Tellit parked in front of a shop with a sign saying 'Elegance by Eugenia.' The wobbly Peter was escorted into the shop by Miss Tellit to be warmly greeted by a stern looking elder lady, who turned out to be Eugenia, herself.

Miss Tellit warmly smiled and said, "This one has doctor's orders to be 'cleaned up.' Did you get a call from Diana's office?"

"We did indeed, Miss Theo. Lisette is waiting in back. I think it will take several hours. The doctor ordered rather an extensive 'clean up.'"

"Excellent," Miss Tellit responded. "She's a bit groggy from her medications and may well doze off. May I suggest you restrain her as a precaution? I have a lot of shopping to do and will return around four-o'clock with her new outfit. Does that work for you?"

"Perfect, I'll see you then," Eugenia said. Then turning to a barely conscious Peter, she continued, "Follow me, sweetie. Trust me, you will feel so much better about yourself when we are done with you."

Peter now was feeling quite sleepy and welcomed the massage-type table Eugenia and her assistant placed him on. He was fast asleep before his head hit the pillow.

"Right, Lisette." Eugenia said, "Time to get to work. First cut those awful clothes off and then strap her down. If she's wearing panties, which I suspect she is, put them to one side. I'll check the front desk to see if the program arrived from Doctor D'Oley's office."

Returning with a small I-Pod, Eugenia plugged in a pair of earphones and checked its selection and volume. After and putting the phones in Peter's ears, she studied her new subject.

"Lisette, isn't she a beauty? I don't think I've ever seen one so naturally feminine. The only shocking thing about her is that she has those awful things between her legs!

"Well, Ma'am, that's always correctable," Lisette giggled while making a scissors-like motion with her fingers.

"Anyway, back to work.' Eugenia said. "Thank goodness she's a brunette with pale skin. What little hair she has should react beautifully to the treatment. We'll shave her lower legs and underarms for today.

"I figure two hours here with the lasers and shaving, a half hour to clean her up, and then at least another hour in the chair for the rest. Let's start with her backside. Then we can turn her over and get her chest so that we can attach the breast devices."

For the next ninety minutes, Lisette and Eugenia worked with skilled hands to remove all vestiges of body and facial hair from Peter's eyebrows down. For most of that period, electric pulse patches on his breasts caused them to gently contact and relax. Over the patches were two large plastic vacuum cylinders that slowly suctioned his breasts in and out. Both women marveled at the existing development of his nipples.

As they thoroughly sponged him off, Peter slowly came awake.

"My, Peter, you had a nice little nap," Eugenia cooed. "Did you have any sweet girly dreams?"

"Huh," responded Peter.

"Remember, dear, no speaking." Eugenia said. "Just be a good girl and do as you are told. We have to massage you with some creams and then get you over to the salon chair. Okay, hunny bunny?"

Peter just dimly nodded.

He loved it when they rubbed the oils and creams into his back and was only mildly troubled when they inserted something into his rectum. The massage about his derriere was just too divine a feeling.

When he was turned over, he noticed his breasts. "Oh my God," he thought, "they've grown! Now that is something I really do NOT need!"

However, as Eugenia began to rub them with her ointments the pleasure trumped any of his concerns. He always had liked playing with his nipples, but never had anything felt this good. They seemed to have come alive.

His moaning was equaled by the swelling on his tiny peenie, which neither woman seemed to take offense at. In fact, Lisette took time to rub some oil all about his little boy tower.

Before the massage got the best of him, the two women had him brought him to his feet. Lisette had him step into his panties and raised them up his now smooth legs to his hairless crotch.

"Now, sissy, don't they feel so much better now?" Lisette rhetorically asked.

Peter was again nonplussed by the constant use of female pronouns and new use of the word 'sissy.' Frankly, he felt like one - not only in looks, but also for being such a total ladies' boy wimp!

Before he could think about it further, Eugenia held out a frilly satin dressing robe. Putting it on further assaulted his senses. Everything felt so much better now with his newly ultra soft skin. His nipples tingled under the robe's soft embrace.

And that thing in his fanny almost felt pleasant as he moved about.

Things were coming at the boy very fast. Very, very fast!

The two women helped Peter to the salon chair and sat him down for the next phase. Peter let out a soft sigh as that 'thing' in his rear found new purchase.

Lisette washed and conditioned his hair while Eugenia assembled various things on a movable tray table behind the chair. Once his hair was done, Peter leaned back to have Eugenia apply various smelly lotions to his hair while Lisette worked on his nails.

His finger nails were considerable longer when Lisette turned her attention to his feet. About that time, Eugenia finished with her awful lotion and began putting his hair into tight rollers of varying sizes.

Once a net was stretched over his roller-covered head, Eugenia held his right earlobe in her hand, brought a device up to it and made something in it click. Peter felt a sharp pain and immediately realized that he had been pierced. Before he could react, Eugenia repeated the process on his left lobe.

"Bu-bu-bu-but," Peter began to protest.

"Hush, sissy!" Eugenia barked. "You know that you are not allowed to speak. If you say another word, I'll double the piercings - and then tan your rear!"

Utterly defeated, and still a little out of it mentally, Peter slumped into the chair, which caused him to notice his coral pink toe nails.

"Oh my God," he sighed to himself. "What have I gotten into here?"

Eugenia attached a large bonnet over his head and powered up the dryer.

As Lisette turned her attention to Peter's new quarter inch finger nails, Eugenia began plucking his eyebrows in earnest.

"Don't you dare move, sissy. You already are more than half way to a spanking as is!" Eugenia cautioned. "And hold your hands still for Lisette, or we will have to secure them."

After completing his brows, Eugenia turned her attention to Peter's face. She carefully painted a coral pink liquid over his lips and a thin dark brown line at the very end on his eyelids.

"My God, Lisette, come look at her lashes. We'll have to curl them!" Eugenia exclaimed.

Lisette appeared with a curler and marveled at the length and fullness of Peter's eyelashes. Peter was simply addled, so confused was he. Sensations were running through his body that never before had he experienced. Eugenia quickly finished up Peter's face with some blush, light hazel and brown eye shadow, a touch of mascara, and lip gloss.

Just then Theodosia Tellit returned carrying a large shopping bag.

"Ah, Miss Theo, you're just in time for the comb out" Eugenia said.

Miss Tellit gleefully responded, "What fun! The birth of another sissy! Let loose, Ladies! I can't wait to see the fruits of your efforts! Then we can see how she looks in her new outfit."

Eugenia undid the net and curlers to reveal a mass of curls atop Peter's head. As she tackled the mess with her comb and teasing brush, Lisette showed Theo Peter's smooth skin and highly polished pink nails.

Peter submissively sat in shock as the two women gushed over how well he looked. Each time he became conflicted about his new image, the same tune came into his mind - "I feel pretty, oh so pretty..."

"Damn," he thought, "I cannot get that out of my head!"

But he was pretty, and he knew it! Worse, he was becoming prettier by the minute as Eugenia worked her combs and sprays.

At last, Eugenia finished her fiddling and directed Peter to stand before a floor to ceiling mirrors in an alcove just off from the main salon. She removed his robe and told him to pose in his bikini panties in various postions while Lisette took pictures with a digital camera.

"Don't you dare resist, sissy, or we have pictures of you being thrashed with my strap!" she again threatened.

Pitiful Peter again meekly complied. However, the fact of the matter was that he was absolutely transfixed by his totally feminine appearance - those feelings being best expressed by the small tent in his panties.

But he was beautiful. His small slender body with long slim neck, soft slender shoulders, budding breasts with urgent nipples, lean limbs and gracefully long fingers were only part of it. Now, his head was also beautiful. His long brown hair, now slightly lighter with subtle auburn highlights, cascaded down his high cheek bones and pouty lips in a short Katharine Hepburn pageboy, complete with barrette on one side. In fact, he quite resembled a young Hepburn.

"Perfection! Or should I say 'Prissy perfect!'" exclaimed Miss Tellit. "Now, ladies, let's get her dressed. Her 'thorax support' has to be delivered later, so her tight lacing will have to be deferred until later."

The three women dug into Theo's shopping and began dressing the hapless sissy.

A lacy bra, that just 'happened' to match his panties, almost undid the poor boy. The lace tickled his distended nipples in the most electrifying manner. The full cup bra gathered his flesh to accentuate his budding boobies in a way that he never could have imagined.

"You know, Miss Theo, I dare say she is almost a full 'A' cup. A most impressive starting point!" Eugenia exclaimed.

"I see," replied Miss Tellit. "Good job I bought several bras. It simply would not be proper for her to go without one from now on. Let's get her knee socks and shoes on, and then we can complete dressing her."

Lisette bent down and pulled opaque sheer white knees socks up to just below her knees. Their tops were finished out in sweet ruffled fold-overs with a sweet puffy white satin bows in the rears, which the poor boy failed to notice - at least for the moment.

Peter loved the feeling against his smooth legs and secretly wished they were real stockings.

Lisette marveled at the petit size-six size of her feet as she bucked up Peter's black patent mary janes. They had one-inch heels and pretty charcoal grosgrain ribbon bows on their toes.

So enthralled with his lingerie was he, that he almost resisted covering it up until he saw the blouse. It was an old fashioned white polished cotton girl's blouse with a round 'Peter Pan' collar. He loved it - it fit so much better than Mummy's blouses. The neck was just perfect, and it fit perfectly over his bust and down his slim waist tightly, but comfortably. Its short sleeves were divine.

His shorts came next. This time Miss Tellit, herself, did 'the honors,' which distressed the poor boy's pulsing peenie even further.

The shorts were more engineered than designed. They were very short and made from elasticized charcoal silk gabardine. Miss Tellit slid them up Peter's smooth legs and pulled them about high on his waist. It was going to be a very tight fit.

The fasteners were on his left side, leaving his front flat, but for the little 'urgency' in his panties.

"Good job his peenie is so small," laughed Eugenia, "or else I'm afraid we would have to milk the poor thing!"

"Let's just hope she doesn't squirt all on her own," Miss Tellit chuckled back. Moving to Peter's side, she ordered, "Now, dear, breathe in deeply and hold it!"

With a fierce tug that almost pulled the disbelieving Peter over, she thrice hooked the wide waist band closed and tugged the zipper up.

The shorts were almost like a panty girdle from their high waistline down to Peter's hips. His front was stretched taunt - causing some peenie discomfort, let alone 'correction.' He must have lost two inches from his waist. Their rear was cut in a manner to both lift his sweet sissy cheeks and accentuate the divide between them - yielding yet another sensation to that 'thing' up his bottom.

From the hips down, the shorts opened up about his thighs, coming to and end only a few inches below his hips.

Lisette approached with some jewelry and gushed how cute it would look on him. "We have a nice little pearl strand for under your collar with a matching bracelet. And just look at this cute gold ring with two pearls! See, it matches you cute ear studs!"

Peter stared into the mirror, not sure what he was looking at. It certainly was not a boy in any way, shape or manner! Nor, was it really a girl - close, but not really. The only thing it could be was precisely what they were calling him, a sissy! A total sissy, plain and simple!

Reading his mind like a book, Miss Tellit approached him and whispered in his ear, "Yes, Peter dear, you now ARE a sissy." Pressing her bosom into his back, she added, "And you are MY little prissy sissy!"

"Prissy" rang a bell in Peter's mind - or what was functioning in lieu of it. Then that tune came back into his head, "I feel pretty, oh so pretty..."

"And don't you just 'feel pretty, oh so pretty,'" Miss Tellit giggled as she stepped back to allow Peter absorb it all.

After allowing his mind a few choruses of 'I feel Pretty,' she again approached with a little prettily wrapped box. Again whispering in his ear, "Sweetie, I have a little present for you. Would you like it now?"

Peter nodded and took the proffered white box with a pretty pink satin bow. Carefully unwrapping it - a girly trait that greatly pleased Miss Tellit, he opened it up to find another strand of pearls with a large gold heart-shaped charm hanging from it. Written on the charm in bright pink enamel script was the word 'Sissy' over the word 'Prissy.'

Seeing 'Prissy' almost set off another verse of 'I feel pretty,' but Miss Tellit pressed forward.

"Isn't it so pretty?" Miss Tellit cooed. "Here, dear, let me put it on."

She took the bracelet and put it about his right ankle, making sure that she spent time to smooth out his knee socks and run her hands up his thighs to straighten out the flared bottoms of his shorts - front and back.

Lisette handed Miss Tellit a tiny white silk gabardine hand bag, which she opened to inspect its contents. Still standing behind Peter, who could not take his eyes off his reflected images in the long mirrors, she held the bag out in front of him.

"Peter, this is your bag, and you must take it everywhere you go when dressed in this outfit. Now look at what's in it. Yes, sweetie, that's your lips gloss, powder compact, some blush and shadow and a tiny little lace hankie. Everything a proper sissy needs!"

"Peter seemed to accepted everything with a weak smile, but held up the one item Miss Tellit had failed to mention - a small scarlet note book and fit-in pen that had a black script letter 'P' on its cover.

"Oh, sweetie, that's your 'P-Book,' replied Miss Tellit.

His eyes questioned again, and she answered, "No Peter, the 'P' is not for 'Peter,' or even 'Prissy,' but rather for 'punishment.' When you are a bad sissy, I, or another of your superiors, will make a notation. That way I can keep track of things. Isn't that just so practical?"

'Prissy' had started songs going off again in Peter's head, but 'punishment' brought them to a screeching halt. He looked at Miss Tellit with terror in his eyes.

"Oh not to worry, at least for now my sweet," she soothed. "See there is nothing in it."

Peter opened the book to find two notations for speaking made by Eugenia and gasped.

"Oh, my!" sighed Miss Tellit. "And I overlooked your indiscretions at the doctor's office. Well, you don't have to worry about them until Friday evening anyway. Just try to be a perfect sissy from now on."

Changing the subject, she said, "Ladies, please take the pictures of her first school uniform and then we shall be on our way.

"Peter, please look at yourself in the mirror and think how pretty you look. I want you put on your prettiest poses for the pictures, or else I shall have to make one of those dreadful notations in your P-Book."

Peter absolutely vamped for the camera - actually getting quite carried away by it.

Completing the photos, Miss Tellit told Peter to bow to each of the ladies to thank them for all the wonderful things they did for him that afternoon.

After the goodbyes, she picked up a box of cosmetics and led Peter to her car for the return trip to Merstead Hall.

Peter was in such sensory overload that he mercifully failed to notice the astounded reactions of several passersby. Likewise, he took no notice whatsoever of the fact that he was in an open top car.

"Well, that was quite a day, wasn't it, Peter," Miss Tellit asked after they were underway. "Maybe you would just like to hear some pretty music for the drive home.

"As you know Peter, stammerers rarely stammer when they sing, and some even do not stammer when they speak in a foreign language. One actor can even act without stammering, but can barely put two words together in conversation. So if you wish to sign along, please do. It's good for the soul!"

She slipped a copy of "West Side Story" into the CD and cued forward until she found the song she was looking for.

"I feel, pretty, oh so pretty..." came out of the speakers and Peter zoned out. Within five minutes he was humming along; in ten minutes he was not only singing in a sweet falsetto voice, but also rocking back and forth on his butt plug.

After making her second CD back cue to keep the same song on, Miss Tellit opened up her mobile phone and hit speed dial.

"Auntie Octavia, hi, it's Theo.

"Well, on a scale of one to ten, the day was at least an eleven. Everything went more than perfectly. His mother and the preliminary assessments were spot on.

"Oh, he's here in the car. Just listen..." She moved the phone over to the obliviously singing Peter for a moment.

"No suggestion or coaching at all. He started out in that voice!

"Yes, Diana was actually amazed at his development.

"Rather than tell you, you should have some pictures e-mailed from Eugenia within the hour. Just amazing! I have to bring the little dear back down to earth before we return to Merstead Hall.

"Anyway, to cut to the chase, I think he's ready for an outing this weekend.

"I'll call you after I put him to bed. Bye-bye, love you too!"

She undid two buttons on her blouse to 'accidentally' show here lace bra and carefully arranged her skirt's wrapping to fully display her right stocking top and garter.

She switched off the CD and nudged Peter. "Peter, you certainly do like that song! You sing it so sweetly. Soon we will have you speaking just like that."

Peter actually smiled back at her, and then, upon seeing her 'accidentally' open blouse and open slit of her skirt, allowed his jaw to drop.

Miss Tellit, of course, ignored his lecherous leer and announced, "Tonight we will eat at our own table again. Tomorrow you may join student body - they are all dying to meet the new sissy! I think you will come to enjoy your school days with all the fun lessons.

"Now, sweetie, when you get out of the car I want you to take small delicate steps and keep your elbows tucked to your sides. You look so adorable in your new school uniform. You must not only look, but also act your best in it. Bad deportment will only get you a notation in your P-Book, but acting sweetly will get you praise from everyone - and especially from me.

"After dinner, I will show you how to properly prepare yourself for bed."

Conscious of where his eyes were focused, she ran her hand across her bosom and down to her thigh, and added, "And if you are a very good sissy, I shall give you a wonderful surprise when I tuck you in bed."

They pulled up to Merstead Hall's port-cohere entrance and parked.

Miss Tellit said, "Mind your girlie deportment, my dear. We have to carry a few parcels in, and it will take several trips. The rest of your new wardrobe will be delivered as the week progresses. Then we will freshen up and have an early supper."

It took three trips to carry all the parcels, including the cosmetics, up to Peter's room. During the process, Peter became acutely aware of his long nails and their striking pink enamel. Several times he paused to admire his hands, which delighted Theodosia Tellit immensely.

The cosmetics, including Doctor D'Oley's pill vials, were added to those many feminine items already on the vanity and in the bathroom. The contents of two large shopping bags filled with panties, bras, and knee socks were very carefully placed in drawers by Peter under Miss Tellit's keen supervision.

Again, Peter paused several times to inspect his hands. To him, they seemed to define something new about him.

He slowly realized that all his boy clothes were missing, but the constant directions from Miss Tellit kept him moving forward.

Peter hung up several addition 'uniforms' exactly like the one he was wearing in the large walk in closet, which was at least half the size of the bedroom, itself.

Other boxes contained pairs of mary janes, white ballet slippers, and white satin mules with three-inch heels and feathered toes. Each pair was put in a shoe rack in the closet. Miss Tellit told him to place two final shoe boxes marked 'Miss High Heels' on an upper shelf.

Now down to two boxes, Peter opened the smaller one to find two satin and lace baby doll night gowns - one pink and the other baby blue.

"Oh, Peter, don't you just love them?" Miss Tellit gushed. "Please pick out one for tonight and hang it in the bathroom. I'll put the other away for you."

Peter's first reaction was embarrassment. Both were so utterly girlie, but holding them was another matter. "Sugar and spice and everything nice," went through his mind as his itty bitty peenie stiffened. He selected the baby blue one, somehow thinking it less feminine.

The last parcel contained two frilly white pinafores. Miss Tellit directed Peter to hang one in closet and lay the other on his bed. As he did so, he drew a breath when he saw 'Prissy is a Sissy' embroidered across its front in cornflower blue satin thread.

"Good job, Peter," Miss Tellit announced. "Now let's repair our faces and go down for supper."

She led him to the vanity and showed him how to touch up his hair and makeup while also repairing her own. She made sure that her semi-exposed bra was either touching him or directly in his line of sight.

Satisfied with the repairs, Miss Tellit had Peter step over by the bed. "Now sweetie, time to put on your pinafore. You will wear it for all meals and also at other times when learning new skills. Isn't it to die for?"

Peter blushed. If the uniform was fit for a sissy, the frilly apron was fit for the sissy queen.

It was made from heavily starched polished white cotton and organza and pressed to perfection. An impossibly frilly bib covered his titties and came to a broad tight waistline. From there, the apron continued down to a wide, flared skirt, which had ruffled organza and lace layers underneath that were slightly longer than the outer skirt portion. The ruffles ended just below his shorts. The effect was almost like a tutu.

Straps from either side of the bib went over his shoulders and crisscrossed over his back. They buttoned to the waist sash that Miss Tellit had tied into a huge bow at his rear. The fancy script 'Prissy is a Sissy' was displayed across his boobies for all to see.

Peter was only dimly aware that he was in his very first petticoat. His peenie, however, realized that something very special had just happened. To Peter's 'little head' - in his case, a very little head - it was even better than Miss Tellit's lingerie.

Peter could not resist putting his hands down to fluff the sides of the petticoated skirt. He thought that his bright coral nails contrasted so nicely against the pure white of the pinney.

"Oh you look so prissy perfect! Maybe we should just start calling you 'Prissy!'" Miss Tellit giggled as she handed him his purse. "Now a few instructions."

She posed Peter's arms with elbows tight to his side and arms held forward with bent wrists. "Yes, that's perfect," she said. "Now, hold your bag with just your thumb and one or two fingers.

"Okay, now chin up, neck straight and shoulders back. When people look at you, you 'will' give them a cute smile back. If you blush, not to worry, it's expected from a sissy and they will think that you are even cuter!

"Next thing - put one foot before the other, toe to heel, with very small steps. This is called mincing. All sissies mince, and Peter, from now on, you 'are' a sissy and you 'will' mince!

"And a final thing - table decorum," she said as she moved over to the small frilly bench before the vanity. "Watch how I sit down and mind how I smooth out my skirt as I do it."

She sat down twice and then required Peter to do the same. After five tries he was acceptable, his seating being more difficult in petticoats.

"And, Peter, when you sit at the table, I want your knees locked together and your posture as erect as when you are walking. Never take food that covers more than a third of your utensil. Use your napkin daintily - just lightly touch your lips with it.

"Moreover, if you get too embarrassed or do not think this is necessary, think about the notations I shall make in your P-Book when we sit down! If you fail me completely, I shall take you over my knee right then and there and give you the spanking of your young life in front of the entire school.

"Does my sissy understand?"

Peter meekly nodded, terrified both of being punished and displeasing this beautiful, but demanding, young woman.

"Excellent! You may also think of what good behavior brings. Remember, I want to give you a wonderful little surprise when I put you to bed. However, surprises only come to good sissies."

With that, she took Peter's delicate manicured hand in hers to lead him downstairs to the dining room.

She continued holding his hand as they entered the busy school common room and then forward into the dining area.

Peter was acutely aware of silence as they passed. Everyone was staring at him. "Mind your deportment," Miss Tellit whispered, "and smile at your fellow students and the staff! Please your Mistress!"

Peter thought he did a magnificent job. Of course, it was awkward and gangly, but it also had an underlying grace from deep within him. Although poor by any trained sissy standards, Miss Tellit was delighted. His natural feminine grace was readily apparent, and more important, he was trying. That was all that mattered right now to her.

She led him to a small table that was literally in the center of the dinner area. Miss Tellit held a chair out and Peter managed to lower himself into the chair in more than an acceptable manner.

"Well, that was something," marveled Miss Tellit to herself. "I know he's been wearing his mother's things for years, but in a petticoat..."

Dinner, really more of a light supper, went well. Peter again had a rich beef broth and a small salad and managed to conduct himself in more than an acceptable manner.

From time to time, Miss Tellit made sure that Peter got an eyeful of her charms. It kept his mind off all the staring eyes and whispers about him. She also offered some positive reinforcement, always referring to him as a good sissy.

"Okay, sweet sissy, if you make it back up to your room as well as you have done up to now, you shall receive your little treat. I will come about and help you rise of your chair, just as we practiced. Then you shall mince out of here smiling at everyone you pass.

Peter's exit was actually much better than his entrance, adding to Miss Tellit's delight.

Once in his room, Miss Tellit helped Peter disrobe, directing him to carefully put everything away in its proper place. He was mortified that his peenie was perhaps the most erect of his life as he stood nude before his dream princess. One of soft small hands tried to cover it up while the other, surprisingly, tried to cover his titties.

"Aren't we the modest one," Miss Tellit giggled. "First into the bathroom to remove your little fanny friend and cleanse yourself like a proper sissy."

She showed Peter how to remove his plug, wash it with disinfectant, and then give himself a 'douche.'

"Now, Peter, sit down at the vanity, and I will show you how to remove your makeup."

She was even more impressed that he smoothed a non-existent skirt as he sat. A brief practical lesson in makeup remover, astringents and moisturizers followed. Peter was shocked that some of his makeup would not come off, but Miss Tellit told him that was how it was meant to be, and as she gently brushed his hair he could not have cared less.

"Most nights, you would take a bath now, but today was exhausting, and I know you want your little treat. So let's get your nightie on and then I'll give you the treat of your life - so far, at least. Be sure to make everything perfect with your nightie. Always check yourself in a mirror before you make an entrance.

"Oh, and take the mules from the closet. They will look divine with your nightie."

Peter almost flew into the loo to put on his gown, his only though being getting back to his surprise treat. However, putting on the babydoll was somewhat of an unexpected epiphany.

The panties were made from pale blue double sided satin with ruffles at every opening. They were wonderful to pull up smooth legs, but heavenly across his derriere and front. The ultra smooth fabric mercilessly caressed both his stiff peenie and his little pink silk purse below. His hands went up to pinch his hard nipples.

"Peter, don't you dare squirt!" came from the other room. "Finish up and come out here - using perfect deportment, or your treat will turn into a torment!"

Peter managed to don the mules and the frilly empire-waisted satin top. Its top was made from pale blue sheer nylon with wide panty-matching satin trim at every edge and hem. Two very short puffy sleeves descended down into a low square neckline. A blue satin ribbon about the empire line was secured with a large bow underneath his bosom. The empire bodice caused his little breasts and bullet-hard nipples to be clearly outlined, if not partially visible, under the sheer nylon. The remainder of the top flared out to end at his panties.

After quickly running a brush though his hair, he paused for a second to collect himself, and then opened the door. What greeted him almost caused him to faint.

Miss Tellit was reclined on his bed wearing only her lingerie and heels.

Peter stopped, put his hands to his mouth and squealed in the highest voice imaginable.

"Come here, my little sissy. Your Mistress has a treat for you."

Peter had been nonplussed and flummoxed most of the day. Now the poor boy was totally lost.

His eyes traced down Miss Tellit's figure. Her long honey brown fine hair curled about her long neck and broad, but thin shoulders. Her matching lingerie was made from light cafe-au-lait colored French lace over beige sheer nylon.

Her bra encased her perfect 'B' cup bosoms, but allowed a glimpse of her small, but perfectly formed nipples. The garter belt stretched across her waist, and its lacy slender suspenders traced to attach to her sandal stockings. Her bikini panties had lace covered thong sides between the triangles covering her most sacred charms. Her cafe-au-lait four-inch heels were the finishing touch to her sexy outfit.

Peter's body began to tremble. Never had he been with any woman in such an intimate manner. And this was just not 'any' woman to Peter - it was his princess-mistress!

"See what good little sissy boys get!" she teased. "Now come over and I shall begin to teach you how to worship your Mistress. You may start by respectfully kissing my shoes."

After a few minutes, she cooed, "Such a good sissy. Now you may nurse on my bosom. Yes, that's right, worship my bra first and wait until I bare my breast for you.

Peter nuzzled into her right bra cup as her right hand went under his shoulder and began caressing his nipple through his sheer babydoll top.

"Oh, Prissy, that feels so good," she huskily said as she lifted her left breast over the bra's cup. She turned towards him to place the bared nipple to his lips. "Here, first kiss and then suckled your Mistress like the little helpless sissy that you are."

As Peter took to her nipple, she moved her left hand over to his satin panties and began to slowly knead his petit pulsating peenie. She felt her own panties dampen as her body responded both to her love of control and his tender ministrations. She wanted it to last as long as possible, which given a neophyte sissy would not be very long.

"Oh my God, he suckles like a dream." she thought as her needs became more urgent. "He's not ready for my pussy. I'll have to take care of myself."

She moved her left hand to her pussy, easily finding her own engorged clitty, and moved her stocking clad leg over Peter's tented panties. Peter barely seemed to notice the exchange of hand for leg as he began humping his crotch against her.

"Aaah," she sighed, deciding to let thing take their course. "Worship your Mistress, my darling Prissy."

They came together. It was a remarkable climax for Theo. It was tectonic for Peter.

She moved his sweet face in it up to her lips and tenderly kissed him. Not saying a word, she rolled off the bed, pulling Peter into her position. On her feet she tucked him in, gently kissed his forehead, gathered her clothes and left a thoroughly exhausted sleeping boy to his dreams.


To be continued...

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