The Art of Petticoat Punishment

by Carole Jean

Part 4.9 - Nan Gilbert Unpublished Stories

For the first time in more than 40 years there are

'new' Nan Gilbert stories!

Several of Nan Gilbert’s classic stories of Petticoat Punishment were published. I have reviewed The Panty Raiders, Tales from a Pink Mirror, Adventures in Petticoats, Transformed, Leslie’s Adventures in Petticoatland and his published short stories elsewhere on my web page.

Gilbert wrote many other stories that he shared with his friends. Most of these stories included one or more drawings by Barbara Jean, BJ. These stories were never published and the quality of the reproductions of BJ’s art was quite poor. Fortunately I own most of the original art and was able to have BJ redo the other drawings.

Some stories were not illustrated so I commissioned drawings by Juan in a style I think Gilbert would have liked.

Now available for downloading, for the first time anywhere are dozens of Nan Gilbert’s unpublished classic stories of Petticoat Punishment and humiliation presented with illustrations as the master intended.

Item #80

Three stories of Petticoat Punishment

By Nan Gilbert

Illustrated by BJ


A crimson flush darkened his cheeks as the women drew the froth of petticoats from side to side, teasingly remarking, "Little girls love rustily petticoats!" His wry expression afforded them considerable amusement.


Master Lindsay slowly accepted his status as his Mummy's little darling. Of course there were anguished moments when he would hear other boys jeering at him or making cutting remarks about his cissy clothes.


"PETER! You nasty, horrid boy! WHAT are you doing here in my room, wearing that gown? How COULD you!" His Sister’s tone was grim.

“I… I…" Peter whispered lamely.


Item #81

Three stories of Evelyn’s Petticoat Punishment

By Nan Gilbert

Illustrated by BJ


Miss Sylvia, a wealthy spinster, had been searching for months to find a suitable youth whom she could transform into a replica of herself as a little girl. She often stood before the large oil painting of herself remarking, "I'll find a twin for you darling, no matter how long it may take!"


" I would suggest that Evelyn be dressed in a fashion becoming to a prim little six-year-old, which of course would be more in keeping with 'her' status, if not 'her' sex, when appearing in public!"


“As I informed you, you will be accompanying me to a tea given by a close friend. You are to be dressed as a prim little ten-year-old Miss!" Sensing your agitation at my pronouncement, I burst into peals of gay laughter.


Item #82

Two stories of Nancy ’s Petticoat Punishment

By Nan Gilbert

Illustrated by BJ

( Nancy was one of the names the Nan Gilbert called herself so these stories may be autobiographical)


Howard's Aunt had one favorite punishment she subjected him to if he displeased her. She would order him to his room to undress and then array him in elaborately frilled drawers, petticoats and a frock, even chancing his name to ' Nancy ' while he wore them.

On this particular afternoon he was seated disconsolately on a chair placed in front of her, the picture of crushed boyhood, for, despite his fifteen years, she insisted on dressing and treating him as a child of seven. With a knowing smile, she observed, " Nancy dear, we are going to have visitors this weekend. My youngest Sister and her darling Daughter, Susan! It will be nice for her to have a little girl to play with!"


Little Nancy was the Pet of all his Aunt's friends, for, although fifteen years of age but rather small or a boy that old, she insisted on dressing him as though he were a little darling girl of six.


Item #83

Two stories of Paul’s Petticoat Punishment

By Nan Gilbert

Illustrated by BJ


He certainly was not looking forward to visiting his Aunt; that is why he had pleaded so vehemently with his Mother to stay at home. He could remember the last time when his Aunt and Cousins visited. He had had a miserable time then from his Cousins' teasing of what they called 'the little boy dainty clothes' his Mother liked to dress him in. What would it be like this time now they were all older?


"Let me out of here!" he shouted, tugging on the door handle.

"In time, Paul, that is after you have been dressed in something more becoming!"

He turned to face me, wide-eyed with apprehension. "You… you... mean…!" he simply chocked on the words to finish the sentence.

"Yes Paul, we are going to turn you into a sweetly frocked little Miss!"


Item #84

Two stories of Phillip’s Petticoat Punishment

By Nan Gilbert

Illustrated by BJ



Aunty glared at me, as she sought to console the weeping girl. "What did he do?" she asked quietly.

"He... he... tried to lift my skirts!" she whimpered. This announcement was accompanied by a sudden hushed silence from the girls, who looked at each other aghast. At that moment I wished the floor would open under me and swallow me up.


Mary stood transfixed for a moment, her eyes lit up with excitement, her hands clasped over her bosom in an expression of ecstasy. "Oh Mommie, he's cute!" she giggled.

"This is your new sister Phyllis!"

"Oh what a cute name!"

"Don't you dare call me that!" Philip demanded, making a threatening gesture as he moved towards her. His petticoats frou-froued prettily. His face became one of despair, and he stopped where he was, bursting into tears anew.


‘Robert’ is the victim in the next several stories. Nan Gilbert chose to use this name as it is BJ’s real first name.

Item #85a

Four stories of Robert’s introduction to Petticoats by his Aunt

By Nan Gilbert

Illustrated by BJ


As he emerged from the fitting room, clutching his Aunty's arm to keep from stumbling over his heels, to his horror, he spied a girl of whom he was very fond approaching, accompanied by her Mother.

"Oh please, Aunty! Please don't let her see me like this!"

With a malicious smile, Aunty whispered, "Why Roberta! You astonish me! I thought you would be thrilled to have everyone see your pretty new ensemble!"


Robert peeked out from under half-lidded eyes. His lips drooped, his eyes opened wide, appearing about to pop out of their sockets as he stared in disbelief at his reflection, shouting, "OH NO! That can't be me!"

With a merry laugh, Susan retorted, "Of course it is you, Miss Roberta, who else could it be?"


"Yes Robert, it would be unusual for a child of your age to have a governess; but, in as much as your status will be that of a ten-year-old girl, it will be quite proper!"

I sat stunned into silence, 'governess', ‘ten-year-old girl’! Surely I had not heard her correctly.


The giggling girls screamed and stepped back as Robert made a menacing motion towards them. He stopped short as Mademoiselle gave him a smarting slap on the cheek, hissing, "There will be none of that, Miss Roberta! Now apologize to your cousins!"


Item #85b

Five more stories of Robert’s introduction to Petticoats by his Aunt

By Nan Gilbert

Illustrated by BJ


Placed facing the mirrors, Robert wept softly as he stared in disbelief at his reflection. Surely this pretty little sissy staring back at him from the depths of the mirror could not really be himself. His Aunt put her hands on his arms, whispering, "There Roberta darling, aren't you thrilled that Aunty has decided to convert you into a charming little Miss?"

Robert whimpered, "Oh Aunty, I just want to die, I'm so miserable!"


"No tears please. You wouldn't wish to ruin your makeup, would you Miss Roberta!" She dabbed at his eyes with a tiny lace hankie.

"I don't care! I don't want to go down there!" pleaded Robert, struggling to hold back. It was for naught as he found himself being marched down the staircase.

He shut his eyes tightly to blot out the sight of his Aunt and cousins derisive expressions when they spied him.


"Oh Martha, really I am literally at my wits end to know what to do with Robert. He has become simply impossible of late, and the neighbors are complaining about his mean, bullying ways towards their daughters. Oh what can I do? I have tried chastising him and depriving him of privilege, none of which seem to have any effect. Tell me, do you know anything that would help?"


"From this moment on you will be addressed as 'Miss Roberta' and wear charming costumes to please me!" Robert burst into hysterical sobbing, Mademoiselle adding to his mortification by tilting his chin upward, dabbing at his eyes with a tiny lace hankie.


Aunty, "Phyllis, I want you to tell me how Robert acts this afternoon, as I have warned him that any ungentlemanly behavior and I shall put him into dresses for a month. You will report to me won't you?"

Phyllis (gleefully), "Oh yes!"


Item #85c

Five stories of Robert’s debut in Petticoats with his Aunt

By Nan Gilbert

Illustrated by BJ


After months of severe figure training and deportment, Robert's Aunty feels it is time for her to present her darling, feminized boy-girl to the public.


"I have invited several of my close friends for tea this afternoon, and you, darling, are going to model your pretty clothes for them.'"

"Oh Aunty, must I?"

"Why I thought you would be very excited over the prospect!"

Aunty gay laughter echoed about the breakfast room on spying Robert's dejected expression.


"Darlings, this is my precious Roberta!"

The ecstatic exclamations of the ladies of the Androgynocracy Society, sweep about the room:

"How adorable!"


"I have a delightful surprise for you Roberta darling. One which I am positive will quite thrill you! "

A slight tremor caressed Robert's frame as he sat demurely in his lavishly frilled boudoir, facing his Aunt. The slight movement caused the folds of his elaborately frilled pink satin negligee to shimmer, and it was not missed by the eagle eye of his hunt. "Yes Aunty," he murmured.


With genuine approval, his Aunt exclaimed, "My, don't we look sweet! Why you're as pretty as a picture! The other children will simply be green with envy when they see your lovely ensemble!"

Robert winced, a deep flush darkening his cheeks, a tear starting to trickle from his eye as he pleaded, "Please, please Aunty, say I don't have to accompany you! Everyone will laugh at me, dressed this way!"


Item #85d

Four stories of Robert’s life in Petticoats with his Aunt

By Nan Gilbert

Illustrated by BJ


Aunty decided to adopt a lad of Roberta's age and train him for duties as a 'Personal Maid' to Roberta.

Like Robert, he fought against being feminized, but Aunty was shrewd, discovering that crisp, rustling taffeta held a subtle calming effect on Nancy. Consequently she ordered crisp taffeta uniforms for him to wear, as well as rustling petticoats.


When Robert's youngish Aunt made the pronouncement that she had every intention of curbing his boisterous and unruly ways by dressing him as her demure little ‘Niece', he created a considerable uproar, declaring that 'Never-never would he wear horrid girl's clothes’. Little did he realize the futility of denying the wishes of a determined female.


Aunty announced that she was so taken with Madame's idea of having Geraldine serve as a prim maid that she had decided to have her seamstress create a suitable costume for Roberta. "It would be delightful for my guests to be served by a prim boy-girl maid, darling!" Robert burst into anguished tears.


Through a door at the side of the room, a perfectly exquisite figure emerged. With the short blond curls, the large pearl earrings, the careful makeup, including carmined Cupid's bow lips, there was little to proclaim the figure to be that of her nephew. He made a beautiful spectacle as he minced daintily back and forth before us, lips held tightly together as if the lad was striving mightily to hold back his tears. Everyone clapped loudly, and all agreed that the ensemble was delightful.


Item #86a

Three stories of Robert’s introduction and debut in Petticoats with his Mother

By Nan Gilbert

Illustrated by BJ


Like my chums I took great pleasure in teasing the girls who lived in our neighborhood, sending them shrieking into their houses. I received many a scolding from Mother about this and the threat that, if I continued, she would invoke some dire punishment on me. Little did I dream of what it would be.


Miss Grace left the room for a moment or so and returned accompanied by two teen-aged girls dressed in keeping with ten-year-olds. Bobby glanced up, sniffed and turned his face away from them. He did not see the amused glance which they exchanged.


All the way to the Studio, Robert pleaded with his determined Mother not to compel him to become ‘Miss Dollie Dimples'.

"Really Robert, I simply cannot understand how you can be so ungrateful. Here I have spared not a penny to groom you for the role, ever since that day the talent scout spied you, and now you complain that you do not wish to be Miss Dottie Dimples!”

"But Mummy, I'm not a really truly girl! I want to wear trousers like other boys and have fun like they do!"


Item #86b

Four stories of Robert’s life in Petticoats with his Mother

By Nan Gilbert

Illustrated by BJ


“We are so fortunate, darling, that we decided to have two such adorable little girls! I shudder to think of what they would be like had we let them continue to wear trousers!"

"Yes, darling, we are, but I was more fortunate than you in that I entered Nancy in Miss Grace’s Seminary for conversation rather than trying to cope with his resentment over being frocked!"


As the trim figure of her smartly uniformed 'Maid' fussed with her hairdo, Roberta's Mother sighed as she remarked, "Really Roberta I am the most fortunate Mommy in all the world to have so adorable a son-daughter to look after her Mommy's every need." She smiled at him affectionately as she added, "You know that too, don't you my pet?"


"Roberta darling, are your undies as pretty as your frock?"

Roberta crimsons and lids his eyes, as his Mummy and her guest burst into peals of gay laughter.


"I judge from your phone call that you are seeking something 'special' for Master Robert?"

"Oh yes, Madame, my darling Robert is to accompany me to the gala opening of the Opera and I wish him to be costumed in a fashion which will create a stir among the other guests! I think you understand!”


Item #87

Four stories of Robert’s introduction to Petticoats by his Stepmother

By Nan Gilbert

Illustrated by BJ


Her preparations for his homecoming had been extensive. His room had been completely renovated; every trace of his fondest possessions packed in large cartons and placed in the attic. The furniture was removed and decorators summoned. The walls were papered with a quaint Goday print pattern with white framed Goday prints of ladies and children in elegant attire of the 70'e added for additional flair.


Robert watched nervously as Miss Strict gathered up his discarded clothes in a bundle and then stepped out of the room, tossing over her shoulder, "Remain where you are until I return with something more suitable for you to wear." She closed and locked the door behind her.


Robert whirled about, cheeks crimson, eyes blazing, "But... but... this... is... a... girl's room!" he managed to stammer, nearly choking on the words.

His cheeks paled at the glint which appeared in his Step-Mother's eyes, as she remarked, "Indeed it is dear, and quite suited to your New Life!" Her rippling laughter flowed about the room.


Item #88

Three Tidbits of Petticoats Punishment

By Nan Gilbert

Illustrated by BJ


A time passes and two crimson-cheeked, pretty little girls emerge from the cubicle, tears trickling down their cheeks. One is daintily dressed as a twelve-year-old in a pretty chiffon frock. The other lad is a picture of a prim little two-year-old Miss in a puff-sleeved petticoated frock that didn’t even cover his matching panties.


Little did I know what Fate held in store for me as we drew up before one of the many shops lining both sides of the street, this, obviously one which catered to girls judging from the array of dainty garments on display in the show window.


On mincing slowly into the presence of the Club members, a hush fell over the group a moment later to be replaced with a frenzy of excited voices all speaking at once. The Bride and his attendants minced daintily about the room before them while their eyes lit up with passionate gleams.


Items #90 and #90a


By Nan Gilbert

Illustrated by BJ

All the way to their destination, Susan chatted brightly about their excursion.

A smiling doorman in an elegant uniform held the door of the establishment open for them, slyly winking at Robert, bringing a flush to his cheeks. He found himself in the daintily-scented atmosphere of the salon. Casting furtive glances about him from under half-lidded eyes, he found some consolation as he spied sissily attired or frocked lads of varying ages, obviously all sharing his deep mortification, in the company of elegantly costumed ladies. Those in frocks appeared more forlorn.


Item #91


By Nan Gilbert

Illustrated by Juan

My item #4, TRANSFORMED by Nan Gilbert, tells the story of corporal punishment and bondage of a girl, Angela, as well as the petticoat punishment of a boy, Vernon . It ends as the boy becomes aware that he may be attending school 'Transformed'.

This was the first half of Nan Gilbert's story. The second half was never illustrated or published until now.

I obtained a 40 year old copy of the unpublished portion of the story and divided it into 48 chapters in the tradition of Nan Gilbert's work. Then I commissioned Juan to illustrate it in the style of the artist (Gene Bilbrew) who did the drawings for the first half of the story.

Here is a sample of the story and Juan's art.

"Look here, Verna, or whatever your name is, now you're here, you'll have to obey the rules. Any breach of rules upstairs means that all the girls on the landing are punished, and severely. Lucky for you it’s the first night of the term, and you're a new fish; otherwise you'd get it hot!"

Vernon shrank back still further at these harsh words. A tear started from one eye.

“Oh, goodness, a cry-baby!" said Eunice, a tall, pretty blond, well developed, and fifteen years of age. "What’s the matter?"

"I can't! I can't!" sobbed Vernon , "I've never done this before.”

Eunice turned to Molly. "Is he a boy?" she demanded. Molly nodded. 'That accounts for it!" She turned back to Vernon . "Whatever you are, whether a girl, a boy or a mermaid, you've simply got to obey. And don't forget, whatever you are actually, you're a girl officially, so keep your head. Now we'll have to deal with you ourselves. I'll take you and Denise can attend to Molly. Just watch how it’s done, and you'll know next time!"


Items #92a and 92b


By Nan Gilbert

Illustrated by ‘Unknown’

This is the earliest Nan Gilbert story I have found. The artist is unknown to me.

Edward, a thorough‑going lad of thirteen, finds himself in the home of Miss Strict, a spinster lady of middle age, a determined feminist who had small regard for anything masculine.

She had read a number of 'Letters to the Editor' in a well‑known Ladies Magazine about the reforming influence on over‑boisterous boyish spirits of employing ‘Petticoat and Pinafore’ discipline on the culprits. Yes, that is exactly what she would use in Edward's case. It would indeed be more pleasurable to have a demure, well‑mannered little boy‑girl mincing about in fluttering skirts than this utter monster of a boy!


    Edward stood stunned, a convulsive shudder passing over his frame, as he watched the maid place the corset on a chair and then unfold the vest in preparation to lowering it over his head. She took a step forward. Recovering from his state of shock, he backed away, thrusting out his arms in a protective gesture, his eyes blazing defiance, as he shouted, "Stay away from me! Don't you dare come closer! I won't wear girl's clothes! Do you hear! I won't wear girl's clothes!" He stamped his feet for emphasis.


    Miss Staylace spoke up, suggesting, "Please mince about the room for us, Miss Edwina, so we may be certain that your pettis have the proper sway and swish!"

    Covering his face in his hands he wept bitter tears, pleading, "Oh please, please, let me have my trousers back! I promise never to do anything to displease you again, only please let me have my trousers!”



    Item #93


    By Nan Gilbert

    Illustrated by Juan

    David, a star athlete, decided he would try to earn some extra spending money by taking a job for the summer months. He went from establishment to establishment without any success, becoming despondent that he would not find one, that is until he overheard one of his Mother's tea guests remark that La Cissy Boutique was looking for a delivery boy and having great difficulty in finding one, as most boys shunned the idea of being seen carrying their parcels.


    Item #94


    By Nan Gilbert

    Illustrated by Juan

    "Oh please, Aunty, don't let anyone see me like this."

    "Nonsense, Leslie, you should be very proud of your pretties! Come along now and no nonsense!"

    When Leslie spied Percy and his Mummy, he tried to flee to the sanctuary of his room; but Aunty was prepared for just such an event, and held him with a painfully tight grip on his arm.

    It was Percy who spoke first, pointing a derisive finger at Leslie, exclaiming, "Oh look Mummy, Leslie is wearing a dress!"

    Leslie blushed bright red and kept his eyes glued to the floor. “It’s just was so unfair,” he thought, “Percy was the cissy. He should be the one in a dress, not me!”  




    Item #95


    By Nan Gilbert

    Illustrated by Juan

    On the third day after his return home, he found his sister studying him at the dinner table, a coy smile playing about her lips. It was frightfully disconcerting. Finally she remarked, “Mummy, you know I think Paul would look awfully cute dressed as little girl!"

    Paul held his breath waiting for her reply.

    “Perhaps dear… At least it would do no harm to try!”


    Item #96


    By Nan Gilbert

    illustrated by BJ

    "Let me help you out of your lovely coat, Miss Roberta!" Robert shrank back as she reached out to unfasten the large, baby-blue pearl buttons, bringing the exclamation from Susan, "She really is terribly shy, isn't she?"

    Shortly the coat was hanging by a satin hanger on a rack and the streamers of his bonnet being loosened. The moment of discovery had arrived! Robert knew that Susan would learn of his deception the moment she spied his boyishly cut hair. Tears of anguish filled his eyes as the bonnet was slipped from his head. He heard Susan gasp in amazement.


    Item #97

    MONSIEUR VENUS! Part 1 & 2

    By Nan Gilbert

    Illustrated by BJ

    Deeply chagrined, Robert pointed a trembling finger at the dainty garments, crying out in dismay, "You... you... mean… you... you... expect me to... to wear those things. They're girl's clothes!" His voice shook.

    "Yes Robert, they are! You see, I am going to transform you into my charming little Daughter!" She burst into gay laughter over his dismay.

    "But... but… I'm… a boy! I couldn't be your... your… Daughter!”

    "Nevertheless you will be, and you will look so sweet fluttering about in frilly undies and pretty frocks!"

    Robert's cheeks flushed with anger, his eyes glittered with rebellion as he shouted, "I won't wear them! Do you hear me? I won't wear dreadful girl's clothes!


    Poor Robert's nerves were atwitter as he was presented to a number of the ladies, their remarks about his charming appearance and being introduced to their nervous charges. He couldn't be positive about several of the daintily dressed figures, as they appeared to be quite self assured, as one would expect genuine girls to be. The others, from their sheepish expressions and obvious agitation being petticoated boys like himself.


    Item #98


    By Nan Gilbert

    Illustrated by BJ

    Dennis, a fourteen year old boy, now Denise, prettily frocked as a ten-year-old, has received a letter from his Pen Pal, Peter, with whom he has been carrying on an exchange of ideas dear to the heart of thorough-going boys for over a year

    "Peter is asking if he may come and spend a week with me during the summer Holidays!"

    "How nice!"

    "But Mom, what would he think seeing me in frocks?"

    "You mean you didn't tell him that you no longer wore trousers?"

    Lidding his eyes sheepishly, his cheeks darkening, Denise confessed, "No, Mom, 'cause I was afraid he wouldn't want to write to me anymore!"


    Items #99a, #99b and #99c


    By Nan Gilbert

    Illustrated by Juan

    Aunt Agatha burst into peals of gay laughter at my expression as the terrible truth dawned on me. "You... you... mean..." I stammered in shocked tones.

    "Yes, Paul, during your stay with me you will be addressed as Miss Pauline by the servants and of course dressed fittingly!” There was a finality in her tone, which left no doubt that she was perfectly capable of carrying out this awesome threat.

    Every boyish instinct cried out as I leapt from my chair, shouting, "Oh no you won't! I won't have it! I won't have it! Do you hear!" I'm leaving this hateful house this minute!"


    From under half lidded eyes I saw Suzette mincing over to the wardrobe, tossing over her shoulder, "You will be quite thrilled, Miss Pauline, when you see the adorable petticoats you are to wear!"

    Suzette emerged, shaking out imaginary wrinkles in the petticoats I was to submit to, layers of crisp, glistening, swishy taffeta with stiffened net between, all daintily frilled with oodles of lace and ribbon-bow frills. I closed my eyes to blot out the hateful garment, yet the frou-frou beat thunderously on my ear drums.

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