The Art of Petticoat Punishment

by Carole Jean

Part 4.7 - Nan Gilbert Letters

I have several old letters from 'Nan Gilbert' to her friends. If you have any others or any additional information about any Petticoat Punishment authors or artists, please contact me.

Dear Evelyn,

My, what a pretty name you have. "Thanks heaps for your very lovely letter in response to my ad in New Trenns, and thanks SO much for the vital statistics, although, myself, I am a devotee of the conception that one is only as old as one feels.

We do indeed, have a common basis for a delightful exchange. The frills and furbelows of dainty girl's attire have always fascinated me. Girls are truly to be envied the privilege of being free to wear them. Perhaps I was more fortunate during my childhood years, as my Mother delighted in dressing me as her little Daughter. Perhaps due to the fact that she lost her first-born, a girl, shortly after birth, and later having a son, I more or less took the place of her lost child. I was dressed and reared as a girl until I was six, when I had my first trousers to go to school. From then until I was twelve, I had a lovely ward-robe to wear in the privacy of the home. It was as though I were two distinct personalities- one the one hand, a thorough-going boy enjoying the rough games boys engage in, on the other a demure little Miss playing with several little neighborhood girls at their simple pursuits. Perhaps of interest, I was never teased by my boy chums, and woe to the very few who tried this, as they were shortly taught a proper lesson. Likewise, the girls accepted me as one of themselves, the fact that I was a boy, having a singular appeal to them.

Contrarywise, it was my Father who subjected me to the so-called 'Petticoat Discipline'. I should add here, that as his business ventures kept him away from home for long periods, he knew nothing of my wearing dresses at home. Strangely, perhaps, I detested wearing the girl's s clothes he purchased, as they were of the plainest nature, and further, I would receive chastisements, when so dressed.

I also made an observation which could have influenced my thinking. When dressed in my pretties, my Mother's tea guests made a great fuss over me, cuddling me in their arms and telling me what a sweet child I was. Some, even daring, although surreptitiously of course, slyly putting their hand up under my little skirts to fondle my 'thing' thorough my drawers, something which I found most exciting. Contrarywise, if they were present, when I came in from play, they gave me short shift. It left me with the thought that perhaps it was nicer to be a girl than a boy.

It was during my earliest years that I developed a lifelong fetish for taffeta, which was very fashionable at the time. The crispness of the material, combined with the sibilant rustling held an overpowering appeal for me. At every opportunity, I would dress up in one of my Mother's taffeta petticoats, and parade about in ecstasy in the garment. My Mother even had taffeta petticoats made for me by her seamstress, cementing the fetish even more solidly. It has never waned, although today it is nigh impossible to find this fascinating material. Although I never received any instruction in sewing, I have discovered that I have a natural adeptness for the needle and sewing machine, and so am able to fashion my own garments, particularly undies from taffeta. As I remarked, its fascination has never waned.

When I reached the age of twelve, my Mother 'orbit me wearing my beloved pretties; but, as in your own case, I would dress-up in my Mother's clothes, or those of a girl cousin who came to live with us, and who, strangely enough had a flair for taffeta.

A little incident which left me almost heart-broken is worthy of mentioning. In rummaging through the attic, I came on an old trunk filled to the brim with Mother's s discarded garments. The particular one which took my fancy was the lace skirt over taffeta of an old evening gown. Oh the hours of ecstasy 1 enjoyed, parading about the attic in that skirt. One afternoon I was seated with Mother on the porch of our Summer home, when out stepped my Cousin wearing that petticoat, which she had converted into a modish skirt. I fought back the desire to upbraid her for interfering with my pleasure; but how I hated her for ruining (in my mind) my beloved petticoat. Oh yes, I availed myself of every opportunity to wear it; but it was never quite the same for me.

I,too, enjoy fantasies where I am taken in hand by a strong-willed female, stripped of my attire, laced down into a wasp-waisted corset, and. dressed in all the frills of a little girl, and forced to lead a girl's life. Over the years, 1 have written reams on the subject, all with the same basic theme, forced to become a girl; yet secretly enjoying every moment of it. I believe it is referred to s a 'guilt complex', natural instincts struggling with subconscious desires. As a male, I am all male, enjoying all forms of sport, hunting, fishing etc. Contrarywise, when I dress in feminine finery, I am quite as thorough a female. It is one of life's inexplicables.

My wardrobe for the most part consists of cute party dresses, suited to a fastidious little Miss of ten, along with taffeta undies which I fashion myself. I may also be an adult when the urge takes that direction. 1 detest housework, yet each Saturday morning, I become a prim maid in a smart black taffeta uniform, cap and apron made by myself, and go about cleaning and tidying my apartment with complete enjoyment.

Your mention of 'Petticoat Tales' booklets was most thoughtful. However, I must confess with a little pride that I authored the, now famous, GILBERT series- "Adventures In Petticoats"- "Memoirs In A Pink Mirror"- "Transformed" etc., for which I did the text, and another chap drew the illustrations. You have no idea what pleasure I derived in doing this. Of all the tales, the only one which I know of which is complete-i.e. 48 Chapters- is Adventures in Petticoats. The others are only parts of the original, fragmentary at that, some with one or two of the original illustrations; but most with more recent ones. Unfortunately, most of the longer tales I authored I have given away to friends; but I still have a few, as well as a number authored by a dear friend who lives in Canada, and shares my adoration for pushing back the years to become a cute 'Little Girl' again. 1 shall be delighted to loan you what I still possess, if you are interested.

Have you ever tried putting down on paper your TV thoughts? If not, you should try. I have found that what appears to delight most of my readers is my style of making the reader ‘live' every situation. I do have to confess that once I have completed a tale, I rarely ever read it over again. My pleasure came for writing it.

It was most thoughtful and considerate of you to enclose a snap, and may I flatter you by remarking that you do make a very vivacious, charming Demoiselle. So many are unable to achieve femininity, despite all the cosmetics, and lovely apparel they may wear. After all, one is what one is, and natural feminine charm must be present in one's personality. I truly appreciate the confidence you have shown in me, by sending me the photograph. I reciprocate with every wish for a long and mutually delightful exchange.

You are so correct when you remark that so very, very few of the 'Sisters' displayed TV tendencies in childhood. It is most rewarding to discover one whose thoughts so closely intertwine with my own. '

Do write soon.



P.S. A little confidence. I used the femme name of 'NANCY' for many years, then foolishly thinking I could 'Go into the closet', soon after I emerged as Jane. One could, perhaps, declare- "Once a TV, always a TV."

Finally, here is a letter from 'Posey' about one of his visits with 'Nan'. I apologize for the poor quality of the photos. They are copies of copies.

New England and New York Trips

From time to time I have described to some of my pen pals my visits to New York, where I would meet different pen pals, and also visits to surrounding places, especially to visit my friend Nan Gilbert. He was the writer of famous petticoat discipline tales, which are sold all over the world, and needless to say Nan Gilbert was NOT his real name.

In my letters I would explain, especially for British pen pals the layout of New York City, etc., but will leave these parts out in this short account. I am mainly concerned to describe here visits to New York City to three of my pen pals. One came up from Camden, N. J. to see me; a second lived in a New York studio, and the third was Nan Gilbert who lived in Greenwich, Conn.

After writing these three pen pals for some time, there was a suggestion by each of them that I should visit them, but especially Nan Gilbert made the suggestion and offered the hospitality of his home. About this time my wife, who was an invalid suggested that I should get away, while she went to her home to be with her sister. I suggested that I visit this friend in Connecticut, but also visit New York, so was set a pattern which continued for about nine years until Nan Gilbert's sudden death. I would make arrangements beforehand for my Camden pen pal to come to New York City before I was to go out to Greenwich, Conn. And also arrangements to meet with two other pen pals whom I had in the City.

I have omitted Posey's description of his visit with two New York friends.

It is now time to leave New York City and visit my friend Nan Gilbert, in Greenwich, Conn. That is not his real name, of course, but for convenience I shall just call him Nan. I visited my pen pal and friend some nine years in succession, and he visited me once here in Halifax.

Before I tell something about my various visits, perhaps I should relate how I got in touch with him. Like all of us who have special interests, I had been seeking others with kindred interests, and at the time we had a special tabloid here in Canada, which filled the centre two pages with special ads of people in the States and Canada and elsewhere. It was called JUSTICE WEEKLY, and I too ran an ad mentioning my special interests. (Since then the paper has folded, due to the Editor getting too old, and not being able to get anyone to buy it over).

At the time I was not into infantilism and rubber as much, so I did not advertise those areas in my ad; more just little girl transvestism, the use of the kilt and petticoat discipline. After a while I received an answer from an old gentleman in Sarnia, Ont., who was well in his eighties. He had been a T. V. all his life and still liked to dress up, being a charter member of TRANSVESTIA, the big publication in the States.

He said in his letter he did not know if I would want to keep writing him, but there was something in my ad which interested him. That was the fact that I said I had a special kind of transvestism, that is dressing a young girl, and he knew only one other, a pen pal of his, who had similar tastes. Would I give him permission to give him (his pen pal) my address, if I wrote him (my replier) back? He also would ask his pen pal in the States for permission to give his address (his pen-pal in the States. The long and short of it was that after a while I received my first letter from Nan Gilbert (his nom de plume he wrote under) and that was the beginning of a wonderful friendship and a correspondence which lasted many years.

This, then, was Nan Gilbert, writing me before I could write him, and he was just what the doctors ordered, as they say. He liked to dress as a young girl, had been petticoat punished as a boy, liked to make his own clothes, especially taffeta underwear. He was a writer of stories, petticoat discipline tales which were very successful, so much so, that most of them were pirated and are still being punished, even though he has been dead now for over six years.

Doctor Cauldwell wrote a book on Transvestism and there is one chapter in it about Nan Gilbert. He it was who got me interested in writing stories too. He was interested in my own interest in the effeminisation of the Kilt which was new to him, never having worn one, being of German extraction, a third generation American.

Anyway, I replied to his letter and we started an exchange which lasted many years until his death. We were compatible in every way from the beginning, and gradually we revealed more and more of each other. We got to writing each other practically every week and never seemed to run out of material or things to say to each other.

When it was time to visit my friend in Greenwich, I just went down from the hotel to the Grand Central Station below, which used to be a meeting place of N. Y. in the days when the railroad was king. The main Concourse in itself is a wonder to see, and today, I believe, is almost deserted as so few people use the train. I would take the New Haven line, a commuter train which went along the coast of Connecticut where it meets New York, and commutes people from Rye, Greenwich, Stamford, and other places. It was only a half hour even with stops.

I have omitted a section in which Posey gets too detailed about Nan’s family

As for his special dressing up interest, none knew of it, except those to whom he wished to reveal it. He had a lovely apartment, consisting of a master bedroom, living room, dining-room area, kitchen and bathroom. I slept on a couch, really a daybed. Our routine was roughly as follows. We had a leisurely breakfast first in the apartment, dressed in some frivolous nightie and peignoir. Then tidy up, shave and get dressed. We would take the car and go for his mail and shopping, then for a drive to see the surrounding country or to his yacht or golf club for a light lunch, or to a restaurant. Then back to his apartment to have a rest or he would show me his manuscripts or special sketches, photos, etc.

We would then dress up properly and he would take me to rather expensive and famous restaurants, Red Barn, etc. One, I remember was visited by famous actors and other celebrities from New York. He would take a different one each evening, and the meals were very expensive, but extremely good! He would not hear of me taking my turn, and the only way I could repay him was when he visited me in turn in Halifax. He was a most generous man.

We would then go back to his apartment and the rest of the evening would be taken up with dressing up and taking all kinds of photos. I have gathered many of them together of the two of us dressed up as young girls, etc., for each year I went down he had a new supply of dainty undies and dresses that he had made (the former) or bought (the latter). He had the catalogues of all mail order firms. Many of these he would give me to take back to Canada, and it would be easy to get them through Customs by calling them second hand clothes for a niece.

I have said that he was a TV first and foremost, but of a kind of which there are only a few, namely that he liked to dress up as a young teenage girl, and even for a male he made a convincing girl, as can be seen by some of the photos of him on the succeeding pages. There would be dresses he had bought from mail order houses, size 14X, which fitted me without alteration, although he was an expert sewer and would alter anything that did not fit. He owned a sewing machine. There would be taffeta (of which he was very fond) undies with lace trim, etc. Once he made me taffeta long old-fashioned pantalettes with frills of lace and net down the legs.

He loved to buy frilly petticoats, both half ones and princess style, hanging from the shoulders. Then he would buy all the accessories, stockings, garter belts, pantie girdles, dainty vests, shoes, little purses, gloves, long and short, wigs, hats, everything that a young girl would need! It is possible to see some of these accessories in the photos.

All these items he freely loaded me with each trip, and, as I was like him, a closet dresser, it would be an embarrassment to me to take them, as I knew I would never use half of them, except for an occasional photograph. Hop himself had a long locked cupboard just full of clothes, adult as well as juvenile, even a wedding dress and all accessories. Yet I know he never dressed up to go out.

Anyway we delighted to dress up in different outfits, and take each other's photo, or using his timer we would be taken together. He had two or three cameras. He might dress up as a maid and I as a girl and we would be taken together. Perhaps this is as good a place to comment upon the photos shown here.

The first one shows Nan in petticoat and lace-trimmed drawers, little girl socks and slippers. He had several wigs and wears a blond one, shoulder length and fringe over brow - a typical little girl hair-do.

This photo is of yours truly, in a pink dress for a young teenager with matching hat, gloves, purse knee socks, and slippers. We just loved dressing up in these outfits and having our photos taken!

Next is a photo of the two of us taken with a timer. It shows me in. a green dress, brown wig, knee socks and slippers and Nan dressed in her maid's outfit, kneeling measuring the hem of my dress. Some of the dresses were a little old, and in the meantime the hems of girls' dresses had risen and Nan was about to shorten the hem of this green dress.

This is a rather quaint outfit on me, a pink dress, matching wide-brimmed hat, fur-cape, gloves, etc.

These two are of Nan. In one he wears a blue dress, which he holds up to show his petticoat, and he wears a matching blue bow in his hair (a brown wig.)

In the other he wears a pink voile dress with matching hat, gloves and purse. In all of them we try to look as young girlish as possible.

Here is a very girlish photo of Nan. He wears a blue dress with matching bow, Nan over it a little girl pinafore. He was very fond of pinafores, which he made himself, of course. The wig compliments his face, and he made a cute young girl! He gave me several of these old-fashioned pinafores.

This shows the two of us as little girls, I seated with a doll in my arms, and Nan bending over me. I wear a pink dress with petticoats and frilled knickers beneath, and a dainty pinafore. I have a platinum wig this time and hold a doll. Nan wore a blue velvet dress with delicate lace trim, over petticoats and also a dainty pinafore. We both wore bows in our hair (wings).

These next two photos are of me: The first showing me wearing a simple tennis frock and matching panties. I am wearing the platinum wig.

The second photo is one of my favorites, showing me wearing a little girl's brown dress in flowered pattern. I wear it over petticoats and taffeta pantalettes in pink with rows of net. I have all the accessories a little girl would have - purse, gloves hat, etc.

Nan appears again in his blue velvet dress, which was his favorite one. This time he has a white bow in his hair.

This shows me dressed in just diaper and rubber pants and nursery bib, with bow in my blond wig, seated at the breakfast table. It was very warm that day hence the wearing of clothes was at a minimum. When Nan knew of my interest in rubber and infantilism, he surprised me one visit by having ready for me diapers, baby pants, bibs, pacifier, baby bottle, etc. That showed his generous nature once again.

This photo is my favorite, showing me in a blouse, little kilt, worn over petticoats and lace-trimmed knickers, gloves and blond wig and holding a doll. Again, when Nan knew I was coming he had got a kilt for me, not a real one, of course, but a girl's one. I enjoyed the outfit as in photo, especially with diaper and rubber pants inside my taffeta lace-trimmed knickers!

These four photos all of the two of us taken together. The first two show Nan as my maid dressing me! Nan is seen lacing me into a corset, while below it I wear rubber lined panties. Nan is in her full maid's costume.

Below is Nan now helping me on with a pink taffeta and net trimmed petticoat. I already have on the matching pink taffeta net trimmed knickers. Nan made both the petticoat and knickers.

The next was one of our favorites. Again showing Nan in her bestest velvet dress and voile pinafore, and me in my bestest pink dress and similar voile pinafore.

The last one shows us playing with our dolls! Nan is in his pale blue dress with white lace trim and I am in my pink dress with white lace trim. Nan has on matching stockings. This time I am wearing a lovely brunette wig.

I have taken quite a bit of space to show these photos of the two of us, as I should imagine they were somewhat unique sessions, and such would not very often be repeated. After our dressing up sessions and taking photos, we would sit around in our favorite costumes for the rest of the evenings, talking, showing pictures, watching T.V. and reading his stories and looking at the many sketches he had commissioned by a friend - mostly of a petticoat discipline nature.

It was summertime and the apartment was air-conditioned, so it was pleasant with cooling drinks. Then about twelve we would retire. I must say he was strictly heterosexual; had been a leader of boys for all his life, and I am sure there were no other sexual tendencies in him. I would call him a special kind of Transvestite - what I would call a juvenile TV, a perpetual youngster, a Peter Pan, a boy who would not grow up, but one who liked wearing dresses and petticoats and a fantasy from his childhood, of being petticoat disciplined, which had happened to him, as he told me.

The four or five days I spent with him were carried on this way, but varied by trips to big department stores to see the girls' departments, and there I had to prevent him buying me anything in the way of dresses, etc that I might like! Or we would go sailing with his nephew who owned a lovely yacht. But our routine re meals never varied - breakfast in the apartment; a light lunch at a pancake house or restaurant, then a big dinner at a more prestigious hotel or restaurant.

When I got back home he would send me prints and negatives - he always got two negatives made up of all the photos that we took. Sometimes we would work out the plot of a story together. The reader will gather that he was a most generous man, and it did not stop with entertaining me most royally, making and giving me clothes and photos, etc., but one trip he noticed my suitcase was rather shabby, so he produced a lovely traveling case - air luggage - and presented it to me, saying he had no use for it, as his traveling days were done, but I suspect he bought it new, for it did not have a scratch on it.

Another time he gave me an expensive Polaroid camera - the one I still use. However, in this case I think he was changing cameras and it was his old one, but still I could not have afforded it, for it cost then about $200.00. It has case, electronic flash, and timer. And with it he gave me a Kali Copier and light to copy my own Polaroid pictures. This was a Japanese instrument, and has proved very handy.

I think he delighted in doing things for others. Once he gave me a change purse, the kind with rim on it, then said I would need a lucky coin for the inner pocket, so he got out a cigar box full of gold coins and chose a golden Eagle with the year of my graduation! I still have it, and could sell it for $600.00, but naturally will never part with it.

Just before he broke up housekeeping and moved to Beverly, Boston with his daughter, when he knew his eyesight was going, he sent me a first edition of complete works of Walter Scott. It is a numbered edition and a collector's item. So the reader will see that we have been good friends through the years. As I said, he visited me once in Halifax, where I went to live after my wife died, and I tried to give me a good time, but could never have repaid him for all his kindnesses to me.

When I was ready to leave Nan would drive me to Stamford Junction and I would get the express to Boston. We would go through Providence, R. I., and just around the corner from North Station, Boston, was the Bus Depot where I got an express bus to Bangor, Maine, where I would pick up my car, and drive the 400 miles to N. B., arriving home about 2 a.m.

I have tried in this little account to relive what it was like to visit a pen pal whom I had been writing constantly for years. It was like coming home to arrive in Greenwich, which, by the way, is one of the most beautiful and clean towns in New England. We confessed to each other our feelings the first time we met at Greenwich Station. I said I would have stayed on the train if I had not liked the look of things, and he confessed that if when I got off the train he had not liked the look of me, he would have slipped quietly away!