Letter 5
A Sissy Boy's First Petticoating
from Sissy Toby 

Dear Susan,

For a long time, as a boy, I was very confused as to 'who or what am I?' When perhaps 13 or 14, I wondered if I were gay. In those days (1960's) they were known as 'queers', a term I now find disgusting. Well, it finally dawned on me that, since I prefer the company of girls, and day dream about girls, I was not gay. So, then, what was I?

My discoveries at that time: I am a very gentle boy who prefers the company of girls over the company of rough-acting boys. I also learned that I adore wearing girls' clothes, and acting like girls.

I was raised out in the country, but not on a farm. Many of the girls I knew were tomboys. (I liked the story in your Summer 2003 issue, 'A Willing and Docile Janegirl' by Patricia S. That story has a lot of truth in it).

I am not a transvestite who wants to feel like a female, nor a transsexual, who will have operations or take hormones to become female. I am a janegirl, a male who enjoys being a feminine boy. I was always gentle and meek but, after some petticoat discipline, I am now a very prissy sissy. This discipline did not change who I really am, but rather it pointed me toward the 'real me'. If not for the years of 'training to be macho' that society dumps on we boys, many of us would be, quite naturally, very prissy boys.

Of course, in the beginning, while undergoing petticoat discipline, I was very rebellious and tried to fight it. But, after only a very short time in silky panties and pretty dresses, I learned that this is who I really am: a prissy girly boy, who now openly admits to being a sissy. I love being a sissy Janegirl, and would not change that for anything.

I will explain to you how I came to be petticoated, and I am sure that readers will understand why I like being as I am.

I have always, as I explained, been a very mild meek individual. While growing up in the country in North Carolina, my best friends were all girls. Oh, I got along alright with the boys, I just didn't care about playing ball or hunting and such. The boys all liked to play rough and talk vulgar, but while in the company of girls, I felt that I fitted in perfectly.

It was the 1960's. My best friend was Marie, who was my age; 16. She had two younger sisters, Carol and Ruth. Usually with her were her friends Barbara and Iris. Marie and her sisters lived in a small house on the bank of Lake Wylee. I enjoyed walking to her house, just to spend the time of day with her. I always felt relaxed, and could be so open and honest with her. It was not like talking to boys at all. They always had to exaggerate everything to try and be big shots.

Marie was very grown-up for her age of 16. Her mother had passed away from cancer a year earlier, leaving her to be the 'Lady of the House'. Her father was seldom home, either working or on fishing trips. Her grandmother would visit from time to time to check up on the girls. Otherwise, they were very much on their own.

One day I was visiting Marie. She and her sisters were busy cleaning their house, so I pitched in to help. About that time, their grandma stopped by for a check on the girls. When she found me in the house, she was at first upset with Marie.

'Have I not made it clear - no boys in the house?' she asked. All three girls spoke at once. 'Toby is not like the other boys. Toby is more like a girl than a boy. Toby is our best friend'.

Grandma stood silently, considering what she had just heard. As all three had told the same story simultaneously, then the boy must be a sissy janegirl, I suppose she thought. I am sure that there were plenty of sissies around in her day, wearing velvet Little Lord Fauntleroy suits with lacy collars. So, then and there, Grandma made a decision.

'If you want Toby to be allowed to visit, then Toby will have to become exactly what you said he is ... one of the girls. Toby, will you agree to be a girl every time you visit my granddaughters?'

I thought for a minute. I would hate more than anything to give up visiting my very best friends. 'Yes, Ma'am. They can call me a girl if they want to'. I had no idea what was to come next.

'Very well then. Marie, Carol, and Ruth, go find Sissy some suitable clothes to wear. She will dress in the prissiest girly clothes you can find. I want to make sure that you girls are safe, otherwise I will have failed in my duty as a grandmother. And don't forget, from now on, her name is 'Sissy'. Hurry along now'.

The three girls were all grins and giggles as they vigorously sought out the sissiest clothes they could find. They brought out a pale yellow dress and a hot pink sash. 'Very good choice', spoke Grandma, 'but we will need shoes and some hose, and of course some panties'.

The house was filled with laughter as the girls rushed about finding these items. Meanwhile, I was standing there in a state of dull shock. Grandma told me to strip down to my underwear. My face turned beet red as I obeyed the older woman. Now the house became chaotic with loud laughter when the girls came back into the living room to find me standing with my hands behind my back in only my white jockey shorts. Tears were now rolling down my red face.

'Now, go in to the laundry and slip on Marie's pretty pink panties,' said Grandma firmly. Carol, who was 14, smiled with delight. Ruth, who was only ten, clapped her hands gleefully.

Marie fussed with the pink panties and made sure they were straight and fitted properly. Next came my hose, with a garter belt. I was already enjoying the feel of silky panties and nylons. The shoes were actually strap sandals which were a bit too tight.

'You girls will have to find your pansy girlfriend some shoes for her next visit. Now the petticoat and dress'. Finally, Marie slipped the dress over my head. The look on my face told everyone that I loved it.

The pale yellow dress flared out naturally, and only came half way down my thighs, leaving my pink panties clearly visible for all to see. Next came the hot-pink sash, which was really a very big pink ribbon which was tied around my waist and into a big bow at my back.

Grandma approved of my new sissy clothes. 'I had best not catch you here with my granddaughters not dressed like a proper girl. I have to go now. But, I want you girls to apply a little lipstick and make-up to Sissy. He should always be the prissiest girl in this house. Oh, and if you go out, Sissy is not to change clothes! Not until she is ready to go home. Is that clear?

'Yes Ma'am!' exclaimed all the girls at once. They went to work on my nails immediately. Then they did my lips and applied a gentle pat and powder of make-up. Next they lightly dabbed on a very sweet perfume. Grandma was gone only a few minutes when Barbara and Iris showed up. They are both the same age as Marie and myself, but it took them a moment to recognize me. Then came the hoots and laughing. 'Show Barbara and Iris your panties, Sissy', insisted Marie, even though my panties were clearly visible with so short a dress, I was made to reluctantly lift up my dress.

'Let's take a walk up to the store for some chips and soda', suggested Iris. All the girls agreed. I was terrified of leaving the house and tried to refuse. But not only were the girls able to physically overpower me, but their will was simply stronger than mine. So, I gave in and we went outside.

Everything was so different while dressed in very fussy girls' clothes. The breeze caressed my nylon stockinged thighs. I loved it! We passed by several houses, some of which where people were out in their yards. I got some curious looks, but nothing more.

When we got to the store, I was more afraid than ever, but I would not dare to make a scene, so I walked in with my girlfriends. The lady behind the counter recognized me at once and laughed out loud. There was at least nine or ten customers in the store, all staring at me. One of them knew me - she was a year older than Marie and myself. Her name was Bunny.

'I am sure you know that everyone at school will soon know that you are a sissy?'

My face turned red, but I could not answer her. Little Ruth spoke up for me. 'Her name is Sissy now, and she loves being a sissy. She is our sissy and we like her this way'.

Bunny just looked at Ruth, and then at me, and smiled. 'I guess if you like being a sissy, then that is alright with me. But, you need to know, that name is going to stick at school'.

She was right of course. For a short time at school, I was ribbed and ridiculed, mostly by the boys. But I got on well with most of them, and in time they accepted me just as they did before. And little Ruth was right. I love being a sissy – and, what's more, 'Petticoat Discipline Quarterly' is by far my favorite site on the internet.
Thank you, Nanny Susan,

~Sissy Toby~

P.S. My two greatest loves are soft female domination, and dinosaurs. My mistress, who is also a big fan of your site, also allows me to indulge in my love of dinosaurs,with books, toys, and very elaborate dinosaur art. I also have a teddy bear, a boy baby doll (which I keep dressed in little girls' clothes), and a Strawberry Shortcake rag dolly.

I would like to take this time to thank you for all the wonderful letters and very helpful information. I wish that more dominant women who would read PDQ and learn from you that whips are not necessary to have total control of their men and boys. Petticoats and nappies are much more effective, and much more loving.
S. T.

Toby has been one of PDQ's most devoted readers since its earliest days. I am happy that he has at last put pen to paper (so to speak) and given us this description of his earlier years. As somebody who was a 'janegirl' from his earliest years, he is lucky to find a partner who is also in agreement with the techniques promoted by 'Petticoat Discipline Quarterly.'
Susan

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Letter 6