from Cheryl

Dear Helga,

As I mentioned in my earlier letter, in my work as a salewoman in the women's and girl's clothes department of a large department store, it does seem as if, while still not an every day kind of thing, it is becoming more common to have customers who are women who are buying girls clothes to petticoat their sons. In fact, I've had a couple of really interesting instances just in the past two weeks.

The first involves what I'll call a case of "woke" petticoating. One afternoon a couple of weeks ago I saw a couple of women shopping in the girls clothes section with what turned out to be their seven-year-old son. When I helped them, I learned that the women were married to each other, and they were very progressive in terms of their views on gender and gender identity, and it had been their goal to raise their son Dana (a name they said they chose because it was gender ambiguous) in a "gender open" way. So, instead of referring to Dana as "he", they called Dana "they", and had tried to avoid encouraging Dana to be at all boyish. In fact, when I first saw them shopping, I thought Dana was a girl (I'll call Dana "he" only because using "they" can get confusing). Dana had long, fairly girlish hair, and although it wasn't in a pony tail or braids or anything like that, it was cut into a girlish style. And his clothes were sort of, but not completely, girlish: regular running shoes, but with pink socks, some blue shorts that were more girlish than boyish in style, and a pink pullover top. I only learned that Dana was really a boy when one of his moms told me that Dana was "boy bodied" (that's the term they used instead of calling him a boy).

Anyway, what the two moms also told me was that they wanted Dana to experience the whole "spectrum" of gender identities so that Dana could eventually decide for himself on his gender. But what maybe was most interesting about this is that the moms had been homeschooling Dana, but had very recently enrolled him in a very small, private, very progressive, school, where the philosophy of the school matched their views on gender. What that meant, in part, was that all of the "boy bodied" students were taught that anything masculine or boyish is bad, and had to spend half of each month wearing the kinds of clothes that we generally think of as girls clothes. And so, the three of them were shopping for some appropriate clothes for him for school: panties, skirts, blouses, dresses, and girl's sweaters. A bit surprisingly, I think, Dana wasn't too pleased with this, and a couple of times said that he would rather wear boys clothes and that he was a boy, not a girl. Needless to say, Dana's moms were pretty direct in admonishing him when he said that. They rather sternly reminded him that "There's no such thing as boys and girls. There's just some people who are more boyish and some who are more girlish, and he might end up as either one or somewhere in the middle." But they also made it very clear to him that he would be leaving the store wearing some of the clothes they were buying and would be wearing those clothes to school that week. When they left, Dana was wearing some new panties, pink tights, a red skirt, and a very frilly white blouse that buttoned up in back, and had a pink ribbon in his hair. In other words, he then looked completely like a girl.

Then, just yesterday, I had a pretty interesting petticoat discipline customer, which is what reminded me to write to you again. The woman was a very petite, gray-haired, attractive in a school marmish sort of way, older lady who was shopping with her ten-year-old grandson. He was bigger than his grandmother, but was obviously almost terrified of disobeying her, and she was intent on using petticoat discipline on him. When I first went over to help them, she was firmly holding one of his hands in hers while looking through panties with the other, and he was just standing there with his head hanging down and eyes lidded, looking almost as if he was about to cry and his eyes were red as if he actually had been crying within the past few minutes.

Because this happened so recently, I can remember almost all of our exact conversation as I helped them, so maybe I can describe what happened in that way.

"Can I help you?" I asked.

The woman smiled at me, and looked at her grandson and squeezed his hand more tightly. "Tell the nice saleswoman why we're here, Ryan" she said.

The poor boy could barely look at me he was so embarrassed. "Tell her" his grandmother said, rather sternly this time.

"We're ... buying girls clothes for me" he finally said in a very soft voice.

"And tell her why we're doing that" his grandmother said.

"Because I'm, uh, I'm being punished for not doing my chores and for trying to bully my younger sister into doing some of my chores for me."

Then, with some tears starting to actually form in his eyes, he turned to his grandmother and said "Please, grams. Please. I've learned my lesson. Really I have. Please don't make me wear panties. Please."

Ryan's grandmother seemed intent on making the whole experience as shameful as possible for him and when he said this her reply was to look at me and laugh and then she said "Ryan! if you think that there is any chance that you are going to get away without being put into panties, you're sadly mistaken. And not just panties. I guess you don't get it yet. With this nice woman's help, I'm going to pick out a pretty dress for you to wear too, and you're going to wear it home. So now then. Are you going to give me any more trouble, or are you going to be a good boy and wear the pretty clothes that I tell you to wear?"

Ryan looked completely dejected and defeated, and quietly said that he would be a good boy for her. I was just standing there while all this took place, with astonishment at how controlling this small older woman could be with her grandson. I then helped them figure out the right size panties for him and brought them a sampling of different colors and kinds, and the grandmother made Ryan himself pick out six pairs, after holding each pair up against him and commenting on how they would look and feel when he wore them. We then went into a changing room and I brought them a variety of dresses for Ryan to try on, and after his grandmother had selected two of them (and picked one of those, a very pretty and certainly very feminine yellow and white sundress) for him to wear home, we all walked over to the sleepwear section and Ryan's grandmother picked out a pink nightgown and a pair of Disney princess girls pajamas for him to wear at night.

"That's right, Ryan" she said, as she picked those out. "THIS is what you'll be wearing over your panties at night for the next few weeks at least. What do you say, Ryan?"

Ryan actually did start to cry at that point, as he came to realize how much he was going to be petticoated, but all he said was, "I understand Grammy. Thank you."

As she paid for the items, Ryan's grandmother asked me if I had many other customers like her who were buying clothes to petticoat their boys. I told her that, quite honestly, although she was far from the first, it wasn't very common. She kind of tsk tsked when I said that, and told me that she had been encouraging Ryan's mother to petticoat him for years, and that as far as she was concerned, the world would be a much better place if more boys were properly petticoated while they were growing up. Of course, as the two of them then left the store, there were other customers staring at them, but Ryan, now wearing the yellow dress, simply held his grandmother's hand and looked down. But his eyes by that time were pretty red again from crying, as were his cheeks with the redness of the shame he was feeling. But I have to say that I'm starting to think that his grandmother was right about how much better things would be if petticoat discipline were used more than it is.

Best wishes

Thank you for your letter Cheryl. We remember you and your previous letter published last month, this one is also quite special, I really appreciate you sharing these experiences with us.

Interesting instances indeed, both show the power of petticoating on young boys and go to illustrate how effective it can be. The lesbian couple working to encourage gender fluidity in their child, most positive and a wonderful example of petticoating for shaping a life of femininity for him.

The other with the grandmother, outstanding to say the least, a perfect example of petticoat discipline, using girls clothes to teach him a lesson in respect for his sister, who no doubt will be highly amused when they return from shopping. For you this must have been quite the experience, to watch, to listen and to be involved in helping her purchase the clothes.

Thank you again for considering us and for sharing these truly delightful examples of petticoating.


Return to Index
Letter 3