from Cheryl

Dear Helga,

I've worked as a saleswoman in women's retail every since I graduated from high school about 20 years ago, and a lot of that time I've specialized in lingerie, and oh, the stories I could tell. One of the open secrets in the business is how much women's lingerie is purchased by men for themselves! A day doesn't go by that I don't see a man pursuing the panties or slips or bras or stockings etc., with that look in his eyes that tells me that, no matter what he says, he's not shopping for a wife or girlfriend, but for himself. I learned early on how to tease these men into spending hundreds. Occasionally, we get wives with their husbands shopping for lingerie for the men, but that isn't very common, and a very small number of times I've dealt with women who are in the store with a boyfriend and their husband, buying panties for the hubby. Wow.

But those are tales for another time. You see, I also sometimes work in the girls clothes section, and I wanted to write about something that has just started happening in the past couple of years, and it seemed what I had to say might be of interest to you and maybe your readers. What I'm talking about now are women who are with a son and are shopping for panties and other girls clothes for their boy.

I can't remember that ever happening until a few years ago, and even now it doesn't happen a lot, but maybe just once a week or so that I've become aware of. It's amazing how much I learn about them when I serve them, because usually they are quite comfortable telling about what's going on. Usually, but certainly not always, they are single moms, and the boys are almost always in the 7-10 years old range, but a few women with teenage boys have shown up too. I'll describe a few of these customers.

The ones I like to serve the most involve women with sons who simply want to be girls. Just last week, for example, I saw a woman shopping while holding the hand of a boy who looked to be about 8. She was looking at blouses and holding them up to the boy to check the fit. When I went over to ask them if they needed any help, she smiled, said yes, and then told her son to tell "the nice saleslady' why they were there. I could see that the boy was quite shy, and was clinging to his mother more like a preschooler than a boy his age, and I could also see that he was effeminate for a boy his age and with his long hair and soft rather pretty features I was already thinking that he probably was sometimes mistaken for a girl. It took some urging on her part, but finally the boy whispered, then with more urging said a little more clearly, that the reason they were there was because he didn't want to be a boy anymore, he wanted to be a girl. His mother then told me that it seemed he had always felt that way, but that it had taken her until very recently to really accept the truth of the situation. So now, they were shopping for the first time for girls clothes for him.

I led them to some changing rooms, and over the next hour or so brought them piles of panties and skirts and blouses and dresses for him to try on. What was so sweet about it was seeing him look at himself in the mirror each time he tried on something new. It was clear that he really loved seeing how he looked in just about everything. He'd look at himself, and smile, and twirl while looking, and pull up his skirts or dresses to look again at the panties he tried on. His mother could sense how thrilled he was, and she was just beaming as well. I think they ended up buying about a dozen pairs of panties, maybe five skirts, a dozen blouses, and four or five dresses, and when we were done, they just left his boys clothes for me to throw away and he left the store wearing one of his new outfits, and I doubt that anyone seeing him realized that the pretty girl they were seeing was really a boy. I was left feeling wonderful myself, about helping a boy look so pretty and feel so happy.

Since you focus more on petticoat discipline, which is a term I had never heard of until a couple of years ago, I guess I should also describe one of the times I've helped women who have brought their sons into the store to be punished by being put into girls clothes. I can't say that this has happened very much, but when it does it's pretty memorable. The first time, it was a woman whose son was thirteen. Now that is really unusual, to see a woman shopping with a boy that age. Especially because the boy held his mother's hand and they were in the teen girls section looking at bras. When I approached them, I could see that his eyes looked like he had been crying. I hung back for a few minutes and overheard him quietly but almost constantly begging his mother not to make him wear a bra and promising over and over that he'd be good and that she didn't need to do that to him.

Needless to say, I could barely believe what I was hearing. I guess I should explain that he was dressed in a light jacket and pants and a shirt, except that when I finally went up to them to offer to help, I could see that the shirt was really a blouse and the navy blue pants zipped up the side and had no pockets. When I went up to them I could see actual traces of tears on his cheeks, and his mother very directly and matter of fact told me that he had been disobedient at home and had been doing poorly in school to and so she was petticoat punishing him (yes, she used that term). When I got out my tape measure and suggested we go to a changing room, she said it was OK to measure him right there and made him take off his jacket. As I put the tape around his chest I noticed a couple of girls nearby who were staring and giggling at what they were seeing, but then, after I picked out a couple of padded training bras in his size, we did go to a changing room for him to try them on. When we got into the changing room he again started to plead with his mother again, but now he was saying he'd be good about wearing a bra at home if only she wouldn't make him wear one when they left the store. In fact, he never really stopped begging even while trying on the bras, and when he did that I was also able to see that he was wearing panties underneath his girls pants. I'm sure it won't surprise you to know that when they finished, having purchased three padded bras for him to wear, she did make him wear one out of the store underneath his blouse and she wouldn't let him put his jacket on over it.

As I said, I have a lot more stories I can tell that are like these and about some of the men I've sold lingerie to, but these should give a sense of some of the more interesting customers I've had recently, and I hope you find them interesting, even if you're not as surprised as I've been about them.


Thank you for your letter Cheryl. What a delightful letter and such fascinating experiences you've had in this field. I would love to hear more, whatever you wish to share, if you can find the time. I know how much my visitors enjoy reading about those mothers that felt petticoating was right for their sons, that must have given you a special feeling to witness and assist.


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