from Cheryl

Dear Helga,

I'm not sure if you remember, but I had written to you several times earlier describing my experiences with petticoating, involving, first, my job in a department store, and then helping a friend care for her children. Now that life is back to something close to normal after the pandemic, I have been meaning to write to you again.

I had mentioned the last time I wrote to you how surprising it was to me that I had been directly involved in petticoating and really feminizing two previously-very-disobedient boys. Well, since then I had the experience of doubling that number! About six months ago, quite out of the blue, I was contacted by two women who asked if I would supervise their children's remote online schooling. I declined, telling them that I was not a teacher so I wasn't sure I could do a good job. However, they said that they had heard from my friend Cat how pleased she was with my work with her children and how confident they were that I would be able to do equally well with theirs, especially with their sons. They then made me a very generous offer, so generous that I couldn't refuse it.

That's how I ended up watching over a pod of six children five days per week as the children worked on their online schooling activities at my home. The two mothers, it turned out, are sisters. One is a single mother. The other is married to a professor, and they each have three children, and in each case they have two girls and a boy. Because of the moms' descriptions of the difficulties they were having getting their sons to do the school work, which was probably the main reason they were seeking my help, I spoke with the moms about discipline options, and they each said they were fine with pretty much anything I might want to use if it would be effective in getting their boys to be better behaved and to work harder and be more attentive during their online classes. Just to be sure we were all on the same page, I asked specifically about both the use of spanking and about petticoat discipline. Both moms said that either or both of those would be fine, and that, in fact, if their sons ended up much more girlish, then that would actually be great with them if it meant that their boys were more obedient and considerate.

To make a long story sort of short, both boys (who are ages 8 and 9) proved themselves to be quite unpleasant and ill mannered and disobedient from the very first day of my supervision, and as a result they learned quickly how unpleasant it was to receive a pants-down spanking from me in front of their siblings and cousins. The girls, not surprisingly, really enjoyed seeing the boys being punished. That was the first week. During the second week, I warned the boys that I would add pantying to their punishments if they continued to cause problems. They didn't seem to believe that I would put them in panties, and one told me to my face that his mom would not let me do that to him. He was wrong. Very wrong. By the end of that week both boys were in panties, and their moms were helpful and supportive, while the girls seemed to never tire of teasing the boys about being pantied. But there was more.

Boys that age seem to have a lot of difficulty being perfectly obedient, and sure enough, each boy disobeyed enough even after being pantied that I upped the degree of their petticoating to the point that by the end of the third week, both boys were spending their school days dressed completely as girls, including panties, knee socks, mary jane shoes, pleated skirts, and frilly blouses, and with ribbons in their hair, all of which amused their sisters no end and quite pleased their mothers. After that, I settled on a "school uniform" for the boys consisting of a green-tartan skirt and white blouse, with green knee socks and a green ribbon in their hair, and that what they had to wear every day except Fridays. Fridays, their moms were free to put them in anything the moms wanted, as long as it was a complete outfit of girls clothes. Usually that meant dresses, although on one particularly hot Friday, one of them showed up in pink short shorts and a pink hello kitty t-shirt. And to help reinforce the effects of the boys being petticoated during the school day, both moms started also petticoating the boys at home, including making them sleep in panties and nighties.

What surprised even me a bit was how little the boys complained about being petticoated. My guess is that was partly a result of having spent so much of the past year at home without being permitted to spend any time with other boys. They definitely did complain the first couple of days, but after that they really didn't at all, except when they asked why it was that they had to always wear a skirt and blouse while the girls got to wear whatever they wanted, and that usually meant that the girls were in jeans while their brothers wore the more girlish clothes. I simply told them that their sisters got to wear whatever they wanted just because they really were girls, while they had to wear skirts because that's what sissy boys had to wear. And that was that.

After about two months of the boys being petticoated every day, it became clear that they had not only become accustomed to dressing as girls, but had come to like looking pretty and girlish and had become quite girlish in how they behaved. For instance, when they walked and sat, they moved like girls, smoothing their skirts as they sat and being careful when they knelt down so as not to flash their panties too much. They also started to hold their hands in a girlish way and moved their hands as they talked in a very feminine manner. For me, I think that kind of change is really what it's all about.

Some people might wonder about the long term use of petticoating, because once a boy becomes used to it, and comes to not only accept it but to enjoy it, then being petticoated is no longer really a punishment. That's true, but that is also what I've found to be so gratifying about long term petticoating, that is, the experience of watching a boy change to the point that his sense of boyish masculinity has been fully extinguished while his feminine girlish feelings and patterns of behavior have taken over pretty much completely. So, for instance, in my experience, when I've petticoated boys and then commented on how pretty and girlish they look, the boys at first respond to the compliment with obvious feelings of shame and humiliation, and frequently will protest that they're boys and that they aren't pretty and girlish. But eventually, that kind of response gives way to a boy feeling very pleased at the compliment, and that's when I know the petticoating has done what I love to see it doing, which is to make a boy really feel like and want to be a girl.

By the end of the semester, it was certainly the case that all of my, and their moms', goals had been achieved. All the children did well in school that semester, which represented a huge improvement on the part of the boys. Also, by the end of the semester there was no question that the boys each felt very girlish and both moms commented to me about how pleased they were with how everything had worked out, and they even gave me a really big bonus! I have to say that the boys certainly looked quite adorable in their matching school uniforms. One of the sweetest moments for me was right at the end of the semester, on the final day of online school, when the children were being picked up from my house by their moms, and I could see that both boys were feeling quite sad and were on the verge of tears. When their moms asked them why, both boys said that they were sad to be leaving me and sad that they wouldn't be able to wear their school uniforms again. At that moment the moms looked at each other and laughed a bit, and then told their boys that they had every intention of continuing their petticoating, and that as far as they were concerned the days of their boys wearing anything other than panties, skirt, and blouses, and other girls clothes, were over. A few months earlier, a statement like that would have shocked and angered the boys, but on that day, all it did was to put a smile on their faces as they hugged their moms in gratitude.

Oh dear. This letter has gotten much longer than I had anticipated. I actually was prompted to write to you primarily to tell you about some of my more recent petticoated-boys experiences now that I'm back working at the department store. But maybe it would be best to save that for another letter. All I'll say for now is that it sure seems, based on my experiences at the store, that life during the pandemic brought out the sissy side in a lot of boys and the desire to sissify their sons in a lot of mothers. Whereas before the pandemic it was quite unusual for a woman to bring her son into the girl's department to buy clothes for him, during the two months since I started working in the department store again, that has become a much more common experience. I can tell you about some of those experiences when I write again.

For now,

Hope all is well.


How wonderful to hear from you again, Of course I remember you as will my readers. Your stories of petticoating deserving young boys are legendary and some of my top downloads. Obviously the skill you possess in the practice of petticoat discipline is becoming well known around town; for the mothers, a godsend and for those lucky boys, taught to become proper girls by a gifted and experienced teacher.

I really can't thank you enough for continuing to share your adventures with me, real petticoating as we've discussed has been rather rare, but now with this lockdown and mothers having the inclination to tame their rowdy sons, I hope we see more of it and as you noted, more have been coming into the store. I look forward to hear about those experiences as well.


Return to Index
Letter 5