Dear Auntie Helga,
I can't believe I'm writing to you, but I'm worried about a situation involving my son and it's the kind of situation it seems you might know a lot about, so i hope you don't mind my writing.
My wife and I have two children, a 10-year-old daughter Jenny and an 8-year-old son Jaime. As I'm writing this, Jenny and Jaime are in Jenny's bedroom playing together. Jaime is wearing panties, a skirt, and a blouse, and his long hair is in braids tied at the ends with two pink ribbons. If you saw them, it would never occur to you that Jaime wasn't a girl, which is the problem I'm writing about. I guess this situation is partly my fault, but it's been one of those cases where things happened very gradually and I just never knew when or how to stop it. This is how it's happened.
When the pandemic quarantine started where we live, Jaime already had longish hair for a boy and was due for a haircut. But any chance of going to a barber changed when we quarantined, and even four months later we didn't want to take a chance of catching the virus, so even though by then his hair had really gotten quite girlishly long we didn't have it cut. One evening his hair was getting in his eyes so Valerie, my wife, decided to put some bobby pins in it. Jaime whined that boys don't have bobby pins in their hair, but Val paid little attention to his complaint and put them in, telling him that he needed something to hold his hair back from his face, and she also made the obvious point that no one would see him except us so it was no big deal. I should probably also explain that in our family Val pretty much makes all the decisions about the kids, and she does not appreciate it if one of the kids disagrees with one of her decisions, and that goes doubly for how she reacts if I disagree with her, so I almost never even question anything she decides.
So that's how it all started. After that, for a few days, Val put bobbie pins in Jaime's hair and he stopped complaining about it. Then, about a week later, along with a couple of bobbie pins, Val used a couple of Jenny's red barrette's to help hold his hair back. Again, Jaime complained that boys don't wear barrettes in their hair, and even I asked Val if that was really necessary, but she just somewhat angrily said that barrettes worked better than just bobbie pins and that Jaime and I needed to be quiet about it, and she also said that we were just being silly because it wasn't as if wearing barrettes would actually make Jaime a girl.
For a couple of weeks, that's how things were, with Val putting barrettes in Jaime's hair every day, or sometimes telling me to do it. In looking back, I realize that's when I probably should have been more forceful in stopping things, but I didn't, and I think that the fact that I was now sometimes the one who was making him look more girlish made Jaime pretty much give up on trying to resist what was being done to him.
Nothing really changed for another few weeks, and then one morning, Val decided that Jaime's hair had gotten so long that she needed to do something more, so she brushed it into two pigtail braids, each one tied at the end with a small pink ribbon. Jaime didn't dare complain to his mother, but he did come crying to me, asking me to ask Val not to make him wear his hair that way. I nervously suggested to Val that maybe this was too much, but she angrily told me she didn't want to discuss it. I realized my best approach was to help Jaime accept things, so I pointed out to him that Native American braves often wore their hair in braids, so it was OK for a boy to wear them. And just like with the barrettes, it wasn't long before Val had appointed me to be the one who brushed Jaime's hair and put it into braids or pigtails or a pony tail each morning, and I always had to make sure I used pretty ribbons to finish (the couple of times when I used plain elastics, Val made clear she wasn't pleased). Sometimes I also used one of Jenny's hair bands too to help hold Jaime's hair in place in front.
As the weeks passed, Jaime's hair continued to get longer of course, until he was begging us to cut it for him because it was getting in his eyes in front. I was relieved when Val agreed to do it, but then, what she did was to cut the hair in front into very girlish bangs. Again, I probably should have put my foot down then, because Jaime was pretty upset with how he looked with bangs and with his hair in braids or a pony tail tied with ribbons, but we all thought the pandemic would end soon, so I told Jaime to try to not let it bother him for the time being.
As you know, though, the pandemic dragged on and on, so when summer ended, instead of the kids going to school they had to do school remotely from home. And we were fearful of taking the kids to a barber or hair dresser, so Jaime continued to grow his hair and to have to wear it in a girlish style. But that was nothing really compared to what came next. Soon after the end of summer, Jaime came to me in tears and told me that his mom had decided he had to start wearing his sister's hand-me-dowm panties! Well I decided that was too much, so I confronted Val about it, but that conversation didn't go the way I thought it would. Val rather sternly reminded me that we were not in good financial shape and had to save money wherever we could, and that one obvious way to do that was to put off buying Jaime any new clothes, and instead have him start to wear his sister's old clothes. I asked her if that meant that she was going to make Jaime wear some of Jenny's other clothes that she had outgrown, meaning blouses and skirts and so on, and Val said yes, that was what she had decided. I knew that trying to demand that she change her mind would not work at all, but I did beg her not to do that to Jaime, that maybe it would be OK if he wore panties but I pleaded with her not to put him in other girls clothes. To my surprise and relief, Val relented, at least a bit, and we agreed that Jaime would wear panties all the tme and would sleep in some of Jenny's old pajamas and nightgowns, but he wouldn't have to wear blouses or skirts or dresses, at least for the time being. I thanked Val for being so understanding and went off to tell Jaime what had been decided. He was still pretty upset about it all, but I pointed out to him that he wasn't spending any time with any of his friends, so it really wouldn't matter what he wore.
Well, that was about three months ago now, and as you can probably guess, during that time Val decided that Jaime would wear hand-me-downs from his sister all the time, meaning he has had to dress as a girl all day and night every day. When his mom put him into skirts and dresses I had a talk with him, and reminded him that wearing girls clothes didn't make him a girl, so he should try to just make the best of it and not let it bother him. He tearfully agreed to try. And he has tried, and seems to have succeeded.
Which brings me to what is concerning me now. What seems to have happened is that he's been becoming really girlish as he's spent week after week dressed as a girl, almost as if the clothes really are turning him into a girl. It isn't just that he's stopped complaining about having to wear panties and skirts and blouses, what has become obvious is that he quite likes wearing pretty clothes and he likes having long girlish hair. Jenny has even started referring to Jaime has her little sister. I'm worried now that when the time does come for the kids to start going to school in person again, that Jaime will have become so deeply immersed to feeling and looking like a girl that it might be hard for me to then make him go back to being the boy that he used to be.
So that's my current dilemma, and there are not many people I can talk to about the problem, so I thought you might be able to offer some insights or advice.
Thanks for reading this
Thank you for your letter Tom. I can understand how you could be concerned bout your wife's feminization of your son. I appreciate the background information and if I might start by making an observation, your glorious wife seems to be in charge be it panties for your son, or other issues in the relationship while you are submissive to her, would you agree? As for him going back to school, that will be a challenging decision and one Val will likely make and you will agree to her wishes because that's who you are, that's a good thing. As for Jamie's school wear, it may be that the school is gender-fluid and he could could come as a girl. You could show him that being feminine is a good thing by joining him in panties and other pretty clothes, ask Val how she would feel about that.