I know he’s not terribly popular these days, but Doctor Freud would disagree with you. True, childhood sexuality bears no resemblance to our own, but in terms of sensations & experiences that are intensely pleasurable, children have them, and fairly young. Even if they’re forbidden to masturbate with their hands, or haven’t discovered it, they like sliding down banisters and riding horse toys, etc. Oftentimes people (adults) describe being aware of and/or preoccupied with some precursor of their paraphilia before they even have a sense of sexual orientation (which often manifests QUITE young). So someone who eventually likes B& D might be preoccupied with the kidnapping and tying up parts of kid stories, and “opposite sex” clothing (or, alternately, just the fabrics) can be part of that.
I’m more of a babysitter than parent, but I agree with this.
The issue isn’t wearing women’s clothes or anything sexual, it’s wearing your clothes, without permission. Underwear is worse than putting on someone else’s shirt, because most people don’t like to share underwear, even if they don’t mind sharing outer clothes (that’s how I’d put it to him). Again, it’s not that underwear is sexual, it’s just that it’s something people don’t like to share, so he shouldn’t wear someone else’s without permission. If he wants to try on some of Mommy or Daddy’s clothes, he should ask (and I don’t know why you’d say no, but he should ask, right?).
But I really don’t think you should encourage him to sneak into your drawer. I don’t know your son at all, so don’t know when it’s appropriate for him, but at some stage he’s got to get that ‘I can’t help myself’ isn’t a good excuse for taking other people’s stuff.
I’d be concerned about being placed on some sort of watch list.
Thanks for the advice and guidance – I knew Dopers would have a lot of helpful stuff to say.
Thanks especially for helping divide the issue into his not respecting the rules about leaving my things alone as separate from what he’s doing with the stuff. We will work on the boundary issue.
I absolutely get that trying on women’s clothing - dressing up of any kind - is normal at this age. Both kids have full access to a dress up box with lots of choices, and can wear anything they want. Heck my daughter’s best friend Jason had his designated princess dress that he wore every time he came over the year they were 5.
Masturbation is fine, it just needs to happen alone in a bedroom or bathroom. That also is age appropriate for a kid his age, and wouldn’t give me a moment’s pause.
Here is the thing though. When we find him with my underclothing he is aroused. Over and over he’s hiding, wearing my stolen underpants, with a little 5-year-old erection. And it isn’t tapering off like ususal kid stages; it is happening more. That is why I’m worried isn’t just a regular kid thing but something more. How long do we really tell ourselves it is just a stage and normal and he’ll move on - or not - and to not worry about it. I just don’t feel able to shrug and say yeah, all kids do that.
Excellent point and I’ve put it in his room.
Not to put creepy thoughts of your offspring jerking off into your head, but speaking as a former little girl who was a precocious masturbator, I’m 99% sure it didn’t stop but rather just went underground. 
This is the salient point.
We were told by everyone, doctor included, not to make a fuss of our daughter’s picky eating. “She’ll grow out of it!” I wish I hadn’t taken that advice.
Agreed that they would be too big, but mom can surely make a slight adjustment so that they stay on. Hell, I can barely sew a button on, and I could make something work, it doesn’t have to look perfect. I figured kid sized silk boxers would be an impossible find.
If the problem is that he is wearing YOUR underwear, why not let him have some old pants and a bra to use in his own room?
Then it will either not be forbidden and therefore exciting and will pass or he will go on wearing it in private but then your clean underwear will at least be safe.
I would have to be more graphic than I’m comfortable being on this subject to tell you how we know, but we do know for certain that she stopped. We didn’t have a problem with the fact that she was doing it, so it would be fine if she had simply learned to keep it private, but she really did stop. In fact, she learned to keep it private and then stopped a few months later.
Okay, now I’m really curious. How can you tell if someone’s masturbating without actually seeing it? Female gooiness?
I have the same feeling. Nobody has any business in my underwear unless I say so. Boundaries.
I think you need to come to terms with the fact he MAY have “imprinted” on this already. There’s no way to know at this point.
It’s interesting to me that you would seem to be very accepting and even somewhat comfortable with the notion of him being homosexual, but so uncomfortable at the thought of him being a cross-dresser.
Most cross dressers are heterosexual - they aren’t gay, they aren’t transsexuals, they’re heterosexuals who find dressing in women’s clothing erotic. It’s unusual, but not some unheard of thing. Seems to me it’s a lot like being left handed - it’s different, occasionally awkward, but ultimately just a normal human variation.
If he has an erection when you find him with your underthings I’d say it really is sexual. He may not be able to articulate that at this point, but it’s a strong indication if you ask me. Young children are not asexual beings even if they don’t have adult sexuality. As noted, kids masturbate. Perhaps you should make clear to him that this is like masturbation, a private thing, and one is not to “borrow” someone else’s possessions to perform the act.
Is he going to “grow out” of it? I have no idea.
If he really is a budding transvestite no, you can’t “turn him away” from this. You might get him to repress it until he’s out of the house, but it won’t go away just like that.
That’s like the best course if you ask me - let him express himself this way (in a safe and appropriate manner), insist he respect other peoples’ property, and either it will wear off or it won’t.
But I am neither am expert nor a parent myself.
I think you need to figure out why you’re so uncomfortable at the notion your little boy likes to dress up in your underwear. Aside from the hygiene issues, of course, but I don’t think that is why you are worried.
Are you concerned that he may be bullied by other kids if this is discovered? Are you concerned he may be rejected by potential mates in the future? Are you worried he’ll turn into a drag queen or professional female impersonator? You say you’re not worried about him being gay and I’ll take your word on that, but are you worried about him being a flaming queen? Are you worried someone in larger society will hurt him if they find out he likes to dress in women’s underthings?
If this persists then you’ll need to make sure that he is aware that not everyone is accepting. He’ll likely figure that out himself anyhow, if he hasn’t already (after all, he IS trying to hide this somewhat, he may have already picked up that this is somehow shameful).
It’s not “nothing” - transvestites are not always well accepted and it can be dangerous to be one in certain circumstances. However, it’s not the end of the world, either. A lot of people don’t care one way or the other. Is it that you don’t know any transvestites, so they seem to be an unknown quantity? (Actually, you probably DO know a transvestite or two, you just don’t know they are transvestites).
And, of course, you’re a parent - you worry about your kid. You want him to be normal. You’ll still love him even if he’s not, but you would like him to be normal and smart and strong and healthy and successful and most of all normal - 'cause, let’s face it, life is hard enough without being perceived as weird or, worse yet, perverted. He’s not perverted, of course, he’s little boy who likes to dress up. That shouldn’t be a crime, really, when you get down to it, the activity itself is pretty harmless compared to a lot of other things.
I am the mother of a five year old boy, and I really don’t see anything to get worried about.
First, the secretive behavior is normal, if you have enforced rules before about not touching other people’s things. He knows he isn’t supposed to touch your stuff, so when he does, he hides. Just like he would if he filched a lollypop when he wasn’t supposed to.
I completely disagree that the fact that he has a boner means it something “sexual”. Five year olds have no concept of “sexual” in the way adults use it. In adult context, “sexual” is used to refer to the complicated thoughts and feelings that occur with sexual behavior, many of which are imprinted by other people. For your boy, I’m betting that he gets a boner because soft silk feels good next to the penis. The penis has a zillion nerve endings, and most people like the feel of silk next to their skin. You may think it’s sexual because he has a boner, but for him, it’s just a natural body response to soft touching.
I fear that you guys, with all good intentions, have now made the “silky underwear=sexual” connection for him, with the close questioning about naked girls and such. He told you why he does it - it feels good on his skin, just like Dad’s bike shorts, and just like 99% of the population. Because he has not had the socialization, he doesn’t realize that girl stuff is, generally, for girls, and boys stuff is for boys.
The bra stuff seems to be just regular dress up, and not much of a concern as well.
I know how hard it is to want your kids to be normal, and to be overly-concerned about weird behavior. But had this been my kid, I would have just said “Hey, that’s my stuff. What are you doing?”…“Okay, well, that’s girl’s underwear, so next time we’re out, we’ll get you a pair of silk boxers. And you need to remember to stay out of my things.”
That’s it. I would certainly discuss it with my husband, and be aware of any future stuff, but that’s all. Punishment would only come if he continued to go through my stuff. If he started wearing his silk boxers and walking around with a boner, I’d just deal with it. I’ve known grown men who have gotten awkward boners, and mentioning it, talking about it, and worrying about it just seems to be to be a good way to start some “sexual” hang-ups, no matter what he becomes as a adult.
ETA: What do you mean by “sex positive”? I assume this means that any kind of sex thing in people is okay with you, but I’m not sure if that attitude is really necessary when dealing with a five year old who hasn’t been sexualized in any way. It’s just a non-issue, IMO
My son used to love playing dress up with my stuff. It was never a big deal. He’s the youngest of three and the only boy. His sisters used to do his nails and make-up for dress-up time just like they did their own.
He’s 15 now and outgrown it. I wouldn’t worry too much. And like you said in the OP, even if he doesn’t outgrow it… where’s the harm?
I like this idea, too. I do think you should make sure he gets that your things are yours and if you ask him not to touch them, then he should respect that. But I really don’t think now is the time to start worrying about his sexuality. I don’t think kids this age realize that undergarments can be sexual - I’m guessing that, to them, undies are just like other clothing. As far as he can tell, he’s just playing dress up.
My son is four and a half and still wears my high heels sometimes. He also tries to breastfeed the cat (luckily the cat’s too fast, so my son breastfeeds his stuffed cat instead).
I couldn’t agree more. You shouldn’t ASK a child if he can stay away from your things. You’re the adult, you don’t let a five year old run your life instead of you running his.
As a gay male, I can tell you, there’s nothing to worry about because it’s been decided already. If he is gay, he’s gay and whether he wears women’s clothes or not, he’s still gonna be gay. If he is gonna be a cross dresser, that is decided too. Of course more cross dressers are straight.
I recall as kids NO ONE was allowed in my parents room without specifically asking permission first. As Lynn said “Set boundaries and make him respect them.”
Kids go through a lot of phases and you don’t want to upset him. But explain if he wants to dress up, he’ll have to do it in his room, with the clothes you buy him only. It’s like anything, if he went to church he’d dress up nice. Some clothes are only appropriate at certain times.
As I said, don’t worry 'cause gay/straight or cross dresser or not, it’s pretty much been decided already.
From Roseanne:
Jackie is telling Roseanne how nice it is to be single and not have to deal with her husband Fred
I’m a 35-y.o. hetero male, and utterly healthy and “normal”, sexually. I’m very comfortable in my own skin, and have no hang-ups, at all.
But when I was growing up, I was pretty kinky. The OP’s son’s behavior sounds a lot like me, at that age (and even older). This sort of behavior for me started out VERY young, as just being very physically sensual, I guess–for example I somehow claimed some family member’s long silk underwear and used that as my “lovey” for years and years as a small child.
I experimented with a lot of sensuous behaviors as a child, some sexual, some not. Including a brief dalliance in puerile cross-dressing.
That’s all the detail I’m willing to share, except to say, sexual or not, it’s NOTHING to worry about it. As others have pointed out, the boundary/obedience issue is MUCH more pressing than the sexual identity/“kink” possibility.
Set and maintain boundaries on your personal property, but don’t spend another minute worrying about this particular behavior, even if it’s sexual. Most likely, it will pass. And if it doesn’t, who cares?
I agree that she should be in charge of him, and that property and boundaries are the important issues here, but I also don’t think it’s unreasonable to ask if he thinks he is capable of obeying. The question boils down to, “Should I treat you like a big kid, or a little kid?” Little children are locked out of things you don’t want them getting into, big children are learning self-control. Five is pretty much on the cusp where it could go either way, and encouraging self-awareness is definitely a good thing. It’s not like anyone involved thought that if he couldn’t stay out of the underwear drawer, the solution would be to just let him do it. That’s why he told her she should lock up her underwear - he doesn’t feel ready to live with temptation and not do it, at least in this area.
Hedda, I think you’re doing really well with this overall. Good luck!
I don’t think it’s weird or anything to shame him about or make him stop doing- the crossdressing- you should definitely stop him from getting into your things- but I’m going to have to disagree with anyone who says this is common behavior for this age. I have two brothers and 3 boys of my own, and a lot of my friends have multiple boys, and I’d say this is not that common. Doesn’t mean it’s bad, but I don’t think almost every boy does it. Not that it’s anything to worry about.