My 4 Year old.....baby of 5 - Bakersfield,CA

When my son was 3 and 4 (and the start of age 5 before he got teased by another boy) he loved to wear girl skirts and princess dresses. He also loved to stuff a stuffed animal down his shirt and pretend he was pregnant and going to have a baby. Perhaps your son was pretending this? My son also loved to pretend to be the girl character from cartoons and his favorite movies. He really identified with the girls - I think because they were more sweet and cute and kind. He did not hide it though - he did hit quite gleefully. He is 8 now and would be horrified if I told him he liked to do this stuff...he now is really into soccer, ski team, popular music, bmx biking, and video games. I guess keep trying to talk to him about it or see if he will let you pretend with him. Then you can gain some insight. Maybe his sister told him not to go in her room and mess with his stuff? Maybe his siblings told him that girl clothes are only for girls and teased him? Let him know you think it's just fine and ask him if he wants some of his own girl clothes to dress up in. See if he will let you play with him and maybe he will tell you what he is thinking/pretending. Don't tell him anything he is doing is wrong or make him feel bad (sounds like you already know that).

Maybe he is not sure why he wants to do it. He might feel unsure if its OK to do - someone may have told him boys dont wear girl clothes, or his sister may have said to stay out of his stuff. The other suggestions here are good. Ask him if he wants to dress up together and join him. Then you can ask more questions about what makes it fun and let him know its OK to try different things. Maybe some of big sisters clothes can get handed down to a dress up box so he feels welcome to use them.

Hi there,
My now 6 year old son did this when he around 3/4 years old too. He would go into my dresser or hamper, take clothing out, and stuff them under his clothes. It was mostly my clothing and not my husband's nor our daughter's clothing. Whenever I would catch him doing it, he would immediately yank the clothing out and seem embarrassed. I assured him that it was fine that he wanted to play with my clothes and only asked that he put it away once he was done. I recall this lasting a few months and then me moved on to some thing else. He also never really wanted to talk about what he was doing or why so I never got any reason for the behavior. It didn't last unreasonably long and while I found it peculiar, I didn't make a big deal about and actually kinda forgot about it until I read your post.

Good luck!

My 4 year old is the youngest of 2 boys. He is home and he watches some shows on the computer. I don't know how he got there, but one day I walked in and saw him looking at pictures of VERY fat girls. With captions like "watch me shrink" and an animated shrinkage to follow. Of course, he cant'read. As soon as I walked in he got very flustered and embarrassed and immediately started trying to get these images off the computer. I have NO idea where he got the idea that this would be a bad thing to look at, or that I might be upset by it... Anyway, I will be interested to see what responses you get to this. BTW, both my boys Love to dress up in my shoes and even put on makeup. I think it's just because there is no "dress-up" or makeup in a boys world.