Cross dressing is a harmless fetish, which for a younger child might not even be a fetish, but only a game. In any event, it is OK, although doubtlessly there are some people who would take offense.
yes
It is OK to wear pantyhose during sex, it is down to the preference of those involved.
MEN LOOKS VERY GOOD IN PANTYHOSE AND SHORTS
If you emo.
There are different kinds.
If you are girl YES if a boy and you are straight NO.
If you are male, you shouldn’t be wearing pantyhose. Pantyhose are a female garment to be worn with skirts or dresses. The current social preference is women wear tights in society. Men should stick to pants or shorts.
It means he should wear a condom!
Be careful about this. I think it is okay. I don't wear them myself. But a lot of people will have negative reactions if they find out. Just use common sense when you want to wear them. The safest place would be your own house or apartment to do this. I wear pantyhose all the time for a few years now. I shave my legs and I wear shorts with it in summer time. Do I get looks from others? Yes from time to time. Do I care? Yes I did for a while but I do not anymore. I feel like just hearing dog barking when I walk down the street. I wear it for comfort and fashion reasons, not fetish, and I feel totally good about it.
As often as he wants to and can get away with it. You can't wear it out.
pretend you are taken by another boy but make sure you know this kid and he is ok with what you are doing.
Please don't wear panties to school. Pantyhose/Tights were made to be worn with or without panties (optional). That's why they replaced stockings (which only go up to the thigh, at most). Most tights have a cotton crotch which replaces the need to wear underwear with tights ;-)