I'm a guy, but I've always wanted to dress up in women's clothes, make-up and a long-haired wig. Should I give it a go or will I look stupid?

It means that subconsciously you want to be a lesbian or female. 

Possibly even consciously. 

Will look so stupid and gross.

So long as you keep this entirely to yourself, you need not feel silly.  Once you introduce it to anyone else, you run a great risk.  Unless you are actively encouraged by your spouse to do so, it could end your relationship.

In your own house, behind locked doors.

You would probably need to work at it.  The trouble is we don't know much about your body type.

If you just do it once (on Halloween), it's OK.

But any more than that and you will destroy your life.

Best wishes.  

I've been doing it all my life. I didn't ask anyone, I just did it. And I looked and felt as if I'd found myself. If you have to ask you clearly aren't needy. If you only want  to do it to see what it's like then you may as well go outside and kick a ball.

If it's only behind closed doors, to whom are you afraid of looking stupid?? Who's going to see you? So you're asking if YOUR FAMILY is going to think you look stupid if you do this?? How the flying hell would we know what YOUR family is going to think, dumbass? I swear this site is getting more moronic by the freaking hour.

thats up to you

Do whatever makes you comfortable, feel free to give it a go! If you decide that it’s not for you, that’s okay! If you decide that you enjoy doing it, that’s wonderful too!