Same way anyone crossdresses, wear clothing that is only worn by the opposite sex.
if you would let him crossdress any other day, then let him do it on halloween
depence on your mothers character, i would adivise you to talk about it with your parrents as they might help you out.
A rhinestone collar and leash should do it.
homosexual
It is difficult to determine an exact number, as individual preferences and boundaries vary greatly. However, some partners may enjoy crossdressing for events like Halloween or Comic Con as a fun and creative way to express themselves. Communication and mutual consent are key in a healthy and respectful relationship when discussing such activities.
a guy would probaly ask you to see what your looking for in a guy, in other words he probaly likes you.
Spain recognizes same sex marriage. They don't have much problem with cross dressing.
By fighting the bad guy.
I would call that my dream guy! lolz! but i would say it would be obedient.
I would say that if you date one guy, and kiss another, that would be cheating. And cheating is bad.
The hot but poor guy.
Depends on the context - "guys" is the plural of guy, so you would use it if you are talking about more than one guy. "Guy's" means you are talking about some that belongs to that guy for example "That guy's coat is really nice." OK?