If a girl asks a boy to wear a pink dress for her, should the boy do that or not? Reason?

What kind of girl would even ASK a guy to do that? Trust me, if a girl asked you to do that for her, she just wants to ridiculize you and make a big joke out of you. Don't fall for it.

What context? If she's just seeing if you'll jump through her hoops like a nice little puppy, then no. But if there's a good reason for it, maybe so. It just depends on why she's asking.

Ummmmmmmmmmmmmm NO! What the heck man are you serious? If you put on a pink dress for a girl just because she asks you too, and its not like a prank or halloween joke or anything, oh man why would you do that? If some girl asked me to put on a pink dress for her I would say nope why don't you put on the dress for me, since you are the girl, girls wear dresses guys don't. Man if you wear that pink dress you might as well hand in your man card now.

What do you get out of it?

If she wants to play dress up and have sex, maybe. If she just wants you to do it to see if you will, probably not. People who want you to "prove" your love are a waste of time. This includes the people who intentionally withhold sex to see how long you will stay without it. We hang with people because we like them, not because they endure some sort of humiliating test. People who want to make you jump through hoops don't like you enough to keep you when you get done. In fact, they often lose respect for you if you do.

I did have a few women in my life who enjoyed putting makeup on me (it was the 80s and Twisted Sister was all the rage). It was fun for them and it didn't become public information so I didn't mind.

This is an out to lunch request and sounds like controlling behavior. Next she'll have you barking like a dog.

Watch out when the camera comes out and she wants to take a picture because you're so cute.

you could do it to prove your love for her sure! but personally, I wouldn't do it! it is a little far fetched to say the least!