Heyy...
Okay if this guy you like asks you to send him a naked picture but than says I'm just messing but wants you to send him a pic... Should you tell him to stop asking you?

I would just dump him as a boyfriend and find one that respects me more. I remember some cases of suicide this last couple of years where one person sen naked photos but latter the person sent to them everyone in school. Another where it was sent out by mistake.

If you want him to see you naked, do it in person with no cameras.

If he makes you feel uncomfortable or teases you like that then you should either confront him or stop talking to him. Things like these can be stressful and we may end up making choices that we later regret. So do yourself a favour and never send anybody a naked photo.

From your profile:

About mame_chula123
Experience
I am 14 years old...

The language I would use to describe a male who wants a 14 year old female to send him a naked picture would get me in trouble. I don't believe the 'just joking/kidding around' backtracking.

This is someone you need to talk to your parents/guardians about and they need to contact the police. This person is asking for what is called 'child pornography'. Yes, you could be in trouble if you sent him a naked picture of yourself.

Don't send anything to this person or have any contact with him. Please, use common sense and don't allow someone to flatter, guilt, etc. you into doing what he wants. You used it in coming here. Use it to continue making good choices.