How to start sending nudes

So I really wanna send nudes to this guy I know that’s really hot and he’s asked me before to send nudes but I got nervous and didn’t. He has sent nudes with other girls before and never leaked them so I trust him plus I’ve known him for a long time and I know he’s not like that but I just don’t know how to ask him for nudes because we haven’t talked in a while. Any advice?