Domain transfer question

I’m wanting to transfer two of my domain names, both of which I registered through Dreamhost. I’m wanting to transfer them to, so I can give control of them to my Brother, as I have too many domain names, and can’t keep up with them all. How do I do that?

Also, one of the domain names that I want to trasfer was the free domain that I received when I signed up with Dreamhost. I’ve heard there is a charge to transfer that domain. Is there any truth to that?