I'm going to tell my trans male friend to shut up about his dick. I just don't want to hear it anymore.
Why are you telling your friend to shut up?
I was really tired of it and I think he's too proud about himself.
It's understandable that you are uncomfortable with your friend discussing his privates. It's okay for you to let him know that it is not a topic that you want to continue talking about. Letting him know how you feel will help him understand your boundaries.
I got nothing to lose, he's just going to wait till I'm asleep and cry infront of my bed.
You don't need to let it get to you that badly. You should however make sure you let him know what you would like kept secret and what he should talk about when it comes to him being trans.