Will I be able to transfer my gta 5 dlc?

I am preordering the gta 5 collectors edition which comes with a lot of dlc. I wanted to share this dlc with my friend. Will I be able to transfer that way its on my PS3 and his PS3? I have transfered dlc before by downloading on my PS3 and then going onto his, logging into my account and redownloading it. Will I be able to do this again?