It is the first time... The first time I've written the teenage male pov. I started the chapter and then took a step back to do some more research. After finding a few good blogposts on writing from the male pov when you're not male, I dove back in. I tried really hard not to over think it and the words just flowed. There was only one point when I thought I might be untrue to the male stereo type but that's why this is a first draft. I'll come back later and figure out if those thoughts were realistic for Him and not just based on his gender.
So I finished his first chapter! Now I've got five more before it's time to wrap the book up. That will be a whole 'nother mess! Because I'm writing this from three different characters pov and haven't decided exactly how it ends. As I write this, I think I just realized I do at least know whose voice will end the book.
Fight the fight; keep on keeping on!
Ps Best piece of advice I found was in fiction, every character is made up! If you are a female writer, you aren't your female characters. So write your guys with the same dedication and made-up-it-ness you would your female characters. Make them all REAL to your reader.