Maya, what kind of binder is he using? Because if it's not working, he should probably at least look into other kinds (or the sizing could be off).
Okay, my two cents. First picture definitely looks female. The second picture, could've gone either way for me. Honestly, in that second picture he looks a lot like a kid I went to school with. Soft features on both of them, but still a male looking face.
The rings and jewelery? That's a whole different story. If that's what makes him confident, what makes him feel secure? Keep it. Or at least try it. I tried stripping all my "me"ness down, wearing just huge hoodies and baggy jeans, tucking all my hair up under a hat and even with all that, I got "miss" occasionally. Granted, they looked vaguely disgusted, but still. But since I went back to wearing my copious amounts of bling and whatnot, I haven't gotten anything beyond dude, sir, or guy. Granted, I'm exceptionally lucky with my voice, but still. I've got a huge chest, and I'm kind of...lumpy.
The confidence thing, seriously. I had no idea how true it was until I saw that in action.
If he's into that metal look, and if he's wearing tons of silver/pewter skulls and bones and badassery, people will probably think he's some highschool metalhead goth kid. Agreeing with everyone else on the hair, maybe try some hats? I know that wearing a beanie has always made me look a lot more masculine.