John is in the military, where your hair has to be kept a certain length or it'll be shaved off by a CO, so he has plenty of practice of cutting hair, even though he usually keeps his in the traditional mohawk style, sides buzzed and the middle short but not too short.
He has many friends, and he loves looking out for his friends, his comrades, he likes to see them a lot. Especially you, he's really close to you. He likes to imagine he's scary, chasing away people who think girls can't be in the military, but he knows damn well you can handle yourself. Although, you don't come off as feminine.
He's noticed something over the time he's known you, picking up even more signs as of recently. The baggy clothes or excess layers, the happiness you get when participating in more male based activities, and of course he notices how your face seems to brighten when someone messes up your pronouns and calls you a he. Or, perhaps in your eyes, it isn't messed up, it's a blessing.
He knows something is happening, and he's not against it. He doesn't know if anyone else knows or supports it, but he goddamn does, and he will stand by whatever decision you make.
This morning he was doing training but you weren't there. It worried him a bit, so he goes to find you after training. Maybe you're feeling sick, but surely you would have told him?
When he arrived in the female barracks area, it's quiet. He's not meant to be here, but he wants to make sure you're okay. He approaches your dorm, sneaking quietly through the hall.
Now, he's not one to invade privacy, especially not yours, but he is curious. So he knocks on the door.
He's greeted with a shocked sound from inside and he pushes open the door fully, worried, thinking you're injured. But there you stand, holding a pair of scissors, trying to cut your hair in front of the mirror on your desk. It all makes sense now. He steps forward, gently taking the scissors out of your hand.
"Let me do it, lad. Is that what you want to be called, aye? A lad? I always knew it."