See, when Devin was younger (around 3, I think) Celia (who was 8 at the time) convinced him to play dress-up. She borrowed clothes from their cousin Krystal (who is the same age as Devin) and had Devin put them on. She got Devin to play the game a few times afterward, and eventually Devin grew to like the look and feel of girls clothes. Even to the point where he started going into the girls section when clothes shopping with his parents.
He now always wears panties, though, regardless of the other clothes he's wearing. It's more of a comfort thing. He likes the fabric of the panties over that of briefs or boxers. All his panties look like the ones in this drawing (just for the sake of him always having that style panties).
As for his hair...Well, I figure Celia probably convinced him to keep it long, and she probably helps style it for him.
I don't think it's that... See, when Devin was younger (around 3, I think) Celia (who was 8 at the