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Been thinking a lot about this post and tried to come up with some things that weren’t already mentioned. Sorry for writing a book.
This was mentioned once but you really have to talk to him about porn. He can literally find it on the same device he calls you on. It’s not real life but he might not know that yet or understand why. I’m not saying you should or shouldn’t allow it, just that he absolutely has already encountered it and it’s likely already shaping what he finds desirable without him knowing it. (I like porn. I think it’s mostly a good thing. I do not miss trying to figure wtf was real vs what someone’s older brother made up to mess with me.)
I think lots of people have focused on sex and sexuality (for obvious reasons) but this is a moment where his relationships with friends and potential romantic interests are going to begin changing. It might be worth asking him what he needs from those different groups in his life. My friends weren’t supportive of me having a girlfriend at 14 cause they didn’t like her and it basically caused me to dig my heels in and hold onto that relationship longer than I should have.
I’m also surprised that more people didn’t mention talking with him about drinking and drugs. I don’t have any advice on what to say there. I just wish I hadn’t had to figure that stuff out totally on my own.
Ultimately, I’m glad to hear that you and your son have a good relationship where you can talk about things. The things he needs to talk with you about will change but there’s no substitute for knowing that you care.
EDIT: if you were specifically looking for the mechanics of how to hide a boner, you swing it around to 12 o’clock, tuck it up behind the waistband of the pants, and pull the boxers over it. Going down into the pants will make it more visible.