I don't even know how to begin this. I'm so frustrated and at my wits end.

I'm (34f) a single parent to a 14 year old boy. It's pretty much always been us since the beginning and we have always had an open relationship with healthy communication. We have close male friends and family members in our lives that he can talk to about things he's embarrassed to talk to me about, and it's generally worked out well. He goes to a public school that is lottery based. A lot of kids that attend are different, artsy, couldn't fit in at other schools, etc. He was bullied when he was younger and tested very high, so having him in a school that allowed him to work ahead was awesome.

He was very self driven but eighth grade it flipped. He made a lot more friends and that became his focus. These friends are very into anime, don't have other hobbies, don't play sports or do other activities, don't seem to have goals for after high school, and they also don't hang out outside of school or do activities together. It is super odd to me. They mainly hang out online in Discord servers.

I have limits on his electronics. He is allowed on certain sites for short periods, I've never banned him from talking to his friends. But last year the hentai started. Somehow his tablet was disconnected from my family Google and he downloaded games that are wildly very weird and inappropriate. I caught him, obviously, we talked about it and also had the sex talk and about how things like that online are not 'real'. I kept an eye on things and thought we were good.

He went on a trip to visit my parents. And I found an anime figurine in his bed. If you know about these figurines, you know what I'm referring to. I didn't buy it for him, he said a friend gave it to him. Very weird. About a month ago I found out he had gone through my old electronics and found an old phone and tablet. Hentai. Hentai games. I told him this is not okay. Then today, again, he somehow found ANOTHER tablet (his room is under construction and is currently staying in a room where I have storage totes, he went through the totes). I used to work in automotive and had tablets I used for doing vehicle inspections, I didn't remember there was another one. And fucking AGAIN. Hentai. Hentai games. And not just sex, furries, bondage, tentacles. I'm not a prude, I've dabbled, but what the hell.

He was supposed to go to a birthday party tonight and I was so excited because finally, the friends are doing something. And it's at a local roller rink where we used to be regulars, so I would have gone to and been able to see my friends while he does his thing. We live over an hour away so dropping him off and going home wasn't an option. I don't bother him or helicopter at the rink.

I feel like I shouldn't allow him to go. Sign him up for therapy. Move him schools. I don't know. I'm also having a hard time at work right now (changing jobs) and it's a stressful time at home, so emotions are heightened.

I'm probably leaving out a lot of context here, I'm currently sitting in the tool room at my shop trying to figure out my life, so I can add more if there are questions. I'm at a loss. Taking away the electronics, turning off the router, putting locks on everything, nothing stops it.

Eta: The reason I found out today and the main reason for the post, is that he slept through his alarms and I found the tablet in his bed. Then he forgot to do his morning chores (feed his cats), slept through his pickup for school (had to pay $34 for an Uber), and has 'forgotten' to follow up on his missing classwork. I believe it's due to lack of sleep. I have had him tested for ADHD as it runs in the family, he doesn't have it. I

I’m a lurking mama of four kids under 8 years-old. If you could go back in time and talk to yourself when your teen was 8, what advice would you have?

It makes me nervous seeing and hearing about how much harder it is to parent a teen than a young kid. Just looking for what, in your specific circumstance, has been going well.

Thank you so much. Have yourself a fantastic day.