Online Pornography & Chinuch Part I

So we are heading into the "I'm totally inexperienced" portion of parenting again.  Since my oldest is in her twenties, it's been a while since I've felt myself in this position, even though every child is different and there are always new challenges.

I have three younger brothers, so I have always had a sense of little boys and what they are like.  However, I got married young and did not live with them when they were teens.  I was already dating my husband at the oldest of my brother's bar mitzva.

So just as I never had a boy's education regarding mishna and gemara (though I did learn mishna in elementary school and some gemara post-high school), I really am not sure what I'm doing in terms of male puberty, male teenager-ness, all sorts of things.  Ari does have some strong ideas (one of the more salient that no 7th grade son of his shall ever be bored out of his mind in gemara) but day-to-day, I'm in the trenches with them.  And I'm kind of feeling my way.

It's been my experience that when I learn on the job, the oldest one suffers.  I can't get experience until I get experience, and that perforce means mistakes.

With that intro, I recently began the murky world of navigating online pornography.

We allow unlimited multimedia in our home.  (Here are our basic internet safety guidelines.) We do not have filters on our devices.  (I actually recently checked, and all of the computers default on the google browser to "safe browsing," and I changed 11yo's tablet to safe browsing, too.)  When they were young, we had only desktops and no tablets allowed in bedrooms.  But when teenagers start cocooning, they need privacy, they like to be on screens, and easily get around restrictions.

How to achieve self regulation?  How to achieve thoughtfulness?  How to avoid "going down the rabbit hole" of pornography?  Is that something a parent can influence?

As my sons get older, I've been wondering how to talk to them about it, what approach to take.  I have begun asking around and gathering information.

The first thing I did was ask a family with 3 boys, ages 17-21.  I got some very good advice:

• They don't want to navigate it alone; they want parental guidance [both secular and halachically]
• They want to be left alone to figure things out themselves without their parents angsting about what they're doing
  (I realize there is some contradiction.  I asked more than one person and it's important to remember that even in the same family, different kids have different needs)
• They do not want to feel like their parents are upset or horrified 
• It's really important to feel comfortable, like you can bring up questions to your parents and have a conversation about it, and they won't freak out.  And that the parents will give them information.  And that the parents won't be worrying about everything.
  
  Armed with that information, I asked some seasoned unschoolers what their approach is.  That will be Part 2.