A 14 year old boy will inevitably be curious about the fairer sex in her lacy undies but, despite your best efforts, a 14 year old boy will get hold of material either with or without your knowledge, if he so wishes.
"Safe and normal" would be a 14 year old boy, who has managed to get his hands on some girly mags, having been brought up to be able to separate this as fantasy and a bit of illicit fun rather than real life.
That's the bit where I think parents come in and guide. Deny all knowledge that it exists and where do you think they will get their guidance from..?
When I was a teenager I could sense that my parents were terrified my sister and I were going to go out and get pregnant, smoke, drink, whatever but they didn't trust their own instincts. They had brought me up to know that these things existed and hadn't sealed me off from it but they had done the job of making me understand they were wrong.
Rather boringly I completed a decent education, got good jobs, had nice boyfriends, got married, agonised over the best time to have a baby and generally planned my life.
I knew pron existed, giggled and sniggered over pictures of willies and boobies with chums but that's as far as it went.
If I had a 14 year old who wanted a Playboy mag, I would give him a copy of that book to read. Boys need to learn that pornography is neither real sex nor real sexuality. Any 14 y.o who is beginning to develop his/her sexuality will of course sneak a few glimpses here and there.. but I don't like the idea of an adult giving him a copy.. developing relationships should be encouraged, not pornography.
Just my 2 cents..
Reason and moderation? I do not think 14 y.o. boys have the emotional maturity to consider moderation. And if you are going to give them a copy of Playboy, why stop there? Where is the line?
To the OP: After reading your further comments it just looks like the kid is testing the limits with you. If the boy is being raised in a healthy lifestyle more power to you and his mother. If you're looking for advice, I've given you my 2 bits worth but I'm certainly not going to cross the line of assasinating your character over a couple of nudie pics. Good luck
But yes, you're right I am 30 now, and I got here without being 14. I totally don't remember what it was like. I totally don't remember the things I did that I wasn't supposed to.
All teenagers are going to be exposed to things that their parents would rather they not be. Such is life. The only thing that parents can do is to try and equip their children with the tools and knowledge to know how to handle the situations that they encounter, because they're not going to be able to be there all the time.
The fact that this kid has an adult that he trusts, that is not his parent, that he can talk to about these types of things is wonderful.
A famous Swiss man thought when he was 16, that to become a real man, he would have to get caught and stuck in prison, swear,rot,fart,drink and be very much interested in girls. So he took off and did just that. At the end he found it was much tougher then he thought to become a man and maybe that advice of his own father needed some revising ...
Be his friend, say no, get it yourself.