There is only the one, and he's 13. Lovely boy. We hope he stays that way....
He would certainly know about the 'heels' and Mrs Freddy. There was a time when her family and friends expected her to appear in very high heels every time they met her. (I may have had some influence there...) Been a little while since that was the case, but her shoe collection is still 'Legend'. While my heels are not left out for him (or anyone else) to stumble over, an inquisitive person (he is) might not have found it too difficult to find the rack with my shoes and boots on. If he had suspicions, he might ask. Since he hasn't asked, I have to assume he doesn't 'know'. I'd like to tell him, but it might create some 'influence' (normalisation) and that could draw him down a route he might otherwise not take.
My concern, is this: If he knows men wear heels, he will try them on (his mothers.) If on trying them he both likes/enjoys them, that will never change. (Experience tells me.) That could in turn, lead him along the same line of 'interest' I have had for the wrong side of 50 years. I found a way to make it a pleasure for me for all that time, but it was a challenge to make it a pleasure. I was brought up in challenging times, so it wasn't something I felt was a hardship, as with everything else, you just 'got on with it'.
Our current youth don't have this sort of environment (school of hard knocks) to toughen them up to the challenges they will experience in their lives. They are (frankly) soft of mind and body compared to those of the late 50's and 60's. Back then, people were still going hungry. Still struggling to own a car. Using a phone meant walking to a street corner to use a public phone. Televisions were often rented not owned. Dirty work often killed parents prematurely.
So my concern is: My influence might lead a 'soft' (malleable) mind toward a path they ultimately struggle to cope with. If it (the mind) gets there without influence, then 'fate' (or DNA) is responsible, not me. If it (the mind) does get there, I can offer support and experience, provided either would be welcome. (As with all young people, they all know everything, so are usually unwilling to take guidance.)
Why am I so sure this situation is a prospect? He is considered to be quite a 'genteel' lad. Not interested in sport because he is tall and slight, lacking 'strength' but is a very bright lad. Has more girlfriends than 'mates', though he does have mates too. In many respects, he has quite a worldly head on his shoulders. He has the intellect to cope with unusual situations, but I don't know he (yet) has (or will ever have) the strength of character to walk away from temptation ~ even when knowing there could be a precipice somewhere along the route. Coming full circle, my own experience suggests that's a challenge my family are not well equipped to deal with. I might have been in my mid-thirties before I realised I could be my own person. That's too late for some.