Hi Nat,
For me I like both sides of me. Dressing and makeup with breast forms then work gear, heavy machinery and chainsaws. There are so many paths and as long as you all stay supportive they will be easier to follow.
The struggle to understand is real, communication and support both family and professional is key to finding the right path.
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He has a love of gaming, sports and his bike, things you would consider typical really, growing up it has always been a bit of a mixture up until now. He loved dolls and princess dresses as well as his collection of cars etc.
Nat, I don't have a clue about your son's situation. This is why I suggested you ask him. As I wrote, transitioning is "long, difficult, expensive, painful, and problematic," but it is made more successful by youth. I hope he simply likes to cross dress. That's an easier path.
Does he resonate as female in any other ways? For example, as a kid, I collected doilies and rhinestones and did crafts. I played with girls and was the block's babysitter. As an adult, I continued in childcare as an elementary school teacher.
He has always loved all things that you would associate as female, he often chose Disney themed bedding for instance, used to love making jewellery from beads and painting his nails.
But up until now it was always a mixture of these two sides of his personality, there have been periods when he completely dropped the girly things but from a little research I don't think that is unusual ?
We had a really good chat today, it was really sunny so we sat in the garden and talked for ages.
I asked him all the difficult questions, why he was spending so much time in his girls clothes, was he happy being a boy, did he have any thoughts about the future etc.
So he says he is happy being a boy but just wishes he could be himself all the time, he said he gets jealous of girls because they can wear whatever they like, sometimes he feels sad because he has to wear ugly clothes.
He cant explain why he likes girls clothes other than they feel nice, look nice and he likes the way they make him feel.
He said that he wished he could go out dressed but he didn't think I would let him so had never asked (thats a teen asking

)
He actually admitted that he thinks it will be hard to go back to normal after lock down but he knows he has no choice so will just have to do it. He kept asking for re assurance that I didn't mind, I guess because I was probing he was worried.
We got talking about his birthday and as it was just the three of us this year i suggested we could have a proper girls only day, that bought a smile to his face so his head is full of plans for that right now.
I know he has been looking at summer dresses with his sister so I think I am going to ask her to pick one that I can wrap up as a gift.
A couple of hours later I had a text from him saying that he hadn't had any new underwear for ages and was there any chance I could order him some online if he gave me his savings. Of course I am not going to make him pay but told him to let me know what he wanted. He sent links for a selection of knickers no problem there I have bought him some in the past but also three bras two with heavy padding and one t shirt bra so thats a development !
They are now saying on the news that we are probably looking at another three weeks of lock down, do I let this continue and just hope it all works out when normality returns I worry I am risking damaging him what ever I do arrghhhhh its so complicated