I have crossdressed since I was about 7 or 8. I started with my mothers stockings and panties, wearing them in bed and having some very erotic dreams.
Later moved to buying my own clothes, sometimes from Charity shops, other times from Marks and Spencers. Eventually got brave enough to buy from specialised shops in London's Soho, where I could admit they were for me.
After being able to drive I went to nearby towns, partly dressed, and put makeup and shoes on in the car, parked in a multi storey car park. Would then walk around going into various shops and also a ladies toilet.
Also would do the same but to a woodland area where I could walk around.
Now I am married and cannot freely dress, as my SO does not know. I have a couple of ladies who let me dress when I go to see them, and will escort me to various towns for shopping expeditions.