Arwr - I tried to be a female impersonator once, but I couldn't keep my hands off myself.........
I do have experience of transvesticism though. Two former employees of mine (in fact they were two brothers) had a lovely mother, but a very stange father (I later found out). One was married, had children and had his own house, but the younger one was still living with his parents.
I had no idea that a "woman" (who was obviously not!) who came into a showroom I owned at the time was in fact the father of these two lads. I tried to be non-plussed and played along being as polite as I could, but was struggling not to laugh when two of my showroom guys were taking the piss out of me behind (his/her?) back.
A week or so later, the younger brother (who worked on site, not in the showroom) told me in passing that his dad had said I'd been very helpful and was grateful for the courtesy I'd shown him when he'd popped in.
A bit puzzled, I told him I hadn't realise I'd ever spoken to his dad and if I'd known, I'd have mentioned you to him. He told me not to worry about not recognising him because his mother's clothes were a very good fit............
This is all completely true, and I was stunned for a minute not knowing what to say until the lad burst out laughing at it himself to break the tension. Simon - if by some chance you're still out there after all these years and reading this - you made my day mate.....