I shared a flat with a guy who was a cross-dresser. I'd known about it since I walked in on him when we were both in the same college. We were good buddies, nothing more. He also was not in the slightest way homosexual. Very red-blooded male, very much into red-blooded male stuff, a ladies man who had a string of girlfriends. I had started going out with husband at the time. It was while sharing a flat with this bloke, that I learned to sleep with earplugs because his nocturnal antics with girlfriends in the next room would keep me awake.
But one night a week, he would get dressed up in women's clothing and ask me to help him with his make-up. His personality seemed to change on those nights, he became more passive, quieter and almost introverted (compared to his usual loud self).
Some time after this, he became seriously involved with just one girl. She was not the most understanding - when she found out (because he finally told her) she immediately blamed me as being the bad influence on him, accused me of twisting his mind and then began to blame me for absolutely everything wrong in the place, including the bathroom mould! Whenever they had a fight she would use the approach of "Choose - it's X or me." X meaning whatever activity he was involved in that she didn't like. I was still young and naive, but I knew better than to ever give a guy an ultimatum over something so very important to his nature.
With my friend - I believe he used to cross-dress as a way to give himself a stress break. Being male was something he threw himself into so thoroughly, that having a night off a week was a safety valve for him.
The last I saw of this guy was some years later. We happened to have become involved in the same direct marketing scheme. He had married his girlfriend, meanwhile husband & I had married. Initially we had each been invited to the others' wedding, but his girlfriend was becoming so unpleasant, I had to cut off all contact. Looking back - she was jealous of our friendship and felt threatened by it, simply because I had known him longer. She also was judging me by her standards - in other words, she didn't trust me to not make a pass at him, because she DID make a pass at husband, big time (who is bulletproof, but she didn't know that at the time).
So we bumped into one another again, as two couples. They had a child by then, we still hadn't started our family. And friend seemed trapped. No way was that going to last... but not because of the cross-dressing.
I remember talking to my friend about when it started for him - he said he thought it began in his early teens, possibly sooner. He had a very normal upbringing, his parents were lovely people (we spent some time with them, visited them often). He had other ways to get his 'fix' of cross-dressing without suspicion - he joined a Scottish dance group for a while so he could wear a kilt without anyone suspecting he had an ulterior motive. And at that time, kaftans were 'in'. I remember he threw a pyjama party once and wore a long nightshirt all evening.
My friend found ways to get his fix of cross-dressing in socially acceptable ways, as far as possible. But it wasn't enough for him, he needed more. Back in those days, going outside the home in women's clothing was NOT safe if you were a bloke. It was illegal for us then. So he never left the house. Besides, there was only so much I could do with the make-up - this guy had a five o'clock shadow half an hour after shaving! Must have been that overdose of testosterone I suspect he was blessed with.
It really was weird living with him - it was a combination of James Bond and GI Joe six days out of seven, then it was Danny La Rue...
Marg