Well guess who chickened out...
Seriously though, I came very close to saying it on a couple of occasions but each time something happened and it shocked me so much it put me off of saying anything. Let me explain:
Firstly we were casually talking about people from our old school, when I mentioned a girl I used to be friends with and he said to me "for some reason I always thought she looked like you in a wig"... at that point my heart literally froze and it was so unexpected I didn't know if that was a good time to say anything or not (For the record, I don't look like her - she is absolutely stunning).
The second time I was getting closer to coming out to him - I had said to him that I wished I was a bit more into men than I am now (he didn't get the hint from that unfortunately) but he mentioned his girlfriend's transgender cousin and said jokingly at one point "maybe you should do what they're doing, become a lesbian"... I just said "yeah maybe" hoping he would pick up on it but he didn't and the chance was gone. His comments just really took me by surprise and now I really wish I had said something.
But if I have gained anything from this conversation it's that I've found out he is almost definitely going to be more accepting and next time I see him I'll be able to talk about it again.
Fingers crossed for that time then!! :'D