A month or so back I had a dilemma about whether to tell girl I'd met about me, in the end I thought it was best to bring everything out in the open with her. This was a good idea and we've become good friends but for various reasons (not solely due to me being TG) that's where we'll remain, she's been really supportive and has provided some great words of advice. I'm sure some may be disappointed but don't be as I've gained a lovely understanding friend.
On another tack now, I recently went to see a very good friend of mine who has been so since my first week at university. I went with it in the back of my mind that I would like to tell him about Gender Dysphoria and me, I had no idea when would be the best time to broach the subject or how. He's a little bit of a Monty Python fan and I was semi-tempted to come out with "I want to be a woman Stan!" but I wasn't sure how I would follow it, luckily the day before he and his wife had been joking that I looked like a Lady (cue Little Briton voices) because I was spinning a parasol belonging to their daughter. I said "Remember you said I was a Lady yesterday, well it's not too far from the truth - I've something called gender dysphoria which is when someone isn't happy with the gender they are." and after a brief pause he said "Really? Are you joking" (or something along those lines) so I went on to explain that it wasn't something I'd just decided but something that had been with me for many years. He was absolutely lovely about it all, gave me a hug (awww) and said that I'm still the same person inside with the same interests etc. We had a good conversation about it and I explained that the term Transgender is an umbrella term that covers a wide spectrum and that sexuality and gender are two separate things. He's been really supportive since telling him and asked for any web resources that might help his understanding on the subject, I passed the links I went to see my GP with plus a couple of videos I've linked to previously in my posts.
I felt like I could trust this person with this and hoped they would be understanding although I had to prepare myself for loosing a friend as you've got to do with anyone you tell, even family. I tried to tell my parents recently and couldn't bring myself to broach the subject with them, I'm obviously not ready for that one just yet. I'm so glad that I didn't loose a friend, I'm sure everyone won't be as understanding or supportive... those that matter don't care and those that care don't matter.