Ok, so I confided in my friend that I had a strong feminine side but I didn't go into detail about being transgender or the crossdressing. I didn't want to risk her freaking out. I am trying to get up the courage to tell her more but was wondering if you guys could help me iterate it. I have a slight stutter, especially when I am excited/nervous and don't want to Bobby Bouche' this.

So, any tips or advice to make this easier?

I'm prone to stammering a little when under that sort of stress too - I'd defy anybody to keep a straight and level voice in this situation. I recommend you start by knowing and accepting this - that what you're about to do is not easy.

There's a line they often say in films and TV when spilling feelings of love and anger, somewhere along the lines of "please don't stop me or I'll never get through this". I tried to keep this in mind by impressing upon my parents (who were the hardest) that what I had to say was important. That way, if you'd like to, you can form it all into a letter and simply read the letter aloud. The letter might be in your head or you could read off a sheet of paper, but either way you can get out all you feel you need to say.

Apart from that, I found I had to really tweak what I was saying for each individual person. Talking to my Mum was a far cry from writing to my former housemate, or asking a friend of 11 years for help. I tried to keep things personal, though - it's easier if people see the you rather than 'the disembodied transsexuality' of it all.

Good luck, of course!

Breathe. Do some research. Having notecards might even help a little. Be open to any questions they have and don't be offended if they freak out. And dont be freaked out if they figured that you were.

Been getting some stuff together to have incase I freeze. I'll let you all know how it goes.

QuoteStay gold.

I love that book! The Outsiders is awesome! Set right by where I live too. Unless you mean the Robert Frost poem...it's good too.

Have you considered writing a carefully worded letter instead of having a conversation?

Have you gotten a diagnosis yet? If so, I would explain to her that I have been diagnosed with Gender Identity Disorder. It means that you feel uncomfortable day to day as a male, and that there is nothing any doctor or psychiatrist can do to make you happy other than to change your body to match what your mind feels more comfortable with. If she thinks you're full of it, tell her to look it up, it is a real disorder and nothing that has been tried has made anybody feel more comfortable living as the gender they're born as.

If no diagnosis has been made, idk if I'd tell anybody yet. If you're dying to tell her, maybe tell her you believe yourself to be gender dysphoric and that you are looking for help to try to correct this. This will probably start a conversation that will end up revealing most of everything about it.

Be open but try to be as honest and as technical as possible. People seem to be more understanding if they believe such things are actual medical / mental problems. Afterall, it is more likely someone will be accepting to somebody "with a condition" (Gender Identity Disorder) than it is to accept "a choice" (trans-anything / crossdressing *sounds* like a choice to those that don't know any better, and has many negative social stigmas attached to it, unfortunately).

Good luck and I hope no matter what you tell her, she will be supportive

Rest assured that when you say it, only telling the entire thing is enough, and to most people, that's too much.  Condition or choice, depends on who the people are, most of the people I know would rather believe that you are choosing to follow your bliss and leave it at that.  Only by telling the whole thing can you really tell the true thing.  And, once you do that - well, out is out, you never get to put it back in.