In Canada it was really simple. I just sent in my therapists letter stating I should be treated like a man, filled out the application form and where it said "why are you changing your name?" I put in "Because of a gender change." I had no problems what so ever and I moved to a very male name and also changed my last name to that of my grandmothers on my fathers side while I was at it lol. Don't be worried =) It will all go ok and work out. It's a bit different in the US I hear, since you guys have to go into court whereas in Canada we just need to swear before the person taking our application that we aren't up to no good lol, but I didn't even have to do that... In any case, theres no reason for a judge to refuse you your name change unless you are a changing your name to avoid a crime you committed and I expect you aren't doing it for that reason
If it's the court you're worried about, trust me, the judge doesn't care, he sees countless people every single day of his life getting a name change, he's not going to have a vendetta against you, he's just there to do his job. You'll be in an out and happy as a peach. People change there names
all the time and some name changes are pretty hilarious (for instance the kid who changed his name to SpidermanJesusBuddah, cause why not lol).
Good luck!
Ps: lol please change your name to Philosoraptor Smith! lol just kidding, seriously don't worry about it. One court appearance of awkwardness for a lifetime of happiness is a good trade in my opinion!