So Halloween is coming up and although I'm perfectly fine being masculine and portraying that image, because of my extreme genitalia dysphoria I'm thinking of going as a girl this year. It would totally throw all of my friends and acquaintances for a loop, but I'm kind of thinking I want to see their reaction to my costume to see how I should proceed with "transitioning" if that's the correct path for me.

Do you think this is a good plan or should I just play it safe??

Yes , do it. It is Halloween, have fun with it! I am going as a woman vampire, it will be so much fun! Might even be therapeutic, who knows.

I agree, I say go for it. You can have fun and at the same time test the waters with people you are close to. Dressing in "costume" was one of the first socially therapeutic gender things I experienced. Truly one of the best feelings. It is also how I got my name

Just watch out for the rise and fall, I remember the comedown was pretty harsh when I had to go back to male mode. Yes, it's kind of like a drug to be accepted for how you see yourself- even if just partially in "costume" form.

When the night is over, just remember that you have your whole future ahead of you. Enjoy the cookies!

Firstly I would say go for it. I also agree with Jenny that once the genie is out of her bottle it is very hard to put her back in. I remember going to a fancy dress party when I was 15 or 16, the problem was I 'passed' too well - the genie never went back