I finally came out to my best "bud" from HS the other day. He emailed my old email address and I saw it completely by chance. He is 2600 miles away and had no idea about my transition. It went very well, we ended up talking for 90mins. He asked me all the usual questions and told me about his newborn daughter. I have been off of the radar to my HS friends for about a year and a half (when I deleted my old Facebook account). Nobody has seen me for 2 years.
Anyway something happened that left me extremely excited (besides the fact that he supports me!)... We are going to get all of our other friends together and not tell them at all who I am. My best friend even mentioned wanting to videotape their reactions and I promised not to stop him

None of my HS friends are violent or lgbtq-phobic type though so I'm not worried about upsetting anyone. My hope is to try to pass as long as possible and then start making subtle hints until they get it, if I don't burst out into laughter first.
Has anyone else done anything similar? Or what were your experiences coming out to old friends in a surprising way during or post-transition? What were their reactions? I'm sure there are some great ones