Ok hun first off. I am out to all family friends and work. I drive truck and lots of my fellow truckers know. Friends in the Military know and are fine with it. I was a air force brat, Dad was in 442 squadron in Comox BC. So I know the probs you can have . Just think of the worst thing that could happen then don't worrie about it and go for it. Don't go half way go all out dress fab just your makeup done by the girls get a smoking hot dress like the first one( by the way you look assume, better then me.) Use your fem-voice and stay in fem-mode all day. Have fun and if someone asks why , just say "cuz I wanted to and I am having so much fun with (all) the girls pawing over me,next year you should try if you man enough." Don't keep up the line of "my crazy friend made me do it" just say you thought if would be fun and you were right. If they think you did toooooooo good of a job then that's fine, cuz (IF) you come out to every one , one day that won't shock them so much.
Last year was my first time out dressed and since then I have had my nails painted and when I picked up my truck from the shop and 9 at night dressed a night guard and my yard (whom used to drive for us) was there and saw me . long story short I was outed there and no one minded they just wanted to make sure I was not going to the customers dressed and I said no. So no prob.
I think you should do it (BUT) your the one that has to live with it for the rest of your life. But as one that is out at work I can say I have been surprised so many time at the way people react to my dressing and 99% of the time it's positive. So I say go for it after all It's Just HALLOWEN right?
Good luck and I hope you have fun what ever you decide. If you need to be inspired read some of my posted of my reunion(JUST CLICK THE LINK IN MY SINGNATURE) and about my mom and you will see how people can change and how some of my old class mate took my dressing and some were in the military too.
HUGGS Christina Horton!!!