9 years ago(Shortly after I came out to my wife) my High School class was having their 30Th reunion. I'd recently read about another gurl who had attended hers as her femme self and in a moment of bravery decided to do the same. I discussed it with my wife and she told me to go for it but that she wouldn't be going-not because I'd be dressed but because she always got bored to tears at my reunions!!.
I made arrangements with my best friend from HS to be my escort for the night and then started to put my outfit together.
The day of the reunion, I went all out and had a full makeover(Something I've never done since because I ended up hating how it turned out), and got dressed . I had on a dark blue velvet mini dress with black 5 inch heels and long silver earrings. I'd bought a new wig and took my time getting it styled just right. I just finishing up when my friend called and backed out because he was sick(Yeah, right!).
So, undaunted I drove myself to the hotel where the event was being held , parked and made it as far as the front entrance before I started to loose my nerve. Now you have to understand that my class was huge-350 plus- and prior to this I'd never been out as Cynthia in front of more than about a dozen people. I started to pace back and forth in front of the hotel chain smoking as I tried to work up the nerve to go inside. I must have looked fairly suspicious because about 10 min later a police cruiser pulled up and asked to see my ID. Apparently someone had pegged me for a "Working Girl" something the cop and I both had a good laugh about. After he wished me a good night and told me to have fun I figured it was about time I get inside.
I walked through the lobby and over to the registration desk for the reunion. It was being run by a 20 something blond girl from the company that was putting on the event. She asked my name and without thinking about trying to change my voice just blurted out my last name in my guy voice. It didn;t seem to faze her one bit and she proceeded to go right past my name card(Which had my HS yearbook photo on it) several times before I stopped her and pointed to it. She smiled, handed it to me and pointed me in the direction of the ballroom for the event.
I walked in and made a bee line for the bar and after securing 2 very stiff drinks, went back out into the lobby to build up my courage again. I was just finishing the second(The first one I pretty much just chugged-VERY lady-like-LOL) when a guy I'd been in school with from grade school all the way through HS walked over and said "Didn;t we go to school together?" I said "Yes Bill we did" at which point "Well Hi <Male Name> , how have you been??". That broke the ice and we started talking. He asked me a few very direct questions about why I was doing what I was doing, and I answered him very truthfully that this is who I am and had been for quite some time. He never got judgmental or anything, just seemed to be curious.
After a few min he asked me if I was going inside and I said yes. He offered me his arm and we walked inside together. He knew I was one dirty look away from turning tale and heading home so he stayed right with me and took me around to every single table and asked everyone if they knew who I was. Nobody knew. He did more to help build up my confidence that first 30 min then anyone else I've ever met. Eventually he let me wander off on my own and start talking to long lost friends.
Two very funny incidents came out of that night. The first had to do with the bathroom. I'd made up my mind that I wouldn;t go into the Ladies room for several reasons. 1) I figured that if anyone was going to have a problem with me it would be the women so I'd give them at least one place where they could go that they knew I wasn;t going to be and 2) I'd had crushes on a lot of the girls in my class and I seriously doubted I'd be able to do what I needed to do in the bathroom if they were in there too!!. So, the one time I needed to go, I used the men's room. When I walked in -carefully-it was empty so I went into a stall, sat down and did what I needed to, then got out of there asap. As I was walking away from the door back into the hotel another guy from my class was heading towards it. He looked at me, and then headed for the ladies room door thinking he'd been going into the wrong bathroom. I looked at him and said "No Bob, you had it right-it's the other door!" He stopped just short of walking in to the wrong bathroom and blushed as he thanked me for stopping him.
The second was towards the end of the night. I'd been on my feet most of the night either walking around or dancing and I finally sat down for a few min to talk to another old friend from my class when a female classmate walked over and asked me how tall my heels were. I said "5 inches" and she said"You've been up all night dancing on 5 inch heels?" I said yes, and she smiled and gave me the best compliment-"*****" and a long hug. That made my whole night and I went home grinning from ear to ear.