I was going to post about my first time truly out in another thread. As I started writing I decided to tell the whole story about what was really my first date. I don't want to take over the other thread so here goes.
Back in 1961 I wasn't sure what I was or who I should be. I realized I was straight and not interested in guys, but did like appearing as a girl and enjoyed playing the role in a non sexual way. Over the years I morphed to liking the clothes more than appearing as a woman.
It started as a joke and liberated me in that I could truly pass and live as a young woman. A friend challenged me to go as his date to a drive in movie. At the time I didn't think he had any idea I was a cd. He didn't, but was interested in me. It was a sock-hop night for couples at a drive in movie. Entry was free for contest couples and prizes for the best couple and car. Over the 3 weeks of getting ready for the event everything took on a bigger picture. Originally we were going as cartoon characters. My landlady knew of my CDing and suggested she would help me. She had a beauty shop. As my friend and I started talking more about it we moved toward pulling it off as a serious entry in the best couple/car contest.
I decided I would go as Sandra Dee. I had a nice blond wig. Bought a skirt similar to one she wore in a movie. I had petticoats that my sisters had given me. My features were very fine with light blond hair. That afternoon my landlady transformed me in to a teen girl. She told me to shave and put on my panties, bra, slips. She did my hair and makeup. It was exciting setting there in my lingerie getting ready for a date. We talked about my enjoyment of dressing and her wishing she could have had a daughter. Then I put on my white blouse which let my white bra be easily seen. I put the skirt on over my head with her help so as not to mess up my wig. She was surprised that I knew to pull my skirt up and adjust my blouse. On went my bobby socks and shoes. I WAS READY AND NERVOUS!
As a joke my friend had to come in and meet my "parents" which was my landlady and her live in boyfriend. He came in and was dumbfounded. I did not look like his buddy who cruised the hangouts on weekends. We took pictures of us like we were going to a prom or event. Mother, Father, Daughter then the couple. It was fun and I bonded with my landlady and her boyfriend as their new "daughter".
My friend had a 57 Chevy convertible. The top was down, so on good advice from my landlady, I made him put it up so my hair wouldn't get blown around. We went to the drive-in event and put the top down before we drove in. I had a pretty headscarf to cover my hair. The car, him, and my outfit drew instant attention. While we waited for everything to start several of the entries were up dancing. As I have explained before my sisters had taught me to dance as a girl, and I was more comfortable dancing as such. We had a ball dancing with the other couples. The first movie started and we went back to the car. I sat in the center of the seat so we looked like a couple. During intermission between the movies all the entries had to drive through the rows waving and getting honks for judging. The second movie the judges wondered around and we knew we were in contention. Since all the judges were guys, I made sure my skirt, was pulled up to show plenty of petticoats, but not too much. I also curled up my feet on the seat as I leaned on my "boyfriend".
At the end of the second movie they announced 3 cars were winners. One was ours. The moment of truth and could we pull it off? We walked up to the snack shack holding hands like the other couples. We lined up and they called third place which we weren't. The guy gave his girl a kiss. Then we heard we won. An unexpected kiss. The prize was several car passes and money for the snack bar.
We went back several times that summer playing our roles and cruised the drive in restaurants as a couple. We were good friends as I was too feminine for him and I was not into guys.
