Did it all start at Halloween for anyone?

[Karren H]

Not for me. I started at the age of 7. And never really associated crossdressing with Halloween until coming here.

[Monique65]

Reading this thread brought back fond memories of my first and only time out in public dressed en femme. I was in my mid teens and told my mother that I wanted to attend a Halloween activity in another town dressed as a girl. She gave me a skirt and blouse and tied a pretty scarf around my head. I wore my sister’s Bobby socks and tennis shoes. What she didn’t know was I had borrowed a pair of my sister’s panties and a bra in order to feel complete.

She dropped me off at the event, and I spent several glorious hours roaming around feeling very feminine. I wasn’t worried about seeing anyone I knew, just enjoying the chance to explore my surroundings. At the end of the evening, she picked me up and I had to relinquish my attire, but the feeling remained. Unfortunately I never had the opportunity to repeat it, and it has become one of my treasured memories.