First let me start by saying I am not a crossdresser I am a transgirl but you asked about Halloween so....

At 6 I said I wanted to be a princess for Halloween. My parents were reluctant but my sister said she'd help me with my hair and makeup before school that day and take me trick or treating with them in the evening. Like I said, my parents were really reluctant, my mom more so than my dad but they agreed to let me.

For the entire month of October I was thinking about how I might look and feel . When that day/night night came around it was magical (no pun intended). A few days before we got my costume, a lovely pink and white satin princess dress with a tiara. My sister bought me some matching shoes a little girl's clutch purse and clip on earrings. In another bag were some underthings. A little white nylon slip and a pack of girls panties. She asked me if I wanted to wear that stuff too and I nodded.

The clothes and outfit was so soft and so different than my boy clothes and i loved how i felt walking in it with the material caressing my legs.

I got up 2 hours early because I was so anxious that I couldn't sleep and I was told to be up an hour earlier than normal. My mom and my sister helped me get dressed then my mom went to work and my sister did my makeup and hair and showed me how to powder my face and reapply lipgloss then that stuff went into the clutch purse and she drove me to school.

A lot of kids made fun of me but not everyone, some girls thought i looked really good and didn't know who I was at first thinking i was a new girl in the school. That made me feel really good. They asked me questions about my hair and makeup and I told them my sister helped me. They asked me to sit with them at lunch (normally I sat alone). I felt accepted on some small level as another girl.

That night my family took me trick or treating and no one in the neighborhood knew who I was, they thought I might be one of my cousins.

After it trick or treating was over, my mom was like "well you had quite a day, let's get you out of that costume" and I asked if I could keep it on and she asked me why since Halloween was over and I said because I felt I was a girl inside and I liked how it felt and I wished I could wear dresses every day.

And kind of stunned she just walked out of the room, got my dad and asked me to tell him what I told her. I did and my dad kind of just nodded like he expected this and the two of them walked out of the room before coming back and saying I could keep it on until bedtime.

I began wearing those panties under my boy clothes and my parents asked if I'd like to see someone to talk about my feelings. I said yes.

The rest is history, I started seeing a child psychologist and she recommended i be allowed to play how i wanted and dress how i wanted at home after school and on weekends or vacation. A year later my room was repainted in all disney princess colors pink and lavender and i got a girl's bed and night stand set. I got clothes handed down from my sisters and some new things my mom bought towards the end of the year.

At 12 they realized it wasn't a phase and I started testosterone blockers and we got my name legally changed. I also went to school wearing a dress for the first time since that Halloween.

A year or so later I began estrogen hormones and 5 years ago I had surgery.

I'm 22 now and in college and no one knows I'm trans.

Forum

crossdressing

crossdressing