Guys, did you ever wear a girl's costume or dress up like a girl for Halloween?

Question

Guys, did you ever wear a girl's costume or dress up like a girl for Halloween?

Answer 1

 I was 10 when my girl cousins, one 9 and two(twins) 13 wanted to dress me up as a girl for Halloween. I said no then they said they outvoted me three to one. I struggled and fought them the whole time but the twins overcame me. I remember they had stripped me of my shirt and pants which they gave to their little sister to wear, each one with an arm holding me between them in my tee shirt and brief, and I was still telling them they weren't going to dress me up like a girl. They just giggled and said, "Oh yes we are" and they did.

A yellow dress, white anklets, black flats, long brown wig, pink blush and lipstick later, and I was a girl. Their sister wore my pants, shirt and jacket with her hair slicked back. The twins dressed up as men in some of their dad's clothes and drawn on mustaches. They took me trick or treating and called me Missy and Little Miss all evening. I was so embarrassed.

Answer 2

 I went to a Halloween party with four girls that I worked with one time. Their condition for inviting me was that they got to pick my costume. They went as Batgirl, a flapper, a witch, and Minnie Mouse, and I went as a ballerina. They had me in pink tights and a tutu, with a curly blonde wig, silver tiara, carrying a pink glittery wand around.

Answer 3

 Yes when I was 11 I went to a Halloween carnival with my younger cousins and their babysitter at a high school a few counties from where I lived. The sitter and her friends helped me out with a last minute costume, the sitter's old girlscout uniform and a wig donated from one of the other girls. I was sure I wouldn't see anyone I knew. A girl from my home room class was there because her aunt was one of the teachers. Of course my cousins called her over and she was very surprised when it sank in who I was. 

I had fun even though I suffered a bit of embarrassment.

 

Answer 4

 In sixth grade I let the new girl, who I had a crush on, talk me into dressing up as a girl on Halloween. She dressed up as me and got her older sister to help dress me up. I wore a long brown wig with a pink ribbon in it, full make up, a pink bra with balloons filling it out, a pink blouse, black ruffled skirt, white knee socks and black maryjanes. It was pretty embarrassing. Some people thought I was a girl and some boys from school called me a sissy.