Everytime Halloween comes around, I have to laugh. In Sept '12 my then GF/now mentor Vikki & I were watching a TV show where the women were in early 60s fashion. (not sure if it was Pan-Am, Madmen, or the movie Boeing Boeing) I commented how sexy I thought early 60s women's fashions were. Vikki shoots back "Do you know how uncomfortable those girdles & bras must have been!!!!' I wanted to tell her yes but I hadn't let her know I CD, so I backed down. About a month later she tells me that we have been invited to a costume party & she tells me that she found me an early 60s bra/girdle & a pseudo flight attendant uniform. I wanted to kiss her but I told her "Not only no, but hell no!!"
A day before the party she told me to Nair shower. I played dumb & asked her "What do you drink this?" She said "Don't you dare! You pour this on the area you want hair to go away. Well, I went into the shower. I took longer than I should have so she wouldn't know that I knew what I was doing. I came out of the shower & saw a 'granny panty" I yelled "I am not wearing this!" I came out, wearing the 'granny panty' into where Vikki had set up her makeup. She hands me the bra/girdle which I struggle? to put on. After she stuffs socks in the bra cups, she has me sit at the table & she applies the makeup. As I am sitting there, I laugh inside thinking "Vikki, you might think this is a punishment but I could just burst to tell you I CD!!!!' After she was done, she had me put on the white blouse, dark blue skirt & matching blazer. She pins on a kiddie airline pin. She then gets out a black wig, pins it to my combed hair & tops it off w/ a Jackie Kennedy style pillbox hat. As I stood there looking at myself in the mirror, I was aching to tell her. I wasn't sure how she would take it that I CD. I pretended to struggle as we walked down the sidewalk to her SUV. We got to the party & everyone had a good time. There were a few guys in drag but it was obvious that they were in it for laughs. I wanted so bad to tell Vikki & the world that I was comfortable in these clothes but chickened out. Wondering if any others had the same experience?