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Happy Crossdresser Day....so many times I've wanted to say that today instead of Happy Halloween.
For many of us CDs, today has such a special meaning, it's a day we've used as an excuse to try to test the social waters around us to feel the temperature of acceptance, or it's a day we've tried going out dressed up and hid among the other costumes, or it's the day we dream of being ourselves, or it's the day we find wigs, fake nails, cheap makeup, size 10-13 heels, fishnet stockings, kinky outfits appear in stores everywhere. There are the discounts too the day after.
For me, Halloween has so many CD memories. Years ago, a few weeks before the day, I bought a pair of heels, borrowed (without asking) an old dress of my wife's, borrowed her tights, put everything on and showed her my "going as a girl" outfit. It almost sounded plausible except for my wife suspicious wondering why I didn't want to go dressed to work like that for Halloween, or why exactly had I bought a pair of women's shoes and when was I going to return them to the store. Then, weeks later, her wondering why I hadn't returned the heels back to the store.
A few years ago, I had the audacity to wear women's clothes out, sort of blending into guys clothes, while running errands on the day. Unexpectedly, I ran into a couple of female friends and tried hard to conceal the feminine highlights on my jeans pockets. One of them seemed a bit perplexed as she gave me one of those tight, feel up my back hugs, where I'm sure she felt my padded bra push up against hers, or her hand waved over my bra strap/closure being felt through my shirt. She did smile, but has never made any mention of her suspicion.
Then, there's the yearly ritual that maybe this will be the year that I surprise coworkers and family with a realistic feminine outfit, only to shyly retreat back into the closet and just wear drab as I silently protest a holiday in which men wearing women's clothes brings many unexpected remarks, from applause for the comedy, to admiration of the fashion choices, to amazement over balancing in heels, to crude remarks from jock-type guys.
It's almost over, hope your Halloween or Crossdresser Day went as well as you expected!
The first time I ever dressed fully femme was for a Halloween party in my freshmen year in college. It was a great opportunity to wear pantyhose and show off my legs. I did that and got lots of attention and compliments. It was more fun than I could have expected. I met other dressers and they invited me to join them at their parties which they regularly held.
The girl I went with that night dressed as a guy. We won "best couple theme" and I won "sexiest costume" and "best legs". That was really surprising. And it did open up many new avenues and experiences.
My first time out in public dressed was halloween when I was 11. I still remember that night vividly, my sisters short pink dress and heels with all the goodies, bra stockings, panties and oranges for boobs. I had a great night out trick or treating with my friends and went home and pretended to fall asleep on my bed still dressed so I could stay that way all night. I'd played around in my sisters stuff before that but this was the night that Heather came to be. I will never forget that night. Heather.
My first time was also Halloween as a kid. Probably around the same age as Heather, though I don't recall for sure. I went as a girl scout. Family friends had a girl about my age, and I borrowed her uniform. My mother did my makeup. I don't remember if I had a wig or not. I just remember a lot of people being surprised I was a girl.
I don't remember coming up with the idea on my own, but I really don't know where the idea originated - if it was me, my mother, my mother's friend, or whoever. I also don't remember really being upset about the idea leading up to Hallloween, or nervous for that matter.
And it's sort of funny how I really had no obvious interest in crossdressing again until college when my girlfriend (now wife) convinced me to wear her panties for a day. And then, how it didn't come up again for another 22 or so years. No going back now, though! 🙂
2016_personal stories: Lea original post:
Happy Crossdresser Day….so many times I’ve wanted to say that today instead of Happy Halloween.
For many of us CDs, today has such a special meaning, it’s a day we’ve used as an excuse to try to test the social waters around us to feel the temperature of acceptance, or it’s a day we’ve tried going out dressed up and hid among the other costumes, or it’s the day we dream of being ourselves, or it’s the day we find wigs, fake nails, cheap makeup, size 10-13 heels, fishnet stockings, kinky outfits appear in stores everywhere. There are the discounts too the day after.
For me, Halloween has so many CD memories. Years ago, a few weeks before the day, I bought a pair of heels, borrowed (without asking) an old dress of my wife’s, borrowed her tights, put everything on and showed her my “going as a girl” outfit. It almost sounded plausible except for my wife suspicious wondering why I didn’t want to go dressed to work like that for Halloween, or why exactly had I bought a pair of women’s shoes and when was I going to return them to the store. Then, weeks later, her wondering why I hadn’t returned the heels back to the store.
A few years ago, I had the audacity to wear women’s clothes out, sort of blending into guys clothes, while running errands on the day. Unexpectedly, I ran into a couple of female friends and tried hard to conceal the feminine highlights on my jeans pockets. One of them seemed a bit perplexed as she gave me one of those tight, feel up my back hugs, where I’m sure she felt my padded bra push up against hers, or her hand waved over my bra strap/closure being felt through my shirt. She did smile, but has never made any mention of her suspicion.
Then, there’s the yearly ritual that maybe this will be the year that I surprise coworkers and family with a realistic feminine outfit, only to shyly retreat back into the closet and just wear drab as I silently protest a holiday in which men wearing women’s clothes brings many unexpected remarks, from applause for the comedy, to admiration of the fashion choices, to amazement over balancing in heels, to crude remarks from jock-type guys.
It’s almost over, hope your Halloween or Crossdresser Day went as well as you expected!
