Too good at it

[Stephanie47]

Many years ago I was in a local variety store on Halloween. One of the young male employees walked through the store to show off his 'costume.' He was young. He was cute. He was 100% passable, and, if he did not announce himself none of his co workers would have known it was him and not a young woman. I was near two female employees who expressed their opinion he HAD to be a cross dresser. If I had the opportunity to go out on Halloween, I would probably just stroll through the residential streets. But, alas, I will just dispense sugary treats.

[Jennifer in CO]

I only remember doing Halloween once dressed. I was 12 or 13 (honestly don't remember right now) and had bugged my Mom to let me ToT as a girl and she relented. Underneath I wore a lightly padded bra that had been my Sister's, Sis' maroon velvet micro mini dress (with matching pantie cover - this was around 1970), a pair of pantie hose, Sis' black Go-Go boots, and Mom's butt-length (on me) wig (which happened to be the same hair color as my own). Mom then did my makeup (quite well) and sent me out. Everyone knew I was a boy dressed as a girl because a girl just doesn't go out ToT looking like a normal version of herself...it was fun. The problem came when I got back home about an hour later. I was to go to a friends house in our old neighborhood (we had moved about 6 months earlier) for a party and wanted to change into "normal" clothes. Well, Mom said she didn't have any makeup remover and I'd look really silly dressed like a boy and wearing makeup so she all but insisted that if I was going to the party I go as I was. I really think she was trying to embarrass me so dressed but it didn't work. I went to the party and those that knew me thought I had a cool costume. Those that didn't know me (including a lot of parents) just thought I was a girl as there were several girls there not in costume. I was treated like a totally normal person (a girl) all evening long. The girls that were there treated me like another girl and the boys did too (even the ones that knew I wasn't a girl). Course, I did my best to act like one as well. For a young, budding transgender, it was wonderful.

Oh...and when I got home?...Mom "just happened" to find her makeup remover while I was gone.

Jenn

[erika_kerrie]

Kinda happened to me. Years ago some friends and I all decided to go as the spice girls, I went along with the idea I was ginger spice. Anyways my friends girlfriend helped us all with our makeup and our dressing, I could have looked a bit more convincing but I went along with it. I was the smallest of my buddies and I did look like a girl the most, but no one made any comments to me, at least not too my face. My friends girlfriend who helped us out joked that she and I should go clubbing afterwards

[outhiking]

I guess I was/am more afraid that they would see that I enjoy it too much.

[ArleneRaquel]

I always dress female on Halloween, at least since 2004.

[AllisontheGoddess]

Sometimes, but sometimes it's difficult because people give me compliments and want to take to me---but then I have to ruin their expectations with my "man" voice. =/ (gets a little awkward sometimes)

[LunaDarling]

im going out as a woman for Halloween tomorrow. ive been a caricature of a woman before for halloween and felt perfectly comfortable, probably because i knew that everyone knew it was just a costume. im going to a house party with a lot of my friends and it could turn out pretty big and im TERRIFIED and super excited about the idea of everyone seeing me. it will be the first time being out when im trying to look my best. i fear the fact people will know that my outfit is not an accident and that ive clearly been playing with makeup for a while now.... im tired of hiding it though, damn it. this is happening!

[Sarah Doepner]

I've dressed two different ways to present as female for Halloween. One is as Nurse Ratchet from "One Flew Over the Cuckoo's Nest" and the other was just as a woman wearing a nice Halloween Blouse and slacks. When I wore the 'normal' outfit my wife and I went shopping and dropped in at my daughters apartment for something. She asked too many questions and I haven't done that again. In the Nurse outfit I did a family party and some trick or treating with the grandkids, no real problems but I've been asked to do it again some day. I also went shopping in that outfit and at the checkout stand the clerk complimented me on my look and went on to explain that her manager also came dressed as a woman, but he was "way too good at it" and she had her suspicions. I guess I wasn't "way too good" because she had no doubt in her mind that I was an amature.

[Jenniferathome]

I've written this several times, but dressing as a woman is NOT a costume. It makes no sense. It has no irony and subtle meaning. Absolutely everyone will wonder why you are dressing as a woman. By the way, a "sexy witch" is the WORST costume according to my wife. It's a dead giveaway that you are a crossdresser. Halloweener beware!

[AmyGaleRT]

Our office Halloween party was today, complete with a costume contest. I considered attending as Amy, but in the end, decided not to. Part of me regrets that decision.

I probably would have been pegged as "too good," which would have had my coworkers asking questions I didn't really want to answer right now...but I think it would have felt good.

Ah well, there's always next year...after I've gotten a bit more practice...

- Amy