Too good at it

[audreyinalbany]

Anybody every refrain from dressing in female mode for a Halloween party because people would find you a little too convincing as a girl?

[NicoleScott]

On Halloween several years ago, our office was visited by about 5 costumed employees of a neighboring business. One was a rather petite young man dressed as a girl. Really, a knockout presentation. When the group left, the office was abuzz about him, with many commenting that it was "too good" - "he's done this before" - "this isn't a costume, it's an opportunity" - etc.

[TGMarla]

I did the Halloween thing once, many years ago. Although I didn't hear any comments from anyone about it, I think I came off as just a bit too good at it for it to be some kind of spur of the moment Halloween costume. My wife was amazed at the makeup job I'd done, too. (This was before she knew about me.) So all in all, it's not something I'd recommend unless you purposely do a bad job on yourself. I've seen other crossdressed guys on Halloween, of course, and most look like longshoremen in drag. It's obviously a costume, kinda hideous, and rather humorous. No one sees them as regular crossdressers.

[linda allen]

I would not do it with people I know because of just that - I would be "too good at it". I mean, what normal guy would have a wig, women's shoes that fit, clothes, get the makeup right, etc.

Going out on the town or to a bar with strangers would be different. Hopefully, I would just be a woman in their eyes. If there's any doubt, they would think it was a costume.

[Beverley Sims]

Because of my activities from the past people who see me dressed up for the first time are left in no doubt I dress well because I can.
They still don't know I CD though. :)

[Cheryl T]

Nope....in fact the first time I did it for Halloween (my very first time in public) I went to the extreme of doing my very best to look as feminine as possible. I didn't want to be a caricature of a woman, I wanted everyone to see me as a woman.

[Taylor186]

Being "too good at it" and being "too convincing as a girl" are two different things to me. I'm guilty of the former but never the latter.

Many years ago I went to a local party hosted by a work friend that included many work friends. I wasn't even good at it back then: a cheap wig, poor makeup, a men's turtleneck, skirt made out of old pair of jeans, three pairs of hose to cover leg hair and boots (ok, the boots with 4" heels were hot), and I was still considered "too good at it." Decided right then to not go to another work related party dressed.

I'm much, much better "at it" today, and go out every Halloween, but always to the next town over where being "good at it" is generally admired and not fodder for water cooler discussions and snippy comments for many weeks following.


One other thought. When I go out on Halloween these days I'm always wearing a costume. Never just street wear.

[Barbra P]

Like Cheryl, the first time I dressed for an office party I dressed to pass as I wanted to be seen as a woman. I also won the costume contest and the prize was dinner for two at a very nice restaurant. At the party, which started at 1:00 and was catered by the company, I inadvertently may have embarrassed the Director of Data Processing; he came over to me put his arm around my waist, after passing it across my derriere, then in a low voice he asked if I was new or had I accompanied someone to the party, while sliding his hand up until it rested against my bust. My immediate boss came to my rescue and quickly told him who I was – his hand was quickly removed and in a much louder voice he complimented me on my costume. I still chuckle when I think of that encounter.

I met my wife at a Halloween party and I was dressed enfemme then too, and just recently separated from the Marines; went enfemme to a party while in the Marines the year before. Also went to parties while a police officer. One year I attended a party and the Principal from a local Elementary School was there enfemme, looked darn good too, and we entertained the others with a rather risqué impromptu exchange.

[Megan Briana]

This Halloween will be the first time I will be a female-type of costume. I am going with a friend that knows I cd, and her children to do some trick or treating, She has loan me some clothes, and she is doing my makeup. The only bad-tell would be the cheap Halloween wig I grabbed at Walmart. IT is a hideous looking thing, but it will work in lieu of a proper wig. (I am saving up to buy a quality wig). I maybe be outed for walking too well in heals, some mannerisms, and a well coordinated outfit. But I think I maybe using Halloween to be outed. I am tired of dressing this way just at home. This will be my first real time out in public among people, and the jokes can roll off my nicely shaped legs. Whatever happens, I will enjoy it and have no regrets.

Megan

[PretzelGirl]

I think just sheer repetition will get you too. We have an annual costume contest at work. I noticed last year one guy who was dressed up as a caricature (lousy wig, large bust) but I remember him doing it at least the previous year. Thanks to HR, all the contest pictures for previous years were available and I found that this was his fourth year in a row. I am watching for him this year.

[Victoria StJohn]

This Halloween will be the first time I will be a female-type of costume. I am going with a friend that knows I cd, and her children to do some trick or treating, She has loan me some clothes, and she is doing my makeup. The only bad-tell would be the cheap Halloween wig I grabbed at Walmart. IT is a hideous looking thing, but it will work in lieu of a proper wig. (I am saving up to buy a quality wig). I maybe be outed for walking too well in heals, some mannerisms, and a well coordinated outfit. But I think I maybe using Halloween to be outed. I am tired of dressing this way just at home. This will be my first real time out in public among people, and the jokes can roll off my nicely shaped legs. Whatever happens, I will enjoy it and have no regrets. Megan

Megan, with your attitude, I'm sure you are going to have a very enjoyable time out with your friends. Having your friend doing your makeup and loaning her clothes is the perfect excuse if you don't want to come out of the closet. Have fun!!! We will be waiting to see how the night goes. Don't forget to take photos. :D

[Amanda_P]

I get that everytime. Everyone says I walk to good in heels to just doing it once a year. Even if they are only 2". I just tell them you have to walk that way or you will fall off them an I dont want to go to the hospital dressed like this.

[kimdl93]

I've never dressed for Halloween, but not because I feared being too convincing. From the parties I've attended , any time a guy comes dressed as a woman, it kindles some speculation. Mi figured, why invite scrutiny ?

[Annie D]

I kinda consider dressing up for Halloween as a special night for tricks, evil ones at that. Not that I don't dress but I generally go as a female character like Cruella DeVille or the Evil Queen turned into a witch from Snow White. The idea is to be a villanous or evil character so that you scare people because Halloween is the Bewitching Night and the next day is All Saints Day. Dressing as a female is what I do every day and I want to be different on Halloween.

[Sara Jessica]

From the parties I've attended , any time a guy comes dressed as a woman, it kindles some speculation.

At the party I went to on Saturday night, there were two guys doing the dress-like-a-girl thing and neither would make me think for half a second that it didn't begin & end on Halloween. Nothing like the hijinks of a bearded guy in a dress to get everyone going.

I did Halloween 3 years in a row during college and yes, I did the best I could which back then wasn't half bad because I had access to a makeup artist (the girl I was dating) and a model's wardrobe (her best friend). Was it too convincing then? Probably but I didn't get any grief for it.

Nowadays I call Halloween "amateur night", not out of disrespect for those who use it as their first foray into going out in public. No, those people are in it to win it and typically do too good of a job. I'm talking about the dudes I saw at the party, true amateurs with nothing to lose in putting together the easiest costume possible. I therefore choose to sit this holiday out.

[Aylineira]

Just do what I did and put on the witch's hat and grab a broom stick.

[ChelseaErtel]

I've never had the opportunity. But given one I'd go the full nine yards just to get them wondering. I think I'd do a MAC makeover. I would love it. A friends husband, before he came out as a TS, dressed up as women (once as Cat Woman) and I was told looked wonderful. She said she never suspected anything, even when he shaved his chest. Why can't you be good at makeup and look convincing? I say go for it.

[Sara Jessica]

I've never had the opportunity. But given one I'd go the full nine yards just to get them wondering. I think I'd do a MAC makeover. I would love it. A friends husband, before he came out as a TS, dressed up as women (once as Cat Woman) and I was told looked wonderful. She said she never suspected anything, even when he shaved his chest. Why can't you be good at makeup and look convincing? I say go for it.

The thing is, there are 364 other days in the year when a MAC makeover can be just as good of an idea.

If I EVER do the Halloween thing again, it will be in some sort of trans environment in a female costume (rather than in costume that is simply "dressed as a female").

[Beverley Sims]

One time I went dressed in top hat and tails like Liza Minelli in Cabaret.
It was suggested by a couple of girls that I should have come as Fred Astaire with tap shoes because it would have been great to see a girl impersonate Fred.
They thought it would be better for a man to do the Liza Minelli thing than a girl doing it.
Naah! I did not let on. :)
It was a great compliment though. I really wanted to hit on one of the girls but again I was satisfied to be hidden. :(

[Krististeph]

On Halloween several years ago, our office was visited by about 5 costumed employees of a neighboring business. One was a rather petite young man dressed as a girl. Really, a knockout presentation. When the group left, the office was abuzz about him, with many commenting that it was "too good" - "he's done this before" - "this isn't a costume, it's an opportunity" - etc.

Same thing years ago- I really wanted to ask him if he was a CD, but wasn't secure enough, and didn't know him well enough.

[JessicaMay]

Once but I wasn't really dressing then. I was supposed to go to our highschool dance dressed as my (then girlfriend) wife as she was dressed as me (you won't believe me but I used to go to our public high school, in white dress shirts, dress pants / shoes and a baseball cap). Her and a few of her friends made an evening out of it I suppose. Each brought different outfits to try on, experimented with different household objects to use as boobs. After a few hours, it was honestly a good time, I was ready to go out.

I left the building, and started down the path to the nearest road. Someone whistled at me from their balcony. I turned beat red, and ran back inside to change.

Since I started dressing, nope. Don't care if people think I'm a cross dresser, it's the ones that KNOW that matter. Anyway I've been to two dressed as a normal female and one as Sailor Moon. People would talk, and why not? To them it was still just a costume, to me it was so much more.

[Tina B.]

A few years ago, I had three pretty teenage girls come trick or treating at my door, the one that spoke out was really a boy in a dress, the two girls thought it was great fun when people realized it was a boy, but as i watched them walk away, I wondered if they knew just how much he seemed to like, and fit the role so well, it left me wondering about him, and that was just a fast meeting, much less time at a party to give yourself away. If I want to hide it, I have to stay in a male role, I could never look like I didn't know how to walk in heels, or trying to look uncomfortable trying to sit in a dress.
I've seen others pull it off, not sure what their reason for choosing a dress for a costume, but I could never get away with it.

[JenniferR771]

YES! In school, I had a serious day of indecision. My mom wanted to dress me as a woman about 5th grade or so...I really wanted to...however...I thought the other kids would realize how much I liked it, and how natural I walked in heels, and how good I looked as a girl. I would never live it down. I didn't do it and regret it now.
Twenty years later, I got a makeover for my "Halloween" outfit at my hair cutting shop/salon. A year later I did the same thing. I think they were starting to catch on. There was actually no Halloween party, and my wife was at work...she never knew.

[Tracii G]

Not much on Halloween dressing but I love all the costume pics people have posted pics of.
Did a band gig dressed but it wasn't Halloween.

[Lorileah]

The only reason I wouldn't dress is that I am getting bored with it for a Halloween costume. My friends expect it now and want me to top the year before. That is getting harder and harder

[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