October is upon us and cross-dressers everywhere are looking forward to one special day, Halloween 2009. As you would all agree, this is practically a holiday in the transgendered community because of the freedom of expression afforded to anyone who chooses to step outside of the box and into a disguise.
Have you circled this date on your calendar in the hopes of dressing en femme?
Ghouls, goblins, monsters, and …. trannies? This is pretty much the only time of the year that you can put on a costume, walk the streets and have a great time with little to no fear of danger. Though I have to say that I’m always disappointed as it seems that each year less and less people my age dress up. This probably has to do with them “growing up” and forgetting how to have a good time.
When I was a kid we always looked forward to October 31st because there were always great characters to masquerade as. Then, in college, things kind of dwindled down. I noticed that most girls started using Halloween as an excuse to dress slutty instead of putting forth the effort to put together a costume. Guys were no better about it, as they would frequently say something to the effect of, “I’m dressed up as myself”, all the while relishing in their imagined razor sharp wit.
Unfortunately for me, I have never used All Hollow’s Eve as an excuse to dress up, whether as Jessica or some female character. The closest that I ever got to drag was in elementary school when I went as aTeenage Mutant Ninja Turtle (Michelangelo) and topped off my look with green pantyhose.
Each year during college I was determined to do drag for Halloween or at least use it as my alibi to go shopping for women’s clothing. Alas, those things never came to pass. As a matter of fact, I’ve only been in costume once for the past ten or so Halloweens.
This brings us to a great point, though. Take advantage of this time to buy clothes, whether in a regular clothing store or a costume shop. In the former, you can always have the Halloween costume cover story and in the latter you will most likely not even be given a second glance.
For those on a budget, you’ll be happy to know that some ‘big box’ stores are now carrying wigs for dirt cheap. By the same token, female costumes aren’t expensive either, so be sure to check that out if you’re in the market for some new stuff.
So, how will October 31st, 2009 shape up for yours truly? Only time will tell, but no matter what happens I will keep you updated. It certainly would be a fun time and my wife fully supports the idea, but we’ll have to see if there are any parties or events that would fit the bill.
What are your Halloween crossdressing stories? I’d love to hear about your escapades either here in the comment section or via email. Do you plan on assuming a female identity this year? Or maybe you plan on going old school with a Wolfman or Dracula outfit? In any case, happy October girlfriends!!
JessicaWhoHD
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{ 18 comments… read them below or add one }
Keep us updated on how your halloween goes girl! I wanted to dress up as Belle (from Beauty and the beast) but can’t really afford it right now so maybe next year =)
I will girl, Belle would be an awesome costume for you, I hope you can do it next year
I always hoped to use Halloween as a reason to get dressed. Over the last few years, however, I feared others would see my actions as less than serious concerning transition. It came down to asking myself, “Is THIS a costume I’m wearing or would that be compromising my own values?”
Yeah, I get it, it’s supposed to be a night for people to have fun, so maybe I should have dressed in male clothes and told everyone , “I’ve always lived in the costume of maleness.” I’m sure the day won’t be taken as seriously as I did by everyone else.
Now that’s clever, I definitely get that.
Well said.
It’s a good point about compromising values, kind of like doing blackface or something. We want to be taken seriously and as such want to be careful in choosing how we present ourselves no matter what day it is.
My days of going to Halloween parties are long over, but even when I was still young and liked to go to parties, I never crossed dressed on Halloween. Not that I didn’t want to mind you. I was just afraid that my presentation would be so realistic, that people would suspect it wasn’t just a costume, and of course they would be correct. I mean, how does an ostensibly straight, single guy explain to everyone, how he was able to perfectly apply his makeup, immaculately manicure his nails, put together an elegant feminine outfit, and walk comfortably and proficiently in four inch heels all evening, when half the natal girls at the party can’t even do that? They would be bound to suspect that it wasn’t the first time you had done any of that. The only males I knew who were able to pull off crossdressing on Halloween without being suspect, where the ones who didn’t know how to put it all together, and looked funny in their female togs, rather than pretty. I could never do a funny sloppy female presentation. To me, that would be being disrespectful to myself.
Melissa
Melissa, what a terrific comment. I completely relate because there were times when I wanted to dress up but thought it would give me away because I had everything from wig to underwear to makeup — when most guys dressed on Halloween they wore short skirts but with guy underwear and no makeup and a crappy $2 wig.
Last Halloween was the first time that June out,It was to a dinner/parter hosted by a shoe and clothing stores which ar tgfriendley.I had a wonderful time,did not dress in a costume,just a nice dress,etc,had my first makover also.I had a great time and plan on going to the dance this year also.
What a great experience, thanks for sharing that June
Last year was the first time I ever got to do Halloween right, instead of having to settle for dressing male. I’ll have to admit though, I did kind of use it for an excuse to dress slutty. LOL!
I went to Louisville with some of my best friends and boarded a LGBT riverboat cruise! There was some outrageous costuming and it was such a great time.
Me and my friends decided to do Alice in Wonderland costumes, and I ended up as the lady version of the Mad Hatter. I think to this day it is still the most outrageous thing I have ever worn. But this year I’m probably going as Cat Woman. Its going to be so fun!
Wow that’s so cool, I would love to see a picture of that if possible (mad hatter)..Have fun as Cat Woman
I have been lucky enough that for that last 2 years I have dressed fem for Halloween. The first time was shortly after coming out to my friends via Myspace. I dressed in a very sexy princess costume that was very short. Last year the party I went to had a theme It was a vampire party and I went as a Werewolf cheerleader (because every vampire party needs a random werewolf. This year however I am going male and going as Nickola Tesla. The theme is favorite dead person. I thought about going as Jackie O but changed my mind. However I might go back to it if I cannot find the right type of gray suit.
Very cool, Gaven. I just watched your vlog where you describe this and I thoroughly enjoyed it as usual. Thanks for sharing
Referring to Lori’s question “Is THIS a costume I’m wearing or would that be compromising my own values?”, I can tell you that cis-girls certainly also have fun wearing costumes!
(And fortunately the guy did not become angry …)
Also, wearing a female costume and unexpectedly _not_ being read once was a great experience to me: A couple passed by, and he said that I’d look great. I thanked him in my male voice and smiled. His girlfriend had a real laugh about his surprise
So you passed as a couple passed
… very cool
I have sooo many outfits I want to wear but i know i must choose just one.I plan to go to a halloween party as a “hooker” as 4 yrs ago I went as a gothic school girl and it was sooo much fun as I wore black pantyhose with a layered shirt effect and a dark plaid pleated skirt with knee hi black boots with just a 2 inch heel.This year i will wear a short(mid thigh length) denim skirt with black crochet fishnets over black or tan pantyhose with 4 1/2 “hi heel boots and a few layered fem shirts and a brunette wig and dark glasses, or i might get brave and wear a denim mini skirt.I will wear dark mascara and eye shadow with red lipstick and paint my nails purple or bright blue.
Wow, have a great time Kelly, sounds like you really know how to party on the 31st
!
I love halloween, but it got pretty dangerous for me this past Halloween of 2009. I was dressed up all cute like a schoolgirl….short skirt, pantyhose, high heels, knee sox, and a silky top. These two kids come to my door, and immediately they got perverted. They weren’t more than 13, but one was really tall, at least 6ft or more, and I’m only 5’4″. The tall one says “invite me in for a treat” I said “no” and started closing the door, when he swung it open, grabbed me by the arm, and pulled me outside, and slammed me against my very own house. Everything happened so fast, the only thing I could think to do before it got worse, was to take my heel, and stomp his foot……..guess what? It worked. And I safely got back inside and called the police. Not sure if they ever found him or not, but boy it certainly was scary…….I thought my heart was going to pound out of my chest. Now i constantly watch over my shoulder.
I went as the evil queen last year…wore a lovely black/gold gown, marie antoinette like wig, stilettos boots, elbow length gloves. went all out on the makeup..white pancake makeup, purple eyeshadow, black eyeliner, thick mascara, false eyelashes, dark red rouge, dark red lipstick. Also wore purplish false contacts. Had a blast…will likely do this again this year