Halloween – The Crossdressers’ Christmas

halloween-crossdresser-christmas-bannerreprinted from an October 2017 post…

Halloween is not only about putting on a costume, but it’s about finding the imagination and costume within ourselves.

~ Elvis Duran

Many have designated Halloween as that one American holiday where closeted male to female crossdressers get enough courage to venture out of the house dressed as a girl. A sexy girl… the gender-bending female half of a couple’s costume theme… an exaggerated cartoony parody of what they think a woman in costume would look like. Since it is fast becoming synonymous that closeted CD men use Halloween as an excuse to publicly costume as a girl, that common knowledge can be a double-edged sword.

What will people say? Will they assume that the man is dressing as a parody… or outing themselves as a crossdresser… with their feminine costume?

Of course, two of the examples stated above allow for the crossdresser to skirt (no pun intended) under the radar of co-workers, friends and family members who may get the “wrong idea” about their pal dressing as the opposite gender. Being a part of a funny gender-swap couple’s costume theme (Sonny and Cher, Mark Antony and Cleopatra, etc.) can cast doubt into outside speculation because onlookers see that woman is fully onboard with the theme. Therefore, the woman must be in on the gag.

And that concept – the gag – leads to the second costume choice. Dressing up as an over-feminized or exaggerated version of a 1950s housewife, Jessica Rabbit, or other classic female standard characters is typically viewed as parody. If you strut around with jokes and confidence, no one will automatically assume your true intentions.

Of course, if your make-up is flawless or have all the proper curves too well positioned and defined, it is possible that you will be accused of being a drag queen or crossdresser. And, if you are like me, and you dress as a female character every year, it may become more and more evident by some that you have a preference for a certain feminine style. I remember dressing up as part of a four-person theme where the two women dressed up as pimps and me and another male co-worker dressed as their hookers. One of the graphic designers in my department helped me with my eye makeup, remarking that I was so easy to work with – especially with her eyeliner pencil so close to my lashes and waterline.

Ironically, it was very difficult to “unlearn” my makeup skills for that day. I struggled to dumb down my make-up application in order to not draw too much attention to myself.

There were statements of “I can’t look at you while you’re dressed that way”. I wasn’t too happy about his comments he said directly to me, but what was worse was when he reiterated the same sentiment to my girlfriend when I was not within earshot. Aside from that, there were other more positive surprises. One member of the international department put hard candies in my top to create more extruded nipples for his camera selfie. Another male co-worker actually slapped me on the ass – a complete surprise that was out of character. I took it all in stride. Now, in recent years, other members of the company have commented when they were disappointed that I didn’t wear something more feminine or more outlandish. Go figure.

As in life, this type of quasi-“coming out” during Halloween festivities is a way to embrace the feminine side of yourself that may be shackled during other parts of the year without the stigma of revealing your true authentic self to the people around you. Or it could be a way to ease your feminine side into a more exposed level of existence. How you believe you are received and how you want to be perceived is up to you. No matter what, be confident. Be the person others have already come to understand. While wearing a costume may make you feel different – more sensual, more confident, more powerful – be sure to always embrace the best parts of yourself.

Author: livingwithcrossdressing

I am many things. I am a life-long male-to-female crossdresser and author. I hope my journey is of value for those who may need help to foster, support, and understand who they feel themselves to be.

2 thoughts

  1. Age 14, I went out raising hell with my Catholic school male classmates on Halloween. One of the guys had his mom & sisters dress him up, and do the makeup. He/she looked presentable. I was fascinated by it all. I would fantasize about being a girl as I played with my nipples back then. The earliest signs of my budding cross dresser.

  2. To a large extent, attitude makes all the difference. “I’m afraid of what other people think,” other people will very definitely have opinions. “People better not mess with me, ” you come across as angry or hostile. The best attitude is, “This is also me.” This is another side to how I am. I’m that hard-working man who keeps everything done. I’m also fabulous looking in this costume.
    I’ve noticed ppl treat me differently based on my attitude.

Leave a Reply