Chrossdressmas, Part 2: The Meaning of Chrossdressmas

This is the second part of my Chrossdressmass series, which analyzes my relationship with Halloween as a crossdresser. The first part of the series catalogs my earlier, less successful forays into crossdressing on Halloween and can be found here. Part 2 will follow what exactly Halloween means to me as a crossdresser, and what I think it can mean to other crossdressers. After rereading some of my earlier posts, I think I should warn: I’ve gotten awfully assumptive these days.

Me (A semi-outed heterosexual MTF crossdresser)

Crossdressing has meant a number of different things to me over the past few years. The past two years when I crossdressed on Halloween I did so as a joke. At least, that was the spoken explanation. To myself, a then closeted crossdresser I looked at the day as an opportunity to express myself in public physically, but not mentally.

Halloween is all about costumes and glamour. It’s the day where everyone wants to dress up and appear as something they are not. Except as a crossdresser this is really how I feel almost every day. There isn’t a day that goes by where I don’t wonder how I would look in a pair of boots, or in a certain dress. Most days, before coming out, figuring out just wasn’t an option. Halloween served as a built-in pressure release for closeted crossdressers so that once, every year, they could express themselves and nobody would think anything of it.

In terms of my relationship with my girlfriend, crossdressing on Halloween also served as a way to test borders and boundaries. I used Halloween to gauge my girlfriend’s reaction to crossdressing. I will admit, it’s tough to discern the difference between accepting crossdressing and accepting crossdressing as a joke, but there was certainly the possibility of an overwhelmingly negative reaction. When I crossdressed the past two years, my costumes were met with a mix of eye-rolling and genuine help in terms of creating the costume. Not a negative word was spoken, and this certainly made it more okay for me to come out when I eventually did this past summer.

Now crossdressing on Halloween means something entirely different to me. It’s a year later, and at the time that this is being written, not including myself, six other people know I am a crossdresser. This Halloween I plan to increase that number significantly. As I’m going to be myself (Justine) for Halloween this year, combined with the fact that it’s my third year spending Halloween in a dress, it’s about time that people stopped getting the hint, and had the information handed to them on a silver platter.

Anyone who attends my annual Halloween party this year will leave knowing that I crossdress. I’m not exactly sure how I’m going to about it yet, but I have a few ideas that I will go into more depth about in Part 4 of the series later this month.    I’m not sure if Halloween, while dressed, is the perfect time to come out, but I at least it’s a semi-controllable situation that I know has an end point.

You (a closeted crossdresser)

This part is easy. Do what I did! Have fun with Halloween. Use it as an opportunity to test some waters, and enjoy yourself. If you’re going to remain in the closet, you might as well crossdress on the one day that you’re actually “allowed” to. What’s the worst that could happen?

You (an outed or semi-outed crossdresser)

Push the borders of crossdressing of your crossdressing. Do something you normally wouldn’t. This year I’ve got myself a low-cut dress, which is quite revealing. I’m looking into getting my eyebrows threaded, something I normally wouldn’t do, and I’m also going to get to have nails for the first time. I’m also going to begin to do some research as to whether or not there are any small stores around my neighborhood that will help out with makeup, under the guise that I’m “jokingly” doing it for Halloween. I’ll have more information on all that later, though.

I think Halloween works great for out crossdressers, simply because it’s Halloween – you’re supposed to do something crazy and fun. In Part 1 I discussed  the question of whether not simply crossdressing in your regular clothes constitutes a costume or not. After even more consideration, I think that it really depends on where you are in your stages of crossdressing. For me, it’s still new and not a lot of people know – so in a way, Justine is just a costume to most. Next year, however, I’m definitely going to go the traditional costume crossdressed route so that it’s not male me dressing up as Justine for Halloween, but Justine dressing up in costume. If that makes any sense.


Okay – this post wasn’t as organized as I originally hoped. I don’t know if I was short of things to say, or my brain just wasn’t in the right place for writing at the moment. Regardless, I hope everyone who reads this can take something from it, and have a terrific Halloween that is meaningful for them. I’m exactly two weeks away from the date of my Halloween party and will probably post the next two installments on the next two Saturdays. Part 5 will be an after-Halloween post with pictures and a summary of the party.

I’m dressed right now in a short woolen dress with panty hose and I’m happy with how I look. This makes me kind of anxious to go for a walk outside. It’s still light, though, so we’ll see in a few hours.