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.

Chrossdressmas, Part 1: A Halloween Carol

Before you read any further take note: I have fallen in love with the term “Chrossdressmas.” You can complain all you want, but it’s here to stay.

Welcome to the first installment of my Chrossdressmas posts. As denoted earlier, this will be a five part series that details the many aspects of Halloween and my relationship with it as a crossdresser. The first part will focus on Halloween’s past, present and future.

Past 1

Close your eyes and think back to a time when “Bruno Mars” was first becoming a thing, people laughed without irony at Cee Lo Green, and the Mets still sucked. Yes, that’s right. October 2010. Let me more personally set the scene.

My girlfriend and I are shpping for Halloween costumes, with just a few weeks to go before the event. At one of the local seasonal Halloween stores, I suggest to my girlfriend that she dress as Robin from How I Met Your Mother, or more specifically Robin Sparkles, the 90s teen popstar persona that Robin had back in Canada. She laughs at the idea, but rejects it. She wants something a little bit more creative. (We always make our own costumes – always.) I jokingly suggest that I would be Robin Sparkles instead.

Now – let me stop here and place special emphasis on the word “jokingly.” If a guy “jokingly” suggests that he crossdress for Halloween, this is a very strong sign that he is interested in crossdressing in general. I admit, I have done no scientific studies, and this cannot in fact be proven. It just makes sense. Most guys don’t want to give up their gender-given privilege, even if for a night. Girls, if your boyfriend or husband “jokingly” suggests crossdressing on Halloween, he is at least somewhat curious as to what it feels like to wear your underwear. Halloween is how he is not-so-subtly telling you.

After suggesting that I go as Ms. Sparkles, my girlfriend laughed. “No, I’m serious – I think I could pull it off, how easy could it be,” I said jokingly. (Side note – that’s a definite sign!) I quickly searched for a picture of Robin and listed the clothes I would need. Frilly petticoat, fishnet stockings, pink shirt, denim jacket, wig. Anyone could do that.

We browsed the store for another half hour or so, picking up the items we could find, and I left the store with everything but some neckles, the pink shirt, and the denim jacket. I will mention, for honesty’s sake, that at this time crossdressing for me was very much a fetish, and I spent the majority of this shopping having to hide an erection at the idea of crossdressing on Halloween.

Robin Sparkleses

Can you tell which is the real Robin Sparkles?

At home, I ordered a denim jacket online. We picked up the shirt at Walmart, and the neckles at Claire’s. The costume was set.Halloween arrived. I was Robin Sparkles, my girlfriend was Christine O’Donnell. (It was 2010 – Google it if you don’t get it.) When getting dressed for our annual Halloween party, my petticoat housed another erection, and this time my girlfriend noticed. I laughed it off, making a slight remark about how the fishnets was a bit of a turn on. Nothing crazy. Girlfriends/wives of the worlds, please take note again: If your boyfriend/husband is turned on by women’s clothing, there’s a good chance he’s a crossdresser.

Past 2

Fast forward to 2011. Bruno Mars is still probably a thing, people begin to question what they ever saw in Cee Lo, and yes, the Mets still suck.

Halloween is once again fast approaching. For the first time, my girlfriend and I live together! We’re again hosting a party, and of course, two days before Halloween I still don’t have a costume. At least that’s what I’m telling people. Here’s what’s really happening.

Now that I live with my girlfriend my crossdressing habits have jumped up a notch. When she’s out of the house I have a wonderful wardrobe of clothes that, guilt or not, I like to take advantage of. My first idea, months before Halloween, is to dress as a sexy cat. I can find some curves and fit into a skin tight black body suit. Get a wig, a tail, some ears. A simple and sexy costume. I order off of ebay a butt-booster/waist cincher. It’s mailed to the house, and when it arrives, I tell my girlfriend it’s just a boardgame I’ve ordered online. I hide the package away discreetly. At Party City I purchase a black body suit. When the time comes, I try everything on. It actually doesn’t look too bad….. but it doesn’t feel right. I think it might weird people out, and besides, who crossdresses for two years in a row?

Jump back to two days before Halloween. I still want to crossdress for Halloween, but I don’t know how. I decide that I’m going to bite the bullet, and tell my girlfriend that I’m going to be a hipster for Halloween – a hipster chick. I tell her the inspiration came when I was at the 99 cent store and saw a cheap hipster fedora. This is only a partial lie. The hat really did inspire me, but I set out looking for something to claim as inspiration.

Using a mixture of my girlfriends clothes, my own clothes, and a few other things from the 99 cent store I semi-hastily assemble a costume. This year I have a nicer wig, and even use a little bit of lipstick.

Bathroom shot!

What a hipsteriffic self-shot!

Halloween comes, and I dress. A few comments are made about how I’m crossdressing two years in a row. Girlfriends/wives, pay attention here: If your boyfriend/husband crossdresses two years in a row, he is a crossdresser. I don’t think I need scientific evidence here.

That night, after de-costuming, for the second Halloween in a row we have really mind-blowing sex. I stay up most of the night, wondering what would happen if I told her I was a crossdresser. I post the hipster-me picture on Facebook and it’s met with a few comments/likes. Crossdressing  never comes up.


Now we’re here. 2012. If you’re reading this in 2013, think back to a time when Bruno Mars was quickly fading, Cee Lo Green was somehow still a thing, and yes, the Mets still suck.

This year is different, though! This year, I’m semi-out-of-the-closet! Hooray! When I told my girlfriend I was a crossdresser back in July I immediately began working on a Halloween costume. In all seriousness, by July 17th I had a folder in my bookmarks called “Halloween” with a link to at least six different ideas.

One of the main things I was looking, and will probably always look for in a Halloween costume (and while crossdressing in general) is long-sleeves. I narrowed my options for this year down to either Supergirl or Sexy Black Dress. I’ve always wanted to try my hand at Super Girl, and most definitely will one day, but this year I was going to give it my all.

I want to focus more in-depth on the assemblage of my costume in a future post down the line, but I’ll describe the final version here. Long-sleeve black dress. Plunging v-neck. Black heels. Orange belt. Probably some Halloween themed jewelry. I’m going to go into a lot of depth about the choice of the costume, and the evolution of the costume in part three of this series, but for now I’ll just leave you all with an image of the dress. It’s from American Apparel.


This is it.

Part four of the series will go into more depth about the following subject, but I do want to touch upon briefly my ultimate plan for this year’s Halloween party. We’ve invited just over twenty people to the party. I expect at least ten of them to show up, and most of them do not yet know that I’m a crossdresser. At this point – it might be obvious. Three years in a row, you know? Regardless, anyone who asks me about the costume, I plan on being blunt with them and saying the following. “Yes, I’m a crossdresser. No, I’m not gay. Yes, my girlfriend knows, and she is supportive. If you have any more questions, feel free to ask.” I hope that will sate them, but I plan on being as open and honest as possible if anyone has anything to ask.

What I want to avoid is a hijacking. I don’t want my crossdressing to be the focus of the party. The party should be about Halloween, drinking and having fun. Not asking questions to a crossdresser. I also hope that I don’t weird anyone out. Being around others while dressed, I’m always worried that I’m making them uncomfortable. This is something I hope will be solved, and not exacerbated, by a few drinks.


Flash forward. Not the terrible TV show, but 2013. This year, Bruno Mars is the ironic name of somebody’s dog. Cee Lo Green has died in a terrible dirigible accident, and yeah, the Mets still suck.

I don’t know what Halloween 2013 holds. I think a lot depends on how this year goes. I think Super Girl is definitely an option, but I don’t want to be locked into any ideas this early. Regardless, at this point, I don’t see the point in not crossdressing on Halloween. It’s a night where I can be myself and everyone’s more okay with it than usual. In a post over at Crossdressing Commentary, Jess mentions that crossdresing in my regular women’s clothes is kind of strange, because they’re not a costume, they’re me. After some thought, I agree with this statement philosophically, but I also understand that to most other people, it still is a costume. Therefore, I don’t really have a problem with crossdressing in my normal clothes for Halloween.

Until crossdressing is socially acceptable at the level that I do it, I’ll be glad to have just the one night of acceptance, where I can throw a dress, put on some heels and just relax.


So there it is. Take that, Dickens. Part two of the series will focus on what Halloween means to me as a crossdresser. I definitely touched upon that a bit here, but I have some more thoughts on the subject that I’m sure you’re all dying to hear.

In the meantime, a few brief notes:

  1. Hello anyone from r/crossdressing! I finally posted some pictures on there and it seems to have gone over well.
  2. There are some new pictures up on Flickr as of an hour or two ago.
  3. The tablet that I used to take almost all of my pictures broke today. (I had it in my back pocket and sat down.) There is a warranty, but it will probably take some time to ship over a new one. I’ll try to use my regular camera for the next few photos, but I’m not the biggest fan of it.
  4. If you add me on Flickr as a contact, I will try my best to add you back as soon as possible. If the account you create has no information on it, and I don’t know who you are, I probably won’t add you back. Let’s not be strangers.
  5. Shaved legs are still awesome.

With that said, I will go before I bore you to death. Also, it’s quite late and I have to be up early. Goodnight!