Chrossdressmas, Parts 4 & 5: Plans, Trans & Outcomobiles

I’m not even going to pretend that’s a good post title.

I totally and completely apologize for not posting this sooner. I don’t even have a good excuse for the delay. Yes, Hurricane Sandy has taken its toll in my area, but where I live hasn’t been hit very hard, and tomorrow will be my third consecutive day with work cancelled. Instead of dressing up, writing or doing anything productive I marathoned the remaining Doctor Who episodes I had yet to see. That’s all finished, though, so without further adieu…

Welcome to parts four and five of my Halloween/Crossdressing feature. This is the penultimate and ultimate post, as I’ve decided to combine the two due to my tardiness in posting, and the common thread that runs between both parts. In part four I write about my plans for unveiling my crossdressing on Halloween, and in part five I will discuss how it all actually went down.

Part 4: Coming Out On Halloween


End of the Night

Every year my girlfriend and I throw a Halloween party. If you’ve read some of my previous posts, you already know that this would be my third consecutive year crossdressing. The first two times no one takes you seriously, especially if you don’t do it very well. The third time, you’re faced with a choice – no one thinks a three-times crossdresser is joking, so if you’re going to do it, you should do it well. Otherwise, your secret is out to everyone, and you’re also not impressing anyone.

This year, I put a lot of effort into my costume, or rather, my new lifestyle in general. If people had questions, I would answer them all seriously.

First, give them a choice: Do you want the P.C. answer or do you want the serious/blunt answer? This comes into play with questions like, “What did you do with your penis?” or “Can I touch your breasts?” I also assumed people would ask the same questions most others face when they come out. The “Are you gay?” and “Do you want a sex change” fare. Those I would answer quickly and honestly.

At one point I dabbled in writing up a quick one page crossdressing FAQ that I could share with anyone who had questions. I decided against this, as it made it obviously that the issue was clearly something I was nervous about, and had put a lot of thought into. At a party you’re holding, it’s always better to play things casually, even if that’s not how you feel on the inside.

In this aspect, I also decided that I would not broach the subject myself. The point of the party is to have  a party, not to serve as a coming out. If people don’t ask me what I am or why I’m dressed up, I won’t bring it up either. Crossdressing for the third party in a row or not, it’s still Halloween. Maybe it’s just a strange kink, better left unexplained.

So my policy would boil down to:

  1. No ask? Don’t tell.
  2. Honesty when asked for, otherwise brush over the unimportant details.
  3. Play it cool.

Following these three rules would hopefully lead to a peaceful, fun, and freeing night. And if they don’t work – when in doubt? There was alcohol.

Part 5: The Party


Another shot

So how did it all happen? In a word, uneventful.

This years part, for lack of a better word, was small. In the past, parties have had around fifteen people, which is a good amount considering the size of our apartment. Due to weather, health, other parties and an ill-timed Aimee Mann/Ted Leo concert, this year’s party only had half the number of guests as usual, and was therefore more of an intimate gathering than usual.

This did not hinder me, though. My costume worked as planned, plus a few extra pieces of tape and safety pins. Of the guests that did come, two of them already knew about my crossdressing, and the rest simply did not ask. That is to say, they did not ask why I was dressed up. When asked what my costume was, I replied, “A crossdresser on Halloween” and left it at that. I figured that left things open to interpretation or further questions if curious, but apparently my answer was good enough.

I think it was pretty clear that a good deal of effort had been put into the costume – for example, I didn’t just happen to have size twelve boots laying around, or a high-quality wig. If people had any questions, they were all kept to themselves, and short of complementing my costume, no one had anything else to say about it. It was nice to hear from some of the girls, however, that I was pulling off a dress that they couldn’t.

In terms of costume itself, I was very happy with how it came out. I wish I had some more time to spend on my make up. I also want to give props to my girlfriend, who did an excellent job on my eye make up. I’m going to have to ask her for tips on how to replicate that look in the future.

The pictures that I have, unfortunately are from the end of the night, after people had left. I think the costume overall looked a little bit better earlier, but c’est la vie. There’s always next year. All in all, I’d consider it a successful and uneventful night of crossdressing.

Do I wish I had “come out” more clearly? Maybe. I think, though, that I got the point across and would consider it safe to say that more people know now than did a few days ago.


So where do I go from here? Halloween parties aren’t for another year. As a crossdresser, I’ve been looking forward to Halloween since July. Here a few things I hope to look forward to that are not Halloween in the coming months.

  • Going out in public – for real – not just walking around the block. I want to go to a bar with my friends. I will do this. It is new #1 goal. It will happen before the end of the year. Hopefully.
  • New Years – I’ve always wanted to dress up for New Years. I don’t know where this year’s New Years party will be, but depending on the location, and who throws the party, it’s definitely an option.
  • Telling more people – there are more friends that I would like to tell, and eventually my parents.
  • Just getting better at crossdressing in general. In one of my first ever posts I likened crossdressing to a sport. In this case, there’s always room for improvement, and I can think of hundreds of ways I’d like to get better.

I will save elaboration on all of these for other posts. Don’t want to stray too far here. I will say, it was a lot of fun writing about Halloween. Next year, I don’t think there will be any multi-part feature – that’s kind of a once in a lifetime thing. As for next year’s Halloween? I eagerly await it.

Happy Chrossdressmas!


More Pics on Flickr

Hello all! I know, I’m past due for an update, and the last two parts of my Crossdressing on Halloween post collection. They’ll come soon. A bit exhausted right now, from running a 10 mile race yesterday, and hosting a Halloween party. There are way more pictures on Flickr for mutual contacts – you add me, I’ll add you ASAP.

For now, though, I’m going to sit back, eat some pizza and enjoy the fact that inclement weather has closed my school for tomorrow. The only people that want school closed more than the students? The teachers.

Enjoy your Halloweekend, all!


Chrossdressmas, Part 3: *Some Assembly Required

This is the third part of my Chrossdressmas series, which goes into way too much detail about my love affair with Halloween, as a crossdresser. The first two parts of the series deal with my past experiences on Halloween, and what Halloween means to me as a crossdresser. With the third installment, I will discuss this year’s Halloween costume and how it came to be. Let’s begin.



She’s more muscular than I am

As I mentioned in an earlier post, I began thinking about Halloween in July, as soon as I came out of the crossdressing closet. Within a week of telling my girlfriend I had a folder in my bookmarks that was filled with a number of different crossdressing ideas.

My first plan was Supergirl – one of the few female superheros with long sleeves. This costume could be put together pretty easily, but wasn’t very do-it-yourself, which is something I prefer in a Halloween costume. I still like the idea of a Supergirl costume, but I decided it wouldn’t work this year. Now that I was out, I wanted to do something that could show off how successfully I could do it. (This is debatable, opinions to yourself please.)

Costume: Dress

6pm Dress

Nice, but not curvy enough.

I moved on from Supergirl to simply “classy Halloween dress.” I knew I wanted it to focus on the colors black and orange, and I also wanted it to show off some of my curves. I narrowed it down to three different dresses, and eventually purchased a dress from The dress, pictured left, arrived, and was quite nice, but in the end I decided it didn’t do enough for my end. If it’s Halloween I’m going for wow.

From here, I moved onto to American Apparel, which I now known is known for selling clothes that fit better on trendy hipsters. I am not a trendy hipster. I did however, purchase a dress from them, that was revealing and showed off curves. I loved the plunging neckline in the back and front. (Note – the dress I purchased was in black, not sure what color that link actually goes to…) The only problem with the dress? With my breastforms, the bra is necessary and it shows quite obviously along the back. I’d met with failure once more.

Fortunately, American Apparel has a very similar dress, which I posted a picture of earlier from their site. The is short, black, with a plunging v-neck and a high back. It’s just a bit longer than the original American Apparel dress and it looks like this.

The Final Dress

This Is It

So at the moment, less than a week before my Halloween party this is the dress I’ve settled on. Plans can still change, though. I still like the 6pm dress, and if it wasn’t for the back of the first American Apparel dress, that would be my choice. I do have an invisible strap bra, but it doesn’t work very well with my breastforms and it isn’t very supportive. I’ve still got time to figure things out, though.

Costume: Belt

The costume, of course, needs some black and orange, and what better way to include some orange than with a waist cinching belt?

Finding a decent orange belt has not been easy. I’ve gone through three different belts, and finally the third belt is the one I’ve settled on.


Not Orange Snakes

The first belt has a bit of an orange and white weave, and just didn’t feel right. It looks a little bit too springy, and it didn’t close very strongly. A cheap belt off of ebay, and ultimately a mistake. The second belt is too short and too skinny – also very cheaply made.

The third belt is essentially a larger version of the second belt. I didn’t want a skinny belt – I didn’t like the way it looked. This ended up being the right call, as the thicker belt looks much better with the dress. In addition, it fits much better. It’s crazy how different sizing a belt for myself en homme and en femme can be.

Costume: Shoes

Just like everything else, my shoes for this costume has gone through phases. This one will probably come down to a decision on the day of the Halloween party.

The first shoes I ever bought myself were cute little Mary Janes from Payless. I thought this would be functional, and also an option for Halloween. This is still the case, but this was all before my mini-obsession with boots. The next option is my calf-high black boots. These look good with just about anything, and love the idea of a short dress and high boots. These are probably my top choice right around now. I also purchased my first pair of heels as an option for the costume…. but I also realize heels are extremely uncomfortable, even if they’re considered the comfortable heels.

All Shoes

All Shoes

No matter which decision I make, I’m pretty confident they’ll look alright.

Costume: Jewlery

For necklace, I think I’ll be wearing a cute black choker that belongs to my girlfriend. For earrings? Check this out:


Trick or Treat

The earrings are from Ashla Designs on etsy. Do note – I ordered the earrings as clip-ons and they were sent as regular earrings. I contacted the maker, and she’s sending me replacements, and an extra pair of clip-ons to apologize for the inconvenience. Once the replacements arrive, I will have no problem giving etsy and Ashla Designs my vote of confidence (and high seller marks.) Very good customer service, and awesome looking earrings. Win-win.

I also have an orange flower hair-clip from Claire’s that I’m excited about trying out. Forgot to snap a picture of it – sorry!

Costume: Make-Up

Orange lipstick, dark eye-shadow. I considered finding a place to get my make-up done professionally, but I can’t find anything extremely local, or anything fairly cheap. I’ll do the make-up myself, or perhaps get a friend to help me out. We’ll see.

Everything else for the make-up will be pretty typical. I’m going to get a professional shave a few hours before hand, so hopefully I’ll be able to more successfully hide any stubble.


That about sums up my costume. Finished pictures will obviously be posted next weekend after the party. I’m excited to try everything out all once… I’m also very nervous about dressing up around a lot of people who have never seen me dressed up before. I’ll go into much more detail with that next week, though, as part four of my Halloween expose is about my non-dressing plans for Halloween. This will talk much more in-depth about who I will probably be coming out to, how I’m going to do it, and how ridiculously nervous I am.

All in the name of crossdressing!

Now, though, it’s time to try out my new wig. Wearing it en homme I just look like a confuses samurai.

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!