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.