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.

Coming Out Cross

(Originally written July 14th, 2012)

I haven’t written a blog post in a very long time. I am inspired tonight, because I am more relaxed than I have been in very long time.

Last week I told my girlfriend of five years that I enjoy crossdressing. We were trapped in a car, with five hours on the road ahead of us and if ever there was a time to hash things out, this was it. I didn’t set out to bring it up just then, however, so let me back track.

Being in a relationship for five years is hard. It’s worth it, but it’s hard. It ebbs and flows, just like everything else in life. We were stuck in a bit of a trough, and I knew exactly why. I had been very quiet; more introverted than usual, and didn’t seem myself. When my girlfriend went away for a week I secretly indulged myself in a crossdressing purchase that took my interest further than it had ever gone before. Silicone breasts, butt and hip pads, a gaff and bra.

This would be my test – how I handled, and felt about this purchase would decide for me what my next step as a crossdresser would be. If I was simply sated I would stop where I was. But by this point, you might realize how this turns out. I loved everything. Yes, I had worn women’s clothes before, but this was something else. The weight of the breasts on my chest, the shape of my body in the mirror – I didn’t want to stop, and I knew I had to tell her – but I didn’t know when or how. Instead, I clammed up.

Fortunately, she decided to ask me, fairly bluntly, what was up and why our relationship had seemed to have stalled lately. Initially, I told her that I would tell her after we returned from our vacation, and promised her that I hadn’t cheated on her, wasn’t breaking up with her, or doing anything “bad.” She understood, but apparently I didn’t. I explained again, that I would tell her now, stuck in the car, as long as the conversation ended when we left the car, and could continue after we returned from our vacation. She signed on the dotted line, and I let spill.

I told her that for the past ten years I have fetishized crossdressing. I told her about that the guilt that had been I had been wracked with (increasingly) for years. I told her how I am not gay, but still enjoy women’s clothing. I told her that this was the true reason I had gone to a psychiatrist in the past. And I profusely apologized to her for doing it consistently (and frequently) in her clothes in the past year that we have lived together.


She took this all well. She told me that she knew, to an extent, that I enjoyed women’s clothing. (I have crossdressed the past two Halloweens, and brought up that enjoy the feel of her clothing.) She did not realize to what extent this was, though, but she was okay with it. And, to my surprise, she enjoyed the fact that I did it in her clothes. She had questions, obviously, and I encouraged them (and still do.)

It was good to hear her questions, too, because it forced me to think about certain things that I hadn’t before. She wanted to know exactly how much of this was a fetish, and what extent she should be involved in this.

Now, I’ve been thinking about these things, and I think I have a clearer answer now than ever before. When originally began as an accidental fetish the summer going into high school, has become more of a hobby than anything else. Yes, I am still quite turned on by the idea of crossdressing, but now I enjoy the sport of it. I want to challenge of being “passable.” I want to learn how to mystify with transformation. I like the enormous variety of clothing women have to choose from – the challenge of putting together an outfit and finding out what looks right. It’s strange – as a guy, all I care about is comfortable clothes and sometimes a nerdy t-shirt, but as a girl I want to look good and fashionable.

In terms of her involvement, that is something that has to be a two-way street. I want her to be involved, and I want her to want to be involved. That is something that will maybe, one day, come over time. It’s completely her choice. I know that she will accept me no matter what, and her comfort with my crossdressing is something that she has to be in control of. I will try to ease her into it, at a pace she is okay with. For my birthday she is going to buy me my own underwear and that makes me smile.

At this point I don’t know how comfortable either of us is talking about it. Right now, I’m the only one who has really brought it up on a few occasions. I showed her my silicone breasts, pads and gaff. She even let me put on the breasts to show her. She was weirded out, but not as much as she thought she would be – that’s good. I also sent her some links to other blogs that discussed why men crossdress, and one from the perspective of a crossdresser’s wife. Today I told her that I just purchased a new wig – a higher quality one that wasn’t bought in a Halloween store. I want to be able to tell her these things, because it’s not a secret anymore. I want to be able to comfortably share everything.  I am a crossdresser and I need to be more openly comfortable talking about that. I hope that soon, she is okay talking about it, too.

I’m going to ask her to read blog post tomorrow for a few different reasons. One, I feel much more comfortable pouring my thoughts across in writing than speaking. I also want her to know that despite everything being out in the open now, I still feel, to a degree that there is some discomfort in the air on this subject, and that is okay, expected even. I am glad to have told her, but that does not mean I am automatically happy about myself. To a large is extent, this is still something I am going to have to cope with in terms of how I feel about the subject, and how she feels. Nevertheless, I am very glad my crossdressing is out there now.

As an extremely amateur stand-up comedian, I love the idea of callbacks and think they apply to blogs too, so I want to end by emphasizing again how relaxed I now feel. My burden of the past ten (almost eleven) years is slowly lifted. There are now two people that I know know about my crossdressing (my girlfriend, and a good friend I told a few days before her.) Maybe in time I will be able to tell more people.

I have set some crossdressing goals for myself, and I find writing out a to-do list helps me better accomplish things, so here it is.

  • Buy make-up
  • Pratice putting on make-up this summer
  • Eventually get kind-of good at putting on make-up
  • Buy my own clothes (perhaps this summer)
    • longer-sleeved light sweaters, to hide my hairy arms
    • shirts that are not low cut, to hide my unshaved chest
    • shoes
    • Shave my legs and chest (for Halloween)
      • This would be a big deal, and I would have to time it right, as I am in a race on 10/27.

Writing all of this down feels good. It’s been too long since I’ve collected my thoughts this clearly and it needs to happen again. Look for my next future blog posts to include:

  • Humorous anecdotes
  • My introduction to crossdressing
  • Early crossdressing experiences
  • My appreciation of other crossdressing blogs
  • The power of imagination
  • My fascination with the idea of how a fetish can become a hobby
  • Some apologies
  • And hopefully updates on my progress as a beginning, out-of-the-closet CD.

It’s late now, though. Goodnight.