October is here, and we all know what that means! October 31st is right  around the corner, and yours truly, like many of us, think of Halloween as unofficial “Crossdressers Day,” and with good reason. Most of us have struggled, sometimes for many years, with wanting to get out in public as our femme selves, and a night where it’s acceptable to dress up as literally anything you want is just too good to pass up. Even still, when you know that dressing up is more than just a costume, it takes a staggering amount of courage to go through with it. Many of us also like to use this as a way to “test the waters” with the wife or SO, thinking that you can gauge potential acceptance by how she reacts to you dressed as a woman (a faulty line of thinking, which I’ll get to in a later volume…). I thought about giving it a go for many years, and about 10 years B.A. (“Before Alexis”), I finally came up with a plan. And I have John McCain to thank for it!

The year was 2008. I had broached the idea of borrowing some clothes from my wife and going as a woman for the annual party we attend a few years prior, and she thought that was a dumb idea. I get it, just going as basically yourself in woman’s clothes is not really a great costume. You’ve got to go as something! So what was so special about 2008? Election year! And I had been struggling to come up with a good costume. My mother had suggested the wife and I go as McCain and Sarah Palin. My wife wasn’t really a fan of that idea, but when I had mentioned to a co-worker that she didn’t want to go as Ms. Palin, he said, “You should!” He was totally joking, but the seed had been planted.

It was the night before the party, and I still didn’t have a costume. As we were discussing it before bed, I mentioned what my friend had said. My wife laughed because she thought, there’s no way that I would actually go through with it, but I knew that I couldn’t let this opportunity pass – this was the best shot I was going to get. So I went to her closet and found a black skirt suit (the most “political” looking thing she owned, and which I conveniently already knew would fit…) and asked her if I could borrow it. She didn’t think it would fit, but I tried it on anyway, just to prove that it did. Without any boobs to speak of, the jacket didn’t look right, so I asked her if I could borrow a bra. She got up and went to get one for me, obviously wanting to decide which one she wouldn’t mind me wearing. It was a dark blue, padded bra, which was perfect. As I feigned struggling to put it on, she finally got the giggles – “If you’re going to do this, I might as well get some entertainment out of it!” So far, so good. I’d rather she laugh than be grossed out. The jacket was a bit low cut, and her next comment was, “What about the chest hair?” I knew that there’s was no way I was going to ruin the image with hair where there shouldn’t be, so I told her it was coming off. Could I have worn a shirt underneath? Yeah, but she didn’t object, and what fun is that?

Unfortunately, my legs are pretty hairy too, and that just didn’t look right either. Luckily, she also had pair of nearly opaque nude tights. Even she had to admit, that looked much better than hairy legs sticking out of a skirt. But I still needed something to wear on my feet. I dug her black high-heeled boots out of the closet to see if they would fit. And this was an exchange that I will not forget for as long as I live, both for the question she asked, and my non-answer: Walking around our bedroom, dressed in a skirt and heels, she asked, “Doesn’t that feel really feminine?” It was an honest question, and I basically just answered it with a shrug and a grunt, like “big deal.” A fully truthful answer would’ve been, “Yes, and it’s awesome!” This would be the first of many missed opportunities to reveal my true feelings about crossdressing.

The next day would be a busy one, because I still needed to get a wig. I hit the local costume shop (a real one, that’s open year round, not one of those cheesy pop-up shops that only open in the fall), with the mission of finding a wig that could be styled in Palin’s trademark bouffant, but could later be styled to look more normal. Ulterior motive alert! Now I could have a wig and not worry about it being “discovered.” (I’m so clever…). I found a nice long, reddish-brown wig with bangs that I thought would work and wasn’t terribly pricey. I also picked up a pair of clip-on earrings. They were kind of ugly, but it was all they had. Also, on the shopping list: little rectangular glasses, Nair, and a toy rifle (pew! pew!). To fully sell it, I also played on recent reports that Palin had been spending crazy amounts of campaign money on clothes by attaching fake price tags to all my clothes.

After a quick dinner, because I could barely eat, I went to get ready. Being amazingly good natured, the wife says, “Let the transformation begin!” It was my first experience with Nair and wow does it stink! But it did the job. The hard part over, I got dressed up and then asked to borrow some make up. She was reluctant, for hygienic reasons, to let me use her eyeliner, but was ok with mascara. So I did the best I could to lay it on thick enough to look girly. The lipstick she let me use was Cover Girl “Rum Raisin,” and I wish it was still available – what a great color. Getting the wig right proved to be much more difficult than I had anticipated, but once again: wife to the rescue. She got the required height by balling up some brown tights and pinning it under the top of the wig. Perfection! One more problem, how was I going to carry my wallet and phone? She asked if I wanted to borrow a purse. So she gave me a small evening bag, which I also used to bring lipstick and mascara in case a touch up was needed, and one of her necklaces to help hide a nick on my chest from the hair removal process. Even as I’m typing this, I can’t believe I ever doubted that she would be mortified by my affinity for dressing like a woman…

Now it was time to leave to the party. As we pulled into the parking garage, I was suddenly plagued with doubt – what the hell was I thinking? Oh well, too late now. We met some friends while walking over who were suitably impressed, and my wife got a chuckle out of the fact that I couldn’t keep up with them while crossing the street in heels! We chatted with a few people once we got there, and one of my wife’s friends came over to talk, pretty much ignoring me. Then she did a double-take and her jaw dropped! She honestly thought I was just some random woman! I was on cloud 9, and that wasn’t all. Waiting to get a drink, some other guy comes up behind my friend and he said, “excuse me” to get past us. A good 30 seconds later, he looked at me again and was like “whoa!” as it dawned on him that I was not actually a woman. I felt elated. All night I got compliments on how much I looked like a woman. The only thing that marred my evening was a comment from the wife, “I am so un-attracted to you right now.” Though it hurt, what did I expect? She’s not a lesbian. Me being me, I took it as disapproval, despite all she had done to help me with this costume.

All too soon, the evening came to an end. For weeks afterward, I was getting comments from friends from the party about what a good woman I made. I had finally made a dream come true, and it was the real start to the path I’m on today. And it’s all thanks to McCain’s choice as a running mate! At least something good came of that…

Oh, and this wasn’t going to be the last Halloween in girl-mode! (To be continued.)

How many of you have gone out en femme for Halloween? What was it like? Would you do it again? I want to hear all about it!

 

 

 

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40-something, married crossdresser - just looking to share stories and make like-minded friends. I have been (mostly) closeted, except for a few Halloween adventures, my dressing has been private. I enjoy creating the most feminine image possible - that's where the rush comes from. I can't ever remember a time when I didn't want to dress like a woman, but as a kid I never imagined I'd be this deep into at my age! But, I think it keeps me young. Hell, better cute than bored!

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*skippy1965(Cynthia)Trisha KobichenkoTiff AnyAlexis MoonTricia Lynn Recent comment authors
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Diane McG
Duchess
Member

I attended a halloween party this week. Since I always go enfemme, that would not have been much of a costume. I went as catwoman. Not so convincing when the costume does not hide my man-belly, but it was fun anyway.

Pippi Long
Duchess
Member

I look forward to it every year! Love getting dressed up. This year I’m trying the gogo girl look .already have the boots and dress ! Can’t wait picture will be posted Much love ! Pippi

Tricia Lynn
Duchess
Member

Alexis, What a great story! My first time out en femme was Halloween sixteen years ago. I was recently divorced after 22 years of marriage and I had been getting seriously deep into allowing my feminine side to flourish as never before. I just decided that I was going to take the opportunity to get out in public as my femme self when I could get away with it. I still didn’t own much in the way of clothing, so I borrowed a top and a “skort” from my older daughter. I already did have all the undergarments and stockings… Read more »

Tiff Any
Lady
Active Member

Beautifully written Alexis, I felt as if I was there , excited to have pt2 ☺. Lovely outfit & smile xx Tiff

Trisha Kobichenko
Lady
Member

my first time out as a woman came when my wife and I moved to Alaska two weeks before halloween. We hadn’t had time to even think about costumes, and when we were invited to a party we decieded to go as each other, her as me, and me as her. Since were relatively the same size fit was not a problem…evening ended with folks at the party chanting for me to do a strip tease…that was some evening

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