I Came To This Strange World Hoping

It was Halloween, but it definitely wasn't a costume.

Sure, we went to two different costume parties, and sure, to make dealing with it easier, my wife dressed as a guy. But it definitely wasn't a costume.

We go to two Halloween parties every year. One is thrown by our youngest son's babysitter, and is usually pretty tame. The other is hosted by a close friend and is usually very sexually charged, both in costumes and behaviors. They usually don't happen on the same night but since Halloween was actually a Saturday, they both wanted it that night.

I couldn't think of a costume this year to save my life. I would have been fine doing something Stat Wars related, naturally, but didn't have the time to go shopping. Then, a couple weeks ago, my wife texted me one sentence that I never thought I'd hear from her: "Well, here's your chance to dress as a woman."

I had to explain to her that even though it was for Halloween, and even though it would seem like some kind of joke costume to a lot of people, I was going to take it very seriously. No fake exaggerated tits, for starters. Just my little tiny A cup boobs. Also, I wanted a dress that wouldn't look like a joke, wouldn't be ill fitting, wouldn't be worn once and thrown away. That was probably the hardest part for her to accept, that I wanted to keep the dress so I could wear it again. A few days before Halloween, before I'd even bought a dress, she was still making comments suggesting she was hoping I'd throw the dress away after that night.

I went to a thrift store, and Shannon had to help me calm down, talk me into focusing on the positive, help ease my anxiety so I could actually look at the dresses without running from the store in shame. Not an easy task to accomplish from several states away. I was able to buy a dress. My first dress.

Unfortunately, it didn't fit. Major setback. That meant I would have to go through all the anxiety again, trying to find another dress that actually fit.

That night after dinner my wife actually accompanied me to another thrift store to look at dresses. She was very helpful and suggested different styles that might work with my body. It was very unexpected, but very welcome. We found a long black gown, and I did something else I never expected I'd ever do. I took it into the fitting room, so there wouldn't be a repeat of buying a dress that didn't fit. The fitting room attendant gave me an odd little smile when she checked what I was taking in, but she didn't say anything. I guess being two days before Halloween, she'd seen plenty of guys trying dresses on for costumes.

This dress fit much better. The only issues were that it had a seam right under the boob area that was really tight and uncomfortable, and that it was just an extremely plain, dull dress. I didn't buy it, but kept it in mind as a last resort if I didn't find anything else.

The next night we went to the store to buy the kids new winter coats, and I decided fuck it, I'm going to look at new dresses. I still don't know what urged me to do it. I found a dress, and again took it to the fitting room. This time, though, I wasn't feeling quite as brave and hid the dress between several pairs of jeans. (This ended up being unnecessary, as there wasn't a fitting room attendant at this store.)

The dress could not have fit more perfectly.

I had my first dress (version 2.0) and I couldn't wipe the smile off my face. The feeling was one of pride, of joy.

I was so ecstatic that I sent Shannon and Tracy a picture of me in the dress while still in the fitting room. I had intended on waiting until I was fully dressed for the party, but I couldn't wait. It was impossible.

Saturday afternoon I still had to figure out what to wear on my legs, and what accessories I'd wear. I have a pair of maroon over the knee socks that would look very good with my dress, but I also thought some tights with bats, spider webs, or other Halloween theme might look good as well. I couldn't find any Halloween tights, and the knee socks just kept rolling down being annoying, so I settled for some black tights. Nothing flashy, just straight black.

There was one more thing I wanted to talk to my wife about before I started getting ready. My legs. Ever since she suggested I dress as a woman for Halloween, I had a desire to go as far as she would let me. But I had one major goal of shaving my legs. When I asked her if she would be OK with it, her initial reaction wasn't great. But she told me to do it if that was what I wanted.

I never realized just how much hair was on my legs. I'm certainly not as hairy as most males, and it's actually something I've always been a bit self conscious about. (Stupid thing to be self conscious about, I know.) I used electric clippers to take most of the hair off, but it still took three razors to get my legs smooth.

I haven't been able to stop rubbing my legs. It feels so amazing! I know I can't keep them shaved permanently, but I'm definitely going to do it for a week or two, pretend it's just taking a long time for it to grow back, or something.

My only other accessories were one of my wife's necklaces, and some pink lipstick. I would have preferred burgundy or a dark red, which I feel would have gone much better with my dress, but that's the only color my wife had. So pink it was.

Even when I was getting dressed, I wasn't sure if I would be able to leave the house in my dress. I'd never done it before. The anxiety level was off the chart.

But I did it.

When we got to the party at the babysitter's house, the women in the living room actually all complimented my dress. They still laughed, thinking my outfit was a joke costume, but they complimented the dress nonetheless. Then the sitter's husband came in from the kitchen... I know my gut is kind of large. It's because I drink way too much soda. I can eat healthy, do yoga, go for walks, all that jazz, but can't get rid of the belly because I can't lay off pop.

He thought I had something under my dress and that I was pretending to be pregnant. It was embarrassing as fuck.

I sat very quietly for the hour or so we stayed at that party. I think I said three or four sentences the whole time.

The other party was a different story altogether. There are five of us at this party every year - the host and her boyfriend, my wife and I, and one other guy. The other dozen or so people each year are a rotating cast that are never repeat attendees. Usually I sit in a corner and barely talk to anyone but the other four "regulars." This year, I was super confident. I was happy. I didn't sit in the corner for a second.

It was amazing.

It's been a couple days, and I'm still smiling. My wife is fine with me keeping the dress, but still doesn't want to see me in it again, so I'll still only be able to wear it when I'm alone, but I get to keep it. Small steps.

Before I wrap up, I want to do one more thing I didn't know if I would ever be comfortable doing. Here's to pushing boundaries.

It was Halloween, but it definitely wasn't a costume.

Title today is from "New Soul" by Yael Naim. It's not an overly appropriate song lyrically, it's just a song that always makes me happy when I hear it, due to the music and tone.