A Halloween Walk on the Wild Side

Halloween, a/k/a the National Crossdresser’s Holiday, has long been a day of interest for me.

When I was in grade school, I was always jealous of the boys who came to school dressed as girls (all these years later, I’m still jealous). In eighth grade, I did go trick-or-treating dressed as my sister. I’ve been out dressed on Halloween every year recently when I’ve been in town. 

This Halloween, I had two outings, both with my GG friend Michelle. In the afternoon, we had a long postponed shopping outing with her 11 year old daughter Mila to the St. Louis Galleria. Mila had told Michelle previously she wanted to shopping with me, because I have good taste.

We started with shopping at H&M for Mila, finding a cute pair of overall shorts and a couple of tops for her. Then we ate lunch at the Cheesecake Factory. It was just after my five year anniversary of going out, so I wore my favorite red dress, the first one I ever bought after trying things out while dressed.

Following lunch and looking at a couple of more stores, Michelle dropped off Mila at her dad’s. 

It was adult time.

Michelle and I met at her salon. She walked in with a bag full of surprises; dresses, costumes, heels, and wigs.  We played dress-up to figure out what to wear for Halloween, trying on various combos.  

First up was a black and floral pinup style dress Michelle had worn for a social media photoshoot for her salon. It was too small for me, but it fit well enough for pictures. 

Second was a fake leather dress with a lace-up bodice. To my surprise it did fit, and more pictures. Michelle ended up wearing this one.

Third was a cat woman costume with a criss-cross bra top and fake leather pants, complete with a mask and a whip. I didn’t have the right equipment up top for the costume, and wearing the mask without my glasses would have been an issue, but it was fun to try on (and if I was about 15 pounds lighter it would have been a lot more fun).

Next up was a corset top. I tried it on, but we couldn’t get it zipped, even after taking off my padded bra. Not giving up, I connected the zipper, stepped into and then somehow squeezed into it, and Michelle managed to zip it up. I then stuffed the padded bra into place without fastening it in the back.


Michelle handed me a pair of footless of mesh tights to wear over my patterned tights. Given I wasn’t wearing anything under the patterned tights, the only thing covering my nether regions were three layers of mesh, including the bottom of the corset top. It was Halloween–and I wasn’t showing anything that wasn’t supposed to be showing.

Now for wigs. Michelle had a black and white wig from another costume I tried on first, then a blonde wig. Neither of them was exactly right, so I tried on the redhead. Although it was big hair, the color worked (Michelle wants to take me wig shopping for a new wig, and of course I’ll all in). Michelle donned the fake leather dress with the black and white wig. 

My final touches were the fingerless gloves from the cat costume, a black cape from another costume (which I needed for the chilly night) and a pair of Michelle’s heels, ones I had given her (I ordered pairs for both of us, one in her size, one in mine–hers arrived, mine never did). In turn, she wore a pair of my booties (and later in the evening, when my feet had suffered enough, we swapped back).

Michelle often posts pictures on social media to promote her salon. As she had just installed a new sign (her salon is new), we went outside and shot  pictures with the sign. Telling myself, WTF, it’s Halloween, I told Michelle she could post the picture of her with the sign on her Facebook page–along with the best picture of us. She asked me whether I was sure I wanted to do it, but as we have almost zero common friends, I told her to post it before I changed my mind. At this point, it has 81 likes.

We ventured to a couple of LGBT bars in St. Louis, talked with a few patrons, got a couple of compliments, had a couple of drinks, and called it a night. We took some pictures, of course. Our outfits were mild compared to some of the other patrons. Michelle was fascinated by the makeup of a couple of the drag queens, and I took a picture of her with one of the queens (which she also posted to Facebook).  My outfit was just a wee bit outside my comfort zone, but I managed (and I really, really, really liked the look).
If we return some day to the same bars (Michelle likes going to drag shows, while I have never been), the corset top might make a reappearance, perhaps matched with a black leather skirt I have.

A couple of postscripts.
First, I told my wife beforehand I was going out on Halloween, AND going out with Michelle and her daughter, and she was fine with it. After getting home, she just asked if I had a nice day, I said yes, and that was it. A big positive step forward.

Second, I texted Michelle afterwards and thanked her that with everything she has going on (a lot, including the completion and opening of her salon), she took the time to organize a bunch of clothes, wigs, and shoes to try on because she knew it would make me happy (and she had a great time too).

Already looking forward to Halloween next year–and my next time out with Michelle. 

6 thoughts on “A Halloween Walk on the Wild Side”

    1. Thanks as always, Renee!

      A second Halloween? Excellent idea (although October is more heat friendly than June).

      Always trying to find venues where I can dress bolder, but it’s a lot easier when I’m out with Michelle. She makes a good wing-woman.

    1. Thanks Mark!

      It fit because Michelle and I are similar sizes (she is slightly smaller than me), as I have fit into a number of her clothes and she has passed along a number of her clothes to me (“Hand-Dee-Downs”), and because I really, really, really wanted to try it on. I inhaled and Michelle zipped, and it fit (and I could even breathe). I wanted some shape up top, so I just stuffed the cups where they should be, and figured the tightness of the top, combined with gravity, would take care of the problem.

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