Every Halloween, post-Sarah Palin, I struggled to come up with a costume. Because deep down inside, I just really wanted to go en femme again. But I felt that crossdressing for Halloween when you celebrate with your “regular” friends was a “one and done” deal. I mean, I didn’t want to let on that I actually liked dressing this way! Heaven forbid! But about five years on, the urge just gets too strong to resist. Though this time, I had the party host to blame. A few weeks before the party, she was asking what I was going as, and as per usual the last few years, I had nothing to offer. For whatever reason, she suggested, “Why don’t you go as a female rock star, like Lady Gaga or Amy Winehouse? You’ve gone in drag before.” Once again, that was all I needed to hear. In my mind, it was easy to justify to my wife if I could just pull the, “I got the idea from someone else” card… Deny, deny, deny…story of a closeted crossdresser’s life, am I right? I told my wife that night what her friend suggested, and she just rolled her eyes and went to bed.

Several more weeks of agonizing followed, going back and forth in my head, and bouncing it around in several forums, looking for encouragement. I proposed that perhaps there was a “statute of limitations,” meaning after a certain number of years off from crossdressing for Halloween, you could get away with it again. It had been five years since I donned the bouffant and tiny glasses, so I felt maybe I could get away with it. Ultimately, what put it over the top was a dinner with some of my wife’s family. Not that there was anything particularly remarkable about this occasion – in fact, it was quite the opposite. Eating pizza in this generic restaurant, in the middle of nowhere ex-burbs, I become overwhelmed by the mediocrity of it all. The middle-class white people stuffing their faces with fried cheese sticks and drinking Diet Coke, making small talk about nothing. I felt as though I was suffocating. And in that moment, I knew that the girl was going to come out this year. Watch out world, I was “Born This Way!”

That night, I told the wife that I had made up my mind, and Lady Gaga it would be. Thankfully, her only reaction was, “You always want to be the woman.” Was she wrong? Heck, no! She’s way more perceptive than I give her credit for. We jumped on the Spirit website so she could help me look for just the right costume. There were several options for cheesy, prefab Gaga costumes, and I figured that’d be just fine for me. I knew I wanted to do the Aladdin Sane lightning bolt makeup, but not sure about the rest of the outfit. I definitely wasn’t ready to go for the blue leotard look (I’m not completely crazy!), but the silver and black minidress seemed promising. So that, a blond wig with bangs, and I would be ready to rock. Once the dress arrived, I tried it on and realized this would require some serious hair removal. But that was fine, because one of my regrets from last time was the fact that I didn’t shave my legs and really show them off.

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I still needed to get just the right shoes. A major difference this Halloween was that I wasn’t simply borrowing my wife’s clothes, and here was a chance to get a pair of heels for myself. She didn’t have anything that would really work anyway. The model on the costume packaging was wearing fishnets and black, heeled booties, and that’s what I wanted. I had dropped in at the Ross store near my work on occasion, and I thought there was a fairly good chance they might have something that would work. Lo and behold, on my first visit I found exactly what I was looking for – they even had them in my size! So of course, I got nervous and fled the store. How was I going to explain buying myself 4-inch heels? I let my paranoia get the best of me. But guess what? The next day I went back and got them. It was just too good to pass up. I snuck them home, tossed them in the closet, and started stressing about when and how to show them to my wife!

Predictably, I didn’t. The big night arrived and I had a lot of work to do. Long story short – Nair is evil. Moving on! I spent hours getting ready while my wife took a nap. Talk about role reversal. After getting dressed, I realized that without something stuffing the top of the dress, it just didn’t look right. Since the dress only went barely over the shoulder, I needed to borrow a strapless bra. When I asked, she just said, “You know where I keep my bras!” I figured it wouldn’t have been polite to just help myself…when I finally broke out the heels, that’s when I got a gigantic eye roll. Remembering how she offered up a purse last time, I expectantly asked how I was going to carry my ID and money, but this time her response was to snap, “What? You want to borrow a purse too?” There was just enough edge in her voice to suggest I might be pushing it, so I let it go.

Well, given the dramatic lengths I went to, the costume was a big hit at the party. I could overhear one my wife’s friends comment to her, “Whoa, check out his legs!” Another highlight was a female friend telling me, “Not many men could pull off a dress like that, but you are totally rocking it!” Looking back at the pictures now, I’m really not thrilled with how it came out. To me, I just look like a drag queen. (Which I guess shouldn’t be a shock, that’s sort of Lady Gaga’s thing). But I wore those heels all night long. For being so high, they were more comfortable than expected. It was the longest I had ever worn heels in my life, and I was loving every minute of it. I recall when we got home and I finally took them off, feeling like my heels were actually lower than my toes! It was really bizarre.

Unfortunately, our story takes a sad turn, through absolutely nobody’s fault but mine. Given the weeks of anxiety, and “should I, or shouldn’t I” over every aspect of this costume, it shouldn’t come as any surprise that a post-party crash was inevitable. When the kids got dropped off at home the next morning, my 9 year old daughter jumped into bed, as she was prone to do, but because my legs were now hairless, I started freaking out, shifting uncomfortably to make sure her feet didn’t come in contact with my legs. She never figured anything out, but the whole episode triggered a major anxiety attack. It was Sunday, and we were having dinner with my family, and I had a hard time eating. Ironically, we ran into some friends from the party a few times that day, and people were still telling me how “amazing” my costume was. But by this time, I couldn’t enjoy the attention. I just felt ashamed and weird and near panic and didn’t know how to make it stop. On top of that, my chest had reacted negatively to the Nair, and I was seriously uncomfortable. I wanted so badly to talk it over with my wife, but I couldn’t bring myself to get the words out. Eventually, I managed to mumble something about feeling like a freak before she fell asleep. Still feeling off the next morning, she gave me a big, comforting hug before I left for work, and that was the end of it.

I got over it, of course. We always do, right? No matter how much mental anguish we inflict on ourselves, the “girl” always triumphs in the end. And this girl was bound for another autumn appearance, and it would come much, much sooner than last time.

Well, that’s my Halloween horror story! I promise the next episode will have a much happier ending.

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How have your Halloween adventures gone?

Did all go better than expected and you got a pile of compliments being a girl?

Or did things not go well at all and you got more folks laughing at you than laughing with you?

Happy Halloween Girls!  Sincerely, Alexis Moon


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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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DeDee Demore
Active Member
1 year ago

Hi Alexis, I loved your detailed story of your Halloween adventure, it was a good read and went over it a second time. I laughed so hard when I read your line “Nair is evil” but I felt bad later to read you had a bad reaction from it the next day. You did look good as Lady Gaga a nice toned down version of some of the outfits I seen her wear. I hope with all the issues and emotions you went though before and after that you did have a good time at the event compliments included and… Read more »

Amy Myers
Noble Member
1 year ago

Sounds like it was a great event, I mean, with getting so many compliments, that is just fabulous!
Too bad about the negative parts, but I always have a bit of a down after the high of dressing. The main thing is that you did it! And it went over!
Thank you for sharing!

Tanis Gibson
1 year ago

Hi Alexis! Loved your article. I went out as Elvira queen of the night, and later as a lady police officer. (Very sexy skimpy costume i got at an adult site) worked all day as witch too. (LOVE halloween!)
Was awesome time!! And i still went door to door witnessing friday morning. (Im jehovah’s witness) so i was bad till morn and then a good girl who walked all day in 5in heels lol.

Lynne James
1 year ago

Hi Alexis. Loved the story. This will be my first halloween and experience to cross in front of family. And friends. Your story will help guide me through my times as a woman. When i told my wife and daughter I was going as a woman for Halloween my daughter was excited about getting the chance to do my makeup. We all laughed about it but little does she ( my daughter) know it’s what I really want. And my wife is becoming more accepting of me wanting to wear woman’s clothes. Thank you so much for your story

Lynne James
1 year ago

My wife knows I love to wear women’s clothes already. Still she has reservations about it and is feeling insecure. I treasure her everyday that I still love her and am wanting to be with her. My daughter doesn’t know that I do it except that I said I would dress for Halloween. I haven’t decided what to go as yet. Still deep inside I would do it everyday but haven’t found the courage to tell family

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