Halloween Roundup

HalloweenDespite the importance of this holiday to the TG community, I haven’t used Halloween all that often in my own writing. So just for fun—and to encourage me to maybe do better next year—I’m posting a quick roundup of my Halloween captions and vignettes.

Most recently, duh, was yesterday’s caption “Flashback“, but you already knew that.

Miles to GoTwo years back I did post a caption on October 31st, so even though “Miles to Go” doesn’t actually mention Halloween (like, at all), I’ll toss it in here for the sake of completeness. (I can do that ’cause it’s my website, so all you haters can zip it.)

Lovely Miss WeasleyIn my own defense, I did post a Halloween-themed cap earlier that month. “The Lovely Miss Weasley” is that thing where a guy goes to a party as a girl and then realizes he wants to be a girl for real. Haven’t we all, right?

Halloween HousewifeBefore that, you have to go all the way back to 2011’s “Halloween Housewife“, which is the standard trope where a guy dresses up as a girl for a party and no one twigs that he’s not actually a girl. I’ve so been there.

In 2010 we find “Maid for Halloween“, a three-page vignette with rather unrefined graphics. Here, a mother transforms her college-age son into a woman for the nefarious purpose of setting him up on a date with a male co-worker. Exactly why she does this is never explained, but things do get rather hot-n-heavy at the end so why bother looking deeper than that?

Finally, way back in 2007, we have “Halloween“, a four-page vignette with very basic graphics (although the woman’s pic is one of my all-time favs). Now we’re deep into the Halloween cross-dressing trope. Here, a mother transforms her teenage son into a copy of herself, while at the same time disguising herself as the son. Again, her motivation is a bit thin on the ground, but it seems to involve him being kissed as a woman and some of the usual “now you know what it’s like to be me”. I think this tale captures something very basic about the Halloween TG experience; not so much in the reality of what costume we might wear on the night, but in what it means. In essence, it’s the mother re-living her own childhood by turning her son into her younger self. And if that seems just a little too deep for a holiday that’s all about the kids, join the club. I am so outta here.

Happy Halloween!


9 thoughts on “Halloween Roundup

  1. Wonderful stories, they reminded me of the Halloween my sister & mother turned me into a girl. They went all out, polished finger nails & toe nails, completely hair less body, my shoulder length hair curled & styled into a feminine look, ultra thinned & highly arched eyebrows & double pierced ears. After they finished dressing me in my sisters red velvet mini dress & red platform heels, they told me that they knew all about my dressing up as a girl & sneaking out of the house at night to walk around town, that’s why we are taking you to the mall & getting you your own female wardrobe. They knew that me & my friends hung out at the mall arcade every night so they parked the car to where we would use the entrance by the arcade & I would have to walk by all of my friends hanging out in front of the arcade. My sister told me not to worry, that no one would recognize me, if anyone came over & talked to her, she would introduce me as Joanne, her cousin from out of town.

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  6. As a junior in high school many, many years ago my mother came up with the same idea. Now we didn’t go way over the top with my outfit, an old dress, stockings, a stuffed bra and heels that I almost broke my neck on and mom wore my high school football uniform and we went around the neighborhood treating for beer (for my dad) we had a ball, lots of laughs with my mom’s friends…of course she wanted to do it the next year…my mother would do anything for a laugh…miss her…this story reminded me of our times together..thanks

    • You’re welcome. It’s gratifying when a story touches someone like that. And it’s great that you have such a nice memory; like I said elsewhere, mine is thoroughly spotty (it isn’t just middle age setting in either; that memory was always unclear).

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