In Her Shoes

In Her ShoesIt’s all too common for a little boy to be dressed up by his mother for Halloween, as a Disney princess, or a cheerleader, or a pretty little witch. (I’m fairly sure that yours truly once wore a black dress for trick-or-treating, although the photo evidence of this has long since vanished.) I suspect that this is how many cross-dressers are born; not created, as such, but this can be what triggers the condition in someone genetically predisposed for it. So what’s a guy to do when he grows up and finds himself obsessed with wearing pretty dresses and long stylish hair and the kind of figure men drool over? This tall tale tells of one young man’s solution to the problem of how to emulate your mother without going too far over the top. Or maybe it is over the top—who can tell anymore? Enjoy!

I don’t habitually write a caption every year for this particular holiday, but I have done a few over the years. Happy Halloween!


Discouraging Word

In Her Shoes caption

15 thoughts on “In Her Shoes

  1. Pingback: Cosmopolitan July 2019 | Amanda's Reading Room

    • Thanks, Jen. This vignette is another one I knew you’d like. (Halloween. Hmmm… on the one hand, if it was a year-round thing it wouldn’t be so special. On the other hand… yowza!!!)

  2. Pingback: The New You | Amanda's Reading Room

  3. Mother was a highly-sought-after model. When she found that Halloween was only one day on which I wanted to be her, she proceeded to make me into a beautiful daughter. We lived together for a long time and shared everything, clothes, heels, makeup and, occasionally, one of her dates. I remember those times with great love and would like to have her with me now as I am living much of the time as her clone and loving every minute of it.

  4. Great story..I take after my mom..a bit too much..friend have called me her clone, but she has a nice pair of 34 b’s and .. well..I have..well you know. I tried on her high school cheerleading out fit once and a buddy saw a pic of my mom in it and said ‘dude..its

    • Thanks. There are worse fates than being your mother’s clone, especially for those of us in our line of obsession. Hope you have fun with it! (Though perhaps not quite as much fun as the hero of this vignette, who did take it a wee bit over the top.) 🙂

  5. wonderful and funny all rolled into one…as I’ve written before on Halloween while in high school my mother always thought it would be fun to go trick and treating dressed as each other. Her in my (American type) football uniform, those clunky old style football shoes and all…me in one of her old dresses, stuffed bra and me, trying to keep my balance without much success, heels. In college I followed the tradition at all school Halloween parties as a girl scout, cheerleader and flapper…all remember the laughs my mom and I had together (so many years ago).

    • All I can say is WOW. I can’t even imagine doing that with my mother. You are certainly lucky to have had that sort of understanding and acceptance in your life. Thanks for writing!

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