Allison M.

A crossdresser's thoughts on life, fashion, fabulousness, and (oh yeah) dressing up

Allison’s crush letter (for “June Jour”)


Okay, time for me to catch up on The Finicky Cinic’s “June Jour Challenge.”  I had devoted literally all of my morning and half of my afternoon on Saturday to my previous, lengthy post, and I spent Saturday evening a theater performance downtown.  So, I didn’t get to formulate a response to this prompt from F.C.:

Write a letter to your crush, real or imaginary.

First off, I am so impressed by how F.C. can write to her crush; she really writes so longingly and movingly, and with such detail, to the person she has a fondness toward.  She communicates how beautiful she thinks her crush is, going right out at times to just say “I just want you.”  If someone had a crush on me, I’d want to receive letters like that rather than having someone write me nothing more than the likes of, “You got a body that just won’t quit.” (Really, people?!  Who are you going to impress with that line?)

But I digress… there’s no one I’m having a crush on at the moment (male, female, or otherwise).  I did, however, have a… well, let’s just say I was fascinated with a classmate of mine in high school.  Being very shy and all, I never really expressed that fondness to her.  But I’ve never forgotten her and that fondness I felt for her.  She lives somewhere in Colorado right now, and if I had the gumption to write a letter expressing my infatuation for and admiration of her, it’d probably go something like this:

Dear H:

Hey there!  How have you been doing?  My, it’s been a long time since we’ve seen each other.  Yeah, I know that we have seen each other a couple of times since high school, but I still think of you as that awesome fashion plate, the best-dressed girl in our class, perhaps even the best-dressed in our entire school district. [Side note to the reader: That’s an easy argument to make since we went to school in a very small town.]  You looked the epitome of “totally ’80s girl”: Big hair, all moussed up and with some curls; stylish shirts; jeans on your legs, or even parachute pants.

Yeah, you certainly caught the eye of every guy in the class.  You even caught my eye, too.  From afar, though.  I was that shy, nerdy kid in the glasses who kept my distance from everyone.  And while you were welcoming the kinship of your friends and the gazes of the other guys, I was admiring how stylish you looked and how friendly and personable you were.  You were a real live person, not some model in my sister’s Seventeen magazines or a video vamp on MTV.

Back at that time, I was just as shy and awkward in women’s clothing in the privacy of my bedroom as I was interacting with others at school. (The bullying and teasing from the upper-class jocks and toughs sure didn’t help my self-confidence, that was for sure.)  At least you appeared to be someone that, though you weren’t really in a position to stand up for me (let alone notice I needed to be stood up for), would still want to stand up for someone as small and afraid as me.

When we did interact in school, you were just as warm and friendly as I had imagined… though you weren’t one to reciprocate the fondness I had for you.  That’s all right, though; I never outwardly showed that fondness, and if I did, I was one to never expect that it be reciprocated.  You were, however, more noticing of me in the times we met during our class reunions.  It may have been a result of how we individually matured (we all mature at some point, don’t we?), but you were more conversational to others — and even more conversational to me — than I recall you being back in school.  Your style changed, too: Gone were the big hair and flashy clothes of the 80s in favor of more conservative dress and hair style (short brown bob with blonde highlights; very nice).

Even at those reunions, I never did admit to you that I had a crush for and an admiration towards you.  Something told me, though, that you would be appreciative of my crush if I had admitted it to you… even though your non-verbal expressions didn’t show it the last time we met, at our 10-year reunion.

I do feel sad that we haven’t seen each other face-to-face since then, including the class reunions you’ve been unable to attend.  I know you live far away from Wisconsin now, with at least one child of your own, and perhaps a full-fledged family now.  But I do want to say that I have long admired you for the personality you display, the style you exhibited then (and now), and the well adjusted person I’m sure you are today.  And I want to thank you for the kindness you showed me, however limited it may have been.

Perhaps someday in the future, you and I will get together again and talk about our lives now, our high school days, perhaps even our feminine fashion sense. (About that last part, perhaps you can give me some tips on that, if you can keep a secret about my crossdressing; I hope you are as open-minded as I imagined you’d be.)  Until that day comes — or if, Heaven forbid, that day never comes — I hope you and yours are in the very best of spirits; that you all are receiving the happiness you truly deserve; and that all of your dreams have or will come true.

With sincere admiration,



Author: Allison M.

A part of the trans community ("cross-dresser" is the term that applies to me) who finds themselves much more expressive and somewhat more confident when presenting in a feminine persona. An admirer and supporter of those who are fashionable, fabulous, and friendly (LGBT or otherwise). Someone who tries to be witty and unique, but is not even remotely perverted or a pariah (I am a real human being, just like you). Using various writing styles on this blog to communicate thoughts and feelings concerning my life experiences, fashion sense, and the world at large (and maybe impressing my high school creative writing teacher who deservedly gave me middling grades).

3 thoughts on “Allison’s crush letter (for “June Jour”)

  1. Pingback: Someone I look up to (for “June Jour”) | Allison M.

  2. Aw, such a sweet post. Is it all right to say that I found it adorable? 😉

    I’m flattered that you enjoy reading my “A Letter To My Crush” posts. I admit that I’m a romantic at heart, and I just write them when I’m feeling inspired. 🙂

    In any case, thanks for sharing your letter to your high school crush!

    Liked by 1 person

  3. Pingback: “June Jour” postmortem | Allison M.

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