Allison M.

A crossdresser's thoughts on life, fashion, fabulousness, and, um… oh, that's right, dressing up!

A Girl In Trouble (or My True Story of Getting Caught)


There’s a story I’ve told online before and have been wanting and meaning to retell here on WordPress.  Now is the perfect time to retell that story thanks to a writing prompt posted Tuesday on Daily Post, in which they ask about a song or songs that can evoke a memory — an even transports your mind back to the time and place of that memory — the instant you hear it.  There are a more than a few songs that qualify in my life, but for my crossdressing side, there’s one song that stands out.  And, since this is WordPress, I finally have the chance to add that song — an audio accent, if you will — to a key part of my life story as Allison.  So without further adieu, Romeo Void, the stage is yours:

“A Girl in Trouble” hit the Top 40 around the fall of 1984, and it serves as the starting point of the true story of how the person that would become Allison got caught.  Yes, my crossdressing secret was uncovered, and it is indeed true.  Here’s how it went:

In the fall of 1984, I was 15 and in my sophomore year of high school.  One day that fall (Election Day, to be exact, not that that part of the story matters), I was riding home on the bus from school, about a mile or so away from my stop, when “A Girl in Trouble” started playing on the radio.  I was getting off the bus alone that afternoon, and I would be at home alone as well; my sister, who usually would have been getting off the bus with me, was staying at school for drill team practice, and our mother and little sister were still on their way back from out-of-town along with our older stepbrother — yes, Evil Ugly Stepbrother — who was going to be moving in with us that day (let’s just say he had a falling out with his mom and still needed a roof over his head and a high school diploma under his arm).

But when I got off the bus, I wasn’t thinking about my mom, sisters, or Evil Ugly Stepbrother.  Rather, I was thinking about dressing up: Having the house to myself for a while, and not having too much homework, would be the perfect reasons to try on some of my sister’s clothing, or so I presumed.  So, naturally, I made a mad dash in that quarter-mile distance between the school bus stop and our house.  The first thing I did when I walked through the door was head for my sister’s room, where I plucked an orange swimsuit and a bra (if I recall correctly) from her dresser and headed into my room.

I was trying on the swimsuit when I noticed that Mom and Evil Ugly Stepbrother had pulled into the drive and were getting out of the car. (Uh oh.)  At this point, I figured if I put my regular clothes back on, sneaked back into my sister’s room, and put back her swimsuit and bra, Mom would very well catch me red-handed.  What I did instead was take off the swimsuit and placed it and the bra into one of my dresser drawers (I placed them underneath my male mode shirts and shorts for good measure).

Well, guess what?  With Evil Ugly Stepbrother moving in, he needed space for his clothing.  And guess what Mom decided to do?  She decided to head into my room and clear out one of my dresser drawers.  Guess which drawer she cleared out?  Yes, the very dresser drawer where I just hid the swimsuit and bra.

When Mom noticed that swimsuit and that bra in my drawer, she immediately questioned why they were in there.  I played ignorant (“Honestly, I don’t know.  Was there a mix up?  Static cling?”) as she proceeded to put them back in their proper place in my sister’s room.  But less than a minute later, she put two and two together and called me into my sister’s room.

“You’ve been wearing them, haven’t you?” she asked in a quiet yet stern voice.

“Yes,” I quietly nodded.

“For how long?”

“I only started it recently.”  Well, that was a lie, of course.  I feared if I told her the truth and said I had been doing this since I was 11, she would really, really be mad and give me a severe punishment.

What Mom said next (and the quiet yet very firm emphasis in her voice) actually kind of surprised me (then and still today), in that she never took it past this warning:  “Well,” she told me, “this had better come to a goddam screeching halt!  I better not catch you doing this again!  You are a full grown MAN!  You are not a girl!”

“Yes, ma’am,” I quietly replied.  “I understand.”

With that, I sulked back into my room and started on my little bit of homework for the evening.  Later that evening, Mom did ask me in passing (and out of earshot of anyone else at home) a few other questions about what she discovered, such as if I ever revealed my dressing up to others at school.  I presumed she was concerned about my well being when she asked that particular question, thinking of possible taunts and teasing that could have occurred had I told anyone at school (and I struggled a lot in school back then).

After that night, Mom never again brought up what she discovered in my dresser drawer.  I’m also pretty sure she never brought it up with my stepfather when he returned from one of his long trips as a truck driver; if she had told him, I imagine he would punish me every which way short of disowning me.  But did I stop dressing up?  Well, of course not.  However, I did become much more cautious with trying on my mom’s and sister’s clothing after that incident.  Yes, there were one or two close calls, but I learned my lesson from getting caught that I should really kept things covert.  In fact, from that point on, I kept my bedroom door closed when I was in there, whether I was dressing up or not or whether anyone else was home or not.

Naturally, to this day I have never revealed to any relative (Mom included) that I still dress up as a woman.  And “A Girl in Trouble” serves as a very apropos song in my life — it’s like Allison’s personal anthem, really.  Any time that song starts playing on the radio or online or even in my head, I think back on that day my crossdressing was uncovered, and how I have matured as both a crossdresser and a person since then.  Even though I was caught that day, it didn’t keep me down; my feminine spirit took a bruise, but it was never silenced.  For as Debora Iyall says in the song’s refrain, and I’ll add emphasis here, “A girl in trouble is a temporary thing.”

Author: Allison M.

A part of the trans community (specifically a "cross-dresser") who finds themselves much more expressive and somewhat more confident when presenting in a feminine persona ("she/her/hers" are my pronouns, thank you very much). A sincere 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 this blog to express viewpoints, thoughts, and feelings about my life experiences, fashion sense, and the world at large... and maybe impressing my high school creative writing teacher (he was a prick, but I really deserved those middling grades back then).

12 thoughts on “A Girl In Trouble (or My True Story of Getting Caught)

  1. Damn, that must have been so hard for you to have faced your mother like that. Although cross-dressing is now more accepted today, one must remember that it wasn’t the case thirty years ago, perhaps even ten. Thank you for sharing a personal memory with us, even if it evokes painful feelings. Keep on writing, Allison!

    Liked by 1 person

    • Yeah, I remember feeling so terrified when Mom confronted me about that bathing suit and bra. Honestly, I really felt that night that she would lay down some form of harsh punishment on me, but to this day I’m still stunned that she never levied anything other than those stern words.

      At times, though, I do wonder how Mom would’ve felt and reacted had I been upfront about how long I had been dressing up (instead of telling her “I only started it recently” like I did), or if I told her that I told others in school about my dressing up (something I never disclosed to them, I must make clear). Perhaps Mom would’ve gone ahead and put me into some sort of (conversion?) therapy.

      As for your “those times vs. these days” comparison, had I been 15 years old now and still living under my mom’s roof, I think she still would’ve reacted the same way she did in 1984. Yes, times have changed and there are those who may be more upfront about their crossdressing today as opposed to back then, with their parents and loved ones maybe being more understanding and accepting. However, some still frown upon it greatly. If you’re thinking my mom was any sort of a religious puritan while I was growing up, she was never like that; however, she was always one to try to raise us the right way, including raising her son to be a man and her daughters to be women. I think she would still have that attitude — and still frown over my crossdressing — were she to raise teenagers here in 2015.

      Liked by 1 person

      • Very true. While times have changed sonce 1984, there are many who still find crossdressing hard to understand. I am sure that your mother meant well, the way she reacted and all. I’m not disparaging her in any way, but it’s possible for a son to be a man and still enjoy crossdressing. It’s different from being, say, transgender. But I’m getting ahead of myself, and so basically I say that you do you, but also remember the memories that have gotten you where you are today. 🙂

        Liked by 1 person

      • Oh, absolutely. I will definitely remember my memories; they are indeed what made me what I am today. 😉 Thanks. 🙂

        Liked by 1 person

  2. Lol, I love how open you are about this. I don’t think I would be able to do so. And I can totally imagine the nervousness of being caught at something. M y problem is that I am bad liar and thus can’t really get out of trouble once I am caught. Lovely story, enjoyed it so much!
    Have a wonderful day!

    Liked by 1 person

    • Yeah, I do wonder if or how my mom was able to pick up the fact that I was indeed wearing my sister’s clothing, instead of just “putting 2 and 2 together” as I put it above. I imagine that perhaps I did show some sort of non-verbal nervousness that Mom picked up on. I don’t mind sharing this story at all, especially if there’s some girl like me out there who went through an experience just like this; perhaps it’ll make them feel better about themselves knowing that they’re not alone as a crossdresser.


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