Sunday, September 10, 2023

Missed the Boat

I missed the boat!

My high school did not have a womanless beauty pageant or a gender swap day like the schools that the lovely lads in lace above attended. The closest our school came to approved crossdressing is when the boy’s basketball team performed in 1920’s flapper drag for the annual school musical. Their femulation was nothing to write home (or here) about, but I was jealous nonetheless because given the opportunity, I knew my presentation would have been more authentic than the basketball men in dresses. 

Men wearing earrings became a thing while I was in high school. I recall our principal warning the boys that if anyone showed up wearing an earring that boy would also begin wearing the Catholic school girl uniform that the distaff side of the student body wore. 

I thought about borrowing a pair of my mother’s clip-ons and wearing them the next day, but I did not want to give the class bullies the satisfaction that they were correct in electing me “The Boy Most Likely to Change Sex.” So I just dreamed about wearing a navy blue jumper, white blouse, nylons and penny loafers to school instead of my boring sports jacket and trousers. 

Instead of being a closet crossdresser, what if I was more open about my crossdressing back then? I am certain that my parents knew what I was doing when I was home alone and I like to think they would have supported me. And I’m sure that my mother, an excellent seamstress, would have sewn me confections that would have made the other girls jealous. 

Living full-time as a woman would have been delicious, but not only did I miss the boat, but I was too scared to even buy a ticket for the journey. But back then, I did not know about womanless pageants and the like. I knew I wasn’t alone, but I did not think there were many others like me even though my best friend in grammar school practically came out to me as a crossdresser. What were the chances of that if crossdressing was as rare as I thought? Nevertheless I was not prepared to take the journey solo.

Today, looking at the thousands of the Internet images of girls like us, I wonder if there are any guys who haven’t crossdressed! There sure are a lot of us! There probably always were, but today we are more open about it, so it seems like there are more.

If I could to do it all over again... but I can’t, so why beat myself up about it. Instead, I will continue to be the best woman I can be or rather, the best old lady that I can be and enjoy my femininity as often as I can.  

Source: Boston Proper
Wearing Boston Proper

Kristin and Jean
Kristin and Jean, 21st Century son and father


  1. "...but I was too scared to even buy a ticket for the journey..."

    Or perhaps it wasn't safe for you to be you back then.

    I think it's easy to look at a situation and think of our own failings. But would we say that to a friend? 💜

    Perhaps, like a lot of gender nonconforming folk, you did what you could, given the situation you were in.

  2. Yes sometimes I do feel like I missed the boat when I see the the openness and resources available for trans gender persons today, I remember looking for a therapist back in the early 90s very few therapist worked with trans gender persons there were maybe one or two and typically associated with support groups. Getting HRT was very difficult, surgeries even more so. The idea that you could transition on the job was almost unheard of and in most major corporations a ticket for getting fired or laid off at the next round.

    From what I read trans gender students are fairly common in high school with most high schools having one or two the same is true for colleges many trans gender young people choose to begin transition when they start over in college

    I guess you could say we missed the boat but perhaps a better analogy would be we were the first ones on the beach and cleared a path for others

    Paula G

  3. I missed the boat too. My HS did not have Womanless Pageants, nor did I possess the courage to dress up as a girl for Halloween. When I was around eleven, I attended a YMCA kid's Halloween party and a boy who I did not know showed up dressed as a girl. He sat down next to me and I realized that he had on nylon stocking! I saw the garter clipped to the top of a stocking peaking out from the hem of his dress.

    I wondered if he had on a girdle too, just like my mom would wear, and I wondered why he'd come dressed like that? A pang of jealousy rose within me and I'd wished I'd come as a girl too, but I knew that I wasn't brave enough.

    Within a year, I regularly dressed up in secret and put on my mom's nylons, girdles, and slips. I loved it, but I always knew that I couldn't do it in public.

    In High School I became involved in drama and one year our school' entry into the State Play competition was a short Greek tragedy. I went out for a specific part and didn't get that part nor any part. I served as a member of the crew and when I saw that the costume I would have had to have worn for that role was a dress onto which things were affixed to make it appear Greek, I shuddered with relief that I hadn't gotten the role. Yet I still yearned to be a girl for Halloween or to declare to family and friends that I wanted to dress up like a girl sometimes.

    Today I'm a closeted old lady. What I don't know is whether I would have been happier had I not "missed the boat?" I've enjoyed being a man all my life. I've enjoyed the times I've crossdressed and I'm not certain if I could have juggled the two more openly.

  4. Wow, Jean and Kristen! I remember them from an old issue of LadyLike, and it's great to know they are still around and about.
    Do they have any online presence?

  5. I don't keep my wearing dresses, along.with fingernail lacquer (polish) a secret. I have not worn trousers since the middle of June. And on Sunday morning I wear heels, stockings, and makeup to church. I figure if women can wear jeans and gym shoes to church I as a man should be able to doll myself up in a dress along with other items. And yes, I am a member of a local Episcopal church in good standing and I sing bass in the choir.
    I have received virtually no pushback for my attire. So, men, if dresses float your boat, by all means WEAR them.


  6. Sandra Bridges ( 10, 2023

    Kristin and Jean, yes!
    I'd like to know more about them and their story.

  7. glass half empty or half full.@ least at this age (you and me) can take full advantage
    of being out and about as a woman. when I was a teenager a young person was arrested in a movie theater in my city for attending dressed as a girl. so better now than never-emily

  8. I wonder if "womanless" beauty pageants have been banned in Florida yet? Would that come under the heading of "gender reassignment?"

  9. I have never seen one or seen one advertised, only online reports from other states. But if my ship came in I'd be at the airport

  10. We’re gonna need a bigger boat!

    Better to catch the late sailing than not at all. Most of us over a certain age (I presume) would wish we had started to explore this aspect much sooner than we did—I went out publicly the first time at 42. But I also think that society is much more tolerant now; would it have been such smooth sailing if I did start earlier? I’m just happy that I DID take that initial plunge!

  11. In my country (Hungary) there were never such things, like Womanless Beauty Pageant. We had such, as "carnival", during spring, in the schools, but the boys usually dressed as more accepted characters, like policeman, pirate, etc... It was extremely rare, that someone took the courage and dressed as a woman. And we had no Halloween neither, when boys could dress as women "legally". I have never seen such in our school. I saw only a boy once, who took her mothers dress, heels and dressed as a woman, but that was not during this carnival. But of course I was envious. So I also missed the boat. And now Hungary is even worse, so such things won't happen there in the near future.