Halloween Memories

[Toni_Lynn]

For crossdressers, there can be no doubt that Halloween is a special time for us. For me, it is a time when I think back, with a certain bit of wistfulness to my schooldays. Hence, this thread for Halloween memories. Oh how I remember wishing and hoping back when I was 9 or 10, that my Halloween wish would come true. Yes, it was to go out as a girl.

Back in those innocent days of the late 60s, trick-or-treating went on all week, not just for a few hours on a specific day. And my town had a Halloween parade. I usually went out as a spaceman or a cowboy or some such rubbish. But on those days when I didn't go out, and I was home with my family greeting the others kids who came to our door, I recall many of the neighbourhood boys being out in their sister's dresses. And I saw lots of my peers in dresses in the parade. Damn, how I envied them! How I prayed that I would be allowed to go out halloweening as a girl. And then maybe my mum would see how happy I was and let me wear dresses all the time!

Then, when I was 13, I was in the Boy Scouts. Its Halloween 1970, and in 3 months and 5 days or so (5 February 1971 at about 1PM) I would buy my first training bra, my Teencharm. It was the halloween party, and I guess I went as something dumb like a cowboy. Yuck-phoo-ee. BUT -- there one of my fellow boy scouts was there dressed as a girl scout, and he made a point to show us that he was wearing a training bra. He as a proud as any girl! It was so cool. I don't remember what style/ brand it was, but I do remember that it was a proper training bra, unpadded and and unstuffed with tissue etc. Fit him perfectly if I recall. I wonder to this day if his mum bought it especially for him.

I was captivated -- In fact I was as green as his girl scout uniform with envy -- and knew at that point that I wanted one. I NEEDED to have a training bra. And so it was 3 months and 5 days later that the idea popped in my mind again on that shopping trip to G C Murphys. The rest is blissful history

Huggles

Toni-Lynn

[MarinaTwelve200]

Yes, back in the early 1960's Dressing as "A Girl" was THE Holloween costume for us adolescent boys back then. Most of my friends and fellow schoolmates dressed to the nines in their skirts, lipstick and high heels, and embarked on hours or trick or treeting. Except for ME. Sure, I went trick or treeting too, with the guys, but I usually went as something "scary" like "death"--with a skull mask, cloak--and even a Sickle.

I was too "embarrased' or "scared" to dress as a girl myself--but I had been doing it secret since age 12. Perhaps going OUT like that struck "too close to home"?

Of course, Looking back, I want to KICK myself. I could have gotten away with it very easily. I had a great excuse (ALL the other guys were doing it) and no one, my parents included, would have thought anything about it.---Indeed, I would dare say that my Mom likely would have helped me out entheusiastically (she was always making funny jokes to me and laughing about related things anyway) Just one of those missed oppourtunities we all have and regret,--- Sigh!

BTW--The prevalence of CDing on halloween back then is one of the things that make me beleive that CDing, or at least the desire to, is a whole LOT more common than we might dare to think, especially in guys from my generation.

[TGMarla]

Way back when I was in Boy Scouts, one guy did come dressed in a pretty green plaid skirt with a nice sweater top....I remember that it didn't go over real well for him. To me, a transgendered teen who regularly raided his mother's and sister's closets, it was obvious he was transgendered, and had taken the opportunity to wear girls' clothes. I envied him. I loved what he was wearing. I wanted to wear it, too, but I had no such guts, gumption, or stupidity.

I dressed on one halloween long ago. My wife wore one of my suits and a moustache. She thought it was remarkable that I had done such a good job on my makeup. At that time, she did not know that I was a regular crossdresser. I shaved my legs, wore pantyhose, carried a purse, wore a very nice dress, brought a pretty sweater along in case I got cold. I had the time of my life. But now she knows that I have crossdressed for most of my life, and it's not something that she's all that comfortable with.

At present, given the situation, I doubt that crossdressing--being Marla--for Halloween is much of an option for me.

[danam]

Yes, for some reason I was scared to death of dressing like a girl for Halloween, even though I desperately wanted to. I never did.

Maybe it did hit too close to home? Maybe I never felt like I could never pull it off--it seemed that only the real outgoing, lampshade-on-the-head kind of guys could pull it off. I was always too quiet--I guess I would totally give myself away because I would enjoy it TOO MUCH!!!

[Darlene Dippy]

You US girls and Halloween Stories hack me off.

Here in UK no dressing girlie just kids dressed as witches playing Trick or Treat - forget it its too difficult to explain!

Oh well not to be a killjoy, enjoy yourselves!

Yours enviously

Darlene

[MarinaTwelve200]

Living in the south, we also had MARDI GRAS ! (It ain't just in New Orleans, folks)---yet another time to dress up and walk in the parade. Back in the 60's it was just a sport to try and tell which of the women were actually guys.---we would sometimes make bets, and then hang around for a few minutes, till one of them SPOKE and gave his true gender away. :D

But something happened in the 70's and from then on, the guy who would CD on Halloween or Mardi Gras, suddenly became quite rare. and it wasn't fun N-E More, for regular guys. people started to take it too seriously.

[MJ]

i was never a Boy Scouts :straightface:

[KateSpade83]

Halloween 2006 was the first time I had a complete outfit with wig and form and since I was in Bowling Green, not Chicago - I decided to venture shopping my first time in complete drag. I was so nervous but found out I pass enough so now shopping in drag is no big deal to me.

Girl Scout uniforms are ugly to me! I like nice authentic Catholic Schoolgirl uniforms!

[Kristen Marie]

When I was in the 6th grade, I went out in the neighborhood dressed up in my mother's dress, her scarf (no wig) and lipstick. It was a real thrill.

[Angie G]

I never dressed as a girl on halloween as a kid. In fact it wasn't until 2 years ago. :hugs:
Angie

[Karen__Starr]

My best memory for Halloween was spending the entire day dressed. At that time I had my hair half way down my back and went from dark brown to dirty bond the evening prior to Halloween and was wearing a size five. I arrived at work, went to my desk passing other employees and a fair amount didn’t recognize me as my hair was a different color, was wearing a tightly fitted business suit (were as a male I wear very loose clothing). Someone came up to me and said this guy Mike thought you were hot until I told him that was Sean dressed for Halloween. All worked out great as lots of people dressed up. The next year I did the same but was shocked to find that about one percent of people dressed. What I did not know (as the first year was my first year on the job) was employees skipped every other year so I was feeling both wonderful and nervous at the same time. That was 12 years ago and the last time for dressing at work and now take the day off and spend time up in Portland Oregon which is a great place to spend Halloween.

When I was married I convinced my wife, sister-in-law and friend to doll me up. They did a great job on makeup and nails but put me into a (what I consider) a horrible outfit. None the less it was better than not dressing as I was married for 14 years and it was difficult to even get one year okay'd by the ex.