Halloween, when boys can dress as girls

[SIZE="2"]This year it finally happened – a boy dressed as a girl came to my house on Halloween! Stop the presses! Damn the torpedoes! Batten down the hatches! Apparently all is right with the world, at least as far as I’m concerned. Oh, BTW, I also saw a girl dressed as a boy last night...

I stay home on Halloween, and my sister and I hand out the candy as the little costumed locals drop by between 6:00 and 9:00PM, when the tornado sirens, i.e. the “Witches’ Wail,” ends the proceedings. Since we have a very heavy two-part front door, I have to hold it open as my sister wields the boxes of candy. As such, I only get a brief glimpse of the revelers...

At one point, there was a group of middle school-age boys at the door, and they were giggling as the candy was fondled and then snatched (word gets around – we give out the GOOD stuff). Just as this bunch of boys was apparently through, one final kid appeared from the shadows, hiding behind the door. I saw a long black dress, a long black wig, black nails and black lipstick, like a female Goth, or an approximation thereof. The kid shyly, but gently chose a candy bar, saying “Thank you” with an unmistakable male voice. I froze – a BOY in a dress! In THIS town, of all places...

For a moment I thought Pythos found my house, but I live too far from her base of operations. In a flash, the boy was gone, his (her) friends snickering relentlessly out on the shadowy sidewalk. It all happened too fast, and I was left wondering how it all came about – did the boy make a conscious decision to dress against the tide of conformity of small-town Kansas? Was this an expression, or the birth of expression, or perhaps it was an “I don’t care” situation, based on personal feelings of alienation and/or disgust with the status quo. I’ll never know, but I was pleased that a male in this bastion of conformity had the courage to swim against the tide...

I saw many boys dressed as policemen last night, and several girls dressed as fairies, plus the usual ghouls, super heroes and grim reapers. Later in the evening the doorbell rang again, and I beheld a young girl dressed as a boy! She had on black pants with suspenders, a little bow tie, a male shirt, and her cropped hair added to the illusion. Her younger brother was with her, in the usual Halloween garb, but this boyish girl was just as astounding as the girlish boy I saw earlier. Are gender barriers breaking down lately? I was amazed, since I’ve spent many hours describing this gender-specific world I inhabit here on the high plains, for better or worse...

Naturally, I’m wondering if the girl dressed as a boy was also trying to express something – I see choice of costume as profound decision-making, so why would you dress in a way that does NOT express something within? I’m sure if I asked one of these kids why they dressed the way they did, they would probably offer a meek “I don’t know,” and leave it at that, but maybe verbalizing reasons behind doing something is neither important nor necessary. Anyway, it was good to SEE...

Poor kids – they never realized they were face-to-face with the famous Freddy, reluctant “leader” of her own tiny cult! :doh:

Did you encounter any crossdressing kids on Halloween? I was LUCKY this year...:) [/SIZE]

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Originally Posted by Frédérique

[SIZE="2"]I saw many boys dressed as policemen last night, and several girls dressed as fairies, plus the usual ghouls, super heroes and grim reapers. Later in the evening the doorbell rang again, and I beheld a young girl dressed as a boy! She had on black pants with suspenders, a little bow tie, a male shirt, and her cropped hair added to the illusion. Her younger brother was with her, in the usual Halloween garb, but this boyish girl was just as astounding as the girlish boy I saw earlier. Are gender barriers breaking down lately? I was amazed, since I’ve spent many hours describing this gender-specific world I inhabit here on the high plains, for better or worse...

Naturally, I’m wondering if the girl dressed as a boy was also trying to express something – I see choice of costume as profound decision-making, so why would you dress in a way that does NOT express something within? I’m sure if I asked one of these kids why they dressed the way they did, they would probably offer a meek “I don’t know,” and leave it at that, but maybe verbalizing reasons behind doing something is neither important nor necessary. Anyway, it was good to SEE...

[/SIZE]

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Sounds like the little girl was dressed like on of the "Little Rascals", maybe Alfalpha.

Hi Freddy,
no, I didn't encounter any...
I was very proud of my youngest daughter, who I would never have recognised in a hilarious, dark outfit which she put together herself... cute.

I had a lot goin' on yesterday and at the weekend, and spent a lot of time in the car zig-zagging here and there.
I saw lots of (mostly young) people dressed up, carrying on like egits (= me in everyday life) and having a great time.

Your description of the Goth-like kid reminds me of a good friend of mine with whom I've been sharing my CDing more and more.
Often, she recalls her teenage years when she was part of the Gothic-like scene in Leipzig (Anne Clark, etc.).
She stresses that the girls and boys spent hours together doing each others make-up and trying out various cloths - regardless of gender.
It was all just great fun!

:love:Gaby

Way back, some time in the late 1970's, I was taking my daughter trick or treating around the neighbourhood. A boy from across the road, who would have been about 12 years old, was making the rounds with a buddy of his, and they were both dressed like a couple of matronly women. At one point, I overheard one of them say "My bra is killing me".

I secretly admired them for having the courage to do this, but have no idea what their motivation might have been. Perhaps they dared each other, or others dared them, or one or both were secretly CD's and saw an opportunity, or whatever. In any event, they were of an age where I am sure they had plenty of input as to what they were going to wear, and were not under any sort of parental pressure. It may have been suggested to them, because there was plenty of clothing to choose from, but I think it would have been totally their choice.

I have never seen any kids crossdressed that way since, even the girls.

Veronica

We see a lot of crossdressing every year.... Going back 20+ years. Mainly in the High School and Middle school.. The marching band always had a couple M2F when they practiced in costumes.. One football game 4 guys came to the game totally enfemme.. Short skirts and heels and they all looked amazing! Hot!! No one really cared... This year because it rained we didn't have many trick or treaters... There were a couple girls who crossdressed.. One wearing a lumber jack costume and a full beard... "I'm a lumberjack and I'm Ok" popped into my head! Lol.

Back "in the day" as the saying goes boys routinely dressed as girls. What could be easier than to slip on a skirt, blouse, old hat with a dab of lipstick then to dash off and collect the goodies. Candy corn and ginger snaps were plentiful.

Since most of the boys had on their guy clothes under their skirts I doubt that any of them were feeling feminine.


Vieja

Not often, but I've done it handing out candies and that's a blast! It may not be politically correct anymore...we might got offended ! lol

I was at a party of about 30 people where we handed out candy to dozens of kids that came to the door during the 'game'! There were two boys dressed as girls! One eight yearold, the other twelve! I knew them both! It was a lot of fun! The party ended at one am after the exciting game of football! GO CHEIFS!!!!!!!

Not where I live! It's OK to be gay here. But, TG is still WAY OUT THERE for our kids!

I think you may see your middle school Halloween dresser again, Freddie. Here! In maybe 8 or 10 years?

If the young boy was alone I think he was trying out his female personna. If he was with the group of middle school boys and hanging back, it sounds he may have realized it may not have been the best idea to dress en femme. Kids at that age can be very cruel. If he was trick or treating with a group, I bet he would have had a better time hooking up with a group of girls.

I saw one person last night dressed as a woman....or of a characature of a woman, really. He was older than most of the kids, certainly at least teen-aged, and much bigger, too. He wore a white dress with a black pattern on it, and a dark black cheap wig. He also had fashion sunglasses on to complete the incognito disguise. And he was all by himself.

My guess is that he really wanted to go out en femme, but that his macho self-image, or the image that he projects to others, prohibited him from actually doing himself up properly, the way he may have wanted to. That's just a guess. He seemed a little too pretty, for a big guy, to be simply throwing on a dress and saying, "Ah, that'll do", but just sloppy enough to be able to tell his friends, "Yeah, dude, I went as a chick" and get away with it. But he got extra treats from me, just for wearing that pretty dress and venturing out for the evening.

I live back in the woods (so to speak), so I don't get many trick or treaters. In this town, there's still the remnants of the 'adulterated Halloween candy' from several years ago - where some sickos poisoned and rigged candy with razor blades and pins. As such, most families go to the local shopping malls for candy. When I had a part-time job there, I can remember dressing up and handing out candy then. (Some fun costumes then ...)

Still, I saw some very good 'en femme' people (with and without kids), including several with cleavage and corsets.

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Originally Posted by TGMarla

My guess is that he really wanted to go out en femme, but that his macho self-image, or the image that he projects to others, prohibited him from actually doing himself up properly, the way he may have wanted to. That's just a guess. He seemed a little too pretty, for a big guy, to be simply throwing on a dress and saying, "Ah, that'll do", but just sloppy enough to be able to tell his friends, "Yeah, dude, I went as a chick" and get away with it. But he got extra treats from me, just for wearing that pretty dress and venturing out for the evening.

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[SIZE="2"]The Goth boy/girl I encountered seemed very nervous about how he was dressed, but I think his peers had a lot to do with that. Once separated from his “group,” the boy seemed more at ease – he composed himself (herself), and got the candy. I would’ve given him/her the whole box, but he was gone in a flash. I got the feeling there was a certain amount of inner conflict going on – call it MtF crossdresser intuition…
:sad:[/SIZE]

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Originally Posted by karanne

I live back in the woods (so to speak), so I don't get many trick or treaters.

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[SIZE="2"]Back in Massachusetts we lived at the end of a very long driveway, so the Halloween kids were scared about making the journey, let alone coming to the door. Also, in kid terms, it wasn’t time effective – too sparsely populated for decent trick-or-treating. When I went out, I would walk a mile to the nearest housing development, and then commence hauling in the loot where there were plenty of houses. The Kansas town I now live in is ideal for nocturnal Halloween ramblings, and we had a healthy compliment of visitors this year…
:)[/SIZE]

I can't say that I encountered any crossdressing trickor treaters - but then, maybe they were really good at passing. One little guy was dressed up as a tractor-trailer rig! MtM (male to machine?)

I love it when that happens!

This year, no boys in dresses, a couple girls in male costumes, but not overly masculine-looking. Last year there were two boys dressed as girls of about the age you're talking about that went around together. The one made a point to make it clear that he didn't like it, but I think he protested too much if you know what I mean.

I saw a lady coming out of the local McDonalds wearing a half-man/half woman outfit, but she had a winter coat on, so I couldn't see her outfit well.

Carol

Back in the early 70's if we were running low on candy, my mother and sister would throw a dress and wig on me, then send me out trick or treating to get more candy. I never thought much of it.

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Originally Posted by Frédérique

[SIZE="3"]Just as this bunch of boys was apparently through, one final kid appeared from the shadows, hiding behind the door. I saw a long black dress, a long black wig, black nails and black lipstick, like a female Goth, or an approximation thereof. The kid shyly, but gently chose a candy bar, saying “Thank you” with an unmistakable male voice. I froze – a BOY in a dress! [/SIZE]

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Oh gosh, damm it ... he disappeared too quickly. If that happened to me I would have wanted to say (after I heard his boy voice) "you, in your costume are special and so you get extra candy!" and then I would have given him triple the amount I gave to the others :)

When I was in fifth grade I dressed as a colonial girl for our annual all school Halloween party. No one could guess who I was. Around that time of my life I was constantly being told that I looked like a girl. I wasn't a CDer at that point. Some girls were teasing me after Halloween that I didn't really know what it was like to wear a dress because they knew I was wearing my pants underneath the dress. When home alone I tried the dress on without pants. I reported this to the same girls. They came back and told me that my cotton boy shorts weren't allowing the dress to feel the way it should and therefore I still didn't know what it was really like. Once again I secretly tried it at home. Had a few more conversations in the same vein and before long I was trying on my sister's clothes. It was when I put on a girdle and nylons and a tight skirt that I became a CDer. Before that it was curiosity only. Once I knew that I liked doing it I never engaged in conversations like that ever again.

Last night at work there were some high school girls that came in the store in ****ty fairy costumes. While they were shopping I wax telling my co worker that I want to go "in drag" for Halloween sometime again. One of the girls overheard me and said the her and her friends would love to do my make up and that they thought boys and men that dress like girls were so hot. Well I'm no perve and they girls well way too young, but I couldn't help but think that some lucky young crossdresser out there in highschool land gas at least four young ladies that will support him lol. There may be some hope for the younger generation lol

I passed out the candy at our house and did not see a single boy dressed as a girl nor a single girl dressed as a boy.