Dressing (or dressed) as a girl for Halloween between ages 5 and 15

[Patti Remick]

Hi all,
I was wondering if any of you dressed - or were dressed - as a girl for Halloween when you were between the ages of about 5 to 15?

I never did/was but looking back I so wish I had.

If you did/were, did you have help and who 'initiated' the process (did you ask or did they suggest?)? If so who helped/initiated (mother, sister, etc)? What did you wear - outer clothes only, from the inside out, makeup, wig, nylons/tights/pantyhose (all the gory details please!)? Was it 'normal' girls clothes or some kind of girls costume (ie ballerina, princess, etc). Was anyone 'made' to dress as a girl for Halloween (whether you secretly wanted to do it or not)? Did you do it once or more than once (several Halloweens).Please tell us your story and approx when this took place (what years). All other comments on this subject are welcome.

Luv and Higs,
Patti Remick

[dragdoll]

I did a couple of times when I was around ages 10-12. First time I wasn't really dressed as girl but as member of Kiss. I did most of the makeup myself (including red lipstick) with help from my mom. She also got me a pair of black tights and made the top part of the outfit herself. She also gave me a pair of black high-heeled boots that she had in the closet and a long black wig to wear with the costume. It was pretty close to being in drag.

The next year I saw an older boy at a Halloween party dressed as a woman and really thought it looked cool. So I was obsessed with dressing as a girl the next Halloween. My mom gave me stuff to wear (wig, dress, pantyhose) and did my makeup, but I ended looking more like an old lady than a cute girl.

I was planning on going out in full drag when I was 15 (trashy blond wig, stiletto heels, halter top, miniskirt, ect) but I ended getting sent to a drug rehab 2 days before Halloween. We did have a pretty fun Halloween party at the treatment center but nobody had a costume except for some members of the staff.

It wasn't until my 20s that I dressed as a girl for Halloween again :(

[Beverley Sims]

Dressing for Halloween was not the big deal for me.
I took in a school play and everyone was enthusiastic to make me look a success.
It really wasn't hard and I became a legend......
For a while. :)

[~Joanne~]

As I stated in my other post titled "Closeted on Halloween" or something close to that, I had many friends that did dress as girls and some that dressed as guys. I was always green with envy though. My Parents always seemed to spring for a costume and mask but I wish they hadn't. Maybe I could have joined my friends ;)

Being young though, you don't know how to approach the subject, hell, we don't to this day but I am sure I missed out on a great night of fun.

[Cheryl Ann Owens]

I never did but my older sister suggested it. It never went further and that may also have been another trigger for me to decide to CD.

But, I remember being about 14 and out on the streets with a friend on Haloween and meeting up with a boy in or neighborhood who was a few years younger. He was dressed completely with makeup and all. He looked great! I was so jealous! Makes me wonder if he continued?

Cheryl

[Ashley Lyn]

was totally dressed as a fairy princess when I was around 8-10.. Was for a church Halloween party! With help from my Mom..
Wore my sister's skating outfit one wear.. Short skirt and matching satin bloomers to match the skirt lining.. Probably age 12..
Mom helped with both..!! Grew very fond of that skirt and snuck it out of the house to wear several times after Halloween...
Thus my dressing started very early in life! Fond memories..

[Joansometimes]

Yes I did go out dressed as a woman for halloween. My mother even helped me choose a dress.:)

[Cheryl James]

Every Halloween from about 7 through 15 or 16. Proper undergarments became a necessity for me (to feel right about my presentation) at about 12. My mother offered to buy me my own bras, even. I, stupidly, and with much consternation, declined her offer. I wish I had a "do-over" on that now.

[Cheryl Ann Owens]

I've had regrets especially when in high school I declined to have a girl friend do complete makeup on me because of my blue eyes. I couldn't let on that I'd enjoy it. But getting back to Haloween.........

I wonder how it might go especially in an enlightened today and enlightened parents if any of us willingly allowed our moms and/or sisters to dress us completely for Haloween, and then after we said to them, "I REALLY liked being a girl and would like to do it a lot more!" Some of us might get very lucky and even be able to live as a girl very often, maybe leading to something better!

Cheryl

[Jannis]

Yes, I dressed in a very pretty light blue party dress. I was around age 12 or 13. My mother and her sister, who lived with us, suggested the costume. They dressed me from panties, bra, slip petty coats and dress to full makeup and wig. They both were enjoying the whole process. Little did they know, I had worn this dress in secret by myself at different times in my CD episodes. I also recall being aroused almost the whole evening going house to house and the neighbors commenting on I should have been born a girl because I was such a pretty young lady in the dress. I was in heaven. I kept the dress on until bedtime and did not want to take off the makeup. Whenever, I was left alone in the house, I would sneak and wear the dress while dancing in front of the mirror. I made many forays around the neighborhood at night dressed to the hilt when my parents were out. I was hoping to be seen, but no one ever saw me. Sounds a lot like now! I was "all boy" back in those days, but I believe my parents suspected I was "more sensitive" than other boys and I enjoyed many things girls would normally be associated doing. Still the same.

[Jennifer in CO]

Here Here!!
This was the 1st Halloween after my intoduction to/as Jennifer the previous June. So needless to say I pestered Mom to do it as a girl for several weeks prior. She relented, so, I did the trick or treat thing in a maroon long sleeved mico-mini dress, with proper under dressing, panty hose and a pair of Mary Janes. After TorT, I had a party to go to at a friends house in the neighborhood where we had just moved from. It was not a dress up party. Mom said she couldn't find her makeup remover so I'd have to go like I was (I do believe she wanted me to be embarass for how I was dressed...didn't work).
Got to the party and after maybe 15 minutes or so no one gave me a 2nd glance. Most of the parents there didn't know me anyway so they just thought I was another lil girl in the mix. An hour later it was a boys vs girls game and I went with the girls - no questions asked. Later, the party gravitated to the boys running around outside and the girls inside talking about boys, classes, etc. I was with the girls.
Mom picked me up at around 10 or so. Got home and amazingly she found her makeup remover...but not the finger nail polish remover. I had maroon nails and shaped eyebrows for the next day at school. Polish remover was waiting for me when I got home from school. Eyebrows took a month to look "normal" again. I loved it...

[Sometimes Steffi]

When I was too old to go trick or treating, one of my younger brother's friends came dressed as a girl. I believe his two older sisters helped. I was so jealous.

[JenniferR771]

Halloweens were difficult. My mother suggested it several times, but I refused thinking the other boys would tease me and I would be humiliated. Or maybe, that she and the other boys would realize how much I enjoyed wearing dresses. So...I was the only one in class without a costume.
One of the other boys in my class (his mother was a beautician) dressed up so perfect--everyone thought he was a substitute teacher. I was envious--stared at him many times.

[RADER]

A few years back, my wife dressed me up in a maids outfit to hand out candy
to the kids. I was nervous at first, but I hated to see the night end. I was having
a great time.
Rader

[Jilmac]

When I was 15 I decided that I wanted to go to a Halloween party that my church was sponsoring, and I wanted to go as a girl. A girl friend, (not a girlfriend but a girl who hung around with me and my buddies) helped me. She and I were about the same size so I was able to wear almost anything she wore. She fixed my up with her panties and bra. I didn't know anything about tucking then but was able to hide most of my male equipment with the help of a very tight girdle. Girls didn't have pantyhose than, but wore stockings with garters, so I wore a pair of hers

I was going to stuff the bra with water balloons but her idea was to fill them (the balloons) with cooking oil because she said it would feel more natural. She helped me with makeup and a styled wig and I wore a lilac colored dress with pink flowers that she let me use. Almost everyone at the party was amazed at how feminine I looked. I won second place in the costume judging, the first place winner being a girl with a superman costume that she made herself. That was my very first outing dressed en femme but Halloween was the only time I could dress and be accepted.
A lot has evolved since that party, I'm a senior citizen now and dress whenever I want and for no special reason other than total enjoyment.

[Diane Smith]

I never dressed femme myself, but when I was 11, a boy in my 6th grade class came to school on Halloween as a very convincing girl. He said his younger sister had helped him with the clothes and makeup. I was almost insanely jealous, hung around with him all day, and regretted for years afterward that he had thought of it first. I completely lost track of Dennis after that, but his presentation was so convincing that I have to believe he had some previous experience at it and is probably still dressing up to this day.

- Diane

[docrobbysherry]

It's NOT too late, Patti. I wasn't 15 when I created this look. But, I WAS younger. Somewhere in my 60's---

233795

[Tina B.]

Never had the pleasure of getting to dress up for Halloween, had I tried I would never heard the end of it from my older brother.
But a few years ago, I had a group of girls, between 12 and 15, around 5 or six of them out trick or treating together. When I answered the door, the girls pushed a pretty blonde girl out front, and let her say Trick or Treat, at that point his voice broke, as he squeaked out his trick or treat, and all the girls started to giggle.
It looked like they where all having a lot of fun trying to fool people into thinking he was a girl. But I think the lucky little dude, was the one having the most fun of them all. He was dressed in a Disney princess dress, and it looked like it was expensive, not just a cheap costume with heels, and he did alright in those heels even on my steep driveway.

[bridget thronton]

I did not but would have liked to

[susan jackson]

When I was 5 - 15 (1971 - 1981), Halloween was not seen as being a big thing in England

[Heather1129]

I'm not sure how old I was, probably about 13-14, we were invited to a Halloween party at my aunt and uncles house on kind of short notice. I had no idea what kind of costume to wear so I went to one of my sisters and said "Do you have a dress I can wear?" She thought a minute, kind of looked me over and went to her room and came out with a dress, slip, bra and a panty girdle with garters and stockings. "Here put this on." I had been wearing my sister's clothes for some time already, so I sort of knew how to do it. I went to my room and put it all on, I remember I put the girdle on inside out so the garters were on the outside, silly me. I couldn't do the stockings so I went for help and thats when she told me it was on wrong. So I fixed that, got the stockings on with some help and then she stuffed my bra with something. I looked ravishing. :) Off to the party where my aunt gave me a wig, but I didn't wear it long, the long hair bugged me. I was in seventh heaven, being in a dress and all dolled up. Little did they know....

Heather

[Ally 2112]

I did when i was about 15 i dressed in a wig sweater and short skirt and had a plastic ladies mask i bought from a costume shop .I did one street in my nieghbourhood and went straight home .Never told anyone

[BillieJoEllen]

My sister had a dress she wore for Halloween that my mother had made for her. When I got into the fifth grade we all dressed up for afternoon class and had a bit of a party. I wore that very same dress to school. It was a colonial girls dress. With the wig and the bonnet on I could have passed as a girl and in fact I fooled just about everyone I came in contact with. The next door neighbor boy dressed as a modern day girl and a boy down the street dressed up as a ballerina. His costume was a very expensive one and we saw him in that costume at least four times throughout the years. I wore pants under the dress and except for the wig that was the only fem thing I wore. Because of some discussions I had with some of the girls in my class regarding my dress wearing I seemed to be 'propelled' into a life of CDing.

[erika_kerrie]

I did once when I was 15. I was part of a youth group and there was a bunch of us, the boys went as the Spice Girls and the girls went as the new kids on the block. I was Ginger, and I loved it. I had a bunch of pics but I can find them :( this was before flickr etc. It was a lot of fun. I was the smallest guy and if I do say so myself I looked the prettiest of all the boys. Two of the girls who made me up kept asking me if I've dressed up before, which I denied of course. Anyways it was a lot of fun the girls as the new kids look much better, but I think I had the most fun out of everyone.
Cheers,
Erika

[Annette_boy]

Yes, yes When I was nine I went as a gypsy with long skirt peasant blouse a bandana and clip on hoop ear rings. I had all the lacy silky undies for a nine year old girl in the fifties. My mom helped me and I made the biggest haul of candy ever that night . Mom let me keep the lingere too

hugs Annette

[Aviatrix]

A lot of common themes. I also dressed as halloween as a girl a couple of times as a teenager. First was 14 or 15 or so and it was in secret. I told my father (divorced parents) I was going to walk around the neighborhood but had some stuff hidden in the woods near my house and changed into that but without any makeup, a raggedy wig, and shoes that were way too big .. at least they were flats. I'm sure I looked horrendous, thankfully it was dark. So while I was walking around the neighborhood I passed by a house of a guy I went to school with and would you know it he tries to flirt with me. I was so nervous I just about broke into a sprint to get away from there, luckily he didn't follow me. Guess I looked good from a distance and thanks to the dark.

The next year I "challenged" my guy friends to dress up and we'd all go out as chicks. While they agreed, I was the only one to actually go follow through with it. With the help of a friend I was surprisingly cuter than before. The great thing was that my buddies were very cool with it and it was a normal night of driving around the neighborhood and hanging out at McDonalds like we normally do on a weekend.

Both good and exhilarating experiences, and I won't forget!

[Athena_]

My mother and sisters dressed me up as a girl for Halloween when i was a pre-teen (maybe 10 or 11 yrs old). I remember the outfit clearly: white party dress, pink satin bow, appropriate undergarments with fake boobs, white tights, black Mary Janes, makeup, and a blonde curly wig. I dressed as a girl each year until high school, one year as a cheerleader. I was already a closet cross-dresser, but I don't think that my mother and sisters knew about it. I certainly did not resist them very much when they suggested dressing up as a girl the first time. I have only dressed up one other time as a girl for Halloween since. In college, my girlfriend and I went and a Prostitute and her Pimp. I got to dress up as the Prostitute. I wish I had some pictures from any of those Halloweens! My wife and I are going to a Halloween party this year, one of our possible costumes is a doctor and a nurse. I am campaigning for the nurse!