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Have you ever dressed up (or been dressed up by someone) as a girl for Halloween?

33 Posts
29 Users
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Posts: 872
Lady
Topic starter
(@marieclaire2)
Noble Member     London, United Kingdom
Joined: 4 years ago

Have you ever dressed up (or been dressed up by someone) as a girl for Halloween?

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32 Replies
5 Replies
(@geniv_cd)
Joined: 8 years ago

Reputable Member     Minneapolis, Minnesota, United States of America
Posts: 228

@marieclaire2 Way back in my college days, one of my girlfriends “talked” me into letting her dress me femme for Halloween. Of course I had to pretend that I was reluctant but with some convincing I agreed to her idea. Inside I was ecstatic! We shopped the Goodwills and second hand shops for an outfit, found shoes and a wig, and then she actually went out and bought me a bra and panties for the party. The afternoon of the party she had me shave closely and did my nails, then gave me a complete makeover and she was an expert with makeup! Needless to say, I was a hit at the party! In fact, several of my friends did not recognize me immediately. I had a great time and got into my costume trying to act as feminine as possible. At the end of the evening I didn’t want to take off my makeup or clothes but had to in order not to blow my cover!

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Lady
(@jillharris1953)
Joined: 4 years ago

Eminent Member     Tennessee, United States of America
Posts: 32

@marieclaire2 Yes,one year my wife helped me dress as a Gypsy woman.  I went to a party and had a great time.

 

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Ambassador
(@gafran)
Joined: 7 months ago

Noble Member     Warner Robins, Georgia, United States of America
Posts: 690

@marieclaire2 

Not exactly. 

I have shown my dressed picture to family and friends who don't know of my real dressing. 

 I told them that this was my Halloween pictures. They really didn't recognize that it was me. My sister wanted to know why I was enfem. I told her it was for a charity event! I didn't what the 20 million why and what for questions! 

Fran 🥰 

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(@cdashley)
Joined: 4 years ago

Noble Member     Oshawa, Ontario, Canada
Posts: 1436

@marieclaire2 I’m a yes for that. Wife had the idea of us going as Brad Pitt and Angelina Jolene. Which didn’t seem that bad until she mentioned I was to be Angelina and her Brad. This was before I had come out to her so I had to play it up that I wasn’t crazy about it but in the inside loving every minute of it. Often wondered why she didn’t clue in when we got home from party and I stayed dressed for another few hours. And to top it off I won second place for best costume .

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(@lauren114)
Joined: 1 year ago

Noble Member     Delaware, United States of America
Posts: 1039

@marieclaire2 At one time, I would have loved it although it never happened.   Now, I'm a woman dressing up for Halloween.

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Posts: 81
Duchess
(@crazycynthia)
Estimable Member     zuid holland, Netherlands
Joined: 1 month ago

My country does not have halloween or somethink like it. I once had a costume party at work and i was hinting on being down for simething like that, but alas, it would be "offensive" or something... 😞

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2 Replies
Lady
(@stereleo)
Joined: 2 years ago

Estimable Member     Las vegas, Nevada, United States of America
Posts: 71

@crazycynthia sad!  (As a) Kid getting free candy and all I have to do is get a costume!  Any more fun and it would be illegal!

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Duchess
(@crazycynthia)
Joined: 1 month ago

Estimable Member     zuid holland, Netherlands
Posts: 81

@stereleo haha, my country does have a tradition called saint martins day. On that day children knock on doors and sing a song in excange for candy 😆 🤣 . But halloween is offcourse way more cd friendly 😜

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Posts: 241
Lady
(@cherylt)
Reputable Member     Honesdale, Pennsylvania, United States of America
Joined: 4 months ago

Yes, as a matter of fact it was my wife who helped. I was not very well versed in makeup so she did it for me. I borrowed a costume, dress, veil and gloves, from a friend and wore my own lingerie and shoes. 

I was nervous but it was unnecessary. All the gals wanted to talk about my makeup and what I was wearing and all the guys wanted a picture with me. It was incredibly fun.

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Lady
(@stereleo)
Joined: 2 years ago

Estimable Member     Las vegas, Nevada, United States of America
Posts: 71

@cherylt I did this once but didn’t get past the door - wife says “I can’t put makeup on someone else” and stalemate-stared at me. Well. That didn’t get far.

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Lady
(@cherylt)
Joined: 4 months ago

Reputable Member     Honesdale, Pennsylvania, United States of America
Posts: 241

@stereleo Too bad she balked. My wife did my eyes and brows for me. I did the rest to set it up. My hands weren't too steady that night LOL.

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Posts: 95
Guest
(@Anonymous 98511)
Trusted Member
Joined: 2 months ago

I could only wish.

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Posts: 1346
Baroness
(@annaredhead)
Famed Member     Cornwall, United Kingdom
Joined: 9 months ago

No but it sounds like a good idea.

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Posts: 599
Duchess
(@jennconn)
Noble Member     Florida, United States of America
Joined: 2 years ago

Marie, yes I did, but I was very young.  I recall I had been interested in dressing like a girl for Halloween and thought it would be fun, so I asked my Mother if it was ok.  Fortunately she said yes.  But once she put together the costume for me, she must have had second thoughts, because she put me in an outfit that was not at all feminine and unfortunately I looked like my usual self, only wearing girls clothes.  I was hoping to actually look like a girl, and found it so embarrassing to be walking around dressed like that.  All in all it was a bad experience for me, but I think that’s what my Mother wanted.  But I’ll never forget the time that I did it.  And obviously it didn’t cure me from dressing later on in my life.

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Posts: 673
 Erin
Princess
(@erinb)
Noble Member     Ohio, United States of America
Joined: 3 months ago

i personally did once many many years ago to a Halloween party everyone thought it was funny little did they know I was a CD I remember it well it was an old black prom dress of my SO she still had and I bought a 5 dollar wig at Walmart stuffed my chest with socks and away we went it was such a big hit my close friend wife had him dressed by the end of the night in a dress was a good time I wouldn’t dare do it again tho 

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Posts: 1933
Baroness
(@ryanpaul)
Famed Member     Outer Eastern Suburbs Melbourne, Victoria, Australia
Joined: 7 years ago

Halloween has only recently Taken off" down here in the "Land of Oz" so I've never dressed for it. My DADT relationship is a "blocker", before I'd even think about it. Other key factors?? We live in gated retirement community, so there aint no "trick or treating" or parties around here.

Last but not least, if anyone else around here found out about Caty, the gossip mill in this joint would shred its bearings.

I would not ever... put my beloved through that

 

Caty

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Posts: 1838
Hostess
(@cdsue)
Famed Member     Delaware, United States of America
Joined: 5 years ago

When I was in college my girlfriend (later my first wife and first ex) helped dress me as a woman for Halloween. I wore her bra, panties, pantyhose, dress and shoes and she did my make up and fixed my hair (at the time it was shoulder length). I was very nervous throughout the night (my first time in front of someone and in public) but it was a lot of fun. I remember there weas another guy there dressed as well.

XOXO
Suzanne

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Posts: 12
Lady
(@kylikki)
Eminent Member     Helsinki, Uusimaa, Finland
Joined: 2 months ago

Yes, 

we once went to a burlesque costume party where I was dressed as Fiona from the Shrek. by my partner. 

We didn't enjoy the party, but we did enjoyed the dressing part, so next Halloween we went to Edinburgh with me dressed just to stroll around the town, get fish and chips and a pint and so on. 

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Posts: 50
Lady
(@miastarr)
Estimable Member     Chicago, Illinois, United States of America
Joined: 2 months ago

I went as Little Orphan Annie when I was in high school.  It got a good laugh, but also let me wear a dress to school and let a little of my femme side out.  Halloween is the best for undercover CDs...

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Posts: 1678
Duchess
(@alison-anderson)
Noble Member     Middlesex county, New Jersey, United States of America
Joined: 6 years ago

I have been walking my neighborhood en femme throughout the year for 6 years. No one has come to my house in the last 20+ years because there are only a few houses on one side of the street, so the payoff is never very good.

For the last 5 years, I decided I would go around and give candy to kids as I passed. Since I'm going out en femme anyway, I'm not backing down on Halloween. A couple of years (including this year) I went with a poodle skirt. Two years ago I went as a bride in a short bridal gown, and last year I went as Velma from Scooby Doo, even handing out Scooby snacks.

I have some photos of me in these outfits here on CDH. Some are private, but a couple are public (from the Halloween contests in 2023 and 2024).

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1 Reply
Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3434

@alison-anderson What a great idea, Alison! 

I live in an apartment building and all buildings are required to have locked entrance doors. We don't have anyone come to our building, now. Maybe I can consider going around our neighborhood.

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Posts: 4438
Managing Ambassador
(@willajay)
Majestic Member     The Middle of Nowhere (TMoN), California, United States of America
Joined: 6 years ago

This is an annual tradition for the Palm Springs girls.

This year is the first time I didn't actually make it on Halloween, but met with the group two days later, en femme.

Most of the group went in feminine costumes on Halloween.

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Posts: 27
Lady
(@love2cross69)
Trusted Member     Ontario, Canada
Joined: 3 months ago

God if only. I know exactly what I’d wear though. 

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Posts: 493
Ambassador
(@beach-girl)
Honorable Member     United States of America
Joined: 7 years ago

Many times. I've been a French maid, a St. Pauli girl, Supergirl, a waitress, Britney Spears & just dressed as a sexy woman.

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