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Thread: Is Halloween perfect for the first time venturing outdoors dressed x

  1. #1
    Junior Member
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    Is Halloween perfect for the first time venturing outdoors dressed x

    My wife and I are looking for help in venturing outside for the first time. We are thinking Halloween as we can both get dressed up and we will not have the fear of someone recognising us. What would be the perfect costume/ dress? Or duo ?
    💋x

  2. #2
    Member Marketa's Avatar
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    Morticia and Gomez Adams. You being Morticia and your wife Gomez.

    Or Thelma and Luisa?

    Or it doesn't have to be pair costume and then Marilyn Monroe?

  3. #3
    Hot Geezer Girl docrobbysherry's Avatar
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    Don't dress as a woman on Halloween. A common CD mistake!

    Dress like women do. Wear a woman's costume!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  4. #4
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    I think women have some sort of radar to ferret out cross dressers. Once I was waiting at my local Kroger grocery store and overheard several female employees huddled together watching and commenting on a male co-workers who was nicely attired as a woman, no Disney or cartoon character...a business woman in skirt, blouse, heels, hosier, wig and makeup. All the comments were betting he was a cross dressers. My observation? Definitely a cross dresser who was passing nicely, except he went out of his way to engage with his fellow co-workers. Whenever there was the fund raiser of "Walk A Mile In Her Shoes" the female observers were pointing out who they thought had to be a cross dresser.....four in spiked heels? Come-on.

    The times I ventured out on Halloween it was always as a woman as described by the Kroger-guy. With hindsight that may have been too adventurous. What would be the takeaway if someone who you know met you and you were a wicked witch or a Disney fairy? Cross dresser trying to not appear as a cross dresser? Women will see you right through the disguise.

    As a duo? Maybe, if you're not a six foot one, 200 pounder like me, but a five foot six, 130 pound guy, go as a switch..reverse the rolls....example Batman and Cat Woman?

  5. #5
    Platinum Member kimdl93's Avatar
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    I can only recall one Halloween party where someone was crossdresser. Frankly, even though I was deeply closeted at the time, I was a bit embarrassed for him and maybe more than a little offended by his ridiculous, over the top caricature of a woman. Oversized breasts, Daisy Dukes, impossibly high heels, cheap blonde wig and garnish makeup. Despite his deliberately absurd appearance, my wife immediately speculated that he must be a gay crossdresser.
    Remember always that you not only have the right to be an individual, you have an obligation to be one.

    Eleanor Roosevelt

  6. #6
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    When we were younger my wife and I went as Sonny and Cher. And I was told by many I was a very good Cher.

  7. #7
    Miss Conception Karren H's Avatar
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    Halloween is a good time, so are ren fairs! I always see a number of TG/crossdressers at our Pittsburgh Ren Fair. A chance to dress up and wear corsets!
    Current Obsession - Breasts and Lingerie!

    .......My Photos

  8. #8
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    I'vegotta agree with doc...if you just dress as a generic 'woman' for Halloween you'll definitely out yourself Maybe pick a female 'character'

  9. #9
    Silver Member Geena75's Avatar
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    It sort of depends on where you are going out. If you plan to see people you know, don't over-do it. Wear flats, rolled up socks for forms, etc. You want the impression that you are dressing up for a gag. If you won't see people you know, you can doll it up a little more.

    I remember one couple dressing up as Red Riding Hood and the wolf, with the GG as the wolf. Dorothy and the cowardly lion, Alice and the Cheshire Cat, etc. I'd recommend getting a costume, not just women's wear.
    www.flickr.com/people/196660660@N08/

  10. #10
    Junior Member JayBird's Avatar
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    I agree with flipping the gender. Adding to Morticia and Gomez. She is Robin Hood, you are Maid Marion. She is Fred, you are Daphne. I know I cannot pull off a female superhero, because of my upper body hair (arms and chest), so the Renn-fair dresses, Victorian-style, and even the Velma or Daphne style can have enough coverage depending on what you work it. I am striving for Velma this year myself. I'm still searching for the perfect long sleeve orange top.

  11. #11
    Life is more fun in heels Genifer Teal's Avatar
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    You can certainly get away with it, but It's not likely you'll be hiding it. Unless there's a really strong and believable reason. You chose to dress as a woman and you're also not very good at and most of the things you would enjoy about being dressed as a woman. You skip so when you get down to it if you really want to hide it. Halloween isn't gonna help you.

  12. #12
    Gold Member Sometimes Steffi's Avatar
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    All of the above.

    The first time I went out dressed was at a Halloween party with cis friends. My wife and I went out at a butler and a French maid. I don't know why my wife agreed to it but it was before she knew that I was a crossdresser. My costume wad very official looking including a tight-fitting leotard with lacy edges and fishnet stockings that I bought at a dedicated tights and stocking store and a short satin skirt and lace wristlets that I probably got at a costume store. I didn't do it all up to keep the secret from my wife. I got black bikini men's undershorts that fit invisibly under the leotard. I think I borrowed one of my wife's bras and stuffed it with rolled up socks. I wanted to at least wear lipstick, but she got all freaked out about that. I also had a beard.

    I had some interesting reactions. There was a guy behind me who must have taken me as a GG. When I turned to face him, his eyes really bugged out when he saw that I was a guy. One other guy stuffed a dollar bill under my bra. I wasn't the only French maid there, but the other one was a GG. We had a discussion about where I got my fishnet tights since she couldn't find any.

    When I've gone out with the gurls, I've always worn a female costume, like a mermaid, Hooter's girl or Wonder Woman. Sometimes I bought a full costume at a costume shop. Other times I've bought all the pieces separately. I went in makeup and wig appropriate to the character that I was portraying.

    I also went to the Renaissance Faire several times dressed aa a girl. The first time, I went alone and rented a wench costume. The other times, I went with a CD friend and her wife in a purchased costume.

    If you want to hide in plain site, don't make yourself look too much like a woman, and don't wear any expensive costumes. Like no makeup, or at least very minimal, and rolled up socks or water balloon breasts.
    Last edited by Sometimes Steffi; 09-15-2024 at 08:55 PM.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

  13. #13
    Gold Member bridget thronton's Avatar
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    Witch costumes are good - I was Ana from frozen one year

  14. #14
    Silver Member prene's Avatar
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    That is how I came out to a few friends.

    I pretended not to be into it, with a few gg friends but it worked out.

  15. #15
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    I don't think you'd be fooling anyone by dressing up on Halloween, the immediate reaction from others especially women is that you are most likely a crossdresser, unless you literally just put on a dress and make no effort- in which case you're actually missing out on the fun side of crossdressing- you are unlikely to get away with it. Make too much effort and people will definitely assume it's not your first time. Most guys don't chose to dress up as a woman on Halloween, so for those that do, people will assume it's something they like doing, not a problem unless you're trying to hide it.

  16. #16
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    My perfect costume would be a sparkly mini dress and high boots as Taylor Swift and my wife going as her football playing boy toy. Halloween is a great opportunity to dress in public but like others have said its also the perfect opportunity for others to learn your secret.

  17. #17
    Senior Member Jenn A116's Avatar
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    I'll be going to our group meeting in mid-October dressed pretty much as women tend to do when the season is here. Not a fancy costume. Not a scary costume. Just me trying to look like a typical (female) theme park tourist.
    Jenn A --- nothing fancy, just me.

  18. #18
    Crossdresser Taylor186's Avatar
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    If you go local you'll likely be recognized no matter how good or bad your costume is. You'll also get recognized if your wife gets recognized, assuming you go as a couple. If you go to a friends party you will certainly be recognized and likely clocked as a crossdresser or gay or trans or some combination (speaking from a long ago personal experience).

    That said, since that first time I've gone out en femme a couple dozen times at Halloween (I just counted the photos). I go to an annual party at a much bigger town 45 minutes away. This guarantees me some level of anonymity. I always wear a costume.

  19. #19
    Pantyhose for everyone! Jennifer_Ph's Avatar
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    I am out to the world, so all Halloween does for me is allow me to dress ****tier. lol!
    xxoo
    Jennifer

  20. #20
    Resident Polymath MarinaTwelve200's Avatar
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    Sure, just space it a few years apart, otherwise people will get suspicious.

  21. #21
    Happy 2 B Here Mercedes's Avatar
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    My spouse and I went to a friend’s James Bond themed birthday party and I went as a Bond girl and my wife as Bond. This was the only time I have been out dressed but it worked great and I got to wear a LBD, heels, stockings and was trying to be sexy. I think this would be a great joint costume for Halloween if you got the supportive partner.

  22. #22
    Senior Member kimmy p's Avatar
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    Yep. My friends have probably guessed after dressing at Halloween for the past 15-16 years now. Not one comment from anyone that matters.

  23. #23
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    I have to agree with Kim's comment (#5). I have seen too many times women huddled together speculating whether the man is a cross dresser. Looking too good as a woman at Halloween or a bad attempt at levity seemed to get the same speculation. And, if they are watching guys parading by on the street during a "Walk A Mile in Her Shoes" event, it's whether he is negotiating walking in heels to well.

  24. #24
    Gold Member Sometimes Steffi's Avatar
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    At an office job a very long time ago, we had a company cafeteria in the building.

    One Halloween, this server dressed as a woman. My question, is he or is he not a crossdresser. The next year, he dressed again. Yup, he's a crossdresser. Third year, dressed again. I don't even remember what he wore.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

  25. #25
    Silver Member NancySue's Avatar
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    I join those who don?t think it?s a good idea, unless you?re willing to be read. Several years ago, the husband of one of my wife?s sorority friends, dressed like a southern belle. His wife dressed like Rhett Butler. After they left, we both agreed, he?s a cder. Later, at a sorority lunch, he was kinda the talk/whisper.

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