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Thread: Advice For Halloween

  1. #1
    Junior Member Invisible Emily's Avatar
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    Nov 2015

    Advice For Halloween


    Hope everyone is doing well with preparing costumes for Halloween. I’m having a bit of a dilemma and I’m looking for a little advice. So Saturday is Halloween and I‘m just spending the night with a few friends. I’ve been debating the last couple weeks going in a costume involving cross dressing mainly because it’s a day of the year where it might not draw as many direct questions. However, both my friends and family I’d be seeing don’t know about my dressing so it’s more or less letting them know for the first time. In a way my thinking I guess was I could semi downplay it since it’s Halloween. I guess I’m just really nervous about the whole situation and was just looking for any input on the matter. Thank you for your insight. Enjoy the holiday!!!
    Last edited by Invisible Emily; 10-29-2020 at 05:20 PM.

  2. #2
    Senior Member Pumped's Avatar
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    Aug 2013
    There has been many discussions on this over the years.

    If you show up, well dressed nice shoes, well done make up, nice clothes that fit well, pulling it off well, close to passing, they will probably know this was not a once a year thing. Most guys doing the Halloween CD thing will have poorly done make up, a dress that doesn't fit from a second hand store, and some way out of style, easy to walk in shoes, not close to passing.

  3. #3
    Silver Member Micki_Finn's Avatar
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    Aug 2016
    Southern California
    All I can say is don’t expect to fly completely under the radar, especially if you put any skill or effort into your presentation. Especially around friends and family. They’ll know if you’re the type of person to dress as a woman on a lark or if there’s maybe more to it.

  4. #4
    Weirdest woman ever! docrobbysherry's Avatar
    Join Date
    Sep 2007
    Orange County, Calif.
    Don't dress as a woman. That's total give away!

    Dress like women dress at Halloween. In a female costume!

    I can only pass on Halloween. Because even women wear masks then!
    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!

  5. #5
    Silver Member Sometimes Steffi's Avatar
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    Sep 2008
    Nation's Capital
    Quote Originally Posted by Pumped View Post
    If you show up, well dressed nice shoes, well done make up, nice clothes that fit well, pulling it off well, close to passing, they will probably know this was not a once a year thing. Most guys doing the Halloween CD thing will have poorly done makeup, a dress that doesn't fit from a second hand store, and some way out of style, easy to walk in shoes, not close to passing.
    First time I did it, I went as a French Maid, with my wife, no less.

    I had all the clothe, except I wore men's shoes, filled my bra with socks and wore no makeup or wig. Oh, and I had a moustache.

    It was exciting and a lot of fun. I don't think anyone caught on.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

    Gender fluid (adj.) - Describes a person whose gender identity is not fixed. A person who is gender fluid may always feel like a mix of the two traditional genders, but may feel [more] like one gender some days, and [more like] another gender other days.


  6. #6
    Reality Check Krisi's Avatar
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    Feb 2014
    Quote Originally Posted by Pumped View Post
    There has been many discussions on this over the years.

    If you show up, well dressed nice shoes, well done make up, nice clothes that fit well, pulling it off well, close to passing, they will probably know this was not a once a year thing. Most guys doing the Halloween CD thing will have poorly done make up, a dress that doesn't fit from a second hand store, and some way out of style, easy to walk in shoes, not close to passing.
    I have posted this same thing many times and every year. This is the truth. You won't fool anyone.

  7. #7
    Silver Member Aunt Kelly's Avatar
    Join Date
    Nov 2016
    Greater Houston
    Pretending to be a crossdresser is a silly way to tell people you're a crossdresser. If you want them to know, tell them. Pretending that you're just wearing an Halloween costume is disingenuous.
    Show the people who matter to you the respect of sharing this about you openly and honestly. Or don't. The choice is yours, but don't tease it.

  8. #8
    Platinum Member
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    Oct 2010
    Western Washington
    I do agree with the others. If your presentation is terrific and you're really passable you may get that questioning look. Over the years I have seen images of hirsute men wearing ill fitting clothes and falling over in heels on Halloween. Personally, I see nothing funny at all. I see it as mocking women. If you have the stature (height & weight) of a women you'll probably be better off presenting as a female cartoon character or superhero rather than an immaculate young woman in dress, hosiery and heels and well appointed makeup and wig, if you're trying to fly under the radar. If you're married or have a girl friend who knows and is on board with your cross dressing, then perhaps you can pull off the immaculate young women presentation as "A little help from my friend."

    Looking back several decades ago my first forays among people as a woman was on Halloween. I did my best to emulate a woman and I think I was successful. I did some shopping trips into grocery stores and donut shops. I was not among close friends. If I had gone to a party I am sure there would have been that speculation, "Is he or isn't he!" As a side comment, when there was the annual "Walk In Her Shoes" fund raiser all the women in the office I worked in would watch for the guys who walked a mite too well in high heels and speculated if the guy was a cross dresser. A guy walking in five inch heels on a concrete sidewalk did not stand a chance of flying under the radar.

  9. #9
    Exploring NEPA now Cheryl T's Avatar
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    Feb 2006
    Even in a female costume if you look Good then it's a tell.
    The only way under the radar is to camp it up and make it look like a guy trying to look like a girl in a girls costume.
    Wear what makes you feel Confident !

  10. #10
    Crossdresser Taylor186's Avatar
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    Jun 2009
    Midwest USA
    Partying in a public setting might get you a pass. I do it every year (except this year). But, partying with friends/family will get you clocked, forever. (And, I'm speaking from experience.)

  11. #11
    Platinum Member
    Join Date
    Jan 2010
    Is it fair to say that you would like these friends and family to know that you enjoy cross dressing? If so, then by all means do it, and make the very best presentation you can. Then, if/when the subject comes up, just be honest and acknowledge that you do enjoy dressing up.

  12. #12
    Member Joyce Swindell's Avatar
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    Mar 2016
    Orlando, Fl
    I have a very large family. One year my step sister and her husband had a party. My wife at the time was not real receptive of the idea of me going in fem but I chose to wear a dress I loved that we had purchased in Mexico while on vacation. Because I had to work late my wife went there ahead of me with the "do whatever you want to do" attitude. So i drove my 1 ton dump truck to the party out in the idle of nowhere and had a really great time.

    The question I got mostly was ..Where did you get that dress? Goodwill...$20 was my answer.
    I don't recall more than funny looks for a few but was also asked to dance by other male relatives!

    I didn't do perfect makeup and accentuated some...bright red lipstick, a little extra rouge etc. Can't be too good! I think that would have drawn more curiosities and such

  13. #13
    Member Star01's Avatar
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    Aug 2018
    Is there anywhere that kids will even be going to private residences asking for candy this year. Watching our local news here in the upper Midwest they're advising people not to do that with the virus cases skyrocketing. Consequently, we didn't buy any candy, didn't decorate and certainly won't go through the hassle of wearing costumes when we don't expect anyone. In the past the kids and grandkids would drop by and show us their costumes and since my family has never been officially told that I'm a crossdresser and my wife doesn't want to see me dressed I have never dressed en femme for any holiday. Kind of spoils the whole mood but that is my world.

  14. #14
    Junior Member Val_Blackbird's Avatar
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    Aug 2020
    Las Vegas, Nevada
    No final decision, yet, but I'm considering just dolling myself up the best I can (which is admittedly middle-of-the-road) and going for it. I figure the chances of being murdered on Instagram Live are less on Halloween than normal, so might be worth taking the opportunity when it's there.

    I doubt anyone would, but if anyone asks about why I'm done better than most guys in costume as girls, I figure I can just say something to the effect of: "I practiced. Go hard or go home."
    💜💜💜 💜💜💜

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    Do we we belong someplace where no one calls it wrong?
    And like the stars we burn away the miles . . . .

  15. #15
    Member Geena75's Avatar
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    Mar 2013
    I think the idea of choosing a recognizable character to dress up as rather than just dressing up as a woman is sound advice. Red Riding Hood, Dorothy from Wizard of Oz, Super Girl -- all can have a nice "ha ha" reaction while you really enjoy yourself.

  16. #16
    Join Date
    Nov 2006
    All I can give is my own expericance.

    UP front my male half is a career Army Officer. I spent time in Special Operations, I went to various badgefinder schools, sis boom ba....My male half is the last person anyone would suspect as being transgendered/cd.

    My best friend is a GG; 6-2 and very curvy and busty. She went as a sorta Jessica Rabbit avatar and I went with a Mae West presentation. We went to the party and....nothing. Until about 10 minutes later when someone figured it out and we all had a good laugh.

    Not once has anyone from that side of my life suspected a thing. Or at least not to my face!

    Do it, have fun and if someone ask, just shrug and deny if you like, or admit if you want. But if you deny don't make a big deal out of it. Don't dwell on it, and don't bring it up. Remember people are honestly denying something usually just say "no" and move on. It's the long drawn out speeches that draw attention.

    Good luck, either way

  17. #17
    Resident Polymath MarinaTwelve200's Avatar
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    Jul 2005
    The only time I went out Cross Dressed was a few years back for our adult Sunday school Halloween party. I wanted to "Shock" the other guests with something different as the previous party was almost lacking in costumes. I thought about coming as a "woman" but that was simply too "uninspired"----Then I got it! A Gypsy Fortune teller! It was both female and Halloween appropriate. I didn't look too bad either. I set up a table , a crystal ball and a deck of tarot cards-----I was the hit of the party.. ALL the ladies wanted ME to read their fortunes---we ALL had great laughs, and needless to say, I WON the Costume contest. I DID discover that CD is a GREAT if not strange way to meet women

    My scheme to reinvigorate the costumes at our parties worked very well ----I came dressed as a dead ringer for MARK TWAIN the next year----but I only came in SECOND in the costume contest---Beat out by an 80 year old "Pregnant Nun"
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