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Thread: Closeted dressers on Halloween

  1. #1
    Gold Member ~Joanne~'s Avatar
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    Jan 2012

    Closeted dressers on Halloween

    I have been here two Halloween's now. Every year, some of the seasoned dressers start raining on the parade, as it is, about dressing on Halloween. It's actually already started again. I am proud that some of us actually present well enough, or are confident enough, that every day that they chose to go beyond the doors, they are able to do so and the world doesn't end. There are no lynchings, hangings, or overly bad experiences.

    There are a lot of us though they haven't conquered those fears yet, may never do so, or may have an agreement with our SO's not to do so, or any one of thousand excuses that we may have for not going past that threshold as easily as they do.

    For a closeted girl, Halloween is the perfect excuse to get out past that door. Do not let anyone keep You from doing so if that is what You chose to do. While I agree that if Your really good at Your makeup, presentation, and walk naturally in Heels and such, there is a chance that those that You encounter will think Your dressing is more than a "costume" but should you really care on that weekend? NO, you shouldn't.

    The experience is worth the risk in my opinion. Most of the people you may encounter you may not even know (if, like me, you go a bit out, away from home) and will never see again. The experience is beyond any words I can type here. To feel the wind on your legs, to have your hair blowing, to hear your heels clicking the pavement, to just be comfortable and be yourself beyond the confines of your self imposed prison is worth more than gold itself.

    Halloween is on Friday this year. You have a couple days before that, the actual day, and the weekend after. You could go out a couple of times this year. The worse that could happen is you find out that You actually prefer to be a in the house dresser, or it may be that gentle push, another baby step, you need to go out more any time that You feel like going out.

    I am not going to lie to you, once you've been out, You will want to go out again. There's no doubt about that. I wait, myself, for this season to come along every year. Hopefully at some point I will stop waiting but until that day comes, I look forward to this season. If your like me, or this is your first time thinking about it, DO IT. You'll regret it come November 3rd when it's too late to have an "excuse" for being out just because you listened to those that are beyond where we are with our dressing.

    Food for thought
    Flip Flops were made for Beaches & Bath Houses, We have neither in 2017. Lose the flip flops!

  2. #2
    Style Icon Sara Jessica's Avatar
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    May 2008
    The OC, California
    I wouldn't rain on anyone's parade. Halloween is the perfect time for many in our community to step out for the first time. I'd be lying if I were to say my first steps into this wonderful world of ours weren't on Halloween, specifically three years in a row back in my college years. But I'd also be remiss if I didn't point out that for me, personally, Halloween has long since ceased to have any luster when it comes to my feminine expression.

    Just because for me it is "been there, done that" doesn't take anything away from the opportunity it creates for many first-timers out there, not to mention that there are plenty of us who still love the holiday despite having a significant feminine presence in the real world.

    I hope everyone enjoys what Halloween means to them and Joanne, you are so right. Halloween may very well be a gateway drug to bigger and better things!!!
    Like a corpse deep in the earth I'm so alone, restless thoughts torment my soul, as fears they lay confirmed, but my life has always been this way - Virginia Astley, "Some Small Hope" (1986)
    Sunlight falls, my wings open wide. There's a beauty here I cannot deny - David Sylvian, "Orpheus" (1987)

  3. #3
    Aspiring drama queen Isabella Ross's Avatar
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    Aug 2014
    Joanne, mission accomplished. You've got me thinking of the possibilities...

  4. #4
    There's that smile! CarlaWestin's Avatar
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    Jan 2011
    Area 51
    This year, I'm really feeling the attraction of Halloween. I really, really want to go to Freemont St. this year wearing the sexey maid dress from my profile picture and full MAC makeover. I want to hear comments and compliments and "OMG!, you're a guy?" I might just offer up to my wife that I want a choice of this or staying home and handing out candy as a sexey maid. Like Rader did one year. I'm getting older and Halloween is just the perfect honest enabler event for a crossdresser. Now then, which maid's dress. Authentic pink housekeeper? Skinny sexey? Or the new tight one that fits my largest boobies?
    Last edited by CarlaWestin; 10-05-2014 at 10:45 AM.
    I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
    My new maid's outfit is cute. Sure fits tight.
    And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
    Smile, Honey! You look fabulous!

  5. #5
    Platinum Member Angie G's Avatar
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    Jun 2006
    just west of syracuse n.y.
    I've been of on 3 halloween And foved it. If any of us girls are thinking of doing if I say go for it. Just be safe about it.

  6. #6
    Platinum Member
    Join Date
    Oct 2010
    Western Washington
    I am an in-home cross dresser. Years ago I decided to put my toe in the water on Halloween. I had been out for a drive en femme, and, on occasion I did get out of my car and stroll through a very 'secure' residential neighborhood. But, the two forays on Halloween were with the intent of actually forcing encounters with people. I was a lot younger and I felt, as I still do, that younger cross dressers' antics on Halloween are viewed differently than with oldsters, such as I at my current age.

    On one occasion I went into a Winchell's Donuts House and bought donuts. I received compliments from the cashier on my presentation. The second time I went into a Safeway and bought a bottle of soda. I encountered another shopper, a young male, had a good laugh at a male in a dress. I guess he had not figured out it was Halloween.
    Did I enjoy the experience? I found forcing an interaction was overrated. However, I will concur the feeling of the cool fall breeze caressing my legs was exhilarating, especially when the breeze was strong enough to cause me to grasp my skirt of my dress and slip so they would not whip through the air, a mannerism I've seen many natural females do in the wind.

    All in all I would encourage an outing on Halloween, even if there is no intended destination, no party. Of course, if you're accompanied by your wife who is costumed, then there is a greater prospect for interaction, a visit to a restaurant, a movie date, etc. A lone guy, especially an oldster, may be viewed exactly for what it is: a cross dresser taking advantage of the date on the calender.

    I live in a small city (200,000) with many secure residential neighborhoods. When I have the opportunity in the evening (8-9 PM) I do take strolls in the cool air. I love it. I especially love the evenings that are rainy because there are less people on the streets and an umbrella is ideal for obscuring my male face. I manufacture tasks to accomplish; return books to the library or mail a letter at the post office drop box. Once you have made the first trip out the door at a bare minimum the trip will satisfy that pent up desire to expand your horizons. You may decide, "Well, I did it!" and it's over. Or, "That was easy!" and do it some more.

    My wife is taking a trip out of state in late December or early January. I'm looking forward to a cold night and having my legs massaged by "Jack Frost."

  7. #7
    Gold Member ~Joanne~'s Avatar
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    Jan 2012
    Quote Originally Posted by Sara Jessica View Post
    I'd also be remiss if I didn't point out that for me, personally, Halloween has long since ceased to have any luster when it comes to my feminine expression.

    and Joanne, you are so right. Halloween may very well be a gateway drug to bigger and better things!!!
    I think that is what has happened with the seasoned dressers. It's lost it's appeal and rightfully so. I fully understand not having any desire to go dressed on halloween, femme or costume, but for some it's a chance to experience the feeling of truly being out, even if for just a few hours, 15 minutes, or whatever time they spend out and I just don't want them to miss the opportunity because someone told them the world knows your a CD because your out on Halloween.

    If some one says "OMG, it's a guy dressed as a woman", you say "OMG, it's halloween" it's a better excuse than having a list with bra and panties sizes when out shopping for your things at least Halloween is more believable.

    If any sister has had this unending desire to kill curiosity, this is it. There is no other time of the year that you can take advantage of and yes, this could be the baby step to more sister's being out there.

    Quote Originally Posted by CarlaWestin View Post
    I might just offer up to my wife that I want a choice of this or staying home and handing out candy as a sexey maid.
    I'm not going to lie to you Carla, I think people would find it "creepier" to see a guy dressed handing out candy to kids than if they encountered You on the streets or at a party but by no means am I saying You shouldn't. Celebrate the holiday any way you see fit because just like there is no right or wrong way to dress, there is no right or wrong way to enjoy halloween

    All in all I would encourage an outing on Halloween, even if there is no intended destination, no party.

    My SO and I enjoy just going to a metro park and doing some pictures. The parks are pretty empty this time of year and your out there! Plus natural light made some of the best pictures I have ever taken! Last year I only had time for one trip out but this year I am actually hoping for a few and a few different places I may not normally go, especially dressed.

    Of course, if you're accompanied by your wife who is costumed, then there is a greater prospect for interaction,

    Closeted dressers probably wouldn't be out with their SO's unless the "closeted" includes only her knowing. With that said, it is a great Idea. Dress the wife as a pimp and get your highest heels out and your shortest skirt and get out there
    Flip Flops were made for Beaches & Bath Houses, We have neither in 2017. Lose the flip flops!

  8. #8
    Dreams can come true Dana L's Avatar
    Join Date
    Dec 2012
    Halloween is defiantly the gateway for many of us. My first time out as Dana was on halloween a few years ago. Found out I really like being out. Still my wife prefers me not to go out and my own fears are a factor too. Because of halloween though I have done some small steps, like going for a drive dressed, or walk my dog late at night, I even got gas fully dressed (paid at the pump of course). Next step, the drive thru. Enough baby steps and maybe I'll be comfortable with going out dressed often, but if that day comes I won't look down on those using halloween as their chance to go out, I'll remember when I was that way and encourage and reassure them. Till then I'll just keep putting one heel in front of the other.

  9. #9
    Part-time girl... Tracy Hazel Lee's Avatar
    Join Date
    Mar 2008

    Go for it

    I completely agree... Halloween IS the 'gateway' to breaking out. And will almost certainly chip away at the fear that one conjures up over leaving the safety of their home. It was my first ever outing, and yes, the taste of it is not something that is easily forgotten, but not impossible. If enough time passes between getting out, those little inhibitions that you experienced before your first ever outing, start to creep up and accumulate again. This is exactly what happened to me. I could remember having fun going out with friends many years ago (about 7 or 8). But lost a lot of the desire to leave my house over the years. Mostly because I didn't want to go out alone.

    I just recently was able to get out again, with some friends I actually never expected to see again, and it was straight over the top for me. I really did forget how much fun it was. And because so much time had passed in between, the desire to get out again is stronger than I have ever felt it in the past. But for myself, the real kick in the pants I needed to push through the fear, was to be with friends. This may not always be possible with Halloween, but for other outings where Halloween is not your excuse, even just having 1 other CD friend go out with you, makes a world of difference in comfort level.

    But getting back to Halloween, if you have a desire to do it, then go for it. It's the best excuse to dress. I would also agree, don't half-ass it. Go all out, you will enjoy the experience far more. All the times I have ever done it on Halloween, the majority of the people attending the party were all direct friends of mine, that have known me for many years. Most of them, since high school. I blew their minds last year, and NONE of them suspected anything. Or at least, never said anything to me that would imply that someone had figured me out. I plan on doing it again this year. Now, I would be surprised if nobody starts prying around this time though. Two years in row? And I'm even going to try and kick it up a notch. Blow their minds again. As I mentioned, this group of people have been my friends for a LONG time. I really don't believe that if I decided to reveal that this is more than just a Halloween costume, anyone would suddenly dis-own me or treat me badly. I am going to attend the party with the distant possibility that somebody may ask the 'right' questions, and I'm not going to lie about it. I'm actually at a point in my life and with my dressing now, that I almost don't care if my friends know anymore. The only fear I have attached to this, is truly not knowing the outcome. But for Halloween, I'm willing to take that risk. It's just too much fun to pass up.
    Tracy Hazel Lee

    @URNA @Flickr

  10. #10
    Gone to live my life
    Join Date
    Aug 2013
    Hi Joanne,

    Well said. I have only been here for just over a year and I remember the "rain makers" from last October. Now in fairness many were trying to express that if you choose to go all out femme and do too good a job you may accidently out yourself and that is probably good advice to give and take note of. However if you have a good background story to explain your expertise (e.g., been practicing for months, had a GG friend help with make-up) you should come out unscathed. But those who get a bit shall we say "overzealous" with the mantra that being a woman is not a costume but a way of life, all I can say is "relax a bit". It think most here understand that and nobody is trying to denigrate women by saying I am going out dressed as a woman for Halloween. Indeed if you are going to take that stance then the same could be said about any of us who go out dressed "en femme" in the Vanilla world. Some can and will go out and some won't . . . so please give those who can't this one time of the year to enjoy what many of us take for granted.

    I say enjoy Halloween to the best of your ability. If you choose to be a Zombie Girl then enjoy and if you choose to be as authentic a woman as possible . . . well . . . enjoy.



  11. #11
    Silver Member Maria 60's Avatar
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    Sep 2010
    No rain from this girl on any parade. Since on this site Maria is more complete and with the help of everyone here and of course my wife, I am much more confident now and the last three years Ive gone out and cant wait. I hope we all have a safe and fun Halloween.

  12. #12
    Full Geek Status Adriana Moretti's Avatar
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    Nov 2013
    NY & CT
    I couldnt agree more and recently did a fluffy article on this exact is the time if you havent been out before. It's the one day ......I hope some of you first timers get out there and good luck.

  13. #13
    Member Ilsa's Avatar
    Join Date
    Jan 2014
    Central Part of the Empire State
    Never was I more excited or relieved when I went to my first Halloween party. After much consternation I just did it! These were my true friends and if they didn't accept the way I looked then I knew they really weren't as close to me as I thought. Much to my relief they were astonished at how good I looked and this made me happy. Caring how you look is very important on Halloween; I say this because also at the party was a guy in a sheer nightie who was also wearing a shower cap on his head and was unshaven with no attempt to make himself more presentable. When I saw him I was relieved that I was not the only one at the party dressed, though I could hardly say he was, but I was also perturbed because it seemed disrespectful to those of us who care about their appearance when they dress.

    So I guess what I'm saying about a Halloween adventure is do it right! You'll feel better and more confident and you won't be like those who exaggerate their appearance to make it look like a Halloween prank in order to cover up their insecurity.

    As always,


  14. #14
    Platinum Member Beverley Sims's Avatar
    Join Date
    Nov 2011
    Lowestoft UK. Beverley was here.
    I don'tknow about closeted but I am looking to have a good time this Halloween.
    Just don't know where yet.
    Work on your elegance,
    and beauty will follow.

  15. #15
    AKA Lexi sometimes_miss's Avatar
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    Nov 2008
    The state of flux, U.S.A.
    Quote Originally Posted by ~Joanne~ View Post
    . There are no lynchings, hangings, or overly bad experiences.
    Uh, yeah, there are, but most people here prefer to ignore/forget about them, because it doesn't fit with how they want to believe the world feels about us. The pink fog here is thick indeed. Remember too, that a Halloween costume is something we actively choose. And whether you want to believe it or not, any 'normal' guy who chooses to go through the trouble to shave, pluck, coif, wear high heels, etc., will automatically be suspect of being gay/TS. Because from the rest of the world's point of view, why would we go through all that trouble when there are lots of costumes that might attract women instead of make them question our sexuality?
    Some causes of crossdressing you've probably never even considered: My TG biography at:
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  16. #16
    Banned Read only
    Join Date
    Apr 2012
    I HAVE attended probably 20 or so Halloween events "dressed". I have yet to attend one where alcohol was not served. The vast majority of attendees at these events drink... meaning they care even less about who is dressing as what or why. They go to have a good time, NOT TO BUST CDers or keep track of who is wearing what.

    CCDs need to find a way to go. There is NO BETTER WAY to escape one's closet for the first time.

    OR spend another year kicking yourself.

    It's totally Ones' call.

    As an aside, it is without doubt THE time when GGs are highly "receptive".

  17. #17
    A lady in the making..... Erica Marie's Avatar
    Join Date
    Jun 2009
    The rainers always find something bad in everything. I by no means am seasoned on being out, but one thing halloween can do is allow even the seasoned dresser to have some fun. I myself prefer a discreet, soccer mom look. I have a hard time clubbing because I dont fit in, just not my style of dressing. BUT halloween opens a whole new door. A door that allows anyone to loosen up. Even a soccer mom has a wild side and needs an excuse to express it.

  18. #18
    Transman Andy66's Avatar
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    Jul 2009
    Vegas, Baby!
    Yay Halloween! Definitely go for it, and go somewhere fun with lots of people if possible.

  19. #19
    Aspiring Member Genny B's Avatar
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    Sep 2010
    I like the comfort of knowing if I do get pulled over or something like that I can fall back on the line, I was at a party! Kind of like how it's ok to shop for women's stuff in late November and December as it's Christmas Shopping!

    Genny B
    Dani (Genny before Transition)
    All Girl!

  20. #20
    Junior Member Kevin_unknown's Avatar
    Join Date
    Mar 2012
    I've been thinking about going to my University dressed in a female costume on Halloween. A few people I know of have done it in the past, however chances are very slim that I will actually do it, it is fun to think about though :P.

    However due to my current living situation I can't exactly do that without answering a few questions from the family.

  21. #21
    Member Athena_'s Avatar
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    Apr 2014
    Illinois USA

    Thanks for the ideas! I have not dressed up as a girl for Halloween since my early teen years. Maybe I can get past that door this year........

  22. #22
    Junior Member
    Join Date
    Jan 2014
    There is a huge event locally on Halloween where the entire downtown area is closed off and people in every sort of costume imaginable flood the area. Were there ever a time to go out dressed however you choose, an event such as this is ideal.

  23. #23
    Aspiring Member
    Join Date
    Apr 2013
    Eastern US
    I know how liberating and exhilirating it can be! The best part is that you have an excuse to be out and dressed, and safely. On one occasion many years ago I went to a party dressed as a bridesmaid. I can't remember my wife's costume probably because I had so much fun. I think people sensed that I was enjoying it TOO much. But in my area and among small towns there are no real big parties to go to. The one I did go to was at a now-closed restaurant / club where I knew many people. Having a guy pull me onto the dance floor was a thrill. I didn't wear heels but had flat white pumps. And I was fully made up.

    My wife now is not a party gal and I'm laid back about partying now. But I would so love to spend an afternoon at a salon getting "the works" for a party. At least the gals at the salon would think it was for a party. Then I'd wear a nice long flowing ball gown or maxi dress. I wouldn't want to leave the party!

    Now here's another idea aside from Haloween. There are often LGBT events and parades in some larger cities. So none of us are restricted to just Haloween. I know of one event that has been published showing many CD's and usually the reactions are positive. If caught by someone you knew, you can always do the "I did it on a dare." excuse.


  24. #24
    Senior Member samantha rogers's Avatar
    Join Date
    Jan 2014
    SE Michigan
    Well, I go out quite a bit, and depending on where Im going I dress for the occasion. For me, Halloween will be our local TG club where there will be a huge party. So, forget decorum...haha...that night its going to be about me having fun rather than worrying what anyone thinks...just an excuse to get a little More a matter of me as a woman, enjoying the chance to wear a Halloween costume as a woman, rather than to simply look like a woman. But, sure, for someone who does not get out normally, what better night than Halloween to give it a try?
    Last edited by samantha rogers; 10-06-2014 at 12:00 PM.
    Every fear that held me back, when faced, has proven to be hollow.
    Courage is not the lack of fear, but the willingness to ignore it.
    It's your life. Make it count.

  25. #25
    Any Ventura TG's here? Sheelah's Avatar
    Join Date
    Nov 2013
    SoCal, Baby!
    Oh Hell Yeah!
    Halloween is our (we who are in the closet) free day!
    My wife is accepting of my kinkiness when I dress at home. Not so much outside the houseā€¦ EXCEPT on Halloween.
    Woo Hoo! Those of you who are following me on flikr will see some new stuff in a few weeks! (PM me and I will send you a link to my flikr page)
    "My greatest fear is that when I'm dead, no one will remember me"
    Some dead guy

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