how much mileage can I get out of Halloween?

Approximately 10 years ago, I dressed up as a trashy prosititute, and my GF was "Lenny" the gold-toothed, cucumber-packing pimp. I thought our costumes were well thought out and very detailed. I'll spare you the commentary, but we both looked good.

Even though my feet were killing me by the end of the night, I had an obscene amount of fun. It was the first and only night that any of my friends or family had EVER seen me in femme mode- which probably helps to explain why it was so much fun. Anyway...

Everyone says that Halloween is like a free pass for CD'ers. And I want to go out again as a female, either as Alice in Wonderland or Dorothy from Wizard of Oz. But for a closeted CD'er- what happens when I go out a second time as a female? Seems like it wouldn't be hard for friends and family to put 2+2 together. They will certainly wonder whether they say anything or not. I know many of you will tell me I shouldn't care, but I feel like I already spent my free pass. What say you?

It was 10 years ago. Not last weekend. I think enough time has passed. I doubt any will point at you and scream "Crossdresser!"

Do you have a female confidante (girlfriend or platonic) that will play along and be the Mad Hatter to your Alice... or the Scarecrow to your Dorothy?

How about heading out of town away for a big Halloween street fair or night club event? Go where no one knows you and you can be as girly as you like.

Jesus,,, Not many people I know can rememeber back a year much less 10 ,,,You worry to much,,Just go an have FUNN!!

Are you flying or driving? Oh, thats not what you meant!! LaLaChic was right, it was 10 years ago! It is your life, so do what you want to do. If you can get a GF to play the other part, even better!! Have fun!!

I say go for it! Seriously! I can't remember what I was doing last week, let alone 10 years ago... But then, I do have kids, so that might explain some of the shorted-out circuitry.

It was 10 years ago and nobody will give a poo. Just think of it as a Batman costume that you wear year after year.
I know I'm going to be dressed as a girl for the rest of my life on every Halloween weekend until I stop sucking air. And mileage you say, well hey I was thinking the same thing but I'm talking real miles here!!!!!!! You see Halloween falls on a Wednesday this year, so is it possible to go out on Friday and Saturday night dressed up before Halloween day? Then I could dress up on the Wednesday and the following weekend after dress up on Friday and Saturday all over again and tell everybody that I had to go to a lot of different parties on the weekends? Thats the kind of mileage I've been thinking about.
I will need Stacy B's opinion on this one.......

The word your looking for is BELATED ,,,That's what it is when a Holiday falls on a weekday ,,That's my girl ,,Don't miss a thing . Use it up an wear it out ,,,, WOOP'S Halloween Party on the weekend after ,,, OHHHHHHHHHHHH YEA,,,,, Last bash of the year !!!

Lots and lots, but I would not do it too good. Halloween is more for "costume" than CDing. Free pass? I would say still there. Enjoy!

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Originally Posted by Abbygirl

Approximately 10 years ago, I dressed up ............ Seems like it wouldn't be hard for friends and family to put 2+2 together. ................... What say you?

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I say don't go around friends and family this time. Go by yourself or with different friends or family.

I posted this on another thread, but the problem with crossdressers going out on halloween dressed as females is, most of us do too good a job of it. A "normal" (for the sake of this discussion) male will throw on an ill fitting bra, stuff it with socks, put on a cheap wig and dress and a pait of 6" heels that he can't walk in and it's pretty obvious this is a costume.

A crossdresser will probably have decent breast forms and bra, a nice wig, proper makeup, and proper, well fitting clothes and shoes. And he (she) will be comfortable and natural acting in this outfit.

So - you will "out" yourself regardless. Go somewhere where nobody knows you and have a good time dressed as you please.

Abby, Go for it! My Wife and i have went to 5 street parties, and the neighbors all look forward to what the crossdresser is wearing this year. Also came out to Wife when i said We should "practice" makeup. for Halloween in March. Luv Roberta

I went to a big fancy dress party with my SO just over ten years ago, it was the first and only outing where I was properly femme around close friends. It was as you can imagine one of my favourite memories ever. Although I wasn't anywhere near as experienced as I am now, cheap wig etc. I was young and convincing enough that I fooled many (I'm not kidding myself I passed it was fancy dress so everyone looked unrecognisable). However problem was that I still did it too well that close friends once in a blue moon remember it, so in my case my 'free' pass has gone :(
I know it was ten years ago but if it's close friends and family it's highly likely they will remember, as you would have made an impact on them, people don't usually forget that kind of thing. So it comes down to what will you say if they do remember and start asking the questions. Are you still with the same GF? If so you could get her to say it was all her idea as she loved the last time you did it, maybe don't look too good.

One day I will get an invite for a fancy dress party with a topsy turvy theme. Problem is all other men normally look comical, we can't help ourselves and make too much of an effort, thats ok but if someone you really don't want knowing sees this more than once they will start to wonder.

As someone else said can't you go out of town or somewhere those who saw you before will not be?

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Originally Posted by linda allen

I posted this on another thread, but the problem with crossdressers going out on halloween dressed as females is, most of us do too good a job of it. A "normal" (for the sake of this discussion) male will throw on an ill fitting bra, stuff it with socks, put on a cheap wig and dress and a pait of 6" heels that he can't walk in and it's pretty obvious this is a costume.

A crossdresser will probably have decent breast forms and bra, a nice wig, proper makeup, and proper, well fitting clothes and shoes. And he (she) will be comfortable and natural acting in this outfit.

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I agree with Linda. Putting it together right is a dead giveaway. Especially around family and friends.

If your going quite a few towns away and just driving around or going into stores or a party at a bar/club then go for it and enjoy it. As for "mileage" I thought you meant how many days could you pull this off, that would be 3 days before, on, and maybe even a day after Halloween depending on what day it falls on.

his year it falls dead in the middle of the week. so that whole week may be good as people could possibly have a late halloween party on the weekend.

I agree with everyone else, go out and have fun!!! We closet girls only get a "Pass," once a year at Halloween, so make the most of it while you can!!

I've been going out for the past 18 years in one outfit or another. Always in womens clothes. It's my way of coming out. If someone asks I tell them I dress like this all the time. Now only I know It's not a joke. It's also a way to see what reaction you will get from your friends and if they would accept you.

I think the statute of limitations has probably expired in 10 years. But is there something besides Alice or Dorothy available for you? How about doing the most totally convincing presentation of a woman that you can, and see if anyone actually can put 2+2 together.

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Originally Posted by Abbygirl

what happens when I go out a second time as a female? Seems like it wouldn't be hard for friends and family to put 2+2 together.

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My experience was that it did not take a second time for friends and family to put 2 + 2 together.

But, in my case it turned out ok as any mention seemed to be all-in-good-fun. I still go out every Halloween and for sure, any strangers you meet will give you a pass. I usually go to a town nearby to minimize repeat sightings by friends and family though.

I did exactly that! Did it a few times decades ago and had a blast. Then recently, over the last 5+ years I've been doing exclusively female costumes (its almost becoming a tradition now). Its usually just my wife and I who go out, but still it is a lot of fun. We're getting too old to enjoy drinking much and we just like dancing and seeing other great costumes. I've been getting more and more sophisticated or polished in my attempts...going for appearing to be a female in a costume and had some success and I'm worried less and less what other people think...the way I dress does not dictate who I am... it is just a costume. My wife seems to enjoy it and the last two times we even had to fend off guys who wanted to chat us up! I had the same fears as you when I decided to do female costumes and the fear was for nothing... anyone I've talked with, guys or girls are very impressed...mostly the girls stay and chat for long time asking about how I did everything...the guys joke around and just be prepared to joke back a little to show them you're friendly. The largest mistake you could make is taking yourself too seriously. I say do it... it will add some spice to your relationship...keep it fun and you won't be disapointed.

I agree with Becky. Some close family and friends will remember the minute detail of what you were wearing. And, if they did, then I suspect suspicions may arise. I've never had the opportunity to go to a Halloween Party. Having kids kind of gets you stuck at home distributing candy. :(

I always look at the calendar and have hunger cross dressing pangs when I see Halloween is on a Sunday. Parties seem to run Friday, Saturday and Sunday on those weekends. Three days of cross dressing bliss. When I was young I would be passable. Now. Well, the Wicked Queen maybe!

I always thought I would dress as an attractive woman in ordinary/non costume attire. King of what I am wearing right now. Before I retired I listened in to a conversation my supervisor was having. She had dressed up her husband, who is the same height, in one of her high school prom dresses and a wig. I was green with envy. The women in the conversation were actually interested in how he looked, etc.

I think a lot of women with non cross dressing boyfriends and husbands secretly would love to try to dress up their man. Women seem to be more accepting of gays and lesbians and an occasional Halloween outing with a 'female' husband would be a gas.

Once my wife and I ran into her father dressed at Halloween as a woman. He did not look good, but, he and his female friend had a blast. My DADT wife does not remember that at all. For me, it has been engrained in my head. The best I ever did on Halloween was to get dressed and twice go out for a drive fully en femme, makeup and all. I went into a Safeway and a Winchell's doughnut shop. I did that after the wife and kids were in bed. No, I suspect my wife really did know I went out. It would have been nice to have her go along.

Wow, thanks for everyone's reply! Seems like a lot of you girls are saying "it was 10 years ago, you have no problem"...but I still feel like I've used up my "family and friends" free pass- they might forget a cowboy costume or a goblin costume or something, but a 5lutted-out hooker in a leather micro, stiletto heels, and a feather boa? One time out as a female and it just looks quirky and fun. The second time it begins to look like a TREND.

I think I will do as was suggested, and just not let the family see me this time. The great part is I still have the same sweet girlfriend, and she would play along and have fun doing it. (I know for a fact what she really wants to do is a "Sonny and Cher" combo. I'll let you guess who is Sonny and who is Cher.)

As far as "doing it too well"- it's like this- IF I do it, I'm doing it right. The whole idea is to use the holiday to let my normally closeted expressions out! I just have to decide to either DO it or NOT do it. I agree that a super-polished presentation might make me look a little too comfortable, but I still think the fact that I would wear a female costume more than once is more incriminating.

You can't go too far wrong with this era of Sonny & Cher:

http://img2.timeinc.net/ew/dynamic/i...y-cher_240.jpg

I agree, when I go out I want my costume to be as "good" and complete as possible. I will not purposely mess something up to superficially reduce the chance of being clocked as a CD/TV. But I do wear a costume, not street clothes that I might wear to a support meeting or out to dinner.

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Originally Posted by kimdl93

........................... How about doing the most totally convincing presentation of a woman that you can, and see if anyone actually can put 2+2 together.

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Yes. If people don't "clock" you, you've pulled it off. If they do, well, it's Halloween so it's OK, you're in a costume for a party or event. You win either way.

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Originally Posted by Abbygirl

I think I will do as was suggested, and just not let the family see me this time.
As far as "doing it too well"- it's like this- IF I do it, I'm doing it right.

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Sounds like a plan :)
I would want to look my best too.

Got ONE question for you. Do you NEED to show your face? Or want to?

There IS a reason that dozens and dozens of "generic" masks of all varieties, sizes and colors are sold. Of all the multiple THOUSANDS of Halloween FEMALES I have seen over the years [at Guavaween alone you can see several thousand easily in one hour of walking] less than 20% won't be wearing SOME kind of mask regardless of their outfit.

Problem solved I hope.

Will any of the attendees from that party be at this one? I doubt anyone will draw that conclusion unless you have skipped dressing up all those other years. I would go for a real life female but that is just me. If you have a GF that is game to be your male counter part that helps. Also, years ago i CDed for halloween about 6 years in a row and just played off the comments.

If somebody does REMEMBER, tell them that as it was so successful last time you thought you should try it again.
After doing it 10 times in a row, the comment might be, "I wonder what kinda chick Bob will come as this time?" ;)

Here's an excuse for you:

Other person - "Why do you dress up as a woman every halloween?"

You - "I like to play with boobs and this is the only way I can do it and not get slapped!" :heehee:

Sara, I think you've hit on an important point that I failed to mention - I have not dressed up as anything since the hooker night. Which will tend to strengthen people's curiosity. Oh well. If we can find a party I will probably do it anyway - no one is going to disown me, they probably wouldn't even say anything about it if they did suspect.

Also, if I'm not related to them, work with them, or friends with them, I don't care at all what people think of my girly Halloween costume. But I do think it will increase friend's and family's scrutiny of girly things I present with every day that they may not have thought about before. Ya know what I mean?

How much mileage can you get out of Halloween? A lot, if you have a Nimbus 2000.

I would dress however you want for Halloween. The best thing that could happen is that someone mentions that you dressed 10 years ago. Then you can reply, "I had a blast then and I am having a blast tonight!"

I also use Halloween to push the edge every year. It seems to be the free pass. Have fun!

UPDATE: I'm going for it! This year I'll be making my second official Halloween appearance as a female. Let 'em think whatever they want to think, it's my party!

I'm going to be Morticia Addams, my GF is going as her husband Gomez Addams (from the 60's TV show The Addams Family for those not in the know)

I found a wonderful lady on etsy.com that is making a custom dress to my measurements. It will look like the hobble dress from the original TV show, in stretch panne velvet, black of course. It will be form-fitting all over except for the flare below the calves. Here's a sketch she did. The V-neck will be more narrow and much deeper, other than that this is what it should look like:
http://i1173.photobucket.com/albums/...etch_small.jpg

I just finished making my foam hip/butt pads this morning. Morticia's measurements will be 45/36/47. That's quite a bit larger than Carolyn Jones (actress who played Morticia)was on the show, but at least I'll have the hourglass like she did. It's a costume so I think a little exaggeration won't hurt. Plus it's fun to have a big ole butt wagging behind me!

I'm so excited! Can't wait for Halloween! Just gotta practice shuffling around with my knees tied together...

>>>>>>>>>>>>practice shuffling around with my knees tied together... <<<<<<<<<<<<<<
haines smooth silky suport panty hose , well fitting open bottom girdle
another as small or smaller open bottom girdle upside down with the garters hooked together, now that your properly hobbled and girdled go practice!
She in her dress looked to be a mobile form of bondage , she could not have dressed undressed her self!
the bottom of her dress were her roots! they were stiff and skitered across the floor.

Have always loved the Adams Family. I even met John Aston once so I would love to see a picture of you and Gomez.

i bet that will be a wonderful costume and custom fit too you are one lucky girl

Congrats on going for it! Keep us posted!

you go girl. enjoy the experience of being who you are while everyone thinks you are pretending. its the perfect plan and i salute you. dying to hear how you get on

I don't think twice in 10 years would come across as a behavioural trend! Go for it girl! ;)

I was thinking of using Halloween to go out in a skirt or dress for the first time. I have the next day off for medical tests and could stay out late. I am worried about going to a bar as I am a recovering alcohalic. Some friends from my support group will be there but they have their own friends and are a younger crowd. Oh well I will buy a dress anyhow and worry about it latter.

hugs rita

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Originally Posted by rita63

I was thinking of using Halloween to go out in a skirt or dress for the first time. I have the next day off for medical tests and could stay out late. I am worried about going to a bar as I am a recovering alcohalic. Some friends from my support group will be there but they have their own friends and are a younger crowd. Oh well I will buy a dress anyhow and worry about it latter.

hugs rita

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I say do it! Go get the dress, a few things, but perhaps go to another place/bar and order a few cokes or something. Make sure you take a walk around several blocks. RELAX and enjoy yourself and if you fell really good keep walking the blocks...no worry at all...its halloween! You do not have to pass on Halloween...or any day matter of fact! Being the girl that night is far more important than a drink! Keep that in mind and I think you can stay away from the drink.