Did Halloween really count as "out" in public?

We all know that Halloween is pretty much a crossdresser's dream holiday, and it probably takes less balls (pardon the analogy, but the irony was too much to pass up) to go out for the first time on Halloween weekend than other times of the year, but that was when I first worked up the nerve to go out in public dressed up, just this past year.

I have dressed in private much of my life, going through the typical hid it, purge, don't tell girlfriends, lifelong game of denial until my current relationship when I just went with it and told her a couple years ago. I got lucky and have a supportive significant other (SO) who didn't run away in horror and actually doesn't really mind. I can't say she prods me to dress, but really has no problem with it and helps me get ready for nights (or days when the work schedule allows) at home dressed up. Helping with makeup, clothing, nails, etc is something she is more than willing to do and it is really pretty cool to have a supportive SO who thinks it is fun to have a little dress up project sometimes. A bottle wine (or more) definitely helps us get into it more sometimes. But dressing at home wasn't enough for me, as it isn't for most of us. I yearned to try out in public.

So, we did this past year Halloween. Actually, the day before Halloween, but on a Friday night of a Halloween weekend why not, right?

I have gone through the typical try to find the right size game when buying clothing online and it really is a bit wasteful to end up with the wrong cloths and either return them, or in many cases I just haven't bothered to return them and they just ended up in the donate pile.

So, I had it in my mind that I wanted to go shopping. For real. Dressed as a girl.

I live in a very conservative part of the country, where seeing someone crossdressed is very rare. So, I was obviously nervous, but what the hell. Go with it I guess is what I said in the end.

I got home from work early on the Friday and we set to getting me "ready".

A shower with a very close shave. Some facial moisturizing. And it was time to start with the rest of the process.

I didn't hold back. Thigh high black stockings and knee high platform heel boots. Panties, a bra filled with some good breast forms I have, and a dress that went just below my knees. I topped it off with a good wig that I had bought for the occasion (shoulder length to try to cover more of my manly features).

My girlfriend did my makeup, glue on nails which she then painted, and completed the look with some of her jewelry (a necklace and bracelets - I didn't have any rings and don't have pierced ears, so those were missing, maybe some clip on earrings in the future need to be added to the wardrobe).

Oh, and I had to add some perfume. To me for some reason the perfume is one of the major finishing touches in my mind when dressing up. The olfactory stimulation is irresistible to me.

It amazed me how long it really takes to get ready. Nearly 2 hours. Serious respect building for women who do this stuff every day.

To help take the pressure off, my girlfriend also dressed up in a sexy Halloween style outfit and we were set to go out.

The plan was to go to Lane Bryant for some shopping (to buy a couple new outfits) - I am a bigger guy and needed to go to a plus size women's store - then to go out for some dinner, "in costume" for the holiday.

The store was about an hour away so we left the house with me fully dressed up committed to no getting out of the game until we went home.
Driving in high heeled knee high boots was another new experience.

I guess once I was in the car driving I can honestly say that the nervousness went down a little. I don't know if it was because I knew I was committed at that point and just went with it? If it was because we had developed a little "story" for the event whereas we had developed a scenario that I was going out dressed up on a Friday night as a gurl because I had lost a bet with my girlfriend and had committed to spending a weekend dressed as a girl (that I had agreed to do it on Halloween weekend to lessen the potential impact of being in public dressed up, that the other option I had in the bet was way worse and I would easily have chosen this option, and that no permanent body changes could be made - think shaving legs, piercing ears, etc)? Or if I just hoped that because it was Halloween I would blend in and nobody would care. Although with the obvious caveat that nobody really goes shopping for clothes dressed up obviously. Whatever it was, I went with it.

We went into Lane Bryant (and I will add we only went an hour or so before closing to limit the traffic that they would be experiencing) and I just went with it. Walked up and asked a clerk to help. Told her I had lost a bet and was going to go with it to make good. I don't know if she thought it was a true story or not, but she was very helpful. I have no doubt that before I told her I wasn't going to "pass" as a woman anyway. There aren't that many 6', 250 lb women around, and I know my facial features and aneurisms (even with makeup etc) don't completely hide the guy underneath. But I don't really care, it feels good to me.

The clerk was awesome.

She got into it and helped find skirts, tops, and some lingerie. She even helped get some discounts. A little under an hour later I had 3 new skirts, 4 new tops, and a nice nightie.
Bag in hand, back to the car we went and off to get dinner out.

We did a dinner at a Bar/Restaurant, thinking on a Halloween weekend there might be others dressed up, but there weren't. Oh well. Nobody questioned, commented, or even seemed to notice me.

Oh, eating wings with long fingernails is definitely harder also. Along with getting my wallet out of the purse my girlfriend had lent me for the night. All the little things you learn as you do this more.

Dinner done, we went home and enjoyed some personal time to complete the evening out.
So that was my first and only time so far out in public dressed up.

I haven't done it again since, but I will admit I have a yearning to go in public dressed up again. I can't really do it where I live because if I was seen, it would have a potential to have professional implications. My work is rather public, and I work in a very conservative industry, and if I showed up anywhere it would spread quickly. So, maybe my girlfriend and I can find a way to travel and have me be dressed up again sometime and go out. Maybe I will just have to wait for next Halloween to do it again.

I know many here have had many more experiences "out" than I have, but that was mine and I thought I would share it! Not sure if Halloween time really counts as "out", but that was all I have ventured for so far. Thanks for the support from everyone in these forums. Another first, this was my first post here.

Halloween counts as out if it was out to you. Congratulations! It keeps getting funner and funner, honest. ;)

Also, just for the record, it's possible to get your prep time down from 2 hours. I can do 20 minutes if I'm in a hurry and focused but prefer to take an hour just to give everything -- including me -- the time it deserves.

Please don't take Halloween away from me, Jenn.:sad:

It's the only time of the year I have any chance of passing!:battingeyelashes:

sure why not right? I think thats a perfect night to get your feet wet it counts ......if you still want to "get out" but cant do it locally why not spend a weekend out of town? Find a friendly place/or event/ bar etc in another town, or another state even, make it a weekend get-away like you said. xoxo

When dressed to pass, everyday is a good day to be out and about. Even in more risque' outfits you can just blend around. So, I look at Halloween as an opportunity to enjoy some extreme adventure. Although I haven't yet, I would love to spend the whole day out in a sexy maid dress or some other costume theme. Maybe this year. I just have to get the wife onboard. sigh!

Great story. Glad things worked out for you.

Jenn - Out in public is out in public. Great story. I am glad you enjoyed the experience. Maybe you could go to the movies during the week dressed. Or attend some CD functions out-of-town. Or drive to a near-by town.

It is if you think it is.Congrats on your first time out dressed!

Did Halloween really count as "out" in public?

Well, it depends. Many men dress as women for Halloween but don't really try to pass and it's a once a year thing or even a once in a lifetime thing. They aren't really crossdressers in the sense that we use the term here. That doesn't count as "out" in public in my mind.

On the other hand, if you do your best to dress, look and act like a woman, that would be "out" in public in my mind.

The danger in this is, if you dress and go where people know you, they might look and think "I'll bet he has done this a time or two before."

Halloween is my night out. I dress up in really girly clothes. Then I simply go to another part of town where none of my friends or family will see me. I have a really large beard so when asked who I am I say that I am the bearded lady. I actually won a contest one halloween for the best costume. Call it what you will but it is my night to be myself completely.

Not quite the same as getting dressed and going to the mall, but you still have to go outside to do it! And if it's your first time leaving the safety of your home, it WILL be exciting. Don't try and convince yourself that it's not a 'real' outing just because it's Halloween. Sure, people may be a little less apprehensive because they're expecting to see some crazy costumes... But for countless others (myself included) Halloween was the first time I ever left my house, and I considered it a very important step.

I've enjoyed being out dressed on Halloween for the last 15 or so years and I do consider it being in the public as I'm always interacting with the other people I meet. But there is one difference on Halloween: the public is much more accepting. They can accept it as a costume when what they don't know is that it really isn't for us. Because it's Halloween they don't need to think any deeper than that. If you tried the same thing on any other night you will get more scrutiny. People who notice will ask themselves "why is that man wearing a dress?" and they won't have the easy--albeit false--answer that it is just a costume. Plenty of people here do it so it is not the end of the world but, having been out on occasions other that Halloween, it just plays out differently and is not as enjoyable for me.

I'd say ANY time out counts. The main thing is that you enjoy yourself, if it wasn't so darned enjoyable we wouldn't bother......or would we? x. :D

I say going out is going out...but, it sure is easier on Halloween even though I was still filled with a great deal of nervousness and excitement.

Any adventure dressed is counted in my book. I haven't been able to go out for several years because I moved to a small town and haven't a place to go without meeting some of my homophobic friends.

If you mean 'out' as in 'out as a crossdresser to others', well, not exactly. What it does is plant in their mind that you like the idea of dressing as a woman, but not that you do it all the time. How you behave while you are dressed will give them a better idea. For example, if you're real good at walking in heels, that confirms that you don't just do this on halloween. Adopting other female body mechanics perfectly also removes some doubt. Perfectly fitting female clothing is another, as most men's initial attempt dressing up usually winds up being not-so-perfect. Make up perfect too? And carrying more to touch it up? There's another. As opposed to, oh, wearing a mop on your head as a substitute for long hair. Unless you're a real actor, going the whole nine yards WILL be a giveaway.

I have friends that know I do like to dress up, but this past Halloween was the first time most of them saw it in person. I'd count it as a coming out for me, especially with as much as I put on to keep the look.

Oh yes, it does count!! That's the only times I have been out. All two of them!!

You need Halloween to get your feet wet.

Once you have mastered that the rest is easier.

How many have made Halloween their first experience.

Where are you now?

Girl Halloween counts.

That's the 1st time i ever went out fully dressed.

Of course it counts - thank you for sharing a wonderful story. You will go out again when it is right for you both.

I do hope it counts as going out in public, because last year it was my first time out at the Jewish equivalent, which is Purim! Purim is a time of dressing up in costumes in Israel, so my SO and I decided Devorah would use it as a "cover." I have been out once since then, but only for a short walk in a park. We are planning another Purim "outing" this year, which is at the end of March, with dinner and a movie.

Any time you walk past that door dressed is out. Don't let anyone tell you different. I am pretty sure they started on Halloween also. Nobody just got dressed one day and ran to the mall. Now that You have had that outing, the "out bug" bites you even more. After last Halloween I have told myself "enough of this halloween crap" and plan on going out when ever I decide I want to go out. Hasn't happened yet but I am sure it will ;)

Yes, indeed it is.

Glad to hear Halloween counts :) I have no doubt I will either make it happen again in a way next year for Halloween, but am looking at other opportunities also that could be made to work. Perhaps a trip somewhere...

OUT enfemme or not?

You decide!

OMG! This was..............

SUCH FUN!!!!!

And VERY VERY COLD! Well my arms and legs and feet and exposed chest were cold. Everything else, what little there was covered, was warm.

Hi Jenn--Halloween was my first time to go out full dressed as a women. This was 30 plus years ago, and the terms, cross-dressing and transgender, etc. were not in the public domain. Up to this time I had purchased a few female cloths but no complete outfits nor had I even though of dressing up as a woman.
I was out of town helping a friend, at his business. His wife really liked me and was trying to set me up with a girl that she worked with. My friend and his wife were having a big Halloween party that night and his wife insisted that I had to come. I told her that I didn’t have a costume but she insisted that she had just the costume. She wanted to dress me up as “Natasha”. She said that she had everything we needed, a black corset dress, under garments, and the accessories that we would need. My biggest problem was how we were going to hide my beard, because without a wig and proper mask, I felt I would look awful and I didn’t want to look foolish. She said not to worry because she knew a store that sold high quality masks and inexpensive wigs. She took me to the store and we bought an excellent full female face mask and wig. The mask and wig are pretty passable at a distance but easily recognized up close, but it was only for a Halloween party. Early that evening, She dressed me completely, from the inside out as a woman. I ***** panties, stockings, garter belt, stuffed bra, a lacy long sleeved blouse, and the black corset dress, that came with a built in petti-coat. After I put on the dress, she tightened the laces and tied them off, and I realized that I could not get out of the dress without help; I was stuck for the evening. With my mask and wig, I look pretty good, except I didn’t have any woman’s shoes that would fit me, as I wear a size 14. Walking around in that dress, and the way it swished around my stocking covered legs gave me a rush I will never forget. The rest of the evening was a bust as the lady that I was supposed to meet didn’t show, and I only knew the host couple. I ended up drinking too much and woke up the next morning still fully dressed in one of the bedrooms.
When I came down for breakfast my friend and his wife thought it was a scream that I could not get out of the dress without someone untying the laces on the back. She teased me, saying that she wasn’t going to untie the dress and that I would have to wear it home and figure out how to get it untied for myself. Little did she know, I would have worn the dress home just for the rush I got out of wearing it? After a while she did untie the dress, and I got back into my own cloths and returned home. She gave me some of the under garments, the mask and wig to keep. I sometimes wish she had given me that dress. Now 30 years later I still, every once in a while, get fully dressed up as a woman, put on the mask and a wig, to cover the beard that I still have, and go out for a walk, where no one will see me close enough to notice that I am wearing a mask. At a distance I pass as I women, and I still love the feeling of the cloths, and get a little high from the risk of being out.

Out is out!! I don't dress in my city, but I will go out in another city. Don't restrict yourself!!!

When I was younger we didn't have money for a costume. Me and my two cousin's we decided to dress up as women. We even shaved our legs wore stockings skirts the whole nine yards. I think I was the only one that enjoyed being dressed like that. So I myself wouldn't call that coming out cause it only happen that one time.

That sounds like it was a ton of fun Jenn!
I've been out in public en femme a number of times, mostly solo and once with wife, but I've never been out dressed up for Halloween.
I planned on it for last year, but work got in the way.
:)

I think whether dolling up on Halloween counts as an "outing in public" totally depends on the guy. If the guy's wife or girlfriend or maybe just himself decides to "camp it up" and treats wearing women's clothing as a joke, then NO. To see some hairy guy with an unshaven face wearing a ridiculous outfit is nothing more than a joke. There is no intent to be passable or act as a woman.

On the other hand the outing you described would constitute an "outing." If the man is made up to the best of his or his wife/girlfriend's ability to transform him into a woman by shaving of all his masculine hair, applies makeup, dons all the proper undergarments, heels, hosiery and a pretty dress, and, through on a wig that is more than just a joke. Then he and his girlfriend/wife go shopping for more women's clothing, dins at a restaurant, and, let's say attends a movie, that is trying to be 100% woman.

I've gone out on Halloween twice with the intend of mingling with the masses, and, not just taking a stroll in the evening. The first time I wore a midi jade and black print long sleeve dress, black heels and hosiery, all proper undergarments and full makeup and a wig. The second time I wore a sold little black dress with wig and makeup. My intent was to look as womanly/feminine as possible, and, not to treat my "outing" as a camp adventure. I did get some compliments from women I had to interact with. I had stopped at Winchell Doughnut House and Safeway to buy things.

If you feel there would be negative professional implications in your town/city, then make an overnight trip out of it. Halloween is on a Monday this year. I suspect there will be many parties happening the Saturday and Sunday before.

Quote:

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Originally Posted by Stephanie47

There is no intent to be passable or act as a woman.

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I've never considered the above as a requirement to CD in public.

I will adjust my prior answer though. I consider my Halloween crossdressing as being out in the public. But I don't see it as being out to the public.

Halloween was my first and so far only time out. I was Snow White and I had so much fun walking around my neighborhood. The kids were all very nice. I got some dirty looks, but I suppose that's to be expected in the Midwest. I didn't care. I didn't let it bother me. I had the time of my life and was so sad when the night ended.

Sure it does. Its a cross dresser's "perfect storm". It's Halloween after all, your supposed to dress up.

Id also say yes it counts and long as thats what you were aming for someone who dresses up just to make a joke out of it then no but if your serious and put the effort in why not.

Quote:

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Originally Posted by Sweet Jonie

Halloween is my night out. I dress up in really girly clothes. Then I simply go to another part of town where none of my friends or family will see me. I have a really large beard so when asked who I am I say that I am the bearded lady. I actually won a contest one halloween for the best costume. Call it what you will but it is my night to be myself completely.

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OMG im laughing so hard right now good idea to bad I hate beards i'm always clean shaving to the point of baby smooth I hate facial hair but doesn't mean I couldn't by a fake beard or at least grow one just for that day! wouldn't take long I have to shave twice a day I swear my beard grows faster then weeds.

Quote:

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Originally Posted by BillieAnneJean

OUT enfemme or not?

You decide!

OMG! This was..............

SUCH FUN!!!!!

And VERY VERY COLD! Well my arms and legs and feet and exposed chest were cold. Everything else, what little there was covered, was warm.

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You look good around here most of the time id end up with frostbite walking around like that at halloween indoor event or bust for me.

I think it counts. I did it this past Halloween and fooled my sister who hasn't seen me in 3 years and a fellow Coworker who wanted to see me dressed for Halloween. We have a local Haunt called Haunted Overload. I saw my sister in the background of a photo of their behind the scenes so I knew she was going to be there. My coworker was one of the ticket takers.

I walked right past my sister who was directing traffic. She didn't even twig. I turned around and said "What you don't even reconize your own brother?" I got a double wow outta her. One of those softer wows then a real loud WOW.

As for my coworker I just handed her the ticket and didn't say a thing. After she handed my ticket back I said "I am looking for one of my coworkers she is said to be taking tickets." Got a double take and a wow outta her as well. I had fun with the actors there telling them that I was the really scary one as I was a guy. One of the actors just said that's ok come here and give me a kiss! I laughed my butt off.

Never did give him that kiss. :devil:

Here is a pic for you all

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