The Crossdressers Halloween dilemma. Hm

[2B Natasha]

The Crossdressers Halloween dilemma

So. The day all crossdressers are supposed to be euphoric about is shortly upon us also known as Halloween or all Hallow’s eve if you will. But what to dress up like? That is the issue here.

I came across this conundrum last year and it really has only gotten more confusing as time passes and the day get’s closer.

Do I get dressed up as a Woman and hit it or do I dress up in something different?

Let’s look at from two angles. We will call are subject Bob and Joe.

First we have Bob. Bob likes to get his girlie on and go out. DOes it when he wants and where he wants. He’s been out numerous times and just goes out and has a good time. Bob looks well put together. Dresses to blend into whatever situation his in. Has a fairly extensive wardrobe and takes pride in his appearance and feels great about himself.

Joe on the other hand. He is, what we will call, a closet crossdresser. He only dresses at home and is not wanting to let anybody know about what he does alone at home. The neighbor can’t see him and especially his work can’t see him dressed up. What we he do? How would he explain it? He really has no solid evidence that anybody would do anything, just his own personal paranoia.
SO. Joe is invited to a party. It’s a friends house party. There are sure to be a fair number of guest’s there and he is assured, by the party givers, that EVERYONE, will be in costume. Heck. Even the husband is getting dressed up like a women and she is wearing a tux, for a little roll reversal for the night.
So does Joe get his girlie on and go? It is Halloween and it’s a costume party and the thrower is going to be dressed like a women.
But is that the best idea for him? Yes? No?

Let’s look at it. Normally when a Non-crossdressing male does a female impersonation. What do they look like. Flip flops for foot wear as they don’t have shoes that fit. Rolled up sweat pants under an ill fitting dress. Boob’s that are lopsided because they are sock’s rolled up and a bra that doesn’t fit well. Hairy legs. A cheap used wig that is a bit ratty. And if there is make-up, it is slap dash.
But our man Joe has been dressing in private for years. He has a nice wig that he knows how to style. His underwear is the perfect fit and matching. He has a a drawer full of stocking to attach to those garters he loves so much. His closet is full of clothes that are all color coordinated and fit perfect. His shoes and purse match. His accessories are understated but compliment hit outfit and his make-up is flawless after so many years of doing it all be it alone.

Does he do it up? or not? If joe show’s up looking perfect and has the look and mannerism’s down pat. He looks like a woman. acts like a woman. Does he not run the risk of SOMEBODY asking the question and starting the rumor mill that he looks a LITTLE to perfect for this being a thrown together outfit. If he dumb’s it down how disappointed will he be? that this is not how he imagined it at all.

Where as for our man Bob. You remember Bob. He going as spiderman. He can dress up like a woman anytime he wants to. But really. How many days do you get to dress like spiderman?

So my question is. What does Joe do? What will you do?

Me. I’m with Bob.

[DebbieL]

I've found that I get lots of requests for dances and even phone numbers and dates when I dress up as a Maid. I suspect there are a LOT of women who would love to have a boyfriend or husband who would dress up like a maid and actually do some real cleaning, even some cooking and sewing. If you really want to impress, make your own alterations to the costume, or make the costume yourself. IT will make a huge impression.

I've also had good results when I've gone as a dominatrix, complete with hip high boots with spike heels, corset, leather skirt, and collar around my neck, not to mention leather handcuffs as bracelets. Some girls will actually bend over the table for a spanking, as will some men. Others will want to turn the tables and take the crop to me - those were the ones who got me VERY interested!

Halloween is a chance to let your true self come out. As such, it's generally NOT a good idea to come as a mere hooker.

Even if you are married, going out as a maid, domme, or vampiress is more likely to get HER more compliments from envious women.

And whatever you do, really play out the role. Have a real cleaning rag and offer to shine shoes (Maid), or have a riding crop or paddle and use it (Dominatrix), or give others a gentle nibble on the neck instead of a kiss or hug (Vampira).
.

[Beverley Sims]

I make up as a very convincing princess with a low cut top showing my ample cleavage.
This does confuse the hell out of the doubters.
Plenty of perfume and everyone gets an eyefull and a good sniff.

[kimdl93]

Neither applies to me. I quit drinking on New Years Eve a long time ago - kinda consider it amatuer night. But I've never made it a practice of getting in costume of any kind, nor going out dressed on Halloween, mostly because its usually a work night. I do turn into a pumpkin around 8:30 every night, if that counts.

[rachaelsloane]

I'm with Bob on this one. It's the pleasure of going out dressed for an evening of fun.
" Wine is sunlight, held together by water " Galileo Gallilei/A line I can relate to.

[ChelseaErtel]

Love this thread, thanks. Now, I don't get excited about Halloween, but your question is a good one and got me thinking.

Now, I have not told my wife - yet. Working on that.

So, if I was given the opportunity to go to a party, I would dress to the nines and be as perfect as I could be. I'm known as an artist so it wouldn't shock anyone I don't think. If the began suspecting, then good as they are correct. I'd thank them for any comments, but not let on it's a normal thing. It's almost a "wanting to get caught" think for me right now. I'm almost there in telling my family, but I still need time and professional help.

So for Joe, it depends. Does he really, subconsciously want to come out? Then dress to the nines. Or does her really want to keep it private? If so, then go as a gorilla or something other than a woman.

[Chickhe]

You can do it any way you want. The key, I think, is to park your feelings for the night and just do as awsome costume. Explain nothing, just joke around and have fun and make sure everyone else has fun. Then you can spill the heavy stuff some other day when people have already seen you. I tend to get better reactions when I go for convincing woman wearing a costume... depends on what you can pull off, but it works almost best if the goal is not to be a woman for the night... think of it as you are already a woman and what you want is the best costume she can wear. If you look good, I think people can see the effort you put in and they respect that. No one will question your manhood...they may joke about it, but no one actually thinks much of it. Its all in fun on halloween. Throwing work in the mix can be tricky, sometimes very bland and boring in the best costume to show your co-workers.

[tifftg]

I think for Joe the question he has to prepare for is how does he look so good and does he want to hide it again in the future or does he want to start opening the door wider. If it is believable that he really likes going all out for costumes and enlisted someone to help with makeup, do it and enjoy the evening. You may want to occasionally adjust the shape wear or complain about the heels but revel in the feeling.

[2B Natasha]

Hey. Thanks for the responses so far.

But a point of clarification if I might. I am not Joe. If I'm anything it's much more Bob like. For me. Halloween is a chance to go all out I LOVE LOVE LOVE super over the top costumes. I can get my girlie on any time and go out. That is not an issue.

The question is just that. A question. What do the Joes of the world do? They must be quite torn inside about it.

Cheers.

[STACY B]

I see where ya coming from ,,For the simple fact IF ,,,,,,, There was another Closet CD or Atleast Observant GG there they would pick up on it Cuz you an I well know how much time an energy it takes to put all this together ? You can't just run out an get an outfit an all the trimmings just like that ? It takes way more time an effert than that . So I would be wary of being found out if you don't wan't to be !!

[tiffanyjo89]

If "Joe" is known for being a perfectionist, then yeah, Joe should show up "perfect."

Heck, there are people who cosplay and go into such extreme obsessions (actually, normal to them, but to an outsider, extreme) on making their costume as close as possible to the character they are portraying. Joe's a closet CDr, so he, to others, is portraying a character.

[Stephanie47]

I think if the host and hostess of the party are going to role reverse, then the choice is easy. If I was Josephine I would go dressed to the nines. Now I would make sure there was a little fun involved. I would not just go in a womanly everyday outfit. I would go wearing a floor length red evening gown/prom dress with red shoes. I would throw in a crown and scepter. I would even make up some sash to wear, "Miss ______." Fill in the blank! Something naughty! :)

[JamieRohr]

I was exactly like Joe when i first went out i think 2 halloweens ago. Super paranoid what everyone might think, but knowing that I wouldn't have another opportunity like this again, I decided to go all out. A friend even help do my makeup and get ready. Needless to say, it was well worth it and would do it again in a heartbeat. How I was able to be the girl i wanted to be... well it kind of went like this: Made up a story that this girl I liked and I were gonna dress up as opposite genders, but then she bailed. So, instead of "wasting" my nice outfit and all the makeup that was already done, I told my friends that I would go with them instead to our other friend's house party. No questions were asked! Best memory ever.

- edit

Just to add: when friends asked where i got my clothes, wig, accessories: simple, friend that's an aspiring actress let me borrow it. lol

[I Am Paula]

If you are not usually out in the real world, go glam, give it everything you've got. Yes, cleavage freaks 'em out. Go to a straight bars' party. You might win a prize. Don't over think the 'will they know?' part. Have fun.
If you're out in the RW everyday anyway, I think a costume might be fun. So it isn't like going to work on your day off.hugs- Celeste

[Being Paige]

I have to agree as I'm more of a Bob and get girly anytime, Halloween is not a dress up outing for me. If I were to get a costume and go out maybe it would be Bat Girl and Wonder Woman. LOL

[Jenniferathome]

I had a conversation with my wife last night on this very concept! I'll offer her assessment. A crossdresser dresses on Halloween because he thinks no one will say anything. However, if the "costume" is simply that a of a well put together woman, then it is certain that everyone will suspect there is more going on than Halloween. So the option is, over the top crossdressing: Monty Python style woman (hideous) or questions being asked or thought. She even said that a drag queen would be too questionable. As you pointed out, why would you have shoes and a wig and clothes that fit?

Halloweener beware!

[linda allen]

Life is not as simple as the "Joe and Bob" choices presented. Those are fine as far as they go and the observation about the non-crossdresser's poor imitation of a woman are pretty accurate. If you are "in the closet", so to speak, and go to a bar or party with friends or co-workers and do too good a job of dressing, you will arouse suspicion at the least that this is more than a Halloween costume.

On the other hand, if you seldom or never get to go out in public as a female, Halloween can be your cover as long as you don't go around friends or co-workers. Walk in the park, downtown, the mall, Walmart, etc. and if you pass, nobody will notice you, mision accomplished. If anyone clocks you, their guess will be that it's a costume and you're headed for a party.

[BRANDYJ]

Good topic OP. My take on it is a little different. I am not like Bob and I'm not like Joe either. I have gone out to events and places where alternate lifestyles are accepted and expected. So that sets me apart from Joe. But also, I don't go out in public shopping or socializing in straight bars etc. So I'm that third guy. Call him Jim. If I wanted to go to this fictitious party hosted by a friend that I knew was going to dress and roll reverse with his wife, that alone would ease my mind and I'd feel very comfortable in going dressed fem. However, to throw off those that would think I do this all the time, I'd go as a very genuine nurse from the 50's or 60's. In the first place, I love the all white dress, hose, white cap and shoes that our nurses used to wear. So yes, I may look even passable, but in a uniform like that everyone would know it's my costume.
I actually dressed this way one Halloween and had a ball. A GG was there dressed in one of the cheap commercial nurse's costumes that are on the market. She came over to me and said I made a better looking nurse then her and that I deserved the the nurse's cap more then she. Since I did not have one, she gave it to me! OK, I admit this was a nigthclub that caters to alternate lifestyles, so pretty much anything goes. But if this was a part held by a friend and he and his wife invited mutual friends and maybe even some of my co-workers, I's still wear that nurses uniform and try to be as genuine looking as can be. If anyone asked, I could always say it was my SO's idea and she put the outfit together and helped with the wig and makeup. If they don't buy that, it's OK and they still would be left just wondering with no facts as to what I do or don't do on my own time.

[Desiree2bababe]

I guess I was Bob the first time I went out dressed as Desiree with my wife (then girlfriend). She kept repeating how feminine I was in my gestures, such as holding a cigarette, walking (how good I was in heels) and what a bit of a tart I was for not wearing a slip under my see thru red dress. She flaggasted me when she suggested we go find some men. I believe she was feeling me out on just how far Desiree goes. I wish I'd taken her up on the idea.........

[~Joanne~]

As you pointed out, why would you have shoes and a wig and clothes that fit?

Halloweener beware!

well there could be excuses for this too or even that you went and bought some cheap stuff to make sure you weren't uncomfortable all night. Then there is the borrowed.

Me, I am with Joe this halloween. I wondering what she is doing? lol I want the experience of being out for an afternoon/night for a day and plan on going into another county to get it. I have all these heels, skirts, dresses, and so on that may never see the light of day until this time next year so I will not waste it, over think it, or care what anyone thinks amongst people I don't know and will never see again :)

[Sarah Doepner]

I've thought about this before as well and still don't have a good answer. I dressed as a nurse several years ago and used a little daylight on that weekend to just go out in normal female clothing but with a bit of a halloween touch to them. It's still the talk of the family, so I know I made an impression, just not sure what that impression was. Since my wife isn't ready to share my crossdressing with the family I haven't done a female costume on Halloween since, at least around those who saw me the first time.

As much fun as the nurse outfit was, I enjoyed the day trip much more. This year there are too many things interfering with my world so there will be no femme time for another couple of weeks. I still get to dress at support group meetings and get a visit or two to Las Vegas where I can do it up properly, so I'm not struggling too much with this issue for now. It will roll around again and maybe next year I'll solve this quandry.

[docrobbysherry]

It's really quite simple. If u don't wish to be "made", don't dress up as simply a woman. If u look too good, folks will wonder!:eek:

Dress up in a female costume! You're supposed to look convincing in any costume. How else to win the contest?:daydreaming:

And, for those that at r out. It really doesn't matter does it?:straightface:

[franlee]

I think all the worrying is unwarrented, who cares it's halloween. Sure everyones going to chit-chat the next few days and then it's on to business as usual. Don't let your parinoia cost you some of the best times of your life. Besides people are going to speculate and gossip about something regardless.