Thinking Ahead to Halloween Already...

[TrekGirl1701]

It may be a little early to think about this, but it's on my mind now and I want some input.

I'm not out of the closet yet. I'm not even sure I want to be. But since Halloween is an "anything goes" kind of event I was thinking about crossdressing for Halloween this year.

My question to anybody: What kind of costume should I wear? I know some guys crossdress for Halloween, but they over exaggerate the female anatomy so it's more of a joke costume just to get a laugh. I want to genuinely be a female this year, but I'm wondering if I shouldn't wear something that's too girly. Like I said, I'm not out of the closet yet and I don't know if people will wonder about me.

I was thinking of wearing a real authentic cheerleading uniform. But I'm afraid it may be too much for my friends and family to handle. I'm not the type of person to wear any "outrageous" costume. Some people are "out there" and others expect it from them, but I'm not one to shock.

Any input would be great! Thanks in advance!

[Jess_cd32]

Being a member here during this past Halloween this was discussed to some degree. It seems the concensus is that if you look to good, and I mean having most of it all down pat that others will 'wonder' how you pulled that off without some practice. Something to think about.

I know how you feel, you want to look great and not go out as a joke, maybe go out looking good, but not to good??? At least you have plenty of time to think about it.

[MarinaTwelve200]

I think it is a good idea to do a female COSTUME rather than simply "a woman". My first and only time out Dressed was a couple years ago, at our adult sunday school's class's Halloween party as a "gypsy fortune teller"

It was great, I could go "over the top" with the exotic makeup, jewells, etc. I even carried a crystal ball and tarrot cards. The "Gypsy" aspect of the disguise sorta overwhelmed the TG aspects of it for both me and the other party goers.----Some disguises will do that A "cheerleader" might be that way too (I dont know) its an aspect to concider.

Needless to say I was the hit of the party, (and ALL the ladies) everyone wanted me to "read their fortunes".----I got first place BTW.---A great if not a bit drastic way to meet the girls---btw

[Gabrielle Hermosa]

I read on another website that dressing up in a female costume for Halloween can be risky for the reasons Jess brought up. I forgot what website it was - wish I could have linked to it.

It was suggested that if you choose to dress up female, it might be wise to go with a female oriented costume rather than just go as female, period. It sounds like you're already thinking along those lines with a cheerleader costume in mind.

It might help if you could hook up with a girl friend who might be interested in going out with you dressed up like a football player or something. If you could incorporate an aspect of flipped sides, you're less likely to get questioned about why you chose a female costume. This might also allow you the opportunity to really perfect your cheerleader look without anyone suspecting more.

If you're in it solo, it may be in your best interest to exaggerate your makeup to some extent rather than try to be realistic. I don't think you need to exaggerate other elements (such as overly large pom-poms ) but exaggerated makeup should help mask the fact that you're in to this kind of thing as more than a Halloween costume choice.

Maybe you'll get lucky and find some girls who have a hard time taking their eyes off you as a cheerleader. You might end up opening up a few doors you didn't even expect to.

I'd love to do a female costume for Halloween this year, but I'm pretty sure I'll chicken out. Even on Halloween, I worry about what people around here might think and if it could lead to trouble for me. I really do need to work on that!

[LisaElizabeth]

My wife and I started last March talking about Halloween. I have been interested in going as a Medieval couple for a few years and she agreed this year!!
Had a lot of fun putting the costumes together. Oh!! It did cost about 50% more than I thought it would but it was worth it!
http://www.lorianncostumedesigns.com
I haven't figured how to load the pic from my computer, but on the 'Customer Picture 2008' page, the upper right 2 pictures are me and my handsome 'Bard' at the halloween party!
It was a lot of fun and I would use the outfit again, only this time I am going to lose about 50 pounds first!!
Lisa E

[Jenna Stunned]

2 halloweens ago was my coming out. I went dresed to my girlfriends parents halloween party. My girlfriend had a french maid costume kicking around in the closet. Which i wore in secret from time to time. Well anway, I told her last minute, after a few beers, That i wanted to dress up for halloween this year and was thinking of crossdressing. She thought it would be funny and said to go for it. I asked if i could wear the maids costume and she said i could have it.

I was SOOOOOOO tempted to shave my face and legs, and my gf said to go for it, But i didnt want to go too over the top for fear of suspicion. The costume didnt look right with my bare hairly legs so i got some black thigh high nylons and a garter. Had my gf put some eyeliner, mascare, eye shadow, and lip gloss and i was all set.

Over all the costume looked good. I was a very pretty man in a sexy french maid costume. Im glad i didnt shave my legs for the party. It would have been to much. Im kinda of a nut anyway so the people at the party who knew me didnt think twice. Everyone else im sure were a bit suspicious. All night i had a blast and was really happy i went out dressed. It felt SOOOO liberating.


The moral of my story is that halloween is a perfect time to wear something outrageous. But, depending on who is going to be seeing you, You might not want to go too over the top. What you should wear depends on where are you planning on going for halloween and with whom??

[TrekGirl1701]

Thanks for the replies, everybody!

Sounds like most everybody's in agreement then.

It was suggested that if you choose to dress up female, it might be wise to go with a female oriented costume rather than just go as female, period.

Oh, yeah, definitely. Besides going in a costume is more fun anyway.

It might help if you could hook up with a girl friend who might be interested in going out with you dressed up like a football player or something. If you could incorporate an aspect of flipped sides, you're less likely to get questioned about why you chose a female costume.

This is a good idea. Last year at the party I went to, two guys and a girl went as Jack, Janet and Chrissy from "Three's Company", but the two guys were the women and the girl was Jack. It got a big laugh from everybody.

What you should wear depends on where are you planning on going for halloween and with whom??

I'll definitely be attending a party thrown by my brother and sister-in-law, so family will be there. Plus their friends, whom I'm familiar with, too.

It's a tricky situation, but I do have plenty of time to think about it.

[Maria_1969]

Well, in 2008 I was a witch and my SO was my sexy black cat and my motorcycle was dressed up as the broom to ride.... Its definitely easier when you have a supportive SO that will play along and do a complimentary costume.

However, we have done this costume back to back years now so we are also talking about 2009 as well. We BOTH agree its better to do a female costume rather than just dress as a woman. Our plans vary for 2009 and here are some of the ideas we have....

Me - Dorothy
Her - Glinda

Me - Ballerina
Her - Male ballet dancer complete with very exaggerated bulge.... (probably the most funny but daring idea for us)

Me – pregnant Angel
Her – Devil

Me – Cheerleader
Her – Football player

[JoAnne Wheeler]

Look bad/sloppy - everyone thinks that that is just a joke --- Look beautiful --- everyone thinks that you must be GAY

So in the mind of us crossdressers - you are DAMNED if you do and DAMNED if you don't.

Why don't you try to find a party for crossdressers primarily - no problem then

JoAnne Wheeler

[Jean Ann S]

I have two Cheer uniforms
one blue and gold from e-Bay
Another blue andwhite I got from a Cheerleader supply
Also remember to get color co- ordinated Cheer shoes
Socks Pom Poms and maybe a letter Jacket
Wear mine every year !

Jean Ann

[TrekGirl1701]

Has anybody or anybody you guys know been questioned about wearing a female costume to a Halloween party?

I want to believe that I'm making too big of a deal about this, but I just don't want anybody to know yet that I crossdress. Especially my family, whom I'm very close to.

[beenherelongtime]

you have to make your own decision. i myself would prefer to present as a real girl. now i am going to write about something that i did years ago. not that many, i think i was in my sixties. a friend of mine owns a restuarant and he was having a halloween party, he had one every year but i never went dressed.

the year i mentioned, i don't really know(just came to me) 5 years ago., where my mind set was but i stopped in after work and had a few drinks(to me a few then was 5 to 10).
before i left people in costume were coming in. realize i had been drinking from about 5 to 9pm. i had become uninhibited enough that we i got home, i decided to go back dressed. not a great idea because i then had to rush, my makeup, my dressing. anyway
i showered, put on a long clingy black dress, with accompaning underwear, my size d breast forms and my 4 or5 inch heels, making me 6'8 or 6'9. any way when i got there, most people that knew me guessed who i was( see height above). i did not get any hoots or boos. most people just thought it was a halloween costume, but the more astute knew you just didn't throw this outfit together on a whim. one particular girl, the sister-in-law of my hairdresser, said to me, "i've known a few you're a crossdresser, aren't you?" i told her yes, and her comment was "i love you earring", that was all, so being the kind of person i am, i told her i would give them to her before we left.

i could go on for a long time about the grabbing of my boobs or about the conversations i had, but that is not my point.

i guess you could say this was my coming OUT to my friends. After this when i would underdress for work, i would go into the bar with definately some female article of clothing, such as slacks, or a blouse or both. naturally with a bra on. i never got one bad remark about this, and this bar had a large crowd of men and women that came in.
i would even sit with the owner(my friend) and his wife and nothing was ever mentioned about my clothing. so you see there are a lot of people out there that take you for just who you are, not what you are wearing.

[Kelli Michelle]

I think it depends on where you go.

If you go to a party where everyone knows you or just a regular party or bar, than I would say go as a pop person, but definitely as they would be in a costume. Madonna comes to mind. Cher is a good one. Also I have seen guys go dressed in things like a 50's housewife, or a bobby-soxer, a goth girl...those went over well. I would stay away from gross caricatures or little girl type stuff. I could see stuff like a hooker, a sexy female cop, or the like. For some reason those seem acceptable. I was at a party a few years ago, and one of our regular friends did just come as a female, not in costume. He looked very good. His girlfriend helped him out, and he looked quite reasonable. He just walked a round with a big smile on his face and engaged everyone and had fun with it. He was no cd. Also, I would say, don't act too overtly ladylike. I think subtlety is the word here, if you go as just a regular woman, without a costume.

If you go to a gay bar, anything goes. I have seen slaves, french maids (I was that this year---great fun), Mae West, Tina Turner. Some costumes were demure, some were very racy.

With all this time to plan, I am sure you will come up with something great.

[suzypier]

I am also looking forward to it. The last one was my only time out with people in public (beside a few drive at night).

[Sally2005]

It is pretty hard to have it both ways...to dress like a woman and to look like it is just for fun, but it is possible. Remember, most people will not beleive it is anything more than halloween unless you act strange. They might think you went a little too far, but no big deal. You will hear jokes about it forever and actually it makes you cool in your friends eyes, but it depends on how you react to their jokes (you have to go with the flow).

Great costumes are ones that are popular characters that can only be done as a female...ie: hanna montana, barbie doll, witch, hooker, biker chick, political figure... the even better costumes and more cool are couples that role reverse...hooker and pimp, etc.. You can even get a few guys together and do it, but that's harder to convince them and then you are probably stuck with the guy in a dress look.

oh, and a really good cover story is to have a girl friend who invited you to the party and did it to you.

[Di]

I shutter to think of you worrying about this for 10 months.....I hope not
If you want more info...look in the Oct threads there are over thirty ( I stopped counting at thirty) posts about halloween ..what to wear...what to say around friends and just about everything you can think of.Hope you find your answers.

[debbeelee1]

I had a Halloween party last year and dressed as a sexy witch. I guess I sort of outed myself to some close friends by doing such a great job on my "costume" and make up. I was the hit of the party though! Next year, I plan to have another party. I'm going to be a sexy Fairy Godmother this time. Hey, it's my party and I'll dress anyway I want!

[TrekGirl1701]

I shutter to think of you worrying about this for 10 months.....I hope not
If you want more info...look in the Oct threads there are over thirty ( I stopped counting at thirty) posts about halloween ..what to wear...what to say around friends and just about everything you can think of.Hope you find your answers.

Thanks for the suggestion. I think I'll do that.

It's a double-edged sword, I guess. If I go as a female I'll be more comfortable, but I run the risk of people I'm close to finding out about my crossdressing habits. On the other hand if I don't go as a female then I'm not going as I truly want to be and I don't think I'll have as good a time. Halloween is supposed to be fun and I think I'd have more fun going as what I really want to go as.

I'm really leaning towards going as a female. I'm sure I'll change my mind a million times between now and then, but I'll have plenty of time to think about it.

Thanks everybody for your input!

[Gabrielle Hermosa]

If I go as a female I'll be more comfortable, but I run the risk of people I'm close to finding out about my crossdressing habits. On the other hand if I don't go as a female then I'm not going as I truly want to be and I don't think I'll have as good a time.

You know - if you pull this off, as in keeping secret your cding as a personality trait and not just a Halloween thing, you may pick up some valuable information about what your friends/family think of it. You'll have the opportunity to test the water a little and still be able to do a u-turn if the water turns out to be cold and uninviting. Of course, you'll run the risk of people putting 2 and 2 together, but you might be able to plan for that since you're thinking so far ahead.

I hope you find a way to go through with it. I really enjoy reading about people who are brave enough to go out en femme, even if only on Halloween. I have to live vicariously through you other girls who are more passable and/or just have more courage about it.

[trannie T]

Why are you waiting until the last miniute to decide on a costume? You have only a little more than nine months to make a decision.
There are not nearly enough Halloweens in a year, so I have found many more times to go out dressed.
As for what to wear it is your decision. What turns you on? What would you be most comfortable wearing? What would look good?
whatever you decide on, get out and have a good time!

[TrekGirl1701]

You know - if you pull this off, as in keeping secret your cding as a personality trait and not just a Halloween thing, you may pick up some valuable information about what your friends/family think of it. You'll have the opportunity to test the water a little and still be able to do a u-turn if the water turns out to be cold and uninviting. Of course, you'll run the risk of people putting 2 and 2 together, but you might be able to plan for that since you're thinking so far ahead.

I was thinking about that. Halloween is a very good occasion for a closeted crossdresser to 'test the waters' like you said.

I won't be as scared to go out CDed if it's a fun occasion like a Halloween party. I think it'd be a major step in the right direction if I did it.

[xingdays]

Going by your screenname you could go as a star trek yeoman, from the original sreies. Or maybe Counselor Troi from next generation. Or even 7 of 9 from voyager...

[Teri Jean]

This past Halloween I dressed in period clothing (renaiesance) and the long skirts and peasent top was fabulous. They knew how women should dress. The down side is if you do your makeup to the 9s someone will notice and you may be in for some questions that you may not want to answer. I did and get quizzed every so often. Look at it this way we have a whole year to work on the next outing at work or party. Keli

[Sakura Rini]

we dont really do Halloween in Australia, but im going to dress up anyway, i have afew ideas
1 alice in wonderland
2 girl scout
3 Dorthy from wizard of oz
4 french maid

i cant decide on them, but theirs plenty of time my list might change later on

[Maria_1969]

Has anybody or anybody you guys know been questioned about wearing a female costume to a Halloween party?

I want to believe that I'm making too big of a deal about this, but I just don't want anybody to know yet that I crossdress. Especially my family, whom I'm very close to.

Go for it, its very liberating..... I am a biker, my friends are bikers and it went over very well. I was even picking up the dress showing them hosed bare squished equipment and just having fun..... (I have pictures to prove that...lol). I was getting my ass smaked, dancing and all. If I can do this with bikers and have fun and still be respected you can do it too.

Then again I am extremely masculine anyway, so no one questioned it at all. I wore the costume to 3 different parties this year, 2 of them were biker parties..... The girls at the parties loved it too, adjusting my boobs and asking my SO why I walk so good in heels.... LOL

Play with it, if anyone says I bet you like it... say, maybe I do, you should try it, the pantyhose feel great! If you act like you are nervous and not having fun doing it, you may be questioned about it more. The best comebacks are ones they will not expect, shock them!

Fact is, if you are comfortable in your sexuality no one will question you too.

ALSO, if you are single and looking for a GG SO, the best way to get an accepting one if doing it on Halloween... thats when the girls that like it show their true colors..... Thats a fact! Even with my SO next to me, the girls that liked it wanted to be near me and talk.