Halloween Plans And Advice Needed

[Sarah L.]

Okay,here we go:
I will be out of town that weekend by coincidence.I will be making the drive home on Halloween day.I won't run into anyone I know until I am close to home(if then).So I thought I would make this my first Halloween dressed.My few appearances in public have been quick in and out things,so this will be my first time out for any real length of time.
On the night of the 30th,I will lock my icky boy clothes in my duffle bag(with the key in the glove compartment,just in case!),so I can't back out on the 31st.Once the duffle bag is locked up,I will have no choice but to put on a dress to get to the car.I have arranged to leave my motel key in the room,so I won't have to go to the front desk if I don't want to.
Halloween morning,get dressed and made up and out the door.I plan to make enough stops along the way to turn a 5 hour drive into about 8 or 9 hours.I want to stop at restaurants and eat inside and go to department stores and just walk around.I want to get the confidence to go into a dress shop and buy something and know they know it's for me and not care.
I am going to treat it like an adventure and maybe learn a little bit about myself and what I can do if I let myself.
I don't have a blog or a twitter account(and don't really want one of either),so I plan to take a small notebook and make notes about what I am feeling at different times and reactions I get.I will post those here in case anybody wants to read them.If it gets too boring,I will add a car chase and some bad language to spice it up a bit.
I think I would pass okay if I were better at doing make-up,but if I get spotted(and I will!)in a restaurant or Walmart,it's just another guy in a dress today.I will get a few laughs directed at me,but that's alright.
Now,some questions.I have read posts saying you should use the bathroom you are dressed for,but this must be different for Halloween,right?It seems on this day,a crossdresser who gets caught in the ladies room might have trouble convincing people he is not just a guy in a dress on a lark.What do you think?This shouldn't be an issue anyway,I am looking up places with gender neutral or family bathrooms along my route.
Also,I would like to go to Macy's and get a makeover/consultation.Have you gone to one of these?Have you worn makeup to one?Is there a place to wash off what I put on?I guess it seems like a waste of time and money to do that,but it would be nice to show them the horrors I present to the world when I do my own.I am not really putting myself down,I think it would be easier if they see what I am doing wrong.I look like Reese Witherspoon before I put on makeup,should I really look like Ernest Borgnine when I have my make up on?
I know if I get a makeover or stop at Victoria's Secret while wearing a dress,it will be a giveaway,but I feel like this could be a big step for me.
When it's all over and done,I will know the Earth isn't going to open up and swallow me if I choose to be myself.
I know I am not inventing anything,but I thought I would run it past everyone to see if I am making a big mistake or if I should go for it.If you see something wrong with my plan,please tell me.I won't take it as someone being negative,just giving the advice I am looking for.Thank you for reading this.

[Davita]

First, is your costume a guy being a girl in costume or are you going to be a girl in a costume? If you're a girl in costume and you're passing well enough, then ladies room it is. Heck, being the brazen girl I am, I would probably do the ladies room if I passed or not. However in today's world, there are getting to be plenty of those family potties, so the odds are good you're safe.

Let me point you to my first Halloween, I posted my lessons learned and there may be a few pointers for you. To be honest, I didn't quite pass, but that was the reason to use Halloween for that "just in case". Anyway, see http://davita-farley.webs.com/outings/haloween.html. Hope it helps answer some of your concerns.

[Absaroka]

A lot of places have a "family bathroom" or unisex bathroom. It's oriented towards parents with children of the opposite sex but can come in handy if you aren't sure which one to use. Typically they are meant for one use at a time and you lock the door. Likewise at places like Dunkin Donuts there is just one toilet and you can lock the door.

I like to dress when I drive long distances and I absolutely do not pass. I tend to use the woods at the far end of the rest stop at these times.

Personally I wouldn't do the whole locking things away bit. I like to have my options completely available to me. Anything else feels like dressing against my will, which I don't like in either mode. But that's just me.

Have fun and please let us know what happens.

Zari

[Sarah L.]

Thank you for the responses and thank you for the link,Davita.This Halloween,I will just be a guy in a girl costume.I thought about things like:maid(not the french kind,the world has done nothing to deserve that nightmare),flapper,etc etc but just decided to keep it simple this time.The idea of locking my male clothes away is not to force me to dress,just to keep me from failing to go through with it.There isn't much distinction between the two(I know)but it depends on how you look at it.Besides,the key will be in the glove compartment in case I need it on the road.I work goofy hours and must go to bed very early through the week,so enjoying Halloween is only a realistic option when it falls on a weekend.This will be the last Halloween on a weekend for a number of years,so I will be kicking myself for a long time if I don't take advantage of this one.I chickened out 2 years ago and have regretted it ever since.Last year,I had to work.I got home and fell right to sleep,missing the whole thing.I have requested off on November 1st,so I can stay out as long as I choose.

[Absaroka]

If you are a guy in a girls costume, use the mens room.

I have memories of going to the gym in costume one Halloween. Lets just say that taking off your bra in the mens locker room feels odd, even though no one cared. I couldn't bring myself to put it back on after, although I had no choice about the other clothes.

Zari

[Sarah L.]

This sounds like a story I think we would all be interested in reading.

[Kat]

Other than the restroom thing, its Halloween! anything goes in my honest opinion. Good Luck and update!

[Absaroka]

Most of the story involved getting ready for Halloween. I decided that with Halloween as a pretext I'd find out what bra size really fit me. I went to Bare Neccesities (they weren't just on line back then) and explained that I needed a bra for a Halloween costume and they measured me and offered me a bra to try on. On the way to the fitting room I asked how much it was and they told me. At that point I realized I had no intention of buying a bra there, and it didn't seem right to try on stuff when I knew I wouldn't be buying anything. I explained this to them, thanked them and left.

What I remember is that the two sales associates found the entire situation to be funny and laughed, but in a pleasant and friendly way that put me at ease. Later I realized that if I was going to be honest about wanting to buy a bra for myself that I needed to allow them the honesty of their reaction as well.

I got a bra that fit with an extender somewhere else. Most of the other clothes I already had, but was given a pair of long striped witch socks from my eldest daughter and borrowed a skirt from my wife. I walked around and did errands in my long skirt, top, wig, hat and etc and got a number of humorous favorable comments. I went to visit the ladies at Bare Neccesities and they admired the costume. I commented that there was no where to keep my car keys (I hadn't thought of a purse) and they said "keep them in your bra" The guy at the gas station found this also to be pleasantly amusing and very nicely suggested that next time I include a purse in the ensemble.

The ladies at BN commented that my breasts were tastefully sized and not over large like some men do when they dress in female costumes.

My wife was mildly irritated that I had borrowed one of her skirts and told me to use a different one. I think she was also a bit put out that I had time to do all this (I'm self employed) while she worked all day, even though she too went to work in a costume.

That evening I wore the costume when I went to the gym. It attracted no comment whatsoever. However when I got dressed again after it just felt wierd to put on a bra while mostly naked in the mens locker room, so I didn't. No choice about the skirt, panties, or top, and I put the wig back on to be more convincing. At that point I was using a black teeshirt in lieu of a slip for some reason.

I did the same thing the next Halloween and went for a walk in the woods. Someone called the police and they wanted to know what I was doing. I thought maybe the witch costume pissed off some Wiccan but my wife pointed out that the woods was very near a school. The police were very pleasant, asking me about guy stuff like how did I like my car, while waiting to have me checked through their data base. But I decided I didn't want to do this again.

Zari

[KimberlyS]

...This Halloween,I will just be a guy in a girl costume.I thought about things like:maid(not the french kind,the world has done nothing to deserve that nightmare),flapper,etc etc but just decided to keep it simple this time.

Sarah I am not completely clear on how you will be getting out.

Will you actually be wearing a costume?

Will you be out presenting a feminine/female self image to the world?

And if the latter how blending is your feminine image? As this will determine which restroom you use. A decent blending image is all you need in most cases as there is no such thing as a perfect feminine image. And many GG's are very masculine looking. If you use the womens, go in, pick an open stall, sit, go, wash hands, get out. Do not take any extra time.

But either way being Halloween you can easily go into the mens restroom, hike up your skirt/dress and use the urinal. If someone comes in make some comment about your GF/Wife talking you into it or some comment about not being able to stand PH or similar.

How ever you get out enjoy your time.

kimberlys-cd
joe in a skirt

[Sarah L.]

...This Halloween,I will just be a guy in a girl costume.I thought about things like:maid(not the french kind,the world has done nothing to deserve that nightmare),flapper,etc etc but just decided to keep it simple this time.

Sarah I am not completely clear on how you will be getting out.

Will you actually be wearing a costume?

Will you be out presenting a feminine/female self image to the world?

And if the latter how blending is your feminine image? As this will determine which restroom you use. A decent blending image is all you need in most cases as there is no such thing as a perfect feminine image. And many GG's are very masculine looking. If you use the womens, go in, pick an open stall, sit, go, wash hands, get out. Do not take any extra time.

But either way being Halloween you can easily go into the mens restroom, hike up your skirt/dress and use the urinal. If someone comes in make some comment about your GF/Wife talking you into it or some comment about not being able to stand PH or similar.

How ever you get out enjoy your time.

kimberlys-cd
joe in a skirt

I won't be wearing any kind of costume.I plan to dress as if I am trying to pass,but without the stress of needing to pass.I don't mind if anybody suspects that this isn't just for Halloween.I plan to wear this dress: [url] http://www.blair.com/product/Womens/Dre ... 0/7866.uts [url]
In fact, I bought it just for this occasion.For my first all day outing,I wanted a whole new outfit.I have been called "maam" in guy mode and I think I have been spotted in girl mode.

Thank you everyone for your replies.
Also,thank you for the story,Absaroka,I enjoyed reading it.