Halloween question

[connie johnson]

My wife and I are invited to a halloween party and she insists that we both go as a hookers. I never go out dressed and I know this is my chance to do so. I'm just not sure I want to be a hooker. IF I do go out dressed I want to go with something a little more conservative.

She told me I can get a wig, nails, a new outfit and shave my face (I have a full beard). These are things I have been wanting to do for a while.

I'm afraid I will be too scared to go out when I'm all ready. She keeps telling me that everyone will like it and not think that I crossdress on a regular basis. It will also be difficult to explain how I can walk so well in 4" heels.


this is my big chance to dress outside, what should i do?:o

Any thoughts and comments are appreciated.

Connie

[Inachis]

Don't make excuses, GO FOR IT, I bet it will be fun. If you do not want to go as a hooker then try a police woman busting a hooker. But, don't let the opportunity pass you by. I have gone dressed on Halloween before its fun. My only problem is this year I am working.:sad:

[Kimberly Marie Kelly]

You will be nervous, but think like its a costume and enjoy it. As for being a hooker, don't go as a typical street-walker type hooker, go dressed up as a classy call girl escort type. That way you can be dressed to the Nine's and look gorgeous, your SO can be the typical hooker look.

Kimberly, says just do it. You will enjoy it. :battingeyelashes:

[Jonianne]

I'm like you, I would perfer conservative, however, since your wife is so willing to help and wanting to enjoy the time with you, I think I would trust her. Maybe you can go as Julia Roberts!

[susan2010]

you are lucky you can go out. Go for it! And stumble a few times and complain about the shoes if you're afraid the neighbors will guess.
Have fun!

[Annie D]

Are you serious? It will be for only one night and then with your beard gone, you will have many nights of fun going out enfemme. Of course, your wife may secretly want you to shave your beard and by enticing you to become a very naughty girl may get what she wants. It seems to me that it will be a win/win situation. Worried about walking in 4" heels, buy 6" heels but bring the 4 inchers for backup. Like everyone before me has said, "Go For It!"

[MarinaTwelve200]

DO IT! I am a "Closet case" myself and the only time I have been out was at a Halloween party in 2004---I was dressed as a "GYPSY FORTUNE TELLER"---really over the top with exotic makeup ,Nails, dalse eyelashes, jewelery, etc. A COSTUME,I found, takes the "CD- EDGE" or "Creepiness factor" off the experience---enough so that I COULD let myself be seen, despite my "nervousness"' I likely could NOT have done it had I been disguised "conservativley"--say as simply as "a woman"

A "Hooker" is a great costume for a guy, Just as a "gypsy Fortune teller" or even "Elvira". it dosent look as "serious" (or suspicious) as doing a "straight up" female would be, and any comments can be laughed off---In fact I did a LOT of laughing, myself---I was the hit of the party.

Not only is this a chance to safely "test the waters" of being out in female clothing, you are very LUCKY to have a wife to support YOU there too. DO IT! you will find it Lotsa fun.

Of course, I havent been out in drag SINCE, but still I know what the experience is like and no one thinks anything negatively about me for having done it. YOU have the perfect excuse, and the perfect costume and a hand to hold if you get nervous--GO FOR IT. Otherwise you will regret not doing it for years.

[Sally24]

If you go really over the top people will take it as a "costume". If you do a really nice, pretty, woman people may suspect more in that case. Have fun with it and see where it goes. If they comment on the flair you have with high heels tell them your wife made you practice all month long!

I've only gone out on one Halloween but it is so much fun!!

[Raychel]

Are you kidding me, I would jump at the chance, If my wife had said something like that.

We are supposed to be going to a halloween party, She has not said anything about dressing up yet. :Pray::Pray:

[Jonelle]

um........ GO FOR IT!!!!!!

[curious123]

not only should you go, you should attempt to out-do your wife in the way of dressing up

[Ria]

oh yeah... If you don't do it, you will regret it. I could only wish for my wife to suggest such a thing! Not going to happen.

I would ham it up if I were you. The more you do, the more fun you will look and ironically- the less like a crossdresser you will appear.

[Holly]

Ultimately it is up to you, Connie. If you don't like the hooker idea, suggest something else to your wife that you are comfortable with... movie starlettes. cowgirls, let your mind run wild! The most important thing is to make sure that you both have fun!

[Amy Hepker]

Hey Go for it, don't miss out you will be kicking your self for the rest of your life. Just go with the flow and enjoy!!!!!

[renee k]

My wife and I are invited to a halloween party and she insists that we both go as a hookers. I never go out dressed and I know this is my chance to do so. I'm just not sure I want to be a hooker. IF I do go out dressed I want to go with something a little more conservative.

She told me I can get a wig, nails, a new outfit and shave my face (I have a full beard). These are things I have been wanting to do for a while.

I'm afraid I will be too scared to go out when I'm all ready. She keeps telling me that everyone will like it and not think that I crossdress on a regular basis. It will also be difficult to explain how I can walk so well in 4" heels.


this is my big chance to dress outside, what should i do?:o

Any thoughts and comments are appreciated.

Connie

Hi Connie,

GO FOR IT!!!
If I were you I won't give it another thought!! Especially with a supportive wife, like yours!!

Huggs, Renee

[tamarav]

Nothing ventured, nothing gained...

Get out there and show them how much of a woman you really are. Be all that you can be (sorry Army) and do the very best job possible and above all, have fun with it.

Your sis,

Tami

[Kate Jennings]

Go for it.

Go with the "real woman" look and if anyone asks and you feel a need to justify tell them you are Eliot Spitzer's gal pal!

["Mary"]

My friends ahve pretty much said it all. I agree.

Go for it. Go classy call girl. You will so regret it if you don't. This is your big chance. You have a freaking invitation to do this!!

BTW - My wife and I will be going as cheerleaders this year.

[elusivebeauty]

Yeah, if some one is going to support you and be with you while you do it, even better! It could be harder and you could have no one willing to do that with you. Take the golden egg and have a good time.

[kimmy p]

If people ask you how you walk so well in heels you simply tell them that your wife suggested that you practice walking in them for a week or so before the party. Last year when it was commented to me how well I was walking in heels I responded that A. it wasn't my first Halloween as a female. and B. To me heels didn't feel much different from ice skates.

[Tina B.]

Girl, a chance to dump the beard, go out to a fun party, as a woman, what is there to think about, if I had that chance, I would go as lady Godiva if that would get me there, let your wife lead, and wear what ever she is comfortable with you wearing, she will not suggest anything that would embarrass her or you, I am sure. who knows maybe would even have to shave your chest if the outfit revels to much. LOL! And as far as walking too good in heels, get yourself a pair with stocky heels, and tell them it is just like wearing cowboy boats (wink wink, I'll say no more!) Have fun, being nervous can be part of the fun and thrill!
Tina B. :devil:

[Cristi]

I can predict that on the night in question you are going to get EXTREMELY nervous as you get ready to go out.

Actually getting out the door is going to be tough... as is making your entrance into the room full of people at the party.

But I guarrante that no more than 5 minutes after you enter the room, the stress will go away and you'll just be able to enjoy yourself.

In 20 minutes, you'll have almost forgotten how you are dressed at times.

Somewhere around the one hour mark, you'll be involved in a conversation with somebody else, then look down at yourself, seeing the boobs, short skirt and stockings and get a thrill when you suddenly remember what you are wearing. :)

And at the end of the evening when it comes time to go home and take it all off THEN you'll know the meaning of "not wanting to do it"!

You MUST do this. As others have said, these opportunities don't come along all that often and we must take advantage of them when they do, or you'll regret it for years.

[Brina Halloween]

I agree...go for it.

I have not found a really comfortable 4" stiletto for me but, it does not take long to get used to them. An hour or so a day for several weeks. It is 4 weeks until Halloween, plenty of time to have practiced. You even have an SO to deflect any negatives, any rude or offended people have to deal with her.

Brina

[Roberta Marie]

Halloween is all about letting go of your inhibitions and pretending to be something that you are not. The more outragious and deviant from your normal character the better. You sound like you normally dress rather conservitively. What could be more radical from you normal personallity than a hooker? How about a PREGNANT hooker!! Maybe ocasionally lift your top to show a big belly displaying a sign "Who's my Daddy?"

Halloween is the one night that we can really let our hair down, and be expected to be something that we are not. I agree that you should jump at the opportunity and go! Where I disagree with all the others is, go and be something that you are not, something that no one would expect. But by all means, have fun.

Grace,
Bobbi

[Veronica27]

Regretting that you did not take advantage of an opportunity when it presented itself, is harder to deal with in the long run, than dealing with the chance that your friends might wonder about your motives and ask questions. They will tend to forget the incident over time, but you will never forget your lost opportunity.

Halloween, and participating in a crossdressing event, are two of the easiest ways to get yourself out of your self imposed closet. In the first case people expect to see others in costume, while in the second case people you encounter are expecting to see crossdressers at a crossdressing event. It is highly unlikely that they would know you or vice versa.

Having your wife encouraging you to do this is an added bonus that many crossdressers do not have. If your "costume" complements hers no one will suspect anything, and will be more inclined to think it is her idea and not yours. The best bet is to let her pick out what you wear, assist with your makeup and do most of the explaining at the party. That way you are being truthful in your efforts to hide your desires, and the delight you are experiencing by doing this. Let your wife be aware of your preferences, but then let her make all the final decisions.

No matter how nervous you feel about it, if you don't take advantage of the opportunity you will regret it forever.

Veronica

[briannad]

What are you waiting for? Get out there. Just having your wife by your side is reason enough. Go out and enjoy yourself.

[connie johnson]

wow! everyone says i should do it, so i think i will.

now i have to go get a wig and start practicing the look and walk of a hooker. most of all i really need to phych my self up.

cant wait.

love connie

[Kayla_CD]

go Go GO!

Embrace this chance and enjoy it!

[kaitlin]

Hey Girl, It sounds like your wife is supportive and is making her best effort by wanting to do this with you! If you pass on this chance you may never get another one! I agree with all the other girls, GO FOR IT !!! Kaitlin

[Katheryn]

My wife and I are invited to a halloween party and she insists that we both go as a hookers. I never go out dressed and I know this is my chance to do so. I'm just not sure I want to be a hooker. IF I do go out dressed I want to go with something a little more conservative.

I'm afraid I will be too scared to go out when I'm all ready.
Connie

Halloween is a great excuse to take that big step outside. It was mine.

I understand the fear of going out first time. Halloween didn't scare me, as it was a costume wearing night, of course. But one night my wife and sister and Kate planned to go out to a restaurant for a girls night out. The more I prepped for it, the more scared I got, but my sis finally calmed me down and we went to Olive Garden.

Turned out to be just a great night, no problems at all. Oh, and when the server said "Good evening, ladies, can I get you a drink?" I got a thrill.

Kate

[Sally2005]

Let my tell you about what we did... We dressed up as bikers. I was the biker chick and she was the biker dude. I wore a good quality wig, but one that was pretty full, sort of 80's style...heavy makeup and losts of temporary tatoos. I wore a jean skirt and tight top with balloons that were a little bit over inflated. Long black boot and fishnet stockings. Also I wore a small jean jacket. All this I got at the trift stores for next to nothing. We dressed my wife up with fake beard etc. If you want to do a hooker, get your wife to go as the pimp. This was one of the most fun times I ever had dressed. My friends all loved it, I had one macho male friend get all nervous so had some fun joking with him until he relaxed and saw that I was still the same 'guy'. All the women loved it and they all came to talk and ask about it. If the questions get too personal, just say your wife helped. One woman I poured a drink for and spoke with in the kitchen later talked to my wife and my wife said, 'you saw my husband..." and she said, "husband?! That is your husband?!"...with total shock...she thought I was a woman, even though I spoke in male voice and was obviously a guy doing drag. That was a great laugh and even after a lot of explaining she still looked confused. So do it, you will have a great time! Also, your male friends will think you are the most cool person they know! It is amazing how many times I have done halloween dressed and no one, not even my wife suspects anything unusual. :-)

[trisha59]

Its unanimous go for it. But I want to second the Cop and Hooker idea. I think that would be adorable. Next year you could go as client attorney and the following year convict and Jail matron. Wow I should be in event planning.
Trisha

[trannie T]

Don't dress up.
Stay home.
Have something to regret for years and years.:eek:

[Kate Lynn]

I hope you post pics,I'd like to see what you decided to do,sounds like fun.

[Katheryn]

Don't dress up.
Stay home.
Have something to regret for years and years.:eek:

<sniff sniff> Hmmmmm I smell facetiousness!

Kate

[DameErrant]

Go for it baby! Halloween is a time to cut loose! Conservative is fine for a support group meetning, but Halloween is for fun.

I'm going as a Dominatrix. Now if I could just get my wife to agree to be my Submissive.

[Debra Lynn]

You have the perfect opportunity to make your first foray into public view. Not only that, but your loving wife is encouraging and supportive! I agree, let her help you get the outfit and get ready for the party and let her take the lead on any explanations. I've dressed for Halloween at work for the past five years and outside of the female complaints about how well I walk in high heels, 99% of the response is joking or positive. (yeah, there's always someone whose a pain, but they can be ignored, they are only 1%)

You do not want to waste this chance to be true to yourself with someone supportive next to you! Sure you'll be nervous at first, but it will pass and you will find it's fun!

If they comment on how well you walk in heels, tell them you have a great sense of balance (which is true, most crossdressers have an unbelieveable sense of balance since they are balancing thier female and male sides! LOL)
and then tell them practice makes perfect.

[suchacutie]

I agree with everyone totally...do it and play it up big time. Any guy can practice in heels ahead of time so just say "my wife made me practice!" I'm sure the two of you will have a sexy time, and let her enjoy herself!

tina

[Tracy Hazel Lee]

Do it. You'll be very upset with yourself if you do not.

My first real outing was on halloween, and I did it two years in a row!

Needless to say, my friends weren't quite as amused the second year... But they still thought it was all in good fun...

Good thing for me, I wasn't nearly as good at it then. :battingeyelashes:

Dunno how they would react now, they would most definitely know that this is not 'just a halloween' costume... (with now 10 years of experience)

[Kayla_CD]

wow! everyone says i should do it, so i think i will.

now i have to go get a wig and start practicing the look and walk of a hooker. most of all i really need to phych my self up.

cant wait.

love connie

Glad to hear it, hope you have a wonderful time!

[Genifer Teal]

My wife and I are invited to a halloween party and she insists that we both go as a hookers.

It will also be difficult to explain how I can walk so well in 4" heels.

this is my big chance to dress outside, what should i do

Connie

Go & have a blast. If your wife is into it, follow her lead. As others have said, dressing over the top is less of a givaway on halloween. As for the shoes, just explain that after your wife suggested it, you immediately tried on a pair of heels and realized you needed to practice - so you didn. Guess you are a fast learner.

Gen

[TxKimberly]

Don't be silly - do it.
Here is the question you SHOULD ask yourself - How long are you going to hate yourself and cry inside if you pass up such a perfect change to have fun?

Oh, and the four inch heels thing? I don't recall ever having a problem with them. The stuff you see in the movies and on TV greatly exaggerate this and most women are going to know this.