Halloween ideas/planning/logistics. Please help!

Hi everyone!

I'm looking for advice regarding Halloween and how to best organise/plan things. For your information I've never been outside my home en femme in any way before.

As I've said in previous threads my Wife is DADT and although I've sent her pictures of me in high heels and stockings etc she's never wished to see me actually crossdress 'in real life'. I've been as honest and open with her as she will let me.

I've spoken to her on several occasions recently regarding crossdressing and halloween, and I've explained that most of my ideas for halloween this year did involve expressing my feminine side. She now seems okay with this, hasn't refused, and has simply raised practical aspects with me, such as her worries that I won't be able to actually face going out en femme due to anxiety. She's raised the issue of make up and wigs and has said she's not overly sure about helping me with things.

I've looked into costumes and purchased two so far. A demure and elegant Snow White gown and a more revealing sexy angel costume. Both fit me and I'm comfortable in both in private at home.

I have found a dressing service locally which only deals with CD/TS etc. I've found another company nearby who specialise in wigs/make up/makeovers mainly for cis females with cancer/alopecia but they appear to be friendly towards CD/TS/TG etc also.

Given that I've never been out before do you feel I should go to a cd dressing service, take the wigs I've purchased, let them 'make me over' then drive home en drab and get dressed at home. Or do I go to the specialist wig/makeup place? They are much more expensive, and you have to purchase the wig from them but I think they might be better at helping one 'pass'.

Should I brave coming home from either service in an outfit that isn't my costume but isn't drab? Perhaps a simple dress and coat? Is making my first journey outdoors en femme realistic in this manner? Would it be better done with someone with me?

I'm so over the moon that my SO is discussing the issues with me, albeit tentatively. I don't want to overwhelm her though. I've said to her that I'm happy to pay a professional to do my hair and makeup, she didn't say no or object, her main concern seemed to be whether I could cope with it or not.

I don't want to upset her or ruin her evening. I adore her and I do not want to "ruin her image of me" etc.

Any constructive advice is very welcome! Xx.

Best wishes.

Vivienne! Xx.

A number of threads have discussed this topic recently. The general consensus of opinion (if I've read it correctly) seems to be that if you look 'too good' you're pretty much outing yourself as a crossdresser to the world. Maybe you want that, I don't know. Others have claimed it is a 'free pass' to go out en-femme. again opinion is very much divided. I've fantasised about doing such a thing but doubt if I could actually carry it out as my SO does not know of my Cding, (I think....)

Hi Vivienne, A couple of things you forgot to mention in your post is are you going out to a house party or bar ? Will friends and family be there and are you worried about being seen by them or are you just worried in general about going out in public Are you going Alone or is your wife going with you ? One way to ease your wife into your dressing if she is willing and is into Halloween is to make her a part of it by choosing costumes for a female couple.This year my wife and I are going out as Max and Caroline from 2 broke girls and in the past we have gone as Daphne and Velma from Scooby Doo. Others that come to mind are Xena & Gabriel,Edina and Patsy from AbFab, the list is endless. In this way it can be fun for your wife as well as you and it wont look as odd to friends or family that you are dressed as a female. As for the different services the one that deals with CD/TS clients only will have a wider choice of foundations and tricks for doing a makeover on a male face not to mention all the other little things one learns to be more convincing. Remember, Covergirl doesn't cover boys.As for driving home take a dress or skirt and blouse and enjoy the drive home. It is Halloween after all. I Hope everything goes well whichever way you do it.

Hi Diane, I know it's not a free pass and that there are risks involved. I would like to be as convincing as possible though, and would prefer people thought I might be a crossdresser rather than thinking I was trying to disrespect woman or trans people in any way.

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Originally Posted by April Showers

Hi Vivienne, A couple of things you forgot to mention in your post is are you going out to a house party or bar ? Will friends and family be there and are you worried about being seen by them or are you just worried in general about going out in public Are you going Alone or is your wife going with you ?....

This year my wife and I are going out as Max and Caroline from 2 broke girls and in the past we have gone as Daphne and Velma from Scooby Doo....

As for the different services the one that deals with CD/TS clients only will have a wider choice of foundations and tricks for doing a makeover on a male face not to mention all the other little things one learns to be more convincing.

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Hi April.

We're going to a burlesque halloween event where there will be several thousand people present. It's a very forward thinking event in terms of all shapes and sizes and they are a CD/TS friendly company.

My Wife and her Sister will be going as will one couple we are all friends with. I know the risk is that will think I'm taking it too seriously and might wonder if I crossdress. We are very close to the other couple and they have previously mentioned him trying on her lingerie in the bedroom, so I don't think they would be derogatory about me.

I'm not too worried about the event in terms of being seen by strangers or by those we know. I'm more worried about travelling home after having my makeup and hair done. The initial worry about getting back to my car alone concerns me.

I'm a little worried about my Wife's parents reaction as I think they will be babysitting for us and hence they might see me leaving the house. I think I'll laugh things off or say my Wife dared me to do it. Or I'll see if we can drop the children off at there house before the transformation occurs!

Your ideas for the couples costumes are excellent!

I think you're right re the choice of professional to go to.

Xx.

Go as Harley Quinn, there will only be 10,000 other people dressed like you. (Meaning you will blend in more)

Here is my advice: Don't ask for advice from strangers on the Internet, ask your wife. She knows you best and if she suggests something, she can't be upset if you do it.

I will say this though, there's little point in paying someone to make you up as a female and then undoing it to drive home as a male.

haha good idea Jenni. I have her new wig with the pink and blue ponytails,pity Vivienne's 4000 miles from me she could have borrowed it.

Thank you ladies. I'm sure I'll have a great night regardless of the costume/makeup specifics. I shall of course keep you posted.

Thanks for the offer of the loan wig April. If I'm closer at any point I'll let you know!!

Best wishes everyone! Xx.

Ask the shop if they also have a changing room, because I bet they do. I have been out in public for Halloween once, and had no issue going out when fully done. But, I don't think I would have been comfortable walking out of the shop with my face and hair all done up, but in guy mode.

So, if they have a changing room, change there after the makeup job. Either put the costume on after, or some fem clothes. It does not have to be a dress. If you take a woman's blouse, slacks, and shoes, you will be fine to drive home that way.

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Originally Posted by DIANEF

A number of threads have discussed this topic recently. The general consensus of opinion (if I've read it correctly) seems to be that if you look 'too good' you're pretty much outing yourself as a crossdresser to the world. Maybe you want that, I don't know. Others have claimed it is a 'free pass' to go out en-femme. again opinion is very much divided. I've fantasised about doing such a thing but doubt if I could actually carry it out as my SO does not know of my Cding, (I think....)

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Sooo true!
One of only two times my wonderful but DADT wife saw me en femme was Halloween many years ago where I went as Morticia Adams and she as Homer.
We're almost ready to leave the house for the party and....as I'm walking out to the car she says 'honey....please...stop...you cant go out like that.'
I say 'why....what's wrong'?
her response: 'there is NO WAY anyone is going to not realize that you do this often, not the way you walk in four-inch heels'
Busted.....it was flats for the evening.
;o)

I think some of the logistics of changing, going and coming home may be solved by staying overnight at a motel or hotel. You aren't too sure about in-laws and neighbors seeing you, so perhaps you can just tell the in-laws/sitters that you do not want to drive drunk.

Helen (#10), before I retired I would join the women in the office to watch the guys on the street participating in the "Walk a Mile in Her Shoes" annual event. They would always conjecture as to whether a guy was a crossdresser based on his ability to walk in high heels.

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Originally Posted by Stephanie47

Helen (#10), before I retired I would join the women in the office to watch the guys on the street participating in the "Walk a Mile in Her Shoes" annual event. They would always conjecture as to whether a guy was a crossdresser based on his ability to walk in high heels.

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Yup, yup -and since this was a party with friends, I'm actually very glad she caught that because I'm sure lots of others would have been wondering...like my wife later said in the car 'you HAD to take them off...heck, you walk on high heels better than half the women I know...'

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Originally Posted by Helen 2

her response: 'there is NO WAY anyone is going to not realize that you do this often, not the way you walk in four-inch heels'
Busted.....it was flats for the evening.

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This is one thing that I give the "don't look your best on Halloween because people will now know your entire CD history!" crowd.


Unless one's costume theme is 100% contingent on really high heels (which I'm struggling to even think of something at the moment), then there's absolutely no reason to wear such things out there.

Stick with something like 2" or lower -- or even 1/4" flats.


Besides, they'll make you that much comparatively shorter to others & less likely to stand out, and that much more likely to blend at least a wee bit better. Men (presenting as such) will be wearing shoes that make them up to like 1.5" taller than they usually are -- and leave the heels to the GG's, which will boost them up that much closer to your height. ;)

Excellent ideas and reflections, Helen. If you want to push the limits on Halloween, keep it light, keep it fun. Your idea of swapping roles with your wife is always fun, like she can be the gangster and you can be the mole. One of our most fun party ideas from some years ago, she can be the male magician and you the magician's assistant in appropriate sexy costume, the results of a transformation trick gone "terribly wrong". Hee hee. We made a video to show the trick with her going into the trunk handcuffed dressed in what was her dance recital costume, a black and white bodysuit with fishnet tights, ballet slippers and opera gloves, and I was in a tux rented for a wedding the day before. When I dropped the magic drape, she emerged alone outside the trunk wearing my tux. She turned and unlocked the trunk to extricate me embarrassed to be in her costume still in handcuffs. She then took over while I stood there in her costume, snapped her fingers and made the trunk disappear so I had no place to hide. Having that video of the trick told the story why she arrived as the magician in the tux and I was now her sexy assistant still in handcuffs from the trick. We put the handcuffs on me just as we entered the party and she put the key in a locket on a chain around my neck, still reliant on someone to unlock me. So I just had to enjoy the situation being paraded around as her assistant. To complete the look it was arranged with the hostess to take me back where several of the ladies did an amazing makeup job on me and then produced a wig to put on me before I was allowed to see it. They were so proud of their work and led me out as "one-of-the-girls" back into the party and removed my handcuffs. I feigned complaining to my wife why we could not have just changed clothes back since she was in my tux. She answered that she felt warmer in my tux and she thought I looked just fine after my makeover as her assistant. I didn't know about that but I was enjoying being dressed in just the costume I wanted to be in. Keep it fun and enjoy.