Halloween Opportunity

[Diedre]

As I have stated here before, I have not fully dressed since full puberty kicked in over 50 years ago. While not a big person, with my facial features, I am just not passable.
Anyway, some people we socialize with are having a Halloween costume party and my wife has come up with a plan for me to dress. She has suggested I go as that ugly witch from "The wizard of Oz".
I would have the green face, blackened eyes , green hands, green nail polish and the ratted up black wig. Underneath the black dress my wife said I can be as feminine as I want. So if I do this, I was thinking longline bra. I would love to wear my six garter panty girdle ( split crotch opening for convenience) with black stockings. But I am afraid if someone wanted to see what I was wearing under the dress it might be a give away this isn't my first rodeo. So I will probably go with black stw pantyhose with a black panty. The same goes for high heels. I can easily rock a pair of 3" pumps, but again that might be a tip off. So sadly thinking a one inch heel or flats.

My wife is debating whether she is going to be Good Witch Glinda or leaning heavily to a female Dracula.

For me, my problem is getting up the courage to do this and actually step out the door. I ran it by my cousin who used to help me dress and she told me to go for it, But there is still some anxiety and cold feet on my part. Thinking I am too old for this and don't want to be clocked at this stage in my life.

[Sandi Beech]

I like the good witch - bad witch theme as you have an excuse to be the ugly one so to speak. Of course, finding a good witch outfit might be more difficult than the black witch outfit. I say go for it as you have a good cover using that theme. Get some false eyelashes as well. It will make your eyes look better. Who cares if you are clocked, just own it as just being a costume. I am sure a lot of crossdressers do that at Halloween, but no one will really know which it is - unless you tell them.

Sandi

[Stephanie47]

Just going as an ugly witch may raise suspicions. I think the Good Witch/Ugly Witch would offer more cover since that combo is a theme itself. How high would you expect someone is going to hike up your dress? That's getting pretty fresh or really drunk. Of course, you need black shoes, but black men's shoes? That's crazy. Maybe a black wedge with a two-three inch rise. I have a black wedge of that height for taking evening strolls and more stability than a narrow heel. Go for it.

[Crissy 107]

This sounds like a good opportunity and if it were me I would wear the 6 garter Panty girdle. You have plenty of cover going on and I agree your wife should be the good witch.

[Sabine Janus]

Good witch/bad witch

[Heisthebride]

I understand your anxiety but ask yourself this. Do you really think someone is going to ask what you?re wearing underneath and expect you to show them? Do your friends ask to see you boy underwear or ask your wife to show them her panties. We often let our own heads get in the way of enjoying ourselves. I say go for it and enjoy yourself.

Other option for a couples costume, see if your wife would agree to be a flying monkey or Dorothy.

[OrdinaryAverageGuy]

Your friends will ask what you're wearing underneath. But they don't want to see. You can answer their question with basicly anything you want to say, followed by "you want to see?" The answer will be a big hell no!

Speaking from experience here.

Advice: Every time someone asks, give a different answer. Go crazy. "Frederick of Hollywood's peekaboo sequined crotchless battery powered thong with unicorn attachment. You want to see?"

[Annajose]

Given that your wife is onbard, go with all the bells and whistles, if someone raises your skirt, it will be the person's surprise and the person's problem.

[Jean 103]

Go and have fun nobody's going to ask you to lift your skirt.

If they do cast a spell on them. Or think of some other funny diversion nobody's going to expect you to do it.

I wasn't going to go out this year now I have three parties to attend.

It's a party everybody's there to have fun enjoy yourself.

Love Jean

[AllieBellema]

Do it! Go have fun with this! It's not really their business on what you are wearing underneath so I doubt you'll be asked that. Halloween is a good excuse to dress up as much as you want to for a party!

[StephanieLake]

I say go all in! If my wife gave me permission, I'd jump at the chance. I like the good witch/bad witch idea. If you can't find a Glenda outfit, maybe have her go as Dorthy. It would probably be easier to find a gingham dress like hers than a fancy dress like Glenda's.

[Fiona_44]

Diedre,

Go for it and have a blast!

[docrobbysherry]

Nope. Makeup's a bad idea! Wear a pretty, feminine, witch mask. Then, take it off for drinking, eating and talking.

Folks seeing your guy face will never in a million years think u dress!

[TheHiddenMe]

For goodness sake, do it. Wear the garter belt. Wear the heels. If you're THAT old, what do you have to lose???

There are tons of us who thought the same as you, until we went out and decided we should have done it a long time ago.

Ask yourself. If you don't do it, how long will you be kicking yourself?

Quit overthinking it, do what you want with your wife's support, and enjoy WHAT YOU'VE WANTED TO DO YOUR WHOLE LIFE!

[CharlotteCD]

Just remember that people won't suspect for a one off, they'll wonder if you dress femme two years in a row, and they'll know you dress if you do it three years in a row...

[alwayshave]

Diedre, I would never ask someone what they are wearing underneath their clothes, why would your friend group. Just dress and enjoy, and stop over thinking it.

[Diedre]

Thank you all for the encouragement. I am going to dress the way I want and not worry and just have fun with it. My wife found a Good witch Glinda dress at Amazon for her and me a pair of 2" ruby red pumps. Plus I decided to ditch the pantyhose and wear my panty girdle with black stockings. I agree with those that said others shouldn't be asking or lifting my dress.

I will post an update how things went after the event.

[Jillcder]

Diedre I love that your wife told you to be as as feminine as you want under your dress I say go for it I would definitely go all in especially with my wife?s permission. Enjoy the party.

[Krisi]

One reason I don't go out dressed as a woman on Halloween is that I wouldn't be able to dress as I want to without giving away my "hobby".

What "normal" guy has a well fitted bra and "real" silicone breast forms? Hip and butt padding? A nice wig? Well fitting women's shoes?

Going out with a party wig, rolled up socks for boobs and no hips or butt just doesn't excite me.

[Aunt Kelly]

As I have stated here before, I have not fully dressed since full puberty kicked in over 50 years ago. While not a big person, with my facial features, I am just not passable.

I love the witch costume idea, but I must point out that Halloween costumes are just that, costumes. If it is your desire to go out in public, presenting as female, do it. You don't need to "pass", and you don't need to use Halloween as an excuse. Be who you are... or don't. It's not a requirement to present in public, but if that's your desire, know that it can be done without "passing".

[Vickie_CDTV]

Wear the girdle and stockings if you like. If you are wearing a bra anyway, a girdle shouldn't be any more or less suspicious.

You might want to wear a slip underneath your costume, for both practical reasons (prevent showing too much from see-thru or if your skirt gets caught on something etc.) It also adds to the vintage-ness of your outfit. It would also add another "barrier" if someone wanted to see what is underneath (as unlikely as that would be.)

[JenniferMBlack]

Elwhat kind of group is this you are socializing with? I would highly doubt anyone is going to ask to look under your dress to see what you are wearing. Or maybe I have the wrong friends as not one has ever asked what I was wearing under anything.

Also she didn't wear overly high heels so go with the costume which is like Mary Jane shoes with a small heel. I would suggest your wife also go as a character from Oz then you won't seem so much like you choose a female costume because it is female.