Halloween

[Tj76]

So I'm excited my wife wants to dress me as Dr frankenfurter this year so I can dress up and have fun! Does anybody else have plans to enjoy this awesome holiday?

[1Ladyjade]

My plan for this year is to dress as Columbia. I dressed as Frankenfuter and went to a show. That was fun.

[Suzy]

I will probably either be a bride or a playboy bunny!  I’ve done both of those in the past.  Always fun!

[CanuckGirl]

Sounds great ladies! Recently I just found out the gay bar I sometimes go to is having a Halloween party.

I really don't know what to do this year, I did Cleopatra last year and got lots of compliments. What I'd love to do the is the outfit Kate Capshaw wore in the night scenes in the Raider's movie, second one in the series, but no one makes a costume and I don't know if I have the ability to make it myself.

Otherwise another a legendary beauty, but I can't decide!
Amy

[Sara69]

It’s funny as a kid I dressed up a couple times as a girl, not knowing 10 years later how much I would like it. I think I would look good in a maid outfit. Don’t have the figure for playboy bunny.
Hugs
Sara

[CanuckGirl]

Slightly off topic here, but it's still about Halloween.
Back in school, and I'd guess it was grade 7 or 8 and we there was a dress up Halloween party at school. I cannot remember what I wore but I'm sure it was something my Mom put together for me, however this isn't about me.
There was this very pretty girl dressed as a ballerina that I was quite impressed with, and then my surprise when I realized "She" was one of the other boys in my class!
Knowing what I know now I have to wonder what happened in his life as I'd bet has continued to dress up at some point. This is like once bitten you have it forever!
Amy

[Cdmich49]

Hi everyone. Halloween is a blast as a crossdresser.  We get to let our hair down so to say.  Went to a local straight bar as Elvira two years ago won second place. Tough crowd!  Had another costume ready last year as a Dominatrix. Had a flu bug and did not go.  Key thing on the Elvira showing I saw many friends who knew me and did not have an issue with me being femme dressed. One friend actually wanted to take me home with him.  Hoping for the Domm costume this year at a local gay friendly bar.

[panty_chap]

That's funny, I dropped by the website tonight to check out costumes. Something slutty would be fun but we never go to parties so it won't happen. :-(

[doozer2019]

I'd be happy just to dress as a female. Maybe that's a way to start to introduce my wife to me dressing...have her doll me up for a Halloween party...hmmmm.

[CanuckGirl]

I'd be happy just to dress as a female. Maybe that's a way to start to introduce my wife to me dressing...have her doll me up for a Halloween party...hmmmm.

 Well I know a couple of people, dressers of course, who have done just this very thing with success. Not only with their wife, but also one good friend started doing this to break the ice with their grown up kids.
 As with so many other things it depends on the person involved, some women seem to be much more receptive to this than others. If you drop some hints to her about doing this and see how she reacts that will help you judge.
 Hope it goes great for you!
 Amy