Halloween Crossdressing

Hello everyone. Mostly hope to share this with other wives or girlfriends who have submissive males in their lives. It's getting clsoe to Halloween and there IS preparation time for teaching males how to look their best when done up for Halloween as a woman. Time to start is ASAP.
What success have you had doign this in the past? And it doesnt have to be YOUR husband or BF, Talk to other women who might like the idea too. The teenage GOTH community is very much into this so that could be a place to start.
It has to be very FUN for the male so he will ENJOY the experience and want to do it again, and hopefully, more often.
Any ideas anyone would like to share? Please post here and we canhelp everyone interested.
Have FUN
JackieSCToo @ aol
deleted deleted
19 Responses May 28, 2013

I've been dressing as a woman since I was able to start going to the parties. This past year a French maid. With frilly panties. Everyone love it and getting my bottom smacked was an extra treat.
I wish it came more often so I could dress more outside

Why do you want your husband to wear a dress even as Halloween costume?

How wonderful it is that you're offering help to other women. I believe there are a lot more women out there who want to do this with their men than we realize

Yes I believe that is very true. It certainly is in my case! Lol

I so wish someone like you would help feminize/emasculate me into the total limp wristed fairy I know I am!!! I need to come out so that I can be totally humiliated in front of friends and family. I'm a panty waist queer that loves to suck guys *****. I just can't help myself!!!

Well as I said below, Halloween SEASON starts with Opening night of the local lIVE Rocky Horror stage show. As usual it did not disappoint and neither did I. As my related stories detail, I annually change my MAIN costume and freshen up the others. This year's theme was Art Deco (last year was Steam Punk), so a sexy black Flapper dress (short so my ruffled panties would show occasionally) was the obvious choice. I added a long fluffy Purple boa, forearm fishnets, back seam wide gage black, back-seam fishnets over off-black pantyhose. Finally my new pointed toe black pumps with 4 inch heel covered in silver metal dots. I used my old short wig that matches my beard. A short trip to the Charming Charley costume jewelry store in a new short skirt completed the look and gave the male clerk a nice thrill (looks like he'll be my date Halloween night). What a kick when my friends & I showed up first at a gay-friendly restaurant to a chorus of whistles and applause.

After dinner, we headed to the theatre where they were waiting to see this year's costume choice. Some of the cast said that they look forward to seeing us in the front row, as we are like Cheerleaders to get the rest of the crowd going. I had a male & female cast member sitting in my lap during part of the show, after the show were hugs & kisses from both M & F. It only goes to prove that if you carefully choose your outfit for the "**** with class" look and pay attention to complete follow-thru, it will result in many *** pates and hallway caresses that got me ivited to the cast party and inch by inch attention the rest of the night.

My trick was certainly a mutual treat. Thanks again for starting this story

Thanks for the kick start! I'm going to work on Halloween dressing because of you.

I'm so proud that I've turned into a pantywaist sissy and let others use me as a ************ toy rather than a real person!!!!

I so loving *** more n more

the first time I went out in public dressed up as a woman was Halloween. both my friend and I were dressed up by his older sisters. I loved it and still do

I love the way you think. My favorite holloween was the one I was full fem for in front all my male and female friends.

It's more than just Halloween for me. Everyday is Halloween for this CD panty boi!!!!!

I just added a photo in my Alter Ego album of me & Frankenfurter from last year's Live RH show to give you an idea of typical outfits. He/She was a full speed ahead dynamo both on-stage & "off"
TTFN got to go plan this year's outfits

Just to clarify. It is NOT the RH PICTURE SHOW but the original LIVE Rocky Horror Show that first came out on a London stage that the Picture Show is based upon. Frankly, the few times I've gone to the Picture Show even with the live actors in front of the screen, it gets boring. Google ROCKY HORROR SHOW and go to the links that DO NOT have the term "Picture" attached to it. There are links that will give the dates and places across the country that have been given a license (and paid the fee) to produce a live stage show. You won;t regret it.

I now have a growing group of friends (M & F) that go with me every year to a LIVE PLAY of Rocky Horror. It usually runs Fri & Sat for 3 weekends + Halloween. This is a :"Safe" way to have fun crossdressing because "Everyone" is doing it. As opposed to just watching actors in front of the movie. The live show we attend changes themes each year so you need NEW costumes Lasdt year was "Steam Punk" Can you imagine.. But it was one of the best ever. So , as every girl knows, you can't wear the same outfit 2 nights in a row so LET"S GO SHOPPING. I take a female friend as my "Super Shopper" (so I don't get ripped off) and we go to Fredricks in the mall and try on corsets then Charming Charlie and buy costume jewelry, then I spring for lunch. I will be writing a story this weekend about how I get ready to go shopping as its much easier to try on female clothes IF you are already wearing some. So I must go now and figure what sexy, slutty outfit I can put together to go downtown and walk 3 blocks to the costume shop and look so hot that you just don't care that your beard is giving it all away. Visit my Alter Ego photo album for some recent year RH outfits. So girls.... Let's go shopping.

Great idea, and would be easiest timing for women to take 'control', and challenge husband's, boyfriends into dressing feminine! Suggesting ideas, like I think you'd make a cute french maid! (Or school girl, cheerleader, or even a sissy, if you could get them into a frilly sissy dress, of course with reassuring, that you would keep their little secret?) Any of them would definitely give the woman the upper hand, and power, from then on out. Especially, if guy gets 'excited', (most probably will) can always hold over them, to a degree. ("Well, if you don't 'obey' me, I'll just have to tell the whole world, what a sissy you really are, and how you LIKE dressing up pretty for me, and can't wait to get into your pretty clothes for me, whenever you come home".) You can also use a reward scenario, like, oh, it would turn me on, to see you in silky panties! What, aren't you 'man enough' to not worry about what others may think? I'd love it for a woman to 'make' (or ask, with a sexy voice) me to wear panties, under my reg. clothes, and when got to mall (telling me, oh, it would make me hot, knowing what you were wearing for me, and will be our little secret) not mentioning details of exactly where you were going to shop, then going into lingerie dept. and holding up pretty panties, saying oh, these are pretty honey, what do you think? Here, feel them, aren't they sexy? (If guy balks, or backs away, could whisper in his ear, don't fight it, or I'll hold them up to YOU, and tell you how sexy you'll look in them, for me...And make you buy from salesgirl & tell her they're for you!) They'd probably turn very red, and know they'd best not fight you, or alternative is getting way more embarrassed!

Because, I am also a crossdresser. Str8M, & 'Lesbian', for the right GG. (Genetic Girl).

Maybe it will be exciting when all your men will wear female dresses and all women wear male suits and then all people would enjoying sex together... What about the idea?

Hi Jackie,I loved your story,I do cross dress at home,but I really want to go futher and step out in full womens clothes...great way to do it.thanks

Jackie, if you haven't check out my Halloween Wedding photos my Dee and I did this two Halloweens ago. What a blast we had!

I love this idea to introduce guys to feminization

Jackie...You are Awesome! The More men and Boys that are Feminized, the Better Off the World will be!