Halloween cross dressing stories

Added: Markeita Stoughton - Date: 17.04.2022 21:36 - Views: 45490 - Clicks: 2553

October is here, and we all know what that means! Even still, when you know that dressing up is more than just a costume, it takes a staggering amount of courage to go through with it. I thought about giving it a go for many years, and about 10 years B. And I have John McCain to thank for it! The year was I had broached the idea of borrowing some clothes from my wife and going as a woman for the annual party we attend a few years prior, and she thought that was a dumb idea.

So what was so special about ? Election year! And I had been struggling to come up with a good costume. As we were discussing it before bed, I mentioned what my friend had said. It was a dark blue, padded bra, which was perfect. Could I have worn a shirt underneath?

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Luckily, she also had pair of nearly opaque nude tights. Even she had to admit, that looked much better than hairy legs sticking out of a skirt. But I still needed something to wear on my feet. I dug her black high-heeled boots out of the closet to see if they would fit. The next day would be a busy one, because I still needed to get a wig.

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Ulterior motive alert! I also picked up a pair of clip-on earrings. They were kind of ugly, but it was all they had. Also, on the shopping list: little Halloween cross dressing stories glasses, Nair, and a toy rifle pew! To fully sell it, I also played on recent reports that Palin had been spending crazy amounts of campaign money on clothes by attaching fake price tags to all my clothes. After a quick dinner, because I could barely eat, I went to get ready.

But it did the job. The hard part over, I got dressed up and then asked to borrow some make up. She was reluctant, for hygienic reasons, to let me use her eyeliner, but was ok with mascara. So I did the best I could to lay it on thick enough to look girly. Getting the wig right proved to be much more difficult than I had anticipated, but once again: wife to the rescue. She got the required height by balling up some brown tights and pinning it under the top of the wig. One more problem, how was I going to carry my wallet and phone? She asked if I wanted to borrow a purse. So she gave me a small evening bag, which I also used to bring lipstick and mascara in case a touch up was needed, and one of her necklaces to help hide a nick on my chest from the hair removal process.

Now it was time to leave to the party.

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As we pulled into the parking garage, I was suddenly plagued with doubt — what the hell was I thinking? Oh well, too late now. Then she did a double-take and her jaw dropped! She honestly thought I was just some random woman! I felt elated. All night I got compliments on how much I looked like a woman.

Me being me, I took it as disapproval, despite all she had done to help me with this costume. All too soon, the evening came to an end. For weeks afterward, I was getting comments from friends from the party about what a good woman I made. At least something good came of that…. How many of you have gone out en femme for Halloween? What was it like? Would you do it again? I want to hear all about it! I am a very shy and keep-to-myself man. Playful, sexy, cute, girly, silly, loud, daring, etc! Normally this girl is very much kept in the closet…well, this girl went tempor My wife knows I dress, but has always said she wants nothing to do with it.

She could see I was unhappy, and when she asked me why I plucked up the cour You wear a beautiful outfit, are full of charm and poise and a handsome gentlemen stops to talk with you. Does it end in joy or disappointment? Stephanie discovered her crossdressing desires early on, and has been able to share them with her wife who accepts her woman inside.

I could be wrong, but I got the feeling that the people I interacted with on this trip fell into two camps. One was very cheery and seemed really excited to be interacting with a crossdresser. The other comprised of people who treated me like any other person, not really paying m I had medium length hair so they just believed I was a girl. I had to change, but since she wanted to keep up My journey probably started like so many others. I was nine years old and it was the s. I was never into the boy things, such as motorbikes and sports, and always wanted to hang around with the girls or just sit by myself and admire how they dressed.

It was a fascination I attended a halloween party this week. Since I always go enfemme, that would not have been much of a costume. I went as catwoman. Not so convincing when the costume does not hide my man-belly, but it was fun anyway.

I look forward to it every year! Love getting dressed up. Alexis, What a great story! My first time out en femme was Halloween sixteen years ago. I was recently divorced after 22 years of marriage and I had been getting seriously deep into allowing my feminine side to flourish as never before.

I just decided that I was going to take the opportunity to get out in public as my femme self when I could get away with it. I already did have all the undergarments and stockings … ». You look great! Anyway, good luck with whatever you decide to do.

Since were relatively the same size fit was not a problem…evening ended with folks at the party chanting for me to do a strip tease…that was some evening. Meet crossdressers, make friends and share your inner women with others. Crossdresser Heaven has a vibrant community, with more than 35, members and dozens of daily posts and crossdressing topics to explore. Crossdresser Heaven. A collaboration between Crossdresser Heaven and four leading retail providers serving the crossdresser and transgender community. We may receive a commission for purchases made through links to our sponsors.

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If you have a website, please consider placing one of our banners on your website. Toggle. The following two tabs change content below. Bio Latest Posts. Alexis "Lexi" Moon. Been crossdressing since age 5, but just this year finally accepted that my obsession with dressing in womens' clothes is ultimately driven by the fact that I'm happier presenting as a woman. Still trying to figure out what that means, but just trying to enjoy the ride for now! You can find me on all the Halloween cross dressing stories streaming platforms.

DM if you want to learn more! Latest posts by Alexis "Lexi" Moon see all. Share this. Related Articles. Letting your inner woman out! Oh, What a Disappointment! Andrea Miles January 25, January 21, Crossdressing Experiences 7 You wear a beautiful outfit, are full of charm and poise and a handsome gentlemen stops to talk with you. Introduction to Stephanie cdheaven January 22, January 21, Crossdressing Experiences 10 Stephanie discovered her crossdressing desires early on, and has been able to share them Halloween cross dressing stories her wife who accepts her woman inside.

A Life Born from Moments of Pain. Notify of. Inline Feedbacks. Diane McG. Pippi Long. Tricia Lynn. Reply to Halloween cross dressing stories Lynn. Tiff Any. Trisha Kobichenko. Our Community Enjoy some girl talk Meet crossdressers, make friends and share your inner women with others.

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Halloween cross dressing stories

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A Cross Dressed Halloween