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Pick Your Crossdressing Costume This Halloween

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(@cdh)
Famed Member     Seattle, Washington, United States of America
Joined: 13 years ago
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The Crossdressers National Holiday is just around the corner. That's the day when crossdressers around the world can dress as they please without fear of being outed, and go where they want without fear of ridicule.

Of course, if you're afraid that someone will out you it's always good to follow a few crossdressing halloween tips, like wear a woman's costume don't go in your everyday skirt and blouse. Being in costume is less likely to tip others off.

If you're looking for a few more ideas for your crossdresser halloween costume a quick browse through the local Halloween store will show you what's hot and available in your size.

Two great places online to find sexy woman's halloween costumers are Fredericks of Hollywood - which has among others the Sexy Maid Outfit shown to the left - and Amazon, which gives you free shipping on some outfits.

This is also a great time to get your spouse involved. Even if she is not normally supportive of your crossdressing, it can be a fun tension-free way to go out together in your femme role. Let her doll you up and perhaps go a little over the top with your outfit and makeup.

What are you going to be doing this Halloween?

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Guest
(@Racquel_Lynn)
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Joined: 15 years ago

I remember when I was a kid and trying to go dressed as a girl for Halloween and was always disappointed in the outcome. Sure, I still had fun trick or treating with my friends and brothers, but when I said I wanted to be a girl for Halloween, and though I knew in my heart I wanted to really be a girl, I had no female clothing of my own, no makeup and no knowledge of how to apply it, etc., so I was at the mercy of whatever anyone threw together on me. The few times when I was younger and went as a girl for Halloween, it was done as funny and a joke and the dresses I had to wear did not fit right and was not the kind of style I liked either, my mom had a few wigs laying around that we'd play with sometimes to be funny, but my mom never wore wigs. They looked ridiculous, but I was always given one to wear with my girl "Costume". And the makeup was never pretty.

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(@Racquel_Lynn)
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As I got older and grew my own long hair and was in bands, during the 80's, I could get away with wearing some feminine clothing and some makeup and have my hair done everywhere I went and no one knew I was crossdressing/transgender. lol
Of course, I was not wearing dresses or skirts, but you could wear quite a bit of feminine looking to obviously womens clothing back in the 80's and it was the "Cool Rocker Look". You could be both feminine and hard edge at the same time. (To this day I still love the 80's rock groupie look. lol) Before I ever came out as Transsexual to anyone, the 80's was such a great time for me in many ways. I was still in the closet, but I could still dress to a greater extent to that which met with my personal inner identity. Girls would always love to play with and fix up my hair. Sometimes they would want to French Braid it and was afraid I wouldn't approve of anything that feminine, but I always welcomed them to fix it in any way they wanted as long as there was nothing permanent that couldn't be put back. (Could not cut it short or give me green mowhawks, etc. lol)
Girls always would let me borrow their clothes. I wouldn't even ask them, they would just say "I think this would look great on you, why don't you wear it tonight. (Zebra Spandex, a blouse, a sexy but rocking scarf, etc.)
Girls loved to do my makeup for when I played out with the band or just going out. Sometimes they would be worried that the makeup would be too feminine and I wouldn't like it. Occasionally, I would have a girl that didn't do my makeup well, but usually, whoever was doing it did a really great job and I loved it. Quite often (once again BEFORE I came out) girls who would be doing my hair and/or makeup would bring up that they would like to make me up like a girl one day just to see how I'd look (they brought it up, not me) Of course, I always wanted to, but would try not to give it away that I wanted that more than they did.

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(@Racquel_Lynn)
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Sometimes they would say "I would really like to do your hair and makeup like a girl one day to see how you'd look, but you probably wouldn't let me do that, would you?" I would always replay by saying "Hell. I don't care, why not, it would be a lot of fun!"
Once in a while a girl would try to make me look like a girl and it looked ridiculous. Some girls will make you look like a man that is trying to look like a woman or they give you the theatrical look like a drag queen would wear on stage, which is fine, just not the look I was after (and it's hard to tell the girls what you are after without outing yourself). But for those that did a really good job and made me look and feel really sexy, WOW! lol we had a lot of fun. If it didn't look good, I would go wash it off when we got done, but it it looked really good, I would leave it on and even go out with the makeup and hair done. Every now and then, when girls would make me up as a girl, they would ask if they could dress me up. Usually, it just ended at hair and makeup, so I loved the few times I could do this and it was their suggestion. They would fix me up and have me put on an outfit, a dress, a skirt and whatever else just so they could see their work completed with the outfit to see just how much they had pulled off making me look like a girl.
The disappointing thing about that was when I was looking really good with the hair and the makeup and the outfit all together, I was not out yet (was even in the closet to myself to an extent, but I still always knew in my heart and the back of my mind) So I would still keep the makeup and hair done and go out in public, but I would not wear a dress or skirt out in public............
...........................UNLESS IT WAS HALLOWEEN!!!!
THEN Halloween started to become really fun for me.

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(@Racquel_Lynn)
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When I met my ex wife, I had dressed up for Halloween on our second date, borrowing some of her clothes, wearing some of mine and adding a few things I bought in the Halloween isle. (before coming out to her, or anyone)
After I had come out to her (Before we were married) I decided to try to make a trial run and spend the day (Halloween) dressed as a female, and told her that I wanted to look as real as possible. I wanted people to actually believe I was a woman.
She made me up wonderfully. I had to work 2 jobs that day and people I worked with everyday thought I was a real female and did not recognize me (until, as most of us experience) I opened my mouth to talk. We all went out to a club that night after the second job and had a great time. I actually got to spend a full day, 2 jobs and a night out on the town, with eating out during lunch and a couple of stops at stores along the way, as a female. I was dressed and looked great and felt great, I was comfortable, and most of all, I FELT LIKE ME! Everything felt right more than it ever had before in my life. That, more than anything made me realize that I couldn't fight it anymore and I had to start coming out, so I did, slowly at first.
A few months later, a local radio station was having a contest....a DUDE LOOKS LIKE A LADY CONTEST. I got fixed up the same as that Halloween and went. I Won the contest and got to travel to an Aerosmith concert and got back stage to meet the band , who are a few of my lifelong musical heroes!
It wasn't long after that that I started getting the courage to go out in public dressed up on a normal day when I had no other excuse for crossdressing other than "This is me, and this is how I like to dress". It was scary at first, but didn't take long to be comfortable, the more I did it.
Halloween is a great springboard for crossdressers and all trans people.

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(@Racquel_Lynn)
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but we had fun didnt we make up times is my problem is it unacable in socity to go to cosptogly school
not noing what to do

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(@Racquel_Lynn)
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A few years back, when I still had my tailcoat and long silvery hair, one of my favourite looks was to do Science Centre hair (fluff my hair straight out with hairspray) and do super green and grey corpse makeup. Some cockroaches drawn on an old shirt crawling around on me added to the gross factor. I'd arm myself with a baton and terrify small children at our door as a dead conductor. Some of the younger ones would run screaming but the older kids liked it.

That would be a crossdressing costume for me now. I don't know if I could do it any more.

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(@Racquel_Lynn)
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Joined: 15 years ago

I still don't have a concrete plan for where I am going this year. I do have my costume worked out. I am going to be a biased referee. I think I should be sexy enough to get away with at least a few bad calls.

My first time out was at 16. I had staged an argument with my gf about pants versus skirts and so she decided I should wear a dress for haloween. Then after I was dressed she announced we had to go to our school homecoming game. The next year I was a zombie prom date.

Over the years I have done a variety of costumes and every year now it let's me ease people into the idea of who I really am. Some other more traditional costumes I have done include: witch, pirate wench, and princess. I still haven't been brave enough to go as a queen or fairy yet, maybe next year. 🙂

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(@Racquel_Lynn)
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I'm so excited. Just came out to my wife a week ago. Of course, the initial shock and horror happened at the revelation, but things are getting better everyday. She's now let me order a pair of Pirate boots and other assorted shoes so long as I get her a good costume and shoes too. Well, since I was getting the Pirate boots, I reasoned it would only make sense to get an accompanying Sexy Pirate costume for me also. 🙂 We'll just have to see if she'll actually let me wear it outside the house this year. I don't want to push things to fast for her, especially since she hasn't seen what I looked like dressed, well, as ME!
We've been married for over 18 years, so, I do acknowledge she needs time to adjust. I'm just giddy though. I want to show her what I look like as a normal, everyday woman, not just in a costume.
Ahh well.....luv and hugs to everyone.

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(@Racquel_Lynn)
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I just finally came to terms with my need to be a women. I love to dress and understand its who I am. I no longer am enbarrassed with myself and I will express who I am. I hope to dress up for holloween.

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Admin
(@cdh)
Joined: 13 years ago

Famed Member     Seattle, Washington, United States of America
Posts: 1461

Wonderful love! I hope you have a great time at Halloween!

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Guest
(@Racquel_Lynn)
Joined: 15 years ago

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Posts: 95

Enjoy the experience girl

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Guest
(@Racquel_Lynn)
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Joined: 15 years ago

Went as a pretty witch, it was great to do my make up first thing in morning and put little dress on and my favourate heels I spent the whole day and night at a pub then a party and most people were shocked when they herd my voice, your a man? They asked I thought you are a girl. Best day of my life and now have couple of girls who want me to go out dressed with them shopping and lunch.

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(@Racquel_Lynn)
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i had a wonderfilled time going as a fairy princess i was awed at the looks i got .maybe it was the booze?

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Guest
(@Racquel_Lynn)
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i went as a flight attendent (: it felt great to go out in public as what i felt to be normal. wish i could do it everyday. but i still have dreams right

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Guest
(@Racquel_Lynn)
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i know what you mean, its scary to come out when u worry about everyone else..

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Guest
(@Racquel_Lynn)
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Joined: 15 years ago

Im planning on dressing as Dame edna this year and have a couple of sales girls at my local value village ( a local second hand store)excited about helping me put the outfit
together.
Maggie

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Guest
(@Racquel_Lynn)
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Joined: 15 years ago

sexy maid i just got janitors job at work but i cant dress feminine except my panties i get to clean girls bathroom is threre tips for cleaning so i can do a good job i would especialy like the female reponses here and is there places to be a maid conspisocly

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Guest
(@Racquel_Lynn)
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Joined: 15 years ago

I have 5 french maid uniforms! I just got a new one this past Halloween and wore it to a party. I love wearing it! I feel so sexy in it !

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Guest
(@Racquel_Lynn)
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Joined: 15 years ago

I realy love the maid look I got to have on girls

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(@chrisj5032gmail-com)
New Member     Sheffield, South Yorkshire, United Kingdom
Joined: 6 years ago

I love to dress up in a sexy air hostess uniform this Halloween will be such fun.

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Posts: 11
Lady
(@lunawing)
Active Member     California, United States of America
Joined: 5 years ago

I want to dress as a female Pokémon trainer but I am scared of my parents finding out

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Posts: 61
Lady
(@stephaniew194)
Trusted Member     Boston, Massachusetts, United States of America
Joined: 8 years ago

French maid. That would be my choice in an instant!

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