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It’s Halloween – Do you Know How To Crossdress?

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(@cdh)
Famed Member     Seattle, Washington, United States of America
Joined: 12 years ago
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So I’ll admit it – I go a bit crazy around Halloween. I just can’t help getting excited by the thought that so many crossdressers will be out expressing their true selves in public! It’s almost a crime that so many of us only get to do this once a year, but boy when that times comes around – watch out!

As I was writing this post my beautiful wife popped her head in to see what I was doing. She thought it was strange that I would ask you – do you know how to crossdress? Since, most of the readers of Crossdresser Heaven are crossdressers, presumably you would have some idea how to crossdress 🙂 Questioning your ability to dress en femme was not my intention. Rather I wanted to ask – Do you know how to crossdress at Halloween? In some sense it’s easier to crossdress at this time of year, but you can’t rely on everything falling into place at the last minute. A successful Halloween crossdressing adventure requires at least a little bit of planning.

Have you planned your crossdressing escapade?

Do you have your outfit all planned out? Have you coordinated your makeup with your outfit, and checked to make sure you’ve got the perfect earrings to go with it? You can’t just wear any old jewelry with a sexy nurse outfit. Some outfits demand a certain kind of shoe. Whether it’s a spiked stiletto boot or sexy white pump you’ve got to be prepared.

A Halloween Princess

I’ve always wanted to dress up as a princess for Halloween. A princess like in the Disney movies in a flowing ball gown. To dream, if just for one night, that I was a

beautiful damsel living in a tower. With each day filled with sunshine, signing birds and elaborate outfits. If you’re planning to go as a princess, well – that would require a bit of planning. Your jewelry will need to look as expensive as your outfit. This is also the perfect time to try a new updo – it looks extremely sexy when you’re in a formal dress.

So, who are you going to be this year?

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Guest
(@Stephanie)
New Member
Joined: 15 years ago

I am a 41 yr old male crossdresser, and I love Halloween. This year, I have this sexy short dress and a pair of black pumps. I will be one of the Spice Girls for this Halloween.

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Guest
(@Stephanie)
New Member
Joined: 15 years ago

As an MTF transsexual the thought of cross dressing doesn't involve woman's clothes since that is how I dress daily. It brings out memories of my old life and going male for a night, some what of a mixed thought emotionally for me.

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Guest
(@Stephanie)
New Member
Joined: 15 years ago

I haven't dressed up for a party in awhile so this year I am going a a "Hooker".There is sooo many other things to dress as but can't resist wearing a short denim skirt and crochet black fishnets over silky tan pantyhose and High heel black boots.

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Guest
(@Stephanie)
New Member
Joined: 15 years ago

Nothing like dressing up as a women and going out on the town . I love to get all dolled up as a women and have fun . I just came out with it !!

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Guest
(@Stephanie)
New Member
Joined: 15 years ago

I need to learn how to do my make-up . I love to jump at the chance to dress as the sexy woman I am .

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Guest
(@Stephanie)
New Member
Joined: 15 years ago

I love my crossdress is a very sorte skirt and lowe cut top that my tittes is out thair . a gaterbeilt that the hook is shoring . A brit lip stiks like red

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Guest
(@Stephanie)
New Member
Joined: 15 years ago

I am dressing my little boyfriend as a FRENCH MAID He is so thin and small and 61. He is very cute as a women and he loves wearing my petite dresses

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Guest
(@Stephanie)
New Member
Joined: 15 years ago

Halloween was the first time I went out as a women what a thrill . Then when I was in las Vargas I found just you they helped me dress and I went out again now I want to go out more but can not find any place to go I live in east central man any help ?

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Guest
(@Stephanie)
Joined: 15 years ago

New Member
Posts: 1

Joann meant to say east central MInnesota

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Guest
(@Stephanie)
New Member
Joined: 15 years ago

How do you crossdress.

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Posts: 1
Guest
(@Stephanie)
New Member
Joined: 15 years ago

I love my french maid outfit! I wear it every year! But I'm a Nurses Assistant so like to find a cute Nurses uniform!

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Posts: 6
(@cdjoanne)
Active Member     Fort Wayne, Indiana, United States of America
Joined: 4 years ago

Every Halloween I wear a female costume, nurse, stewardess, wonder woman etc., so this past Halloween I just wore my blue, long sleeve, velvet mini dress with super shiny suntan pantyhose, a bra, panties, waist cincher & my blue, four and a half inch platform stripper heels. I had my toes & long acrylic finger nails polished bright red, I pinned my hair up in a bun, I had my eyebrows freshly plucked super thin with a high feminine arch in them, I wore large, over sized, blue hoop earrings in my pierced ears, blue bangle bracelets, a blue strapped women's watch, a gold ankle bracelet that read sissy on my right ankle, a gold necklace with my name on it, Joanne, full makeup, perfume & I carried a blue clutch bag filled with my makeup. After every Halloween I hear people talking about me because I always dress as a woman, I figured this year I would let them all see the real me. I called off of work to get ready & I showed up at the club where the company party was being held about an hour early. I had a seat at the bar as people started coming in, no one even recognized me, it was not until I over heard some co workers talking about me not showing up that I went over to them & told them who I was. They were speechless, a female co worker took me by the hand & led me around to everyone telling them who I was, our human resources lady asked me if I would be coming to her office to fill out the proper paper work for a sex change, she looked like she was going to fall over when I told her that I would be in her office first thing Monday morning. I couldn't believe it when one of the guy's I work with started hitting on me, I danced with him to a slow song & while we were dancing I leaned in & kissed him on his lips, he didn't pull away instead he put his tongue in my mouth & I let him. After the song we snuck out to my car where I performed oral sex on him then returned to the party.

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