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The Most Wonderful Time of the Year

by mattie on October 18, 2010

In crossdresser and transgender circles halloween is often referred to as a favorite time of year. It’s not so much that a CD or TG person is more into ghost and goblin costumes than the next person, but that for many people it’s the only day of the year that they can dress how they really want to. For many people, it’s their first experience being able go out in public and not risk being “outed” as a crossdresser or transgender person, and for those with significant others it can be a good time to share in the joy of dressing up.

If you’re thinking of crossdressing for halloween here are some tips to consider:

- First, don’t be afraid to consult your wife or girlfriend for advice. If you’re going to dress as a girl, it is going to be really helpful to have their outside opinion on which halloween costume flatters your figure, and any tips on applying makeup (especially if you aren’t experienced doing it). Don’t be afraid – TONS of people are crossdressing for halloween, it’s your time of year to shine!

- Find a great crossdresser halloween costume. There are tons of great options out there now days for crossdressers. Go to the local thrift store (they won’t bat an eye normally, but it’s especially normal in October for people to shop for all kinds of clothing), check out sites like Amazon, or Ebay. You might even be able to borrow some clothes (with permission!). There are lots of ways to be resourceful and find a great costume.

- Spend some time practicing – you’ll have more fun if you do more than just find a great costume! Leading up to the big day you can spend time practicing how to make your voice more feminine, how to walk in a more feminine way, and work on your female persona. Don’t miss this opportunity to do the things you’ve always wanted to do in working on your voice, or the way you walk, or something else.

- Don’t forget about safety. Even though crossdressing is popular and widely accepted on halloween don’t forget to be safe. Think like girls do, and go out with at least one other person. Besides, it can be a lot more fun if you can get your wife or girlfriend to join in on the fun and go out too. Going it alone is never the safest option.

- Don’t forget to have a good time. Even though it might make you nervous, try and relax and have a good time. Don’t worry if your costume or outfit isn’t perfect, or if you didn’t get your makeup perfectly correct – tonight is about creativity and fun.

Are you planning on going out crossdressed for halloween? I’d love to hear your tips, stories, or advice about it! Comment below.

Image Credit: riptheskull

{ 3 comments… read them below or add one }

Brian Black June 29, 2011 at 1:14 am

Halloween! The best holiday ever, especialy if it falls on a friday or Saturday. The first time I crossdressed in public was on Halloween 2009. I coaxed my friend to go to a gay club for a fantastic night out. My wife helped me with a dress, makeup etc.. Nothing happened on a sexual level; it was all 100% fun and laughter. I had such a great time chatting with other patrons from fashions to music. It seems that we just got there and it was time to leave. Even at 1:30AM, there was a line up outside waiting to enter.


Jeanette September 14, 2011 at 5:18 pm

I certainly agree that halloween is a great time to crossdress openly, even being able to do so around friends that would not otherwise accept it. The first year I tried it had its ups and downs and I definitely learned a few things along the way.
Here are a few tips I’ve come up with.
1.) Be realistic. Reactions are going to be all over the map, mainly light hearted, but your friends will likely poke some fun when you show dressed, whether they have any notice or not.
2.) Some people will see through it. I learned this one the very first time I did it, some people are going to see that this isn’t your first time dressing, but they’re unlikley to be confrontational about it.
3.) If you need support, ask for it. I really struggled with it and decided I had to talk to at least a couple of friends about it, tell them how I felt. They were awkward conversations to have but it certainly helped knowing that I could count on them to understand.
4.) Nobody takes it that seriously. If things go bad, or feel awkward, it isn’t the end of the world. Just relax and have fun.
5.) Share your experiences with others. This will help other cds have positive experiences on Halloween (and other days) as well. :)
6.) Last but not least, plan ahead about using public bathrooms. The first year I did it I was afraid to use the men’s room at the bar we were at and by the end of the night I was losing my mind!
Anyway, these are a few tips so take them for what they’re worth. :)


Becki December 25, 2011 at 12:41 pm

Great advice. Can’t wait for next Halloween…! Well, it does give me plenty of time to practice. Received a nice shade of nail polish from my wife this Christmas. Lipstick to match too. Now for the wardrobe…..


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