Have you ever crossdressed?

Just curious. Really wanting to try. How to get started? Tips? Advice? Stories?


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Most Helpful Guy

  • Before I got married, I had a friend and she let me borrow her lingerie.

    This sort of thing my wife strictly forbids.

    Why, when we ere engaged I once asked, "who gets to wear the wedding dress? You or me?"

    She almost called the whole thing off.

    Oh yeah, she got to wear it.

    Trust me guys, don't ever do that.

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What Girls Said 1

  • Yes I have crossdressed most of my life and for the last 5 years I have gone out a couple times a week. As for tips or help there are many options. Most big cities have businesses that will do makeovers for crossdressers but costs some money. Most cosmetic counters at stores like Nordstrom’s or Macy’s are more than willing to help as a lot of them get a commission. Find a female friend that is willing to help, this takes some trust. Also Facebook is a wonderful way to meet other crossdressers and get support and help. Here in Portland Oregon we have a T-girl yahoo group that has 230 members and on a Friday night we can have 15 to 40 of us out together. Find friends that you can go out with as it really makes it a lot easier.

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What Guys Said 12

  • i have it is tons of fun! I looked so hot! I have the pictures on my Facebook -- by the way I am 100%... (well.. maybe more like 95% straight)

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  • one time when I was 7 I thought this one shorts for me to wear, and then my mom laughed and told me it was a skirt. and I had to change.

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  • no

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  • An old girlfriend dressed me a couple of times...

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  • Nope.

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  • Nope. I guess try out with something small, maybe make up or a feminine shirt.

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  • Yeah when I was in high school a bunch of my guy friends and I did it as a joke on halloween. High heels suck, I don't know how girls do it...

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  • ... I did once...

    ... ;_;

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  • yes and I love it

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    • I noticed your straight and enjoy crossdressing. I'm the same way I feel relaxed and free while doing it. How far do you take crossdressing?

  • Yes I have and love doing it I'm actually planning on full drag real soon.

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    • Go to ross or a store like it for shoes and a dress, skirt or outfit. I wear tights or hanes sheer silk reflections pantyhose. I'm looking into makeup, wig and nails now myself. You can message me if you want to chat.

  • Hmmm I've tried on make up and girls clothes before but I'd never do it again haha.

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  • Yes, it was funny!

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