Crossdressing Blogs and Stories

Read real stories, advice and experiences shared by members of the ClubCrossDressing community. Our member blogs cover crossdressing journeys, confidence, relationships, fashion, makeup, self-acceptance and everyday life as a crossdresser or trans woman.

Whether you're just starting out or have years of experience, these community-written blogs provide practical advice, personal insights and inspiration from people who understand the journey firsthand.

The beginning

  • 📅 9 Nov, 2026
  • ❤️ 9 likes

This all began in a Puerto Rican neighborhood in the early 70s. I was the only boy in the apartment building. I have 2 s…

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Coming out

  • 📅 8 Nov, 2026
  • ❤️ 6 likes

For those who know me and have followed what I write, I sadly saw an end to a very long term relationship recently. Even…

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Coming out

  • 📅 8 Nov, 2026
  • ❤️ 5 likes

For those who know me and have followed what I write, I sadly saw an end to a very long term relationship recently. Even…

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Finally moving on.

  • 📅 4 Nov, 2026
  • ❤️ 10 likes

After the break up with my girlfriend a few weeks back. It made me realize that as much as I missed her and still cared…

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Halloween

  • 📅 11 Oct, 2026
  • ❤️ 21 likes

Aka the one night of the year I can go out cross dressed with complete impunity. I'm going for "Satan's maid". A friend…

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True Colours

  • 📅 1 Oct, 2026
  • ❤️ 28 likes

When entering the dating pool, it’s important to be honest with your date. I don’t hide behind a persona. I tell them ri…

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Isla 2

  • 📅 17 Sep, 2026
  • ❤️ 18 likes

Thank you for everybody that has made friends with me over this site and the gifts that you have sent me and the support…

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The forbidden fruit

  • 📅 15 Sep, 2026
  • ❤️ 16 likes

How why and when are the questions that come to mind. I have somehow found myself with this unusual situation. How did I…

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Men

  • 📅 10 Sep, 2026
  • ❤️ 10 likes

Lots of comments ask for updates on my dating situation, which is very nice :) So now there are 2, maybe 3.  The gu…

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