Crossdressing Blogs and Stories - Page 2

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.

Holding Hands

  • 📅 7 Sep, 2026
  • ❤️ 9 likes

Hello everyone, thank you all for making me feel so welcome on this site, I’ve made some lovely friends already, you kno…

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Dress your way

  • 📅 7 Sep, 2026
  • ❤️ 14 likes

I wasn’t always into fashion, I liked the chill part of being a crossdresser. Learning to live in your skin and wear the…

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One Day

  • 📅 4 Sep, 2026
  • ❤️ 18 likes

 One day I won’t have to hide this part of me. Maybe I’ll be accepted by my future wife. Maybe I won’t. I feel real…

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New Boy In Town

  • 📅 31 Aug, 2026
  • ❤️ 12 likes

I have met a charming gentleman and I'm a smitten kitten right now. I met him on another site where I have the same phot…

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Friend Minus One

  • 📅 29 Aug, 2026
  • ❤️ 13 likes

My friend with benefits from a previous post (a different kind of sleepover) cancelled at the last minute, like he…

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Isla

  • 📅 28 Aug, 2026
  • ❤️ 14 likes

I am new to this i love wearing women's clothes but have not tried wearing makeup and don't know where to start on what…

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Slumber Party

  • 📅 22 Aug, 2026
  • ❤️ 19 likes

So my (cis female) friend and I had a girly sleepover last night.I've a couple of girl friends I do this with from…

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Women’s Fashion

  • 📅 28 Jul, 2026
  • ❤️ 14 likes

I don’t know about you, but without a doubt women’s fashion and clothing is so much better than men’s.  Not only ar…

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