ClubCrossDressing ® 
Tutu
Found this little tutu skirt on line. It is so much fun and quite a thrill to wear on an outing. I love how short it is…
Read This Blog →Crossdressing Blogs and Stories - Page 8
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.
Outing in the middle of the day
Packed some sexy clothes and heels in my backpack and went on a stroll on my favorite trail. As it was the middle of the…
Read This Blog →New Lipstick
I had been struggling with my new life as a single 35+ year old crossdresser in a new job and the solitude of…
Read This Blog →Love Morning Strolls
Went out again this morning on a stroll. Like last time, I took my heels in my backpack and just wore some little f…
Read This Blog →morning stroll on hiking trail
Went for a walk on a hike bike trail this morning. Wore my little white skort, black top and sandals. Took my heels in a…
Read This Blog →Meet up
Recently I made contact with another cd who was staying in a hotel close to where I work and live. We agreed a time and…
Read This Blog →Early morning stroll
Cooler weather coming soon. Taking every opportunity to wear short shorts and skirts at every opportunity. Also wore thi…
Read This Blog →Using AI for cross dressing
I wanted to write about how we can use all these wonderful ai tools available to us, to enhance our cross dressing exper…
Read This Blog →Sissy underwear
Okay, so here is the deal. I am bisexual, and I have this thing for sissy underwear. Not just a little thing either. It…
Read This Blog →Looking for something fun!
Per my last writing, you all have come to know what I am looking for, but I am seeking more. So without being too…
Read This Blog →Figuring out a daily routine
I was thinking of having a daily feminizing routine (I already follow parts of it but not in a regular systematic way),…
Read This Blog →Driving for a rideshare company
While driving for a rideshare company, I usually only wear a skort during the early morning hours when it is still dark.…
Read This Blog →Early morning outing
Ran a few errands early this morning in some black short shorts and black heels.
Read This Blog →Alone again
I never thought I’d be alone after a longtime relationship that just ended quietly one evening after a long talk. She is…
Read This Blog →Another early morning stroll
It is such a thrill to hear my heels clicking on the cement sidewalks when I take an early morning stroll. I walked almo…
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