Kasey Lynn

Crossdesser Kasey Lynn
Name: Kasey Lynn

▶ Location: I live in the South West suburbs of Chicago, Illinois USA.

How long you have been crossdressing: I have been cross dressing since around nine years old. I just loved seeing dresses and cute clothes on girls and wished I could wear them. I had no idea why I felt this way. After I started borrowing my sisters clothes and wearing them in my room, it just felt so natural and made me feel happy. I felt like a girl.

Say something about your crossdressing experience: For me growing up with this desire to dress in female clothing was never fetish. I would go to sleep every night wishing to wake as a girl. Every day brought more disappointment. As I got older, I was able to acquire my own clothes and Started experimenting with make up. I liked who I saw in the mirror. I would still do all the boy things I was expected to do and dated women and actually married one. Although my life was great, I still felt incomplete.

The desire to dress did not go away. I dressed when I could as time allowed. Also was very private and did not tell anyone. Fast forward to a year and a half ago when I got divorced. It was a sad day but also the happiest day of my life as I now knew I could be on my own and dress whenever I wanted. Over the next year and a half Casey exploded onto the scene as I wanted to explore her fully. Trying to figure out what I want out of life and who I want to be.

I stepped out of the house for the first time and it was magical. Mostly at night to start, I would take walks and short drives. As I gained confidence I started going out during the day to parks and stores where the public would see me. I wasn’t going to hide anymore. I go to social clubs now and only dress and female clothing while at home or go out as Kasey. Sadly, I still dress in Guy mode when at work and see friends or family.

I now realize that I am trans and want to transition. This will be the greatest happiness for me. I will let the people closest to me know my intentions as time goes on. It feels so natural to me to dress and be seen as a girl. What was always a nervous and exciting feeling, now feels normal and how I should be. Just one of the girls.

Reason you crossdress: I started cross dressing because I was attracted to the soft and frilliness of female clothing. Primping and making yourself look cute. I just wanted to have all the curves and parts that make you female. I felt inside that this was me. Just trapped in this male body. It’s like you’re in a box screaming, but no one can hear you.

Just dressing when I could felt so euphoric and satisfying. I was scared to take it any further because I thought it out of my reach. Now, I’m so happy things are much easier to start transitioning. Medically and socially. When I got on Instagram, I realized that there are so many more like me and I’m happy to be one of them.

Things you like doing after dressing up: it’s not like I like to do certain things after dressing so much as well not dressing. These will all merge in due time. I am a graphic designer so I like to draw and be creative. Making something out of nothing. I like playing sports and going for walks. Hiking is big for me as I love to discover new places. I know I am very female orientated as I am a romantic, I cry watching movies, I cook a lot, have a soft heart and care about everything.

I am open minded when it comes to dating as I could see myself married one day. And it could be with a CD, trans girl, a woman or even a man. It just depends on the connection you have and how you get along. I leave all doors open. One more thing, I love creating content for my page. I like making videos that are fun for me and what I hope is fun for my followers.

▶ Instagram:

 Photo Gallery:

Kasey crossdressing in public

man to woman transformation

Crossdresser Kasey in bodycon dress

Casey dressed as woman

guy dressed as girl

man dressed as woman


Facebook Comments


  1. She is super nice on my eyes! Kasey Lynn, you are gorgeous from head to toes! 🥰🥰🥰

  2. You look cute, and I liked very much to read all your story. Thanks for sharing it!

  3. Oh my you are gorgeous! I could be convinced to go to Chicago for a visit or even better yet you could come here and warm up in FL!

  4. Again thanks for your story and honesty as it was lovely to read. Wow what an absolute stunner Kasey, you’re so beautiful and natural and looking forward to seeing your journey. All the very best 😘

  5. I think you are so Gorgeous definitely passable would love to meet am in the south suburbs in Joliet area hit me up if you would like to meet up or ? Looking for a FWB or more….

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