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Penelope “Penny” Rose

Crossdressing in hotel room
Name: Penelope “Penny” Rose

▶ Location: San Francisco, CA

How long you have been crossdressing: On and off for the past 10 years but seriously only for the past 6 months..

Say something about your crossdressing experience: My crossdressing experience is probably similar to a lot of folks: trying on some clothes from my mother and sister when I was younger, then later in life buying some clothes, then purging and pushing my feelings away. I went through that buying-purging-repressing cycle multiple times and I am happy that I was finally able to break out of that loop.



Embracing my desire to crossdress has really opened up my horizon and given me feelings of satisfaction and happiness that were previously unknown to me. I love exploring different styles, trying out all kinds of outfits and just feeling confident in myself while doing so.

Reason you crossdress: It allows me to feel feminine, desirable and pretty in a way that I could never do in guy mode. It’s like I’m unlocking a whole new part of myself that is super fun to explore.

Things you like doing after dressing up: Taking lots of pictures, that’s for sure. One of these days I hope to even take my first step outside in Penny mode.

Instagram: https://www.instagram.com/penelope_penny_rose/


 Photo Gallery:

crossdresser in pantyhose and heels

Beautiful crossdresser in black dress

hot crossdresser

guy dressed as school girl

Penelope dressing as girl

cute crossdresser Penelope

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