TBFS Girls: Meet Samantha Chepan

Since 1993, we’ve created space for cross dressers, transfeminine, and gender-fluid people to express, explore, and simply be. You don’t need permission — just a place that sees you. And through every image and story you share, it’s clear: you belong, and you’re never alone.

Meet Samantha

What’s your name? What are your pronouns?
Samantha Chepan. I consider myself gender fluid – I use she/her exclusively when I’m dressed femme, but any when I’m not.

Where are you located?
Northern Delaware, USA

What’s your favorite thing about expressing your feminine side?
The clothes! I have always been jealous of feminine style and choices… dresses, skirts, blouses, jumpsuits, lingerie, while guys get pants and shirt. There are just so many options, so many ways to mix and match or align your wardrobe with your mood. Plus I’ve always had some mannerisms and characteristics that I’ve tried to mask or hide in the name of being “a man”. Embracing my femininity has made me less paranoid and worried about hiding them.

How would you describe your style?
It’s pretty varied. When I first started exploring my gender, it was very sexual/kink-based. So I have a fair amount of latex, leather, PVC, corsets and such. I’m also very strongly drawn to a goth aesthetic. But I also love a soft flowy sundress or a peasant skirt. I guess in the end, it’s anything that makes me feel pretty and/or sexy – I’ve never felt terribly attractive when presenting male, but I really love what I see when presenting female.

Where are your favorite places to shop?
For the longest time, almost all my shopping was done online – Amazon, Temu, Shein, etc (though there is a great kink shop in Philadelphia called Passional). But I am a big fan of thrifting and consignment shops now! So many options, so many things you might never see in any other store, and it’s different every time you go in. Now I just need to find a kinky consignment shop. 😄

What piece of advice would you share to someone starting dressing?
First of all, just go for it! If you’re thinking about it, if you have an interest, if it’s something you’ve wanted to try, just take the leap and do it! Don’t hide it and deny it from yourself, and wait until your midlife crisis to finally take the plunge. Yes, it’s better late than never, but you’ll also kick yourself about all the lost time when you could have been embracing your true self.

When starting, pick one thing that appeals to you most, be it the clothes, the makeup, the shoes, what have you. Then if you’re nervous about going out shopping for them, pick a low-stress place to do it. For clothes, go to your local thrift shop and find a couple pieces that appeal to you. It’s an inexpensive way to find a ton of options to help you find your style. Plus nobody pays attention to men in the women’s section of a thrift shop. And even if they do and you feel like you need an excuse, tell them that you’re looking at costumes for a local theatre production. If it’s the makeup, check the cosmetics section of your drug store (as opposed to Ulta or Sephora).

Make the internet your best friend. There are a bunch of great resources available, including tutorials for makeup, Discord servers and Facebook groups to find people to talk to, etc.

And finally, get yourself a good set of breast forms, put yourself together, sum up whatever courage you have, and get out there! There is nothing in the world as scary and simultaneously liberating as the first time you go out in public dressed. Whether crossdressing is where it ends for you, or it leads to examining your gender identity, it’s a journey that you’ll be thankful you went on. So come join us at a girls’ night!

Check Samantha out on Instagram & Facebook!