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Kayley Catherine Sullivan

man to woman transformation
Femme name: Kayley Catherine Sullivan

Location: New York City, NY

How long you have been crossdressing: Since fifth grade. I always wanted long hair as a child, so one day I went out and bought a gorgeous long wig, and from there it kept going.

Say something about your crossdressing experience: It has helped me to realize the larger issue of my gender dysphoria and forced me to accept my identity as transgender woman. It has liberated me from the shackles of masculinity and allowed me to feel comfortable in my expression.

Crossdresser KayleyReason you crossdress: Because I feel more comfortable in clothes that are gendered for woman because I myself (several years later), realize that I am in fact a woman.

Things you like doing after getting dressed: Doing normal things! I like going out and being able to express my true gender.

Your favorite outfits/style: Kate Middleton has always been my style icon, but her clothes are usually too expensive and her gorgeous hair too hard to replicate. These days I go for a very tame trendy style, trying to blend in and pass, rather than go over the top with femininity.boy to girl transformation

Where do you buy your clothes/makeup/shoes from: Forever 21, brandy Melville, Amazon, and h and m. My shoes all come from Amazon though because they’re the only ones who carry shoes of my size!

How long does it take you to get ready: Even though I have been doing this for so long, I still suck at makeup. It takes me usually 40 minutes to do my eyeliner if I’m doing a winged look. All together to get my outfit, hair, and makeup done, probably an hour and a half to get ready.

▶ Instagram: @kayleysully

Photo Gallery:


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Facebook Comments


  1. Very pretty.if your ever in Ohio get ahold of me

  2. You are absolutely gorgeous girl……would love to meet and get together im in NY too…lets chat email me please

  3. I like the transvestite life.

  4. Do you like men because we like you xx

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