I first tried on my sister’s clothes at age 10. I don’t have a strong recollection of why or the moment- but I do remember always finding the clothes mysterious in that they were both pretty and off limits- but nobody ever explained why. So I secretly helped myself. 

I wish! I remember a few dresses from my sister’s closet- a few dresses I knew she never wore, some pleated skirts from her school uniform. I found it all very confusing and exciting. I had no guidance. I didn’t really know what I was doing or why but I knew it felt good and as I was starting puberty, a little sexy. 

Femme, flirty and classic.

Women who were sexy during the 90s and up to today. Pop stars who go a little over the top (Ariana Grande, Sabrina Carpenter)  and of course other crossdressers!

Before I got married I bought a wedding gown and did a shoot all dressed up as a bride. Did the whole affair- veil, bouquet, etc. It was one of the most important adventures for me because I was marrying someone who has made room for my femme self to exist and show off, but she doesn’t get to participate in the relationship. So I gave myself a chance to be the bride for real- or as close to one as possible. I posted those pictures with nearly no edits- beard stubble and all- and its my favorite shoot I’ve ever done. That $90 amazon wedding gown is my most favorite piece and I’ll probably never wear it again. 

First is body hair- trim arms, legs, shoulders, belly and butt. Then I shower off and put on my tits and my getting ready jammies. Makeup takes 45-60 minutes. Then outfit- which is usually planned but will need some edits, and accessories and shoes which are rarely planned. Hair is the moment that everything changes- when I start to see a woman looking back at me in the mirror. If I am not completely exhausted by this point I will add nails. 

It was pretty immediate, but learning to do a feminine brow has been crucial. So many girls skip the brow and its tragic!

From shave to the first pictures, about 90 minutes 

My wife likes my beard, so I have to figure out how to cover it up with makeup. Other than that, its trying to look petite and cute when you’re starting out as a 6’1” 250lb man.

Crossdresser and gender-fluid.

This is probably the part that has evolved the most for me in the past few years. I used to see it as playacting, engaging in a silly fetish. Then it became a persona, Kaylee, who was still someone separate from myself. More recently, I’ve started to understand dressing as  Kaylee as accessing a part of myself that doesn’t get to show up otherwise. So all of the above. 

Lust. Maybe it’s a bit embarrassing to admit but my initial and primary reason for dressing is that I find the idea of myself appearing feminine to be erotic, and now that I’m good enough at it to convince myself… well, let’s just say I serve as my own pornography. 

I’m out to a couple family members, and to a good number of friends. It took first coming out to myself- for years it was just a silly thing I did sometimes. The hardest part was coming out to myself- my therapist helping me to say out loud “I am a crossdresser” was probably the biggest turning point. After that, coming out to my partner and friends has been amazing, they have all been so supportive. Especially after I show them pictures. Then they realise I’m not messing around. “Holy shit that’s YOU?!” Is the usual response, and I love it. 

My wife has definitely given the most- given me time in the house to dress, and the privacy and freedom to be this part of me and still be partners with the rest of me. My friends Shannon, Luiz, and Mike deserve mentions too- they’ve been huge supporters of Kaylee and always want to help and see everything she’s up to. 

I came there to find like-minded friends because I was going bananas having all of this inside me and nobody to talk to about it. I ended up becoming a content creator and gaining something of a following- the best news is other creators have connected with me and I have now a community around me of other crossdressers to talk about all this stuff!

I don’t think we need to be understood. We're pretty private people. If you don’t get it then I think just leave us alone. 

For me they are inextricable. Kaylee is my sexual side. 

She tolerates it, and she makes space for it, and for that I am grateful. However it definitely occupies more of my time and psyche than she would like, and can be a point of contention for us. But we make do. 

Not in person yet, but my Fetlife account is pretty popular, and each time I post pictures I get a bunch of comments and DMs saying things ranging from sweet to sexy to downright nasty. All based on the premise that I am pretty and attractive to them. I’m not going to lie, I love all of it.

At the beginning I was fully submissive. But I’ve found there is some power in being “hot” that some like to defer to. So now I play both sides. 

Yes, femdom for sure. I’ll dabble in others, but CD is the main one. 

Learn to do your brows. Makeup is way more than eyeshadow and lipstick. Brush your damn wig! Every time!

As someone who still sorta needs to hide the amount of clothes she buys- the Amazon locker is an amazing tool. When I can control the arrival date I love shopping on DollsKill, and if you’re a CD and you haven’t been to OnlyMaker.com for heels, you’re really missing out!

Putting on my Sailor Jupiter outfit for a group project- so many pieces and layers to get on. Its also summer and the room I dress in is quite warm. Takes me almost 2 hours to get ready but I’m almost done. The very last bit is a pair of white gloves. I reach up to wipe my brow and leave a large foundation stain on my glove. Then another on the other glove and my collar trying to get the first stain out. In the end I rage quit and had to do the shoot again on a later date when it was thankfully cooler out. 

Definitely worth it for a nice chest plate.

Have not yet. I want to very soon though. It will take at least a couple supportive friends- ideally also CDs, and a location/event to go that was accepting. I hope to do this in 2026

Right now its to go out crossdressed, and then the ultimate outfit is the full cheerleader uniform.

Probably. Although the ease (privilege?) boys have of throwing on jeans and a tee and being fully dressed would be hard to give up. 

Hopefully where it is now I hope. But lately I’ve been exploring collaborations with other creators and I love where that is taking me! So hopefully there. 

Lock the door and put it on. You won’t know if this is for you until you do. And after that- drop the shame and the guilt. There is nothing wrong or evil about crossdressing. Its clothes. Everything else is what other people put on you. 

Coffee or wine? 

Wine. I don’t like coffee. 

Daytime glam or evening seduction?

Seduction. Even if it starts with glam it ends with seduction. 

Heels or flats? 

Are you kidding? Heels! Tall and strappy. Now ask heels or boots. 

Bold lips or subtle gloss?

Bold

Lipstick shade you're wearing right now (or wish you were)? 

Almay “Let Them Eat Cake” is my go to, recommended by a friend and worn regularly

Well if it's the general public we’re talking to, it would be  just the mere concept that we exist! Crossdresser is not simply a derogatory term for a trans woman- we are our very own thing and we are not trying to imitate or hurt people who are discovering themselves and definitely not trying to fetishize an identity.

Crossdressers exist - and for one reason or another we want to express a feminine side of ourselves. It may be sexual, it may in fact be identity related- many crossdressers find it a first step to transitioning and so are tied strongly to the trans community.

For me, it started as something sexual and now I consider myself Gender Fluid, and through my online community (and now growing in-person community) I have many friends who are trans women. I would hate to think that my mere  existence offends them.

We exist and we are harmless- we mostly want to play our little dress up game in private, maybe if we’re attention seekers like myself we’ll post pictures of ourselves for folks to gawk at. But if you don’t like us you may largely ignore us. It’s usually a solo activity. 

To other crossdressers I would pass on this- there is nothing wrong, immoral, or shameful about what you are doing. Yes, the activity is largely looked down on by the heteronormative society we live in, but in modern times we see that occupying less and less of what the world accepts as truth.

You wearing heels and a dress and makeup in the privacy of your own home hurts no one, and only affects you. If it makes you feel happy, excited, aroused, more whole, or best yet- more YOU- then do it. Engage in the activity that brings joy and positivity into your life and try to drop the guilt and shame  that you are placing on yourself for doing it. The more you dress, the easier it will get, the better you will get at it, and the easier it will become.

So do it more often and wear more cuter things!

Who should I interview next? Drop a name in the comments.