The Greatest Joys of Being a Crossdresser

Sheery in Wolford Iris bodysuit and Neon 40 tights

I’ve noticed over the years that the more involved I am in my crossdressing, that is getting all the little woman-like details sorted out, the more I’ve come to appreciate it even more. There use to be a point in my life where I thought it was a curse (well, many points actually) but when I came upon the realization it will never go away, I guess I thought, What the hell, I might as well enjoy it while I’m alive.

The truth is I actually feel like it’s WAY more fun immersing myself in my own feminine world. Trying that new lipstick color, searching for those perfect heels (still), finding out my perfect wig color is dirty blonde or just enjoying that feeling of being all dolled up. I haven’t even gotten into the sexual kink out of it all either which, I might add, is also pretty awesome at this stage of the game.

Anyway, here is my list of things that enjoy most about crossdressing (in no particular order)…


It’s difficult to describe that feeling when I’m completely transformed into miss me. It is kind of a warmth all over sexiness knowing this could be dangerous. Maybe it is the combination of noticing the tightness of that miniskirt or that sweet smell of Chanel that also heightens and arouses the senses to an unbelievable degree. In any case, I like this and don’t want it to stop.


I hear and read about it all the time how crossdressing is used an escape from your real self and I can say that it is true. Life is hard and we all have our ups and downs, especially me, but getting into our alter-selves does really separate myself from the real world, even if just for a moment. It is honestly the only thing to make me forget about those Zoom meetings at work coming up in the next couple of hours. Um, yeah sorry, it looks like I’m having trouble with my camera here…


Oh doesn’t that just run wild in femme mode! I don’t have much to add since you can already find them on this site.


It is fun to break the rules and do something that completely goes against society’s norms. Yes, crossdressing is becoming more accepted (OK not really, just more on everybody’s radar), however it is the thrill of the shock your friends and family could possibly receive if/when caught that does make it kind of alluring. At the very least we’re not breaking the law now are we?

The Objects

My progression into crossdressing took several steps throughout my life that can pretty much be defined by certain items that have shaped that journey and have become symbolic in their own way. I hold dear these things in making me the crossdresser I am today…

The Memories

The first time buying pantyhose. The thrill I got buying my first lingerie (or side-eye I remember from the cashier). The first time I got caught by my mom. The first time I met another crossdresser in person. Yes, those are all times that I cherish and remember to the last detail despite some being absolutely terrifying at the time. I’ll take all of those happily to my grave.

The Future

I never really thought about this until the more recent years. Yet I think acceptance of myself as a crossdresser has led to an optimistic outlook for tomorrow. Will it be wild, unpredictable and sexy as hell? I hope so!

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