The Greatest Joys of Being a Crossdresser

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)…

Sensuality

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.

Escape

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…

Fantasy

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.

Taboo

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…

• Pantyhose
  The obvious one yet it is where it all started. I can’t explain the early fascination or the irresistible attraction to it but it was the source of my kink in my younger days. Still to this day, I love my Wolford Neon 40s and always carry around a pair wherever I go.
• Lingerie
  I can remember as if it were yesterday walking into that JC Penney store in the mall and buying that turquoise blue camisole/panty set… at 15 years old. Needless to say, I’ve been adding to the collection non-stop and has been an accessory for my pantyhose ever since.
• Heels
  I never really got into womens heels until later in the game, likely because I use to get the cheap ones and they did absolutely nothing for me. A decent pair of stiletto heels, however, is a different story making my legs look more slender and feminine. Twenty-three pairs later…
• Wig/makeup
  This was where things have gone to the point of no return. Spending the time experimenting with those lipsticks and eye shadows and, not to mention, finding that beard concealer changed my thinking to Wow, it really is possible to not be the man in womens underwear anymore! Finding that right wig put the finishing touch to it all.
• Perfume
  A sweet perfume rounds out all the senses (along with the vanilla taste in that lipstick) and makes the whole transformation a truly sensual experience (see above). Plus it doesn’t hurt to let out a kind of pheromone presence, does it?

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!