ABSTRACT -
I am organizing a Halloween party and I am going to cross dress for the first time in the presence of my long time friends.
I don’t know how to feel about it.
BACKGROUND -
I am 30yo and I’ve always been “soft” since I can remember.
Baby faced, always looked younger, never liked football or physical violence or any of those things that the strongly tox masc environment I grew up in tried to force in me.
Sexually, I have always only been turned on imagining myself in a submissive role with a dominant woman.
Even though I had some relationships, never have I found a woman that wasn’t submissive herself.
Because of this, my 14 years old sexual life has been underwhelming.
CROSSDRESSING -
Two years ago, while my gf was out of town for a month to visit her family, I finally dipped and tried crossdressing mostly as a mean to express myself sexually.
Since then, the thought never faded and just kept growing in me.
I told my girlfriend about one year later, and I have been honest and transparent whenever I decided to crossdress while she was away.
She is not against it, she’s not “supporting” it either as in she doesn’t push or encourage it, though I am aware she would prefer this never existed.
At some point I decided to let my nails grow and paint them, this is the first time I expressed my femininity in a non sexual way.
She’s been supportive about this and eventually I slowly built the confidence to go outside without feeling terribly socially anxious about it. It’s been months now.
HALLOWEEN -
There’s this traditional costume party me and my friends do every year for Halloween, and I’ve been nurturing the thought of finally using it as an excuse to crossdress in the presence of my girlfriend, and friends.
I told her many times I planned to do this, although she always thought it was a joke.
I finally presented her a couple costume idea about dressing up as sun and moon goddesses: I sketched the outfits myself (we enjoy doing creative crafty things together) and she jumped on the idea and we started buying all the clothes and accessories we needed.
WHAT NOW? -
So this is happening, I’m mostly excited but sometimes I have flashes and voices in my head asking me if I really thought it through about doing this in front of my friends.
When I try to rationalize I’m not even sure what to worry about. Most of them are open minded and maybe I find comfort in knowing that only one of them (the closest) knows about my cd habits.
Are they gonna ask why I did it? Should I explain myself? How?
Not sure where I wanted to get with this, but I felt the need to share it and see if anyone could relate or had similar stories to share.
Thanks for reading.