Crossdressing First Time Out Gallery

wof-pride-flags bowsbethandsansa laurenonfr thecolorofmycrazyworld mymilfalicious

cant wait to feel my first cock… still looking

my first regular panties.. love how they feel..like?

New content on the way soon, but first a weeks vacation. Leave us some ideas for what you would like

cindycross-39: Me Cindy Cross crossdressing - one of my first outfits and photoshoot. Still love the

sexyalyssa1: sissyvaspira:k1nkypaws: Oh Hell Yeah hehe very true . you see the panties first lolOh y

Hiiya just wanna make an update. This is gonna be the first dress I buy. I just have to wait for it

The first outfit for my crossdressing I ever put together, circa 2012. My purse is more denim than b

Hiiya, its my first time posting something like this. Hope someone out there likes it

smokey-heart: At first you were horrified, but then you realised you were going to enjoy life better

first time with cage.Reblog and add you own Caption

My first successful attempt at creating cleavage three years ago. #tbt #photooftheday #instagood #

First time. Please be gentle

iwanttobeasissywhore: hotwivesclub1:First meet outfit this is always my “first meet” out

❤❤❤My first original caption, go easy. Oh who am I kidding, I’m a sissy slut, no need to go ea

Nothing to be nervous about. Yes, he’s a man, but nothing has changed about your first appeara

The other day I went to the beach wearing a swimsuit for women♡ It was my first time to go to publi

Hey. Took these last night. Felt confide t at first but eh. Only got these three decent ones. Maybe

Henlo, Got a question and some things i wanna say. Ok so first of all… CHRIST ON A BIKE!!! Y

tendingmysecretgarden: Here’s some classic crossdressing art from one of the first such books

Zoes first trip out!

This is like the very first rule of crossdressing… Especially for the slutty gurls

sexyalyssa1: sissyvaspira: k1nkypaws: Oh Hell Yeah hehe very true . you see the panties first lol

So Erm, this is my first attempt at minimalist day to day makeup. No eye shadow, tiny bit of eye lin

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