r/ChicagoCrossdressers

Hey everyone, hope all are well, I wanted to ask all my trans cross and sissy women out there how they would feel about this scenario. Would you be offended or honored? My wife knows I have a fascination about trans and passable cross dressers and may one day want to have an experience. A bucket list sort of thing. Would you be offended or be honored to have played a role in a couples life?

Any crossdessers in here like to dress newly cross dressers up? Ive never went full blown crossdressing but would like to maybe for a night or two. I’m 25 and muscular and would like it to be private please

Hey all you sexy sissy sluts. ​Anyone interested in a meet and great in the Chicago metro area, please message me and I will add you to our group chat. We are currently seeing if there is a moderate interst. If there is we will have a small party and share ourselves. We'll have a sexy good time!! Some drinks, some stories, some whatever happens next ​😘 Show us your sexy girly side. Hope to see you all soon.

Really want to experience a man but sissy is preferred