r/ChicagoCrossdressers

As a typically straight and masculine guy, this might be one of the most embarrassing things I have ever done lol

Cant believe I am doing this lol.

u/redsoxs047 — 22 hours ago

F19 Hey come closer

Looking for a witty guy who knows how to keep me smiling without even trying too hard. I enjoy playful energy and someone who can bring something different to the table. If you’ve got charm and confidence, I’m already curious. Don’t be shy. ✨

reddit.com
u/AMFred85 — 1 day ago

19F You’re dragging this out on purpose, aren’t you?

It’s really not that deep just a simple moment, nothing complicated or heavy. No need to overthink it or stretch it out a quick reply is all it takes to keep things easy and not leave it hanging like this.

reddit.com
u/Chrisbranch1084 — 19 hours ago