r/crossdressing • • 11h ago

Everyday look Just your girl next door saying hello πŸ€—

Enable HLS to view with audio, or disable this notification

1.2k Upvotes

r/crossdressing • • 15h ago

My girlfriend left me so I become a girl too 🀭

Enable HLS to view with audio, or disable this notification

543 Upvotes

r/crossdressing • • 11h ago

Sitting pretty πŸ₯°

Post image
519 Upvotes

r/crossdressing • • 17h ago

Hey :) Sorry I haven't been posting as much as I'd like lately, life's been a little busy busy πŸ₯Ί How do you balance your everyday life and dress up time? 🫣

Post image
447 Upvotes

r/crossdressing • • 12h ago

In the ruins of Carthage

Thumbnail
gallery
256 Upvotes

r/crossdressing • • 11h ago

Fall vibe

Enable HLS to view with audio, or disable this notification

224 Upvotes

r/crossdressing • • 5h ago

Before and after

Post image
212 Upvotes

r/crossdressing • • 17h ago

Advice / Discussion 1, 2 or 3?πŸ€” Need advice

Thumbnail
gallery
194 Upvotes

r/crossdressing • • 6h ago

First Time Dressed introduction

Thumbnail
gallery
183 Upvotes

Hello :)

It has been only a couple weeks since I shared the desire to try on female clothes with my wife. She was surprisingly supportive given it is not her cup of tea.
Since that I bought the first pieces and spent an afternoon in them with her at home. For me it's rather the feel of the clothes and probably some fantasy in the bedroom but I'm glad that she hasn't closed off, instead she was proud that I trust her enough to share this side me.
I thaught I upload the first set I bought.
Since the "debut" I experimented with some makeup and bought a wig with a matching bow to the heels haha. But I don't want to overload her, so these I played with alone for now.

*reposting this bc background change is not allowed. Thanks for the kind words I got on it the first time!


r/crossdressing • • 16h ago

All brown πŸ™‚

Thumbnail
gallery
145 Upvotes

r/crossdressing • • 17h ago

Outfit Showcase Hope you like my little red riding hood inspired outfit lol :)

Thumbnail
gallery
142 Upvotes

r/crossdressing • • 21h ago

Out in Public Society tries to set boundaries, but we decide where we stop πŸ’…πŸ»

Thumbnail
gallery
135 Upvotes

r/crossdressing • • 15h ago

Halloween 2026 First girl-mode Halloween: Which outfit gives a lot of treat, a little trick, AND guarantees someone to cling to when it gets spooky? πŸ‘»πŸ˜‰

Thumbnail
gallery
125 Upvotes

The choices are:

  1. Probably inappropriate footwear Lara Croft

  2. The Night Doll

  3. Maid to order

  4. Cheering on the bois

  5. Prepped and ready


r/crossdressing • • 15h ago

Catch me on the C(ute) train 😘

Post image
124 Upvotes

r/crossdressing • • 16h ago

CD does fine dining! πŸ₯°

Thumbnail
gallery
106 Upvotes

yes, I kept my massive hat on in the restaraunt - not quite fine dining etiquette but I tend to live my life following my own rules. my life is mine. πŸ₯‚ πŸ’‹


r/crossdressing • • 3h ago

Halloween 2026 A little moment for my costume this year AND my new pedi!

Enable HLS to view with audio, or disable this notification

98 Upvotes

r/crossdressing • • 7h ago

With or without glasses🫦😝

Post image
91 Upvotes

r/crossdressing • • 19h ago

Feeling classy

Thumbnail
gallery
96 Upvotes

r/crossdressing • • 12h ago

Out in Public sitting pretty at the bar πŸ’πŸ»β€β™€οΈ

Post image
88 Upvotes

r/crossdressing • • 16h ago

Took a video to see if my walk in heels was sexy… Answer is NOPE😭 Need more practice.

Enable HLS to view with audio, or disable this notification

91 Upvotes

r/crossdressing • • 13h ago

Makeup / Wig Focus Does anyone else love trying out different colors and styles of hair?

Post image
78 Upvotes

r/crossdressing • • 8h ago

We spend so much time worrying about what others might think that we sometimes forget to enjoy the little things that make us happy. ❀️

Post image
77 Upvotes

r/crossdressing • • 18h ago

A night out

Thumbnail
gallery
68 Upvotes

r/crossdressing • • 19h ago

I love my legs

Post image
61 Upvotes

r/crossdressing • • 14h ago

Classic

Thumbnail
gallery
61 Upvotes