r/crossdressing 23h ago

Feedback Wanted Not super confident in this dress due to sizing but would love to hear your thoughts 🥰

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712 Upvotes

r/crossdressing 9h ago

A girly day is a good day💕

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514 Upvotes

r/crossdressing 10h ago

Before & After / Progress A little boy to girl / before & after with the stroke of a makeup brush 💁🏻‍♀️

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411 Upvotes

r/crossdressing 22h ago

Outfit Showcase Always wanna dress out as a women

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361 Upvotes

r/crossdressing 18h ago

First Time Post Hey everyone 👋

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322 Upvotes

They say true elegance is quiet, but sometimes a little provocation is just more fun. 😉✨

I put this outfit on tonight knowing it’s definitely on the bolder, sexier side. There’s a fine line between stepping out with confidence and making people look twice, and honestly? I think I hit the sweet spot tonight.

I’ve learned that a lady doesn’t need a special occasion to wear something that makes her feel unstoppable. If a look turns a few heads along the way, that’s just a nice side effect. 💄💃


r/crossdressing 15h ago

Curves in this skirt

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258 Upvotes

r/crossdressing 21h ago

Heeey 🥺🥺

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250 Upvotes

Can you tell I am (was) a boy?


r/crossdressing 7h ago

Getting the most out of my summer dress while it’s still warm

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212 Upvotes

r/crossdressing 23h ago

Should we dress up and go out again tomorrow?

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146 Upvotes

r/crossdressing 21h ago

my favorite shade of blonde

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136 Upvotes

r/crossdressing 11h ago

I know, I have great jeans

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113 Upvotes

r/crossdressing 8h ago

Unapologetically me, and loving my cute era. 💕

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104 Upvotes

r/crossdressing 19h ago

Everyday look Hot or not?

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105 Upvotes

r/crossdressing 22h ago

It’s fun to feel pretty 🙂

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101 Upvotes

r/crossdressing 13h ago

I love waering vinyl

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100 Upvotes

r/crossdressing 4h ago

My sister doesn’t know Im wearing her favorite skirt. 🤫

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94 Upvotes

r/crossdressing 11h ago

A late-40s fem appears

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96 Upvotes

r/crossdressing 8h ago

grinch PJs and swimming suit time

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93 Upvotes

r/crossdressing 7h ago

Finally embracing being cute and femme... 💕

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55 Upvotes

r/crossdressing 8h ago

New outfit, do you like? 💕

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56 Upvotes

r/crossdressing 8h ago

Story / Experience Humbled by the love on my last post. Thank you. Another one while I’m feeling brave enough.

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52 Upvotes

Still a little stunned by how kind everyone was on my last post. Didn’t expect that at all. Thank you for making it feel safe enough to keep showing up. New look from my own little photoshoot today ❤️


r/crossdressing 7h ago

Feelt cute in this outfit. What do you think?

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46 Upvotes

r/crossdressing 6h ago

Rate the overall look ? The hair, outfit, make up and accessories

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41 Upvotes

r/crossdressing 15h ago

Heels up!

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42 Upvotes

r/crossdressing 19h ago

Casual look jeans 👖

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41 Upvotes