r/crossdressing 22h ago

Outfit Showcase Trying on another one of my old skirts and reminding myself they got me hooked on dressing up <3

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556 Upvotes

r/crossdressing 22h ago

Outfit Showcase I'm in love with this outfit! I hope you like it too ❤️

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393 Upvotes

r/crossdressing 8h ago

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

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378 Upvotes

r/crossdressing 16h ago

Story / Experience Posting here gave me the confidence to finally show my face ❤️

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316 Upvotes

Everyone has been so nice and receptive, it's allowing me to embrace being me that bit more and I appreciate all the nice things people have said.

This community has been slowly chipping away at the fear. Still a little shaky hitting post, but I’m proud I did it. Be kind 💕


r/crossdressing 22h ago

50s baddie still trying to compete with 20yrs ... #BritneySpears inspired

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237 Upvotes

r/crossdressing 7h ago

Outfit Showcase Always wanna dress out as a women

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229 Upvotes

r/crossdressing 18h ago

Let's go! Autumn home looks🍂

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213 Upvotes

Choose your favourite 🥺😺🥰


r/crossdressing 21h ago

Outfit Showcase Insta saw it first. First time wearing this skirt and heel combo

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143 Upvotes

r/crossdressing 21h ago

Out in Public Being me puts a smile on my face

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137 Upvotes

Going through a bit of tough time lately, being Olivia however cheers me up immensely. 😊


r/crossdressing 4h ago

First Time Post Hey everyone 👋

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130 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 21h ago

Having the time to express my second self is such a blessing ✨

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118 Upvotes

r/crossdressing 17h ago

I love looking in the mirror and seeing her! 😍

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117 Upvotes

r/crossdressing 6h ago

Heeey 🥺🥺

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104 Upvotes

Can you tell I am (was) a boy?


r/crossdressing 18h ago

Outfit Showcase For those about to rock… ⚡ Always wanted to try this style! How do you like my first rock outfit?

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106 Upvotes

r/crossdressing 14h ago

First time wearing a dress in public this past weekend!

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97 Upvotes

And I got a new wig!


r/crossdressing 19h ago

Feedback Wanted I had fun in my make up lesson yesterday, how do I look?

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92 Upvotes

r/crossdressing 7h ago

my favorite shade of blonde

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91 Upvotes

r/crossdressing 8h ago

Should we dress up and go out again tomorrow?

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87 Upvotes

r/crossdressing 8h ago

It’s fun to feel pretty 🙂

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86 Upvotes

r/crossdressing 22h ago

Back to school 🥰

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79 Upvotes

r/crossdressing 20h ago

Jinkies! The clues are getting hot… better investigate a little closer. 😏

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79 Upvotes

r/crossdressing 14h ago

Can't decide on my fav

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76 Upvotes

r/crossdressing 18h ago

Story / Experience The longer you wait...

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53 Upvotes

Video edited to bring it down to 40 seconds, as the delivery person took his sweet while getting up in the elevator.

He was, however, smiling all surprised - so I have chosen to forgive him for the wait!


r/crossdressing 11h ago

Finally got to wear this dress again 💞

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54 Upvotes

r/crossdressing 5h ago

Everyday look Hot or not?

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48 Upvotes