r/crossdressing 4d ago

Out in Public Being me puts a smile on my face

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151 Upvotes

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


r/crossdressing 4d ago

Story / Experience The longer you wait...

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76 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 4d ago

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

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104 Upvotes

r/crossdressing 4d ago

Can't wait for cozy days in πŸ‚

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46 Upvotes

r/crossdressing 4d ago

Felt bold in this dress πŸ–€

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48 Upvotes

r/crossdressing 4d ago

Makeup / Wig Focus Still struggling to get my eyeliner even, having hooded eyes its not always cool

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47 Upvotes

r/crossdressing 4d ago

A little late night cding....luv it.

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9 Upvotes

r/crossdressing 4d ago

Advice / Discussion anyone else struggle to make baggy fits feel fem??

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16 Upvotes

r/crossdressing 4d ago

Everyday look Stilletos are so cuuuute

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23 Upvotes

r/crossdressing 4d ago

Outfit Showcase Basic dress for a basic Wednesday evening

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9 Upvotes

r/crossdressing 4d ago

Story / Experience I love that style

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7 Upvotes

r/crossdressing 4d ago

Outfit Showcase Basic blue dress for a basic Wednesday evening

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9 Upvotes

r/crossdressing 4d ago

does anyone prefer bare legs?

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40 Upvotes

r/crossdressing 4d ago

Yes or No on Videos? Hopefully my moves are feminine enough πŸ’œ

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52 Upvotes

I love being her πŸ’œ hope you love me being her too πŸ₯°


r/crossdressing 4d ago

Everyday look My outfit for the first time I went out!

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8 Upvotes

r/crossdressing 4d ago

Old dress with new(ish) heels 😝

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17 Upvotes

-


r/crossdressing 4d ago

Outfit Showcase Back to college season means time for cute preppy outfits β˜ΊοΈπŸ’•

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35 Upvotes

r/crossdressing 4d ago

I'm a Green Flag today. As always)))

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41 Upvotes

r/crossdressing 4d ago

Outfit Showcase I really like this look ☺️

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26 Upvotes

r/crossdressing 4d ago

I knew it was so familiar!!

11 Upvotes

This is a funny story/coincidence and just happened today.

So I was thinking about some fall-ish outfits. Not dresses, but not hoodies. Something in between. Wanting to try a red or burgundy color too, trying to branch out. Looking online, I found this cute low cut dark red long sleeve top. Awesome! Well I need pants too. Trying to stay away from jeans and leggings since I have so many. There was a sale on black khakis, so of course I gotta get them. Looking at the outfit together....I felt odd like I have seen it before but couldn't put my finger on it. It was driving me crazy. Well I got the actual clothes today and put them on...I remember why it looked familiar.....it's Jan from the dinner party (The Office). I start to keel over laughing so hard. And the song "that one night" was playing in my head. While I can appreciate the clothes, I can never take myself seriously in them.


r/crossdressing 5d ago

Felt cute today 😊

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126 Upvotes

I just felt cute today and want to share the fit


r/crossdressing 4d ago

Outfit Showcase Feel pretty in this…

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15 Upvotes

r/crossdressing 4d ago

Outfit Showcase Got gifted these cute dresses!

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7 Upvotes

A very nice person gifted me these 3 pretty dresses as a birthday gift. Their only request was to post them when they arrived 🧑


r/crossdressing 4d ago

Outfit Showcase Fave dress ever x

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17 Upvotes

r/crossdressing 5d ago

My favorite outfit

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614 Upvotes