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"crossdressing" Memes & GIFs

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Sissy wears make-up

Sissy wears make-up | ENJOY LIFE; AS A SISSY | image tagged in allison blake,sissy,crossdressing | made w/ Imgflip meme maker

3,168 views, 6 upvotes

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Harry Styles "Rewriting the Rule"

Harry Styles "Rewriting the Rule" | "HARRY STYLES IS REWRITING THE RULES OF MASCULINITY ON HIS TERMS"; UM.... NO YOU'RE NOT | image tagged in harry styles,kurt cobain,crossdressing,rockstar,pop culture | made w/ Imgflip meme maker

3,680 views, 4 upvotes, 1 comment

I'M TOO PRETTY; FOR MY SWORD | image tagged in final fantasy vii,cloud strife,trap,crossdressing,pretty boy,too sexy | made w/ Imgflip meme maker

by anonymous

3,461 views, 1 upvote

Aniplay

Aniplay | WHEN YOUR MALE FRIEND WANTS TO JOIN A GROUP COSPLAY; BUT THERE ARE ONLY FEMALE CHARACTERS | image tagged in cosplay,humour,trap,crossdressing | made w/ Imgflip meme maker

by LuciferMogarCinderblaze

18,853 views, 5 upvotes

"JOIN MY GUILD," ASUNA SAID; "YOU'LL LOOK GOOD IN THE UNIFORM," SHE SAID | image tagged in kirito,sword art online,crossdressing,uniform,guild,join me | made w/ Imgflip meme maker

by anonymous

14,759 views, 4 upvotes, 1 comment

Emma Watson picks out your clothes

by unexpectednudeity

22,968 views, 8 upvotes

by Veronicafordaddy

20,674 views, 5 upvotes

Jennifer Aniston wants to play dress up

by unexpectednudeity

37,563 views, 5 upvotes

Ash Ketchum the Cutest Girl Ever

6,046 views, 3 upvotes, 9 comments

Emma Watson offers to dress you as a woman

by unexpectednudeity

18,170 views, 5 upvotes, 1 comment

It's a bloke.

7,900 views, 3 upvotes

Emma Watson agrees to give you a m2f makeover

by unexpectednudeity

50,293 views, 4 upvotes, 3 comments

Blake Lively wants to give you a makeover

by unexpectednudeity

20,702 views, 3 upvotes, 1 comment

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NSFW

by whitefemalefan20192

422 views, 1 upvote

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