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"crossdressing" Memes & GIFs

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Check the NSFW checkbox to enable not-safe-for-work images
NSFW
3,066 views, 11 upvotes

house cleaning

house cleaning | NEED CLEANING? I CAN'T UNDRESS UNTIL I CLEAN 3 HOUSES. | image tagged in crossdressing | made w/ Imgflip meme maker
36,281 views, 1 upvote

Stealing Mom's Shorts

Stealing Mom's Shorts | WHEN YOU STEAL YOUR MOM'S SHORTS; AND SHE SPRAYS YOU WITH THE HOSE | image tagged in summer,crossdressing | made w/ Imgflip meme maker
38,374 views, 1 upvote

Ash ketchum crossdress maid prof oak

Ash ketchum crossdress maid prof oak | image tagged in ash ketchum,crossdressing,professor oak,maid | made w/ Imgflip meme maker
24,717 views, 2 upvotes

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
28,744 views, 5 upvotes, 1 comment
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NSFW
1,673 views, 4 upvotes

Emma Watson picks out your clothes

by anonymous
73,552 views, 10 upvotes

Emma Watson offers to dress you as a woman

by anonymous
84,425 views, 8 upvotes, 1 comment

Cross-Dressing Fail

12,300 views
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NSFW
509 views, 1 upvote

Hard Timz

6,544 views
by anonymous
34,869 views, 5 upvotes, 1 comment

Aniplay

41,804 views, 6 upvotes, 1 comment

Jennifer Aniston wants to play dress up

by anonymous
99,783 views, 6 upvotes
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