Imgflip Logo Icon

"crossdressing" Memes & GIFs

Imgflip Pro

  • AI creation tools & better GIFs
  • No ads
  • Custom 6x6 profile icon and new colors
  • Your images jump to the top of approval queues
Go Pro
Check the NSFW checkbox to enable not-safe-for-work images
NSFW
3,130 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
37,047 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
38,890 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
24,952 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
29,023 views, 5 upvotes, 1 comment
Check the NSFW checkbox to enable not-safe-for-work images
NSFW
1,704 views, 4 upvotes

Emma Watson picks out your clothes

by anonymous
74,152 views, 10 upvotes

Emma Watson offers to dress you as a woman

by anonymous
85,223 views, 8 upvotes, 1 comment

Emma Watson agrees to give you a m2f makeover

by anonymous
84,858 views, 7 upvotes, 3 comments

Cross-Dressing Fail

12,499 views
Check the NSFW checkbox to enable not-safe-for-work images
NSFW
548 views, 1 upvote
by anonymous
35,035 views, 5 upvotes, 1 comment

Hard Timz

6,708 views

Jennifer Aniston wants to play dress up

by anonymous
100,561 views, 6 upvotes
Next ›