Imgflip Logo Icon

"crossdressing" Memes & GIFs

Imgflip Pro

  • AI creation tools & better GIFs
  • No ads
  • Custom 6x6 profile icon and new colors
  • Your images are featured instantly in auto-approve-sfw streams
  • Your images jump to the top of approval queues
Go Pro
Check the NSFW checkbox to enable not-safe-for-work images
NSFW
2,952 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
35,038 views, 1 upvote
Check the NSFW checkbox to enable not-safe-for-work images
NSFW
1,646 views, 4 upvotes

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
37,530 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
24,384 views, 2 upvotes

Harry Styles "Rewriting the Rule"

28,413 views, 5 upvotes, 1 comment

Emma Watson picks out your clothes

by anonymous
72,391 views, 10 upvotes

Cross-Dressing Fail

12,009 views

Emma Watson offers to dress you as a woman

by anonymous
83,117 views, 8 upvotes, 1 comment

Hard Timz

6,324 views
Check the NSFW checkbox to enable not-safe-for-work images
NSFW
408 views, 1 upvote
by anonymous
34,638 views, 5 upvotes, 1 comment

Aniplay

41,487 views, 6 upvotes, 1 comment

Jennifer Aniston wants to play dress up

by anonymous
98,363 views, 6 upvotes
Next ›