Imgflip Logo Icon

fun › crossdressing Memes & GIFs

A place for good ol' fun content that appeals to everyone! Humor, memes, gifs, and kittens are all welcome here. Reposts and politics are not welcome (try "repost" or "politics" instead).
fun
To post images in this stream, please .
Create your own stream

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
2,718 views, 10 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
31,830 views, 1 upvote
Check the NSFW checkbox to enable not-safe-for-work images
NSFW
1,593 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
35,261 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
23,449 views, 2 upvotes

Harry Styles "Rewriting the Rule"

27,444 views, 5 upvotes, 1 comment

Emma Watson picks out your clothes

by anonymous
69,356 views, 10 upvotes

Cross-Dressing Fail

10,709 views

Hard Timz

5,623 views
Check the NSFW checkbox to enable not-safe-for-work images
NSFW
361 views, 1 upvote

Emma Watson offers to dress you as a woman

by anonymous
79,820 views, 8 upvotes, 1 comment
by anonymous
33,909 views, 5 upvotes, 1 comment

Aniplay

40,648 views, 6 upvotes, 1 comment

Jennifer Aniston wants to play dress up

by anonymous
95,115 views, 6 upvotes
Next ›