Imgflip Logo Icon
HotNew

Crossdressing › crossdresser Memes & GIFs

A stream for crossdressers, drag queens, drag kings, femboys, and transvestites (as a reclaimed term). Allies and appreciators are also welcome.
Crossdressing
To post images in this stream, please .
Moderators
InvaderBethany OWNER DoctorEggman AlaskaNativeManitou ordinary-memer
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

Pokémon: Jessie and James dress up as nurses

Pokémon: Jessie and James dress up as nurses | 2, EPISODE 23 | image tagged in pokemon,team rocket,jessie and james,nurse joy,crossdresser,crossdressing | made w/ Imgflip meme maker
by InvaderBethany
336 views, 2 upvotes, 2 comments

Pokémon: Jessie, James and Meow perform Swanlake

Pokémon: Jessie, James and Meow perform Swanlake | 2, EPISODE 6 | image tagged in pokemon,team rocket,jessie and james,crossdresser,crossdressing,swan lake | made w/ Imgflip meme maker
by InvaderBethany
365 views, 2 upvotes

Pokémon: Jessie and James disguised as egg sellers

Pokémon: Jessie and James disguised as egg sellers | POKEMON SEASON 1, EPISODE 50: WHO GETS TO KEEP TOGEPI? JESSIE AND JAMES POSED AS FEMALE EGG-SELLERS WITH OLD-FASHIONED DRESSES, BONNETS, AND BASKETS FULL OF FAKE POKÉMON EGGS IN AN ATTEMPT TO STEAL THE TOGEPI EGG. | image tagged in pokemon,team rocket,jessie and james,crossdresser,crossdressing,togepi | made w/ Imgflip meme maker
by InvaderBethany
227 views, 2 upvotes

Pokémon: Jessie and James crossdressed in a style similar to the manga The Rose Of Versailles

Pokémon: Jessie and James crossdressed in a style similar to the manga The Rose Of Versailles | POKEMON SEASON 1, EPISODE 28: POKEMON FASHION FLASH; JESSIE AND JAMES CROSS-DRESSED IN A FASHION SIMILAR TO THAT OF THE MANGA THE ROSE OF VERSAILLES. | image tagged in pokemon,team rocket,jessie and james,crossdresser,crossdressing,manga | made w/ Imgflip meme maker
by InvaderBethany
216 views, 2 upvotes

American Dad: Roger crossdresses as an old woman

American Dad: Roger crossdresses as an old woman | AMERICAN DAD SEASON 1, EPISODE 5: ROGER CODGER; AFTER AWAKENING FROM A STRESS INDUCED HYBERNATION CYCLE, ROGER QUICKLY THROWS TOGETHER THIS DISGUISE AND A NEW ELDERLY WOMAN PERSONA IS BORN. | image tagged in american dad,roger,crossdresser,crossdressing,old woman | made w/ Imgflip meme maker
by InvaderBethany
205 views, 2 upvotes

Pokémon: Jessie and James disguised as hula girls

by InvaderBethany
211 views, 2 upvotes, 1 comment

American Dad: Roger disguised as Hayley Smith

by InvaderBethany
203 views, 1 upvote

Pokémon: Ash crossdressing as Ashley

Show More
by InvaderBethany
235 views, 2 upvotes, 2 comments

Pokémon: Jessie and James wearing a ganguro style disguise

by InvaderBethany
205 views, 2 upvotes, 2 comments

Femboys and Crossdressers are pretty cool

by InvaderBethany
219 views, 3 upvotes

High heels for men

by InvaderBethany
217 views, 5 upvotes

Using makeup to create cleavage

Show More
by InvaderBethany
191 views, 5 upvotes, 1 comment
Check the NSFW checkbox to enable not-safe-for-work images
NSFW
by InvaderBethany
125 views, 3 upvotes, 1 comment

Crossdressing bingo

by InvaderBethany
209 views, 4 upvotes
Next ›