"crossdressing" Memes & GIFs

Make a meme Make a gif Make a chart

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

WITH LEGS LIKE HERS; DO YOU REALLY CARE? | image tagged in crossdressing | made w/ Imgflip meme maker

by Veronicafordaddy

69,067 views, 6 upvotes

Emma Watson agrees to give you a m2f makeover

Emma Watson agrees to give you a m2f makeover | 😈💄💋👠; YOU WANT ME TO GIVE YOU A MAKEOVER AND TAKE YOU OUT SHOPPING AS MY GIRLFRIEND? SURE HON I’LL DO IT. IT WE BE FUN TO PUT YOU IN A SKIRT AND SHOW YOU OFF! | image tagged in emma watson,crossdressing | made w/ Imgflip meme maker

by unexpectednudeity

79,534 views, 6 upvotes, 3 comments

Ash Ketchum the Cutest Girl Ever

Ash Ketchum the Cutest Girl Ever | ASH KETCHUM COULD FOOL EVEN ISSEI HYOUDOU
WHEN HE CROSS DRESSES | image tagged in pokemon,ash ketchum,crossdressing | made w/ Imgflip meme maker

13,566 views, 4 upvotes, 10 comments

I'M TOO PRETTY; FOR MY SWORD | image tagged in final fantasy vii,cloud strife,trap,crossdressing,pretty boy,too sexy | made w/ Imgflip meme maker

by anonymous

22,100 views, 1 upvote

Blake Lively wants to give you a makeover

Blake Lively wants to give you a makeover | SWEETIE I REALLY WANT TO ASK YOU SOMETHING. WOULD YOU CONSIDER LETTING ME DRESS YOU UP AS A WOMAN? I MEAN GO ALL OUT. THE LACY UNDERWEAR, STOCKINGS, HEELS AND A NICE SKIRT AND BLAZER OR DRESS. GET RID OF ALL YOUR BODY HAIR FIND YOU THE PERFECT WIG AND DO YOUR MAKEUP SO WELL THAT YOUR OWN MOTHER WON’T RECOGNIZE YOU.💄💋👠; THEN WE CAN MEET SOMEWHERE AND YOU CAN PICK ME UP AND WE’LL GO HOME TOGETHER LIKE LESBIAN LOVERS 😍💄💋🌹 | image tagged in blake lively,crossdressing | made w/ Imgflip meme maker

by unexpectednudeity

42,068 views, 4 upvotes, 1 comment

Captain Shakespeare shaking that spear

by heresyourgif

9,938 views, 7 upvotes

It's a bloke.

17,908 views, 3 upvotes

by Veronicafordaddy

28,781 views, 2 upvotes

Palletshipping Wet Dream

10,477 views, 3 upvotes

Blake Lively agrees to make you over

by unexpectednudeity

55,738 views, 2 upvotes

Blake Lively happy to do your makeover and pleased with the results

by unexpectednudeity

29,475 views, 2 upvotes

Check the NSFW checkbox to enable not-safe-for-work images

NSFW

by unexpectednudeity

18,290 views, 3 upvotes

Traveling abroad....as a broad!

by BicycleRepairman

8,217 views, 1 upvote

Check the NSFW checkbox to enable not-safe-for-work images

NSFW

by whitefemalefan20192

783 views, 1 upvote