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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).
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WITH LEGS LIKE HERS; DO YOU REALLY CARE? | image tagged in crossdressing | made w/ Imgflip meme maker
by Veronicafordaddy
69,701 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
79,973 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
by AshisGod25
13,663 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
22,204 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
42,382 views, 4 upvotes, 1 comment

Captain Shakespeare shaking that spear

by heresyourgif
10,037 views, 7 upvotes

It's a bloke.

by Alyssia1982
18,067 views, 3 upvotes
by Veronicafordaddy
28,900 views, 2 upvotes

Palletshipping Wet Dream

by fan21
10,560 views, 3 upvotes

Blake Lively agrees to make you over

by unexpectednudeity
56,113 views, 2 upvotes

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

by unexpectednudeity
29,665 views, 2 upvotes
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NSFW
by unexpectednudeity
18,302 views, 3 upvotes

Traveling abroad....as a broad!

by BicycleRepairman
8,295 views, 1 upvote
Check the NSFW checkbox to enable not-safe-for-work images
NSFW
by whitefemalefan20192
787 views, 1 upvote
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