"crossdressing" Memes & GIFs

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

by Veronicafordaddy

69,229 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

79,652 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

13,594 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

22,127 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

42,150 views, 4 upvotes, 1 comment

Captain Shakespeare shaking that spear

by heresyourgif

9,970 views, 7 upvotes

It's a bloke.

17,950 views, 3 upvotes

by Veronicafordaddy

28,812 views, 2 upvotes

Palletshipping Wet Dream

10,503 views, 3 upvotes

Blake Lively agrees to make you over

by unexpectednudeity

55,846 views, 2 upvotes

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

by unexpectednudeity

29,528 views, 2 upvotes

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NSFW

by unexpectednudeity

18,294 views, 3 upvotes

Traveling abroad....as a broad!

by BicycleRepairman

8,238 views, 1 upvote

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NSFW

by whitefemalefan20192

784 views, 1 upvote