"crossdressing" Memes & GIFs

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Emma Watson picks out your clothes

Emma Watson picks out your clothes | YOU LIKE MY GOWN? I KNEW YOU WOULD. THERE’S ONE IN YOUR SIZE ON THE BED ALONG WITH ALL THE UNDER THINGS YOU’LL NEED, PICK OUT A PAIR OF SHOES AND GO GET DRESSED THEN WE’LL DO YOUR MAKEUP SWEETIE 💄💋👠 | image tagged in emma watson,crossdressing | made w/ Imgflip meme maker

by unexpectednudeity

62,674 views, 10 upvotes

Emma Watson offers to dress you as a woman

Emma Watson offers to dress you as a woman | HONEY, WOULD YOU CONSIDER LETTING ME DRESS YOU UP AS A WOMAN? WE COULD GO FOR COFFEE AND GO SHOPPING FOR GIRL CLOTHES FOR YOUR NEW WARDROBE .💋IT WOULD MAKE ME SO HAPPY! 😱SHOULD I TELL HER THIS HAS BEEN MY FANTASY FOR EVER! | image tagged in emma watson,crossdressing | made w/ Imgflip meme maker

by unexpectednudeity

74,951 views, 8 upvotes, 1 comment

Captain Shakespeare shaking that spear

by heresyourgif

9,211 views, 7 upvotes

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

by Veronicafordaddy

63,468 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

77,830 views, 6 upvotes, 3 comments

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

NSFW

1,972 views, 6 upvotes

Aniplay

by LuciferMogarCinderblaze

38,229 views, 6 upvotes, 1 comment

Jennifer Aniston wants to play dress up

by unexpectednudeity

86,656 views, 6 upvotes

Harry Styles "Rewriting the Rule"

25,174 views, 5 upvotes, 1 comment

by anonymous

32,099 views, 5 upvotes, 1 comment

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

NSFW

1,276 views, 4 upvotes

Ash Ketchum the Cutest Girl Ever

12,866 views, 4 upvotes, 10 comments

Blake Lively wants to give you a makeover

by unexpectednudeity

40,661 views, 4 upvotes, 1 comment

Palletshipping Wet Dream

9,808 views, 3 upvotes