Poorly Dressed

crossdressing

Crossdressing and keeping it fresh and new. These jokes and puns jump barriers and stigmas so open your mind and embrace true creativity in fashion.

You Getting Ready for a Bridge Game?

crossdressing dress - 4214796032
By bender0927
Comments

Untitled

bra crossdressing glasses nerd panties - 4018277376
By Unknown
Comments
Advertisement

One Was Bad Enough

beard costume crossdressing dress man - 5935688704
By Unknown
Comments

Rejected From the Mary Poppins Section of the Opening Ceremony

crossdressing dress mary poppins skirt what - 6475911680
By Unknown
Comments

Something Seems Wrong Here...

corset crossdressing dude hair nose ring - 4190141440
By Unknown
Comments
Advertisement

Kids Do the Darndest Things

bikini crossdressing eww kids parenting - 4290439168
By mcveyla
Comments

Ms Luscious Leather

crossdressing leather underwear - 5002737408
Via Izismile
Comments

Nice Cans

beard boobies crossdressing package skirt wig - 4310453504
By cyanidemartini
Comments
Advertisement

Oh No, How Did You Find My Secret Lair?

corset crazy crossdressing eww wtf - 4230541056
By Unknown
Comments

Real Cheap, We Swear

crossdressing get a shirt skirt - 6097505792
By Unknown
Comments

He Called Himself Kotton Kandy

bra crossdressing eww fanny pack fishnets - 4250099200
By dpo1013
Comments
Advertisement

Untitled

attitude crossdressing hair yellow - 3922970368
By Unknown
Comments

God Save the This Guy

crossdressing england olympics shirt UK union jack - 6479190784
By Unknown
Comments

You Scared Mrs. Sasquatch

beard crossdressing long hair skirt - 4289846272
By Unknown
Comments

Bye-Bye Kitty

best of week crossdressing g rated Hall of Fame hello kitty poorly dressed public transportation Subway - 6498025728
By Unknown
Comments

Who Is He Trying To Seduce?

costume crossdressing hotel lame - 5977868032
By Unknown
Comments
1 2