The Fastest Cross-Dresser!

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I'm Surprised TSA Let Him Through

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Merman! *cough cough* Mer<i>man!</i>

Via fuckyeahdementia.com

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"SIR! REQUEST PERMISSION TO WEAR SEXY THIGH HIGHS SIR!"

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I Can't Tell What He's Proud Of

Created by Cyberkedi

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Lana Del Raymond

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The Man Looks Good in Pink, Whaddaya Want?

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Must Be Ladies' Night

Created by Snake73

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Enjoying the Zoo, Ladies? Dudes? People?

Via Reddit

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And That's Only His Workwear...

Created by Snake73

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Talk Dirty to Me. What Are You Wearing Right Now?

Via Fork Party

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Keep 'Em Covered!

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One of These Things is Not Like the Other

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Give Her Back Her Skirt, You Cruel Cruel Man

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Not Sure if Wig or Brain-Sucking Yellow Frog

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Someone Could Use a Bra

Created by amy

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