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Cross Dressing Cartoons and Comics

Cross Dressing cartoon 1 of 150


Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

"My mistake, really. I thought your ad said you were into cross-training."

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Cross Dressing cartoon 2 of 150


Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

"Last year it was backgammon."

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Cross Dressing cartoon 3 of 150


Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

I'm Proud of my Gay Son!....I'm Proud of my Cross-Dressing Dad.

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Cross Dressing cartoon 4 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

As Jeff cycled up the hill he realised he was in the wrong gear.

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Cross Dressing cartoon 5 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

'How can people say that we aren't a diverse group, we might LOOK the same but I happen to know for instance that Gerald wears a basque under his suit,'

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Cross Dressing cartoon 6 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

'Your car keys are under the sofa, and you like to wear women's shoes.'

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Cross Dressing cartoon 7 of 150

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'It's outrageous to be labelling people 'bonkers' in this day and age...put this one on instead.'

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Cross Dressing cartoon 8 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

'How about these overalls?'

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Cross Dressing cartoon 9 of 150


Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

“I’d lose the dress.”

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Cross Dressing cartoon 10 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

'You obviously misunderstood when I said this office had a dress code, Mr. Harkness!'

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Cross Dressing cartoon 11 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

'Colin was at the very bottom of a steep learning curve where internet dating was concerned,'

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Cross Dressing cartoon 12 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

'I know we don't have a formal dress code, but I think you're pushing the envelope, John.'

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Cross Dressing cartoon 13 of 150

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'That's not what I meant when I said you need to show more backbone.'

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Cross Dressing cartoon 14 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

'Darling, what's HAPPENED to us?'

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Cross Dressing cartoon 15 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

Fisherman to friend in dress: 'That's not what I meant by setting your drag.'

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Cross Dressing cartoon 16 of 150

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"What is this, Hank? Some sort of midlife crisis?"

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Cross Dressing cartoon 17 of 150


Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

"You've got one of my dresses on again."

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Cross Dressing cartoon 18 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

'I think you might have put that in the wrong place.'

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Cross Dressing cartoon 19 of 150

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'You think you have problems! Try being a male ladybug.'

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Cross Dressing cartoon 20 of 150

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'...I really wish you would of told me you wanted to be a ballerina before we got married.'

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Cross Dressing cartoon 21 of 150

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'He's our son, Roger. If he feels like a queen trapped inside a drone's thorax, then he feels like a queen trapped inside a drone's thorax.'

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Cross Dressing cartoon 22 of 150

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"Clark...is there something you'd like to tell me?"

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Cross Dressing cartoon 23 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

After an argument they always kissed and made up.

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Cross Dressing cartoon 24 of 150

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Cross Dressing cartoon 25 of 150

Cross Dressing cartoons, Cross Dressing cartoon, funny, Cross Dressing picture, Cross Dressing pictures, Cross Dressing image, Cross Dressing images, Cross Dressing illustration, Cross Dressing illustrations

Woman at party spots man wearing identical dress and wonders...'could this be Mr Right?'

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