Shirt Tailed

When wiping and you accidentally use the back of your shirt to wipe your ass, leaving a skid mark or a tail. This is usually done when wearing a dress shirt. It is always unintentional

Although I have never personally done this, I do believe it to be theoretically possible and it has likely happened at some point in human existence.

I need to go home, I just shirt tailed myself in the men's room.

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Shirt Tailing

When a man is having rapid intercourse with a woman and another man sticks his dick to the first mans dick (side) and the force from the first dick pulls the second dick into the woman along with it.

Harry: Last night I went into Dave's room while he was fucking his girlfriend and I started shirt tailing myself in.
Dave: Yea dude, what was up with that?
Harry: You shouldn't have left an opening.

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Shirt tailing

Admiring someone so much that you fully imitate the persons style, talk, way of being.(cloning the person)

Son says to mom; Have you noticed travie shirt tailing me.

shirt tail lifter

1.A gay man
2.A brittish insult

"Allan Cummings.. he's a shirt tail lifter aint he!"
"you're a rite shirt tail lifter man"

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sleeping on his shirt tail

When someone is late and they were most likely just late because they were cuddled up in bed with their s/o.

“Where is Fido?”
“His wife was sleeping on his shirt tail, he’ll be here in a few minutes.”