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Random
The act of fucking someone with their own penis.
Sambo hated shemales so he went and started chiliwinking the one with the penis hanging out of the skirt but to his surprise they enjoyed it.
When you rip a part of someones body off and fuck them in their own ass with it.
Lorena Bobbit planned on chiliwinking her husband but just ended up throwing his severed penis out the window.
Chiliwink: To remove someones body part and proceed to shove it up their own ass.
You better quit pointing at me with that finger before I chiliwink your ass with it!
When you ask an employee of a store if something sold out on the shelf is available in the back, they say no, you then go home to see it is in stock online and available in the back so you return to the store and rip that employees dick off and shove it in their own ass while picking up the product that you originally came to the store for.
Is this item available. No. Well could you please go check in the back because I do not want to have to return later and CHILIWINK YOUR ASS!