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When you tickle one's butthole with a winking motion of your eyelash, while giving them a reach-around.'
ALSO
A bar inside the Elder Scrolls V: Skyrim game.
That skanky bitch just gave me the winking skeever last night, but the joke is on her cause now she has pink eye.
That whore took such a close look at my balloon knot, she damn near gave me a winking skeever.
{Skyrim} My character went into The Winking Skeever, paid a septim, and recieved the winking skeever and now has learned a new shout!
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A derogatory term for the anus of any living creature or similar depiction thereof.
Trey's winking skeever has seen many a hard man.
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Performing a butterfly kiss on the anus of your partner.
I think the pink eye came from when I was giving Carley a winking skeever.