in for a penny, in for a pounding

A sexualized version of "in for a penny, in for a pound." Means almost the same thing as the original saying but in a sexual context as aforementioned. In context, it references sex with or without protection (in this case, without), and since it was done before might as well double down and do it again regardless of the consequences.

This was used in Team Four Star's, Dragon Ball Z Abridged: Episode 60 Epilogue.

Bulma: "But after the first time, I just thought; well, in for a penny, in for a pounding."
Trunks: "Ahhh!"
Bulma: "And I really was."
Trunks: "AHHHHHHHHHHHHHH!"

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pretty penny

a significant amount of money, or a high price on something

I bet he paid a pretty penny for that new porsche - even the gas for it costs a pretty penny

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Wrinkled Penny

Slang term for anus.

I tapped into her wrinkled penny last nite.

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Penny Crygor

An extremely cute and loveable character from WarioWare. She admires her grandfather and wants to grow up to be a great scientist, though she also desires to become a famous singer.

Penny Crygor is the best WarioWare character.

Penny Lane

Famous Beatles song, also an alias one would use to hide their true identity.

See the movie "Almost Famous" as an example.

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pretty penny

a sizeable amount of money

That vase would fetch a pretty penny.

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ten-a-penny

A kind of thing or person that's cheap, or which you can find easily and in large groups.

Don't worry about that band, pop and emo scumbags are ten-a-penny now a days