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The amount of payment you are willing to give to a cheap hooker with leprosy; how much you'd would give your best friend for a blowjob from them
"I payed Betty two pennies and a half smoked cigarette for a blowjob, but only got herpes out of it."
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A person who is a 1 on the 1-10 hot scale but has a great personality.
Yeah Kayla is ugly but she's a pretty penny.
When you get blackout drunk and end the night with a spectacular performance of Irish Yoga unbeknownst to you with your face firmly pressed against a shinny copper penny. Then proceed to present to work the next morning with said shiny copper penny still adhered to your massively hung over forehead.
April - Hey Caleb can I give you a penny for your thoughts?
Caleb - sure whats up?
April - never mind I see you already have one.
giving something so little effort that the words half-assed or quarter-assed don't do it justice, and only with the 1/100 denomination of the full effort (penny) can one comprehend the sheer lack of effort put in.
x: Dude has Edward done his part on the group final yet?
y: Yeah, he's done his part, but it was so penny-assed that we're gonna have to redo it.
Someone who refuses to spend money on anything other than necessities.
"Stop being a Penny Nose and lets go to the movies"
When a girl is lay'd on a table and 10 guys 5 on each side of the table. They then cum on her from the bottom to the top. Hens the term Ten Penny Tower.
Man we should totally Ten penny tower that chick!
Just like a Pretty Penny means a big amount of money, a Sexy Penny means an absolutely enormous amount of money, usually in the tens of millions or above.
Joe : “My Dad just bought a mansion worth £15 million.”
Jenny : “Wow... That's a Sexy Penny.”