to masturbate to full extent and make your pencil (penis) sharp (erect)
Once I saw that hot ass chica, I started to sharpen my pencil, asked her to come in the car, and then it was all good times.
by Eric Cartmanez May 9, 2008
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An act of sexual mutilation where a woman places a razor blade between her breasts prior to the act of titty-fucking.
"You still looking at getting circumcised?"

"No need. A girl surprised with a Glaswegian Pencil Sharpener last weekend."
by Quinterious December 12, 2020
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To masturbate, specifically during night time.
Pauly:" That's Killian, our roommate, but we like to call him the one handed gardener."
Joanie: "Why ?"
Pauly: "Beause we hear him sharpen the fields at night."
by ChaosBearer July 13, 2015
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Pencil Sharpening Day is an international Holiday, taking place on October 27th, which was recently popularized by the Youtuber cs188.

While the true origin of this annual holiday is unknown, experts believe that it originated in the middle ages, when feathers that were used to write bibles were thrown onto a pile and then were all sharpened on pencil sharpening day.

There is also rumored to be another Pencil Sharpening Day in November, which could not be confirmed, though.
by RacerN2O December 7, 2016
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to become more aggressive.
Get that mimosa out of your hand, and sharpen up!
by frank June 21, 2004
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(1.) To masturbate into the back of your 60-pack crayola crayon box.
I'm going to sharpen your crayon...ONE HANDED!
by CLAIREDEANDESIREE August 13, 2007
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