when your standing in the shower and you rub butts with your g/f and it just feels odd and really slippery.
she bends over for the soap and instead ramming your penis in her butt, you turn around, push your butt against hers and jolly roger the shit outta her.

Tip: hold her hips she she can't run away and rub vigorously!
Jolly Rogering is fun for anyone
by BostonStrangler22 August 11, 2008
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the act of giving a really good friend head on a balcony, a showing of true friendship
“Hey! I was just giving my balcony bro a good Jolly Roger!”
by TimmyRog November 16, 2021
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The act of ejaculating in someone's eye, thus causing one eye to shut. Variations include saying "Arrr!" immediately after the eye closes to ensure proper scoring.
"I missed her mouth and inadvertantly gave her a Jolly Roger"
by Potty McNugg February 22, 2006
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Double-fisting so that the arm going into the vagina and the arm going into the anus are crossed. For effective movement, the crossed arms are held just below the head, thus creating the "Jolly Roger" similar in resemblance to the infamous buccaneer flag.
Avast matey! Let's head to the crows nest and strike the Jolly Roger!
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Another name for the skull & crossbones symbol.
"My Halo 2 character has a Jolly Roger symbol on his shoulder."
-me
by Dave December 31, 2005
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jol-ee roj-er

-part of speech: noun
-origin: Pittsburgh, Pennsylvania, USA

1. the act of receiving a blowjob and ejaculating in a person's eye, thus making them squint and shout, "RRRRR" like a pirate;

usually performed after a Pittsburgh Pirates' victory, when television broadcaster Greg Brown says, "Raise the Jolly Roger!"
1. That was a great game tonight! I can't wait to go home and get a Jolly Roger from my wife;
2. Goddamn it, the Pirates lost again tonight. Their losing streak is now at 8 games. I haven't gotten a Jolly Roger in over a week... my balls feel like they are gonna explode.
by J McPott October 8, 2010
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