When someone goes on vacation and asks you to check in on their house while they're away. Ex: water plants, feed pets, shovel the driveway.
"We're going away for a week. Can you do a Canadian break and enter and feed our dog?". It's based on the stereotype that Canadians are so polite that when the break into a house they do nice things for the owner instead of stealing items.
by Dr. Buttface III February 14, 2020
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something you say when you enter a discord general chat
thugshaker500: image of spongebob with the text, "a real nigga just entered chat"
femboylover9: shut the fuck up
by playboicartienjoyer1234 August 7, 2023
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After a girl has been cream pied by another male, you start fucking her pussy.
Dave: Yo Joe, my girl wanted me to enter the pearly gates after she got creampied by Quandale!

Joe: No way bro she must be for the streets

Entering the pearly gates: After a girl has been cream pied by another male, you start fucking her pussy.
by George Looney IV July 19, 2023
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From the web article: Joe Arridy was the happiest man on death row
...
"He is one of the worst Mental Defective cases I have ever seen," the officer wrote. "I picked him up this morning for allowing some of the nastiest and Dirtiest things done to him that I have heard of."

According to the officer, Joe had been "manipulating the penis of Negro Boys with his mouth" and allowing said boys "to enter the dirty road with their penis." ("I would be more technical," the officer explained apologetically, "but do not know the terms.") In another time, Arridy might have been deemed an at-risk teen who'd been sexually exploited by older youths. But in 1929, he was simply a pervert who had to be locked away.
by WhiteNip August 12, 2019
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you are bored go jerk of or something. do not enter word.
by down your t!! July 17, 2018
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When your penis is long you can wrap it round her leg and let it slide in her snatch.
Guy1: Hey man I swear she's not walking right.

Guy2: Yeah well don't tell anyone,but I over and entered her last night.
by Strange kid. Com December 3, 2016
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When the penis goes into the butthole or anus
Man dude, last night I went to enter the house and she was like, GTFO!
by Chainz in da Building July 17, 2015
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