When a male attmepts to fellate himself however the extreme angles involved cause him to throw his back out, and he is stuck in that position until help can arrive.
Hey, Steve got caught in a Toledo Jackknife, again.
by Benevir August 19, 2007
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Most likely first used in the early 1900s, either refers to a sarcastic remark about Toledo, Ohio or originated from a realistic remark of the Holy city of Toledo, Spain. It is now used as a phrase, by Americans, if something is unbelievable, disturbing, or blows their mind. See blow your mind
Woman- Did you read in the newspaper that a grandpa got run over by his own car by a homeless bum he paid to fix it, and then the bum took off with it?

Man- Holy Toledo?! That's like "Grandma Got Ran Over By a Reindeer" only a hundred times worse!
by DeJo August 2, 2005
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The Toledo Tablecloth is primarily used to score revenge or payback and is similar to a Texas Doily. The Toledo Tablecloth is best deployed over an end table or other small decorative table. Once deployed, a rapid exit from the location where it has been laid should be made so as to leave the tablecloth behind for furture discovery.

To create The Toledo Tablecloth, an individual must shit their grunders, aka underware intentionally, or use grunders that have significant skid marks, mud tracks or shit stains. To create the "tablecloth", take the underware off and turn them inside out making it a point to retain as much fecal matter as possible. Next, stretch the waistband opening around the edges of an end table or other small decorative table and pulling the band down the sides. Fold the legs of the underware over to the side so as to cover any exposed top of the table. Be sure to leave the shart stain as close to the middle of the table top as possible. Center as best as possible. Leave quickly for discovery by others.
Unfortunately, Roger got off from work early and decided to drop by his girlfriend Mary Ann's house and surprise her. To Roger's dismay, he crept in only to find Mary Ann having sex with her neighbor Carl. Roger walked in just as Carl was diggning in the garden. Rather than becoming enraged, Roger did not disrupt their doggie style play and left the room. He copped a squat in the living room and laid a fresh, wet shart in his grunders. He then created The Toledo Tablecloth on Mary Ann's brand new Rooms To Go end table. He quickly left the house so he could clean up his sticky crack corn at a nearby 7-11.
by Eaton Holgoode February 20, 2014
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1. The act of a man not washing his penis for two years. He can accomplish this by covering his genetalia with a shower cap when he bathes, leaving a condom or balloon on his penis at all times, or by just skipping washing himself altogether. Once his penis is especially filthy and overgrown with mushrooms and other molds, and his pubics an enchanted forest full of woodland creatures, he will have unpretected intercourse with a lady. If all goes well, the animals populating his pubic region will leap onto the fur of the man's partner, thus spreading the fun and the funguito to as many people as possible.

2. The act of a man collecting his semen in a bowl or other dish for several months. Once he has a good amount built up (2 cups or so), he will leave it in a damp, warm, dark area for upwards of two years. When he uncovers his treat, it should have a thick, green, mossy coating on the top. He will then scoop as much of his fungusy prize as he can into his dominant hand, spring on an unsuspecting lady, and throw it into her welcoming face. If he chooses, he is welcome to say something victorious along the lines of, "You've been Funguitoed!" to the victim.

A member of the "Holy Toledo Trinity", along with the "Toledo Burrito" and the "Toledo Mosquito".
"Did you hear about Terry? He pulled off a Toledo Funguito this weekend. Apparently he's been jerking off into a bowl and wearing a shower cap over his penis for, like, two years."

"Weird."
by The Earl of Teabag August 27, 2006
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On May 25, 1085 Alfonso VI of Castile kicked the Moors out of Toledo, Spain; after which Toledo became one of the great centers of Christian culture. Hence the nickname "Holy Toledo". It has since evolved into an exclamation exhibiting surprise, probably due to original surprise that a Moor-encrusted place could become Holy.
Jimmy: Hey John! Did you know that Captain Kirk just beat Wolverine?
John: Holy Toledo! No Way!
by MidnightCricket May 1, 2009
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1) A prolapsed rectum. (aka. trunk butt)
2) When one masturbates a penis using ones prolapsed rectum.
1) Hey check out my Toledo sleeve.

2) I just gave my boyfriend the Toledo sleeve.
by Michael Reno Ewart October 14, 2009
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Pretty cool people who act like creepers most the time. But volunteer a lot with education, conservation, community service, and other random things at the Toledo Zoo and some off grounds places. Again, their pretty cool kids(:
"I wanna be a Toledo ZooTeen?"
"Why?"
"'Cause their the coolest kids in town."
by ZooTeen 4 Ever((: January 3, 2010
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