While in the doggy style position you insert your Great toe into the woman's butthole without pulling your penis out of her vagina.
I think I got a Charlie horse giving your mother a Tampa Tip Toe last Easter.
by Leg Tat November 12, 2017
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When you’ve gone to the toilet and finished your business, just to realise there is no toilet paper. So you have to walk out the bathroom to gather more rolls with your pants down just below crack level hoping no stinky business gets on your fresh threads and for some reason your tip toeing carefully not to arrouse suspicion of any one in the house.
Friend- I completely forgot to check for toilet paper before going to the lavatory the other day. So I had the pull of the greatest ‘stanky tip toe’ past my room mate while they were having a kip on the couch.
by Mrstealyo_husky March 14, 2018
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The act of making love anally to someone with your toe and then having them suck the shit from your toe.
i shoved my toe into my wife's sister's ass, and had to Tokyo tip toe to avoid getting caught.
by PsychoLogic1989 January 19, 2018
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When two people meet, usually online in an online chat room, and through common hardships, life experiences, witty humor, and intellect fall in love. Both parties are madly in love, but for for one reason or another are afraid of telling the other party. The tip-toe rule is designed to keep one party from saying the words "I love you" at a time when both are emotionally vulnerable and are afraid from falling off an emotion cliff with no bottom. It is believed by respecting this boundary that these two people will be able to build a relationship meant to endure, and last the test of time.

The tip-toe rule is a rule deisgned and created by two people to protect their fragile relationship. Usually a fool-hearty decision because there are no guarantees of a tomorrow.
"Dexter sat down looking longingly at the object of his affection. His own recently jaded heart wanted to tell the woman of his affection that he loved her with all his heart, but was afraid of falling into the abyss from which he could never climb. In fact, in a series of bad comedies, he unknowingly threw himself down into the abyss by abiding by the tip-toe rule. To this day, Dexter has never been able to find his way out."
by Dexter Thorne August 24, 2017
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To work hard and be wary of right and wrong choices, usually used when discussing or describing work history and/or life choices.
MOM: "Your father and I have worked so hard trying to give you and your brothers the best life possible!"

DAUGHTER: " You don't think I don't know that!"

MOM: "You have no idea! We've both been Tip-toeing Around The Onions since birth for you!"

DAUGHTER: " Okay, Okay I get it, Jeez!"
by LastKARENnight April 3, 2012
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Often used to describe a man who is (often secretly) dating numerous women, or a man who is hooking up with more than one woman on any given night.

Can also be used to describe when a man is cheating on their girlfriend.
We just out here tip toeing on them hoes.

We headed to the club to Tip toe on them hoes.

Tyrone is such a man-whore, all he does is tip toe on them hoes.

Hey did you hear what happened last weekend, Jamal got caught tip toeing on his hoe.
by Jemaku August 15, 2012
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Made famous by Riff Raff the Rapper. The act of gingerly tip toeing in your beautiful crisp Air Jordans while the Tip Toe Wing in my Jawwdinz track plays in the background and full circle completion by shit sharing it to social media
Dude 1: yo, you copped them new LeBrons?
dude 2: c'mon man, you know everywhere I go I'm only tip toe wing in my Jawwdinz!
by DontHollaMyName November 7, 2019
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