Treehouse Sleepover Dares

by Rich
(Miami, FL)

When I was age 9 through 14 or so, my friends and I would have sleep overs at my friend’s treehouse. Our game of choice was always Dare. (We did not provide an option for Truth).


For each round, we would rotate who the dare master would be. That person would come up with the dare that the loser would have to do. Then we would play Uno. The winner of each game would become exempt, and we would keep playing until all but one person had won. The remaining person would have to do the dare.
As a result, there was a chance that the dare master would have to do his own dare. This created a dilemma since you would want to make it hard for someone else but would not want to make it so bad if you ended up being the one to have to do it.

The fun of the game was to figure out creative ways to inflict pain without causing injury, come up with creative ways to embarrass our friends, and figure out ways to put our friends at risk of getting caught. All dares were performed while wearing only your underwear. There was a rule that no one could repeat a dare that had already been used, so over time the dares became more creative and risky.

Here are some of the more memorable dares I had to do.

I had to stand with my back to my friends. I then had to pull my underwear down slightly to expose my butt, and allow each player (4 total) to shoot a rubber band at my backside at close range. That smarted.

I had to stand facing the treehouse wall and press a quarter against the wall with my nose. The quarter was placed at a spot that was high enough that I had to stand on my tip toes. Also, I had to hold my arms out straight from my sides and hold a rock in each hand. I had to hold the position for seven minutes. It’s amazing how quickly this position can cause muscle pain in the thighs, lower legs, and shoulders.

In the front yard, I had to lie on my stomach. My wrists were taped together behind my back and my ankles were taped together. I then had to do the worm across the yard. Fortunately, I got through this one with no neighbors passing by.

I had to stand under a tree branch and poke a hole in the back of my underwear, just under the waistband. I then had to run a clothes line chord through the hole. The chord was tossed up over the tree branch and hung down in front of me. I then had to pull on the chord until either the back of my underwear reached above my head or the waistband ripped completely off. That was the only wedgie I have ever experienced, but it was for real. I wasn’t able to get my underwear high enough, so I eventually raised my feet, which had my entire weight supported by the chord and my underwear. At that point, the waistband ripped off quickly.

In the front yard, I had to tie a thick piece of twine around my privates and run the other end of the twine through my fly. A friend tied that end around the trunk of a small tree. My wrists were then taped together behind my back. As a result, I had no way to hide or untie myself if anyone was to pass by. I had to be in that situation for ten minutes. As it turned out, a car did drive by. The driver slowed down and looked at me, but didn’t stop or say anything. Worse, however, was that my older brother and a couple of his friends drove by. They stopped and made fun of me. They threatened to pour stuff over me or take pictures to blackmail me but fortunately didn’t actually do anything.

In looking back, this seems kind of ridiculous; however, as 9 to 14 year old boys, we thought this stuff was really cool.

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Feb 16, 2016
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Fun best of collection
by: Francis

Rich, thanks for sharing your memories! I really like how you told the stories and can imagine how much fun you must have had as kids!

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