Not a bet but a true story about one of my spontaneous pranks...
When I first moved to Florida back in 92, I was still skydiving a lot. An old skydiving buddy of mine from New York called to say he was coming to Florida on vacation and wanted to make a few jumps with me while he was here.
When he got into town I met him out at the drop zone along with his cousin Joe who was tagging along. My friend Perry and I made two jumps at the end of the day and before they headed back to Orlando, we had a few beers, when his cousin Joe pipes up; skydiving doesn't look all that hard to do? I said oh really? Why don't you make a tandem jump while you're down here?
He had a few beers and I knew that's what was doing the talking. They left and planned on coming back the next day. So the following day they show back up, and Joe had this shit eating grin on his face and proceeds to tell me he signed up for a tandem jump. I said that's great! I’ll be sure to get on the same plane load and follow you out in freefall.
While he was getting his instructions I started to walk over to him at the very end, and his tandem instructor Graham was a good friend of mine. He told Joe to meet in the classroom when manifest gave the thirty minute call for load twelve, so he could get "geared up".
As Joe and I were walking away he asked me what gear he would need. So in a serious straight face I said...You'll need to be fitted for a jumpsuit, helmet, condom, harness, gloves and goggles. He hesitated for a brief moment and then asked me, what’s the condom for? I told him that Pheonix-Zhills was the first drop zone in the country to institute a "safe" skydiving policy. At that time all you heard on the news was the risk of getting aids.
I explained to him that while not all of the time, on some jumps the experience can be so intense that you might accidentally have an orgasm in free fall. The condom was to protect the tandem master from any potential accidental spillage. He said oh, I never would have realized that with a smile on his face.
Hook, sinker and line.....
I ran into the gear store and bought a gag condom off of the counter. I then went to see Graham his instructor, and explained that Joe was aware he had to wear a condom on his first tandem jump. Graham just looked at me and shook his head in disbelief, but he knew me well enough to play along. About ten minutes later the call came out and in comes Joe through the classroom door.
Graham walked over to the wall of hanging jumpsuits and sized Joe up. He then reached down into his box of goodies and handed Joe the condom. With a confused look on his face, Joe asked where he would put it on. We instructed him to go to the bathroom and when he got back we would finish putting the rest of his gear on
At this point I did a 180 turn out the door. I know sooner made it out thirty feet and I dropped to the ground in tears, laughing so hard that I couldn’t breathe. No sooner was I on the ground when a bunch of my skydiving buddies come running over to see if I was okay. After I told them what was going on, three hundred skydivers on the DZ that day knew about the condom story. Only thing left was to make the jump.
We got the call to board the plane and Joe was white as a ghost. In the plane on the ride to altitude, he had this intense look of fear and dread. His knuckles where white and I could tell he was having difficulty breathing. Finally on jump run, we made our way to the open door. He looked out and froze in the door. He literally had to be pushed out the door. I gave them a few seconds head start and then exited the plane myself. I dove down as fast as I could to catch up with them. I came face to face with Joe in free fall, not more than a foot from his face. His eyes were bulging out and I knew he was in shock. I was sticking my tongue out at him and making stupid faces at him the entire time and I know he never saw me right in front of him for at least twenty seconds of that skydive.
At break off altitude I left right before they were meant to open their parachute. I spiraled down to the ground as fast as I could so that I could me him just as soon as they landed. It turned out that Joe had hyperventilated and passed out under canopy. The landing for them was a butt slider. Joe was lying on the ground, still in shock when fifty or sixty skydivers came running over to him. When he opened his eyes, another skydiving friend of mine who was standing right over his face yelled out to Joe, well?? did you cum? Joe simply mumbled, I’m not sure!
That day Joe left the drop zone never realizing that he was the butt of my joke. Fifteen years later I still run into old skydivers who were there that day and remember Joe Grimaldo the safest skydiver in the world!