I don't know if any of you are into pranks, but if you are I'd love to hear some of your personal best!
Here's one I pulled twenty years ago when I first moved to Florida.
When I first moved to Florida back in 92, I was skydiving a lot. An old friend from New York who I use to jump with 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, I invited them back over to my place for pizza and a few beers. Then after a couple of beers, 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? You're in the perfect place to make your first skydive.
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 on the drop zone and Joe has a **** eating grin on his face and tells me that he signed up for a tandem jump. I said that's great! I’ll be sure to get on the same plane and follow you out in freefall.
While he was getting his instructions I started to walk over at the very end and his tandem instructor, Graham, a good friend of mine was telling Joe to meet him 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, gloves and goggles. He hesitated for a brief minute and then asked me what the condom was 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 think it was the Magnum super sensitive ultra ribbed giggler model. I then went to see Graham his instructor and explained that Joe was aware he was required to wear a condom on his first tandem jump. Graham just looked at me and shook his head in disbelief. 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 up Joe. 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 made it about thirty feet out of the building and I dropped to the ground in tears laughing so hard I couldn’t get my breath back. No sooner was I on the ground when about two hundred of my skydiving buddies come running over to see if I was okay. After I told them what was going on, all two hundred skydivers on the DZ that day knew about the guy who was getting ready to skydive while wearing a condom for his protection.
We got the call to board the plane and I have never seen anyone so terrified in my life, he 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 at 13,000 feet we made our way to the door. He had to be pushed out. I gave them a few seconds head start and then proceeded to dive down to them at 200 mph. I came face to face with Joe not more than a foot from his face. His eyes were bulging out and I knew he was in a state of shock. I was sticking my tongue and making stupid faces at him the entire time and he looked as though he couldn't even see me.
I turned and tracked away from them right before opening. I spiraled down under canopy to the ground as fast as I could. It turned out he hyperventilated and passed out under his parachute. The landing for them was a butt slider. He 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 a Brit yelled out to Joe, well did you cum? His 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!