Okay - you asked for parasailing stories! My two sons, then 9 and 10 went parasailing when we were on vacation (not WDW). They rode tandem and had the option of getting wet or not. They chose yes, and no matter how hard the boat operator tried, couldn't get them to go down into the water because they were too light. He even went backwards at one point but they just kept floating up there. He finally gave up and they couldn't get wet.
But the funny part was what happened after that. Where they did the parasailing, first you had to wade out in the water to a rowboat, then paddle the rowboat out to the powerboat, then get all hooked up and go out. We'd paid for them to have their picture taken ($5 for a polaroid) and when they came back to shore where we were waiting we asked for the picture and they said they'd forgotten to take one. I expected them to just give us our money back, but the supervisor came over and yelled at the operators and said this was the second time it had happened that day and that they were giving up their lunch hour to take them back out. So out to the rowboat, to the power boat, all hooked up, up in the air, take the picture, then everything in reverse! Pretty funny!
But they both enjoyed it, even the second time, and even though they didn't get wet! I'd just be cautious if it was windy that day.