The contest was simple. One would lead, the other follow. At each available opportunity, each would pull a stunt. If you were leading and bailed or crashed, you lost. If you were following and couldn't do the same stunt or better, you lost. After the first run all the way around the mall parking lot, they'd switch off leading and following. If no one had lost by the end of the second lap, the crowd would decide.
Derek led, and Jon followed. Derek started with a simple grind on the guardrail, which Jon followed with a Darkslide. Everyone started cheering Jon on, as no one wanted to see him in drag anymore, nor did they expect him to win. Everyone loves an underdog...
An ollie, a wallride, and a 20 yard manual later, Derek was starting to worry. Sure, he wanted to help Jon out of his predicament, but his pride was on the line. No one in town had ever outskated him. Thinking quickly, as they were approaching the starting point, he decided to risk it all on a tricky combo. He ollied up to a flowerbox along the old empty fountain, did grind and switched to the inside, landing in a manual in the fountain. Going up the inside of the fountain, he did a handplant at the rim, and back down. He transferred out of the fountain with a double kickflip, landing it perfectly at the start point.
Jon, just a few yards behind, and blowing everyone's mind by throwing 360's into the mix, followed closely. He replaced the handplant with the famous 900, and went for a triple kickflip on the transfer.
Disaster struck as his trucks broke at the landing. Jon landed on his ass, and was amazed that it didn't hurt more than it did, until he realized that his clothes fit a lot better, and his butt was a lot more padded.
Fortunately, he could still feel the tightness in his panties that indicated he was still all male where it counted.
Everyone was just staring. Jon was too stunned by his new predicament to move.
"Oh well," Jon thought. "At least I don't have to worry about looking so silly."
