The bet was that Jim couldn't make it through the park without being recognised as a man. Jim stood to win $1000 from all the guys in the bar.
Jim chose to go as a smart business woman, he reasoned that he would blend in with the women from the local offices having a lunchtime walk.
Halfway through the park Jim had to rest, the heels were hurting his feet.
As he sat there a man walked up and complemented him on his legs. Jim looked up but said nothing. He wasn't sure how to react, and he couldn't speak because it would give him away.
He looked the other way and adjusted his skirt.
The man sat down next to him.
"Stockings - nice."
Jim looked down and saw the top of his thigh exposed. He pulled the skirt down and walked off as quickly as he could. Not far now and the $1000 would be his, but there was this guy following him.
As he got to the edge of the park his pals were watching him, and as he passed through the gates of the park he turned round and told the guy following him to fuck off in his manliest voice.
His friends fell about laughing as they all drove away leaving the man amazed and Jim $1000 better off.