THE BETTING SAILOR (Taken from FunnyBone)
There once was a young sailor who couldn't resist a bet. He would make a bet on anything and he would always win. His shipmates were continually losing their money to him, making them very irritated. The Captain decided to have the boy transferred to another ship.
The next day the boy was transferred, and less than 15 minutes after boarding the ship, the boy addressed his new Captain and bet him 50 dollars he had hemorrhoids. The new Captain had just gotten a physical and knew he had no hemorrhoids, so he agreed to the bet.
The boy told his new Captain to drop his drawers and bend over. The Captain did so, and when he bent over, the boy shoved a broomstick up the Captain's ass. The sailor found no hemorrhoids and paid the Captain 50 bucks. The new Captain thought this was great and wanted to call the boy's old Captain and tell him. When he got the old Captain on the phone he told him he had just taken 50 dollars from the boy.
The old Captain replied, "How?"
"Well," explained the Captain, "he bet me I had hemorrhoids. I knew I didn't so I bet him. He told me to drop my drawers and bend over. When I did, he shoved a broomstick up my ass. Hey, no hemorrhoids. Fifty bucks I won."
The old Captain shouted, "That son-of-a-bitch! Before he left here he bet me 500 dollars that within an hour he would have a broomstick shoved up your ass!"