Pleasure and Pain (Part 4)

A gentle nudging of my shoulder woke me from a most wonderful slumber. “Justin,” my sister said. “Wake up. It’s your turn.”

I opened my eyes to see my sister crouching in front of me. My eyes were instantly drawn to her pussy, which was spread wide open from the position she was in. It glistened a healthy pink. She noticed where my eyes were looking and blushed before standing up.

“Yeah, okay,” I said after a moment. I didn’t really feel like moving but I guess I didn’t really have a choice.

Rising to my feet, I headed over to the computer and clicked on the action card. It flipped over to reveal pain. It seems my fun was over for the time being.

When I rolled the dice the number 4 came up.

“Take your testicles and place them on a hard surface such as a table and then have another player smash them with a hardcover book. Your penis must not get in the way or the process will be repeated.”

“I wanna do it,” Jessica said with determination. “To get back at him for cumming in my face.”

I gulped audibly. Thus far we had been playing for a chance to win the money. But now it seemed like Jessica wanted to get revenge. It seemed like she actually wanted to hurt me. I didn’t want to have that happen.

“Actually,” I said, speaking up, “I’d rather one of the other girls did it.”

Jessica frowned at that. “Whatever. I’m sure I’ll get another chance to bust you later.”

“So who do you want to do it?” Jillian asked.

Even though my balls weren’t hurting from round 1 anymore, I still remembered how much it had hurt at the time. I wanted to diminish any anguish I might have to experience. So on the one hand there was my sister, who being my sister would potentially go easy on me. On the other hand, Jillian had a major thing for me and she might go easy on me for that reason. In the end I chose Jennifer. She was family. She’d take it easy on me, right?

“Okay,” she said as she headed over to the bookshelf. There were a lot of books on the shelves, and several of them were hardcover. I figured she would take one of the ones from the middle shelves; one of the novels my father liked to read. Instead she reached for the bottom shelf and brought out Webster’s unabridged dictionary. All 1100 pages of it.

I guess I was wrong about her taking it easy on me. “I think that’s a bit extreme,” I said. “Why don’t you take one of the smaller ones?”

“This fit’s the criteria,” my sister replied as she struggled to bring it over to where I was standing. It must have weighed over 20 pounds.

“What should we use as a hard surface?” Jessica asked gleefully.

“Here,” Jillian said as she walked towards the end table next to the couch. She moved the lamp off of it and brought it over to where the rest of us were standing.

“Put your balls up there squirt,” Jennifer said.

I refused to comply.

“Oh for heavens sake,” Jennifer said rolling her eyes. “Jillian, get his nuts up on the table for me will you?”

“Sure,” Jillian said as she reached for my low hanging balls.

Even though I didn’t want her to come near me, I let her do it anyway just so that I could feel her handling my balls. My joy was short lived however, because a moment later my nuts were resting on the table and her hand was gone.

Jennifer was just raising the book up to give my balls an almighty smashing when I shouted out “wait!”

She paused mid swing.