Pleasure and Pain (Part 4)

Introduction:
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. “What?”
“My dick is in the way,” I said indicating my limp dick.
“So do something about it,” Jennifer replied.
“I got it,” Jillian said, once again coming to my rescue (doom?).
She started stroking my cock, and sure enough, after only a few seconds of her soft warm hands jerking my meat, my dick started to rise out of the way. “That’s a good boy,” she cooed at my penis, as if she were talking to it directly. Then to my surprise, she bent down and kissed it on the head.
My cock lurched, and Jennifer must have seen that as her signal because all of a sudden Webster was hurtling towards my nuts.
THWOCK!!!
The impact was deafening. The pain was blinding. My mouth popped open but no sound came out. I couldn’t even see my balls underneath the massive book that had just smashed into them.
I started to fall to the floor, but my balls were trapped underneath the dictionary. As they tried to pull free from their tormenter, my balls pulled the dictionary with them, and as I collapsed to the floor, the dictionary came with me, landing on my nuts for a second time.
As I groaned feebly, I heard the girls laughing at this. I saw them standing there giggling and furiously rubbing their bare pussies. They really seemed to get off on my pain. I guess I was glad that somebody was enjoying themselves.
Gingerly, I moved the dictionary off of my nuts and gently felt my balls to make sure they were okay. Other than being a bit swollen (and very painful to touch) they seemed to be fine. My inspection was interrupted by Jennifer gasping.
I looked up to see her fingers plunging in and out of her juicy snatch. Then with a scream, she jammed them all the way in and her whole body started thrashing about. Her orgasm was so powerful she practically collapsed to the floor. I can’t believe my own sister had cum from smashing my balls!
I just stared in awe at my sister’s spasming body as her juices ran down her thighs. It was definitely a hot sight, and I would have enjoyed it much more had my balls not been aching so much.
“If everyone is finished enjoying themselves,” Jessica began, her own fingers still lightly rubbing her cunt, “then it’s Jillian’s turn.”
@@@@@
Jillian got her first pain this time. And a level five no less.
“Soak a towel in water, twist it into a ropelike structure, and then have the strongest player smack it into your bare breasts for 45 seconds.”
“That actually doesn’t seem so bad,” Jillian said as she started to remove her bra; the last article of clothing anyone in the room was wearing. Her bra fell away, revealing a pair of perfect milky orbs, topped with two candy pink nipples. They looked like the type that were made for sucking.
“I’ll go get the towel,” Jennifer said as she headed for the kitchen.
Jillian didn’t think it would be too painful, but I knew differently. When I was younger and used to go to camp, often times after swim, I would be subject to ‘rat-tail snaps’ as they were known. One of the guys would smack his wet towel into my but. And even through my bathing suit, it still hurt. Jillian was going to be getting it on her sensitive bare breasts, and for 45 seconds. I found that I was looking forward to it.
Jennifer came back in with a bath towel that was twisted up and soaking wet. “Here you go Justin,” she said as she handed me the towel.
I took it from her and looked at Jillian who was staring at me apprehensively.
“Be gentle,” she said quietly as I approached her.
I had no intention of going gently. I wasn’t planning on killing her with it, but after all the pain I had received so far, I relished the idea of dishing out some of my own.
I drew my hand back, preparing for the first swing, and looked to Jessica, who had my stopwatch in her hand.
Her eyes flicked up to meet mine and she gave me a flirty grin. Then she pressed the button and said “go!”
The moment the word left Jessica’s mouth, my wrist flicked and the towel went zinging right into Jillian’s large right breast. It hit the nipple dead center and I watched in awe as ripples spread throughout her boob meat, causing the whole boob to reverberate with the blow.
Jillian was also in awe, but of a different kind. At the moment of impact, her mouth had formed an O and her hand had come up to clutch her breast. I guess she hadn’t been expecting it to hurt so much.
As she was moaning her pain and massaging her breast, I smacked the towel into her exposed left breast. She cringed and let out a small shriek as her other orb was exposed to the onslaught.
Now she was massaging both breasts.
“You have to move your hands for me to continue,” I said as I wound to the towel tighter.
“It hurts too much,” she pleaded, her teary eyes looking into mine.
I felt a little sorry for her, but a part of me was also relishing her pain. So I used the same card they had been using on me the whole time. “If we’re going to win the 100 thousand, you need to co-operate.”
She reluctantly moved her hands, and I whacked her right breast again.
“Ow!” she screamed out, and her hand instinctively came to clutch her injured breast again. But this time she immediately removed it.
After a few more hits, she was actually beginning to cry, and I softened my blows just a little bit. But not too much; we did after all have an audience, and I didn’t want to jeopardize our chances of winning that money.
I had just hit Jillian’s left breast with another blow when Jessica called time. By this point Jillian had tears streaming down her cheeks and her tits were bright red.
As soon as Jillian had called time, she started to massage them, trying to rub the pain away.
I was feeling very bold after this latest experience, and that’s what made me say what I said next. “I think I can help you with that pain a little,” I said to Jillian.
“How?” she asked through tear streaked eyes. “May I?” I said, indicating her breasts.
She eyed me warily for a second; after all, I was the cause of her new found pain. But after a moment she nodded her head and removed her hands.
I slowly moved in, and gently placed my hands on either side of her breasts. Then I moved my head in and started to suckle on her nipples. Jillian was startled for only a moment before she started to moan her pleasure.
“Ooohhhh, that does feel nice,” she cooed in pleasure. Her hands went to the back of my head and held me tightly as I feasted on her precious breasts. I switched from one to the other a few times before, hands still on my head, Jillian pulled me up and gave me a sexually charged kiss that almost blew the top of my head off. Her tongue was in a frenzy, exploring my mouth like a poison victim looking for the antidote. I groaned back into her mouth as I returned the attack, and for a good minute, we stood there making out like two lust crazed animals, which I guess is what we were.
“Ahem,” Jennifer finally said. We broke away gasping as we both looked at my sister. “Intermission’s over,” she said, a grin plastered across her face at witnessing our antics. “It’s my turn.”
@@@@@
Jennifer got another pleasure card. This time she rolled a 1. “Have a player of your choice do a sexy dance for 10 seconds.”
“What a rip-off,” she protested.
“Better than nothing, I guess,” Jillian said with a shrug.
“Barely,” Jennifer returned.
“You,” she said pointing at me. “Start dancing. And lots of pelvic thrusts. I wanna see your dick bouncing around.” Her tone was angry. I guess she felt she was being cheated. Well, there was nothing I could do about that.
Jessica said go, and I started dancing. I wasn’t very good, but it didn’t stop the girls from drooling over me. My dick swung, my ass shook, and the girls followed my every move with lust in their eyes. But almost as soon as I had started, it was over.
“That was so cheap,” I heard my sister mumble. “Only ten fucking seconds.”
“Okay,” Jessica said as she went to draw a card for herself. “Maybe I can provide us all with a little more entertainment.”
She drew a pleasure card, her third in a row. And this time the dice landed on six. “Have sexual intercourse with the player of your choice for two minutes.”
“Holy shit!” Jennifer exclaimed when she heard what Jessica had to do.
“I’m a virgin,” Jessica said softly, almost to herself, as she stared at the card.
I was too, but that wasn’t so strange. After all, I was only 13. But I wouldn’t be a virgin for long!
Without my even realizing it, my dick had gotten hard as an iron bar. My dick was anticipating sex with Jessica just as much as I was.
“I guess you guys should just do it,” Jillian said. And I could’ve sworn that there was a touch of jealousy in her voice.
“Yeah,” Jessica agreed, although her fear and trepidation were quickly being overtaken by animalistic lust. She actually subconsciously licked her lips as she turned to me.
“Where are we going to do it?” she asked, looking around the sparsely furnished office.
“Why doesn’t Justin sit on the computer chair and you straddle him,?” Jennifer suggested.
“Ok,” I said and took a seat in the chair.
As Jessica was walking over to me, her eyes suddenly flew wide open and she stopped short.
“I’m not on the pill,” she exclaimed.
“Uh oh. What do we do?” my sister asked.
“It’s only for like two minutes,” Jillian said. “You can keep yourself from coming for two minutes, can’t you Justin?”
“Yeah,” I said, thrusting my chest out in a manly pose. “I can handle it.”
“I’m still not sure,” Jessica said, biting her lower lip nervously as she stared at my dick, which was sticking straight up out of my groin.
“I looked at the uncertainty and lust that was warring in her eyes and played my trump card. “One hundred thousand dollars,” I said seductively.
Like a barrier had been broken, the tension in Jessica’s face melted away. “Oh, fine,” she said and walked right over to me and spread her legs. Her pussy was now directly over my raging dick. Maybe a foot was all that was separating me from heaven.
Jillian picked up my stopwatch. “You have two minutes,” she said. “Ready, go!”

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