Pleasure and Pain (part 3)

Introduction:
It was my turn again and I was nervous as Hell. I didn’t have much choice though did I? Not if I wanted to win that hundred thousand. With only a moment’s further hesitation I clicked on the card and watched it turn over.
I visibly sagged with relief when I saw it said pleasure.
“There you go Justin,” Jillian said supportively as she clapped me on the shoulder.
I rolled the dice. 2. Crap. Well I suppose any number on a pleasure card was better than pain.
“Have a player of the opposite gender give you a nude back massage. You must lie on your stomach and they must sit completely nude on your butt. This activity lasts for one minute.”
It may have only been a 2, but it didn’t seem so bad.
I looked at the three girls. Jessica was still the only one that was completely clothed. I needed to change that.
“Jessica,” I said pointing at her. “I want you to give me the massage.”
“You just want me out of my clothes,” she said with a smirk as she started to undress.
I watched raptly as she first removed her shirt and then her bra, exposing her fantastically large knockers.
Then she slipped out of her skirt and panties before kicking her shoes off. She did it all so fast that I didn’t really had a chance to appreciate her nakedness before she told me to lie down. I guess there would be plenty of time for me to stare at her later.
As I lay down, I was careful not to bang up my swollen nuts on the hard wooden floor. I rested my head on the back of my hands as I felt Jessica sit on my ass.
Her pubic hair tickled and scratched my butt as she wiggled around looking for a comfortable position.
I felt my dick start to stiffen again. This was not a good time to be getting a woody. Being crushed up against the floor the way it was, it had no room to grow.
“Ready, and go.” Jennifer started the clock and Jessica started my massage.
I’m guessing she didn’t have much experience giving massages, but it felt nice just the same. Just the idea of a hot naked girl rubbing her hands all over my body was quite pleasant. And the fact that she was starting to rub her groin back and forth along my ass only heightened my pleasure (and hers I’m sure).
As she worked, her hands crept from up near my neck down towards my lower back and then to the top of my ass. When she started to gently knead the top of my ass cheeks I felt my dick begin to stir again. I was beginning to wish that we had a couch in here. For the last 30 seconds of the massage, I had to split my focus between the pleasant sensations that Jessica was causing me, and not getting a boner. I was actually relieved when it was over and she got off of me as my dick was really starting to hurt. It seemed just my luck that even my pleasure cards would bring me pain.
After Jessica had gotten off me I stood up myself. That’s when I felt the unmistakable sensation of liquid running down my butt and the back of my thighs. Jessica’s pussy had leaked all over me! I suppose I wasn’t the only one who had enjoyed the massage.
Jillian was already at the computer clicking on her action card when I walked over.
“Pleasure again,” she said as she rolled the dice. She got a three, and the words appeared.
“Make out with the player of your choice for 30 seconds. No groping is allowed.”
She looked at me hungrily for a second, and then turned to my sister. “Get over here Jennifer!” she demanded.
“What!?” Jennifer startled. “You want to make out with me?”
“Yeah, baby,” Jillian said huskily.
Jennifer’s mouth opened and closed like a fish, but no sound came out. She was totally flabbergasted.
All of a sudden, Jillian burst out laughing. “Oh, I can’t believe you fell for that,” she screamed as she clutched her sides. Tears were streaming down her face she was laughing so hard. “You should have seen the look on your face; it was priceless!”
“Yeah, yeah, very funny,” Jennifer responded, no real anger in her voice. She was too relieved that she wouldn’t have to kiss Jillian to be too angry.
“So who do you really want to kiss?” Jessica asked.
“Isn’t it obvious?” Jillian said as she wiped her tears away. “The man with the magic tongue,” she said indicating me.
I blushed at this reference to what had happened earlier. I guess she was hoping that I could use my tongue to bring as much pleasure to her mouth as I was able to bring to her pussy. I hoped so too. I hadn’t had all that much experience kissing, but by all accounts I did a decent job. Granted, I was kissing girls my own age, not someone older like Jillian who was bound to have more experience than me.
“Alright, Justin, show her what you got,” Jessica said as Jillian strode over to me.
As Jillian wrapped her arms around my waist, I put my hands around her upper back, which to my consternation was still covered by her shirt. I would have to fix that at some point. As we drew close for the kiss, I felt my dick press up against her stomach. I quickly bent my knees a little, and suddenly my dick was nestled between her naked thighs, right up against her pussy. I was instantly hard, and Jillian parted her thighs and then closed them again around my dick so that it was trapped between them. I was so close to cumming and we hadn’t even started kissing yet!
Finally she placed her lips against mine and we started kissing. It was only closed mouth so far, but it was still absolutely amazing. But my lips weren’t the only thing feeling incredible sensations. While we were kissing I was thrusting my hips backwards and forwards, causing my dick to slide in and out of the warm tight spaced that her closed thighs had formed.
After two or three seconds of this, Jillian darted her tongue past my lips and into my mouth. The instant that happened I came. Like a fire hose. The pleasure was so intense that I couldn’t remain standing, and I fell to the floor as my dick continued to pump.
“Oh my gosh,” Jillian exclaimed, hand over her grinning mouth as I continued to lie there, spasming in pleasure.
“Hey, the thirty seconds aren’t up yet,” Jessica said, making no effort to cover her own grin.
“But-” Jillian began as she looked at me. Then, shrugging her shoulders, she got on her knees and crawled on top of me.
I was still experiencing aftershocks of the most intense orgasm of my life. I had been knocked insensate from the pleasure and was completely unaware of anything until I felt someone kissing my lips. I opened my eyes and saw Jillian once again trying to find every spot in my mouth with her tongue. I could feel the weight of her body on mine, her large breasts pushing pleasantly into my own chest, her warm legs resting on my own.
My hands instinctively wrapped around her as I snuck my own tongue into her mouth. I immediately noticed the taste of toffee. Why did girls mouths always taste like candy? As our tongues started dueling, I slid my hands down her back. I knew I wasn’t allowed to grope, but the card said nothing about me just resting my hands on her ass.
If I was to express how I felt laying there, I would have to say perfect contentment. Which is why I found it so difficult to let her up when Jessica called time.
With a groan of disappointment, Jillian released her lips from mine and got off of me.
I took a moment to stare at her bare pussy before I got up myself. It was coated in cum. So was the bottom of her shirt. So was my stomach for that matter. I must have cum all over myself, and when she lay down on top of me, she must have gotten it on herself as well.
“Hey Jillian, you look a bit sticky,” Jessica said as she pointed to Jillian’s nether regions.
“What?” Jillian said as she looked down. “Oh, gross,” she said as she spotted my goo on her. “It’s on my shirt too.”
“Let me get some tissues so that you can clean off a bit,” Jessica said as she headed for a box of tissues on the bookshelf.
“No that’s okay,” Jillian said as she reached for the hem of her shirt. “This is going to have to go in the wash now anyway.” Then she proceeded to lift her shirt over her head. I almost came again as she revealed a flat stomach and a pale green bra that was forming the most amazing cleavage. She then took the shirt and proceeded to wipe her groin with it. A moment later, satisfied that she had removed all of my cum from her nether regions, she threw the shirt into the corner of the room and grinned at me. “I think that’s the first time that anyone’s ever cum from one of my kisses before.”
I blushed terribly at that. “It wasn’t the kiss that did it,” I said rather embarrassedly. “It was the… you know.”
“Why, I’m not sure I know what you mean,” Jillian replied coyly as her grin got even larger.
I didn’t know how to respond to that, so I just stood there blushing until Jessica announced that it was Jennifer’s turn.
Jennifer wasted no time clicking on her action card. This time however, she was greeted with bad news. “Pain,” she said somewhat nervously.
“Hey, look on the bright side,” Jillian said. “At least you can’t get kicked in the nuts.”
“Yeah,” Jessica agreed. “It can’t be nearly as bad as that.”
“I guess we’ll find out,” Jennifer said as she rolled the dice.
The dice came up 4 and the words appeared. “Have one of the other players give you five slaps on the ass with a flat bottomed shoe. This action requires you to remove the rest of your clothes which will remain off for the rest of the game.”
“How boring and traditional,” Jessica yawned.
I didn’t think so. It meant that my sister would very shortly be completely naked. One man’s trash is another man’s treasure; one man’s pain is another man’s pleasure.
“Why did it say ‘the rest of my clothes?’” Jennifer asked. “How does it know I’m not wearing all of them?”
“It’s a computer program,” I piped up. “It must be keeping track.”
“I guess that makes sense,” Jennifer said as she stood from the chair.
She placed her hands on the waistband of her skirt and hesitated. “Justin, look away,” she said.
“What? Why? I’m gonna be seeing you naked anyway. What’s the big deal?”
“Just because you’re going to be seeing me naked, doesn’t mean you need to see me undress. A girl’s got to have a little privacy.”
“Whatever,” I replied nonchalantly as I turned around. I may have sounded casual about it, but I was actually quite upset. Not that it mattered too much I suppose. Like I had said, I would be seeing her completely naked in a second.
“Okay, you can look again,” Jennifer said after a moment.
I turned around, and almost fainted. My sister was gorgeous! Sure, I had seen her in bikinis plenty of times, and she had been topless for the past 20 minutes. But this was something else. She had a completely smooth shaven pussy with prominent lips that just begged to be sucked. Not that I necessarily wanted to go that far with my own sister, but you couldn’t help but notice them. And she had one of those sexy tan lines where everything is bronzed except for the small whitish area that the bikinis bottoms covered.
It was only at this moment that I realized that neither my sister nor Jessica had tan lines on their breasts. In fact, Jessica didn’t have them anywhere. Of course Jillian burned so easily that she never sunbathed, so she was pale even though it was summer time, but I wondered just how Jessica and my sister got such complete tans. Definitely something to look into.
“Okay,” Jennifer said, “we need a shoe.” A moment later she found her own discarded shoe and handed it to Jillian. “Five hits,” she said.
My hand started heading towards my stiffy, but at the last second I realized that might not be a good idea. Instead I grasped my hands behind my back and waited for the action to start.
“Do you need me to bend over?” Jennifer asked.
“No this should be fine,” Jillian replied as she walked behind her friend. “You ready?”
“Yeah, go ahead.”
Jillian swung the shoe back and slammed it into my sister’s round, plump ass.
“Ungh,” Jennifer groaned as the shoe made impact.
“One,” Jessica said, apparently taking upon herself the responsibility of counting.
Swing. Ungh. Two.
Swing. Oww! Three.
I was mesmerized. Every time Jillian swung the shoe into my sister’s supple ass it jiggled deliciously. Like Jello. The type you wanted to stick your face into.
Swing. OWW! Four.
My sister’s ass was beginning to turn red. Nice.
Swing. AHHH!! Five.
And that was it. Jillian dropped the shoe back on the floor. “Are you okay?” she asked my sister gently.
My sister turned around as she started massaging her ass. “Well, it’s the first time I’ve gotten a spanking in almost ten years, but I think I’ll live. I just won’t be sitting down for the next few minutes.”
Jessica went next. Like Jillian, she got her second pleasure card. The dice came up 4.
“Have two people do anything you want for your enjoyment other than oral sex or intercourse for 30 seconds.”
“Hmm,” Jessica mused. “Very interesting.” She paused in thought for a moment. “You know, I have to admit, that when Jillian asked to kiss Jennifer it got me excited. I want to see that.”
“Ha ha Jessica,” Jennifer began. “That joke’s already been played.”
“Who’s joking?” Jessica remarked innocently. “I’m not joking. I really want to see you and Jillian make out. Or I could just ask you to make out with your brother.”
Jennifer looked at me. It looked as though she might find that preferable. Jessica noticed this too and put a stop to it before it could lead anywhere.
“No, on second thought, you have to make out with Jillian.”
“But why?” Jennifer moaned as she started walking towards Jillian, a look of dejection on her face.
“Because sometimes I just like to be mean, that’s why.”
“Yeah, well you’re being a real bitch alright,” Jennifer agreed.
It suddenly occurred to me that through this entire altercation, Jillian hadn’t said anything. She looked as if she was simply waiting to kiss Jennifer. Not in an overly eager way or anything, but she certainly didn’t look sick about it like Jennifer did. This was something else I was going to have to look into.
Jennifer approached Jillian, and for a moment she couldn’t figure out where to put her hands. This was a girl that she had hugged a million times before, and now she was treating her like a hot stove. Finally her hands came to rest awkwardly on Jillian’s shoulders.
Jillian on the other hand, easily slipped her own hands around Jennifer’s waist.
Jessica stepped right next to them. “I wanna see tongue too, okay?” Jennifer didn’t say anything to this, but she did flash Jessica a nasty look.
Jessica picked up my stopwatch. “Ready, begin.”
Jillian made the first move, bringing her face right up to Jennifer’s and pursing her lips out so that they just touched her friend’s. After a moment of contact that met with no resistance, Jillian mashed her lips into Jennifer’s a little harder and started rubbing them around.
Like a switch had been flicked, Jennifer finally started moving. She started to rub back and this seemed to really excite Jillian, who suddenly grabbed Jennifer’s lower lip between her teeth and started to nibble on it. Jennifer moaned, which caused her to blush, as she was still in denial that she could actually be enjoying herself as she kissed another girl.
Taking the moan as a affirmative, Jillian moved in for the kill. She thrust her tongue straight into Jennifer’s mouth, where Jennifer proceeded to suck on it quite vigorously. This caused Jillian to start moaning and shivering, and her hands, which had been resting on Jennifer’s lower back, slid down to Jennifer’s naked ass where they gently massaged her luscious globes.
Although they had only been going at it for ten seconds, they had already reached such a frenzied state that had an earthquake began at that moment, they would have dismissed it as their racing hearts.
Jennifer’s hands finally relaxed and likewise slid down to Jillian’s butt. And while she wasn’t exactly massaging it, it didn’t look like she was planning on letting go any time soon.
Meanwhile, I couldn’t contain myself anymore. Watching my hot, nude sister make out with her equally gorgeous friend was too much for me to take. I was stroking my dick for all I was worth. The two girls were oblivious of course, but Jessica noticed and gave me a smirk. I didn’t care who saw though. This was one of the hottest things I had ever seen in my life. In fact I was enjoying it so much, my eyes started to close involuntarily from the pleasure, even though this kind of impeded my view.
I was half gone with lust and pleasure, stroking my meat with utter abandon, when a voice startled me out of my self service.
“Did you enjoy the show little brother?”
I looked up to see that Jennifer and Jillian had finished their make out session, and now all three of the girls were watching me stroke my dick with large grins on their faces.
For some reason, even though I was currently experiencing the most humiliating moment of my life, my dick seemed to enjoy the attention, because the next thing I knew, I was spurting again.
My first blast shot out like a cannon, spraying in a straight line from the bottom of my sister’s breasts right down to her belly button.
She squealed and jumped out of the way, exposing Jessica as a target.
Like a homing missile, my second shot, which was even more intense than the first, sprayed Jessica directly across the face, getting both her cheeks and her nose with a copious amount of my creamy white fluid.
My next four spurts could have ended up on the moon for all I knew because I was so lost in pleasure that everything else ceased to exist for me.
I must have been laying there for close to a minute before I was able to open my eyes again. The first thing I saw was Jennifer handing Jillian’s already soiled shirt to Jessica, who proceeded to wipe her cum-soaked face with it.
“I guess that answered my question,” Jennifer said to me with a giggle as she scooped some of my cum out of her belly button.
Jessica finished wiping her face and threw the now completely cum covered shirt back on the floor.
“If you cum on me again, I’m gonna rip your dick off.” Even though she said it like she meant it, there was a sparkle in her eyes that I didn’t quite know how to interpret. She looked at the other two girls. “I’m going go wash the rest of Justin’s cum off my face. We’ll start round 3 when I get back.”
I just lay there and stared at the three girls, completely unmoving. This had turned into the best day of my life, and I definitely wanted more, but I don’t think I had enough energy left in me to scratch my nose, let alone play 8 more rounds of this game. This thought was making its way through my head as I drifted to sleep.

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