Jack and Jill

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"So has anyone ever done it to you?"

"Lick me?"

"yeah."

"Nope. Always wondered what it was like though."

"Well, maybe it's worth a try." I said as I sunk down lower on my knees, bringing my face closer to her pussy. I wrapped one arm around each of her thighs, using my fingers to gently play with her fat outer lips and the frilly looking inner lips that were protruding slightly. I pulled her lips apart and looked at the deep pink cleft it made. Tentatively I reached my tongue out and stroked it along her pussy, tasting her juices. Her pussy was tangy, almost tart.

"Mmmmmm that feels awful nice." She whispered as I stroked my tongue a bit deeper between her lips. I continued to stroke her, teasing deeper and exploring more and more of her. I soon found I could press the tip of my tongue into the entrance to her tunnel, which brought a soft groan from her. I also spent time exploring her clit, learning that if I pulled the point where her lips met, that I could expose her clit. It seemed that each time I flicked her clit with my tongue she arched her back, trying to push her pussy up to my face.

I began to concentrate on her clit at the end of each stroke and soon had her withering and squirming on the bed, her fists full of her blanket her whole body shuddering. Her juices flowed more easily and were much less tangy now, almost sweet.

"Stop, stop." She finally gasped, reaching down and pushing my face away with one hand.

"Wasn't I doing it right?" I asked, feeling almost defeated that I had done it wrong.

"Oh Jack, Jack. You did it soooooo right. God I was coming and coming and coming so hard that I just couldn't stand any more." She said as she sat up and pulled my arms.

She continued to pull me until she was lying back again, my body being pulled along hers. I felt her hand slip between us and grasp my cock. Her hand began to slowly stroke my rigid cock, my head brushing against her pussy and her hot wet lips. "Want me to suck you off?" She whispered quietly.

Before I could answer, there was a knock on the door and our mom's voice calling. "Jill, you up?"

With a horrified look on both our faces, we quickly separated and I darted back into the bathroom, silently closing the door before she called out in answer.

Fortunately sis and I were able to keep everything looking normal most of the day, although when we were alone I did take the opportunity to reach my hands around her and cup her tits through her shirt and bra, giving them a playful little squeeze. The first time I half expected her to turn around and slap me, but was pleasantly surprised when she lifted her hands to mine and gave them and her own breasts a squeeze at the same time.

We were both worried about mom and dad finding out what we had done, and the way we were playing, so whenever there was the slightest chance of them seeing us we maintained our normal, or at least the way we perceived normal, behavior.

During the afternoon dad had me help him blow up the two air mattresses in sis's room, after which mom tossed in some blankets and pillows. Being the nerd that I am, and being the horny guy that I am, I just had to slip into her room and plant a little wireless camera. I hid it on her dresser between a couple stuffed animals, pointing it so I could see the bed and both air mattresses, hoping to get a good look at all of their titties while they were changing. I was pretty sure that if sis found it that she wouldn't say anything, but if one of the other girls found it then it would be curtains for me.

After dinner the girls started to show up, Mary was there of course, wearing a modest black skirt and button down shirt, her tits making a few buttons strain slightly.

Stephanie Morris showed up a bit later wearing a red mini-dress that was a stark contrast with her creamy white, somewhat freckled skin and helped make her auburn hair seem even darker red. The dress hugged her curves, including her chest, which looked like a pair of softballs stuffed inside the top of the dress, the two creamy white orbs pressing together visibly in the deep V of the front of the dress.

Tina Stobin and Aimee Snodgrass shared a ride and arrived together, Aimee wearing a pair of seriously tight jeans and an equally tight tank top that accentuated her orange sized breasts, two little bumps where I imagined her nipples were, poking out slightly farther. I wasn't at all sure she was even wearing a bra.

Tina was the exception to the group so far, with very small breasts that barely pushed out the front of the little blue dress she was wearing.

The last to arrive was Suzie Kowawitz. She had on a cute little red skirt and a white button down blouse that slightly showed the shape and outline of the bra she had on under it, capturing what looked like a pair of apple sized tits. She also had on very high heels, what my friends called "fuck me" heels.

With the girls all there, I was relegated to the living room to watch TV while the girls all partied down in the downstairs family room. All I could do was watch TV or retire to my own room. Given what I know sis was planning, I finally gave up watching, retiring to my room to read and await a later hour.

I didn't have to wait all night, well before mom and dad went to bed the girls retired to sis's room. As soon as I heard their giggle and chatter on the other side of the bathroom door I turned on the computer and connected to the camera in sis's room.

The image I saw before me was...well, staggeringly incredible. All of the girls were in various states of undress, changing from their party clothes into their pajamas. As I watched them getting naked I couldn't help but undo my pants and sit and stroke my cock as I stared. As sexy as the girls looked in their PJ's, none of them wearing bras so their tits wiggled and bounced in the thin material of their nightwear, it was disappointing to no longer be able to see their naked bodies.

The girls sat in a circle on the two air mattresses, and began playing some kind of card game. At first I thought it was going to be boring, but it seemed that the loser of each hand had to tell some secret. At first they were pretty bland, but before long they seemed to move to juicier secrets. I learned that Aimee had made out with another girl once when she was drunk at a party, that Stephany lost her virginity almost a year before behind the bleachers at a football game, Trina peaked into the boys locker room one time and probably the juiciest secret, that Suzie used a dildo to get off almost every day.

Overall the game was interesting to listen to, but what I was waiting for was for sis to try and get Mary naked. It was only a few minutes after mom checked in with the girls on the way to bed that the "real" fun started as my sister called it. I watched and listened while she described the game to the girls.

"So, it's called I dare you. You make a dare, whatever you want, and then roll the dice. Whoever's number comes up has to do the dare. If they can't for some reason, then the dare falls back on the person that made it. Like if you dare to take off your shoes, and the person who comes up isn't wearing any, then you have to take yours off. Since there's only six of us we'll just use one die. I'll be one, Mary Two, Three, four, five and six." She said, continuing around the circle of girls sitting with her.

"Rules are simple. Any dare is fair game except something that would cause bodily harm or get someone arrested. I'll start first just so everyone gets the idea." My sister continued. "I dare you to French kiss the girl on your right..." She said before tossing the little red die on the bed between them all. It landed on four. "...Trina! You have to French kiss Stephanie."

"Oooooooooo." The other girls called as they waited for Trina to lean over and kiss Stephanie. I could only see the back of Stephanie's head, but Trina leaned over and the two embraced for several seconds before pulling away from each other, everyone breaking down in giggles.

"Ok Trina. Now it's your turn to dare and roll." My sister said when the giggling died down.

"Okay. I dare you to...hmmmm...I dare you to take your shirt off and make your nipples hard!" she said as she reached for the dice.

"Just remember Trina, the dare could come back to you if you roll your own number. Oh yeah, one more thing. Once a piece of clothing is taken off, it has to stay off until the end of the game." Jill explained before Trina rolled, the die coming to rest on five.

"Ohhhhhh Aimee!" Stephanie cried, pointing to her and giggling. "Gotta lose the top sweetie!"

"Yeah, stand up and do it so we can all see it!" Jill called.

Aimee rolled her eyes and stood up. She skimmed the thin terry nightshirt she had on up and over her head, tossing it onto the bed, leaving her standing there in just a tiny little white thong. Her tits were easily the size of a couple good size oranges with large pink areola and nipples that looked to be about as large around as my pinkie finger. She stood there, closed her eyes and began to massage and tease her tits, squeezing them between her palms and fingers. After a minute or so of this treatment she began to run her fingers lightly over her nipples teasing them with extremely light brushes of her finger tips until they stood hard and prominent on each firm round breast.

She probably would have continued to stand and tease her nipples if Trina hadn't slid a hand discreetly up her thigh and started to stroke her pussy through her thin panty.

"Whew." Aimee said, wiping her dishwater blond hair out of her face and sitting back down. "Okay. I dare you to stand up, take off all your clothes and play with your pussy!" She rolled the die. "Come on four!" The die stopped on two.

"Oh shit. Mary!" Suzie said, covering her mouth.

"Well, never let it be said I wasn't a good sport. Here goes nothing!" Mary said as she climbed to her feet. She had on a pair of light flannel PJ bottoms and long sleeved tops, which she quickly pulled off and tossed aside. She bent over and skimmed her little white panties off her butt, lifting one leg after the other until she could toss them aside, leaving her completely naked. Her tits were indeed large, almost the size of a couple melon halves. Her areola were large, covering a good part of the front of each breast with a large round nipple perfectly centered in the middle of each areola.

I hadn't even paid any attention to her pussy until she slid her hand down between her legs, which she spread apart. Her finger slid down through her sparse blond curls and disappeared between her legs. Unfortunately her hand blocked my view of most of what she was doing between her legs, but her free hand had traveled up to her chest and was pinching and twisting one of her nipples like a little knob.

"Ohhhhhh shit." Mary mumbled after more than a minute, pulling her finger from her pussy, glistening with her moisture. "So my dare now? I dare you to make the girl on your right naked and to lick her pussy for a full minute!"

"Shit, seriously?" Aimee asked. "You Mary?"

"It's always the quiet ones." Tina said shaking her head.

Mary rolled the die and then stared at the two that was showing.

"Whoa. Didn't see that coming!" Suzie said quietly.

"Well, that sucks." Mary said quietly.

"You got that." Jill agreed, realizing she was the one to Mary's right.

"Well, let's get on with it." Mary said, standing up again. She waited for Jill to stand up and then pulled off the nightgown Jill was wearing and then knelt down in front of her. She slipped the tiny bikini panties down her legs and then tossed them aside. "Somebody keep time." Mary said as she leaned her face between Jill's legs.

I couldn't see what exactly she was doing, but I guessed from the way her head was moving that she was aggressively licking my sister's clit. It was the same look I had seen on Jill's face when I was licking her pussy, her eyes closed, her mouth hanging part way open.

"Okay, time!" One of the girls called.

Mary pulled away, wiping her face with the back of her hand while Jill sunk down to sit again, her chest heaving with arousal.

"So I go again. Let's see. I know that Trina brought a toy or two, I dare you to strip and play with yourself with that toy until you come."

"Damn Mary! You really wanna dare that?" Aimee asked in a little squeak.

"Yep, why not?"

"Paybacks is hell sweetie!" Suzie chimed in.

"We'll see." Mary said, rolling the die, the small cube landing with the six pointing toward the ceiling.

"Aww crap!" Suzie said quietly. "You're not serious, are you?"

"That's the game, unless of course you wanna drop out." Mary said with a grin.

"No," Suzie said with a sigh. "But I guarantee the next girl is gonna regret it, and I hope it's you Mary!" Suzie stood up and pulled off the nightgown she had on and then slipped the little pink panties down her legs, stepping out of them. She stepped back to the edge of the bed and sat down while Trina went over to her little suitcase and came back with what looked like a fat pink cock. Suzie lay back on the bed, her apple sized tits sticking in the air as she hooked her feet on the edge of the bed and spread her legs wide. Her little brown triangle of hair pointed straight at her fat outer pussy lips, her inner lips protruding slightly as she spread her legs farther.

Taking the pink dildo with both hands she rubbed it up and down her slit a few times, lubricating the tip and then working it deeper between her lips. "Oh shit." She moaned as she tried to force the dildo deeper into herself, working it in little strokes while she twisted it back and forth. While I watched, her pussy pointing almost straight at the camera, she worked the plastic cock fully into her pussy and then began stroking it in and out in long even strokes.

"Oh god." She mumbled as she lay with one hand working first one nipple and then the other as she plunged the artificial cock in and out faster and faster. "Oh that's it Frank. Fuck me! Fuck my hot little pussy!" She moaned loudly as she started humping her hips up in time with her strokes in with the dildo. "Oh....Oh god... Ohhhhhhhhh shit!" She squeaked as her whole body dissolved into shudders and trembles. She lay there for long seconds, her chest heaving, her body slowly pushing the dildo out until it fell from her sopping wet pussy.

"Okay. I dare you to strip naked, go into Jill's brother's room and come back with his underwear....not just any pair, whatever pair he's wearing right now. Someone roll the dice for me." Suzie panted from where she was lying on the bed, her legs still spread wide.

"God, Suzie, you're not really gonna..." One of the girls started to complain.

"Yep. No whining. You got to watch me fuck myself, so now someone gets to go see a real cock, and part of me hopes it's me."

"Okay, here goes." Jill said, rolling the die. The cube bounced several times before Jill announced "three."

"Three?" I squeaked. Shit that meant that in a few moments that sexy little redhead was going to come in here and try and get me to take off my underwear! Oh shit! I quickly hit the computer sleep button and ran to the bed, pulling my pants pack into place over my hard on. I grabbed a magazine and pretended to read it while I waited for what I hoped, and also sort of feared was going to happen.

The knock on the bathroom door was ever so soft. I almost didn't hear it. The second knock was a bit louder, to which I answered simply "yeah?"

The door opened slowly, a redhead peeking around the door to see where I was. Nervously she stepped around the door, completely naked. Her trimmed triangle of auburn hair looked so much better now than it did when I got a glimpse of it as they were changing, but what my eyes really locked onto were the full round tits, each topped with a half dollar sized areola with a large flat nipple centered in it. The whole nipple and areola seemed to be pushed out, almost like a little mountain on top of another mountain.

"Um, Jack?" She practically whispered.

"Uh. Yeah?"

"So. Um. We're playing this dare game, and I got dared to come get your underwear." She said meekly.

"Naked?" I practically squeaked, staring at her nude body, her hands clasped in front of her crotch somewhat shyly.

"So....I'm just supposed to give you a pair?" I asked as she stood half way across the room.

"Not just any pair, the pair you're wearing."

"HUH?." I said not sure what to do. "So. I'm supposed to just get naked in front of you?"

"Well, I'm already naked." She said with an almost exasperated look. "So are you going to let me have your underwear or are you just going to sit there and stare at me?"

"Um. Yeah." I said getting up off the side of the bed. I started undoing my pants and then stopped. "You want em, I guess you're supposed to come take em off of me?"

"I suppose so." She said, nervously stepping forward again.

I stood still as she stepped forward, kneeling down in front of me and taking over undoing my pants. She worked my pants down my legs and then off my feet before her hands returned to tug down my boxers, revealing what was making the huge bulge. My cock nearly slapped her in the face when it sprung out of the waist band of my boxers.

"Damn." She mumbled, as she pushed my boxers as far as my knees her hands seeming to be frozen there as she stared at my hard on.

I was going to say something, but wasn't sure what the hell to say, except "Ohhhhhh damn." As she reached up and wrapped a hand around my cock.

"God it's big." She whispered.

"Yeah, I know. I get kidded about it all the time." I said with a wry face.

"Seriously? They make fun of you for this?"

"Yeah. Too big and seems like it's always hard." I admitted quietly.

"A girls dream! A big cock that's always hard and ready? I wish I was so lucky." She said quietly, looking up at me and leaning her face toward my cock. Her mouth engulfed my head and I felt her tongue swirl around my head as the heat from her mouth seemed to radiate throughout my entire body.

"So you about done in here?" I heard one of the girls call from the bathroom.

"Oh damn." Stephanie said, pulling her mouth off my cock and quickly pulling my boxers the rest of the way down. "Almost!" she called back to Suzie who was peaking around the bathroom door.

I lifted my feet and watched Stephanie quickly scamper across the room and into the bathroom, closing the door quickly behind her.

I plopped back on my bed and lay down, mostly in shock from what had just happened. I barely had time to catch my breath when there was a quiet knock on the door and it opened without waiting. One at a time all six girls walked into my room, all of them completely nude. There was more tit and pussy on display than I'd ever seen at once, except in a magazine maybe.

Aimee led the procession, walking toward me, her gate confident, but the look on her face anything but. "So, you know we're playing this game. I just got dared to suck your cock. Are you game?" She asked, her voice trailing off to near silence as she got close enough to really see my cock. "Holy shit. You weren't kidding Steph!" She said as she continued to step toward my bed, a lot slower though now.

"Yeah, for real, isn't it?" Stephanie said from behind Aimee as Aimee stepped right to the side of my bed. She reached one hand out toward my cock, almost as if she were afraid it was going to bite, and then slowly wrapped her fingers around it, my girth large enough her fingers and thumb were a long way from touching when she closed her hand.

"God it's got to be twice as big as Jimmie's cock." Aimee said to no one in particular as she slowly crawled onto the bed, straddling my legs with hers, one arm holding herself up so her face hovered only a few inches from my cockhead where she held it vertical with her other hand. I looked her body up and down, from her round tits, the size of a good size orange, down to her pussy, which I was surprised to see was shaved completely smooth.