Jack and Jill

"Oh god." I groaned, closing my eyes for a moment as her hot mouth engulfed my head. I felt her hand and her lips begin to slide up and down my cock, her mouth sliding down several inches until I felt my head press against her throat before sliding back up again, her tongue rubbing back and forth across the bottom side of my cock as she withdrew until only my head was contained in her mouth.

I opened my eyes and saw all the girls, all naked, standing next to the bed watching as Aimee drove me crazy with the hot wet sensations of her mouth. I was just beginning to wonder how I was going to let her know when I was going to come, when one of the girls called time and Aimee pulled her mouth and hand from my cock.

"Okay girls. Next girl has to let Jack fuck her pussy from behind until she comes." Aimee said as she sat upright on her knees, still straddling my body. "God I hope it's me again!"

"Two!" one of the girls said from behind the others. "Mary, that's you!"

"I can't!" Mary objected loudly, and then more quietly, "I can't. I'm not on the pill or anything."

"Okay, Mary can't do the dare. That means it comes back to you Aimee. Looks like you get your wish!"

"Hot damn. I'm so fucking horny and god this cock is just...shit, fantastic!" Aimee said in an uncharacteristically husky voice.

"Jack. You don't have to do this if you don't want to." Jill said, stepping around from behind the girls.

"No, it's fine." I answered, as if I was going to actually turn down my first real fuck?

"Aimee, you have to ride until you come, even if he comes first. You sure you want to do this?" Jill asked Aimee quietly.

"Uh huh. I'm ready! You ready stud?" She asked as she reached down for my cock again and wrapped her hand around it, holding it straight upward. She walked her knees up from down by mine until they were at my waist and then she bent over, pushing her ass back toward my cock. I felt her hot pussy lips envelop my head and then pressure built against my head. She settled more and more weight on my cock, pressing it down until suddenly I felt it surge upward, pushing into her tight pussy, her tunnel tightly gripping me as she began to slowly rock herself on all fours, driving my cock in and out of her pussy in short little jabs that slowly worked me deeper into her.

"Oh my god is he big." Aimee moaned softly as she started stroking herself on and off my cock in long even strokes, cute ass bouncing lightly on my thighs at the end of each stroke. "Ohhhh god yes." She moaned.

I really wasn't all that sure what I should be doing, but her swinging tits were an inviting target and I just couldn't resist. I reached up and cupped both round tits, gently squeezing them as I tried to contain the swinging orbs.

"That's it. You can squeeze them more if you want." She breathed as she continued to stroke herself on and off my cock.

I could feel the tingle in my balls that I had long since learned meant I was close to squirting. I tried to croak out that I was about to come, but I wasn't sure that Aimee heard me. My body jerked hard, driving my cock up into her as she came down on me, my cock surging a huge gush of hot cum into her pussy.

"Shit! He's coming!" she squealed as my body jerked time after time, pumping more and more into her pussy. She leaned her face down to mine, keeping her hips pumping up and down, driving her pussy on and off my shaft. She let her nose touch mine and slid her face down until her cheek touched mine. "Can you feel my pussy fucking your hot fat cock? I want you to stay hard. I want you to feel my pussy come around your fat cock. Just concentrate on how good my pussy feels around your cock and how good my tits feel in your hands. Do you want me to come around your cock? Do you want to feel my girl come soaking your cock and leaking around you? You'll only be the second guy I've ever climaxed on. Do you like that idea? But yours is so big and is hitting all the best places inside me. Mmmmmm god your cock feels so good. I can feel it getting bigger again. Getting fatter inside me. I can feel it getting me closer to coming. Kiss me. Kiss my lips and suck on my tongue and I'll come on you!" She whispered, her breath tickling my ear before she pulled her face from next to mine and pressed her hot lips against mine. I felt her push her tongue into my mouth and as requested, sucked it lightly.

"mmmmmmmmm" she moaned into my mouth as her body began to tremble. She pulled her mouth from mine and leaned her forehead against mine, pressing herself down on my cock and grinding her pussy against me. "I'm coming." She panted. "Oh god I'm coming...Ohhhhhh shit. Here it comes!" She squeaked as her whole body suddenly shuddered for several seconds. I could feel her pussy clenching around my again hard cock as she sat, trembling, on me.

She leaned her face down next to mine again and whispered. "Would you like to lick one of those sexy pussies? Have one sit on your face and suck your cock while you lick her pussy?"

"Uh huh." I grunted back.

"It's the least I can arrange after such a fantastic fuck." She whispered before pushing herself up. "Okay girls, Next dare. I dare you to sit on his face and let him lick your pussy while you suck our juices off his cock! Someone roll the dice!"

"Two! Mary!" Jill called from behind the girls.

"Ohhhhh shit no!" Mary squeaked. "I can't do that!"

"Can't or don't want to?" Suzie asked from behind her.

"Hell no I don't want to!" Mary said, her voice easily a couple octaves above her normal tone.

"SHHHHHHH!" Jill hissed. "Not so loud! You'll wake my parents!"

"I don't care. I'm not going to do that!" Mary answered.

"Why not? We all did our dares when it was our turn. You gonna chicken out?" Trina chided. "Come on. We all know you're a virgin, but damn girl!"

"Oh fuck. Alright!" Mary said, her face a mask of displeasure.

Aimee climbed off my cock, which she had been gently rocking on to keep me hard. Once she was off, Mary moved hesitantly to the side of the bed and started to climb on. She stepped across me so she was standing on my bed, straddling my head. She bent over and put her hands on either side of my hips, her huge melon sized tits hanging down spectacularly below her. I couldn't help myself. I reached up and grasped each tit, her huge hard nipples pressing into my palms as she lowered herself to her knees, one on either side of my head.

Her pussy was framed by a sparse bush of blond curls that extended from her rounded mound down to her fat outer pussy lips. Her thinner inner pussy lips protruded significantly out from between her outer lips, little drips of moisture clinging to the edges, only a few inches from my face.

She spread her knees apart slowly, sliding them across the bed sheets and lowering her pussy down to my lips.

I reached my tongue out and teased it along her lips, tasting her tangy wetness and gently spreading just the very edges of her lips. On my second slow sweep of my tongue down the length of her lips, I found her clit, already exposed, and flicked my tongue across it.

"Oh fuck!" She squeaked as my tongue flicked across her clit a second time. I concentrated on her clit like Jill had shown me, causing her to moan loudly.

"Don't forget to suck his cock!" One of the girls coaxed with a giggle.

"Oh fuck. You've got to be kidding!" She answered, her hips rocking gently, trying to grind her clit into my face. "God it's all I can do to not scream!"

"Then muffle it with his cock!" The girl answered.

I continued stroking my tongue between her lips, playing with her clit at the end of each stroke, pausing only for a moment when I felt her mouth engulf my cock.

"Ohhhhh god." I groaned into her pussy, my hand involuntarily squeezing both her tits as she drove her mouth down my shaft, taking in even more than Aimee had. The two of us spent the next...hell who knows how long, working on each other until she finally pulled her mouth off my cock, a long low moan, almost like a growl, escaping her lips as her whole body shuddered and twitched over me. Her juices leaked from her pussy, running down over my face and leaking down my neck.

Mary shakily pushed herself off of me and rolled over onto the bed next to me, her feet sticking up the headboard and wall by my head and her head by my knees. "If my daddy would let me date boys you'd be at the top of my list. God damn that was good."

"Don't quit on us yet. You have the next dare!" One of the girls said.

"I don't care. Someone else can take my turn." Mary mumbled, her hands sliding up and down her body and teasing her nipples lightly in the aftermath of her climax.

"Okay, last dare. Since Jack has been such a good sport, whoever gets the next roll lets Jack fuck her doggy style until he comes!" Jill said from behind them. "Who wants to roll?"

"I will." Suzie said, stepping out of the circle. I couldn't see what was happening, but I expected that she was rolling the die they used to play the game. "One. Oh shit. It's one!" Suzie said from where she was behind the rest of the girls. Everyone except Mary, still lying next to me, turned to stare at Suzie and Jill.

"You don't have to. I'll do it." Suzie said quietly.

"No." Jill said firmly. "I'll do it. Guess the game was my idea after all. It'd be kind of hard for me to make you all do the things we did and then back out."

"It's okay Jill. You know none of us can ever tell anyone about this anyway, so your secret is safe with us!" Mary called from where she was lying.

Jill walked over to my computer chair, and bent over the back of the chair, reaching down to hold onto the arms of the chair. She stepped her legs apart and stood there, waiting, slowly wiggling her ass from side to side.

Mary sat up and then rolled around so her face was by mine. "You know, if I could, it'd be me standing there right now, wiggling my ass, which by the way is an invitation. I like how you feel in every way you've touched me, but I really really would like to feel you inside me. If you promise not to come inside me I'd really like to sit on you for just a second before you go pump it into Jill."

"Seriously?"

"Just for a second." She whispered.

"Can I tell you a secret first?"

"Sure."

"I've kind of had a crush on you for a long time."

"Then we'll both really enjoy this." She whispered before softly kissing me on the lips. Almost as soon as she broke the kiss she rolled over on top of me, pushing herself back down my body until her pussy was rubbing on my hard cock. She lifted herself up on her knees and reached between her legs, lifting my cock and rubbing my head between her wet lips. "I haven't ever done this before, so I hope I do it right."

"I haven't ever done it before tonight either, so if you do it wrong neither of us will know. Oh damn." I answered as she sat down and engulfed my cock with her hot wet pussy. I could feel her tunnel caressing me as she slowly pushed herself down farther and farther, finally stopping when my head was nestled into the end of her tunnel.

"Oh god that feels soooooo good!" she moaned, sliding herself up and down my shaft very slowly. "I just want to keep doing this, but we both know what would happen."

"Yeah. For sure." I answered, sliding my hands up to cup her huge tits, lifting and squeezing them playfully as she continued to ride slowly up and down my cock.

"Okay. I gotta stop. But buster, you better get some god damn rubbers before I stay overnight next time."

"Uh huh." I grunted as she lifted clear of my cock.

"Now go fuck her. You know you want to." Mary whispered as she leaned close to my face and gave my cheek a soft kiss.

I rolled off my bed and Jill, who had turned around to watch Mary and me, bent back over my chair again. I stepped up behind her and rubbed my already pussy slickened cock up and down her wet lips. I pressed forward, slowly pushing into her a few inches. I started stoking in short little jabs, working deeper into her pussy with each stroke until my hips were pressing against her firm round ass.

"Oh god that feels good." She moaned quietly as I started stroking in and out of her pussy, driving fully into her and then pulling back until I almost popped out. I heard another moan and looked over to see Suzie, on her knees, her legs spread wide apart and two fingers plunging into her pussy while the other hand moved from tit to tit, squeezing and playing with her own nipples.

"Oh god. I'm gonna come." Jill moaned, bringing my focus back to her. Her legs and arms shuddered and I could feel her pussy spasm around my cock as her orgasm took hold of her. The feeling of her tunnel rippling and squeezing me, along with the sound of two girl's moans was more than I could take.

My body suddenly jerked, jamming my cock fully into Jill and driving both her and the chair into my computer table as my cock pumped the first squirt of hot cum into her. Time and again my body jerked, adding to the load filling my sisters pussy, until my body, spent, began to soften inside her.

"Shit is that my room?" Jill squeaked as she looked at the computer screen, the area where the girls started the game showing on the monitor.

The other girls gathered around and looked too. "It is!" One of the girls agreed. "Shit he was spying on us!"

"Jack! Were you watching us?" Jill asked, still bent over, my cock still plugging the hole filled with our combined cum.

"Just a little." I admitted sheepishly.

"Well!" Trina said in a huff, walking out of the room. I could see her on the computer screen walk to the dresser and dig around until she found my little camera. Her hand closed around it and she walked back to my room carrying it. "I was going to suggest that since some of us are still pretty horny that maybe we should just bring the toys over and have a little more fun, but maybe we ought to go do that in private now?"

"Yeah, I think so too." Suzie said. "Too bad, Jack. I was going to give you a special treat later."

The girls filed out, Jill pushing me back, releasing a small flood of cum that leaked down her legs. "Don't worry, I'll smooth it over." She said as she walked away. "You coming Mary?" She said as she stopped at the bathroom door.

"If you don't mind Jill, I'd like to stay here a little longer."

Jill smiled at her. "Don't have too much fun." She said before closing the door behind her.

"You're staying? You're not upset that I was...well...spying on you guys?"

"Don't let them fool you. Most of them love to show off. Besides, if we're going to be an item we might as well spend as much time together as we can, don't you think?"

"Are we going to be an item?"

"Well, my daddy still won't let me date, but nothing says we can't hang at school and oh gee, I bet he wouldn't mind at all if I came over here and had you help me with my calculus. I'm just having an awful time with it!" she said with a little smirk. "Now come back over here and let's see if we can find a few more things that feel good besides fucking."

I crawled into bed with her and the two of us spent the next hour or so playing and touching and kissing each other all over until we both admitted we were tired. We curled up together and went to sleep, our legs tangled together, her hand on my cock and one of my hands on one of her big tits as she lay her head on my chest. I was in heaven.

The morning was just starting to brighten the window when I woke up. In the night Mary and I had apparently rolled and changed positions, the two of us spooned together with me behind her. I had an arm around her, cupping one of her tits and I could feel my cock, rock hard, sticking between her legs, her fingers gently stroking my head.

"Are you awake?" She whispered.

"Uh huh."

"I want you to fuck me, but you have to promise to pullout before you come, okay?"

"Sure." I answered eagerly.

She lifted her leg up in the air, spreading her pussy lips as she pressed my head against them. I felt the heat of her pussy on my head as she rolled herself slightly, pulling herself along my cock until I felt my head press into the entrance to her tunnel. She rolled back, pressing her bare ass against my thighs, my cock sliding easily and deeply into her pussy. She lowered her leg and then reached a hand for mine, sliding it from her tit, down her body to her pussy. "Play with me while you fuck me. I want to come around you before you come, okay?"

"Sure." I whispered back, starting to stroke my hips slowly while I worked my fingers between her lips. "How's this?"

"Perfect." She whispered back, starting to rock her hips in time with mine. Back and forth we went, driving my long shaft in and out of her only a few inches, but the sensation was incredible, as was the feeling of her pussy on my fingers. She moaned softly and whispered to me. "God you feel good in me. I wish we could do this forever. I wouldn't mind waking up this way every morning."

"Me too." I agreed breathlessly as my orgasm built with each passing moment. "I don't know how long I can hold back."

"I'm almost there. Just another few moments'" she murmured back. "Can you feel my legs? When they tremble like this it means I'm about to.....Ohhhh shit yes!" she squeaked as her body jerked, her pussy clamping around me. Her motions faltered and her timing with my strokes was broken, but I still smiled, knowing that I had brought her off to a good climax. Her erratic motions on my cock also bought me a few more seconds, allowing me to enjoy her orgasm around my cock before I had to pull out of her. I pulled my hips back and then jammed them forward again, driving my cock between her thighs so that it stuck out in front of her. I continued to rock my hips, driving my shaft in and out of the juncture of her thighs, her wet pussy lubricating us as I fucked her body the last few strokes before my cock erupted, spraying shot after shot of cum out onto the bed in front of her.

"Ohhhhhh that was a strong one, wasn't it?" She whispered, reaching her hand down and gently playing with my cockhead while it leaked cum that ran down her thigh to the bed.

"Yeah it was."

"One of these days I want to feel that inside me." She whispered.

"Yeah, me too."

We lay quietly for a long time before she said anything else. "Jack."

"Yeah."

"Can I tell you a secret?"

"Sure."

"Will you promise not to freak out or anything, even if you think it's gross?"

"I promise."

"You know, my dad won't let me date boys, so you're actually the first boy that I've ever had sex with."

"Uh huh."

"But...well...I'm not exactly a virgin." She said, falling quiet for long seconds.

"I don't understand. How can you not be a virgin if I'm the first guy you've done it with?"

"My dad lets me spend the night at friends houses - girls houses." She said again going quiet.

"So?"

"Well, girls do things... Kind of like last night."

"Yeah so?"

She rolled herself over so she could face me, her eye searching my face for something in the dim light, but I didn't know what.

"Aimee has a lot of toys, and well, her mom has a lot more of them. One time we used this thing, it's like a dildo on a harness. Aimee put it on and she fucked me like a boy, then we switched and I put it on and fucked her that way."

"So?"

"Well....I liked it. A LOT!" she whispered. "Aimee and I have been playing like that whenever we can. Does that bother you?"

I thought about it a few moments and then shrugged. "Not really. I mean I can understand that you want to have sex but your dad kind of prevents that."

"Jack. My dad is only part of it. I don't WANT to date boys. Until now I've been just fine playing just with girls. Understand?"

"Ohhhhhh." I whispered. I get it. "So while this was fun and all, I'm really not what you want, right?"