Date: Fri, 4 Jan 2008 13:27:44 +0000 From: Jack Boy Subject: Jack's Cool Family chapter 4 This story is now purely cumming from Jack's twisted imagination. Please feel free to contact Jack at jackieboy1992@hotmail.com. Andy is now just playing the role of editor and proofreader, and house-husband! Disclaimer. 1. This story will involve sex between an underage boy and various members of his family, friends and others, both female and male. If you don't like this sort of story please leave now. 2. If you are too young to read the above type of material, it's up to you to leave. We certainly wouldn't encourage you to do this stuff. 3. Not allowed to read this type of stuff, I suggest you move before continuing to read it! 4. This is total fiction that has sprung from our twisted little minds. 5. This story has been created by Jack & Andy and so is copyrighted to us. Feel free to quote it, but please give us credit. If you make any money from this, let us know how so we can as well. Thanks. Chapter Four. I suddenly realised that my cock was still as hard as before, and let out a groan. I started to stroke myself again and I wanted to sit down as I normally did when I jerked off in the bathroom, but with the monster up my ass, I didn't think it would help matters. I pumped away for a few moments, perspiration dribbling down my face and chest as I tried to bring myself relief. Suddenly the door opened. I gasped in horror and grabbed at a bath towel to cover myself, before I saw it was only Jill walking in. "Thought you might need some help bro," she said, grinning. "Aw Jill you've gotta take it out of me!" I gasped. "In a minute bro," she said, looking at my straining erection. I could see her lick her lips. She pushed me back onto the toilet seat, causing me to groan as the fake cock pressed against all my sweet spots. She knelt down and before I knew what was happening took my straining cock into her mouth in one swallow. "FFFFUUUUHHHH!!!" was all I managed to get out as Jill worked her tongue on my cock. My hands gently grasped the side of her head as I watched my sister bob up and down on my stiffness. I felt my balls tighten. "Gonna cum sis!" I whispered, which just caused her sucking to become like a vacuum cleaner. My body stiffened as I unleashed a torrent, well about half a dozen, of shots of cum down her throat. I slumped backwards, leaning against the porcelain. "Mmmmm bro, you taste almost as nice as Wes," Jill said, licking her lips. I was exhausted after cumming twice in a matter of minutes, and happily saw that my dick was finally limp. "Please get this thing out of me Jill," I begged her. "Okay," she replied. "Turn around and bend over the bath." I did as she asked, and felt her hands massaging around my pucker and the monstrous plastic dick that was imbedded in me. Finally I felt it begin to ease out of me, and after a minute of it sliding outwards, I felt my rosebud stretch against the head of the dildo and with a wet pop, it came out. I immediately felt strangely empty, but very relieved that it was out of me. I suddenly felt a dampness on my hole, and looked around to see Jill wiping me with a warm, wet cloth. "You were leaking a little," she said as way of explaining. "Come on, get dressed properly and come back down, Mr Harris wants to talk to you about the swim team." She got up and left me bent over the bath, so I got myself up and hurried back to my room to change into more normal clothes. A nice polo shirt and a pair of baggy shorts did the trick and I headed back downstairs. I walked back into the kitchen and rejoined the table. Everyone was still eating the spaghetti so, as it was my favourite, I wolfed down mine like I hadn't been fed in six months. "So Jack, you up for the challenge of a first team spot?" Mr Harris asked me. "Absolutely sir," I gushed. "I know I may not win any races for a while as I will be the youngest, but it won't be for the lack of trying." My God, what a fucking suck up! Well, I was thinking about sucking and Mr Harris and not necessarily in the correct way! He reached out and ruffled my hair. "That's all I can ask Jack." We made small talk for the rest of the meal, and I couldn't help but notice that Mr Harris kept stealing glances at me. I guess it was just to make sure I was eating correctly. He left soon after we finished, and after Jill argued about putting the dishes in the dishwasher, the three of us crashed into the lounge. "Well he seems nice," my Mom started. I nodded. "He's really nice actually. He never yells at any of us." I said, backing up my Mom's opinion. "And someone who is not female and sitting in this room fancies him," Jill commented. I chucked a cushion at her, flushing beetroot red. "Jack?" my Mom asked simply. "Okay, he's a complete hottie!" I gushed out. "He has really soft hands, he's really nice and I could easily let him shower me." I still couldn't believe that I was sat her, discussing the good aspects of a male teacher that I fancied with my Mom and sister. "Jack obviously likes him Mom," Jill commented. "Why?" came her answer. Jill pointed in the direction of my shorts, and I looked down to see my previously unnoticed tent. "Need me to take care of it again bro?" Jill asked. I flushed red, knowing now that my Mom must know that Jill had taken care of me already. Mind you, my Mom had also done the dirty for me as well. "I think it's time we made sure he can take care of himself don't you?" my Mom said to Jill. Jill giggled slightly and leaned over the arm of her chair and handed me a bottle. I looked at it and saw it was a bottle of hand lotion. "You probably need that Jack," she said. I sat staring at the bottle, not really letting the thought sink into my brain that my Mom and my sister wanted me to jerk off in front of them. I took the bottle and started to get up off the sofa, but my Mom pressed her hand to my chest and pushed me gently back down. "I think we all are comfortable here don't you?" I nodded, feeling my cock begin to painfully stretch my shorts. I looked over and saw Jill take off her top, leaving herself naked on top. Man, even though I didn't really go for it, she had nice tits. I was distracted away from Jill by movement by my Mom and saw her stripping and leaving herself in just her bra and panties next to me. The whole wrongness of this crashed into my mind and I felt myself begin to deflate and become uncomfortable. I think my Mom noticed and she gently started to stroke my right leg, just above the knee. Jill had noticed as well and she had moved behind me, and started to nibble on my left ear. This close attention to my body made it respond and I was back at full mast in moments. I slid my hands underneath my polo shirt and in a swift movement, tossed it onto the floor. I moaned slightly as Jill found the inside of my ear with her tongue. I lifted my butt of the sofa and slid my shorts and briefs off and was sat there in all my naked glory. I opened the bottle and squirted some into my hand and rubbed it onto my straining cock. Now I had rejoined the show, Jill sat back down in her chair after ridding herself of her skirt and had a hand between her legs. Mom had one hand down her panties and the other still caressing my leg. It moved slowly up my body and circled my navel. I grasped at my cock, pumping it slowly, enjoying the sensations, when my Mom's hand travelled lower again. It gently held my hand on my cock for a moment before cupping my balls. I groaned and allowed my spare hand to be taken by hers and placed into her panties. I felt her wet slit, and instinctively slipped a finger inside her. Mom let out a low moan, which turned into a gasp as I found a nub of something inside her. I realised that she liked me pressing that nub so I flicked it back and forth. As I was assaulting her insides, Mom's other hand slipped lower on my body, underneath my ball sac, touching that mound of flesh between the sac and my crack. The feelings I had were unbelievable, as my right hand continued to pump my cock. I felt myself begin to shudder and let my dick go, so I could calm down and make it last. Suddenly, my Mom's fingers were at my hole, scratching it slightly, making me convulse with delight. I heard a grunt of pleasure from Jill and looked over to see her with most of her hand up her snatch. She shuddered and I saw wetness leak around her hand. During my distraction, a finger pressed past my sphincter and I let out a load gasp. Jill looked up and saw my Mom struggling with my legs and my own hand in her cunt. She got up and came over and turned me slightly, opening my legs. I continued my rubbing of my Mom's hard spot and was suddenly awash in fluid. My Mom pulled her finger out of me and grabbed my hand, thrusting it into her until I was in to the wrist. She bucked back and forth against my hand. I suddenly felt my hole penetrated again as Jill forced not one, not two but three fingers into me. She immediately found my sweet spot and I grabbed my cock with my free hand again as the feelings of ecstasy swept over me. I stroked furiously at my stiffness, while my sister finger my hole and my other hand was imbedded in my Mom's cunt. Finally my body gave into my brain's demand for release and my cum erupted like Old Faithful. I sank back into the cushions of the sofa, and was about to drift off when I felt a lapping on my now soft cock. I looked down to see both my female family members licking my boy juices from my naked body. "Aw man that was good," I whimpered out, knowing I ought to say something. We all snuggled up on the sofa, with me in the middle of course, watching the usual crap on TV. `My Family' came on, and I found myself getting hard looking at the semi naked image of Gabriel Thompson, who played the teenage Michael. He looked a bit like Jill's boyfriend Wes. "If Jack is to progress onto getting Mr Harris to play about with him, I think we need to move onto male interaction here Mom," Jill said suddenly. I boned up immediately at the thought of Mr Harris, me and a bed. "Um, what do you mean?" I asked naively. "It's obvious that Gareth likes you in a way that a teacher shouldn't," Mom started. "While I don't think you are ready for that involvement yet, you also shouldn't do anything to discourage him." My jaw dropped. Here was my Mom and sister talking through an action plan to get me and one of my teachers together! "I think that we should get your Wesley involved first," Mom said to Jill. I looked around at Jill, expecting her objections but only saw her nodding approval. "I can't wait to see my boyfriend banging my little brother's butt. That is going to be so hot!" I thought that I needed to inject a dose of common sense into the conversation at this point. "Um, maybe Wes won't want to mess around with a little shit like me, when he has got a hot girlfriend like you sis." "Are you kidding!" Jill laughed. "He's been begging me to let him have a shot at you for ages. If he got his way, you, him and another couple of my friends would be in a tent, in the woods, going at it twenty four seven!" "Ah man, look what you've done now!" I moaned, feeling little Jack at full attention again. "Stand up you filthy, randy little bastard!" Jill said suddenly. I panicked and stood, wondering what I'd done wrong. I saw the sly grin spread across her face. "I just wanted to taste you again, but couldn't be bothered to move." She took my length in and gave me another first class blow job, culminating in me grabbing her head to force my spunk down her throat before my legs quivered and gave way. "I need my bed I think," I mumbled out. Getting up, I kissed my Mom and Jill good night, with tongues of course, before dragging my naked, spent out ass upstairs and slumped into bed. I lay there thinking about my day. When I woke up, I was a scared, closeted boy, who survived day to day by hiding his feelings. At the end of the day, I'd come out to my Mom and sister, told them one of my deepest fantasies, and had the juice sucked out of me on numerous occasions while I had my insides massaged. Alright, not by a male, but surely a male finger will feel the same as a females. I fell asleep, thinking about getting it on with Wes and with Mr Harris. End of chapter. Hi there. Please let me know what you think of this. Andy has left this story to me and me alone. He is struggling through his own stories, and with several people asking for this story to continue, we talked about how to do it and decided that I would give it a bash. Andy is reading through it before we post it, but I am now in total charge of the story line! Wey and indeed Hay!