Date: Mon, 30 Jul 2007 07:19:28 +0000 From: Jack Boy Subject: Jacks Cool Family chapter 2 This story is a combined effort between Andy and Jack. As such, both of our emails are available for comments. Please email any comments to either andys_stories@hotmail.co.uk or jackieboy1992@hotmail.co.uk. Disclaimer. 1. This story will involve sex between an underage boy and various members of his family, 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 Two. Mom handed me my clothes and told me to put them on and go and do my homework before tea. I stumbled upstairs in a daze, and grabbed my school books out. I finished off my homework in a super fast time, wandering back downstairs in just my boxers to find my sister sat at the dinner table with my Mom. "Nice bod bro!" Jill said. "Shame that Mom says you bat for the opposition!" My look of horror must have been apparent as I stared back and forth between them, and I turned to flee back to my room, before my sister grabbed me. "Cool it bro," Jill said, struggling to hold me as I tried to flee. Despite the fact she was a girl, she was very strong, and I had a slight body, not being a jock. I gave up trying to get away, and she let me slump into a chair at the table. Jill pecked my cheek before returning to her seat. "Why did you tell her Mom?" I complained. Mom looked at me. "I thought she should know because she can help you." "How?" I asked. "She's a girl, not a guy!" "Excuse me," Jill firmly said. "She has a name and is sitting here ya know!" I looked at her, embarrassed, and seeing her gazing intently at me, looked away and back down at my feet. "Jack, I have a couple of friends who are gay, so I know partly what you may be going through." Jill said. "Who are they?" I asked, wanting to know, as it may help fuel any jack off fantasies that I have. "I'm not telling you yet, but I know what they went through when they came out to their families," she replied. I looked up at her. "So you cool with having a fag for a brother?" I asked. She rose suddenly, leaned across the table and slapped me hard across the cheek. "FUCK!" I yelled, pulling back, feeling the sting immediately. My Mom started towards my sister, who put a hand up to stop her. "Don't you EVER use THAT word to describe yourself," Jill hissed at me. Tears had started to escape from my eyes, as the shock of the slap wore off and the pain settled in. Jill came round the table and hugged me tightly. "I love you little bro, and you being admitting your sexuality only makes me feel more for you. That's a horrid word though. It's an insult and you should never use it. Yeah you may be gay or a homosexual, but you are not queer and you are not that word either!" I cried a little as I hugged her, and felt love as my Mom embraced both of us, and we must have been a wonderful picture postcard of family bliss for a moment. Mom let us go while she finished up with dinner. We both grabbed a coke from the fridge and Jill led me to her bedroom. Jill's room was a typical teen girl room, so I've been told. She had posters on the wall of the usual hunks, some of which I fantasised about myself. Leonardo DiCapprio before and after Titanic, the newest posters of a very hot, and now no longer a kid, Billy Gilman, as well as some photos of Wes, her boyfriend, who I'll admit was a hunk himself. She patted the bed for me to sit down, which I did. I suddenly realised, I was still only in my boxers, and looking at the hot guys had made little Jack start to wake up. I went to grab a pillow to cover up, but she brushed it away. "Jack, getting hard is the most natural thing a guy like you can do when surrounded by images he likes." My love for Jill was growing with each passing conversation. She took her shirt off, leaving just a bra on, covering her tits. She shed her skirt as well, bending over giving me a show of her butt, on purpose I was sure, as she found some leisure bottoms to put on. She sat next to me. "So you're gay, and want to be fucked by guys?" she opened up with. I had been in the process of taking a sip from the can, and ended up spraying Jill, her bed and floor. "Start with the easy questions sis!" I laughed, feeling more at home talking to Jill than my Mom about it. Jill wiped the spray of coke from her chest, laughed, before turning serious. "You know there are a lot of guys out there who would take advantage of you and hurt you don't you?" she said, concerned. "I guess so," I replied. I had read lots of stories on nifty and the like, and not just the pretty pretty ones where a kid found true love with a multi millionaire. Some of the authoritarian stories, whilst being hot in their sex description, were quite scary for a lad of 13. "So, Mom wants me to give you the un-censored birds and bees talk!" Jill sniggered. I flushed a little, before she continued. "I know you know about jerking off." She started. "How do you know I know?" I asked. "You're hardly quiet when you cum Jack!" Jill pointed out the joining wall between our bedrooms. Of course, I flushed red again, but little Jack grew a little more. "Blow jobs? 69s? Anal probing? Rimming? Full sex?" Jill started reeling off a list of the various activities. "Tell me when you haven't thought of one yet, or don't know one." "Whoa whoa," I giggled. "I've guessed at how to do blow jobs, and, um, I've sort of, um, practiced maybe, um, on a cucumber." My chin hit my chest again as I tried not to look at her, but she lifted my head. "That's exactly how I practiced!" Jill said. I felt a hell of a lot better for hearing that. Maybe I wasn't such a depraved pervert after all. "I guess I know what 69ing is, but never had the chance to blow anyone let alone get a 69." "It'll come in time, let's face it, you may have a couple of years left in you before you can't get it up any more!" she said, making me smile. "What's rimming though?" I asked. "It's where your partner makes love to your asshole with their tongue," Jill informed me. "Eugh!" I said. "I know that ass fucking obviously means sticking your cock up someone's ass, but licking it out, that's gotta be gross!" Jill hugged me and chuckled. "I love the fact that you would be cool with someone shoving a ten inch cock up you, but not their tongue!" "TEN INCH COCK!" I almost yelled out. "No fucking way has someone got one that big." I looked down at my four inches, now proudly poking through my boxer fly. Jill followed my gaze, and gasped slightly, and I saw one of her hands rub over her own crotch. "Can I look and see Jackie?" she asked, almost begged, huskily. I always had had no secrets from Jill, other than THE big one, which she now knew, so I shrugged to myself, stood up and peeled off my boxers, leaving myself naked in front of my sister. Jill licked her lips, and reached out and grasped my hardness. I felt a warm glow as she held my cock and she pushed me back onto her bed. "Let me do this Jack," she said, as she started to jerk me. I laid back, knowing that I may have trouble keeping my end up, but Jill wanted this, and she was such a cool sister that I'd do anything for her. She teased my foreskin over my head and set herself into a steady rhythm, which she interrupted herself occasionally to give my cock head a lick with her tongue. Her free hand started off fondling my balls, before probing lower and finding my pucker. As soon as she touched it, I felt a throb flow through my body, and I knew I wanted her fingers inside me. "Please Jill, push them in!" I begged. She needed no further invitation and thrust two fingers into me dry, stopping only when her hand wouldn't go in any further. I stiffened in pain, squealing out loud at the shock, before succumbing to the pleasure as she hit my spot. Jill's hand suddenly left my cock, but was immediately replaced by her mouth, her warm mouth. This was all too much for me, and I bucked and felt my balls draw up before unleashing a torrent of spunk into her waiting mouth. Jill lapped up my cum, stopping only when my cock got too sensitive for her to continue, and her mouth made its way up my body, kissing my belling button, her tongue tracing a route around my chest, pausing to suck on each nipple, before nuzzling my neck and kissing me full on the lips. I opened my mouth and we exchanged tongues and spit, and I tasted my own cum on her tongue. "You liked that huh?" Jill asked. I nodded, unable to speak for a moment. "What will Wes say though?" I asked. "For a start off, I was just helping you out bro," she said. "Wes's my boy and will be for the foreseeable! He doesn't need to know about this okay?!?" I nodded, as she had a hand wrapped around my balls and I thought it best to agree with whatever she said. "Plus, I've got another treat for you." Jill got off the bed and wandered to her closet, rummaged around before pulling out what looked like a fake dick. "What's that?" I stupidly asked. "It's a plug," Jill said. "You can get what's called butt plugs, which a lot of gay guys used to keep themselves loose, or prepare themselves with as it helps stretch them." "I've read about them in stories. They make them sound really horny!" Jill continued though, "recently though, a firm has started selling fanny plugs. It's like a butt plug, but thicker and longer. This is mine, but as I now get as much sex as I want from Wes's cock and I want you to have it." She handed the stiff rubber moulded cock and balls set to me. I slid my hand around it and up and down its length. "This is huge!" I said. "It's an 8 incher in length and three inches in thickness, more than the average man, but if you get used to it, then most cocks won't hurt you!" Jill leaned over to her bedside drawer and pulled out a white tube, and popped the lid. "This is KY Jelly, which is one of many lubes you can get. You'll need this when you fuck or get fucked okay bro, without it you'll get hurt." Jill squeezed the tube and got a generous amount on my hand. She told me to coat the plug with it. As I was doing this, I felt something cold against my hole. I looked down and saw Jill spreading my cheeks and slipping a lubed finger inside me. "If you are gonna put anything up you, a real cock or a fake one, you've gotta lube up first or you could tear something," my sister told me. Finally she took the plug out of my hands and teased my hole with the head of the dildo. I felt myself grow as I felt pleasure spread through my butt. Suddenly she popped the head inside me, and I gasped in pain. "Remember bro, this is thicker than most me, so if you get used to it, you'll be fine later in life!" she cooed at me. I gritted my teeth and told her to continue. Jill pushed slowly with the plug, and it slid into me, a half inch at a time until I felt so full I could burst. My cock was straining for release again as my prostate was tormented with the rubber cock sliding past it. Suddenly the pushing stopped, and I looked up at Jill. "That's it bro, you have all eight inches in you, well done!" She leaned in and pecked me on the cheek. "Even Wes couldn't take it all up him at the first attempt!" That definitely got my attention, Wes had had this shoved up his ass? More than once? Jill pulled me off my bed and led me back to my room, naked, little Jack pointing the way. She threw my boxers into the pile of dirty clothes that littered one corner of my room, and I should really have complained when she opened my underwear drawer. My mind was still in ecstasy with the feelings that the plug gave me every time I moved though. "Ahah! I knew you'd still have them," Jill exclaimed in triumph. With an evil glint in her eyes, she handed me my old pair of spider man briefs that I'd never got round to chucking away. I'd had them a couple of years, and with my recent growth spurt down there, they would normally be tight. However, with a major hard on caused by the eight inch dildo up my ass, no chance! Jill held the legs open for me to step into, which I did. She pulled them up, cramming my hardness into them. I then was handed one of my body tight t-shirts and a pair of shorts, again from a couple of years ago that I hadn't got round to throwing out. I sat down on my bed to put on a pair of socks, causing me to moan in pleasure as the plug was shoved further into me, Jill ran back to her room to quickly change. She reappeared at my door and hauled me off my bed, and led me down the stairs back to the lounge. She pushed me through the door first, propelling me awkwardly towards my normal spot on the sofa. I was shocked to see we had company. Mr Harris, one of my teachers from school, was sat on the sofa, right next to where I normally sat. "Ah Jack, I've invited Mr Harris round for tea as he wanted to talk to us about the swim team." Mom said. "Um hi Mr Harris," I said, shaking his offered hand. "Good to see you Jack," he said. "I'm pleased that your Mom asked me round as we need to talk over a few things." I walked uncomfortably towards one of the chairs, before my Mom told me not to be rude and sit next to my teacher. Man, the problem was, Mr Harris was a hottie, very firm body and tall and strong. I'd had his hands on my body a few times during the course of swimming coaching, nothing improper of course, unfortunately, but I was about to sit next to one of my jerk off fantasies, with an eight inch dildo up my ass. I groaned to myself, gritted my teeth and sat down. I moaned silently, so I thought, as the plug grazed my prostate again, and for the first time since it had been up my ass, I felt my cock give a little spurt of juice. Mr Harris looked at me, as I'd sat down, and I swear I saw his eyes notice my straining hard on that I was desperately trying to cover. We made small talk for a few minutes, Jill taking great delight in suggesting that I get up and fix Mr Harris a drink, before sitting back down, before again suggesting he'd like ice, and then lemon. I was going crazy inside, and my cock was leaking like a bust water pipe. Finally my Mom suggesting going to the table to eat. I grabbed Jill as we walked to the table. "You knew he was coming here didn't you!" I hissed at her. "Of course, I thought you may need some help admitting things to yourself though!" How did she know? Was I that easy to read? End of chapter 2. Well that seems a good place to stop. We'll deal with the dinner and the rest of the night in chapter three. Poor old Jack though, will he last dinner without creaming his pants in front of his teacher? Thanks to everyone who has written with their support after chapter one. We will definitely keep the story going for a while until we run out of ideas!