My friend, Jack Bennet, and I had been close since Kindergarden, we were like two brothers. We spent most of our spare time together and had now reached the ripe old age of 14.
We’d both giggled and shared our time through puberty and had no shame with each other. We had often “beat off” in each others company, staring at the latest porno mag we’d got hold of or looking at internet porn pictures.
Jack’s cock was long and thin, like him,although it appeared to be longer than mine, because mine was much thicker, my stature mirrored my cock, shorter and stout, it was the same length, yes, we had measured each other. Never had we touched each other or even thought about it, we just enjoyed being “naughty”, quite comfortable being naked and “wacking off” together.
However this time was different. Jack had been asked to babysit his little sister Emily, when his parents went out with a group of friends. They wouldn’t be back till late so Jack and me had the house to ourselves, apart from Emily of course but being only 10 years old we reckoned on her being in bed early. This gave us both a chance to raid his dad’s porno collection.
Emily was a cute little girl, I’d known her since she was born and although she could be a pain in the ass, sometimes, she wasn’t a bad kid. She had long blonde hair that hung in ringlets to her shoulders, not very tall but was now developing puppy fat around the places women were supposed to “broaden” out. She’s even started to develop breasts. I’d noticed when we went swimming, that she had started to fill out the bikini top, though only just, that she insisted on wearing. Her smile would stop an army at twenty paces and her sparkling blue eyes seemed to smile as she gave her wide eyed little girl stare.
I’d never thought of Emily as anything other than a sister until….
Emily, at Jack’s command, went and took her bath and went to bed. This was unusual as whenever I had stayed over and her parents told her to go to bed, she had always made a fuss and bother and gone very reluctantly. This meant that me and Jack could raid his dad’s den. We made our way into his “private” room and rummaged around in his drawers. Jack suddenly shouted “Mother load” as he raised his hand in the air, clutching a wad of DVDs. We quickly rifled through them, Jack pulling out one called “Teen Whores”. The picture on the front had a collection of young girls on the front, they barely looked in their teens, despite the bottom of the DVD stating “all models are 18 yrs or over”. Jack smiled broadly, “This one” he said as he pushed it into his father’s DVD player. We both sat on the small sofa, in the den, and waited for it to start. Like most Porno’s there wasn’t much plot and soon there was a collection of, very young looking, girls naked and playing with themselves, a guy came into view and started to fuck each one in turn. This gave me and Jack the nod to pull down our shorts and start playing with our, now swollen, pieces of meat.
We sat, our arses pushed forward on the sofa, stroking our hands up and down our respective cocks, Jack noticeably breathing deeper and harder than I was, he was really getting off on this one! Jack, his face starting to contort in ecstasy turned his face to me and stopped pulling his cock. He suddenly asked me“Have you ever had anyone else wank you off?” I stopped too before looking at him, instead of the screen and replying “No, you know I havn’t”. Why he had asked I don’t know as we had always, as far as I knew wanked off together. “Ever thought about it?” He asked. I pondered on where this was going to lead. I’d never had any gay leanings but didn’t want to upset my friend either. I looked down at his cock, his hand wasn’t now wrapped around it and it was sticking up proud, straight in the air. I let my grip go as well, my cock mimicking his, sticking up in the air of it’s own accord.
So there we both were, silent, porn playing on the T.V. screen and cocks waving high in the air like two snakes being charmed.
Jack slowly slid his hand onto my cock, wrapping his hand around my shaft and giving a little squeeze. It felt great, the first time anyone else had ever held my cock, even if it was a guy. Jack started to slide his hand gently up and down my cock shaft, rubbing his thumb over the tip. If I hadn’t been so surprised at what was going on, I would have probably shot my load there and then. Jack motioned his head, silently instructing me to take hold of his cock and return the favour. I tentatively placed my hand around his hard-on, it felt weird holding another guys dick but as Jack continued to pump me I started to do the same to him. After all it was just like having a wank with your own hand, it was just your best friend’s was hand doing the work, I tried to rationalise the situation to myself.
It was then that I became aware of another presence in the room. Somehow Emily had managed to sneak in and behind the sofa. “Not fair!” she suddenly screamed. It took my by surprise and I jumped up off the sofa. I didn’t even have the presence to hide my cock in my hands and just stood there, stark bullock naked, facing Emily, half hidden behind the sofa, with my cock on full display. Jack, very nonchalantly, just turned his head to his sister, behind him, and said “Sorry sis…what took you so long?” I was flabbergasted. In my confusion I still hadn’t covered up and now noticed Emily, biting her bottom lip and those eyes, those beautiful blue eyes firmly fixed on my cock.
Jack broke the ice, patted the sofa next to him and beckoned his little sister next to him. “C’mon sis, sit here”. Quite obviously this was a set up! “What’s going on?” I asked my friend. “It’s o.k” Jack replied “Everything’s cool”. Emily literally plonked herself down next to her brother, still with her eyes fixed on me, she took hold of his cock, her hand sliding almost on auto pilot onto his lap. “C’mon” Jack gestured me to sit the other side of Emily, “She’ll do you to”. Needless to say I had questions.
“How long has this been going on?” I enquired. Jack gave me a big smile and a wink, “She caught me last week and being curous and all that, well things led to us, kinda, you know”.
Emily was wearing just a loose fitting Tee-shirt, I had noticed, as she had made her way around from the back of the sofa, that it barely covered her butt cheeks, clearly she wasn’t wearing panties, made all the more obvious as she sat, knees apart, next to her brother. I could just make out the slit of her pussy, all bare. The first real girls pussy I had ever clapped eyes on. I sat next to her, she smiled and took hold of my cock, in her other hand. Her small hand wasn’t big enough to wrap all the way around my shaft and it felt cold, however I had a girl holding my cock, a pretty girl holding my cock, even though she was only 10!
Emily dutifully stroked her hands up and down our respective cocks, it was clear that it wasn’t the first time as her pace and rhythm were just right. Emily was sat, cock in each hand with the biggest smile on her face, Jack, slouched right back on the sofa, had his hands on the back of his head, eyes closed. His breathing got faster as his sister pumped us both. My own orgasm was prolonged, probably because I couldn’t believe what was happening, It didn’t take long for Jack shoot his wad high up onto his chest. Emily squealed with delight and started laughing, the trembling of her hand, as she laughed, made my inevitable orgasm arrive soon after, cum shooting onto my stomach. Emily kept pumping us both until cum barely trickled onto her hands. She coolly licked one and then the other. “Hmmph” she went, “Tastes about the same”. I looked on in awe.
“What the fuck was all that about!” I eventually said to my best friend. “It’s cool, it’s cool” Jack replied as he stood up. Emily was sat, grinning like a Cheshire Cat. “C’mon Em.” Jack said, “Stand up”. Emily duly stood. Jack took hold of the bottom of her shirt, lifted it high over her head and threw it to one side. From where I was sat I had the perfect view of her widening, almost womanly rear. “Wanna have a look?” Jack asked as he pushed Emily back onto the sofa. He knelt in front of his sister and, roughly, parted her legs. I could see the top of Emily’s slit and the top of Jack’s head not far from it. “C’mon ‘ave a look see” he beckoned me. I knelt beside my friend, now looking straight up between the little girls legs. The top of her thighs parted to give a clear view of her naked, bare pussy. Jack stuck out a finger and slid along her slit. Emily giggled, very much enjoying the attention. Jack licked his finger and tried to force it up into her virginal pussy hole. Just the tip went in before Emily shouted “Ouch!” “How long you two been doin’ this?” I asked. “ ’bout a week”, Jack replied before quickly licking his finger and tried to reinsert it into his little sisters’ hole.
“She’ll wank me off but she wont blow me”, he went on, “tutting” as if the emphasise the point. “I’m not putting your thingy in my mouth!” Emily exclaimed, looking crossly at her big brother. “I might yours though” she then said, looking down and smiling at me.
I was that engrossed in watching Jack sliding his finger into his sister I didn’t hear her say it. Jack however picked straight up on it. He nudged me, “Go on stick your cock in her mouth” and almost pushed me over. Somewhat dazed I stood and knelt on the edge of the sofa, offering my cock, even though I had come just moments earlier I was still hard, such is the benefit of youth. Emily took hold of me and drew my cock towards her face, she looked up at me and then engulfed my cock in one large mouthful, she gagged and pulled it straight out again. With a look of disappointment she tried again, this time taking it a bit slower. She wrapped her lips around the end of my cock, which was awesome as it was, and then slid it between her lips. I felt the warmth and wetness of her mouth on my cock, this was heaven! I slowly started to push my cock in and out of her mouth. I was getting my first ever blow-job!
I looked down at Jack, he was now licking his finger again but instead of putting it back into his sister’s pee-hole he put his face forward and licked Emily’s slit. Emily jumped and almost swallowed my cock. “Mmmmph” she mumbled as she pushed me back, “What are you doing?” she pointedly asked her brother. “Dunno really” he replied, “Just seen guys doin’ it on the porno”. Emily took hold of her brothers head, by his hair, and pushed his face back between her thighs. “Do it again” she commanded. Jack obliged and Emily slid my cock back into her mouth, she was now sucking on it. I don’t know what Jack was doing but it certainly had an effect on his sister.
Having just cum, minutes earlier, I managed to hold myself back longer than I thought. I had always imagined suffering from premature ejaculation if I was ever fortunate enough for a girl to do this.
Jack, lapping at his sisters snatch, pulled back, “Wanna fuck Em?” he asked. Emily, who for the first time looking concerned, narrowed her brow and looked up at my face. I didn’t know if it was for support or protection, I just kept fucking her mouth. Jack reached into his trouser pocket, laying discarded on the floor and pulled out a tin of Vaseline. Was he prepared for this or what?
He picked his little sister up and carried her to the glass coffee table, in the lounge. With one sweep of his arm he cleared the magazines of it and lay Emily onto it. She arched her back as she felt the cold glass come into contact with her body. This had the effect of her pushing her tiny boobs into the air, making them look much bigger than they actually were. I took the opportunity to fondle what little there was. Her boob hardly filled my palm but her hard little nipple did kind’ov jab it, as I passed my hand over.
He undid the lid of the Vaseline and coated his long slim cock, smearing it all along the shaft. “You’ll need some of this sis.” He said.
Jack had always been the more forward of the two of us, knowing things about sex, he was my best friend and my tutor. He lifted Emily’s knees towards her chest and lined his cock up. Emily again looked up at me, this time with worry on her face. “I don’t think we should be doing this” I said, now belatedly concerned for the little girl. Jack ignored me and pushed the tip of his cock into her vaginal canal. Emily bit on my cock as she was engulfed in pain. “Owww!” I screamed. “Oowwwww!” screamed Emily as her brother pushed, forcefully, his cock even further into her. Emily pushed me away and craned her neck to see her brother violating her, pushing his meat into her too tight pussy. “Jack no!” she screamed at him. Too late, Jack was now pushing and pulling his cock in and out of his sister, eyes tight shut, Emily lay back and endured the inevitable fucking she was getting from her big bro’. Lust still flowing through my veins I offered her my cock to suck again, Emily opened her eyes just long enough to see what I wanted and opened her mouth. Once again I was mouth fucking her.
“This is fucking great Em. Jack said as he ploughed in and out. Emily just grunted. “C’mon lets swap” he said to me as he withdrew, pulled me to one side and replaced my cock with his into Emily’s mouth. “Coat it with gel”, Jack gestured to me. I took a swab of the Vaseline and lubricated my own cock, pointed it between the young girls vagina and pushed. I may have mentioned, earlier, that although the same length of cock as my friend, mine was much thicker in girth. I could feel, and see, young Emily squirming beneath me as I tried to push my cock in to her. Lust was fighting with my conscience as I managed to push further and further into her. I could see that she was in pain. I could feel her pussy walls scraping my cock shaft. This wasn’t pleasant for both of us, if the truth be known. A couple of thrusts and I pulled out, I couldn’t watch the pain on this young girls face. “Nah, swap again”, I asked my friend “I prefer her mouth” I lied. Jack wasn’t bothered which hole his cock went in, as long as it was one or the other. I re-took my earlier position and I think Emily was grateful as her breathing seemed more relaxed. So there the three of us were, all fucking for the very first time, when suddenly I felt a large hand on my shoulder, “What the fuck are you two doing to my little girl!” It was Jack and Emily’s mom. “Oh shit” I suddenly cried out, seeing Jack’s mom’s other hand on his shoulder I heard Jack cry out, “Holy fuck!”
“What are these two horrible boysh doing to my little girl?” cried Emily’s mom. “Boysh” I thought to myself “Boysh” I realised that Emily’s mom was a bit the worse the wear for drink and slurring her words, could this be our salvation? Mrs. Bennett knelt and leant over the sofa, cuddling her young daughter, “There, there sweetheart” she reassured. Emily wrapped her arms around her mother for comfort before Mrs. Bennett stood, turned and glared at us two boys. Hand on hips, glaring she lunged forward and took hold of both our cock at the base of their shafts, “So!” she exclaimed.
More to follow…….
Mrs. Bennett was a statuesque woman, Amazonian in fact. She had her blonde hair cut short, had legs that seemed to reach the sky and must have been a “D” or “DD” up top. She had a beautiful chiselled flawless face, fill lips, bright blue eyes and high cheek bones, which were glowing red!
She pulled us by our cocks towards her, the stench of alcohol on her breath. “It’s a good job I came home early” she said as she balanced herself by pulling on our man-hoods. “If your father hadn’t gone playing cards I wouldn’t have been back so early” she slurred at Jack. She looked down at what she had in each of her hands, “So you two think your old enough to fuck do you?” she questioned us, stood stark bullock naked in front of her. I know it must seem strange but seeing her stood there, in a halter neck dress, obviously no bra, as her nipples could clearly be seen through the thin fabric, her pendulous breasts heaving and swaying as she spoke, made my cock even harder.
In one awkward movement she swam her arms up and through the halter neck in her dress. It fell to reveal the biggest and most perfect set of tits I had ever seen, porno mags were nothing compared to these beauties. She grabbed both us boys by the hair on the back of heads and pulled our faces onto her ample bussoms. “If you are going to fuck then you’d better learn how to do it properly”, she informed us as she pushed a nipple into each of our respective mouths. “Now be gentle but suck hard” she tutored us. It didn’t make any sense to me but having a grown womans’ nipple in my mouth, who was I to question? She swirled our heads around, I was having difficulty breathing, my nose and mouth filled with bossom. I flicked her nipple and bit on it gently. She moaned as she pushed our faces, even firmer. Onto those beautiful mounds of flesh. This went on for what seemed like hours, I wasn’t complaining. Mrs. Bennett pulled us, by our hair, of her bussom, she slid her hands down her waist and pushed what was left of her dress, clinging to her hips, down and stepped out of it.
There she stood, a real woman, a real shapely woman, a “Dream woman” in just a skimpy white thong. She hooked her thumbs into the waistband of her thong and precariously, teetering on her high heels, slid them down her legs. “Oh my…” I thought to myself, “If ever there was a picture of the perfect woman, here she was stood, NAKED, in front of me!” My eyes followed every smooth curve and contour of her body, down between her legs and to her “sex”. She kept her pussy clean shaven and apart from the hint of a shadow you would never know that she had ever had hair on her. Her pussy lips were slightly parted and I could see her inner lips glistening with juice.
She tottered backwards and made her way back into the den, she fell back onto the sofa, flew her legs wide open and then commanded us, in a slurred tone “Eat my pussy!”. Jack and I looked at each other, shocked, excited, bewildered. Mrs. Bennett put her arms around her daughter, still sat on the sofa next to her, “And one of you eat her pussy too!” she instructed. As I was opposite his mother, and Jack opposite his sister, I got to launch myself at his mom.
I dove straight in, having never licked a pussy before I hadn’t a clue what I was doing, all I knew was what I had seen on porno films. My tongue lapped up her pussy, rewarded by the most heavenly taste of her juices. I caught, what I was to find out later, her clitoris, with the tip of my tongue and she gave out a load “OHHHHH”.
Like I said, I hadn’t a clue but I knew she liked it so I copied my previous motion, to be once again greeted with an “Ooooh” as I reached the top of her slit.
Emily was giggling at Jack, as he copied me. It was obviously tickling her and she now seemed relaxed and enjoying his attempt. A few more laps and Jack pulled me from between his mother’s legs. “Swap” he said as he replaced me. I knelt up and looked at Emily, she smiled and parted her legs, I placed my tongue on her slit, she tasted different to her mother, hard to describe, just different. I reapeated what I had done to her mom. Emily stroked my hair as I, much gentler than I had to her mom, licked away. Both girls were now breathing deeply, both relaxed and enjoying our young boys tongues.
Mrs. Bennet gave out a long “Ooooo” and sat upright, before laying back down again. She had clamped her thighs on Jack’s head and I saw him visibly shake it as she released her grip on him. “Time to swap again” said my dazed friend.
I took hold of Mrs. Bennett’s knees, parted them and once again dove forward, as I did Mrs. Bennett slid forward on the sofa, almost slipping off it and my erect tongue, aiming at her pussy, found it missing it’s target. It did, however, slip into her other hole, her rear hole. I didn’t, at first realise my mistake until I tasted a tangy, salty taste on my tongue. “Oooh, you naughty boy”, Mrs Bennet said as she grabbed my head and forced it back between her legs, “Do it again, you naughty, naughty boy”.
I stuck my tongue out as far as I could and dipped it into her anus. Yes it was tangy but not too bad, I thought to myself. I’d seen butt fucking before, on films and Mrs. Bennett was quite obviously a woman who enjoyed a little attention to her rear, brown hole.
I felt her fingers and hand on the top of my head, it soon placed itself on her pussy. She began to rub herself as I tongued her anus. Pretty soon she was thrashing about and juices squirted from her pussy, my face getting coated with her cum.
Standing she dragged her son back into the lounge, it was now his turn to feel the cold surface of the coffee table as she lay him back onto it. He gave a sharp intake of breath and an even deeper one when she straddled him, putting his cock into her vagina. “Mmmm” she mumbled, “A bit bigger than your dad” she informed him, holding, guiding, his cock as it slid inside her. Not wanting to be left out and preferring the older woman, I followed them through. Mum and son were kissing but she soon broke off to take my cock in her mouth.
Mrs. Bennett devoured my cock, I even felt it slide down her throat! Her full lips coming into contact with my balls. “Not bad eh?” said Jack, “Me fucking my mom and you fucking her face”. He reached up and juggled my balls as I thrust my cock into his mother’s mouth. “Not bad at all” I replied. A full grown woman and we were fucking her at both ends!
I moved my knee up onto the coffee table to get a better thrust and knocked the tin of Vaseline onto the floor, Mrs. Bennett must have noticed as she took my cock from her mouth and told me to pick it up. I did as I was told and stood in front of her, tin in hand. “Why don’t you put some of that on that big cock of yours and help Jack out” she said, nodding her head towards her posterior. I took a dollop of goo and once again coated my cock as I made my way around to her voluptuous, heart shaped rear.
To be honest I wasn’t sure what she wanted me to do. Did she want me to put my cock in her pussy, along with Jacks? Did she want me to put it up her bum? Surely that would hurt her? Thinking back to how she liked me licking her arsehole I decided on sticking my cock up her bum. I straddled Jack’s legs, lined my cock up and gave one hell of a push. Surprisingly I slipped in relatively easily, although tight it wasn’t anything like as tight as Emily’s pussy.
I could feel Jack’s cock through the thin membrane which separated our the respective holes our cocks were penetrating. I timed my thrusts with Mrs. Bennett’s, onto her son’s cock. Our balls kept touching, which was weird and Mrs. Bennett started to groan, loudly. Her long low groans sent vibrations right through her body and I could feel the trembles rippling through her body as well as my friends cock sliding in it’s nearby sheath.
Mrs. Bennett got rougher and rougher as she threw herself back onto our cocks, faster and faster she went until she suddenly stopped, gave out a long loud groan, wiggled her arse and gave a long breath out. The three of us lay still for a while before Jack asked, “Can we swap mom?” Mrs. Bennett, dripping in sweat, clumsily climbed off her son. Jack got off the table and gestured me to lay on it. The table wasn’t as cold as earlier, though it was sweaty. I lay down and watched Mrs. Bennett straddle me, glazed eyed she, like she had done with Jack, lowered herself onto my cock. She leant forward and I grabbed the opportunity to fondle her boobs, much firmer than I had imagined, given the size.
Her pussy felt warm and welcoming, made to fuck, unlike her daughter’s pre-pubescent vagina. Her pussy was like a warm wet glove wrapping itself around my cock, (not that I had ever tried a warm wet glove, honest!).
Jack, having prepared himself, pushed his cock up his mothers’ bum hole. I felt it slide in along it’s parallel sheath and once again our balls came into contact.
With my mouth I grabbed at the older woman’s breasts, nipping her large brown nipples, with my lips, softly biting her globular mounds of flesh, hanging from her chest. My cock felt as hard as it had ever been, I could feel Jack’s cock shaft pressuring mine. Mrs. Bennett’s wet pussy slammed down onto my crotch, my pubes were soaking, she took me into her whole, grunting as my cock reach the very depths of her. She rode me as if I was her stallion, only put off slightly by her son’s actions knocking off balance now and then.
My balls tightened, my cock swelled and I gushed seamen deep into her very depths. I’m sure I felt Jack’s cock swell and cum as well as he shouted “YESSS…YESSSS”.
Mrs. Bennett, being filled with our sperm had her own orgasm. Her pussy walls clamping and releasing my cock as she enjoyed her pleasure.
She collapsed her whole weight onto me, her breasts acting like buffers between our chests. Jack withdrew and came and gave me a “High Five”, even though I was laid horizontal, his mum on top of me. Mrs. Bennett seemed to be unconscious o top of me, I looked over to Emily, Jeez Emily, I had forgotten all about her.
She was just in view, on the sofa in the den, her on fingers inside her pussy, head back and the biggest grin on her face.
Mrs. B. finally came around, she grabbed my face, kissed me passionately on the lips and climbed off my now flaccid cock. She wiped the palms of her hands across her face, as if to keep her eyes open and then resumed her earlier position, hand on hips.
Cum was trickling down the inside of her thighs, from both recently filled orafices as she looked over to her daughter and raised a hand, pointing a finger at us two boys.
“Now you two listen to me”, she said trying to look serious “Don’t you dare touch my little girl again…” she sucked in some saliva that was drooling from her mouthand then continued, “If you want to fuck you can fuck me, as often or as little as you like….just don’t tell anyone”. With that she gathered her clothes, picked up her heels and staggered away.
Jack and I looked at each other dumbfounded. Emily had quickly arisen and followed her mother, I heard her asking, in the distance “Oh please mommy let them fuck me as well”. Mrs. Bennett sternly replied, “Not until your older!”
True to her word Mrs. B. regularly fucked our brains out, it seemed as though she sometimes engineered our time together. She always let Emily watch but never join in, save for her kissing her youngest’s lips occasionally.
Unfortunately my family moved a long way a way a year later and I lost all touch with Jack, Emily and their mother.
By chance I met Emily years later. Her ringlets had given way to soft curls. She was as amazing looking as I remembered her mother, slightly smaller and only filling a “C” cup, but when I say filling I mean FILLING.
We ended up shacking up together in a flat, her mother making frequent long trips to see her darling daughter. I leave your imagination can work out the rest, save to say mother and daughter got on very (very) well.