My best friend’s brother and I have a night of wild naked fun.

18 year old girl goes after a much older man

The total destruction of Alyssa
Our school was rough, not only was it feed by the kids of the estate but all the other local council estates. Now the Waz, the Mains and the Hall had nothing on us, the rule of law still existed, but they were not nice places. The school picked its battles over discipline very carefully, a lot of the big thing got push aside, and little things where focused on in a hope of forcing us to conform in some way. While you could sell cigarettes on any playground, the toilets where full of pot smoke and fight where overlook so long as you stopped hitting the other person once they had stop moving they came down heavily on lateness and uniforms.
The uniform was simple a white shirt, grey pants, black shoes, a tie done properly and a blazer. Any deviation was jumped on a punished until it was just easier to do it right. The blazer was a good idea for the pockets, you could always carry something around with you, and the tie was the only thing that made a problem because once you put train tracks in it most people couldn’t afford a replacement so that was given some slack. Girls had a little more choice, they could wear pants or a pleated skirt.
This resulted in being able to tell what type of girl you where talking to by what she was wearing on her legs. They split into roughly four large groups but there where subgroups. The first were the normal girls who wore pants the same style and cut as the boys, these where most of the girls and it was mostly because they were cheap. Then came the popular set, they wore skin tight fitted pants, these cost more and you got some overlap from the first to them as girls rose up and dropped down, these girls were fun to look at but they a bugger to get the pants off so the was little chances of sex with them, real prick teases. Then came skirts, officially they had to be knee length, but that didn’t happen. Geeks and Nerds wore them long, near ankle length, which did nothing for them, and was like wearing a big bully me sign, but did leave you wondering what they had underneath. Lastly they where the sluts, skirts as short as they could get away with, sometimes just covering their arse, but it wasn’t to show off their legs, which was nice enough, but for easy access when I lad wanted to fuck them.
Amy and Charlotte were long skirt girls but being linked to me made real bullying unlikely, Lexi wore whatever she wanted and slapped around anyone that didn’t like it. Alyssa was a long skirt girl but she had no one to look out for her.
Alyssa was a stuck up, posh, southern swat who up until two years ago had everything. Well everything by estate standards, she was upper middle class, and she had lived in a nice big house in a suburb outside London. Her dad was some kind of banker making good money, she had gone to a privet school, and had her own horse. Then things in her life had gone badly wrong. There had been fraud charges, bankruptcy, jail for the father, divorce for the mother, and nasty rumours about photos found in daddy’s things when he was arrested. The money, the house, the school, and the horse where gone. I don’t know what possessed her mother to move up north, just to try and get away from the scandal I guess, but she did and they ended up on our estate. When she had show up on the estate at the start of the school year she was like everyone else then penniless, from a broken home, with an imprisoned father, she should have fitted right in but she didn’t because she didn’t want to and that put a target on her back.
She thought she was better than us and acted it, she made no attempt to fit in with the gang society we lived in and so she was pushed around. Most of the bullying was casual but unlucky for her one girl took a real dislike to her. That girl was Helen the Harpy, but the where few who called her that to her face, she was the highest ranking Dead Head girl still at school and that gave her a real power base, she was a skin tight pants girl all the way, she was a proper Bitch. If Alyssa had been smart she would have took the abuse, taken Helen’s shit for a few weeks and she would have gotten board and moved on to another victim but in Alyssa head she was still in a world that worked. She told on Helen, I remember the first time I heard that I laughed, telling a teacher was one step away from grassing to the police. Life got worse for Alyssa, being a ‘grass’ was not something you wanted to be, and Helen didn’t move on.
The bullying got worse, with lads we just hit you and call you names not that it can’t bad, but teenage girls have a vindictiveness and a nastiness that boy just didn’t have the attention span to achieve. You never got the whole storey but the where rumours about how bad it got. Alyssa got back by telling, not just for the bullying but about anything she could find out on Helen, if Helen cheated or stole or wagged a teacher found out. It was a vicious cycle and I like to watch it, I didn’t like Helen or Alyssa, I could have let it go on forever until Alyssa made one last big mistake. She told on how Helen was hiding her cigarettes.
The cigarette trade was hard, with drugs so long as you held your corner and kept your supply there was little business involved the price was set, but cigarettes changed. Once week you could have gotten hold of cartons, sometimes from shops but most often from a guy someone know that have come in from France or have fallen of the back of a lorry and those weeks the profits where big, hell half the time you had helped them fall of the lorry, but sometimes you had to buy packs you had to keep the price up to make anything and then people went elsewhere. To plan you needed to find a way to keep people coming back to you.
The latest way was Fast Eddy’s idea, I hated the lad but I could see why Bob kept him around, he was smart. There are these felt tip pens/markers that are quite common in British schools they are orange with different coloured tops, well if you ripe the colour out of the middle it is almost the exacted size of a cigarette. Eddy had found this gives you a perfect place to hide them and he was the first to figure this out. The Dead Heads began to sell them set up like this and give money back for refills and this improved our cash flow for several weeks. By the time that Alyssa grassed this in some of the other gangs had begun to catch on and the money was shrinking but she still cost us money. With that she had gone from being Helen’s problem to being a gang problem and that was not a place you wanted to be.
I was given orders to help Helen punish Alyssa for fucking with the gang. Another of Eddy’s bright ideas was to set up a network within the school, though blackmail, intimidation and bribery a small chuck of the school staff did our bidding. I had expanded it somewhat and was now running it, mostly they just look the other way while we did things but we could ask for ‘favours’. Most of the cleaning staff came from the estate and where on nowhere near enough money to mean that slipping them £10 a week was not a small sum. Cliff, the care taker, had a soft spot for a pro on the estate that was the wrong side of 16 and we had found out about it. We knew a Maths teacher who was gay, unlucky his wife and the school had no idea, so he worked for us. Two of the English teachers where having an affair, an RE teacher was sleeping with one of his students and the young female Science teacher and her best friend lab tech had a coke problem which I was feeding. Then there were the teachers who were just plain scared of us.
I was to give Helen access so she could hurt Alyssa. Now I would have responded by breaking a few fingers, that was the tried and tested Dead Head punishment, it is quick, effective, and surprisingly easy to do and wouldn’t mean cashing in any chips, but Helen had other ideas. That is why she found me in the library.
Helen was beautiful, it doesn’t matter how you spun it she was, deep green almond shaped eyes looked out from a perfect face, high cheeks, small nose, pointed chin and these perfect lips, just big enough with just the right kind of pout, her hair was long, strawberry blond and seemed to fall almost automatically into set waves, the small dimple on her left cheek when she grinned was just enough of an imperfection to make the face real, without it you couldn’t believe it. She had the body of a model, really, long and lean and sleek, with swelling in just the right places to make her sexy, her skin looked soft, smooth and faultless and just the right colour to look tanned all year around. She was so attractive it was almost imposable but you still didn’t want to date her because no matter how perfect she was physically she had a truly black soul, as I said she was a proper Bitch.
And following Helen like a faithful dog was a girl call Sam. Sam was not beautiful, the best thing you could say about Sam was that she had a great personality, she was that kind of girl. She was fat which did give her big boobs but didn’t do much else for her, her skin was bad, she had to keep her hair very short or it became completely unmanageable, and even thou her face could be seen as cute and acme scars and bad glasses really did spoil it. But she really did have a great personality. She had been Helen’s best friend forever and no matter how badly the girl treated her she stuck around, after they had hit puberty Helen had begun to make up for Sam physical shortcoming by turning her into a real slut. With Helen’s say Sam had been passed around and used up by most of the gang, she was quite good at sex now, practise does make perfect, and still she was Helen friend. She was nice to talk to and good in bed but really not attractive. Sam was a short skirt girl.
I was reading with Amy, I was now on real novels and she was really just there to help if I got stuck on the longer words even if I was still slow. I made sure that I finished the page before noticing them, I didn’t care how much clout Helen thought she had I was a chief, she waited for me and I was making damn sure she knew it. I even nodded at Sam first which would have started something nasty if she didn’t need me.
“Alreet, so I have got my orders, why you need me I have no Idea, but what do you want?” I asked.
“I need that bitch alone” she said.
“There are plenty of times when you can get her alone, why do you need me for that?”
“I need to make a statement, she need to see our power” you will be surprised how much our can sound like my “We need to tell her that people do as we said, and anyway I am going to need a lot of time with her in a place where people can watch.”
“People?”
“Aye people, you are going to get her put on detention, an hour tomorrow should do, so me and the other Dead Head girls can have some fun. They have to all be there.” With that she pulled Sam of Prophet who she was heavily flirting with the lad and headed out.
Detention where not hard to arrange, when someone still followed the rules, half the time we pulled string to get people out of them. You just had to find a teacher who’s lesson she was it that we had some pull over and put in a word, worst comes to worst just make sure they ran into said teacher and get them to do something wrong. This time it was Miss Haze, our science teacher coke addict, who we pull in. It cost me about £20 worth of product a week to keep her on side but it was almost worth it just to see the pretty young thing beg for it when it came to paying up. We set up a near riot in her lesson to give her cover and when it had quietened down we had a girl go ape shit at Alyssa so she put them both on a hour’s detention tomorrow night just as I was told.
Then it was just a matter of waiting for the show to begin, I sat around outside the labs and waited as the Dead Head girls still in school showed. Helen and Sam got there last, making some kind of point about power to the other girls that was lost on me, showing up first gave you the advantage of ground as far as I was concerned.
“Where the fuck is Amy” she whined.
“She did want to come, I said she didn’t have to” I said.
“You fucking retard, I told them they had to come, who do you think you are yo…” she didn’t finish. I slammed her into the far wall, one arm across her throat pinning her head in place, the other was between her legs pressed up against her crotch, lifting her feet off the floor. My face was inches away from hers, I enjoyed the look of panic in her eyes.
“There are a total of 8 people in the world that I let talk to me with disrespect, what makes you think you are one of them slut” I spat the words into her face at a low growl.
“Eddy will kill you” she hissed back.
“Eddy” I laughed “I have been giving him reason to come for me for years and I am still here. Do you really think he is going to make something over the likes for you” I had begun to slowly grind my forearm into her crotch “I could do anything I wanted to you, remember that before you speak to me.”
I dropped her, she almost hit the floor, “Now I said she didn’t have to come, and that goes for anyone else, you can leave now if you want to. Unless anyone has a problem with that” I said over my shoulder at Helen. No one move away, she was mad as hell and while I could protect my own they doubted I could them, that or they wanted to be there, luckily she was about to have Alyssa to take it out on. I walked into the lab.
I ignored the girls and what they were doing and walked straight over to Haze but before I reached her there was a single scream from the other side of the room followed by a smack. Now Miss Haze was a piece of work, you know the teachers, fresh out of school, young, hip, wanting to be the kids friend and to change the world, if she had landed in a nice middle class school I am sure she would have been every child’s favourite. Young enough for the girls to relate to and for the boys to have a crush on, and the was plenty to have a crush on, petite with a sweat little set of curves, short bleach blond spiked hair and a habit of wearing low cut tops. But she hadn’t ended up in a nice place, she had come here, at the time I think she pick it so she could make a differences, showing up at our school with a nasty little choke problem it was only a matter of time until she became someone’s prey.
“I did what you asked Rave” she said, getting excited as I got close to her. I didn’t say anything, let her twist, just moved closer until we where inches apart. She was breathing hard, eyes wide with fear, but it wasn’t fear of me it was the fear that I wasn’t going to give her what she needed and she really needed it.
“Please Rave… you promised… I did just what you said… please…” She was biting her lower lip, tears of panic forming in the corner of her eyes. She pushed her arms together forcing her chest up, her fingers began to trace lines along my chest, it was a clumsy attempt at flirting and if I wasn’t here for something else I would have seen how far I could push her. Addicts, I will tell you they will sell their first born for the next taste. I held out my hand and Lexi passed me a vial, the look of relief and gratitude on Haze’s face as I pushed the product into her grasping hands was almost pitiful.
“Now fuck off unless you feel like watching the show”
“Yes, thank you, thank you, anything you need just let me know, thank you” She said as she more or less ran for the door, I pretty sure she was head for the bathroom not home, she looked damn good from behind and I wonder ideally if next time she needed it I would make her fuck me for it.
“You told me not to play with addicts like that” said Lexi “it make it less likely that you get repeat business.”
“True but where else is she going to go, anyway next time you can give it to her, see what she will do to you for it” Lexi looked at me as if I had just suggested killing kittens with a cheese grater “anyway you can go now if you want”
“No I want to stay and see what the Harpy is going to do” she with an evil glint in her eye.
“What did poor little Alyssa do to you to make you hate her so?” I asked sarcastically.
“She touched my arm once” are well in Lexi book that was a big sin, I stopped making jokes, you did not touch her.
I leant back onto the wall and watched the scene on the other side of the room. Helen had wasted no time in starting to have fun with Alyssa, the beauty had the girl bent over a table, her tiptoes just touching the floor with Sam holding her down on the other side of the table. Alyssa’s long, blonde hair was a mess, her cute face was contorted in fear, tears forming in the corners of her baby blue eyes. I big part of my libido was getting turned on by the girl’s terror. Helen bent down, her perfect arse pulling tight inside her pants, and grabbed the bottom of Alyssa skirt. She rose it slowly, crawling up inch by inch, exposing more and more of Alyssa porcelain white skin and toned legs. Once she reached the top she push the skirt up onto her to girl’s back and then stood back to look at her prize. The white cotton panties that covered Alyssa arse almost match her skin tone perfectly, and what a arse it was, you have to like the backside of girls who are into horses and before her fall from grace Alyssa had been really into horse, toned, firm, a little on the large side it was a real peach of an arse.
Helen grabbed hold of the middle of the panties and pulled them up tight, forcing the white cotton hard between her legs and turning Alyssa’s whimpers into a shriek, she gave a last tug and let go, leaving the panties bunch in Alyssa’s arse crack and leaving more of her backside on view.
“You know” Helen said with an evil grin “I have so much planned for you but I think I will start with something simple. You have been such a bad girl, grassing on me you slut, and bad girls get smack” and with that she brought the flat of her hand down onto the exposed flesh of Alyssa left arse cheek with a loud crack. She didn’t stop at one, she kept swinging, hitting Alyssa arse over and over, each impact coupled with a little moan of pain from the girl getting louder as the skin got more used. When Helen at last stopped raining down blows she was breathing hard, her high checks where flushed and she was shacking the pain out of her hand. Alyssa’s arse cheeks weren’t pail anymore but now an angry looking pink, tears ran freely down her face cutting black tracks with her mascara. Most of the other girls in the room found great amusement in this, but weather it was just because they were not the one Helen was hurting or if they really liked it I can’t say, Lexi was clearly happy with the way things were going.
Then Helen’s eyes found the meter stick, and meter long wooden ruler with enough flex to course some real pain. She picked it up with sadistic glee and gave it an experimental swish though the air, the noise sent a wave of panic though Alyssa but she was held fast. Helen cackled with laughter at the terror of her new play thing and brought her improvised cane down onto the girl backside. It wasn’t a moan of pain of even really a scream but something along the lines of a wail of agony that forced its way passed Alyssa full lips upon the impact. The vivid line left on the flesh of her arse was far from pink, a deep angry red edging towards purple. The long implement wasn’t very accurate and Helen’s second swing went low crashing into the back of Alyssa legs, leaving another viscous red strip along her upper thigh. Helen kept swinging forcing louder and louder screams from Alyssa until she got the one she wanted.
it was on the seventh downward stroke and her scream had descend to rambling and begging that Alyssa said that was her last mistake “Please! Please stop! I will do anything you want, just stop”
Helen let the last blow fall anyway and then stopped, looking at Alyssa in a different way “So you will do anything I want?”
“Yes” Alyssa answered in a small voice.
“I can do anything I want to you?” Helen hand moved gently over her abused arse.
“I… you… Yes”
“So you are now mine?” That got some real hesitation but it stop when Helen began to pull back the stick again.
“Yes! Yes I am yours! I am yours!” Alyssa begged
“Good slut” Helen said as a truly evil smile spread across her face “Now the real fun can begin”
In the normal world that won’t have meant but in the gangs Alyssa had just become Helen’s pet, and while rape was looked down on Helen could now do anything to her. She grabbed the waist band of Alyssa paints and pulled them down, the cotton sticking for a second were it had been forced up between her legs. She left them around her ankles and moved back up to examine the pretty little pussy she had revealed, the little pink slit with a light covering of blonde hair. Helen began to move her fingers over Alyssa’s outer lips, Alyssa body gave an involuntary shiver.
“Please stop” she sobbed
“We can stop anytime you want and I can go back to the stick. Would you like that slut?” Helen asked to which Alyssa shock her head rapidly. Helen went back to working the outside of Alyssa pussy, slowly, gently, almost lovingly, quietly building up the girl’s arousal and the glisten of moister. This continued until Helen slipped her fingers inside at which point her face twisted in disgusted. She moved her fingers out fast and grabbed hold of the flesh at the top of Alyssa cunt twisting it viscously forcing new squeals of pain from the girl.
“How the fuck did you lose you virginity slut, I know no lad around here has touch you, did you put yourself around back when you where someone, do you push shit into you to get off, or was it your dad we all know what they say about him? Come on now slut tell me” with that she gave another savage twist.
“I used to ride horses… one day… well it just happened” Alyssa cried back.
Helen let go throwing back her head to laugh “You mean you gave your cherry to a fucking horse, was it good? Did you cum? Did he call you after?” Helen mocked “Well slut I was hoping I could take it myself but at least this means I don’t have to go slow anymore, you going to love this horse fucker”
Helen walked over to her bag and emptied it onto the table, Alyssa eyes bulged as she took in the contents. From the small pile of toys Helen had brought to her party first she selected a long, thin, metal vibrator. She played with the black, plastic bottom experimentally bringing it up to full speed and then back down again. She placed the cold, hard tip above Alyssa clit and smile down at the exposed girl.
“I am going to make you cum, you should know this isn’t about make you feel good, this about the power I have over you slut, I am going to use you up and FORCE you to cum for me. Just so you know” and with that she twisted the black knob all the way up putting the small but powerful motor inside the toy on full. Alyssa body tensed at the new sensation and an unmistakeable moan of pure pleaser slipped passed her lips before she clapped her mouth closed. Helen moved her hand in small circular motions sliding her toy over the skin around Alyssa’s clit but always keeping the vibrator near her most sensitive spot. If this had been about Alyssa she wouldn’t have, there would have been more build up, it was clearly too sensitive as she desperately tried to move her body away. Uncomfortable or not it was clearly effective, to her credit Alyssa fought it but it was inevitable, it wasn’t long before her body betrayed her. Her checks where flushed, sweet ran down her face, each outward breath was a stifled moan and her body was pushing back trying to increase the pressure of the contacted.
Helen knew she had the girl close, knew just one more push would put her over the edge, and knowing this she pulled back. The noise Alyssa made was a growl of frustration which only made Helen smile at the power she had over her new play thing. She held off for a heart beat more and then pushed the toy back forwards. She wasn’t aiming for Alyssa clit anymore but the middle of her dripping cunt, she drove the vibrator as deep as she could the two fingers she gripped the base with disappearing inside the girl’s body. This sent Alyssa’s body into climax, her screams again filling the air but from a new reason, her muscle tensed so hard that her arms ripped free from Sam grip. But Helen didn’t just want an orgasm, she wanted a big one, she pumped the vibrator in and out of her spasming cunt at speed, her free hand moving in the rub her finger hard across Alyssa clit, sending new waves of pleasure through her body forcing it to stay at its peak for longer.
It had to end and Alyssa crashed back down onto the table breathing hard. Helen pulled back and ran her tongue up one side of the toy tasting the girl’s juices. She walked around the table slowly swapping places with Sam. Alyssa body was near spent and was trying to doze off, Helen put a stop to that with a thunderous slap to the face “We are nowhere near don’t with you slut, now clean up after yourself”
With that she force the wet vibrator into the girl’s mouth making her taste herself, at first she gagged and tried to pull away but soon go the idea that she wouldn’t be allowed to before had done as she was told. It was half heart but she liked and sucked the toy clean of her own cum. All this was a side show however as Sam was now standing behind the girl. She lifted her skirt showing off her round fat arse rapped in a near none existent, blue, lace thong. She slipped the thong down her legs and being the only male in the room threw it in my general direction and picked up something else from the pile of toys.
It was a strap-on, a red rubber dildo longer and much thicker than the vibrator attached to a black leather harness. She slipped it up her legs to replace the thong and adjusted the straps to keep it in place. This coupled with the strong muscles that I knew lay just underneath Sam’s fat meant that Alyssa wouldn’t know what hit her. Even with the resent climax Alyssa was tight and it took some force to stuff the large dildo deep into her. New cries of pain, slightly distorted by the presents of the toy in her mouth, fill the room. Sam went hell of leather, one good thing about having sex with Sam was she always put in full effort, and even with the clear pain it was coursing Alyssa the physical stimulation could not be stopped and soon her body was responding again, moving in time with the downward thrusts.
It was then that Helen called a stop “Sam pull out now, I am in the mood for something else, fuck the sluts arse.” Sam pulled out and began to line up with Alyssa pucked little arse hole. Alyssa panicked.
“Please NO! NO! Not that! It is too big! It will kill me! Please!” Helen slapped her again to stop the rambling.
“You are mine now slut and you are going to be taking it up the arse a lot if I have anything to say about it. You are going to have to get use to cumming that way like a proper slut” and she nodded to Sam who thrust forward. If it was hard to penetrate Alyssa’s cunt her arse was near imposable, Sam had to pull out to re-lube from the juices of Alyssa’s juices again and again each time forcing her way deeper into the girl’s tight arse and getting more cries and sobs to stop. I got punishment but I am no sadist, if it had just been us there I think I would have stopped it but with the number of gang girl there watching I didn’t, my reputation was everything and I would lose face.
It took a long time but in the end Sam got all the way in, she pull back and did it again and again. Soon it became easier and Sam put herself into a steady rhythm pounding the girl’s arse. It felt like an age but it couldn’t have been all that long as Alyssa whimpers of pain began to take on a new edge, much to my surprise the new sound could only be described as a whine of something close to pleasure. There was still a lot of pain mixed in but soon there was no mistaking it, some part of Alyssa was liking it and it kept building and building.
When the orgasm came it was a sudden, brutal and dirty thing forcing it’s way though Alyssa shaking, abused body, the noise she was making as much sob of shame and moans of ecstasy. Sam wasn’t done, the violation of the girl’s body had turned her on. She undid the harness leaving the dildo sticking out of Alyssa arse and flipped her onto her back. Sam climbed onto the table and straggled Alyssa’s face forcing her cunt onto her mouth. It wouldn’t be right to say she made Alyssa eat her cunt, Alyssa had very little to do with it, brutalised and half stunned from what had happened to her she just lay there and took it as Sam fucked her face.
Sam picked up pace riding the girl’s face, head thrown back, eyes squeezed shut and she began to scream about how close she was, I learned forwards to watch the show. Another reason why it was fun to fuck Sam was that when she came she really came, Sam was a squirter. She raised her cunt a few inches of Alyssa face sending her fingers to work rubbing and slapping her clit. She gave out one last scream and came. She sent gush and gush of liquid into Alyssa face, filling her eyes nose and mouth with her cum as her body tensed on top as Sam hit her climax. Sam role off leave Alyssa sputtering and gasping for breath, her face, chest and hair soaked though. Her shirt clung to her body near see though from the liquid. She role on to her side and did the best to roll into a ball.
“You are mine now slut,” Helen said “body, mind, and soul. You ever question that and we can do this again and again and again. You are dirty and I will use you for my pleasure and the pleasure of the gang but if you are a good slut I my make you come now and then and I won’t hurt you when it isn’t fun. We can go over the rule tomorrow.”
With that Helen left the girl quietly crying and walked out, the rest of the girls following her.
“Make sure she makes it home, we could do without her being found like this” I said to Lexi and walked out. Two cleaner stood outside, they would have heard most of it, but they where estate people they knew not to fuck with the gang. I slipped the both a £10 note and told them to wait until the room was empty and clean it. I knew they would do a god job, everyone has a prices it just worries me how little some people is. I walked out, I still had a corner to get too and tomorrow to look forward to.

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The second encounter