Sexual orientation :
Schoolgirl and Headmaster
This is a story i wrote with the help of a married woman I was sleeping with. We used to while away the hours that her husband was at work by making up these stories. Unfortunately I have lost the rest of this one and will not be finishing it as I'm no longer in contact with the woman in question. Please enjoy what there is though.
This semester had started out very differently for Abbey. Always the slim, androgynous gymnast, she’d never had the figure to attract the boys attention. But that had all changed. Over the holidays, she’d blossomed into a gorgeous creature of siren stature, her figure going from boyish to hourglass seemingly overnight, her breasts swelling to a full DD cup, her ass a firm, rounded masterpiece. Coupled with her long brown hair and stunning blue eyes, she could stop a grown man in his tracks. Unfortunately, it was these sudden changes that bought about the Teacher sending her to Sir’s office.
Abbey hadn’t had time to buy to new uniforms before school started, and all of her uniforms were too small. Her skirt was so short it came up to the crease where her slim things met her ass, her white blouse so tight she had to undo the first three buttons so her breasts would fit. When she arrived for class, Teacher declared her uniform was inappropriate, and in spite of her protestations, Teacher called her a “shameless hussy” and send her to Sir’s office to be punished.
Sir had Abbey sent straight into his office when she arrived. She stood before him, hunched over, looking at her shoes while her reviewed her academic record. He was surprised by her good grades – usually tramps dressed like her didn’t bother with classes, instead just chasing the boys. He knew this one was different; she didn’t have the confidence of the usual jail bait he had dragged into his office. Sir told her to stand up straight and push her shoulders back; he wanted to have a good look at this girl. He walked around her, surveying her, his eyes skimming across the thrust of her breasts, the swell of her ass and hips, and imagined the sweet pussy he knew was under that far too short skirt. Unfortunately for his already hardening cock, her breasts were already straining against her shirt and when she straightened up, another button popped, revealing a glimpse of white lace and creamy skin.
Sir was much younger than Abbey imagined. He was tall, much taller than her, lean and muscular. She wondered to herself if what the cheerleaders had said was true, the taller the man, the bigger his cock. Abbey wondered with awe just how big his penis might be.
“Well, what do you think Miss? Do you think you should be punished for wearing so little to school?”
Abbey was shocked. Surely he didn’t think it was her fault? She tried to reply but took too long.
“Bend over. I think you know how slutty that outfit looks and you’re going to pay for it.”
Whack! Abbey felt the sting of the cane across the back of her legs. Tears sprang to her eyes as she tried to beg for mercy. Whack! Another sting, this time higher.
“Please Sir, I’ll do anything, please don’t hit me again,” she sobbed.
“Anything?” Sir asked, a mysterious glint in his eyes.
“Yes Sir, anything. Anything at all.”
Sir pondered her offer for a little while longer, wondering how he get the most out of this sweet, innocent, probably virgin, schoolgirl. He told her to stay where she was and think about her circumstances. He rang the Secretary and told her to clear his afternoon schedule, that Abbey’s discipline was going to take longer than he anticipated. His cock was rock hard from the caning, he loved to see welts on a woman, to have her submit and beg for mercy. He was going to train this girl, and when he was done, she would do anything, absolutely anything, to please her master.
Sir sat down at his desk, readjusting his massive tool in his trousers, seeing Abbey’s eyes widen when she saw just how big he was. She was interested, and now he had to see how far he could start to push her.
“Abbey, I can see that your marks are excellent. You’re brilliant in Math and English, but I’ve noticed that your marks in physics are lacking. Can you explain this?”
“No Sir. Well, Teacher doesn’t like me Sir. She was the one who sent me to your office this morning. I get the right answers to all of my questions, but she marks me down for reasons I don’t understand.”
Sir pondered this. Possible leverage perhaps? He had made up his mind though; this process will take quite some time.
“Abbey, I want you to go back to class. You will not be punished for your uniforms again. They are satisfactory, you will not change them. If I find out that you have, you will be punished again. Now consider this a warning. If I find you in my office again, for any reason, you will have to make good on your word to do anything for me. Understood?”
Abbey nodded. Sir nodded his head for her to leave, and she slowly left his office. All she could think about his massive cock and how she could get a good look at it.
Abbey couldn’t sleep. All she could think about what Sir’s giant cock. It had to be at least 10 inches, even though the cheerleaders in the locker room said penises didn’t grow that big. She reached down between her legs and felt for her love button, circling the little pink nubbin of flesh with her finger, drawing the juices up from her pussy. Her clitoris was so sensitive, her pussy wet, just from thinking about Sir. She kept thinking about that cock. She’d only ever seen one in real life – one of her boyfriends tried to get her to suck on his, but she said no, and he dumped her. He had such a little pecker by comparison. She started to pinch her nipples, slowly pulling them away from her breasts, stretching them out, arching her body as her fingers kept working on her clit. How would it feel to have that massive tool in her pussy? Filling her up, would it hurt her, or make her cry out? She slowly inserted two fingers into her dripping pussy, thumbing her clit as she got more and more excited. She imagined herself spreading herself wide on Sir’s big desk while he fingered her pussy to get her ready for his manhood. She wanted to feel something in her pussy – she’d never had anything other than her fingers in there before. She imagined taking his giant cock in her cunt, stretching her, filling her, covering her titties with his cum. and started to writhe in orgasm bucking her hips off the bed, her fingers plowing in and out of her pussy, little cries of pleasure escaping her lips. She’d never cum that much before, her juices pooling on the bed. Tomorrow, she would be sent to Sir’s office. Tomorrow, she’d be a very, very naughty girl.
Abbey dressed in her shortest skirt, looking through her wardrobe for the right shirt. Finally, she settled on a tight short blouse that was almost transparent, and left a little of her belly bare. She knew this get up would cause Teacher to send her to Sir’s office. She artfully applied her makeup, making her blue eyes bigger and more alluring. She put her long hair into piggy tails, just like a little girls, and then put on her knee high socks and Mary Jane shoes. Both her parents had already left for work when she left the house. Abbey made sure that her lacey white bra was visible through her shirt before getting on the bus. The bus driver looked her up and down with pure lust in his eyes, forgetting to take her money. In this outfit, she could get away with anything.
She had to sit through two periods of classes before Physics, and spent the whole morning making sure that every boy in the class who’d ever dumped her knew just what he was missing out on. She was a little surprised when one of the boys grabbed her ass; he was even more surprised to find she was only wearing a tiny white g-string under her short tartan skirt.
As soon as the door opened to go into the Physics room, Teacher stared right at Abbey. Now she knew why Teacher had been giving her a hard time – she was jealous of her little teenage body now she’d gained her womanly curves. Teacher didn’t even say a word, just pointed down the corridor towards the Head Master’s office, and with a smirk, Abbey sashayed down the corridor, flaunting her tight body and gorgeous ass for all to see.
The Secretary was surprised to find Abbey back at the Head Master’s office for the second day in a row. She knew that Abbey had spent quite a bit of time in there yesterday afternoon, the welts on the back of her legs showed that she had been punished. She wondered why the girl would bring such misery on herself. She shook her head and told Sir that Abbey had been reprimanded yet again.
Sir was delighted to hear Abbey was back. All his plans were falling into place. Ever since he had seen her at gymnastics practice last semester, he had lusted over that tight little body. Now that she’d filled out, that yearning increased tenfold. He called her into his office, expecting that quiet little girl he’d met the day before. What he got however was a brazen little Lolita slut who looked like she was just begging for a good fuck.
Abbey noticed the surprised look on Sir’s face. Maybe she’d got it all wrong? Maybe he didn’t want her after all? She considered what she was wearing and thought she’d made a total fool of herself, thinking that a grown man might want a little girl like her.
“You’ve changed your uniform Abbey, what have you got to say for yourself?”
“I thought you’d like it Sir, I do so want to please you.”
“Well Abbey, I do like it, but that’s not the point. You’ve gone far beyond the uniform requirements. I’m very, very disappointed with you. I’ll have to punish you again Abbey, there’s no avoiding it.”
She looked at her feet and scuffed her shoe on the hardwood floor. Looking back at him through her long lashes, biting her trembling lip she asked “Are you sure there’s nothing I can do for you Sir? I don’t want to be canes again.”
That did it; it pushed him over the edge. He wanted this girl and he wanted her now. His cock was straining against his pants, his pre-cum soaking his boxers as a low groan issued from deep in his throat. His restless dreaming of this little vixen was giving way to the reality that stood before him. He moved his chair back from his desk, and asked her to come closer to him.
“Alright then, you said you would do anything, and now you’re going to do exactly what I tell you. If you say no, if you hesitate or stop, I will whip you. Understood?”
“Yes Sir.” Abbey quietly replied. She was scared. What was he going to do? Would he hurt her? In spite of her hesitation, she was already wet. The thought of seeing his cock, touching him, made her quiver with anticipation.
“Get down on your knees. Take off your shirt.” Obediently, she slowly sinks to her knees, wide eyed and trembling with excitement unbuttons her shirt.
“Have you ever seen a man’s cock before Abbey?”
“No Sir, only a boy’s.” She replied, looking up at him with her big blue eyes.
“Have you ever touched a man’s cock before Abbey?”
“No Sir, never,” she shook her head.
“Well today, you’re going to learn some valuable lessons.”
Abbey was kneeling behind Sir’s desk; she could feel her pussy juices coating the insides of her thighs. Sir slowly unzipped his trousers, exposing his dark silk boxers. She could see the wet stain on them and wondered if he leaked like she did when he was excited. He lowered his boxers, and sat back in his chair, watching her face as he did so. Abbey was astonished. There was no way Sir was only 10 inches, it was larger than that even, closer if not larger than 12. She started to get worried. It was so long and thick she might not be able to fit all of him in her tiny pussy. Little did she know however, that was not what he had planned for her this afternoon.
“I’m going to teach you a lesson today Abbey, one you’re never going to forget” He gestures for her to come forward, and she shuffles towards him on her knees. Abbey can see his cock jerk at her submissiveness, unaware on just how much this is turning him on. She can see the pre-cum leaking for the tip of his cock, imagining what it will taste like, wondering if she can get his head in her mouth, let alone the rest of his length.
“Now Abbey, I want to you gently take my cock in your hands and suck on it. Take my head in your mouth and run your tongue over my head and lick up all that pre-cum. That’s a good girl.” Slowly, looking up at him with the big innocent eyes, she licks him, she likes the taste. She gently caresses the head of his cock with her soft lips. She cups his balls with her small hand, but he slaps her with a riding crop for acting out of line.
“You will only do what I tell you, when I tell you. Otherwise you will be punished. Now take off your panties, I want to see how much you’re enjoying this.”
She removes her little white panties. They’re so soaked they’re transparent. He smells them, and drops them on his desk while she continues to lick his cock. Sir tells her to take his head in her mouth. She tries, accidently scraping her teeth of his head. He slaps her again, she must be more careful if she doesn’t want to be caned. She sucks gently; trying to keep her lips over her teeth, trying not to scrape him again. He nods his head and tells her she’s doing a good job, and now she can cup his balls and massage them gently. She takes more of his cock in her mouth, a little below his head and continues to bob up and down. Sir grasps her piggy tails and guides her head, treasuring the sensation of her warm wet mouth trailing up and down his cock. Suddenly, he thrusts into her throat. She chokes, she tries to pull back but can’t – his grip on her hair is too strong. She’s forced to keep sucking, slowly slurping her way up and down his cock, feeling him swell under her lips. She gently massages his balls, feeling the soft skin covering them. Sir keeps thrusting into her face, getting deeper and deeper into her throat. He’ll teach her how to suck cock just the way he likes – so far, she was doing just fine. She starts to flick the underside of Sir’s head with her tongue, and then takes even more of his length down her throat; sucking, sucking, he can feel her tongue as she works her way up and down his cock. Sir pulls out of her mouth, standing up, his cock bobbing in front of her eyes, he tells her what to do next.
“Get up Abbey; I want to see how tight your pussy is.” Abbey obediently stands up wondering why he stopped her sucking his cock, and Sir turns her around, flicks her skirt up and pushes her against his desk, face down. Sir grabs her hips and slams his cock deep into her pussy. Abbey cries out in pain, she’s never let a boy in her pussy before, and now Sir is plowing into her with his huge cock. The more Abbey cries out, the harder Sir slams into her.
“Are you a virgin Abbey? Have you ever had a cock in your tight little snatch before Abbey?. How does it feel to have this massive tool forcing you open Abbey? This will teach you to be such a slut, flashing the bus driver and letting the boy’s touch you” he grunts as he thrusts into her with more force.”
Sir grabs the crop again, leans back and whips her across her bare ass, leaving a giant red welt. She cries out again, but notices how the sting of the pain makes her even more excited. Sir feels her pussy contract around his cock and asks “you like that do you, you little girl slut. You like the feel of the lash across your ass do you?” Abbey moans, and Sir can feel her juices leaking out of her tight pussy and out around his cock. Sir catches her juices with his fingers and gently explores her nether hole.
Abbey jumps, thrusting back onto Sir’s cock. No one’s ever touched her there before. Sir tells her to relax and that she’ll enjoy it. Slowly, he circles her asshole, making sure she’s well lubricated; he can feel her relaxing as he continues to pound his cock into her cunt. He slows down his thrusts as he slowly puts more pressure on her asshole. Abbey doesn’t know what to do, but is too scared to say anything. Then suddenly, she feels his finger push into her ass. She feels full, fuller than she’s felt before. His cock in her pussy and his finger in her ass is more than she can stand. She starts to cum as he thrusts into both of her holes. Her pussy spasming around his cock, Sir can’t last much longer. He pulls out of her and commands her to get on her knees.
“But Sir, I want you to cum in my pussy.” He whips her ass again. “I told you, you obey every word I say. Now get on your knees!” He forces her down on her knees, holding her head as he forces his cock down her throat. She chokes slightly but manages to get more of his tool into her mouth. Bobbing up and down while he holds her head, Abbey fingers her own pussy to another orgasm while she sucks on Sir’s cock. It’s too much, the sucking, her tight little body, watching the little slut finger herself while he fucks her mouth - he’s going to cum in her mouth. He considers pulling out to cum on her tits but decides against it. He holds her head more firmly as she feels his balls start to jerk, she doesn’t know what a wonderful present she’s about to get. His cum shoots up from his balls, up his shaft into her mouth. She gags, trying to swallow the white, salty fluid. It starts to leak out of her mouth, down her breasts. She swallows as much as she can as he finishes pumping into her mouth.
“That was good Abbey, but you’ll need lots of practice.” He says as he pulls his softening cock out of her mouth. She nods at him, wondering what to do next. He scoops of some of the spilt cum from her breasts, before it soaks into her bra, and tastes it. “Did it taste good Abbey, do you like it? Did you enjoy my cock in your virgin cunt? Did you like my finger in you tight little asshole?” She nods again. “You can clean the rest of that off your breasts now Abbey, I don’t want to see a single drop wasted.” She uses her fingers to clean up the globs of salty semen from her breasts, sucking her fingers clean.
“You can get dressed and go now Abbey. I’ve given you your lesson for today. If you get into trouble again, you’ll be punished again. You know that, don’t you Abbey.”
Gingerly she stands up, feeling used, and sore and torn from where he slammed his cock into her pussy without warning, but still yearning for more. She starts to button her shirt back on.
“Yes Sir. I’ll try to be a good girl” she says, giving him a playful smile. Sir knows she won’t, and looks forward to her next lesson.
It was then that Sir noticed the panties that were still on his desk. He smells them, sucking Abbey’s juices from the crotch. He then drops them into the drawer where his crop lives and savors the memories of violating the young girl who owns them.
Abbey was surprised to find herself called back to Sir’s office. She was worried when she heard the announcement over the loud speaker, as this time she hadn’t done anything to get his attention. When she arrived at his office, the Secretary told her to go straight on in.
“You’re late.” Whack! The riding crop slashed against the back of her legs as Abbey cried out in shock. “What took you so long?” Whack! A second cut, then a third. Abbey was too shocked to reply, wondering what bought on this sudden attack. Whack! “You were caught flashing the boys at gym class this morning – Coach told me all about it. How you were fingering your wet little slit to drive them wild.” Whack! The crop bit into her soft flesh again. Abbey was horrified. Surely Sir hadn’t found out. She was so hot watching the boys she just had to play with her snatch, but didn’t think anyone had seen her. She stood shaking her head in denial of the accusation as he drew the riding crop up under her skirt, tracing the crack of her ass with its tip.
“Are you denying it you little slut? You know you’re not allowed to share your little cunt with anyone but me. For that, I'm not going to spend as long opening your ass up before fucking it.”
“Oh sir, please!” Abbey begged, she wasn’t ready for his massive tool up her ass yet, she could barely handle the width of his fingers back there.
Sir considered her tiny little asshole and relented, “I'll open it up a bit for you but it's still going to hurt when my cock slams in” She started to sob, apologising for being late. “I was going to work you up to three fingers and then ease my cock into you, now it's only going to be two fingers and I'm going to shove it in rough.”
“Oh sir, you'll hurt me. I would have come sooner but Teacher wouldn’t let me out of class.” Abbey sobbed, still feeling the sting of the crop against her legs. “It wasn’t my fault!”
Sir looked at her dismissively. “It will only hurt for a little bit. It’s less than you deserve for disobeying me, let alone lying. You disobeyed me, and you will be punished. Abbey tearfully nodded her head. Sir didn’t like to punish her unnecessarily, but the girl needed to learn to obey. He reached under her skirt and was surprised to find she wasn’t wearing panties, and that she was already sopping wet.
“Have you been playing with your pussy between classes again Abbey? You know that’s not allowed” he asked as he roughly shoved his fingers into her cunt. Abbey shook her head, but couldn’t concentrate with his fingers strumming her clit and plunging into her pussy. “At least your pussy is nice and wet so I have plenty of lube for your ass.”
Abbey trembled. She couldn’t help it, every time she walked past his office, or saw him, she started to leak. Her pussy was constantly juicy and it drove her wild not to touch it at every opportunity. She apologised for the wet state of her cunt.
“You don’t get in trouble for being wet Abbey, in fact that only helps me lube up my cock for your tight ass. I want you as wet as you can be. Are you ready for your lesson now Abbey?” Abbey nodded. She was still scared, it hurt her so much for him to fuck her pussy, and that was supposed to have cocks in it. But her ass? She wasn’t sure, but knew if she hesitated it would be much worse for her. Sir slid two of his fingers into her sopping pussy, relaxing her, lubricating them ready to plunge into her virgin ass. She feels a familiar pressure as he slides one long finger into her ass, slowly moving it in and out of her tight hole. He releases his rock hard cock from his pants, letting it bob in front of him ready for action. He slides a second finger into her ass, pushing them as deep as they’ll go, opening them up, stretching Abbey’s tight little hole more and more with each thrust. Abbey is relaxing. She loves the feel of his fingers in her asshole almost as much as she loves his cock in her pussy. She begs for more as he suddenly slams his cock into her sopping pussy all the way in, forcing it in and out, coating it with her cum, lubricating it ready to plunder her virgin ass. He pulls out of her, leaving her pussy aching for more, and with one quick thrust, forces his way into her tender hole. Abbey screams in pain, it’s too much, it hurts, she begs him to take it out. He rubs her clit, telling her to relax, that it’s ok, that she will enjoy it. Each time she tries to pull away from his invading monster, he pulls her back, thrusting deeper and deeper into her bowels. Slowly, the pain turns to pleasure. His fingers dancing over her clit and the feeling of fullness in her ass are overriding the pain of being penetrated. Abbey starts to moan, sliding back and forth on his cock on her own, wanting more and more of his length to fill her, to make her cum.
Sir decides she’s enjoying her punishment too much. Pulling out of her ass with a wet pop, he lies down on the couch in his office and commands her to come to him. He positions her with her ass above his cock, but instead of letting her descend slowly, jerks her ankles out and causes her to fall hard, slamming his cock past her sphincter. She screams in pain at the painful penetration. She cries again and again how much it hurts as he moves his hips, thrusting into her ass.
“You're being taught a lesson Abbey. You must learn in life there is no gentleness, and you will experience pain if you don’t obey immediately when you are told to do something.” Abbey nods, starting to enjoy the sensation again. Slowly she starts to grind her hips into his, grinding her ass into his cock. She wants more. She asks if she can touch her pussy.
“No Abbey, today is a lesson for your ass. You are not allowed to touch you pussy.” Abbey dutifully agrees, remembering that she can still touch herself when she gets home, which is all she seemed to do anymore. She moves faster on Sir’s cock, bouncing up and down, more and more of his tool coming into view before she slams down on it again. Suddenly she rises too high, Sir’s head popping out of her ass. Feeling empty Abbey quickly drops back down, slamming his cock into her ass. She screams at the sudden pain, but does it again, and again, loving the pain as she purposely violates her own ass. She’s begging to cum, begging for Sir to cum in her ass. She wants to feel his cum dripping out of her nether hole, to feel it run down her legs and mix with her pussy juices. Sir slows his thrusting for a moment as Abbey continues to grind into him.
“Abbey, if I cum in your ass, you will still have to clean it up and eat it.” She hesitated. “Oh Sir, that is so dirty.”
“But you’re my dirty, dirty little slut Abbey.” She agrees, she is his dirty little slut. But still, it seemed a bit too much for her just yet.
“Do you want me to cum in your ass, or in your mouth Abbey?” Sir asks, giving her a way out.
She decides. “Cum in my mouth Sir, then I can’t miss a drop.” He nods and motions for her to get off his cock. As she climbs off, she can feel his massive cock slide from her stretched asshole, and feel his head pop from her sphincter. Kneeling in front of Sir, Abbey reaches out with her tongue to taste the meat that was so recently plundering her back passage. It tasted different from her pussy, but she still engulfed his head with her mouth and started to suck with that little bow-like mouth that got him so hot to watch. He can’t wait; he shoves his cock hard into her mouth, cumming hard, cumming down her throat. Abbey swallows as quickly as she can, not wanting to waste any of the precious load she was receiving. Finally as the flow slows, she licks his cock clean, making sure she gets every drop of cum off his manhood.
She licks her lips and looks up at him with the big innocent blue eyes. “Sir I want more. I want to taste your cum again and again and again. I want to taste my pussy juice on your cock.” She stopped to think for a moment. “Maybe one day Sir, when you punish one of the other girls I could watch you take her and clean your cock up after, just to see what other girls taste like.”
“Would you like to learn how to punish and whip someone Abbey?” he asked. His little nymph was learning quickly.
“Yes Sir, I’d like that very much. I need to know how to defend myself, especially now the boys are teasing me and touching me when I don’t want them too.”
Sir considered the idea. There were some students that did need punishment, and that would be a very special surprise for his best student. But he also had other plans for her that may take a little while to organise. For those he needed someone completely compliant. Definitely not one of the students, but he had the perfect woman in mind for Abbey to learn from. He’d make this little nymph love everything from cock to carpet munching. He just needed to find a better place than here.
“I think you should come to my house for some private lessons Abbey. Your physics grades are slipping too far. It’s not good enough.”
Abbey was puzzled by the sudden change of topic, but considered the change of venue. She nodded her agreement, thinking how much more they could at Sir’s house. She couldn’t wait. Sir told her to get dressed, and be careful with her ass, as it would be sore for quite some time. He gave her a sick pass to go home, so she wouldn’t have to sit through the rest of the afternoon in pain. As he watched her go, he grew hard again thinking about what he was planning for her little surprise.
Abbey was wearing her short slutty Lolita outfit again, the one with the skirt short enough to see her ass, and her tiny little white g-string. She must have a few of them, Sir pondered; remembering the one still has in his draw.
“Why are you here again Abbey? I didn’t send for you this time.”
“No Sir, teacher sent me again because of my uniform Sir. I wanted to see you again Sir. This outfit guarantees a visit to your office. I love your lessons so much I can’t wait to see you again.”
Sir is surprised by her response. His little slut was addicted. “And just how do you think I should punish you this time Abbey?”
“Sir, my ass is still gaping from the lesson you gave me yesterday Sir. Could we teach my pussy a lesson today please? I still feel the need for your great big cock in my pussy Sir; it felt so good the first time.”
Sir thinks about her request. He was very harsh on her yesterday for flashing the boys. But she did deserve it. She needed to understand that she was his property and his property alone. He was still considering the surprise he had for her too, and now was a good time. He called the Secretary and told her to have his next appointment ready.
“Abbey, I have a surprise for you a little later. But right now, you’re going to suck my cock. Now get on your knees and take it out. Suck on it you little bitch.” Abbey obeys immediately; knowing what happens if she doesn’t do what she’s told right away. She takes Sir’s cock out of his pants, and dutifully kneels down in front of him, taking his length into her mouth. She’s gotten much better since her first lesson. The vision of the little nymph sucking on his cock gets Sir rock hard in no time. “Stand up Abbey.” As she obeys, Sir slides her g-string out of her tight ass crack and down her legs. He picks her up and sits her on his desk unbuttoning her shirt and taking off her bra before kneeling in front of her. Abbey can’t believe it, Sir is going to kiss her pussy, and suck her clit. She gushes juices at the thought. Sir spreads her legs wide; satisfied to find she is already dripping wet. He buries his face in her pussy as she leans back, he licks at her pussy, sucks on her clit, making her gush again as he bites gently on her little pink nubbin. Abbey cums hard, flooding all over his desk. Sir laps at her pussy, drinking in her juices, making her cum again and again, making her legs tremble with pleasure. Once he judges her wet enough, Sir stands up to kiss Abbey deeply, sharing her juices with her, like she shared his juices with him. Sir rubs his cock up and down Abbey’s cunt as she trembles with the pleasure of it all, soaking his cock with her juices before pushing it deep into her wet pussy. Abbey moans in delight as inch by inch of Sir’s cock slides into her. Sir begins to bite her neck and breasts, leaving little bruises as he plows into her. Her pussy is spasming and her legs growing weak as she has orgasm after orgasm. He wraps her legs around his waist as she keeps cumming. Sir slows down his strokes to let Abbey come down from her orgasm, gently nipping at her neck, sucking on her nipples, letting her relax.
“Abbey, are you ready for the surprise I promised you?” She looks up and him with her gorgeous blue eyes and simply nods. Sliding out of her slowly, he tucks his cock back into his pants and goes to open the door. Standing there is one of the boys who keeps molesting Abbey. Sir drags him inside, slamming the door behind them. Sir strips off the boys pants, and asks Abbey if she still wanted to learn how to spank properly.
Sir grabs the Boy by the scruff, shoving him forwards towards the desk. Boy doesn’t know what’s happening, and is too stunned to ask. Sir bends him forwards and pulls out the riding crop he keeps in his top drawer and hands it to Abbey as she hops down from his desk.
“Boy, this is the punishment you get for touching my favourite student. How many times have you been told not to touch the girls without their permission? Abbey, you can start now.” Abbey whips Boy hard across the ass with the crop, leaving a finger thick welt of red skin across the width. Boy whimpers and tries not to call out. Abbey strikes him again, right below the last mark, and Boy cries out. Sir tells him he’d better get used to the pain, as this was only the beginning. Abbey whips him hard again, the welts not quite breaking the skin. Sir instructs her to do it again, and again, and again. The skin starts to break, Boy starts to cry as the pain becomes too much. Abbey keeps going and the sight of her naked body, breasts jigging with each stroke, and the bare whipped ass of the whimpering boy gets Sir so excited, he’s as hard as a rock again. Sir grabs Boy’s head and tells him to open his mouth; boy is confused, but opens his mouth to cry out as Abbey strikes him again. Sir grabs Boy’s face and shoves his cock down Boy’s throat. Boy chokes and cries even more as Sir shoves his cock in and out of Boy’s mouth. Sir can see the bulge in Boy’s throat as he rams his massive tool in again and again. Abbey is fascinated by the ravaging of the Boy, and Sir can see juices sliding down her thighs as she watches the scene before her. Boy is commanded to stay where he is, Sir giving his throat one last thrust before pulling out. He ties the boy by the wrists to the rail near his desk. Sir makes his way over behind Abbey and slams his cock into her juicy wet cunt from behind.
“Now Abbey,” Sir groans as his massive tool grinds into her soft folds, “We’re going to teach the Boy to never, never touch another woman again without permission.”
Sir can feel Abbey’s excitement as her pussy contracts around his cock; he can feel her juices sliding down his balls as he continues to grind his cock into her. One hand around her waist to keep his thrusts centred, he tells Abbey to turn the crop around, to hold out the thick rigid handle towards Boy. Sir whispers in her ear “Shove it up his ass. Make him hurt like you did when I raped your ass.” Abbey moans in anticipation, more of her juices lubricating the join between the schoolgirl and the headmaster. She lines up the crop handle with Boys ass and shoves it towards his hole. At first nothing happens but then slowly his ass opens up to accept the intrusion. Abbey is not gentle about it and as soon as his ass starts to accept the handle she rams it all in as deep as it will go. He cries out in pain again as she begins to fuck him with the handle of the crop. She moans at the sight of blood leaking from his abused asshole from where the thick crop handle has torn his delicate skin – it’s no less than the little pervert deserves. As she shoves the crop in and out of his ass, Abbey notices with anger that the little prick has a raging erection.
“Do you like being fucked in the ass little Boy?”She demands. “You like having a thick tool shoved up your dirty little hole?” Boy shakes his head, not wanting to be punished any more. Abbey roughly grabs his cock with one hand, pulling it with force, “Then what’s this you little pervert? Sir, I think the Boy likes to have his ass full.”
With a quick motion, Abbey removes the crop from his ass and the cock from her pussy. To his horror, Boy realises that the crop was just the start as she lines up Sir’s cock with Boy torn and abused asshole. Sir shoves his cock in as deep as it will go, making Boy scream again and again as Sir’s massive tool tears into Boy’s ass over and over. More blood drips from Boy’s ass as Sir plunges in and out of his nether hole. Boy can’t help it; his cock starts to drip pre-cum as his prostate is massaged constantly from the pounding in his ass. Abbey laughs wickedly, wiping up the sticky fluid from his cock, parading it in front of his eyes. “See, you do like it you filthy little Boy.” Abbey lifts her fingers to her mouth to taste the sweet juices from this perverted Boy.
Abbey looks up at Sir with her baby blue eyes and asks if he will pull out so she can see if Boy is stretched wide enough yet. Sir is happy to comply, not wanting to waste precious his cum in Boy’s worthless ass.
After looking at his gaping hole Abbey decides it's not quite wide enough yet, wanted to punish Boy more and more. She gently rubs her hand through her pussy lips, gathering up her own juices to lubricate her hand, fiddling with her clit in the process, moaning with the combined pleasure of her ministrations and watching Boy’s humiliation. Suddenly, she rams her fingers into Boys torn asshole, tearing them back and forth. First one, then two, soon she have all four in plus most of her thumb. Sir can't help himself and stoops to suck Boys cock to get a taste of his pre-cum for himself. For such a little Boy he is producing a lot of pre-cum. Abbey’s hand is not quite fitting in his ass so she asks for Sir’s help. Sir gently runs his hand through Abbey’s pussy, deftly fingering her juicy hole, gathering up her juices just like she had done before violating Boy. He removes Abbey’s small hand from Boys asshole, Boy screaming as Sir shoves his own massive hand into the stretched hole. Sir shoves as hard as he can, but can only get up to the start of his thumb in. Abbey kneels to suck Sir’s cock while still getting the perfect view of the violation. Sir starts to pound Boy’s ass with more and more force each push, getting a little more of his huge hand into Boy’s sorry ass with each thrust. Sir gently removes Abbey from his cock, not wanting to cum too quickly, and tells her to go suck Boy’s cock. She looks disgruntled, but he assures her it is just to relax Boy’s sphincter, and that Boy will not cum due to the pain radiating from his battered asshole. Abbey obeys, taking Boy’s little pecker in her mouth. Not much of a challenge after fighting to swallow Sir’s massive meat, she deftly cleans up the dribbles of pre-cum while wondering if her efforts are having the desired result. She can see in Boy’s eyes the relief the pleasure her mouth was creating to help reduce the pain radiating from his backside.
Sir could feel Boy’s ass loosening up after a few minutes of Abbey sucking Boy’s cock. He could feel his thumb knuckle beginning to enter his ass as his continued to push, but wanted Abbey to have the pleasure of violating him so fully for the first time.
“Get off your knees Abbey, come back here and I’ll show you a miracle.”
Abbey immediately obeyed, kneeling behind Boy, still juicing with anticipation. Sir pulls his hand out of Boy’s hole with a wet plop and positions Abbey’s fist at the gaping hole that was, until today, Boy’s virgin ass. “Ready Abbey?” he asks with almost loving adoration for his newest little recruit. She nods her assent and with Sir’s guiding hand on her elbow, quickly pushes her fisted hand into Boy’s hole with a distinct pop.
Pushing further and further in, Sir encourages her to go as deep as she can. Abbey tells Sir that boy a little dry, so Sir uses his hand to collect some of Boy’s pre-cum and use that as lube on his ass for Abbey’s arm. She pushes in past her wrist, half-way up her slim forearm, and then past her elbow but still she doesn't stop. Abbey shoves into his ass past her elbow while Boy screams and writhes with the pain of being violated so fully. At Sir’s urging, she begins to pump inside his ass with her arm, pulling out just past her elbow and then pushing back inside him. Sir grabs Abbey’s head and starts to fuck her mouth as Sir watches her fist disappear into this Boys pathetic ass. After a few minutes of deep fisting his ass Abbey can feel Boy begin to loosen again. She looks to Sir for encouragement and he nods for her to proceed with her other hand. She starts to slide in the fingers from her left hand; soon, all found fingers join her right arm in the violated hole of Boy, stretching it wider and wider with each moment. .
Both Sir and Abbey needed release from their pent up sexual energy, but neither would get satisfaction from this ruined male, his pecker too small to satisfy Abbey, his ass to stretched and torn to give Sir any pleasure. Sir tells Abbey to remove her arm from Boy’s ass – he has an idea. Even if his pecker wouldn’t satisfy her, his cum would. Sir and Abbey can see that Boy’s ass is no longer able to close at all – it gapes wide open, wide enough for them to see clearly deep into his bowels. Sir presses Abbey down in front of Boy, pressing Boy’s cock against her lips. She begins to suck as Sir pushes his fist back into that ruined hole, searching for Boy’s prostate. Unable to help himself, Boy cums from the sensations created from the massage of his prostate. He cums, shooting stream after stream of cum into Abbey’s mouth, though he gets no enjoyment from it because his ass hurts too much. Sir makes sure he’s deposited the entire load into Abbey’s waiting mouth before pulling his fisted hand out of Boy’s ass, tearing it further. Pulling Abbey up roughly, Sir kisses her deeply, savouring the taste of the sweet boy cum. Sir kicks Boy’s clothes to him and tells him to get dressed.
“You will go back to class now and think long and hard about what you’ve done. You’ll never touch a woman again without her permission, and if you do, I will punish you more than I have today. If you tell anyone about your punishment, I will make sure you live to regret ever touching a girl against her will.”
Still crying and whimpering, Boy tries to put on his pants while not to touch his once pristine but now ruined ass. Sir and Abbey watch as he feels himself and he realises just how badly they destroyed his ass. His ass checks were red and covered in welts from the flogging Abbey had administered - it would be weeks before he’d be able to sit again comfortably. On the other hand, his hole was still trickling blood and gaped so wide it probably wouldn’t close for a week.
Watching Boy leave, Sir manoeuvred Abbey behind his desk so he could enter her from behind. Abbey moans loudly and releases the orgasm she’s had building all afternoon. Then she asks something that stuns sir completely.
“Sir,” she asks breathlessly, “I want you to fuck me in the ass while I pleasure myself with the riding crop I violated Boy with.”
Sir groans in anticipation and sinks his cum soaked cock into her waiting ass. Abbey reaches between her legs and shoves the handle of the crop into her yearning pussy, pulling it back and forth across her sensitive g spot. Sir can feel the bumps of the crop through her vaginal wall, giving his cock extra sensation. He won’t be able to hold off cumming for long. She fucks herself madly with the crop, faster and faster, her actions causing her ass and pussy to spasm as she has wilder orgasms than Sir had ever witnessed before, cumming uncontrollably. Sir can’t stand it any longer and with one final thrust, shoves his massive cock deep into her ass and cums harder than he has ever cum before. He can feel it splash against her bowel walls and start to leak out of her ass around his cock. He pumps stream after stream of thick sticky cum deep inside her. Finally, spent, he pulls his cock out of Abbey’s beautiful ass to view his work. She’s still pounding her pussy madly with the crop, only aware that the wonderful fullness from her ass was gone as Sir kneels to view his handiwork. Sir can’t help himself and leans in to lick the cum from Abbey’s ass as it trickles from her hole. Slowly he moves up her crack, gently flicking his tongue in and out of her hole, not leaving a single drop of cum behind. He locks his lips around her asshole and tells her to push, depositing another deposit of his own cum into his mouth. He slowly turns her around, giving the deposit back, tongues entwining around each others, savouring the taste of each other and Sir’s seen. Finally, Abbey collapses from all her orgasms, her legs giving out as Sir stoops to catch her as she falls. He slowly dresses her, savouring the sight of his young nymph, kissing her feet as he smooths her long white socks up her legs, fingering her sensitive pussy as he fastens her skirt, caressing her swollen breasts as he buttons her shirt. She looks up at him, completely satiated, her blue eyes tired, but glowing.
“It’s time to go back to class sweetheart.” Reluctantly, she nods, gingerly hopping down from his desk, aware of the puddle of girl-cum she left there. Sir kisses her gently on the forehead and tells her that if anyone, anyone at all, touched her again without her permission, that they’d teach them a lesson too, and the sends her on her way.