Inappropriate Conquests

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Story Notes:
Professor Bell is the first.

Hugo thinks it’s pointless that flying is an actual class, and he has no interest in actually devoting his time to doing something he had mastered by the time he was nine. He isn’t much older now, but Mum always tells him he’s mature beyond his years. There’s little doubt in his mind that she doesn’t mean it regarding his sexuality, yet it’s still an appropriate definition. And it’s not as if he doesn’t attempt to tolerate flying. It’s just a waste of time, especially when there are some students who can’t even get the broom to levitate even after four months of practice.

He’s twelve years old when he goes to Professor Bell to speak with her about receiving permission to spend his time in the library revising instead of attending class. It’s frustrating when she treats him like a child, even using small words as if his vocabulary doesn’t extend beyond two syllables. When he returns to the Slytherin dorms, he lies in bed seething and tries to imagine what Mum would do if she’d been told no and been treated in such a condescending way.

While Mum probably wouldn’t decide to use sex to gain an advantage, he knows that she’d do whatever it takes to achieve her goal. He’s read the book that Skeeter woman wrote, and he’s also heard stories from members of his own family about her stubborn determination to get her way. He takes after her, thank Merlin, because he loves his father, but he’d rather be cunning and focused than social and athletic.

Sex is the obvious solution to his problem, and Mum has told him before that people often ignore the obvious possibility and end up complicating things when they don’t need to be. Professor Bell is a single witch not much older than his mum who is stuck at the castle with no one to alleviate her urges. It’s a no brainer. While he’s never had sex before, he’s been reading about it since he first got hard two years ago. He’s able to come now, even if it’s still clear and not the grown up kind of come that Teddy’s talked about before. He’s confident that he can achieve his goal, and he doesn’t put a value on virginity, so it doesn’t matter to him to give that up for extra library time and less wasting his time.

The next day, he meets with her again. She’s hesitant, but he insists, and she doesn’t protest for very long when he’s got his face buried in her cunt. He doesn’t really find her attractive, but he’s still hard because she’s his professor and she’s sitting on her desk with her legs spread open. He uses his fingers when she tells him to, and he licks all over, but pays attention to the spots that cause her to make noises. He’s doing well, not that he’s too surprised by that. It isn’t Arithmancy to lick around and poke at her, after all.
He does wonder if she’s ever going to come, though, because his tongue is starting to get numb and his jaw hurts.

Professor Bell is moaning when Hugo adds another finger. He knows his hands are small, he’s only twelve, and it probably isn’t enough for her. Raising his head, he studies her a moment before he decides to put another finger inside. She is squeezing her tits and pushing down against him, and he can only think about how much trouble they’d be in if they got caught. That risk excites him, makes him reach down to rub himself, and he soon as his entire fist inside her as she cries out for more.

Hugo gets a pass to skip Flying lessons for the rest of the term. He also gets personal lessons from Professor Bell on how to properly lick a woman to orgasm.

Professor Sinistra is his next target.

She’s much older than Professor Bell, which makes it more exciting, and she’s beautiful in a way he appreciates. It’s a challenge, and he spends the remainder of first year watching her and figuring out how to approach her when it’s time. By the time second year begins, he’s got his plan in mind, and it takes him two months for it to come to fruition. A request for extra coursework and a special assignment to watch a meteor shower results in her on her knees and his tongue in her arse. Hugo is surprised at how much she enjoys him playing with her arse, which is something Professor Bell never wanted.

The stone is cool beneath his hands as he kneels behind her and licks her arsehole. It’s different than licking cunt, not wet and messy, but there’s an odd tangy flavor that he doesn’t mind that much. It’s arousing to see his composed Astronomy professor bent over demanding that he fuck her arse with his tongue. She isn’t shy about voicing her desires, and he gets off on that nearly as much as he does doing something so improper.

Despite all the hours he spent with his head buried in Professor Bell’s cunt, he’s still a virgin. Not for long, though, when Sinistra orders him to fuck her arse. He isn’t very big yet, but he’s hard, and she doesn’t seem to mind his size when she moans and writhes beneath him. She’s so bloody tight that he almost comes as soon as he’s got part of his cock inside her, but he bites the inside of his cheek and starts saying the alphabet in Latin to keep himself from coming. He manages a dozen thrusts before he can’t control himself anymore. It’s just too good, and he comes before he can stop himself.

Since she’s still moving back against him, he knows she hasn’t come. Remembering his lessons with Professor Bell, he reaches around her and rubs at her clit and strokes her cunt with his fingers. When she comes, he listens to the noises she makes and knows she’ll be back. She’s going to want more just like Professor Bell, who has already been hinting to him that he should drop by the pitch and pay her a visit.

By the time he’s fourteen, Hugo’s added Professor Vector and Headmistress McGonagall to his list of inappropriate conquests. Vector loves it when he fucks her hard, and Hugo’s been able to get extra lessons on complex Arithmancy that impresses his mum during his Christmas holidays. The Headmistress is a feather in his cap, a rare opportunity that he took advantage of when it presented itself, and he came harder with her shuddering on his face than he has with the others because it’s just so wrong.

Unfortunately, he’s getting bored.

The only other female professors are going to be easy targets, especially now that he’s getting older and his body is developing more and he has so much experience that he’s more confident in his seduction. Sex itself is alright, but he doesn’t get as excited by the act itself as the other boys he knows. What gets him off is having sex with people he shouldn’t, taking the risk and using what he learns to gain little favors here and there. It’s so dull now, though, and he doesn’t even need the perks. He takes them because they’re available more than anything.

One night when he’s wanking, he gets inspired and knows what the next step should be.

He starts with Lucy, because she’s gullible and na´ve and always so eager to please. She tastes good on his tongue when she fucks his face, but she’s his age, so she doesn’t want to go any further. She feels guilty about it, too, which is just tedious. He has no interest in wasting time on remorse. Roxanne is eager to lose her virginity, so she’s easy. He plays the part of bashful cousin so well that she thinks she’s the one seducing him by the time she slides down onto his cock. She’s tight and wet, riding him as he strokes her small breasts. Afterwards, she apologizes for using him and makes him promise to never tell, and he knows she’s not going to be a repeat, either.

Molly surprises him. She’s older, so maybe that’s why she’s eager to fuck him when he starts targeting her. She seems to get off on their family connection, too, because she calls him cousin the entire time and is actually the first one to ever suck his cock. And she’s good at it. Definitely an expert, and he’s glad she wants to fuck again because it gets him off so fast when she has him shag her at the family Christmas party that year.

Lily takes a little effort, but not that much. They wank together, and it’s easy to transition from that to him using his fingers on her. The first time he fucks her is when her mum is right down the hall and her brothers are outside playing Quidditch. She starts to look at him, though, and it’s in a way that makes him think she’s got feelings for him, which just isn’t something he wants to be bothered with. He has ambition and goals, none of which involve having his cousin fancy him. When they start back to school for their fourth year, he convinces her to accept an invite to Hogsmeade from another boy, and he puts an end to his games with her.

While he might get off on fucking people he shouldn’t, she’s still his cousin, and he loves her. He doesn’t want her to get hurt by his games. His manipulation is successful because she’s soon smitten with another boy, and he goes back to his professors, who are easier to deal with than silly schoolgirls. He likes women anyway. Experienced women who know what they want. They’re still boring because he’s had them for years now, but he still gets off on it, so it isn’t that bad.

Still, he wants more, and he knows what he needs to do next.

After some consideration, he chooses Aunt Angelina first. It’s a challenge, and he spends most of his Christmas holiday working towards his goal. It makes victory even sweeter when she gives in and accepts his offer to distract her from some of her current stress. She tastes better than her daughter, and she definitely knows what she likes. He fucks in the store room of her husband’s shop, his uncle right outside working, and he comes deep inside her as she shudders on his cock. Like her daughter, though, there’s guilt when they finish, and apologies that he finds pointless. Still, he has a new pool of potential partners in mind, and he’s disappointed when it’s time to return to Hogwarts.

Summer break can’t come quickly enough.

He’s fifteen when he fucks Dominique and Victoire at the same time. Victoire’s had a fight with Teddy, ending things for what must be the hundredth time, and Hugo happens to be in the right place at the right time. They’re tipsy, drinking half a bottle of champagne they nicked from their parents’ cabinet, and it doesn’t take much to persuade them on an idea for the best revenge. It’s a deviation from his plan, but they’re the only two cousins he hasn’t fucked yet, so he can’t resist.

They fuck several times during the next few hours. Hugo manages to keep up with them, though it takes more control than he’s ever had to use before to prevent himself from coming too soon. Victoire’s arse is tight, and Dominique’s cunt is tight. They both enjoy riding his face, and Victoire makes Molly look like an amateur when it comes to sucking his cock. When he finally stumbles home that night, he’s worn out and wouldn’t be surprised if his cock is chafed. The next time he sees them, Victoire is reunited with Teddy, and Dominique sucks him off in the pantry.

Aunt Audrey is easier than he expects. Uncle Percy works a lot, and Molly obviously got her sex drive from her mum because Aunt Audrey rides him like he’s a carnival ride. She wants him to tie her up and fuck her until she screams, and she makes arrangements with his mum for her to pay him to help her with chores around the house. Thankfully, Mum has no idea the chores all involve orgasms and sex that is increasingly kinky. Hugo learns more from Aunt Audrey than he has from some of the books he’s read.

Before returning to Hogwarts for his fifth year, he also manages to shag Aunt Fleur. Uncle Bill is there, too, which is weird, but it also adds another level to how improper it is. Hugo plays the blushing virgin for them, letting Uncle Bill direct him and tell him how to please Aunt Fleur. When she’s fucking his cock while Uncle Bill is buried in her arse, Hugo comes so hard he sees stars. He returns to school with pleasant memories, and a new Transfiguration professor to seduce.

Professor Chang is beautiful, and she used to date Uncle Harry, according to the gossip at school. She looks even better with his cock in her mouth and her hand in her cunt. He uses the lessons he received from Aunt Audrey to drive her wild, and she seems to get off fucking a student as much as he does fucking a professor. It’s a good match and helps make the school year pass, plus he gets to work on accelerated Transfiguration lessons. He’s still doing extra work in several other classes, so he’s always busy.

His OWL scores are as high as his mum’s were, and she’s so proud of him that he feels like all the extra work has been worth it.

That summer, he’s sixteen, and he sets his sights on Aunt Ginny. She’s different than his other aunts because she’s related by blood, like his cousins, and he feels a sense of triumph when she succumbs to his advances. He fucks her arse because Uncle Harry never does, she tells him in between gasps and moans, and he likes how vocal she is when he fucks her hard. She calls him Ron while he’s sucking her cunt, and he knows she doesn’t even realize it because she’s thrashing around and rubbing herself against his mouth. The thought of his father fucking his sister gets him hard, and he covers her belly with stripes of his come when he has his orgasm.

Of course, that makes him think about his own sister, and he can’t stop thinking about it. Rose is out of school now, and she’s become a beautiful woman. Hugo isn’t sure how to seduce her, but he knows she’s his next target. It takes some effort, but he eventually manages to convince her that he needs guidance and has no idea what to do with a girl. He plays on her sisterly affection, and it’s worth it to lie to her when he’s got her pretty cunt in his mouth. She refuses to let him fuck her, but she lets him suck her cunt and even sucks his cock for the rest of the summer. Between her, Aunt Ginny’s arse, and ‘working’ for Aunt Audrey, Hugo has a productive summer.

Sixth year is interesting.

There’s a new Ancient Runes professor, and she’s actually the one who approaches Hugo. She threatens his marks if he doesn’t do as she says, and he’s curious enough to play along. From what he can tell, there’s animosity between her and his parents, so she takes it out on him. Professor Parkinson spanks him with her bare hand, and then she uses a toy to fuck his arse, which is something he’s never done before. Once he gets used to it, he actually enjoys it, not that he tells her that. He allows her to play her game for a few weeks because it gets him off, but he eventually grows weary of her believing herself to have control over him. So he has a chat with Professor Bell, who can’t stand Parkinson, and they work together to put her in her place.

It’s more enjoyable than he expects to fuck Professor Parkinson’s arse while she’s got her face buried in Professor Bell’s cunt, and it’s a nice distraction from the bad news he receives from home. His professors keep him entertained while he tries not to worry about Mum and how she’s handling the divorce. He can’t believe Dad moved out, and he spends his entire Christmas holiday with Mum because he wants to avoid Dad right now. He hates seeing his mum hurt, even if she’s put on a brave face and acts as if she’s fine with the divorce.

When he gets back to school, Hugo picks up where he left off. He’s seventeen now, and Uncle Bill told him he’s definitely taking after his dad when it comes to the size of his cock, so his professors are even more eager for his attention. He still enjoys the sex, still gets off thinking about fucking women he shouldn’t, but it’s all so tedious after so many years. He spends a lot of time with his Head of House, learning new charms from Professor Zabini and listening to stories about his parents back at school. Professor Zabini has never questioned Hugo about his extra-curricular activities with other professors, but there had been a scroll with helpful sexual charms left on his bed during third year, so Hugo assumes Zabini suspects the truth. Zabini treats him like an adult, and he enjoys that a lot.

By the time summer break arrives, Hugo knows what he wants. Knows who he wants.

It takes more effort than any of his other conquests, and he almost resorts to using alcohol or a potion to influence the outcome, but that would be cheating. Mum is suspicious, of course she is, and it’s exciting to have such a challenge once again. Hugo feels as if everything he’s learned over the years has been leading him to this moment, and he wants this more than he’s ever wanted anything or anyone before. He convinces Mum that she’s ready to let Dad go and move on, which is the biggest hurdle out of the way. It helps that Dad is already dating a younger woman and seems happier than he has in years.

He convinces Aunt Ginny to help after dropping casual threats about talking to Uncle Harry about her love of arse fucking. She fucks him hard after the threats, riding him until she’s come twice, and she promises to work on Mum so long as he keeps fucking her like that. It’s a mutually satisfying agreement, so he agrees on the condition that she succeed with his mum. He wants Mum to be willing, to want him as much as he wants her, and he thinks having Aunt Ginny talk about him in a sexual way will help alter her perception.

It’s an obsession, the ultimate conquest, and he can’t think of any woman who is more inappropriate to fuck than his own mother, so he has to have her.

It requires a subtle touch, so he starts leaving his bedroom door open when he wanks, starts wearing less clothing around the house, starts leaving erotic books open to stimulating entries where she’ll find them and read them. Between his efforts and whatever Aunt Ginny manages to do, he can sense Mum staring at him now in a way she never has before. Summer is half over before he finally manages to steal a kiss.

Mum rushes off, but she kissed him back at first, so he considers it a success. Two nights later, he hears her in the hallway and starts wanking, making noise and calling out for Mum as he comes all over his hand. He can feel her watching from the dark corridor as he licks his hand clean. It’s a surprise when she comes downstairs in a skimpy nightgown the next morning, and he sees her knickers when she bends over to get a pan out of the cabinet. He’s hard almost immediately upon seeing the dark hair against the white knickers, and he realizes she’s not wearing a bra when she sits down at the table, the shadow of her nipples evident against the thin fabric of her nightgown.

It gets worse from there.

She starts leaving her door open, and he stands in the dark watching her fuck her hand or a toy as she plays with her tits. She wears skimpy clothes that barely cover her. She makes suggestive comments about men and sex all the while being demure and untouchable. All those things yet she won’t let him touch her or accept any type of sexual advance he subtly makes. It’s leaving him frustrated and so horny he can’t stand it. He fucks Aunt Audrey so hard that he leaves bruises on her hips, and Aunt Ginny can’t sit down by the time he’s finished with her arse.

He’s reaching his breaking point.

The next time he catches her masturbating, he doesn’t lurk outside watching. Instead, he enters her room and crawls up her bed and sucks her fingers clean before he licks her cunt. She doesn’t push him away. When he pushes his cock inside her, she pulls him closer and kisses him, calling him her good boy and praising him for taking care of her. It feels better than anything he’s ever imagined, and he fucks her over and over until she’s got his come in her cunt and her arse and coating her beautiful tits.

As he snuggles close to her, he tells her about everything he’s done, answering her questions honestly and without shame. It seems to excite her, hearing about the women he’s shagged and the stories of how he’s manipulated his own cousins and aunts into fucking him. When he’s finished talking, Mum brushes her fingers through his hair and tells him about the professors and friends’ relatives and the other men she’s shagged to satisfy her own need for excitement and her desire for the ultimate inappropriate conquest. Hugo smiles as she talks, cuddling closer as he listens to her memories.

He’s really glad that he takes after his mum.