This was originally a commissioned work for The Merry Mage, a talent digital artist, as an accompaniment to a series of NSFW art. This isn’t cannon by any stretch of the imagination, with creative liberties taken with both characters and the story line. For those who want to see the fully illustrated version, and more of our work, ill drop a link at the end. Enjoy – Max

“I solemnly swear that I am up to no good, “Harry whispered.

The Marauder’s Map revealed itself, black ink spreading across the parchment showing the layout of Hogwarts and all its inhabitants. Hiding under his duvet, Harry used the light of his wand to study the map.

He scanned his dorm and the common room first, making sure no students were studying late or sneaking in or out. All was quiet and as it should be. Then he glanced over to the girl’s dorms. Laid out as a mirror copy of the boy’s dorm, it too, was quiet. The target of his planned activity was marked as a small black dot tagged ‘Hermione Granger’.

To her right was another small dot tagged Ginny Weasley, and to her left, two dots marked Padma and Parvati Patil. Curiously enough, the Indian twin’s dots overlapped each other, although the lack of movement suggested they were both asleep.

Harry watched the map for another few minutes and then muttered, “Mischief managed”, the ink fading away and leaving the parchment blank again.

As quietly as he could, Harry slipped from his bed and then vanished as he threw his invisibility cloak over his shoulders. He left his room without incident.

It was risky leaving his dorm. If caught, it would be a week of detention. Considering his destination was the girl’s dorms, there would be several awkward questions asked. Somehow, simply stating “it was a dare” wouldn’t cut it.

It was, however, the truth.

It had all started as a bet he’d made with the Weasley twins, Fred and George. The bet itself was of no concern. Instead, it was the dare he now had to complete as a forfeit for losing. He should have known those two would have twisted the rules to their advantage.

Harry expected the penalty for losing to be something like flying his broom through the grounds while naked or dung bomb Filch’s office. Not even close.

“We want you to sneak into the girl’s dorms, go to Hermione’s room, and fuck her in the ass,” Fred had announced when Harry begrudgingly accepted he’d lost.

At first, he thought he had misheard. But when George echoed his brother, Harry could scarcely believe it. They wanted him to sneak in and butt fuck his best friend. Well, best female friend. The twin’s younger brother Ron held the best friend spot.

Getting over the initial shock of the ordered ‘punishment’, although you could hardly call it that, Harry agreed. He couldn’t deny he often fantasied about screwing Hermione and understood he was firmly in the friend zone. He also knew she and Ron were crushing on each other.

Everyone knew it. It was obvious. The only two who didn’t seem to notice were Hermione and Ron themselves!

But doing it as a dare was a loophole Harry hadn’t thought of. Bets and dares between wizards are a little different from the muggle equivalent. All bets began with a charm to ensure all bets were fair and all forfeits or dare’s carried out.

Failure to do so resulted in some very unpleasant and often painful ramifications.

It took him a while to plan precisely how he would manage to do it. His first problem was getting into the girl’s dorms. Simply using the stairs was a no go. Any attempt resulted in the stairs turning into a slide, sending the encroaching male shooting back down. So, stairs were out.

Apparition was out too. Although Harry had passed the exam, powerful enchantments made it impossible within the grounds of the school. Only house-elves could successfully do it. Their magic operated on a different set of rules to humans.

Harry had considered asking the friendly elf Dobby. After all, Harry had tricked Lucius Malfoy into giving Dobby a sock, therefore freeing him. But, once again, Harry dismissed the idea, seeing the house-elf’s good meaning but slightly twisted set of logic as a liability.

The solution came when Harry was recounting his retrieval of the golden egg during the Triwizard tournament to some wide-eyed first years.

He could fly in.

Harry had stashed his broom in the hallway and was going to simply fly from the boy’s dorms to the girls. He couldn’t fly directly from his room to the girls, as the windows didn’t open. But the windows in the corridor did. That was his exit and entry.

Hogwarts was heavily warded, but most worked on the assumption anyone attempting to break in would be outside the wards. After all, why would someone already inside need to break in? Therefore, the windows themselves were pretty easy to open with a simple alohomora spell. Problem 1 solved.

Problem 2 was how he was going to fuck Hermione. Well, that was easy; he just had to stick his dick in her butt. The tricky part was doing so without Hermione waking up and blasting him into a million tiny pieces.

Hermione was scary intelligent, and while usually reserved, had occasionally ‘lost it’ and showed her angry side. Brilliant witch + bad temper = scary and, in this case, a very dead Harry. Not ideal.

However, while magic could be his demise, it could also be his saviour. Quietus would create a dome that would prevent any sound from waking Hermione’s roommates. They could just as easily incinerate Harry if he were caught. That was half the solution.

Part 2 came in the form of sleeping dust. It was one of Fred and George’s concoctions. They guaranteed its effectiveness, but after being cheated in the dare that got him here, he decided to test it himself.

He waited until Ron fell asleep, then doused him with the sleeping powder. Harry poked, prodded, and violently shook Ron without him waking. He even levitated him out of the room and down the stairs without any problems.

So, entry and execution of his plan sorted, Harry set about operation ‘Analize Hermione”.

With his invisibility cloak securely wrapped around him, Harry snuck down to the end of the boy’s dorm’s corridor and mounted his trusty firebolt. As a skilled flyer and seeker for Gryffindor’s Quidditch team, navigating his way to the girl’s dorm and though their window was no challenge.

Once inside, Harry quickly rechecked the Marauders Map. It was good he did. Parvati Patil was awake and making her way to the shared bathroom a few doors down from her dorm room. It provided an opportunity for Harry.

Parvati hadn’t closed the dorm room door when she left, so it allowed Harry to slip inside without trying to open the door himself and risk waking the girl inside. Set up exactly like Harry’s room, there are four small double beds, each with a bedside cabinet, a chest of draws and a small wardrobe.

On the far right was Ginny, the youngest of the Weasley clan. Just like her brothers, she had the trademark bright ginger hair and freckles. Harry would admit he found her attractive, but she was his best friend’s little sister. That was against the ‘bro code,’ right?

To Ginny’s left was his target, Hermione. To her left was Padme Patil, and farthest to the left was Parvati’s bed. Harry waited hidden under his cloak until Parvati returned. Harry watched as she headed towards her bed but instead stopped at the foot of her sister’s bed.

Harry remembered seeing the twin’s dots overlapping in the map and watched curiously to see what happened. When Parvati shrugged off her dressing gown, Harry nearly swore out loud and gave himself away. The young Indian twin was completely naked underneath. Even in the dimly lit room, Harry could see every perfectly tan inch of her body.

Naturally slim, she had very little fat, giving her a slender built. Long toned legs, pleasantly wide hips and rounded butt, tiny waist, and perky round tits. Not the biggest, but delightful to see all the same.

Harry’s cock hardened at the sight of the nude Indian witch. He regretted not paying her more attention when she agreed to be his date to the Yule ball. If he hadn’t been so distracted by Cho and the trials of the tournament, he might have been far more intimately familiar with her beautiful body.

As shocking as her choice of, or rather lack of, sleepwear was, who she climbed into bed with was her equally naked twin. Parvati shuffled backwards to be the little spoon to her sister, who, while still asleep, wrapped her arms around her sister.

They both shifted until they had their body touching at every possible point, bare skin against bare skin. The familiarity with which they moved together led Harry to think this was a more regular occurrence rather than a chance discovery. It also suggested that Hermione and Ginny both knew of their closer than usual sibling relationship and never told anyone.

Once again, Harry chastised himself for being so distracted at the Yule ball. If he had been more charming and attentive as a date, maybe it wouldn’t have been just one sister he was more intimately involved with. Twins share everything right, even boyfriends. They certainly have no qualms about being naked together.

Realising he was getting too distracted, he forced himself to focus. He waited patiently until Parvati’s breathing slowed and deepened, then set about Part 2 of his plan.

“Quietus,” Harry said, focusing on casting the spell.

It wouldn’t do for the spell to fail mid-fuck. No amount of ass, even one as fine as Hermione’s, was worth dying for. While the Hogwarts uniform wasn’t exactly flattering, Harry had seen Hermione in enough pairs of jeans to know she had a great ass.

Being the first to part her peachy little derriere and plunder her virgin asshole has hardly a punishment. If he had known the forfeit before losing the bet to the Weasley twins, he might have lost on purpose.

Setting about the final preparation, he poured the sleeping dust into his hand. To an outsider, it would appear as if a disembodied hand just popped up. In fact, it was Harry’s hand leaving the folds of his invisibility cloak. With a single long breath, Harry blew the magical powder over the sleeping witch, ensuring she wouldn’t wake anytime soon.

Harry moved, climbing onto the messy bed. Books and scrolls covered half the mattress. Hermione was a true nerd, obsessed with knowledge. Her need to know the answer to every question was overwhelming. An ever-burning candle was set on her bedside table, casting a pool of warm amber light. At times, she would “fall down the rabbit hole” and spend all night reading without realising. Luckily, it was not one of those nights.

Hermione had fallen asleep atop the bedsheets. Like most nights, she likely fell asleep while reading, hence the still-lit candle and books strewn across her bed. Harry studied his friend’s face for a moment. Asleep and relaxed, she looked adorable. She often worried, and it showed in her face, clouding over her otherwise pretty features.

With nearly dying every year at school, her worry was understandable.

Harry’s eyes moved lower. The sleeping teen wore an oversized pink tank top and white panties. With a simple spell, her shirt disappeared, only to reappear a few feet away.

Perky and perfectly rounded, her breasts sat proudly on her chest. Even laid flat, they resisted the pull of gravity, her light brown nipples pointing to the ceiling. Harry couldn’t resist and reached to squeeze Hermione’s breast, pausing just inches away.

Harry was confident in the sleeping dust. He has tested it thoroughly. But now, just moments away from feeling Hermione’s tits, he had a moment of doubt.

What if it didn’t work? What if her eyes flew open as he squeezed her tits?

Harry steeled his nerves. This would work. He closed the gap and moaned softly as his hand closed over Hermione’s breasts. Just slightly bigger than his hand could hold, they were larger than he imagined—their size hidden by the fit witches’ less than flattering wardrobe.

The reality was much better than any fantasy. Something Harry, and no small number of other students, had often thought about. Her skin was warm, the pliant flesh of her tits felt fantastic. Her small nipples hardened against his palms, Hermione’s lips parted just slightly, her breath catching.

While her mind was deeply under the influence of the sleeping powder, her body’s physical reactions were unaffected. She moaned softly, a cute little dimple appearing between her eyebrows. Harry cupped her tits, lightly pinching and rolling her firm nipples between his thumb and forefinger.

She gasped slightly louder. Her chest arched as Harry sucked a nipple between his lips. Hermione gasped louder again. Harry was glad he had taken the time to cast his silence spell. No one beyond its limits could hear anything from within. Harry, meanwhile, could listen to everything happening outside.

Hermione’s chest heaved as Harry suckled at her nipples and squeezed her tits. Her soft breasts swelled between Harry’s fingers, and he squeezed harder, her nipples like hard little candies between his lips. He wondered for a moment if there was a spell to make a girl lactate. His cock throbbed at the thought of her creamy, milky delight flooding his mouth.

If anyone knew the spell, Hermione would.

With reluctance, but with anticipation also, Harry left her breasts and kissed down her stomach. He followed the small valley down the centre of her stomach. Hermione gasped with a bit of a shudder when Harry flicked his tongue into her belly button.

Despite her bookish nature and preferring the library to the gym, she was surprisingly athletic. Not superstar athlete fit, but nicely toned with hardly any extra fat. Her stomach was lightly defined and slightly concave. The bottoms of her ribs and tops of her hips were clearly defined.

Hermione’s panties were a simple white bikini cut. Unlike her shirt, Harry chose to savour the experience of removing her underwear. Gripping the waistband over her hips, Harry slowly pulled them down. Inch by inch, he worked her panties down, first exposing the V between her hips, bare and smooth.

Her sweet cunt slowly became exposed to Harry’s lustful gaze. Shaven and smooth, her sweet inner lips just peaked out, her clit still hidden beneath its hood. Harry could smell her arousal, a sweet and fresh smell that he adored.

The white cotton clung to her pussy as he pulled them down her thighs. As they peeled away, a single string of her juices connected them—visual evidence of how actively her body was responding. Slipping her panties off her feet, Harry slid back up her legs. His hands adoring their silky smoothness. Gently parting her thighs, hands sliding beneath and over, he leaned in close.

That wonderful aroma filled his nose again, and he couldn’t wait any longer. He had to taste her. He pushed his tongue past her outer lips, sliding from bottom to top, her sweet juices gathering on his tongue. She tasted amazing, and Harry savoured every drop of her juices. His tongue teased the entrance to her pussy, gently probing and pushing inside. He was shocked when his tongue brushed against her hymen.

She was a virgin!

True, Hermione’s first love had always been books. She spent more time in the Library than the following three most frequent students combined. However, Harry had presumed she had already had sex. Maybe Krum after the Yule Ball, or a late-night tumble between the stacks of the library’s forbidden section.

Hermione was moaning and breathing deeply as Harry gently tested her hymen. Licking back up through her moist lips, he circled her clit. Hermione gasped louder, her hips fighting against Harry’s grip. What had started as a simple bet to fuck Hermione’s virgin ass had already become so much more.

Rising, Harry bent the young witch’s legs backwards, her knees coming level with her hips. Leaning forward and pinning her hips, Harry moved his cock to press against her wet pink lips. The heat of her pussy spread up his cock to his balls and throughout his body. His cock throbbed painfully, eager to deflower the young maiden. Leaning down, Harry kissed Hermione, her lips instinctively reacting and kissing him back.

Unable to resist her virgin cunt any longer, his hips pushed, his blunt cock head pressing against her hymen. For a few seconds, it held, stretching against Harry’s cock. Then it tore. Hermione let out a scream at the brief flash of pain. Harry moaned and swore as his cock speared into her pussy until his balls pressed against her.

It was fantastic. Hermione’s soft moans were sweet songs to his ears. Her pussy was hot and tight, her silken depths hugging his cock tightly. Every few seconds, her teen cunt would tighten and shudder around his shaft, making him groan in pleasure. Hermione’s small whimpers slowly changed from the pain of losing her virginity to those of pleasure.

Her hips pushed back against Harry. Taking that as his cue, Harry pulled back until the flared head of his cock caught against her tightly stretched entrance. Harry swore again as he pushed back inside Hermione. Her pussy felt like it was pulling him back inside, eager to be filled again.

Hermione’s body rocked and twisted as Harry steadily built up a rhythm. Entirely at the mercy of her physical self, freed from the limitations of her mind, Hermione came alive. She moaned and gasped in pleasure; her cute, usually serious face instead showed her joy. It was a beautiful sight to behold.

Harry was delighted with the pleasure of fucking Hermione. The feel of her tight cunt wrapped around his cock was just fantastic. The way it sucked and squeezed his cock as he pulled out, then relaxed and pulled him deeply back inside was just glorious.

He stared down at Hermione, loving how her tits bounced in time with his thrust. The way her face twisted in pleasure and her cries built his arousal. Harry wondered if her mind was at all aware of what was happening. What dreams was she having as her virginity was taken?

Hermione’s breathing started to grow ragged and uneven, her pussy began to squeeze and shake. Her face scrunched up, and her body tightened. For a few seconds, she went utterly still.

Her body exploded, bucking and shaking violently as she screamed her way through her first orgasm. Her pussy went wild around Harry’s cock in a way he couldn’t describe. Lost to his physical self, his abs tensed, balls tightened, and his cock throbbed as he came.

The orgasmic rapture flowed freely between the two teens, and they came together. Harry flooded Hermione’s cunt with cum while Hermione creamed around Harry’s cock. Time ceased to exist as his orgasm burned through him, every nerve alight with pleasure.

Slowly, Harry recovered from his post-orgasmic daze. That has been the most intense moment of his life. Quite something when you consider what he had been through the past few years. From his first year at Hogwarts and the Philosophers Stone to the Chamber of Secrets, rogue Dementors, and troublesome house-elves. The Tri-wizard tournament and the Order of the Phoenix, and the hunt for Horcruxes’s. This topped them all.

And the crazy thing was, it wasn’t even the main event.

The dare had been to fuck Hermione’s virgin ass as she slept. Harry had already gone way beyond the dare’s original intent. It made sense. He had an opportunity to fuck a hot and sexy girl he would never usually have a chance with, with no consequences. Why wouldn’t he take full advantage?

Harry slowly pulled his cock from Hermione, who moaned softly. She thrust her hips weakly against Harry’s pinning hold. Harry shuffled back, releasing her hips. Her newly deflowered pussy leaked their mingled cum. It was a wonderfully obscene sight.

Harry’s cock was still hard as iron despite having just cum. Youthful virility and the anticipation of what was next maintaining his erection. Hermione’s tits bounced as Harry pulled her further down the bed, then flipped her onto her front. Folding a pillow in half, he shoved it under her hips, making her ass pop up. Perfectly posed to show off her cute bum.

Harry hadn’t anticipated being so entranced by Hermione’s nude body. Obviously, to a teenage boy, seeing any girl naked is incredible. However, Harry hadn’t expected Hermione to have such a fantastic body. Even with the less than flattering school uniform and her fairly conservative dress sense, she clearly had a decent body. Her tits, while not huge, nicely filled out her sweaters, her waist slim, and her hips well rounded. Her ass was her best feature, but overall, she was pretty hot.

The girl next door kind of hot, not drop dead gorgeous hot.

With her clothes out of the way, however. Well, that was a different story. Her boobs were bigger than he thought, probably C-cups, perfectly rounded and just slightly larger than he could fully hold. Her stomach flat, her waist pinched in before flaring to her hips which flowed down to her toned and slender legs.

Of course, you couldn’t forget the delight of her freshly fucked pussy and virgin asshole just waiting to be stretched.

Harry straddled her thighs and caressed Hermione’s fantastic ass. Some guys like a big, fat, plump and soft ass that would shake and jiggle. Harry preferred more petite, compact, and firm butts. Hermione’s ass was a perfect example. Athletic underlying muscle, a soft layer of cushioning fat and tight smooth pale skin, all rounded into a hot little package. The kind of butt you could bounce a Galleon off.

Harry couldn’t resist giving her ass a few firm slaps, turning her pale skin a light rosy pink. Hermione gasped and wiggled her hips, shifting her ass from side to side.

Hermione was just as stunning from behind. The pillow beneath her gave her spine a graceful curve, and it pushed her hips into a wonderfully erotic pose. The outer curve of her boobs was just visible and her hips creating perfect “fuck me handles”. Her lower back had two little dimples that just screamed adorable. Dimples of Venus, they were called.

She was stunning. While Harry knew he was deep in the friend zone, if Ron ever fucked up, Harry would gladly be the rebound.

A contented sigh, the creak of a mattress, and the shifting of sheets caught Harry’s attention. Harry looked to his right at the Patil twins and sighed in relief. Just Parvati turning over and snuggling into her sister. It occurred to Harry that he should have used the sleeping dust on the twins and Ginny too. If Harry had arrived 10 minutes earlier, he might have been caught by Parvati heading to the toilet rather than slipping in before she came back.

True, Harry had his invisibility cloak on, but Hermione’s disappearing clothes and the hand-shaped imprints on her tits might have given him away. But hindsight is twenty-twenty.

He waited just momentarily to listen to the twins’ breathing. Slow and even. Perfect.

Shuffling a little closer, Harry aimed his cock at Hermione’s pussy, peeking out between her thighs. Thrusting, he slid his cock into her cunt until his hips hit Hermione’s ass. The prone teen gasped at the sudden intrusion and then moaned. In this position, Hermione’s pussy was even tighter than before. Harry groaned and swore softly as Hermione’s cunt shivered around his dick. Grinding his hips in small circles, Harry corkscrewed his cock, making sure it was well coated in their shared cum still leaking from Hermione.

The teen witch moaned softly as Harry withdrew his cock. Spreading her legs, Harry knelt behind her. Slightly adjusting his hips, he pressed the cum slicked head of his cock against Hermione’s ass. Seeing the fat flared head against her tiny puckered asshole, Harry found it hard to imagine his cock fitting. Hard, but incredibly arousing.

Leaning forward, Harry braced himself on his arms, hands going over Hermione’s, their fingers interlocking.

“I’m about to take your ass, Hermione,” he whispered into her ear. He was unsure if the words would be heard.

Harry sat back up, kneeling behind Hermione’s proffered ass. Her hips provided the perfect handles that Harry held in a firm grip. But in a moment of sudden clarity, Harry paused. He looked down at his sleeping friend and her submissive pose. Doubt started to enter Harry’s mind. If she had been conscious, awake, he wouldn’t dare try this. With or without her wand, he wouldn’t try to rape her.

It would have been easy enough with magic. He could use Petrificus Totalus to bind her entire body, or Stupefy to knock her unconscious. He could even use Obliviate to make her forget it ever happened. There were a number of potions that could mimic the sleeping dust or make her compliant. He could have simply used a love potion so she would willingly sleep with him.

With magic, there were a dozen ways he could have forced her against his will or even made her be willing. But to Harry, that felt wrong. It was something he could never see himself doing.

So why did it feel different now?

Was it because it was only her physical body he was using? Her mind was safe and secure in its unconscious state. She wouldn’t have any knowledge of what had happened beyond the physical tells.

With how sexually responsive her body had been, Harry wondered how she would react if she were an active and willing partner. She was usually so serious and tight-laced. Would her personality limit her sexual freedom? Was this the only way her mind would allow her body to fully appreciate her sexual capacity?

The throbbing need of his cock, and Hermione’s soft lustful moans let him decide. If she were conscious and aware, things would be different. However, in her current state, with only her physical body aware, she enjoyed what was happening. There was no harm, no malice or ill intent. It was purely shared physical sexual pleasure.

With new confidence, Harry pressed the blunt head of his cock against her ass and started to push. Hermione gasped and let out a cute little squeak, but made no attempt to move.

Her ass, however, resisted. The tight right of muscle fighting against the increasing pressure of his cock.

The harder Harry pushed, the more vocal Hermione became. She gasped, moaned and whimpered, her shoulders and head twisting and turning, but her ass stayed still. Her hands formed fists as she grabbed the sheets, knuckles turning white.

Harry’s cock was harder now than it had ever been. However, her ass continued to resist his efforts. He started to fear his cock would bend before pushing inside Hermione. Hermione’s back tensed, her shoulders hunching. Then she slowly relaxed, letting out a long but shallow breath. Just as she paused to take another breath, her ass relaxed and relented.

With the force Harry had been applying, he couldn’t stop himself from savagely thrusting his entire length into Hermione’s virgin ass. The suddenly impaled teen screamed and Harry swore and shuddered at the intense feeling.

The velvet sheath of her ass was almost painfully tight and hot. Hermione’s clenching fists and cries made her ass squeeze and quiver around Harry’s cock. The molten heat of her bowels flooded up Harry’s cock and spread through his body. The convolutions and tight grip of Hermione’s ass were fantastic. Even tighter than her virgin pussy, but no less euphoric. Harry tried to pull back but moved no more than half an inch. Hermione’s ass locked down too tightly to let him move any further.

He pushed back in, his balls, already heavy with another load, pressed against her wet pussy. Pulling back again, he managed another half-inch before she squeezed down with her ass again. Slowly, bit by bit, Harry built up the length of his strokes until he was fucking Hermione with the entire length of his cock. From being pressed firmly against her delectable derriere until the flared head of his cock locked against her tightly stretched ass.

Harry pushed fully back inside and started to slowly fuck the sleeping teen. Her ass pulled his cock deeper. The once resisting orifice was now reluctant to release him. The further he drew back, the harder it pulled him back in.

By the time Harry was properly sodomising Hermione’s ass, her whimpering cries of pain had changed to moans of pleasure. The shifting muscles in her back were highlighted by a soft sheen of sweat. The mix of blue moonlight and amber candlelight across her body was incredibly erotic.

Slowly, Hermione’s ass started to relax and loosen slightly. Harry was able to pick up the pace. His single driving thought to fuck harder and faster. Hermione’s earlier cries now mixed with clear sounds of pleasure. With her mind locked away and her body in charge, there was no anger: no shame, no humiliation, no feelings of being degraded or abused. There was pain, and there was pleasure. Sometimes they were even the same. Right now, Hermione’s pain and pleasure bled into one another.

Harry half wished that Hermione and Ron would never work out, or at least not yet. He wanted the chance to experience this with Hermione, wanting it to. Compare how her physical and mental, or emotional self-reacted. Harry was glad he had already filled Hermione’s cunt. It gave him the stamina to enjoy her ass. To truly savour how it felt. Even so, Harry couldn’t fight the tight squeeze of her ass for long. It felt just too good.