Harry's Bucket List - Chapter 2 - Flight_OfFancy - Harry Potter (2024)

Chapter Text

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Chapter 1: New Year New Me

After a thoroughly intense night of fun with Gabby, Harry awoke the next morning tired and sore in all the right places. It was still dark out when he woke. Gabby was dozing peacefully against his side, her raven hair splayed out all over his chest and her naked body pressed flush against him.

He wanted nothing more than to stay in bed and worship the tattooed vixen's body until the sun rose and set once more. In all honesty, he probably could. The Knightbus was fairly cheap, and a ride to Hogsmeade would take a couple minutes at the most on that deathtrap of a bus. Still, he knew if he wasn’t at least SEEN boarding the train, Dumbledore would probably send the entire Order to hunt him down, and the last thing he needed was Mad-Eye Moody kicking down the door while he and Gabby were mid-shag.

Quietly as he could, Harry dressed. Just as he was tugging on his trainers a groan from the bed signalled Gabby rousing from her sleep.

“Wha’timeiset?” She grumbled, rubbing the bleary sleep from her eyes.

Harry sat on the edge of the bed and ran a hand through her hair. “Shh love, it’s still dark out. Go back to sleep.”

“You’re leaving?” She asked with a pout.

He nodded, running his hand down through her hair and across her cheek. Gabby shivered and leaned into his touch. She looked up at him, her eyes full of an indiscernible emotion that he just couldn’t place.

“Well then… Kiss me like you’ll miss me?” She asked with a nervous smile.

Harry smiled back and leaned in, capturing her soft lips with his. Gabby sighed happily and wrapped her arms tight around his neck. They stayed like that for some time, softly trading kisses while holding on to each other tightly. Eventually though, they broke apart, Gabby frowning heavily as he whispered one last goodbye and walked out the door.

It was an odd feeling. He did not doubt that he and Gabby had grown to care for one another over the last couple of months, but he never expected leaving to pain him this much. It was like a pit in his stomach, gnawing uncomfortably at his throat. He didn’t love her, but he was certain now they were a bit more than just ‘friends-with-benefits’.

Taking a cigarette from his coat pocket, Harry lit it with a snap of his fingers and took a drag. He breathed out the smoke with a sigh, and then with a turn, disappeared with a ‘pop!’.

He never saw the pair of eyes peering down at him from Gabby’s bedroom window.

The Hogwarts Express gleamed in the mid-morning light, shining proud and crimson for all on the platform to see. New students and old students alike chattered excitably, saying their farewells to their loved ones and boarding the train for another exciting year at Hogwarts.

Harry was not one of them. People all around stared and whispered as he passed. It reminded him of last year when most of the general populace believed him an attention-seeking villain. The only difference now was that those same people stared at him in awe and reverence instead of malice and disgust.

With Voldemort officially out in the open and Fudge quite literally kicked out from his post as Minister, the entirety of Wizarding Britain was now looking to him as their so-called ‘saviour.’

It almost made Harry laugh.

He was no one’s saviour. Not his parents’, not Cedric’s, not Sirius’s, and definitely not their’s.

Harry was his own man now, and at this point he had but one virtue he was sticking by. Damn everyone who wasn’t him.

Not even bothering to look for his friends, Harry quickly boarded the train, taking advantage of everyone’s laxity outside to find the best compartment available. He stowed away his trunk and sat back. He already sent Hedwig on ahead earlier. The snowy owl hated the train and always preferred fling to Hogwarts anyway. Harry agreed with her in his honest opinion. An entire society of people who could teleport at will, and they always choose the slowest modes of transport for everything. It made no sense when he thought about it.

His thoughts were interrupted as the door to his compartment slid open and a brunette missile slammed into his stomach.

“Oof! Hello to you too Hermione.” He groaned.

The girl released him, her face scrunched up in fury that made her look more cute than menacing, before raining down a series of blows across his arm.
“No letters?! Not even a single call?! You stupid! Bloody! Prat!” The bushy-haired bookworm roared.

Harry winced as slap after slap landed across his chest. “Ow! Ow! Stop- Hermione!” He exclaimed, catching her hands mid-assault. “Look- I’m sorry for not writing. I needed a little space this summer, but I shouldn’t have gone completely radio silent.”

Hermione’s fiery facade melted somewhat, morphing into a look of utter worry. Her lips trembled and she sniffled slightly before once more wrapping him up in a bone-crushing hug.

“I was so worried! With You-Know-Who out there now I- Well I thought something must’ve happened to you!” She cried.

Harry held her tightly, whispering soft apologies into her ear as he rubbed her back soothingly. Before this summer, he hadn’t been one for physical affection such as this. Growing up receiving nothing but looks of disdain and venomous words shouted at you didn’t leave a lot of room for touchy-feely moments like this. But after opening himself up these last few months, Harry found himself more open to affection such as this.

…and it didn’t hurt that Hermione’s curves pressed up against him felt amazing .

As the brunette untangled herself from him, Harry took a chance to discreetly check his best friend out.

She had certainly grown a lot over the years. What used to be the body of a mousy know-it-all bookworm was now the filled-out frame of a sexy, petite witch with curves in all the right places. She was no Lavender Brown or Susan Bones, but Hermione definitely had the ‘hot librarian’ look down.

Just then, the train suddenly lurched under them and the distinctive feeling of the engine churning as the express chugged away rumbled beneath their feet.

“Guess Ron isn’t joining us then?” Harry asked. “I suppose he’s angry at me for not writing as well?”

Hermione winced and bowed her head. “More so because you told Dumbledore you’d rather stay with your relatives than the Weasleys.”

Harry cursed under his breath. Leave it to the meddlesome old man to throw another wrench in Harry’s life. A few days ago, the aged headmaster had shown up to Privet Drive unannounced. Thankfully Gabby had been working late that day or else Harry wouldn’t have been at the Dursleys where Dumbledore expected him to be. The old wizard asked Harry to join him on a quick trip to ‘an old friend’s’ house. The Boy-Who-Lived had all of about three seconds to agree before he was suddenly whisked off in a bout of side-along apparition

The fact that Dumbledore had done so only because he needed to use Harry as some sort of bait to lure Slughorn out of retirement infuriated him. Though he supposed the man was important if he could give them an edge over Voldemort. Just because Harry knew he was going to die didn’t mean he wanted Voldemort to win.

It had taken some convincing afterwards to get Dumbledore to allow him to stay at the Dursleys. It was ironic that not a year prior Harry had practically begged the old headmaster to take him away from his relatives. Fate was funny that way. In the end, all it took was some half-arsed excuse about not being ready to face his friends again in the wake of the DoM fiasco that allowed Harry to stay. Was it a low-blow? Perhaps, perhaps not. Harry really didn’t care.

“Right. I’ll try and talk to him.” He sighed.

Hermione smiled sympathetically and patted his leg. They fell into a comfortable conversation after that, with Hermione regaling him with every detail of her summer break and all the new books she read during the course. A few more friends stopped by as well, staying long enough to chat for a few minutes before begging off to greet their other classmates as well.

Neville, Luna, Susan, and many others from the DA made appearances. Even Ginny came by, the red-haired chaser having no issues with Harry’s decision to stay at the Dursleys as her older brother did.

“He’s just being a broody prat. He’ll come around before dinner tonight, just you wait.” She had said. Though Harry had little faith that her words would come true.

The constant barrage of people coming to greet him did help Harry come to one conclusion: He was either blind or just a plain bloody idiot!

How could he not see just how downright gorgeous his female classmates were?! Half of them had figures that would put every muggle bikini model to shame, and the other half would still give them a run for their money.

Sure he had noticed a few of them before. There wasn’t a bloke out there who could see Susan Bones’s tit* and not fantasize about them in the shower. But he’d have never given others like Luna or Ginny the time of day!

Sure before he knew they were cute, pretty even, but it was like he was seeing them in a whole new light this year! Ginny’s long legs were practically burned into his mind, not to mention how fantastic her arse looked. Luna too was a certain ethereal beauty to her, almost like how Tolkien described Lady Galadriel in the Fellowship.

Still, despite his recent sexual awakening, as it were, they weren’t pieces of meat for him to ogle, but his friends. Harry would still treat them with the respect they deserved.

However, that didn’t mean he couldn’t at least test out his newfound confidence with them. If the looks Ginny was sending his way were anything to go by, some of them wouldn’t exactly mind.

At some point between all the visits, Hermione had been squeezed against his side from the crowd of DA members who joined them in their compartment. The brunette had blushed at the close proximity but said nothing as the conversation flowed. Harry was intensely aware of Hermione’s body pressed against his. The heat from her body washed over him and he soon found his mind unable to focus on anything but the petite bookworm’s soft curves, much less whatever unimportant topic the others were talking about.

He unconsciously shifted in his seat. Beside him, Hermione gasped softly as his hand unintentionally brushed against her thigh.

Interesting.

Feeling a bit brave, Harry shifted again, this time resting his hand halfway atop the brunette’s knee. Hermione’s breath hitched once more, enough to where she had to feign a cough by clearing her throat. Harry smirked internally to himself. It seemed Ginny wasn’t the only one who would be…receptive to advances. He had always somewhat fancied Hermione over the years. What bloke didn’t fancy his female friends from time to time after all? Only he never pursued the thought because he never would dare assume Hermione liked him back. But now…

He moved his hand once more, placing it firmly atop her lower thigh. Hermione blushed bright red. She buried her face in a book to try and hide the flush in her cheeks. That wouldn’t do.

“Eep!” The girl squeaked, having been caught off guard as Harry gave her thigh a firm squeeze.

“Alright there Hermione?” Colin Creevey asked with a look of confusion.

“F-fine!” The girl stammered. “Just- Feeling a bit train-sick is all.” She provided with a timid smile.

Colin winced in sympathy. “You want us to go so we can let you lie down?” Around the compartment the other DA members nodded in agreement, all except for Demelza Robbins who was staring at Harry’s hand upon the bookworm’s thigh with an amused smirk.

Hermione made to refuse the younger boy’s offer with a shake of her head, but Demelza beat her to it.

“Why I think that’s a wonderful idea Colin! Come you lot, let’s give Hermione some space. She doesn’t need your ugly mugs making her even sicker!” The short chaser ordered everyone out in quick succession, but not before shooting the two of them a quick wink as she left.

The door slid close, leaving their compartment in a tense silence.

“Ahem- Ah… Harry? Y-you can let go of my leg now.” Hermione stammered after a beat.

Harry turned to face the girl with a small smirk. “Is that what you want ‘Mione?” He murmured.

“N-No! I mean- I d-don’t mind. I just thought with everyone else gone now-”

He silenced her by moving his hand farther up her thigh. The brunette slammed her mouth close with a muffled squeak causing Harry to smirk even wider.

Leaning in, he rested his face inches from Hermione’s blushing face, peering intensely into her wide brown eyes.

“And if I want to go further? What then ‘Mione?” His lips inched closer to hers. “What if I wanted to do this…” He finished the sentence by taking the final plunge, capturing her lips in a gentle kiss.

Hermione sucked in a sharp breath, her body going shock still for a moment or two. Eventually, however, the bushy-haired witch seemed to almost melt against him, whimpering needily against his lips. To his surprise she even deepened the kiss, sinking into his chest as she opened her mouth willingly to allow his tongue entrance.

Harry slipped his tongue inside, finding hers ready and willing to tangle with his without a fight. He took his chance then, as he explored his best friend’s mouth he also began to slowly move his hand further up her thigh, slipping easily under her loose skirt and finding the creamy smoothness of her bare thigh just waiting for him.

Hermione broke the kiss with a gasp, her breaths coming out in short fluttering pants.

“H-Harry! We c-can’t!” She whimpered as he leaned in, taking this chance to nip and kiss at the smooth expanse of her neckline. “S-someone could hear!”

Though her words said one thing, she made no move to stop him as he moved his hand further up her thigh. She could only mewl softly as his fingers finally brushed against the sweltering heat of her knicker-clad core.

“What was that ‘Mione?” He murmured teasingly in her ear.

Hermione gasped as he swiped his finger over her panties, rubbing her rapidly moistening slit through the thin material.

“I- I- Oh forget it!” She exclaimed.

To his surprise, the bookish girl grabbed him roughly by the collar of his shirt and yanked him forward, crashing their lips together in a heated kiss. He was dimly aware of her fumbling for a wand before casting some unknown spell at the compartment door. A silencing charm perhaps.

Hermione whimpered against his lips. Her hands clawed at his chest, fumbling around with no clue as to what they should be doing. Harry hummed in response and increased his pace, rubbing her soaked quim with quickened flicks of his fingers.

“O-Oh god!” Hermione cried. She gripped the front of his robes in an iron tight grip. Small whimpers like panting breaths were spewing from her lips.

Harry latched onto her neck, sucking harshly on her pulse point before, ever so slowly, he began to descend further down her body.

Hermione watched him with hooded eyes. Her chest fluttered with rapid breaths as he came to rest between her thighs. The brunette unconsciously opened her legs for him, giving him a full view of her creamy inner thighs and black lace thongs.

“Damn, I never expected you to be a sexy knickers type of girl ‘Mione.” Harry teased.

Hermione blushed and stammered out an excuse. Harry just smirked. Maybe there was more to Hermione than he even knew. A more kinky side… one he wanted to see just how deep it went.

With a whispered spell, the bookworm’s skirt and knickers disappeared before reappearing folded on the opposite bench, leaving her in just her thigh-high socks and white blouse.

Hermione squeaked and made to cover herself, but Harry caught her hands. “Ah ah.” He chided. “I want to see all of you ‘Mione.” He whispered huskily.

Hermione bit her lip before nodding hesitantly. Slowly she began to spread her legs once more, revealing her damp hairless slit to him. Harry’s co*ck lurched at the sight of her moistened sex. Like a spell washing over him, he leaned forward, grabbing the outside of her thighs and burying his face in her sweet c*nt.

Hermione cried out in ecstasy as his tongue flicked hungrily over her slit. The brunette grabbed his hair painfully for support as he began to devour her puss* with gusto.

Over the summer, Harry had racked up a lot of practice in eating puss*. Gabby absolutely loved it when he went down on her, and he found he loved it even more. To have a girl squealing with pleasure just from the simplest flicks of his tongue was addicting. So much so that he had worked hard to master the skill.

It was during his practicing over the summer that he discovered one very neat trick.

Drawing up a mental picture of a serpent, Harry opened his mouth wide and began hissing. The words he spoke were inconsequential, his mind going through some rock song or another that Gabby showed him, what was important was the language he spoke them in. Parseltongue wasn’t just good for conversing with snakes it seemed, it was also perfect for bringing a girl to a screaming org*sm.

“O-Oh! I’m- I’m! HARRYYYY!” Hermione cried loudly.

Like electricity running through her veins, Hermione’s hips trembled uncontrollably. Her weeping puss* ground against his face, smearing her juices all over his chin. She slurred incomprehensibly, her mind too clouded to form words as she came. Finally, his friend grunted and pushed his face away. She clutched her puss* protectively as the last few twitches of her org*sm ran rampant through her body.

“Gyuhhhh.” She groaned.

Harry chuckled to himself and quickly spelled himself and the girl clean.

“Alright?” He asked.

Hermione nodded shakily as she fought to catch her breath. “That was- Oh god.” She rubbed her legs together with a small moan and sat up. “What was that?” She questioned.

“I believe that’s what they call ‘Oral Sex’ ‘Mione.” He laughed.

She slapped his arm with a small glare. “You know that’s not what I meant. Prat.” She chastised. “I just- Well I never- Ugh.” Hermione threw her head back with a huff. Out the corner of her eye she saw the sun setting through the window, signaling their impending arrival to Hogsmeade Station. “We are so discussing this later. For now, out. I need to change.”
Harry didn’t bother arguing, nor pointing out the irony of her kicking him out to change after he just explored every inch of her womanhood with his tongue.

-

The opening feast came and went. Harry barely paid it any mind, only tuning back in every now and then when someone occasionally called him name. He didn’t even pay attention during the sorting. Watching an old dusty hat spout out the house names to a bunch of scared firsties wasn’t exactly peak entertainment in his opinion.

Still, he didn’t waste the feast lost in his own head. He received two separate notes. One appeared on his plate as the feast began. It was from Dumbledore, requesting Harry to meet with him after dinner. He vanished the note without a second thought, having no interest to spend another second than necessary with the old meddler. The second note, however, was far more interesting and expected.

Hermione had slid it into his pocket when they sat down. Harry was able to take it out and read it without anyone noticing thankfully.

ROR. 9:00. Don’t be late.

Simple enough. His bookish friend wanted to meet up tonight to discuss what happened on the train it seemed.

He smirked to himself, reaching underneath the table discreetly and giving her leg a pointed squeeze. She jumped somewhat and blushed from the few stares her outburst drew. Turning, Hermione shot him an exasperated glare before going back to her meal.

Harry chuckled to himself and turned back to his own dinner. Now that would be a much better way to spend his evening.

Harry entered the Room of Requirement five minutes before 9:00. Hermione was already there, a book in her lap and dressed in a very cute set of light blue pajamas. He also couldn’t help but note that she was sat on a bed instead of a chair or couch. It seemed the brunette had her own ideas of how this evening would go.

“You know classes don’t start till tomorrow.” He called out.

Hermione glanced up and rolled her eyes. “I’m not reading to study. Honestly, I’m not THAT obsessed with school.”

Harry laughed and fell onto the bed. Hermione huffed and snapped her book shut with a click of her tongue.

“So… we should, um, talk.” She said hesitantly.

Harry nodded and sat up. “Suppose we should.” He sighed and reached for her hand. “Hermione look…if what we did on the train made you uncomfortable in any way, you can tell me. I’ll do what I can to make it right, I just- I never want you to feel as if I’m trying to pressure you into something.”
Hermione shook her head quickly. “No! No it’s not that. I…liked it.” She said with a blush. “I suppose I never expected you to… be interested in me like that.”

Harry furrowed his brow in confusion before it dawned on him. “Hermione how could I not?! You’re- Well you’re bloody stunning!”

Hermione blushed and dipped her head bashfully. “I’m really not…” She whispered.

Harry made to respond but threw away his words. Trying to convince her would take a more…physical touch.

Lunging forward, he pushed the brunette into the mattress. Hermione squeaked in surprise but made no move to fight back. She stared up at him with eyes full of confusion and a little bit of lust. Without missing a beat, Harry reached forward and grabbed the neckline of her shirt. All it took was one tug for the thin material to rip right down the middle, exposing the girl’s firm perky breasts.

Hermione gasped in surprise. She tried to cover herself but Harry batted her hands away and tugged away her pajama bottoms just as quickly. Now completely nude, Hermione stared back at him with eyes alight with excitement.

Harry drank in her body, from her grapefruit-sized breast capped with dark pink nipples to the gentle swell of her hips and smooth, creamy thighs.

“Beautiful.” He muttered, already feeling his co*ck harden at the sight of her.

Hermione smiled wide and bit her lip, her eyes trailing down to the tent forming in his pants. With a twinkle of mischief in her eyes, the bookworm slowly spread her thighs apart once more, giving him full access to her glistening slit.

Harry quickly pulled of his clothes, shucking them around the room in his haste. Before long he was just as naked as the girl before him as she stared enraptured at his co*ck.

“It’s…big.” She muttered dimly.

Harry chuckled. “I’ll take that as a compliment.” Moving, he positioned himself at the entrance of her wet quim, his co*ck head teasing her outer folds gently.

Harry looked to her, seeking permission to continue. Hermione gave it with a nod and steeled herself with a breath.

He took it slowly, piercing her virgin c*nt as gently as possible. Every now and then she’d wince or hiss slightly, prompting him to stop and allow her time to adjust. Once she’d nodded he’d continue on, all the until, he finally bottomed out inside her.

It took all his willpower not to pound her relentlessly right then and there. The feeling of her tight c*nt was unlike anything he felt before. While Gabby’s puss* was tight, Hermione’s was on a whole other level.

After a few moments hilted inside of her, Hermione finally nodded, giving him the go-ahead to finally move. He started slowly, rocking his hips gently against hers. The brunette winced but whispered for him to keep going. He didn’t want to hurt her, but f*ck did she feel amazing. Thankfully, it wasn’t long before her small whimpers of pain morphed into moans of pleasure. Her legs wrapped around his hips, urging him on and Harry wasn’t one to disappoint.

He pulled out, leaving half his co*ck sheathed inside before thrusting his hips forward sharply. Hermione moaned loudly, digging her nails into the soft mattress beneath them for support. Her wet c*nt gripped him snugly, but Harry’s thrusts were soon brutally spearing her constrictive walls with ease.

“OH GOD! YES HARRY!” Hermione wailed. Her hands moved up and she began to paw at her own tit*, pinching her nipples hard as he f*cked her. “OH PLEASE PLEASE PLEASE! DON'T STOP!”
Harry grunted. He had no intention to do so. Her puss* was like heaven . Her velvety walls trembling around him practically begged him to keep going, trying desperately to milk his seed. Merlin it was phenomenal. If he ever told Gabby the truth of the magical world the first thing he’d do is show her the memory of this exact moment. Seeing him ruin Hermione’s tight c*nt would drive the raven-haired slu*t wild with lust. Just the thought of Gabby and Hermione in the same room led to all sorts of depraved and kinky fantasies.

Perhaps that wasn’t such a bad idea either…

“OH! OH GOD! I’M- GYAHHHH!” Hermione screamed. Her back arched, mouth agape in an ear-shattering scream as the brunette came hard. She thrashed against him as her climax tore through her thin frame. Harry groaned as her puss* constricted around his co*ck. He couldn’t hold back any longer. With a final thrust inside her slick depths, Harry erupted, sending jets of white hot cum deep inside her womb.

They stayed together, joined at the hips while their respective org*sms cooled. Harry stared at the picturesque scene before him. His best friend glistened with sweat. Her bare breasts rising and falling with each harried breath and her c*nt pierced by his co*ck.

Harry could get used to such a sight.

Author’s Note

First (official) chapter down! Keep an eye out for the next!

Thanks for reading!

Harry's Bucket List - Chapter 2 - Flight_OfFancy - Harry Potter (2024)

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