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Regrettable

Summary:

After over a decade, Hermione must come to terms with the fact that the first thing she’s ever truly failed at was her marriage, especially when her former co-head of house decides to slither back into her life. Dissatisfied in his own marriage, Draco seeks to bring Hermione to heights of pleasure she never knew possible, discovering his dark side and her need to submit along the way.

Adultery, deceit, divorce, scandal. Hermione Granger-Weasley and Draco Malfoy watch their worlds crumble around them and cling to each other for solace. But, will their torrid and kink-filled love affair give them the happy ending they never thought they’d find, or will it turn out to be an affair most REGRETTABLE?

Notes:

Hi there! Another Dramione WIP? Don't mind if I do! So, I've been holding off on posting this one for a long time, but now that I've found a great deal of inspiration, I just couldn't resist!

Today in particular I'll be posting two chapters because the prologue shouldn't really count, right? Tags will be updated as needed as each new chapter is posted, so check them frequently. For now, I'll be adding all tags for chapters that are written, so that you know what you're getting into!

Please do me a favor and don't read this if you're just going to comment how "out of character" Hermione is being. Its a story about her super kinky extramarital affair with Draco Malfoy. If that's not OOC Idk what is. Its just for fun and smut!

As always, PLEASE PLEASE PLEASE let me know what you think! What did you love? What did you hate? What do you hope to see in future chapters? There's so much of this story that is yet unwritten, so I want to hear from you!

Chapter 1: Prologue

Summary:

Hermione Granger and Draco Malfoy share an alcohol-fueled night of passion after the last of their N.E.W.T.s, which will prove to be a lasting memory for both parties.

Chapter tags: Consensual Drunk Sex, Sex, Anal Sex, Oral Sex, Anal Fingering

Chapter Text

Regrettable-Banner

He’d never seen Granger drunk before. He’d never seen her go to a party, or let loose in any way, actually. It was one week before graduation, the exams had all been finished, and most of the seventh years had gotten together to plan a party. It was the biggest party of the year. Hell, it was the biggest party he’d ever attended at Hogwarts. It wasn’t all that surprising after everything the students had been through in recent years. They were tired of mourning, and they were ready to celebrate. For the first time in their study at Hogwarts, Voldemort had not spoiled their year.

As Head Boy and Girl, they were not only in attendance, but they were asked (by the Headmistress, who was far too omniscient to not know such an event was being planned in her school) to keep the shenanigans from getting out of hand. Still Draco never could have guessed that he’d be the one dragging a properly intoxicated Hermione Granger away from the festivities and back to their dorms. She had a reputation to maintain, and he knew that if she kept going at her current rate, no one would respect her in the morning.

“You,” Hermione said to him as he escorted her down the corridor close to midnight, pointing her finger at him threateningly. “Are a party pooper!” She punctuated the last two words with a wiggle of that finger.

Draco could barely contain his amusement. “And you were about five minutes away from losing your dress,” he informed her. “You can hate me in the morning.” He wasn’t mad about leaving the party early. Perhaps in years past he would have been, but tonight was her night. He knew how stressed she was about what to do with her life after graduation. Which path to take. It must have been so hard, having so many doors open that you don’t know which to go through first.

Hermione laughed loudly, her voice carrying through the empty corridor. “I bet you would have paid to see that,” she said, as though she was talking about someone other than herself.

“You’re damn right,” Draco agreed, smirking over at her as they walked. “But if I’m going to see what you’ve got going on under all that, I’m going to want a private show.” So perhaps Draco Malfoy had had a lot to drink that night as well, but he handled himself a lot better, given his higher tolerance.

“Malfoy!” The head girl chastised, taking a double step to the side as she nearly lost her footing.

Draco watched her stumble and moved closer to her, in case she decided to lose her balance completely. “Hey, don’t act so innocent, Granger,” he slurred slightly. “You have been teasing me all year long.”

“Oh I have not,” Hermione dismissed, her ankle twisting slightly with her next step. She winced and stopped briefly. “My heel is broken,” she complained.

Draco watched as she kicked her foot out, and the apparently broken pump spiraled through the air, toe over heel over toe again, before landing with a loud clatter on the stone floor several meters ahead of them. And then she was laughing, more than laughing, she was roaring, stumbling into the wall and letting it hold her as the mirth washed over her at the unexpected result. He laughed as well, at her as much as with her. If it hadn’t been broken before, it certainly was now.

"Alright, drunky drunk, let's get you home." Draco moved to get her away from the wall and back on course towards their living quarters, but she pulled away from him stubbornly, and wrenched the other high heel from her foot, leveling herself out. He picked up the discarded footwear and mended the two pieces back together with his wand.

Hermione hadn't been ready to leave the party. It was so much fun! Everyone was drinking fire whiskey and dancing, playing games, snogging… Not for the first time she'd regretted that she had a long distance relationship. She wanted to be the girl snogging her boyfriend in a corner!

But Ron Weasley was off with Harry and Neville and whoever else felt they hadn't already seen enough action for their lifetime. She was proud of him, but she wished he'd finished his education first. Both of them. Instead she'd returned to Hogwarts without them, and made an unlikely friend in her Head partner Draco Malfoy, of all people.

"Maybe I don't want to go home," Hermione contradicted just to do so, swinging her lonely shoe in her hand as she walked. Somehow she was no better at it without the heels. "Maybe I want to stay out all night. Maybe I want to do something-"

Whatever kind of thing she'd been about to suggest Draco would never know, because they had reached a staircase, and hardly three steps up Hermione had tripped and skidded back to the ground on her bottom. She didn't laugh this time. Instead she looked up at Draco with a pout. "Ow. That hurt quite a lot, actually."

Draco trotted down the few stairs between them. "Alright you." He helped her onto her feet. "Don't make me levitate you."

"You wouldn't dare," Hermione dismissed with a laugh, wiping any potential dirt from her rear.

"Oh? I wouldn't?" He knew it wasn't wise to drink and cast, but it was just a beginner levitation spell. It was literally the oldest trick in the book. He drew out his wand. "Wingardium leviosa," he articulated clearly, as to not humiliate himself by screwing up the simplest spell on earth.

Hermione cried out in protest as she began to float. "Draco Malfoy you royal pain in my arse, let me down!" She demanded, but as she looked down, she realized that she was floating above the ever shifting hall of stairs, and her determination faltered. Draco was beside her every step of the way.

"You sure about that?" He asked her knowingly.

"N- no…" Hermione remained gratefully silent until they got to the third floor. "Alright you can put me down now. I can bloody walk." She didn't care to be humiliated further.

"If you say so," Draco agreed this time, and lowered her nearly to the floor before ending the spell. She fell the final few inches as gravity reclaimed her, and nearly toppled over. "I thought you said you could walk. You can barely stick a three inch landing," he criticized her with amusement, walking past her towards their dwellings.

"Oh shut up. I may be drunk but I'm still an independent woman." As she started to chase after him, she dropped her shoe.

Draco turned when he heard the item hit the floor. "Bloody hell, women." He walked over to her and picked up the shoe, holding it up with its twin for her to take. When she reached to take the pair from him, he yanked them back, and instead wrapped one arm around her waist. "Someone's forgotten her manners tonight."

She swayed where she stood, supported by him, looking up at him in surprise. He was touching her. Actually touching her. She was sure it was a first. The small of her back where his hand rested felt warm. She recognized a tingling sensation in a place that hadn't had reason to tingle for a very long time. It was almost electric.

"May I have my shoes back?" She asked him sweetly. "Please?"

Draco looked down at her, and in his mildly inebriated state he found himself tempted by her. It wouldn't be the first time he'd had such thoughts about her. He'd had them for years, visions of arguing themselves into a passionate snog, sometimes more. But he'd never been presented with such an opportunity. She was in fact looking incredibly kissable. And on top of that, she was well within kissing range.

Screw it.

Their lips met so suddenly that Hermione realized that he must have kissed her at the same moment she'd leaned up to kiss him. Her soft hands cupped his neck on either side, fingertips slipping into the silky blond hair on the back of his head. His kiss was hungry, and she failed to contain a moan. It felt good.

Draco took hold of the narrowest part of her waist, pleased that he hadn't been slapped for his advance. A moment later he had her against the wall, leaning one arm into that stone while his other hand cupped her cheek possessively. Her passionate response threw him, but he loved it. He let his mouth claim dominance over hers, and heard her moan into him once again. He could sense himself becoming excited, a stirring that he knew was a very, very bad thing in this moment, with this girl. He stepped away from her quickly, as though her lips had scorched him.

"Go to bed," he ordered her, a warning she didn't seem to comprehend, as he held her shoes out to him at arm’s length. They were only steps away now from the side by side doors that separated the newly installed Head Boy and Head Girl dwellings.

Hermione pouted.

"Now," Draco insisted.

She pushed away from the wall and retrieved her footwear, and traveled the small space to their doors, but instead of entering her own room, Hermione spoke his password and disappeared behind his door. Draco chased after her. "I meant your bed!"

Her shoes had been dropped near the door, and a few feet away he found, much to his astonishment, Hermione's little black dress. He knew she’d been close to losing it. "I mean it Granger. Don't start something, because I'm not a nice guy. I will finish it." She was standing halfway between him and his bedroom, walking backwards as she unhooked her bra. Draco watched as it fell to the floor as well. Her newly revealed breasts were just what he thought they'd be, somewhat small, but perky and round. For their size they appeared firm and full. He wanted quite badly to find out for himself.

Hermione let him stare at her a moment longer. It was fun, the look on his face, the way he warred with himself over whether or not to take advantage of poor drunk Hermione Granger. Only Hermione had already made up her mind. Tonight was going to be the night she did everything she wasn't supposed to. And going to bed with Draco Malfoy had moved to the top of that list the moment they'd kissed. He was going to ensure that she would never be that poor prudish girl who only knew one man for her all of her days.

She turned and walked into his room. A moment later her thong underwear came flying out the door.

Draco watched the unusually lewd behavior in shock. Somewhere just inside his bedroom was a very drunk, very naked Hermione Granger. And he was just drunk enough to not feel like a predator as he followed after her.

He found her seated on the edge of his bed, cross-legged, leaning back on her hands with her tantalizing chest jutted out in his direction. Draco had long since realized that she had grown to be a very attractive young woman. What he'd never realized was just how sexy she was. Her stare was daring, and she bit her lip seductively. He was no damn fool. He couldn't let this opportunity slip away.

“You said you wanted a private show.”

The pounding of Hermione's heart echoed loudly in her fuddled head. He'd promised her he'd finish it, and Merlin did she hope he meant that, because she didn't think she could bear the humiliation of being rejected by a womanizer like Draco Malfoy. When he entered the room and found her, he looked as though he wanted to do horrible, dirty things to her. She wanted him to, too.

She watched as he began to undress before her, his fingers working his cuff-links and discarding them on the dresser behind him while simultaneously stepping out of his shiny black shoes. He disposed of his dress shirt as quickly as he could, revealing a hard, narrow torso. He was tall and lean, but strong looking, his body shaped by a physically active lifestyle, not built upon forcefully through weight lifting. Even his lengthy arms were defined, and she wondered how he might use them on her tonight.

He was working his belt now, and made show of removing the entire leather piece from its loops. Hermione squirmed where she sat, the heat between her legs aching in anticipation. Her eyes were locked on his hands, which were unfastening his trousers at an agonizing pace. Her lips parted slightly as they were pushed down his hips, the tiniest gasp of air escaping her, and he was free, as naked and vulnerable as her.

He captured her face in his hands, her lips with his own. It was raw, thoughtless passion that made goose pimples rise on her skin even though the room was sufficiently warm. One of her arms wrapped around his neck, the other still behind her she moved further up the bed, pulling him with her. When finally her head hit the pillow she broke away with a large intake of much needed oxygen.

As soon as their lips parted Draco kissed his way down to those beautiful tits she'd displayed so proudly for him. He spoiled them with touch, feathery kisses, and sucked each peak into his mouth in turn with a moan. Her back arched into his treatment.

"Oh yes…" Hermione whispered in approval, threading the fingers of one hand into his hair, the other into her own. He ran his tongue up the valley between both hills, and down again, traveling south to worship other parts of her.

She spread her legs to receive him, and Draco held her thighs apart to look at her petite pink cunt. He looked forward to tasting it. Still holding her open, he used his thumbs to spread her lips to find her shiny with the slick from her excitement, and ran his tongue up the length of the sweet treasure.

Hermione moaned and writhed underneath him. Her fingers pawing at his scalp while he devoured her. She hadn't experienced anything quite like it. It didn't seem like he found it obligatory at all. He was enjoying himself! That fact alone was a significant turn-on. After he sucked hard on her clit with his nose pressed into the small patch of hair she allowed to remain there, causing her legs to spasm out of her control, Hermione pulled him up by his hair.

"Are you going to shag me or what?" She asked him breathlessly.

The responding smirk was feral, and he climbed back up her body, kissing her passionately as he thrust into her sopping wet core. It took four tries in total for her tightness to accept his full length, stretching her like she hadn't been stretched in many many months. She wrapped her legs around him and mewled like a cat in heat against his lips. Her arms went around him as well, fingertips digging into his back.

He wasn't gentle, and Hermione loved that. She'd made love to her boyfriend during the summer, but she'd never been good and fucked, and that was what her alcohol infused body craved so badly. After a few minutes he rose to a sitting position, smirked down at her, and ordered her turn over onto her stomach. She was already panting and sweating despite the fact that she wasn't doing anything more than receiving him, and at his command she turned, moving onto her knees but keeping her upper half lowered to the mattress.

His hands were on her hips, and a moment later she cried out, caught off guard by how intense this new position proved, how deep it put him inside of her. "Oh, yes, Merlin yes!" Hermione praised his efforts. Her whole body rocked with each forceful thrust. She was lightheaded and giddy, so much so that she chuckled between moans and gasps. She was sure she'd had at least two or three orgasms, but she couldn't think straight to keep count.

"More!" Hermione cried out after several minutes of taking the brutal impact of the change in position. Draco knew she was loving it, he was loving it too. He'd felt her walls clamping down on him violently, heard the unmistakable sounds of ecstasy that poured out of her, and the visual of his own cock moving in and out of her was to be his new favorite memory. "I want more! Fuck me harder! Don't hold back!"

He wasn't sure if he should. Her body's repeated attempts to send him spiraling over the edge were nearly winning. He didn't know how much longer he could last. He usually had so much more stamina.

But she was asking so nicely…

Thinking of how he could intensify this moment, Draco slowed, spread her cheeks, and aimed a modest gathering of saliva to fall gently just above her unoccupied opening. With a well manicured finger, he pressed the slick fluid into that opening, swirling and teasing it until his finger began to dip inside.

"Oh God," Hermione groaned. "Yes! Do it. Do anything!" Never in a million years would she have expected to actually agree to any sort of anal play, but if this was his idea of "more" maybe he knew what he was doing?

Draco wished his wand was within arm's reach. He reached behind him, casting a silent, wordless summoning charm. The wand soaring into his open hand surprised him, and he nearly dropped it. He hasn't expected that to work. Now armed, Draco summoned again, this time calling forth a small bottle from his bedside table. He tugged the cork off with his teeth, and poured a small amount of the sweet smelling liquid into the hole with his finger, which moved in and out of her in a twisting motion. More liquid, and a second finger, stretching the orifice as it’d never known.

This was crazy. It was absolutely crazy. It was all Hermione could think as she felt his cock moving inside of her, his fingers gaping her. A few moments after a third finger was added to her backside Hermione came loudly, toes curling as she clawed at the bedding. “Just do it already! I want to feel it!” she whimpered. She’d never do this again, she was absolutely sure of it. And she’d never consider letting Ron do anything like this to her. He’d never respect her again. But Malfoy barely respected her to begin with, so what was the risk?

Draco chuckled, and removed his fingers, taking another moment to slam himself into her at a furious pace, before slowing gradually and withdrawing. He pressed himself instead to the newly prepared hole. He poured more of the lubricant and spread it over his shaft, before carefully pushing in.

Hermione’s head was spinning, and the butterflies in her stomach were almost nauseating. She willed herself to relax to the intrusion. She’d consented to this. She’d asked for this. She could feel just the engorged head inside of her now, and he was pressing forward still, millimetre by millimetre, in and out. Each time he moved forward he fit more of himself inside of her. Hermione grew impatient. The stretching was bearable, and she suspected the lubricant had something to do with that. A numbing agent, if she had to guess. Finally, after what felt like for too many minutes, he was inside of her. She could feel his pelvis pressed firmly against her, indicating that he was fully submerged in her willing arse.

“Fuck, Granger…” Draco groaned as though he was complaining, when really it was praise. “It’s so tight. Fuck, you feel so good…” He moved in her steadily, his pace picking up speed as her muscles relaxed and accepted him.

“It’s good,” Hermione agreed, not hating the way it felt. In fact, it was possibly the most intense thing she’d ever felt, and the faster he moved, the more intense it grew still. She could feel that he was still holding back, though, and while she appreciated the care, she felt after several minutes that she had properly adjusted to the sensation. “Oh shite, Malfoy, please, more. Harder,” she whined. “Fuck me!” If she was going to commit a sin this regrettable, she didn’t want him to hold back one bit.