Caught by the Right Person (Patreon)

AN: It was interesting watching this poll, because at the start it was pretty close. I wasn't sure which option had the edge and figured it would come down to the extra votes for higher tier patrons. Then from the eighty-vote mark on most the votes went to this prompt and turned it into a runaway. 

Anyway, enough of my random musings, here's the story!

Casting:

Penelope- Marina Laswick 

Walking through the empty, quiet halls of Hogwarts, Penelope Clearwater’s, Penny to her friends, steps echoed against the stone. It was late, very late, well-past curfew and even the paintings were sleeping. But it was her turn to patrol, and it wasn’t a night that she was happy about that fact. As Head Girl, she had some say in the scheduling of the prefect patrols so, one might consider it odd that she’d allowed herself to be on patrol on Valentine’s night.

She was meant to be patrolling with her boyfriend, Percy Weasley, but instead she was alone. She’d insisted on it… vehemently... after the morning she’d suffered. Oblivious, thoughtless, insensitive prat! Not a single flower, nor chocolate, nor any other sign that he’d given a passing thought to the day.

When she’d confronted him about it, he’d had the gall to tell her, “It’s our NEWT year, Penelope,” in that obnoxiously snobbish way of his, “there are more important things to worry about than… Valentine’s Day. No wonder you’re only second in our year.”

So, it was accurate to say that Percy was now Penny’s ex-boyfriend. What I ever saw in him in the first place, I have no bloody idea! Hearing rustling and a soft giggle from a nearby room, Penny turned and sighed. This really is the worst night to patrol.

It should’ve been brilliant, she had plans of her own after all. But those had fallen through terribly. And now it felt live every time she turned the corner, she found herself opening the door to another broom closet or unused room of the castle to find more couples… celebrating the day. Most of them were in some state of undress kissing, or sucking, or even outright fucking each other. Though it’d been a while since the last encounter, and she was hoping it was late enough now that this would be the last.

Every one of them should have counted themselves lucky that they were caught by her and not by either Percy or Filch. Pretty sure Percy is trying to find a way to get his own tiny cock in his ass, because there’s no one else he’s infatuated enough with to fuck… except maybe the Minister.  And Filch is probably rutting Mrs. Norris.  So, now it was left to Penny to stumble upon seemingly every horny couple in the entire castle with frustrating frequency.

Opening the door with a bang, Penny startled the occupants of the room. They both jumped and tried covering up before she even said anything. It was Fred Weasley and Angelina Johnson. Looking down at the younger ginger’s crotch, she couldn’t help but note that he was bigger than his brother. His cock was slick with Angelina’s spittle as he shoved it back into his trousers with some effort.

The sight of it sent a pulse of need right to her pussy. It had been the way of things all night. She’d spent weeks hot and bothered with nothing to satisfy her needs but her own fingers and imagination. Percy certainly wasn’t going to take care of it. She’d meant to change that fact that night, but no, instead she was forced to encounter dozens of horny students only growing randier with each encounter and no way of satisfying that itch.

Glaring at the pair, Penny was doing everything in her power not to let them see her distraction, “Get dressed and get back to your dorms. If I find you out again tonight, you’ll be in detention until the end of term.” There was part of her that wanted to punish Percy’s brother horribly, but she knew that wouldn’t be fair to either him or Angelina. Especially considering I had every intention of doing much the same tonight.

“That’s it? No punishment?” Fred asked her. zipping up his trousers. Angelina smacked him on the shoulder as Penny sent him a look that could freeze water.

“No,” she bit out, “unless you have problem with that.”

“No, no definitely not,” Angelina rushed to say, walking toward the door, “Thank you, Penelope. This won’t happen again.” She said the last looking at a sheepish looking Fred. The pair hurried out of the room, muttering among themselves.

Watching them go, Penny shook her head as Fred reached down and pinched his partner’s bum. Don’t think Percy ever did that even once to me. She couldn’t help but replay her entire failed relationship in her mind, complete with miserable final day.

Suddenly, it all just became too much as her wand came into her hand. Screaming, she fired spell after spell into the wall trying to work out some of the tension that had just built and built through the hours, and days and months of dissatisfaction that all just culminated in this miserable patrol.

The stone wall of the room withstood her onslaught well, just a couple of chips breaking free when she finally finished. Gasping heavily, Penny took in great shuddering breaths of air as tears came unbidden to her eye. They weren’t tears for her broken relationship with Percy, she wouldn’t cry over that prat. The emotion of it all just hit her, and she couldn’t keep it at bay. And then she whined low in her throat as she couldn’t ignore that there was still a horrible, unbearable itch deep in her pussy.

Looking around the empty room desperately, she shook her head muttering to herself, “Oh fuck it!” She knew there was a risk she could be caught, but she also knew better than most that without her out patrolling the corridors, it was highly unlikely.

Dropping her robes from her shoulders, she fell to the floor and sat her bum on the discarded garment. The thick black material far softer than the stone. Resting her back against a desk at the front of the room, she spread her slim legs so that the cool air brushed against the damp, soaked knickers between her legs. It made her shiver involuntarily. She was wearing the sexiest pieces of lingerie she owned. A deep, sapphire blue set of satin and lace garments, they were delicate and thin and she’d been wearing them all day since before her falling out with her boyfriend. It was meant to be a surprise.

As her fingers skimmed down her sides to find the sticky gusset of her panties as they clung to her sex, she wasn’t giving Percy a single thought though. No, her sole thought was on giving her desperate sex the attention it needed as she plunged her digits into her own depths. As the seconds ticked by, her intense focus only heightened. Had she been aware of anything but her own need, she might have noticed the door opening and closing quietly.

---------------------------------------------------------------------------------------------

The Marauders’ Map and was in Harry’s hand and he was invisible beneath his father’s cloak as he explored the castle a bit aimlessly. It was late and given that, unlike when he usually broke curfew, he had no reason to be out, he really should be in bed. But then he never should have gone down to retrieve the Philosopher’s Stone or to fight a basilisk on his own… and he did that without hesitation. So, why would he hesitate to do a bit of late-night exploration? I couldn’t sleep anyway, might as well do something useful with my time.

Filch and the prefects were nowhere to be seen from what the map was telling him, and most of the couples who wanted to celebrate Valentine’s Day had either been caught and sent back to their dorms or managed to get away with it and made their way back of their own accord. It is properly late now, after all. Nearly one in the morning.

Harry stopped as he heard a scream somewhere on the floor below him. Looking at the map, he could see three little dots, one each for Fred, Angelina, and Penelope. Two of those dots were hurrying away from a room, where the third remained.

Curious as ever, Harry started down the corridor he was in toward the enchanted staircase. As he descended to the floor below, he noticed Angelina and Fred heading toward him, both of them looking a bit frightened. He was forced to press his back to the railing as they passed to avoid running right into them.

“I tell you if looks could kill…” He heard Fred mutter.

“Just be glad she waited until after we left to start throwing spells,” Angelina replied, grabbing her boyfriend’s hand to pull him along faster, “Not sure why your brother would want to piss off a witch like that.”

“He’s always been a git.”

Padding down the stairs, Harry headed in the other direction of the couple and found himself outside of the room in question. Looking down at the map, he found that Penny was still alone inside. Concerned as well as curious now, Harry tried the door to find that it wasn’t locked. If she throws too many spells, she’ll suffer magical exhaustion with no one there to help her.

Opening it quietly, he stepped inside. What he found stopped him dead in his tracks. Sitting on the ground, legs splayed out obscenely, hand between her thighs was the Head Girl. Her thighs were encased in black, thigh-high stockings while her blouse was pulled open haphazardly revealing a hint of the deep-blue garment beneath. Harry had never seen anything so incredibly enticing… so consumingly sexy in his entire life.

Penny was a beautiful young woman with dirty-blonde hair that hung loose and wavy down to her mid-back. She had an oval face, with a straight, narrow nose and full lips. She bit her lower lip between straight, white teeth as she pleasured herself. Her breasts were small and perky, just smaller than a handful if Harry were to guess. Honestly, everything about her was small, or compact might be a better way of putting it because she was still every bit a woman. How the fuck did Percy ever pull a girl like that?

The sight in front of him sent hot need straight to his cock, and he could feel himself hardening within his trousers. He couldn’t take his eyes off her as his hand instinctually went to his now very-prominent bulge. There was a lewd wet sound as Penny’s hand moved ever faster beneath her upturned skirt.

Desperately in need of a better view, Harry stepped into the room quietly as a church mouse. Much as he knew he was being a voyeur, he had absolutely no desire to see the show stopped. Standing in front of her now, Harry was treated to the sight of her gorgeous pink pussy, it was dripping and bare and he had to fight off the groan that wanted to escape his lips, lest he be heard.

Cautiously and deliberately, Harry’s hands slipped beneath the waist of his trousers and pants to find his warm, waiting cock beneath. Every nerve in his cock felt like it was on fire in a way that he’d never experienced before. The muscles of his neck tightened as he fought off another noise that threatened to escape him.

Penny wasn’t being nearly as circumspect in her self-censure. A throaty, ridiculously wanton moan echoed in the empty room that went straight to Harry’s bollocks. He watched, fascinated as her pink pussy pulsed around her fingers, urgently squeezing at the digits as her arm shook erratically. Her deep, nickel-grey eyes fluttered shut as she shuddered.

He was watching a woman cum for the first time in his entire life and loving every second of it. The one didn’t seem to be enough for her though, as without a moment’s hesitation, she went right back to touching herself.

Freeing his cock from its confines, he was shocked at the sheer amount of precum that stained his pants and dripped from the angry, bulbous purple crown. He’d never felt so horny, so needy, in his entire life. When he fisted his length, ready to join Penny in her self-satisfaction he lost all sense of self, and a moan slipped from his lips.

Immediately, his gaze dropped to the older Ravenclaw in front of him and found her eyes looking right at the spot where he stood invisible. Her small hand covered her even smaller pussy as she spoke, “Who’s there?” Her voice was sweet and breathy as she reached shakily for her wand where it lay above her on the desk, “I… I know someone’s there. Show yourself or I’ll start throwing curses.”

-------------------------------------------------------------------------------------------

Her larch wand shook slightly in her hand, but she steadied herself, unwilling to let her voyeur see even the faintest hint of uncertainty. Even in her post-orgasmic state, she knew exactly what she’d heard. A moan, a man’s moan at that, deep and eager no more than a few feet from her.

Her wand did not waver from that spot, and she heard nothing more. For a brief moment, she did question herself, but then she heard a sigh before a disembodied head appeared just in front of her. Her eyes-widened in a way she imagined was probably comical. Well, that’s certainly not who I was expecting.

“Harry?” In her surprise, she lowered her wand with one hand and uncovered her dripping slit with the other, she noticed those emerald eyes glancing down in obvious interest. Despite being older than him, even she was aware he had the most beautiful eyes in the school.

“Hello,” she could tell that he was nervous by the way that he seemed to be rocking back and forth on his feet. As well he should, naughty little fucking pervert. She wasn’t nearly as upset by that fact as she probably should

“What do you think you’re doing?” It looked ridiculous to her, just watching his head float there, “And get out from under that invisibility cloak you’re clearly wearing!” No wonder he’s always had such a talent for avoiding getting caught when he wants to.

“I uh… I don’t think that’s a good idea.” He told her, his cheeks going a bright ruby-red in his embarrassment.

“I don’t care! Either take it off and explain yourself or I’m taking you straight to McGonagall.” It was an empty threat. Given what he’d found her doing, it was mutually assured destruction if she told anyone else about his little peeping excursion. However, fear of their Transfiguration Professor seemed to do the trick as he dropped the liquid-like material of the invisibility cloak to reveal his entire body. And she did mean his entire body.

Penny’s eyes were drawn straight to his turgid length and the sight of it sent a jolt right to her horny womanhood. Merlin and Morgana! He’s bigger than Percy by half and thicker too. Swallowing thickly, she looked from his impressive appendage up to his face where he was refusing to meet her eye. Calmly and kindly as not to spook him any further, she spoke, “So, what were you doing?”

“I heard screaming and spellfire… I came to make sure everything was alright.” He told her, fear obvious in his eyes.

“Not the sort to just leave a situation alone are you,” she smiled at him, trying to put him more at ease, “A proper Gryffindor who will run straight to spells when he hears them.”

“I suppose.” His blush deepened at her words.

“Look at me, Harry.” He’d still been trying not to, but she wasn’t having any of it. Penny still had her legs spread and her tiny pussy on display… and that was the first place his eyes went. This was an opportunity as far as she was concerned, one that she had full intention of taking advantage of, “Good, so you came to… help me… thanks for that. And you found me here alone, playing with myself and thought you might as well do the same.”

“No…”

“Really, because I think your cock says otherwise.” Despite the situation his manhood still jutted out proudly from his body, “Now, I’d say I put on quite the show for you.” She looked at him pointedly and got a nod of his head in return, “Good, I think it’s only fair that you do the same for me.”

“What?” His eyes widened in shock at her suggestion.

Beaming up at him in response, she dipped one hand down to her slit, “You heard me. I want you to stroke that big cock of yours until you cum.” This was certainly the most wanton thing Penny had ever done in her life and she loved every second of it.

For a moment, he looked like he might refuse, but then she watched as his neck flushed and he took a hold of his cock with a groan. A bead of crystal-clear precum leaked from the tip and spilled to the floor. Penny dropped her hand to her honeypot and started rubbing her lips in small circles as she watched him enthralled.

As his breathing quickened, it quickly became apparent that he wasn’t going to last long. Perfect. Means we can get to the main event sooner rather than later. She knew that he was likely inexperienced and getting that first load out would make him more likely to last when she had him slide that fat cock into her. It’s going to stretch me so wonderfully.

When he closed his eyes as he climbed closer to his peak, she clicked her tongue drawing his gaze back to her, “No, keep those… beautiful eyes on me, Harry. I want to see the need in your eyes when you explode.” Quickening her own pace, she deliberately kept herself just on the edge, fingers briefly massaging her engorged clit. She wanted her next orgasm to come with him buried as deep as he could go into her tiny tunnel. I wonder if he’ll even fit all the way in my tiny little pussy.

As he stared, she whimpered and moaned. The sights and sounds proved too much for him, and she watched as the vibrant blue veins pulsed and thickened as his cum rocketed up his shaft and out his cock-slit.

It didn’t matter that he stood a good meter away from her, he still managed to cover her with his deliciously warm, thick seed. The first shot landed on her face, and she licked it from her lips savoring the salty treat. The next landed on her chest followed by another and another that covered her legs. She was shocked by the sheer volume of it and watched as the last of it dribbled out of his cock to stain the floor at his feet.

It took a great deal of effort not to cum right along with him, but she managed. Standing, she pulled her blouse the rest of the way off and dropped her skirt, her slim thighs allowing it to pool at her feet, “Thank you, Harry. I’d say we’re even now.”

She was happy to see that his eyes were fixated on her. She knew she was on the slimmer side and that some boys preferred a woman with a bit more meat on her bones. It doesn’t seem like that will be a problem. Despite the incredible load he’d just unleashed from his cock, he was still rock hard. Gods bless his fucking stamina.

Leaning back against the desk behind her she spread her legs wide and stretched her taught pussy lips apart with two fingers, “If you want… there’s one more thing that you could do for me. If you’re interested in getting into a bit more… trouble anyway.”

Without a word, he stepped between her legs and pushed against her shoulder, forcing her back against the unforgiving wood of the desk, she gasped and reached down for his length. It was slick and slippery with his own cum, “Hmmm… that’s the idea... good boy.” She placed his cock at her entrance and whimpered and split her engorged, puffy lips around the wide crown.

“Bloody hell…” His voice was breathy and eager and everything she wanted to hear from a lover ready to sink his length into her body.

Looking up at him through hooded eyes, she entwined their fingers together, “You don’t have to be gentle, Harry. I’m so fucking wet…” She lost whatever else she thought to say as he drove all sense from her mind.

Driving his hips forward in one smooth even thrust, her mouth opened in silent joy as pleasure shot through her body. She couldn’t remember anything feeling this incredible. Her sex was leaking juices onto his digging length as he slid his way deeper than anyone anything had ever gone before. Her eyes rolled toward the back of her head as her hand went to her clit. She couldn’t help but wonder why she’d wasted her time with Percy if there was a cock like this in Hogwarts.

He fit snugly in her sheath, his balls coming to rest against her bum just as the head of his cock tapped at the entrance to her womb, “You’re a… perfect fit.” Her hand was shaky as she rested her hand on her belly where she could feel him. She was teetering on the edge from her earlier ministrations and knew that it wouldn’t take long for him to pull a climax from her body, “Now... fuck me.”

Not needing to be told twice, he pulled his hips back a bit jerkily. This is his first time, I’m sure. There’ll be plenty of time to get his technique right in the future, though. For now, the sheer size of his appendage was enough regardless of skill. It scraped against parts of her pussy that’d never been touched as he left her before he snapped his hips forward, burying himself back inside of her heat. His bollocks slapped heavily against her bum and the lewd smack that echoed in the room was music to her ears.

Her body shook, her perky tits shaking on her chest as she reached her peak from that single wonderful thrust. Her pussy clamped down around his pillar of hard flesh as he tried to retreat again, but she’d become too tight. Her juices squirted out from where they were joined, covering his lower abdomen and her stockings, “Oh… fuck…YES!”

Grabbing her hips in one hand and her shoulder with the other, he wrenched his cock out of her body despite the strength of her gripping tunnel and it made her eyes bug out in wonderful bliss. When just his knob remained in her tunnel, he thrust back into her body ferociously.

Smack. Smack. Smack. Penny could only stare up at him in wide-eyed awe as he started using her body like his own personal pleasure doll, “Yes… absolutely fucking destroy me… baby!” His movements were clearly inexperienced, but he developed his own rhythm quickly enough, and it felt wonderful regardless, particularly after her prolonged dry spell.

He managed to fuck her through another orgasm before she could see the tell-tale signs that he was nearing his end, “Harry… you need to pull-out… I want you… to cum… all over me…” He didn’t seem to hear her at first, too focused chasing his own pleasure.

Her fingers pressed against his hip as she felt him swell in her pussy. With what seemed like tremendous effort, he pulled his cock free of her tunnel with an obscene squelch. She reached one hand down to jerk his sex-slick manhood. Throwing his head back from the pleasure, she felt him swell in her grip as his cock started covering her from her pussy mound all the way up to her neck. Shot after shot covered her torso, his seed filling up her bellybutton. After his first load, she couldn’t believe that he had so much left.

If there had been any doubt in her mind that this wouldn’t be their last time together, which considering her earlier musings was unlikely, he completely removed them. Giggling at the remarkable young man’s efforts, she scooped a bit of his seed up into her mouth, “Thanks, Harry, you have no idea how badly I needed that.”

“Happy to help. I’m just glad I was the one who caught you.” he told her, sweat dripping from his brow. It was a very sexy sight, and if it weren’t for how sore her abused little pussy felt, she might see if he was up for another round.

“I think you’ll find it was me that caught you… when you were under that invisibility cloak.” She retorted as he offered her a hand up which she took gladly.

Grabbing her wand, she cleaned herself and him. She would have preferred to suck him clean but knew where that was likely to lead. With another wave of her wand a piece of parchment appeared.

Harry rose one eyebrow in question as she handed it to him, “It’s a copy of my patrol schedule, you know… just in case you’d like to be caught out after curfew again some time.” The bright, beaming grin she got in return promised enjoyable nights to come.

AN: As always, thanks for reading! Hope you enjoyed!