VIII

Dean's thick fingers were delicate and stable over Cassandra's hair as he brushed it back, gathering everything and making a high ponytail, before wrapping it with a hot pink scrunchie.

"Gorgeous little thing," he mumbled to himself, looking down on her. "You're going to be a treat for Sammy, won't you, princess?"

She just giggled, eyeing the pair of cheap pom-poms he'd bought along with a little - very little and very slutty - cheerleader costume.

"Sammy?" she repeated, giddy and a little cheeky.

Dean raised an eyebrow as she turned to face him.

"He's my little brother, princess," he tapped her on the nose with a single finger. "I get to call him that. It's professor Samuel to you."

She smiled.

"Professor Sammy," Cassie said in a teasing tone, giggling more.

Her boyfriend shook his head, reaching for her and adjusting the sleeveless top on her shoulders.

"Are you wearing anything under that?" he asked, fingertips skimming down her collarbones to her breasts.

She wasn't. Cassandra's outfit was composed simply by a little skirt that barely covered her ass and the back of her thighs, and a top that was a little thin and showed her nipples to anyone who would look.

"I thought you liked looking at my tits, coach," she teased him.

Dean licked his lips.

"So you decided to flash the whole school?" he raised his eyebrows.

She just giggled, and skipped to her pom-poms, bending down, extremely dramatic and showing him her naked pussy, only standing straight after hearing her boyfriend hissing.

"We gotta see professor Samuel, coach," she answered simply. "We can't be late."

Cassandra left his room before Dean could say anything, looking behind her shoulder and walking to the library that existed in the bunker before they had even started living them, opening the door to find Sam seated behind a desk, reading a book dismissively.

She knew all too well he wasn't reading it for real, but her eyes quickly averted to his body once she realised she wasn't the only one wearing a new outfit.

Cassie never knew Sam looked that goo in a tweed jumper. Had she known, he would be wearing them far more around the bunker.

She blushed and sucked in a breath when Dean's big hand moved to her ass, caressing her skin.

"And that is why I'm the favourite teacher in the school," he said smugly by her side, finger slipping down to caress her fold. "Right, sweet thing?"

She nodded, humming positively and letting her lips fall open at the soft pleasure.

"That and your oral skills," Sam put his book aside, raising his eyes to them. "Right, brother?"

"Yeah, yeah," he mumbled. "And here I was, trying to surprise you, little prick."

Cassie yelped when he turned her around, moving his hands to flip her skirt up, but she stepped away from him quickly.

"Coach Dean!" she exclaimed. "I need to talk to Professor Sam!"

Dean chuckled, and crossed his arms, looking over at Sam and letting her turn to do the same.

"And what do you need, Miss Cassandra?"

She moved on her spot, a little uncomfortable under his very intense stare.

"My last essay, sir," she mumbled. "You gave me a really bad grade."

He smirked, chuckling.

"Well, if you weren't so busy bouncing on Dean's cock, you could have studied and gotten a better grade."

Cassandra pouted.

"But..." she tried to protest. "I..."

"But, but, but... you?" he repeated, so mockingly. "You want a better grade."

She lowered her eyes.

"You deserve a better grade," he pointed out. "You are just a lazy little slut, and if you want to earn anything, you have to prove that you deserve it."

Dean's hand touched the middle of her back.

"I think she can show you how much she deserved a new grade, Sammy," he declared. "She can be so good."

Sam became silent for a moment, and stood up, crossing his arms.

"What's her body count?" he asked.

"Just me," Dean affirmed, smug. "She's faithful."

Sam laughed.

"A faithful slut, Dean?" he asked, condescending. "That is so you. You're gonna tell me you took her virginity?"

Cassandra raised her eyes, cheeks red and hot, and Dean laughed loudly.

"Oh, she was so adamant about keeping her purity," he told his brother. "But so dumb at the same time."

Dean moved his hand to her skirt again, and instead of just flipping it, he straight up unzipped it, yanking it down and exposing her lower half as it fell down and pooled at her feet.

"Dumb slut here thought putting the tip was like fingering," he chuckled. "And that she'd still be a virgin after that. It's the oldest trick on Earth."

Cassandra's cheeks were burning, but she just allowed herself to be pushed towards the desk, bending down when Sam pressed down on her back.

"Truly dumb, then," he moved his finger down her back, caressing her spine gently. "No wonder she is failing every class but yours."

"She can't fuck each and all teachers," Dean noticed. "Well... she could. But she's not that slutty."

Sam scoffed soundly, and she jumped when his finger moved down her ass-crack.

"Good thing I have a good rep with the staff," he sighed. "I'll ask them to give her some extra credit, and then she can be a proud C student."

Her eyes widened in surprise at how simple it sounded.

"Really, sir?" the woman moved.

Sam's hand pressed her down again.

"If you earn it, yes," he warned her. "If you're good enough, I'll answer them for you myself, what do you think?"

Sam's finger stopped over her asshole, and he hummed in satisfaction when he realised the surprise she had in store for them.

"She picked the plug herself," Dean chimed in. "What do you think?"

Sam gripped the end of the plug, pushing and pulling it and making Cassie moan.

"How good is her ass?" he asked his brother, completely ignoring her.

"I wouldn't know," Dean answered. "I never had it."

The room fell into silence for a moment until Sam straight up laughed.

"Lucky me, then," he slapped her rear. "My own little virgin ass."

"Consider it an early birthday gift," Dean said simply.

She whimpered and felt Sam rubbing circles on her skin.

"What is it?" he asked.

Cassie licked her lips. This wasn't just a role. She never had anything more than a plug or fingers in her ass.

"Sir, I'm afraid," she mumbled.

One of them breathed in soundly, and her eyes opened quickly when Sam spoke again.

"Yellow," he said.

Sam pulled her up, as Cassandra just let him, learning closer when Sam sat her on the desk, cleaning her cheeks from tears she didn't realise were there before then.

"Baby," he whispered. "We don't need to do it."

Dean walked to them, taking her hand.

"We can just do it like always," he assured her.

Cassie shook her head.

"I want to do it," she affirmed and giggled, still nervous. "And it is way better to do it with Sam, cause, Dean... you're big. And very thick."

He chuckled.

"That I am," he agreed, smug.

"I don't know if I should be flattered or embarrassed," Sam chuckled.

"Sam, you destroy my cervix every night," she looked at him. "If you are gonna spear through me, at least my ass has more space."

Her boyfriend laughed.

"Princess, that really doesn't sound as sexy as you think."

"Good," Cassandra looked at his face. "Because it is not supposed to. I'm just being realistic."

She breathed in deeply.

"I want to do it," she told them. "And you can degrade and humiliate me through all of it. But I don't want it to hurt."

Sam nodded slowly, agreeing.

"Okay. We will make absolutely sure it doesn't hurt," he assured her. "So... no spanking?"

She shook her head.

"Not today."

"Alright," they said together.

Cassandra closed her eyes when Sam leant in, kissing her temple just as Dean did so with her knuckles.

"Okay, let me bend out again," she stood up.

The boys chuckled, and she returned to her previous posture, breathing in deep.

"I'm green," she announced.

"Green," Dean agreed.

"Green, then," Sam caressed her back.

Sam's fingers moved down to her ass again, and he twisted the plug, making Cassie moan.

"Did you put it on all by yourself?" he asked, voice tone so condescending it didn't even feel like the same person she was talking with just a moment ago.

"Yes, sir."

He hummed positively.

"And do you like it, Miss Cassandra?" he pulled gently on it, slowly fucking her with it.

Her eyes fluttered closed, and she squeezed her thighs together, trying to get pressure on her clit.

But Sam wasn't satisfied and moved his free hand to spread her legs again.

"No tricks, princess," he commanded. "Answer me. Do you like having it in your ass?"

"Yes, sir," she whimpered.

"And I'll be the first cock you have in it?" he asked.

"Yes, Mister Winchester."

Sam hummed, and moved his free hand to her pussy, pushing two fingers inside.

"Did you touch her pussy before this, Dean?"

"Nope," his brother declared.

He rubbed her clit with his thumb.

"You're wet for me, then, Miss?" he hummed. "Got wet by having your teacher playing with your ass?"

"Yes, sir," she moaned.

Sam slowly pulled the plug away.

"Let's make sure your efforts are valued, then," he decided.

She could hear the plug being thrown away and moaned when she felt him slipping the head of his cock into her hole.

"Fuck," she hissed.

Sam stood there quietly, inside her, but not moving.

"Sam," she whined.

"Shh," he hummed. "Can't hurt you, princess. You're a virgin there, after all."

He pushed his cock a little bit, slipping in less than an inch.

"Please," she whimpered.

Sam ignored her cried, pulling back and pushing in once again, fucking her slowly, though shallowly.

Fuck, it felt like it would never end.

"What do you think?" Dean asked, moving closer and standing in front of her.

"Give me the lube," Sam hissed.

His brother chuckled, and she opened her eyes in time to see him pulling a small bottle of lube from his pocket and giving it to his brother.

Cassandra sucked in a breath and whimpered when the warm liquid spread over her asshole.

"Open your mouth, baby," Dean commanded, fingers undoing his pants.

Sam pushed his cock into her a little more, and grabbing her hips with his hands and adjusting her so that her torso would be resting completely on the desk.

"Careful," he told his brother.

Dean scoffed, and moved his thumb over her lower lip, caressing it.

"I've been fucking this whore for a while now, Sammy," he pointed out. "I know she can take it."

Sam said nothing, pushing more inside her, and Cassandra moaned.

"But I'll be gentle," he decided.

Dean pulled his cock from his pants, and she watched as he slowly stroked it.

"Open up, princess," he repeated. "Don't make me ask again."

Cassie moaned and stuck out her tongue, slowly taking his cock into her mouth and yelping when Sam pushed himself completely into her.

That was it. He was all in.

"Look at that," he hissed. "Stuffed with cock from your mouth to your ass, just like you deserve."

She sobbed softly, eyes crossing, and one of the brothers chuckled.

"I bet it was so easy for coach Dean to get into that pussy," he hissed. "Are you sure she was really a virgin, Dean? Such an easy pussy, can't be this innocent."

Cassandra whimpered, and Dean pushed his fingers into her hair.

"She wouldn't lie to me, Sammy," he hissed. "She's too dumb for that, remember?"

She jumped when Sam pulled back and thrust into her again, balls hitting her wet folds, though she just wanted them to give her pussy any touch or friction.

"I can't disagree with that," he laughed. "Little dumb bimbo is giving her ass to her teacher to get a miserable C."

Cassandra's pussy squeezed around nothing, leaking wetness down to her own thighs, untouched and just burning in need, and she just moaned with Dean's cock inside her mouth, fat length stretching her lips and heavy on her mouth.

"Desperate little thing," Sam pushed his hand up to her hair, pulling on it. "Just a stupid little fuck doll."

A tear fell from her eye just as wetness just coated her more.

"Dumb baby slut," Sam hissed. "Squeezing my cock like that."

"That pussy must be so wet," Dean accused, fucking her mouth slowly. "Do you think she can cum from that?"

The two moaned, and Cassie squirmed, reaching down to try and rub her own pussy, yelping when Dean grabbed her wrists and pinned them down.

"You are a toy," he hissed. "Just a little plaything. "Toys don't play with their pussies."

"I thought you said she was well-behaved, Dean," Sam hissed.

"I thought she was," he squeezed her wrists. "Can't even learn how to be a good fucktoy. Just stupid."

"It's okay," Sam squeezed her hips. "We'll teach her."

She whimpered, crying softly as her muscles tensed as pleasure took over her, crying softly, swallowing down Dean's dick, tasting salt from his precum.

"Fuck, that's a good mouth," her boyfriend hissed. "You'll love to have it."

Sam chuckled.

"What do you think, Cassandra?" he squeezed her asscheek. 'You'll suck me off too? Maybe I can write you a recommendation letter if you do."

Cassandra tried to speak through the cock in her mouth, and Dean moaned.

"What would he even say, sweetheart?" he asked. "Miss Cassandra is proactive. She'll spread her legs and offer her pussy to any professor who'll offer to fuck it in exchange for a mediocre grade."

Sam's finger tightened in her hair.

"She's very good at multitasking," he added. "Can take cock in her mouth and her ass at the same time."

She whimpered, closing her eyes, just completely lost in bliss.

"Her pussy gets wet for anyone who will tell her how much of a whore she is," he continued. "And she loves being called slut."

Their thrusts got harder and faster, and their breaths were loud as they grew breathless.

"And she'll swallow cum like a pro," Dean groaned.

His cock throbbed in her mouth, and Cassie just sucked him more, taking in as he came down her throat.

When Dean pulled away, Sam was still fucking her, so hard that the desk was moving under them.

"And her greatest task," he panted, thrusting into her through the words. "Is holding your cum in her ass all... the fucking... day!"

He stopped, breathing hard, and she felt the moment he spilt his cum inside her, growling and pressing her face to the desk.

Sam relaxed his grip, letting her rest and pant in her place, and rubbed her shoulder gently before pulling away.

"Come, baby," he whispered. "Let's get you up."

Cassandra let herself be lifted and sat on the desk, panting into Sam's neck.

"How do you feel?" he asked.

She rubbed her legs together, feeling completely used, though in a good way, blood pumping in her ears.

"Can I cum?" she whimpered into his neck. "Please, Sam."

Dean rested a hand on her thighs and she heard as he dropped something by her side.

"Of course you can cum, princess," he caressed her knees.

"Do you want Dean to eat you out, baby?" Sam offered, rubbing his nose over her cheek.

"Please," she whined.

Her boyfriends spread her legs, each holding one of her thighs and keeping her open and available for Dean's lips, and she moaned out loud when he licked her pussy and clit, feeling him pushing two fingers into her and bashing her in pleasure.

"Dean," she sobbed, and whimpered when Sam moved his hands to her tits, pinching and playing with her nipples.

"So good," Sammy whispered into her ear. "Baby, you behaved so well for us. Took our cocks so prettily."

She whimpered, panting and crying in pleasure. Cassie had been on edge for so long, she wasn't sure she would take much longer to cum.

"Our perfect little princess," he nosed her neck. "You did so well, baby."

Cassandra cried through her orgasm, shaking and trembling, bracing herself on Sam's shoulders, quivering, and started squirming when she came down.

"Do you want to cum again, baby?" he whispered into her ear. "Dean can make you cum again."

She squirmed.

"It's too much," she protested.

Sam caressed her tits more.

"Just a little more," he kissed her cheek. "Let us make you feel good, baby. Please?"

Cassie panted, clinging to him and practically howling when Dean curled two fingers into her g-spot, sucking on her clit.

When she came again, Sam swallowed her moans into a hungry kiss, resting his forehead over hers as she quivered with her eyes closed.

"Another one," he pleaded. "Give us another, princess."

Cassie cried softly, resting completely on Sam's grip, sniffing as her body just became soft, and he squeezed her tightly.

"Sam," she whimpered weakly. "Dean!"

Dean's lips moved faster, and his big hand held her thighs tightly as he hummed something against her.

When Cassandra came again, he pulled away from her, kissing all the way up her stomach, gently caressing her skin through the aftershocks of her pleasure.

"There you go," Dean whispered, moving up and kissing her lips softly. "You were amazing, baby."

Cassie nodded and wrapped her arms around his shoulders when Dean pulled her up, wrapping her legs around his waist and letting him carry her away and into the room they were sharing.

Sam was right there when he put her down, and Cassandra let him wrap a blanket around her.

"How do you feel, baby?" he asked softly.

"I'm good," she mumbled. "Tired."

Dean's lips touched her neck, and Cassandra waited as he wrapped an arm around her body, covering his hand with hers.

"Why don't you have your nap, and then I can cook you a nice and filling meal?" he offered.

Cassandra giggled.

"You spoil me," she yawned, resting her head on Sam's chest.

"We are your Doms," he pointed out. "It's our job."

She chuckled, burying her nose into his neck.

"Okay," she yawned. "We can do that."

"Okay, baby," Sam kissed her forehead. "We'll wake you up in half an hour, okay?"

"Okay," she mumbled. "Thank you."

Dean kissed her shoulder.

"You're welcome, sweetheart."