Cassandra cocked her head to the side, interested, watching Dean as he worked out in the small bunker gym, and bit her lower lip. She'd been observing him for a while. He wasn't like Sam, who did it every day and kept his muscles defined, but still did it twice or so weekly, to keep his stamina for haunting. Seeing him now just made her think very - very - much of one of his proposed roleplays.
Coach Dean fucking a bimbo Cheerleader who needed a recommendation letter from him.
Now, she had no idea if that was something in college - Cassie had never tried to go to college and was old enough to have forgotten how the process worked - but it was certainly one of her and his fetishes to be in a controlled situation where she was seduced by this authority figure and fucked him in exchange for something.
Being with the boys made her feel more adventurous and free in her sex life. Right now, knowing she just could trust Dean enough to be the person who executed that fantasy with her… it felt very good and safe.
So, she ran out of the room, and changed her clothes into something that looked a little more slutty, but not something designed to seduce anyone, and pulled her hair up in a ponytail, sending Sam a little kiss when he shot her a confused look before running out to the gym again.
"Sir?" she cleared her throat, trying to summon her inner cheerleader.
Her boyfriend raised his eyes, a little surprised, and raised an eyebrow at her.
"Coach?" she repeated.
His lips curled in a little smirk, and she watched as Dean adjusted his posture.
"Cassandra," he nodded. "Come in. Close the door."
She skipped into the room, trying to keep her posture a little less excited and more submissive.
"I was wondering," she looked for words. "Have you had time to work on my letter?"
His jaw moved slowly, thinking, and he squeezed his eyes a bit.
"Well…" he crossed his arms. "I have, Cassie, and I have to tell you, your grades aren't looking too good, and I don't feel like I can give you a really good recommendation letter."
Her face fell. Well, he wasn't wrong even in the play pretend - she wasn't exactly big on the studying area, considering she had had to hunt during school.
"Oh," she mumbled. "But I do so well in PE, and I'm the best cheerleader in my group! I'm sure those things mean something."
Dean shook his head, eyes tracing her naked legs.
"You do very well in PE, sweetheart, but only in PE. The other teachers say you're dedicated but a little bit of an airhead," he pointed out. "Mister Winchester even said that you keep daydreaming in your English class."
She pretended to be embarrassed, looking away from his face.
"It is not my fault," she argued, and bit her lower lip. "And I didn't know you two talked about me."
She imagined Dean meant that his brother was the English teacher, and the idea of playing with Sam the same way she was playing with him right now… well, it was a nice idea. Maybe as a student who wanted a better grade, or just a recommendation letter… she was sure Sam would love it.
The way he chuckled, and it sent shivers all over her… it should be a crime.
"Don't feel too special," he warned her. "We talk about other students too. Compare performances if you say so. That friend of yours… I forgot her name, but she's good at PE too. She got a pretty good recommendation letter with my brother."
Cassandra frowned, feigning confusion.
"But she's as bad as me in English," she argued.
He grinned, so, so mean.
"Well, I can't say anything on that, but she had some extra credit, you know?" Dean cocked his head, green eyes staring deep into her soul. "She knew how to make my little brother happy."
Oh, he loved positively evil.
Her skin prickled up in shivers, and Cassandra breathed in deep, knowing exactly what he meant as her pussy creamed, and her nipples perked, wanting attention already.
Her boyfriend approached her, coy and cocksure, and hooked a finger under her chin, raising it, so she could look at him in the eyes.
"Maybe you could do me a little favour too," he offered, voice a mixture of teasing and mocking. "And I'll give you a brilliant letter."
Cassie panted, cheeks growing hot as she blushed pink.
"What can I do, sir?" she asked. "I really want to get to that school."
Dean laughed, shaking his head, and his fingers slowly descended to her shirt, playing with the top button that kept her cleavage a secret.
"Are you sure you don't know, Cassie?" he cooed. "The way you dressed up for me… can't be an accident."
She sucked in a breath, and watched as he undid all three of the buttons, gasping when Dean pushed the collar aside, enough that it exposed her naked breast.
"And no bra," he whispered. "Do you think I'm a joke, little girl?"
Cassandra's cheeks heated up, and Dean just undid all of her buttons, undressing her and pinching her nipple.
"Why don't you go over there," he instructed. "And spread your legs for me?"
Her eyes widened.
"Coach Winchester!" she protested, closing her shirt.
Dean just chuckled.
"What?" he mocked her. "Are you saving yourself for marriage or something?"
She opened and closed her mouth, unsure of what to say, and Dean apparently took it as a yes.
"Oh, sweetheart," he cooed.
Cassandra blushed, and he just moved his hand to her wrists, pulling them away before pushing her shirt out.
"We don't have to go all the way in, baby," he circled her breast with the tip of his fingers. "We can just play."
She bit her lower lip, and he pointed at the seat in front of the weights he was lifting.
"Go on," he repeated. "Go take a seat. I've always wanted to see that pussy."
She blushed, walking to the side, and sitting down by the seat, and Dean relaxed, kneeling in front of her and offering her his hands.
"Will you tell me your colour, please?" he asked softly.
"Green," she assured him, taking his hand and kissing his knuckles. "I want this."
Dean nodded, and kissed her cheek gently.
"Alright," he smiled.
His posture changed again to something meaner and hungrier.
"Now take off your those shorts," he raised his chin. "And show me what I want."
Cassandra bit her lip, and raised her hips, taking off her shorts and underwear and spreading her legs, blushing and looking away from him.
"Now, don't be embarrassed," he caressed her thighs. "You were the one who came here dressed like that, sweetheart."
Cassie hesitated, still clenching her thighs and pressing them together.
"Just a look, right?" she asked.
He smirked, thumbs moving in circles.
"Sure, baby girl," he spread her knees. "Go on, be a good girl."
She complied with his words, gasping the moment Dean reached for her folds.
"Look at that," he sighed. "Pretty pink pussy is already wet."
Her cheeks heated up in embarrassment, and Dean smirked, looking up at her face.
"Oh, sweet thing," he petted her clit.
"That's enough, right?" she asked, already panting and feeling hot as her pussy got wetter.
"Wet enough?" he smirked. "Could be more."
She trembled, and Dean leant closer, rubbing his nose over her skin.
"You said you just wanted to look," she protested. "You looked."
He ignored her question, and gathered wetness in his fingertips, playing with her clit.
"I need to have a taste, sweetheart," he told her. "I've been craving it for such a long time, you don't want to leave me hanging, right?"
She bit her lower lips, knowing the game very well. She'd been waiting to play like this for such a long time.
"Okay…" she mumbled. "Just a taste, right? And that's it."
He pulled her hips closer to his face, and licked in a long stripe from her entrance to her clit.
"Coach," she whimpered.
"Shh," he cooed, pushing a finger into her pussy. "Be good."
Cassandra moaned, squirming and unable to even look away from Dean, and he just smiled at her from where his mouth was just devouring her pussy.
"That's it, sweet thing," he flicked her clit. "Let your coach play with your pussy. You know how much you love it."
She threw her head back, too aroused to even think of anything else, but started pushing against Dean when her orgasm teased her body, creating little warning spasms on her muscles and making her legs tremble.
Oh gosh, how would she ask for his permission if they were pretending he was cornering her into this?
It just felt impossible.
"Dean," she whined. "Wait… yellow."
Her boyfriend stopped, freezing in his spot before pulling completely away.
"I can't ask for permission," she told him. "It contradicts the whole scenario!"
Dean looked at her in a comically confused way, and opened and closed his mouth as he seemed to try to process what she was saying.
"Sorry, blood flow is definitely not in my brain right now," he warned her.
Cassie giggled, and he rested both his hands on her knees again.
"Let's go that like this," he decided. "Cheerleader Cassandra doesn't need to ask permission to Coach Dean."
She nodded slowly, and he sat back on his heels, waiting.
"Can I go back now?" he pointed at her pussy again.
"Yeah," she nodded.
Dean kissed her thigh softly and leant closer, once again eating her pussy hungrily and making her simply scream.
"Fuck," she hissed. "Dean!"
His big hand descended on her thigh in a slap, and she hissed as the sound filled the room.
"It's Coach Dean to you, little slut," he corrected her, barely moving away to speak.
Her pussy became ever wetter at the addressing, and Cassandra jumped when his lips surrounded her clit, sucking on it without a care.
She squirmed and resisted, hitting his shoulders with weak slaps.
"Sir…" Cassie protested in desperate moans. "Please, please… I can't-"
"Cum on my tongue, sweet thing," he licked her hole. "Let your coach feel you."
He wrapped his lips around her bud again, and she all but jumped, squirming and crying in his grip.
"There you go," Dean kissed her thigh. "Good girl. That's what I wanted."
Her head was spinning when he pulled away, and she rested her head on the back of the seat, panting and still trembling in the aftershocks.
"That's it, right?" she closed her shaky legs. "You're gonna give me a good recommendation letter now, right, sir?"
He gave her a surprised look, feigning offence.
"Oh, no, sweetheart," he shook his head. "No. Remember what I told you? We're gonna play. This was nothing yet."
"But sir," she tried to protest.
"Shh," he cooed her, hoisting her up and turning her around before just lowering the seat and making her lay down. "Spread your legs, be a good little cheerleader for your coach."
Cassandra braced herself, unsure of what to expect, and whimpered when Dean moved his fingers over her spine.
"Look at that pussy," he spoke to himself. "All wet, baby. It deserves a cock, don't you think?"
She turned her head around to look at him, and Dean just rolled his eyes as she realised he'd taken off his pants.
"But my little baby is saving herself for marriage, right?" he mocked, fingers stroking his hard cock. "Don't worry, baby, I'll just rub my cock over it. It's okay."
Cassandra nodded, unable to say anything else as her body just fucking leaked more wetness to the seat where she was spread on, and whimpered when she felt his steal hard dick between her folds.
"Fuck, so wet," Dean hissed, grinding on her.
They'd talked about this, like with every other scenario. This wasn't just his fantasy, no… She couldn't remember how many times she'd fantasied with a man rubbing his cock on her and saying 'the tip doesn't count'.
"Coach," she moaned, eyelids fluttering closed.
"I told you it'd feel good, sweet thing," he caressed her ass. "Don't you feel better by listening to me?"
The woman nodded, feeling like just a horny mess, and shuddered when he brushed his cock against her entrance, causing her walls to contract.
"Look a that," Dean cooed. "Oh, baby… your pretty cunt is begging for something. The way it's leaking every time I move my dick… maybe I should put something in it."
He moved his cock, and she moaned when he simply ground the head from her clit to her entrance again, squirming.
"Coach," she protested, feeling him right by her entrance. "Coach, we can't!"
"Just the tip, baby," he coaxed her, cock circling her wet hole. "The tip doesn't count as sex. Didn't any of your friends tell you that? Uh?"
Cassandra cried out, cheeks flushed and hot, and she could hear Dean moaned at how her pussy was reacting.
"Oh, baby, see?" he teased her with his dick. "Your pussy wants it. It's so empty… we shouldn't neglect it."
She bit her lip and then looked at him.
"Just the tip, right?" she asked. "You're not going to put it in?"
"Of course, baby," he moved his hand to between her legs, petting her clit with his fingers. "What kind of bad coach would I be if I wasn't true to my word?"
She nodded, at least.
"Okay," she agreed. "Just the tip, right?"
Dean didn't answer, just pushing his cock inside her and stopping right by the tip, moving in and out of her, and moaning when he started playing with her clit.
"There you go, baby," he hissed. "Don't you like it?"
Cassandra whimpered, and squeezed the seat when he pulled out and circled her clit with his cock again.
"So wet, princess," he cooed.
"Coach Dean," she cried out, and raised her hips when he penetrated her again.
"Yes?"
He continued to play with her clit, and her cunt just squeezed around his cock. Fuck, she wanted to bed for more of him, but she couldn't.
"Go on, sweet thing," he tapped her clit softly. "Tell me what you want, go on."
"Sir," she whimpered. "You said you'd just play with me."
Dean laughed.
"But you came to see my with such a little number," he tapped her clit. "And I'm having so much fun."
She whimpered, and Dean squeezed her ass.
"Look at that pussy," he cooed, spreading her folds. "Oh, princess… are you sure you don't want more?"
Cassandra whimpered.
"But sir…" she squirmed.
"I'm already in," he pointed out, caressing her clit. "Baby girl isn't a virgin any more..."
"But…" she stuttered. "You said…"
"Shh," Dean shushed her. "I said you should be good, princess."
He teased her entrance, moving in and out, but never more than just the tip.
"But I have to respect my little slut's wishes…" he affirmed in a mocking tone. "If she doesn't want my fat cock all the way into her pussy, what can I do?"
Her cunt squeezed around him, and Dean groaned.
"But you sure feel like you want it, sweet thing."
She panted and moved her hips, trying to get more of him in, but Dean just held her in place.
"Sir," Cassie protested.
"You have to say what you want, baby," he cooed.
She squirmed.
"You're already inside," the woman tried to argue.
He chuckled, cocky.
"I am, baby, you're right," his fingers moved faster on her clit. "But what kind of coach would I be if I didn't make my little slut beg like the little horny fuck toy she is?"
Cassandra's body tensed completely, and she could feel herself so close to an orgasm. She just needed a little bit more, just a bit.
"Sir," she threw her head forward, writhing.
"Beg," Dean hissed. "Be a good fucktoy."
"Please, fuck me," he cried out.
His hips snapped, penetrating her all at once, and his fingers practically vibrated over her clit, making Cassandra just scream as she came on his cock, quivering and crying.
Dean's moans grew loud on her ears, and she felt as he released himself inside her, quickly changing demeanour, spreading kisses over her shoulder while he was still inside her.
"I'm sorry," he kissed her shoulder. "I thought I'd last longer."
"It's okay," she assured him, taking his hand and kissing his knuckles.
She released a soft moan when Dean pulled his cock from inside her, and wrapped her arms around his shoulders right when he pulled her into his arms.
"How do you feel?" he rubbed his nose on her cheek.
"I'm good," she yawned. "A little tired."
Cassandra's body was relaxing, and after everything, she just wanted to cuddle Dean and nap together.
"Let's get you to bed," he kissed her cheek.
She rested her head on his shoulder and Dean walked them to his room, resting her on his bed and letting him go after her special blanket, drinking the water from the bottle he'd placed by her side.
Her boyfriend cleaned her folds with a washcloth, and made a little silly face at her as he offered her a couple of cookies that were supposed to fill her up a little as she restored her energy.
"Come here," he whispered when she was done with the snack, and moved to spoon her.
Cassie, instead, just climbed on top of him and draped herself around his body, earning a giggle from him.
"So cute," he kissed the top of her nose. "You were so perfect, princess."
"Really?" she mumbled against his neck.
"Absolutely," he caressed her back. "Made the fantasy perfect."
She rubbed her nose on his neck, and kissed his shoulder.
"Thank you, sir," she mumbled.
"You're welcome, baby."
Cassie closed her eyes, and let herself relax over Dean.
"I love you," she told him, a bit hesitant.
It was the first time she'd said that to him. She hopped he would react to it in a good way.
Instead of reacting like it was new, her boyfriend just squeezed her a little bit tighter.
"I love you too," he kissed her forehead. "Now rest. I'll wake you up for dinner."
She nodded, already ready to drift off to sleep.
"Yes, sir."