Cassandra's eyes moved over the written contract in front of her eyes, with both the boys' signatures on the indicated lines. Their personal kinks, fantasies and acceptable or unacceptable roleplays, turn-ons and turn-offs, and safewords.
"What do you think?" Sam asked.
She hummed to herself for a second, and then looked at him.
"I have a question," she decided.
The contract was very well-made, and Cassie was absolutely sure it had to do with Sam's past studying law, but it only said to last one year.
"Yes?" Sam sat by her side.
"The expiration date," she looked up at him. "Why?"
She could see him relaxing, and just frowned more. They wanted to be her boyfriends and Doms for one year and that was it?
"Well, it is for safety reasons, mostly," he explained. "It's like a driving licence, you know? You have to keep renovating it."
She continued to frown, and her boyfriend adjusted to his seat.
"Every year, the month before our contract expires, we will revise and re-edit our lists of acceptable or unacceptable things. Our kinks, roleplays, safewords… everything," he explained. "And then we will make a new contract and that will last for another year."
Sam reached out, and placed his hand on top of Cassie's, and that made her relax a bit.
"We are partners before we are Doms and sub," he reminded her. "And we have to always make sure everyone is comfortable in our relationship. The contract only assures that."
It wasn't an expiration date on their relationship, but the certainty that they could always have space to change and evolve.
That was nice.
"If you're having second thoughts," Dean chimed in. "We can-."
"No," Cassie interrupted him, turning to look in his direction, and she could see how he was a little bit pale. "This is what I want."
Her boyfriend smiled, and she crooked a finger, calling him closer, and pressed a kiss onto his lips when he leant in her direction, doing the same to Sam before reaching for a pen and writing down her name on the indicated line.
"Done," she smiled.
They all smiled, and Cassie had just lowered her hands, rubbing her thighs a bit, when Dean cleared his throat.
"So… what do you want to do now?" he asked. "We should celebrate."
Cassandra shot him a look, and raised her eyebrow.
"What do you want to do, sir?" she blinked slowly, giving him the most innocent of looks.
Her thoughts were very much not innocent.
His answer came in a kiss, and Sam whisked the contract away, putting it inside a folder, while Dean just picked her up and placed her on the table.
"Been dying to eat your pussy," he mumbled against her lips.
Cassie giggled. Oh, yes. Dean absolutely had an oral fixation.
Most specifically, an oral sex fixation. On the giving end.
His hands moved down her thighs, and Sam stood by his side, quickly taking his place when his brother his face to look at whatever he was doing.
She jumped, however, when the sound of Castiel popping into the room made everyone stop and turn to look at him just as her pants were being thrown on the floor.
"I have news," he announced.
Cassandra almost cursed aloud. Sure, she did it in her head.
Out of any time he could have shown up, he does it when she's about to be eaten out.
That was very mean of him.
Sam's big hands moved to her back, and Cassie blushed when she felt them covering her exposed butt.
"Really, Cas?" he asked. "Right now?"
The angel stared at them with furrowed browns, and she rubbed her temples.
"What, are you busy?" Castiel asked.
"Not anymore," she sighed. "Go on."
He started speaking, but her attention was moved away when Dean moved his hands around her hips and placed his jacket over her ass, giving Sam space to walk to their angel friend.
"There you go," her boyfriend announced. "Covered up enough to go fix our situation."
She smiled, grateful, and held back a giggle when she realised he was pouting.
"Gonna have to crawl to a safe place, I guess," she chuckled.
Her words were halfway out of her mouth when Dean growled, and a thought just popped into her mind.
They always wanted to be sucked under the table. Sure, Dean had said that in an office roleplay, but… well… why not?
Cassandra jumped out of the table, and Dean resigned to just crossing his arms, probably expecting her to leave the room. Instead of even moving to get her pants, though, she crawled to under the table, and settled in front of him, resting her hands on his thigh and holding back a chuckle when her boyfriend jumped in surprise.
Before Dean could say anything, she moved her hand to his, slowly closing his fingers and sticking his thumb out, moving it to point up, and then turning his wrist to move it down, hoping it would be enough for him to understand her question.
He hesitated for a moment, and she relaxed when she watched him moving his hand and making a positive sign, at last.
Cassandra's delicate fingers moved to his crotch, and she lost no time, pulling his cock out and stroking it, already finding him half hard.
He spread his legs wider, and she bit her lower lip, hearing Castiel's voice as he described the news to Sam.
The brothers were both big, but Dean was considerably thicker than his brother and stretched her pussy like nothing had ever done before.
Cassie moved, and slowly sucked him into her lips, moaned softly when his cock grew more in her mouth, and Dean's pushed his chair closer to the table.
It was a hard angle, sure, and she knew that she wouldn't be able to take all of him in once he was completely hard, but it was okay.
She'd get him off anyway. She knew it.
Cassandra pulled away, and used her saliva to caress his cock, feeling Dean throbbing against her fingers.
Her boyfriend was always very responsive.
She worked her mouth and hands around him, careful and dedicated, and froze when something touched her back, turning around quickly and finding Sam's foot on her hip, trying to push his brother's jacket out of the way, and quickly unwrapped it from her waist, licking her lips when he started caressing her covered folds with the upper part of his foot.
Dean's hips moved slightly, signing out to her that he was still waiting for her, and Cassandra started stroking him again, still hearing Castiel's voice.
Hopefully, he'd be gone soon, and she'd be able to have something else on her pussy.
She's just swallowed down his cock again when Dean groaned, and rested a hand over her head.
"Is that all, Cas?" he asked, pushing his fingers into her hair.
"Yes," the angel confirmed. "Where is Cassandra? I need to give her the information too."
"Waiting for us to fuck her," Sam said bluntly. "Like we were about to do before you showed up."
Her cheeks flushed red, and Dean cleared his throat.
"We are also not into voyeurism," he told him. "So… goodbye. We'll let her know about everything."
It took less than a minute for Sam to reach out for her and pull her from under the table, making her release Dean's cock and crawl in his direction, standing up to find him staring at her with hungry eyes.
"You didn't even wait for me," he shook his head.
Cassie pouted and Sam looked over his brother.
"Did you ask her?"
Dean chuckled.
"Nope," he denied. "It was all her idea."
She smirked, but lost her smile when Sam shot her a disappointed look.
"So you decided to suck one of us off without our permission?"
Her eyes widened, and Cassandra looked back at Dean, looking for help.
"But I asked for his permission," she protested. "I waited for him to..."
She stopped. To what? Say yes? Cause he hadn't actually said yes. He just pointed his thumb up.
She pouted, crossing her arms.
"But... sir!" she whined.
Sam shook his head, and pushed the chair away, tapping his thigh.
"Thigh or table, sweet thing," he commanded. "Your pick."
She bit her lower lip, and lied over the table, finding Dean stroking his cock.
Sam adjusted her hips at the edge of the surface, and Cassie sighed.
"Thank you for letting me choose, sir," she spoke softly.
He hummed positively, and caressed her ass softly.
"Tell me your colour, baby?"
"Green," she assured him.
Dean nodded a little bit, and she closed her eyes, gasping when Sam's hand hit her ass
Fuck, his hand was so big it covered her own cheek when he slapped it.
When she opened her eyes, Dean was standing in front of her with his cock out, close enough to her face that she could suck on his tip and a little bit more, and she did so as soon as he positioned it closer to her lips.
Sam's slaps were quick and strong, and when he was done, Cassandra's ass was hot, and she could feel her blood pumping on her skin.
"That's a pretty picture," her boyfriend whispered behind her, and the blonde let out a short squeak when he penetrated her without an ounce of mercy. "Fuck, you're so wet, baby. Did get spanked made you this horny, or was it sucking Dean's cock under the table?"
She whimpered. Both. Both had done it.
He pulled away a little bit, and pushed himself inside, and she moaned.
Fuck, Sam had a long cock, perfectly straight and knew far too well how to use it.
"You got her pretty ass very red," Dean noticed.
He chuckled in response, and pushed his cock in more, rubbing right against her cervix. The actual feelings wasn't the most pleasuring one - it was actually a little uncomfortable - but the actual feeling of having him fully inside her was insane.
Sam hardly ever gave himself that opportunity, and she just knew she'd be bruised by the time he was done with her.
"Fuck," Dean hissed, and she could feel the precum he'd been releasing inside her mouth pooling on her tongue. "Gonna cum soon, sweet thing."
Sam's fingers moved to her clit, and he played with her sensitive bud fast and hard.
"Paint her face, Dean," he instructed. "She likes being messy."
Cassandra whimpered, moving her legs as she squirmed, sucking on Dean's cock more and feeling her walls squeezing Sam.
"Oh, yes," he cooed, green eyes meeting her gaze. "You want that, baby? Want me to rub my cum all over your pink cheeks?"
She nodded precariously.
Dean smirked, and pulled his cock out, stroking his length, and she closed her eyes when he pressed the head of his cock against her cheek, and he groaned in pleasure, rubbing and spreading his cum all over her lower face.
She licked her lips, and panted when he pulled his phone out, filming her face for a moment before moving away from her.
"Look how pretty you are," he cooed. "My cum looks better than any makeup on your face, doesn't it, sweetheart?"
She nodded, whining.
"Please," Cassie cried out, desperate.
Sam's fingers were fast as he played with her, and she was so fucking close to cumming.
"Beg pretty," Sam instructed her. "And I'll let you cum. Be pretty for Dean's camera."
The boys could do whatever they wanted to her, but while they would never deny her an orgasm, she needed their permission to do it.
She was just such a needy little slut, goodness.
"Please, sir," she pleaded, staring at the camera. "Can I cum? Please?"
She closed her eyes, receiving no answer from him, and Dean chuckled.
"Sammy?"
"I don't know, Dean," he teased her, moving faster and more precisely. "Maybe we should make her wait a bit?"
Dean laughed, and she pouted.
"Come on, Sam," he caressed her hair. "Don't be mean to our little slut."
He laughed behind her, and tapped her clit gently.
"Alright, then. Cum for me, pretty thing."
Cassandra's body shook as she came, moaning and crying out in pleasure, and Dean walked away from her front to film her pussy, and she whimpered when she felt Sam's cum pouring inside her.
"Look at that," he hissed, caressing her ass.
"So pretty," Dean reached for her, pushing a finger into her and shoving his brother's cum in.
"Thank you," she mumbled.
Sam placed a soft kiss on her back, and helped her standing up before lifting her up in his arms.
Cassandra wrapped her arms around his shoulders, and Sam walked her to her room, laying her down and spooning her just a moment before Dean entered the room with her aftercare kit.
"Spread your legs, sweetheart," he kissed her forehead. "Dean's gonna clean you up."
She nodded, and complied as Dean wiped her pussy clean of cum and offering her a bottle of water, tipping and letting her drink slowly.
"You were so great, sweetheart," Sam kissed her forehead. "You did so well."
She nodded, hiding her face in the crook of his neck, and smiled when she felt Dean kissing the back of her neck, covering her with a warm blanket.
"I hope I didn't make Cas uncomfortable," she mumbled.
"Nah," he shrugged behind her. "He's seen us in weirder positions."
"He's seen you in weirder positions," Sam corrected him. "Don't worry, sweetheart. He didn't even notice."
She nodded, and wrapped her fingers around Dean's when he closed his hand around hers.
"So pretty," he kissed her cheek.
Cassie giggled, and sniffed Sam's neck, looking for comfort.
"You want to take a nap?" Dean offered.
She confirmed with a little hum, and he caressed her hip.
"You can rest, baby," Sam kissed her temple. "We'll wake you up in time for dinner and a little bubble bath."
"Okay," she mumbled. "Thank you."
They both kissed her available skin.
"Don't worry."
She closed her eyes, but opened them again for a moment.
"Sir?" she called.
"Yes, sweetheart?" they both asked at the same time.
"Can we have pizza for dinner?"
Her boyfriends chuckled, and Dean just giggled into her neck.
"Of course, baby," he assured her. "Don't worry."