III

Cassandra curled on Dean's lap, letting him rub circles on her back and kiss her shoulder as she read the list he had made on his phone, per her request.

To be completely honest, it wasn't so different from Sam's, except for the fact that Dean had a few – many – fantasies.

It wasn't a lot of things, but it was certainly… interesting.

"Dean, I have to ask..." she spoke slowly.

Between all three of them, Dean was the most hesitant one when it came to making things contract-official, and that worried Cassie a bit. Maybe he was against it or something?

"It is about the Daphne one?" he moved to look into her eyes, quickly. "Listen, you promised you'd be honest and not kinkshame me."

She stared at him for a moment, confused. Oh, Dean had written some fantasy where he was Fred and seduced Daphne for the first time – something that was between just them, and not supposed to involve Sam – but this wasn't what she was talking about.

"No, baby, no," Cassie sat straighter, putting Dean's phone down and moving to look at his face. "I mean with the relationship."

Dean stared at her with some confusion.

"Our relationship?" he asked.

Cassandra nodded, and he wrapped his hands around hers, kissing her skin softly.

"Sweetheart, I like you a lot," he told her. "I want to be with you, I want to be your boyfriend and I want to have amazing kinky sex with you. If writing it down in a contract will make it safer for us, then I'm okay with it."

She hesitated, and Dean caressed her cheeks gently, making her relax, at last, and she learn closer to him, kissing his lips.

"And what about nice sex?" she whispered.

It was Dean's time to watch Cassie's face.

"Nice sex?" he asked, softly.

She nodded, and bit her lower lip, a little hesitant.

"What if when I want it to be slow?" she asked, a bit unsure.

Cassandra loved sex with the boys. It was hot, it was daring and always made her feel the best of feelings.

But sometimes… well… it was nice to have gentle sex and all.

Dean's lips curled in a little smile, and he kissed her softly.

"Mommy and daddy style?" he joked.

She whined a protest.

"No," she moved away from him, and giggle when Dean tickled her side. "Just… you know..."

His lips moved over her neck, caressing her side.

"Whatever you want, baby," he promised. "Don't worry."

Cassie nodded, and sighed when Dean moved his hand to her breast, caressing it gently.

"Do you want to go over the list, baby?" he whispered into her ear.

She nodded, and Dean brought his phone to her again, unlocking it and adjusting her on his lap, and his girlfriend licked her lips, feeling him already growing hard under her.

"Read the list, princess," he instructed, slowly unbuttoning her shirt.

She blinked and sucked a breath, feeling his big hand engulfing all of her breast and caressing it.

"Uh... roleplaying," she recited.

"With what?" he kissed her shoulder. "Tell me the scenarios."

He pinched her nipple, and she sucked in a breath.

"Fred and Daphne," she stuttered. "Boss catching babysitter being naughty."

Dean smiled against her skin.

"You love being naughty, baby. I'm sure you'll be perfect, uh?" he squeezed her.

Cassie nodded, and he chuckled.

"Don't stop," he played with her nipple.

She breathed in, and his other hand moved to her hips, caressing and her over her pussy.

"Cowboy and virgin," she mumbled.

He chuckled behind her.

"My little damsel in distress who needs a good western pounding," he kissed her skin.

She giggled.

"You want to teach me things," she deduced, spreading her legs.

Behind Cassie, Dean laughed, and pushed his hand into her pants, and she whimpered.

Going over the list, thinking of the situations… it already made her feel hotter and already a little wet.

"Read the next," he kissed her earlobe.

Her eyes moved on the screen, and Cassandra squirmed.

"Naughty cheerleader and gym teacher," she whimpered.

Oh, goodness.

Dean's finger dipped into her cunt, gathering a little wetness and rubbing her clit, making Cassandra moan softly.

"How far would you go to make sure your favourite teacher would make sure you got a good recommendation letter?" he licked her earlobe.

She whimpered.

"I'd let him fuck my ass if he looked like you."

He laughed, and slapped her asscheek.

"Good to know, princess," he chuckled, and pushed a finger into her cunt.

Cassandra squirmed, but Dean just rode the phone to her eyes again.

"Next," he instructed her.

She squirmed on his lap, and his cock pocked her ass when she red the next item on the list.

"Degradation," she whimpered.

"Cause we both know my pretty princess loves it when I treat her like the slut she is," he sucked a bruise on her neck. "And show her what her place is."

That made her squirm even more, and Cassandra cried out when the heel of his hand stimulated her clit.

"And what is my place?" she asked, both teasingly and knowing the effects his words had on her.

He bit her shoulder and grabbed her hips, making her rub herself all over his throbbing dick.

"Right here," he hissed into her ear. "Being my little fleshlight."

Cassandra threw her head back, moving her hips hard and fast, rubbing ass on his cock, squeezing around his fingers.

"You love to cum like this, don't you?" he pinched her nipple, pulling and twisting on it. "Hearing how dirty you are?"

She nodded, confirming, and moaned out when he moved his fingers faster inside her.

"Yes, sir," she spread her legs more. "I'm your hungry little slut."

He growled darkly, and just pulled the phone out of her hand before pulling her closer to his body, lifting her up and taking off her pants, finger fucking her and rubbing her clit with intent.

"Go on, then," Dean hissed into her ear. "Cum like a dirty little girl around my fingers, but be fucking loud. I want to see you squirming and cumming on my fingers, and I want to hear you fucking screaming my name while you do it."

Cassandra cried out. He was using both his hands now, moving hard and fast, fucking taking her breath away.

"Dean," she cried.

"Louder," he hissed.

"Dean!" she cried louder.

"And you'll cum saying my name," he commanded.

Cassie nodded, only able to moan his name, trembling and shaking.

"Now cum already," he told her, using a mean tone he knew made her go insanely horny. "We have a list to go through."

Cassandra came, screaming Dean's name and shaking over him, and Dean only stopped when she started pushing his hands away from her pussy.

"Good girl," he kissed her cheeks, caressing her exposed skin. "There you go, baby."

He gently held and kissed her through the aftershocks, picking his phone up again only when her pretty eyes were staring back at his.

"Let's finish this, baby," he kissed her cheek. "I can't wait for you to see the rest of it."

She giggled.

"Yes, sir."