Chapter Text
“Aww baby I know you want it,” he teased, tapping the head of his cock at your entrance. You mewled, trying to rut back into him. You knew it was futile; when Dean was in this mood he did not leave room for compromise.
“All you gotta do is feel my thumb inside, that's all.” You and Dean had experimented with a small plug and his fingers one other time, but never while he was also fucking you. “You want my cock you’re gonna have to let me slip it in. You trust me, don’t you baby?” As he said that you were wondering if this was his plan the whole time he was getting you worked up and needy. “Promise you’ll cum right away.”
As if to tempt you, he started gently thrusting the head of his cock over your clit, and feeling the drips of his precum on your skin only made you want him inside that much more. He took your lack of protest as an invitation to rub his wet thumb around your ring of muscle.
“One day you’ll let me fuck you here and I don’t care what I have to do to make it happen.” The words made you clench, and when you relaxed he took the opportunity to gently ease inside. The stretch felt so so new, and the only thing keeping you from crawling away were his strokes on your clit.
“That wasn’t so bad, was it princess? Always know how to make me happy.” The stimulation on your clit turned into a pressure at your entrance, and you eagerly pushed back into him until you felt the uncomfortable fullness. You didn’t know how something as small as a thumb could make you feel like you were splitting open, but the strange feeling had you retreating until you felt a sharp tug on your rim.
“Good girls take what they’re given. You’re a good girl, aren’t you?” A cry escaped you, and you slowly eased back onto his cock to stop the punishment. The further back you went the more the tugging subsided, and when you were fully seated you finally felt like you were stretched out enough to relax. Dean started lazily fucking into you, seemingly content for the time being to admire his view.
“That’s it, baby. Taking me so fucking good. I should make you do this every time. Get you nice and trained.” He seemed to be talking to himself the way he was rambling and rhythmically fucking into you, but you shook your head anyway, not wanting this to be the new normal. Gripping his fingers in your hair to make eye contact, he began to mock you. “No? You don’t want to give me another fuckhole? I thought you liked pleasing me.” Your eyes went wide, and you tried to shake your head around the tight grip he had of your scalp. He smirked, seeming to love your reaction.
“I know, baby. Just like seeing you riled up. You know your pussy is all I fucking need.” He released your hair to slip his hand between your legs, and when his fingers met your clit your whole body went rigid, tensing up to feel him inside of you.
“Wow, someone’s fucking wet.” You let your head fall forward as he began to draw circles on you, and the way you needed him before paled in comparison to the desperation you felt now. “One night I should gag you and take care of you based on what makes your pussy the wettest, because the way she’s drooling for me now has you convinced you’re lyin’ about what you like.”
As he brought you to the brink he started fucking his thumb in time with his thrusts in a way that did make you question if you were lying about the things you like. Waves of pleasure crashed over you, and as you clenched you felt Dean speeding up, chasing his own release. His thumb never stopped moving, and it unnerved you how easily it had started slipping in and out of you. He drew your orgasm out long enough that when he spilled inside you were still feeling the aftershocks. He slipped his thumb from you and collapsed, pulling your body into his.
“Is that what you needed, Princess? I know you love it when I treat you like that. You don’t have to say it.” You nuzzled in even closer, planting a kiss on his neck in affirmation. He started painting long strokes down your back that soon had your eyes hooding, and you felt a smile creep on your face at how well you were taken care of.