It drives Dean crazy to see Sam pleasure herself on anything that isn’t his dick, and that’s probably while she enjoys making him watch so much. This time he’s spread-eagled on the bed, his hips canting upward as he watches her with wide eyes. She’s fucking herself on a big black dildo, one of her favorites, as she squats over him, holding herself upright with one hand on the center of his chest. It’s obscene, torture, and with every thrust of the dildo into her pussy he thrusts up himself, as though he can feel the enveloping warmth of her just from watching. when she cries out, and a rush of fluid splashes clear on his stomach, he gives an answering cry of desperation, suddenly moments away from a climax himself.
“Take out your tits,” Dean whispers as he slams Sam against the wall, then pushes against her, kissing her hard. She groans as she feels how hard he is, reaching inward to unbutton her tight plaid shirt and sliding down the wall to her knees. She he could take his cock in her mouth, but there are times when Dean just wants to slide against the creamy firmness of her breasts, and she knows that wild look in his eyes when she sees it.
“Oh, fuck, yeah,” Dean says, grinning, as she cups her breasts in her hands, pushing them up and against the shaft of his dick; “that’s it, Sammy, you just show me those hot tits of yours, gonna slide all over them and then come all over your face.”
“Oh, God,” she whispers, “I can’t wait to taste it,” and Dean has to grab the base of his dick and squeeze hard to keep from coming on her thick lips and gorgeous breasts right then and there.
Most nights Sam thinks she’s just a hole for her big brother to fuck, that he doesn’t even care where he’s sticking his dick as long as it’s wet and warm and clenches up around in him orgasm when he squirts into it (and she’s not even sure if he cares that she comes). It’s different for Samantha because she’s so desperate to make things right between them again, that she’s happy with any sort of attention he can give her; even if it’s only for a moment and probably morally questionable (but what in their lives isn’t morally questionable). And when he’s gone off to his own bed, flopped down to pass out for the night, Sam takes that time to slide her fingers between her legs and through the sticky wet mess covering her pussy lips. She strokes slowly, keeping her muscles clenched tight to make sure none of Dean’s spunk spills out of her, even when she finally squeaks and comes again… interrupted only by the weight of Dean’s body as he crawls on top of her again. “If you wanted me to fill your cunt again, all you had to do was ask, Sammy; you know I can’t tell you no.”
Their mouths are touching around his dick, and when Dean looks from side to side he can see their knees shaking from the force of their arousal. Lying on the bed, one of his beautiful girls on each side, he encourages them with rhythmic shoves of his fingers into their cunts and endlessly flowing words. “Fuck, Sammy, I know you love kissing Cas over my cock…” and she moans in agreement— “you like my fingers inside you like that, Cas?” a spasm of her muscles and a soft cry in response. His orgasm is building fast, the sight and the feel and the thought of them surrounding him, and he lets them lick wet tongues over him and each other, pumping his hands inside them and curling his fingers up until they’re both vibrating with pleasure. Cas screams first, and comes, juices pouring down over his palm and wrist, and Dean throws his head back, arching up on the bed and shouting “Yeah, that’s right, Cas, fucking come for me, so fucking close, suck my dick nice and hard you two, unh!” And that’s all he can stand, as Sam wraps her mouth over the crown of his cock and sucks him down, her body shaking furiously as he works ever harder into her, his pretty sister with the mouth and the pussy he can’t ever get enough of, even when their beautiful angel is there to help.