ⓘ stepbro!chris x stepsis!reader (m!masturbation), use of sex toy, detailed sexual fantasy, getting caught (and then stepsis!reader helps him 🤭), humiliation, faux sympathy, chris being just a little submissive
combined this request + this request 𖹭
dividers by @/ithemes
The driver's side door of Chris' Honda Accord collided into the frame with a heavy force, a loud slam sounding. He trudged up the driveway, his sneakers dragging across the pavement with a faint scrape, scrape, scrape. He let out an exhausted sigh as he clutched his keys in his fist, anxiously fidgeting with them.
It was finals week, and Chris was pretty sure he'd just bombed his last test.
Chris wasn't an easily stressed out person, and he usually had some pretty effective stress management skills. However due to the two of you being on opposite schedules, he wasn't able to relieve his stress with you. And he hadn't even had time to jerk off lately between studying for all his finals and all the housework his mom had him running around doing when he was home. It was really starting to get to him.
He placed his hand on the knob, slowly turning it and hoping that if he could get inside without being detected, his mom wouldn't immediately start nagging at him to do whatever chores she had on the agenda for today. To his dismay, his mom was sitting on the couch, knitting and watching some soap opera.
"Chris, you're home," she perked up, greeting him and adjusting the frames of her reading glasses that he rarely ever saw her in. "Hey, honey, once you get settled in, can you-?"
"Mom. Please," Chris interrupted her, holding up a hand to stop her. "Just give me an hour. I need some time by myself."
She didn't press. She just rolled her eyes, going back to knitting herself a jewel-toned scarf. "An hour," she said sharply, narrowing her gaze a bit, knowing this was a common tactic Chris used to avoid taking care of the responsibilities that he said he was going to.
"Yeah, yeah," Chris dismissively waved her off, bolting up the stairs and heading towards his bedroom. He slipped inside, the door latching behind him as he leaned up against it and let out an exhale. His glance flicked over towards his dresser, his heart stuttering in his chest. His feet followed his eyes and he made his way to other side of the room, reluctantly pulling open the drawer. He rummaged through a few things before he found what he was looking for - a sex toy. One that he was honestly even embarrassed that he had.
He'd once held an opinionated stance on pocket pussies. He'd made bold claims like, "only girls use sex toys" or "only guys who can't get pussy use a fake one to get off" - that was, until he'd tried it out for himself. He'd been talked into buying it by the cute sales girl who cashed him out at the sex shop the last time he'd gone to buy some restraints to use on you. He definitely didn't regret the purchase. In fact, the first time he'd used it, he ate his words about how he was too good for them.
He snagged the toy and a small bottle of lube from the dresser drawer and shoved it closed. Chris kicked his sneakers off right beside his bed before he collapsed down onto it. He didn't bother to get under the blanket or even take his jeans off all the way. He just unbuttoned them, lowered his zipper, and pushed them down along with his boxers just enough for his cock to come springing out. He popped open the lube, applying some to the opening of the toy. Then he tipped the bottle upside down over his throbbing cock, watching it twitch as the cool liquid made contact with his tip.
He carelessly tossed the bottle of lube to the side, pumping his cock with his hand a few times to spread the lubricant around. "Ooh, shit," he hissed through his teeth as he pushed his swollen head passed the petaled lips of the toy. His hips immediately twitched as he slipped in every inch of his cock, already fighting the urge to pound into it.
He loved the way it almost felt just like you. Chris started to stroke himself with the toy, feeling the soft silicone walls against every nerve ending and vein, driving him crazy due to the neglect his cock had received this past week. A soft moan slipped out, one that sounded needier than he'd meant for it to. He almost reached up to cover his mouth, worried that he'd give away what he was doing to anyone who was home.
His eyes fluttered shut as he continued jerking himself off with the pocket pussy he was starting to grip more tightly in his hand, images of you playing on the insides of his eyelids. He imagined you on top of him, riding him like your life depended on it. With your face burned into his memory, your flushed skin, your eyes rolling back, and your pouty lips parted in a look in pleasure, he found himself moaning your name. He pictured your breasts bouncing, the curves of your body, wishing he could hold you by your hips and pound into you from underneath.
He picked up the pace, the fleshlight sliding over his slick cock and making his stomach twist with desire and a bit of embarrassment, the inevitable sensation already brewing deep in his core. He couldn't believe a toy had him gripping the flannel sheets beneath him and biting down on his lip to keep himself from being too loud.
He bucked his hips up, fucking into the pocket pussy with a sense of urgency, chasing the feeling he'd been craving all week. A bead of sweat trickled down the side of his face, his breathing becoming more erratic by the second. He shut his eyes again, clinging to the image of you in his mind.
Suddenly, his bedroom door flew open.
"Hey, dickhead. Guess wha-" you started to say, immediately stopping yourself when you walked in. Your eyes widened, and your jaw fell to the floor in shock at the realization, not only at what he was doing but what he was using.
"Jesus!" He panted, tugging a nearby throw blanket over himself. He tried to stop his strokes, but it just felt too good. He continued slowly under the blanket, hoping you wouldn't notice. However, his fucked out expression betrayed him. "What the hell happened to knockin' before ya just walk in? I thought you closed tonight."
"I switched with someone," you replied, your eyes lit up and glued to the subtle movement under the blanket. "You have a pocket pussy?" You almost whispered, the door softly latching behind you. "I thought you said -"
"Don't worry about what I said," he barked back, cutting you off. You noticed a slight blush in his cheeks.
"Are you embarrassed?" The corner of your lip tugged into a smirk as you slowly approached him, arms crossed, eyes fixed on the way he was still lazily stroking himself with the toy. It wasn't very often that you saw Chris experience any kind of shame or humiliation, but it was kind of hot.
"No," he argued back defensively, almost pouting. "I don't fuckin' get embarrassed." However, his cheeks were still tinted pink, and every time his eyes almost met yours, they'd dart off in another direction. "Ya gonna help me or just stand there?" He asked almost sheepishly.
"Only if I can use the toy on you," you replied, your grin growing wider as you closed in on him until you were sitting at the foot of his bed.
He hesitated for a second, but he genuinely didn't care how he got off at this point just as long as he did. "Fuck. Fine." There was something Chris being alone in his room using a toy he used to talk down on that turned you on beyond belief, and all you wanted to do was see him fall apart.
Chris reluctantly slipped the blanket off of his lap, revealing the transluscent pink pocket pussy that was wrapped around his cock. You scooted closer, reaching out for the toy and wrapping your fingers around the silicone sleeve. The sound that passed through his pink lips as you started to stroke him made your stomach flutter. "Oh, my god. That feels incredible."
"I thought you didn't use these, hmm?" You taunted him, tilting your head and giving him a teasing look.
"Guess I changed my mind," he admitted, glancing down at your freshly manicured nails. His tongue darted out from behind his lips to wet them.
"I can't believe we haven't fucked all week," you told him, giving him a pouty look. "Bet you've been missing me."
Chris nodded slowly. "You have no idea."
You looked down at the way the toy easily glided over his cock, his composure slipping away. Broken moans and profanities unfurled from his lips between his heavy panting. His cheeks were still rosy pink from being caught. You'd never seen him look so submissive.
"You poor thing," you cooed, your tone dripping with condescension as you dragged the toy up and down his length at a steady pace. "I bet you wanna cum so bad."
Chris' jaw twitched in response, and he gave you a sharp look. "Cut it out."
"What? You don't like it?" You pouted and batted your lashes, giving him a faux sympathetic look.
"I know what you're doin'," he hissed back, swallowing hard as you used the soft, silicone walls to massage his shaft. "I'm not your bitch." He narrowed his blue eyes at you, shooting daggers with them.
"Well, you have two options," you spoke with conviction, your intense gaze flicking up to meet his. "Either you play along and you ask nicely if I'll let you cum, or I'll go to my room, and you can finish in here all alone." You gave him a little smirk, knowing already which option he was going to choose.
"Fuck," Chris groaned, half-pleasured and half-defeated, knowing he was incredibly close, and you practically left him no choice. "Fine." He sighed before hesitantly asking, "will you please let me cum?"
"I'll think about. If you keep being a good boy, your chances are better," you teased him, your grin widening.
"Fuck no. Call me that again, and I swear I'm gonna go soft."
"No, you won't. I think you like it," you taunted him, watching his body tense up, his knuckles turning white from gripping the blanket beneath him.
Chris rolled his eyes, trying to maintain his annoyed facade, but the small part of him that thoroughly enjoyed everything about this scenario kept slipping through the cracks. A moan fell from his lips, his chest rising and falling faster as his breath grew more labored.
"That's it," you purred, praising him. "You're doing such a good job."
His embarrassment had mostly subsided by now, overpowered by his desire, his desperation. He continued panting, gazing at you with a pleading look. "Faster," he begged.
You listened, picking up the pace and watching his length through the transluscent pink material as it glided into the sleeve with ease. "Fuck. Your cock is so pretty."
Normally a compliment like that would bother Chris and leave him feeling emasculated, but he was too close to protest or even care. "Please. Make me cum. I'm so close," he blurted out in a broken cry that he was worried would alert the whole house, his head falling back against his bedframe and his eyes rolling back in his head.
You gave him a mischevious smile, jerking him off with the stroker at a reckless pace. "That's it. Make a mess for me," you softly cooed, watching his body respond.
He couldn't take anymore. He needed it. The way you spoke to him, the way you stimulated him, and how long it had been since he last finished, it was all too much. He'd reached the point of no return, his orgasm tearing through him with no mercy.
His hips involuntarily lifted from the mattress, a slew of whimpers unfurling from his parted lips. You watched a week's worth of thick, white fluid gush from his tip and fill the toy, dripping down the sides of his twitching cock and the inside of the pocket pussy as you slipped it over his length, draining him completely. "Oh, fuck."
You sat in awe, still pumping the toy back and forth until Chris was squirming and begging you to stop, his cock too sensitive to continue. You glanced down at him, a prideful and aroused feeling brewing deep within at what a mess he was.
"Holy shit. That was so hot," you managed to say, watching him try to recover.
Chris was still breathless, wiping sweat from his brow, his face bright red from exhaustion and humiliation. "Yeah, yeah. Get the fuck out," he spat back. "You better not tell anyone about the pocket pussy."
