“C-come on sis, I don’t want to do this!”
His sister, Joanna, smirked and shrugged, “Aww, Casey, I really don’t care! Now, come on, pucker your lips up some more, hm?”
After a reluctant sigh, he did so, quickly feeling her fingers on his chin, steadying him as she applied the red matte lipstick to his plump lips, “Yeah, yeah just like that, perfect…”
“C-come on, you can’t be serious?” He complained, voice soft once she was finished applying it, looking at his sister with wide anxious eyes as she glanced in a mirror, pursing her own lips before glancing back to Casey, as if comparing them.
“Yeah, you look perfect… One second, let me just do your eyelashes.”
Casey let out another sigh, feeling the butterflies float around in his stomach as his sister started to work on his lashes.
“I won’t do it…” he murmured, looking away from her for a split second, but she merely tittered out a soft laugh.
“Oh sweetie, you either do this or I tell mom that I keep catching you wearing my clothes, your choice?” She smirked.
“O-okay, but, anything but this, please?” He asked, a pleading edge to his voice.
“Nope, because giving head is icky, but if I don’t do it she’ll probably dump me and find a new squeeze to lavish with expensive gifts,” she smirked, looking up at him coyly, “soooo, she gets her cock sucked, I get my girlfriend and mom doesn’t find out you’re a cross-dressing sissy slut. Sound fair?”
Casey frowned, “….No.”
“Well tough, and smile more, you look pretty when you smile. And anyway, if you aren’t convincing, we all lose.” She smiled too sweetly, tucking the last of her makeup gear away, “There. Here, take a look.”
She produced her makeup mirror and turned it around. Casey looked down into the reflective surface and blinked, his eyes wide, it was the first time he’d had his makeup done by someone who knew what they were doing, and as he looked between the face in the mirror and the face of his beaming sister above it, the only difference was the expression.
“Wow…” He said, without thinking, she giggled.
“I know, right? You already sound like me Casey, so, you know, just be a good girl for Shahira.”
He took a deep breathe, “And you promise not to tell mom if I do this?”
Joanna giggled again and patted his shoulder affectionately, “Of course I promise!” He smiled a tiny bit in relief, “I bet she won’t be satisfied with one blowjob anyway…” Casey opened his mouth to protest, but his sister shushed him, “Come on, I’ve been up here for long enough, she’ll be getting suspicious!”
“Okay, okay, is there anything else I should know?” He asked, his heart hammering in his chest.
“She likes to squeeze my ass and thighs, so, you know, just make sure she doesn’t grab your dick or anything.” She giggled again, quietly.
“Well obviously she likes your butt, it’s not like you’ve got tit’s to squeeze.” He commented and she batted his arm making him wince, but he smirked, knowing he’d hit a nerve.
“Pff, if I had to buy bra’s you’d steal them anyway, now go, go have ‘fun’.”
His smile slipped and he sighed deeply, looking at himself in the hand mirror one last time before glancing at Joanna and standing, stepping out of his bedroom and heading for the stairs.
As he stepped downstairs he could hear the TV in the living room and he realised he wasn’t sure what his sister had been watching before she had come upstairs, but he doubted it mattered much. From what he’d gathered their date night had proceeded past the Netflix stage and well into the heavy petting of the Chill stage.
He swallowed and ran his fingers down his pants, the entire outfit he was wearing belonging to his twin sister but, to his shame it fit him pretty flawlessly.
He poked his head around the corner to the room and peered in, the room was dark with no lights save for the warm glow coming from the TV, illuminating a cosy two-seater, one seat occupied, the other invitingly empty.
Shahira glanced up and spotted him, her full lips, painted a deep crimson red turning slightly into a curious smile, her warm accented voice coming out soft and soothing, “You took your time Jo baby, nervous?”
He blushed a little and stepped into the room, sauntering towards her, trying to act casual as she reached out a hand across the back of the second seat, as if inviting him into the crook of her arm.
“Ah, sorry, I just, you know, never done anything like this before…” He said shyly, his nerves apparently something she had been expecting from Joanna.
“I know honey, but I really really appreciate this, I’ve been dreaming about nothing else.” She smirked playfully, raising her other hand to gently adjust her hair obscuring hijab, tan but with a darker floral pattern stylising it.
Casey nodded a little and sat down beside Shahira, scooting into the cusp of her arm.
She leaned up a little and glanced across at him, a curious look swimming in her deep hazel eyes, her own makeup heavy on the eyeliner, a striking, beautiful look.
“W-what?” He asked, nervously.
“Mm… I don’t know, you just seem…” She trailed off and looked at him searchingly, “Mm, probably just your nerves showing through cutie.”
She laced an arm around his shoulder and pulled him close, his head resting on her substantial chest, her other hand sneaking across to rest and squeeze his thigh, making him tense a little.
She let out a soft little chuckle, “Relax Joanna, it’s easy, you’ll enjoy it I’m sure…”
“You… You think so?” He asked.
“Mmhm, come here…” She moved her hand from his thigh to his wrist, holding it and guiding it towards her jeans, resting his hand on a very definitive bulge. It felt bigger than he’d thought it would.
“W-wow it’s uh, really big.” He said, biting his lip.
“It’s not like you haven’t seen it…” She purred a little, a little bit of pleasure in the tone of her voice as Casey squeezed the thickening shaft through the increasingly tight prison of her jeans.
“T-true…” He said uncertainly.
“And that one handjob…” She said, voice low, searching.
She smirked a little, “Mm, take it out cutie…”
After a moment’s hesitation, he reached to her zip, pulling it down and undoing the button, reaching in to close his slender fingers around her hot thick length, letting it fill his hand.
Shahira moaned a little and shifted herself a little lower in the seat, running her fingers through his long brown hair, getting herself ready for what she knew was coming.
“Come on sweety get those painted lips down there, give it a kiss…” She urged, smirking.
Blushed he glanced up at her, then leaned down and in, pressing his lips to the silky warmth of her hardening cock.
“Is that so bad?” Shahira asked cutely.
“N-no?” Casey said, cheeks flushed as he moved to lean back up again, but her hand on his head kept him pushed down.
Shuffling a little, he moved to lay down on his side, his head in her lap looking down at the now almost hard cock, a deep chocolate colour he saw, darker, he noticed, than the rest of her exotic skin.
“Try taking just the tip into your mouth, taste it.” She urged, pressing his head down, guiding his lips towards the head of her cock.
Without thinking he let his lips part, opening to accept the cherry tip of her thick cock, feeling it press between his lips and deeper into the warm wet embrace of his small mouth.
“Oooh fuck sweety, that feels so good!” she moaned, biting her lip as she switched which hand was resting on the back of his head, enabling her to reach across and slide a hand down the back of his pants, gripping and squeezing a handful of his bubbly ass.
With a surprised whimper, he leaned inward a little, his lips taking in a few more inches of her cock deeper into his mouth, groaning softly around it as she moaned her pleasure.
“See? I knew you’d be eager.” She teased playfully as she pulled on his ass, making him take more of her cock until it pressed briefly against the entrance to his throat.
He whimpered in sudden surprise and pulled back, which she allowed to a point, her hand stopping him just as his lips came to rest just past the crown of her cock.
“Start sucking it honey, and use your tongue.” She said softly, her hand almost aggressively kneading the softness of his ass as he obeyed her, feeling a warmth in his chest as he rolled his lips up and down her cock, feeling her hand caressing the back of his head, her soft moans as he sucked her cock all the proof he needed that he was doing a good job.
“And your tongue babe, your tongue,” she pressed, grinding her hips up slightly until she felt his tongue press harder to the underside of her cock, tickling under the head as she guided his head up and down.
“Just like that… Ahh, ah fuck, see? I knew you’d love it… First time I saw you I knew I’d found a cocksucker.” She teased, her hand squeezing his soft ass with such force he whimpered around her impressive girth.
He squirmed, body pressed against her, feeling his heart hammering in his chest, his thighs pressed tightly together to hide a hard secret from her as he did his best to pleasure her dark shaft, his lips gliding easily up and down over the slick, spit-soaked length of her cock.
“Come on baby, make me feel good, Shahira moaned softly, moving her hand from the back of his head sending it up under her own long sleeve shirt, her fingers urging under the wireframe of her bra so she could cup and squeeze her bare breast, full in her hand.
Shahira tilted her head back and parted her lips, revelling in the sensations pervading her body, the soft white ass gripped in one hand, her own full soft breast in the other, an eager little slut bobbing their head up and down, sucking her thick cock, life at its best.
She gasped out softly as she felt his hands, one resting on the warm chocolate skin of her stomach, fingertips caressing her, the other wrapping around the base of her huge cock, squeezing and stroking her, the sensation odd in his hand, like his own but so much more powerful.
She moaned and he tasted something salty and thin, his tongue swirling up, collecting the liquid which he swallowed without thinking.
He leaned up, panting hard, “A-ah, Shahira, did… Did you just cum?” He asked, voice a little husky.
She laughed softly and looked down at him, smirking as she caught her nipple between her fingers, making her bite her own lip, meeting his half-lidded lustful gaze with her own, “No baby that’s just pre, keep going though and I will soon, promise, and trust me, you’ll know when I cum.”
He nodded a little and smirked cutely up at her before turning back to look at her cock, feeling it throb between his delicate fingers, the dark length crowed by a cherry tip, shiny and wet with his spit, her length smeared with a few marks of red from his lipstick.
He closed his eyes and dipped his head back down, kissing the tip of her dick before pressing his shoulders down, feeling her hand squeeze his ass in appreciation as his cheeks caved in, sucking hard on her tip as he sank her cock deeper into his mouth.
“Yeah, faster baby, I want to cum in that pretty little mouth of yours…” She purred, taking a deep shuddering breath as her world was once more filled with pleasure.
Obeying her command he sped up, sucking hard, lewd wet noises escaping the tight ring of his lips, as he dutifully sucked her cock, all thoughts of being blackmailed gone from his mind, now just simply striving to make her cum.
Biting her lip she pulled her hand from his pants, her skin indented slightly from the waistband of his jeans she lifted her hand to her mouth, moaning slightly as she pressed the middle finger of her hand between her lips, tongue swirling around the digit, wetting it as best she could before, smirking, she reached across, sliding her hand back down into his pants.
Casey was entirely focused on his task of getting her off, not noticing her hand on her ass, at least, that is, until he felt a wet finger press against his hot little star, pressing into him ever so slightly.
Whimpering in surprise he leaned up but felt her hand once again on the back of his head, pushing him back down, “Shh shh shh, keep sucking my cock baby, let me do my thing, it’s just so fucking hot…” Shahira purred, biting her lip as she slid her finger in and out of his virgin star, just up to the first knuckle, but enough to make him squirm.
“Yeah suck harder baby and relax your ass for me, I’m gonna cum soon, so ah, ah stroke it, and I just know you want to swallow,” she said, voice heavy with lust and need.
He sucked hard, tongue swirling tightly around the tip as he tried his best to relax his ass, feeling her finger working in and out of him, her cock becoming steely hard, pulsing suddenly in his mouth.
She hadn’t been kidding, he knew precisely when she was cumming, but not just because of the sudden burst of thick hot seed filling his mouth, but that in her moment of euphoria she pressed her finger as deep as she could inside his hot tight ass, causing him to squeak as she worked the finger deep inside of him, twitching her hips up to cum as deep in his little mouth that she could without making him gag, loving the feel of wet heat of his mouth wrapped snugly around her cock, better than any pussy she thought.
Whimpering he swallowed, gulping down her hot cum, struggling to take it as quickly as she gave it, each time he emptied his mouth down his throat, her balls filled it once again.
After a short while, panting softly, the grip on the back of his head lessened, just resting and caressing his brown hair as he finished swallowing the last of her cum.
Smirking softly she pressed her finger deep within him again, just for the pleasure of hearing him whimper before she withdrew herself, squeezing his ass before fully withdrawing her hand from his pants, resting it gently on his back as he nursed on her softening cock.
“There… Now tell the truth, you enjoyed that, didn’t you?” Shahira smirked, shuffling in her seat, using a hand to move her breast back into the comfort of her bra.
Casey sat up, blushing warmly, placing his hands on his lap to hide a hard secret, “Y-yeah, that was… Ah, really nice…”
Shahira nodded and smirked, reaching across to run her fingers through his hair, “Mm, I suppose you’ll want to go fix your makeup now?” She asked, coyly.
He blushed deeper, having forgotten for a moment that he was just there for the blowjob and not actually her partner, “I er, y-yeah.”
“Mmhm,” she hummed, tucking her soft cock away as he stood, glancing at her as he made for the door, her voice full of amusement as she continued, “I’ll see you next time I want a blowjob, or maybe that sweet ass, lover boy…”
He blinked and looked over at her, eyes wide, “W-what? You knew?”
Shahira smirked, raising her hand to adjust the silk of her hijab, it having slipped a little out of place, “Joanna never gave me a handjob, but you will, won’t you? Whenever I want.” She said, confidence in her voice.
Casey swallowed cutely, then nodded.
She winked playfully, “Now run along…”
He did, knowing he and Shahira were going to be seeing each other a lot more often…
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