"Sure." She said, glancing in the mirrors just to make sure they were alone on the road, "Don’t let me stop you."

Casey beamed, his heart fluttering in his chest as he undid his seatbelt, letting it retract back to the side as he turned his body towards her. It felt weird, being in a moving car without a seatbelt, somehow different to a bus despite how it was pretty much the same. In contrast, however, as he leaned down across the divide towards her, tucking his legs up as he shuffled, it felt incredibly natural to be getting ready to suck off his sister's girlfriend.

Shahira rolled her shoulders and let out a content little sigh as she felt his small delicate hands fidgeting with her jeans, nimble fingers undoing the button and zip. She had to ask herself, and not for the first time, why she was continuing with all this.

While she did adore Joanna and genuinely loved her company, she couldn’t deny that Casey would make an absolutely ideal boyfriend. So kind and lovely, honest, eager and of course, just drop dead gorgeous. She knew she should probably break up with Joanna to steal Casey away instead, but something gave her pause.

The illicit nature of their meetings, the way he was made to look like his sister, the secrets they both kept from Joanna, it all added a thrill that she wasn’t keen to let go of so easily.

"Ahha~" Casey purred as his hand found and wrapped around her soft but partly swollen length, struggling for a few moments to free her deep chocolate coloured cock from her own increasingly tight panties.

After a moments adjusting it managed to spring free, Shahira biting her lip as she forced herself to focus on the road ahead and not Casey, who was now slowly stroking her thick length, loving the feeling of it between his fingers, the skin so silky smooth and hot to the touch, her cock still spongy soft, though he could feel it pulsing, eagerly expanding into his hand.

He didn’t want to waste any time, sinking down to wrap his painted lips around her cherry tip, sucking instinctively as he pressed his face down into her lap, feeling the still malleable dick slide deep into his willing mouth.

He moaned around her length as his tongue caressed the side of her cherry tip, feeling as her dark shaft grew in length and girth between his lips. He wasn’t entirely sure why, but he’d discovered with her that he really quite enjoyed taking her into his mouth before she was fully hard.

Maybe it was the unique hot softness of her cock, or perhaps the ever-present mental image that it was him, a skinny little girly white boy, who was making an erotic goddess like Shahira grow erect, but whatever it was he felt his own cock harden in his panties as he rolled his lips up and down the pulsing shaft.

"That feels so good baby…" Shahira moaned, having to resist the urge to curl her toes in her shoes as the pleasure began to radiate through her, driving her on to encourage him, "How deep can you go though?" She challenged, albeit teasingly.

Casey pulled up, swallowing down the spit that had accumulated in his mouth and breathed a little heavily, his lips parted as he eyed the now semi-hard length. He knew that the longer he waited the harder it would be, in every sense of the word, so why wait?

"Oooh yes…" Shahira moaned, adjusting her grip on the steering wheel as she felt his lips once again around her cock, pressing lower than before, moving until the tip of her cock bumped against his throat, the boy letting out a little whimper at the still uncomfortable pressure but she urged him on, "Come on Casey, you’ve practiced, I know you can do it…"

Her words and the use of his name seemingly bolstered his confidence and, though he moved slowly, tentatively even, she felt him press down, the pressure on the cherry tip of her cock increasing until, at last, it was fed into his tight squeezing throat.

Once the tip had made its entrance the rest of her semi slipped in with ease, his cute pink lips making an O around the base of her shaft. For a moment she wished that she’d bought Joanna a less blowjob resistant lipstick, if only so she could see the ring it would've left behind around the base of her cock.

Casey held himself deep, eyes closed as his discomfort mounted. He was entirely focused on not gagging or choking, trying his best to still suck and lick, but all his efforts were actually making it more difficult.

As her cock, completely wrapped in the wet heat of his mouth and the intense tightness of his throat, continued to harden, the length began to protest at the slight curve that had allowed it to enter Casey’s inexperienced throat. As it got harder her length began to straighten out, forcing Casey to roll his lips back up her spit shining length, letting it pop free as he gasped and coughed once, starting to catch his breath.

"Fuck Casey, you’re such a good girl, you know that right?" Shahira said with a soft genuine voice, feeling his lips as they brushed against her cock, leaving little angel kisses all the way up and down its length.

"T-thank you…" Was all he could whisper, so happy he’d made her feel good and feeling a genuine sense of pride blossom in him from her words. ‘Good girl’. He liked when she called him that, it sent a pleasurable little shiver through his body, that made him want to earn more.

He was about to take her back into his mouth when he felt the car pull up, for a moment he guessed they were at another junction but then he felt Shahira relax, the engine thrumming deeply as she switched it off, leaving the keys in the ignition to keep the lights on.

"Take a look." She said, leaning back in her chair as he pulled himself up and away from her cock, one of his hands delicately wiping a strand of spit from his pink lips.

"Oh wow…" He said softly as he looked around. She’d pulled into a carpark off one of the quiet hilly roads, a small building nearby, which he noted was boarded up and long abandoned, read, ‘Lookout Point Café’.

The view the spot offered was gorgeous, the valley stretching out before them with its river and town, rolling hills and woodland visible in the distance only as areas of black in the nights dark. He was sure If he’d given himself enough time to look he would probably have been able to pick out his own home down there among the lights, but something else caught his eye, giving him pause for thought.

"T-there’s other cars here?" He said a little meekly, eying the four other vehicles in the car park, some with their lights on, most not, all a good distance from them and each other.

"Don’t worry babe, they’re here for the same reason we are… Now then, where were you?" Shahira prompted, one of her hands going down to her side, allowing her to lean her chair further back, giving Casey more space to work with.

Smiling he took her spit-slick length in his hand and gave it a squeeze, feeling the now fully erect length fill his little hand, hot and throbbing, "I think I was about to suck your cock?"

Shahira let out a little chuckle and ran her fingers through his fine soft hair, "Kiss me first, come here."

He blushed but co-operated as she tugged him up and closer, his moist lips finding hers, soft moans passing between them as she eagerly deepened the kiss, allowing her tongue to explore his sweet mouth, feeling his own caress hers.

Though Shahira was sure no one was looking, she knew anyone watching would be treated to an erotic, if not misleading sight as the couple made out. To any would-be viewers it would appear at first glance to be an illicit interracial lesbian couple, a slender little flat chested white girl tongue wrestling a curvier and much bustier woman, noticeably exotic in her skin and garb.

The reality however, of a white boy femmed up to look like his sister about to give her girlfriend and his horny dickgirl lover a blowjob while she did what she wanted with his enticing bubble butt had so many extra layers to it that each one of them served to enhance the experience, making it all the more exciting for them both.

Despite their desperation to get back to the main event, her cock hard and straining, neither of them were racing to break out of their shared kiss. Instead their lips joined together time and time again as their tongues mingled freely, one of his hands moving to rest on her chest, settling under her jacket to cup one of her heavy soft breasts, squeezing it between his delicate fingers, feeling its alluring shape and warmth through her top and supportive bra as he kneaded it.

Similarly she urged one her hands down his back, prompting him to move from sitting on his cute butt to kneeling on the seat, bending over towards her as her hand worked up under the pleats of his dress, her strong hand finding and roughly squeezing one of his bubbly cheeks through his sisters pilfered panties, Casey moaning into the kiss in response.

After a few more intense moments had passed between them she pulled back on his hair, the boy letting out a little whimper as he was dragged away from the kiss, his eyes half-lidded, his tongue lolling slightly from his lips as they both breathed hard.

"Are you wearing panties?..." Shahira asked curiously and Casey nodded cutely, swallowing.

"M-my sisters…" He admitted, tone maybe a little defensive as he bit his lip, feeling her hand slip in under his lacey undergarments, holding his ass possessively.

She smirked some, "It’s not a problem you know," she started, trying to relieve his defensiveness, " It’s just you don’t usually wear them is all…"

He blushed and gave her a shy little smile, eyes sparkling, "They just… Feel right."

She let out a soft little laugh and kissed him again, though only briefly this time, her voice becoming soft and almost pleading, so genuine in her words that Casey blushed crimson, "You’re so fucking cute... I need you, Casey, I really, really need you right now, please...?"

He felt his heart skip a beat and he smiled brightly, his expression lighting up with such an intense and intimate joy that to Shahira it was like he was smiling with his very heart and soul.

To Casey the fact that this gorgeous goddess of a woman with her power, confidence, impressively hung cock and enticing bust genuinely needed him, a girly crossdressing white boy, meant so much to him. The mere thought of it, that he was worth so much to her, filled him with a confidence and warmth so incredibly overwhelming that more than ever he wanted to please her, to share with her the warmth her words had gifted him.

While not entirely sure what it was she had said to incite such an intense and intimate look from Casey, when he finally tore his gaze away, lowering himself back down towards her cock she found herself sporting a rare warm blush, uncertain if she’d ever had anyone look at her quite like how he just had.

Feeling a familiar warmth wrap around the cherry tip of her cock she let out a shuddering little moan, arching her back as pleasure once again flowed down from the sensitive head of her thick length to spread throughout her body, relaxing her as her hand played idly with his enticingly soft ass cheeks, her other hand interlacing into his natural brown hair, not guiding or controlling him, but caressing and encouraging.

Casey’s lips slid slowly up and down the slick length of her veiny cock, each push downwards again bringing the shiny tip deep enough to press against the entrance to his throat. While he knew, steely hard like she was and at the angle he was at, that there was no chance of him being able to take her back into the tight milking embrace of his throat like he really wanted to, he hoped the pressure of him trying to do just that would help to heighten her pleasure, as well as granting him the chance to practice suppressing his gag reflex, something he was keen to improve upon.

With her ears full of the lewd and carnal sounds that came with a slow but intense blowjob, the slurping, sucking, wet sticky noises, Shahira refocused herself and turned her attention across to his ass which, so far, she had merely been fondling.

To an approving moan from the boy working her shaft she pulled his skirt all the way up, revealing in its entirety his luscious panty clad ass, the black strip of fabric at the back of his panties practically vanishing between the globes of his cheeks.

With a shuddering moan she slapped his ass, feeling a spark of amazement flow through her as it always did when she watched the resulting bounce and ripple of his doughy cheek.

"You’ve got the best fucking ass Casey baby, I can’t wait to feel it wrapped around my cock…" She moaned, watching with glee as he purposefully arched his back down for her, enhancing the view of his ass, making it stand out all the more prominently against the rest of his figure.

Hooking a thumb under the waistband of his panties she pushed them away, trying to work the lacy fabric down over the swell of his ass, but, reclined as she was, she struggled to reach far enough to make any progress.

Not wanting to move and disturb the rhythm he’d set sucking her cock she spoke in a soft voice, caressing his hair gently as she did, hoping it would be enough to ensure he kept doing what he was doing while he helped her out, "Shove your panties down to your knees baby, I want your ass bare for me…"

Without missing a beat with his mouth and unable to move the hand that was supporting his weight between them, he moved the spit-slick hand from the lower half of her cock down under his chest and between his thighs, his ass wiggling from side to side as she watched the entrapped black strip of fabric break free from the hugging embrace of his cheeks to glide down over them instead, the snug panties falling down his thighs to rest around his knees, his hand quickly returning to grip and squeeze the base of her cock as soon as he was finished, loving the feeling of her textured cock with its veins and steely ridges in his delicate and feminine hold.

"Oooh, good girl…" She praised, moving her hand back to his ass as he shivered in pleasure, something that this time she didn’t miss, "Don’t tell me… You like it when I call you a good girl, don’t you?"

Words weren’t needed to convey just how right she was so he never stopped sucking her cock, instead, in lieu of an answer he moaned, a light girly noise that was accompanied by the boy pushing his ass back into her groping hand.

"Wow…" Shahira said, letting out a little laugh, "That’s so cute, fuck, well I won’t hand them out for free you know, you’ll have to earn them…"

For a moment he sucked hard on her cock, drawing a gasp from her lips as the bliss rolled through her, luxurious and wonderful, proving that he was more than willing to earn his praise.

She smirked and curled her toes in pleasure, watching and feeling in delight as he worshipped her girl-cock. This was just all too good.

Eagerly waiting for her to start toying his ass he gave it a little wiggle, the movement in her hand breaking her blissful immersion and drawing her thoughts back to his now vulnerable boy-butt.

"Oh, right, your ass." She said a little apologetically, realising she had been too easily distracted by the constant suite of sensations coursing through her cock to give his ass the attention it was so obviously craving.

After giving each of his now bare cheeks a squeeze she bit her lip, opting to slide a couple of her fingers down into the warm crevice of his ass. She enjoyed the soft warmth that enveloped her fingers as they sought her target, inching lower until they brushed against and came to rest on a small rubber disc that was seemingly resting on top of his virgin star.

"I can’t believe you wore this so much… Does it feel good? Do you like having something in your tight little ass baby?" she asked, and as if to emphasize what she was talking about she used her finger to tap the exposed base of his butt plug, sending a single pulse of sensation up into his ass, making him whimper in such a delightfully sexy way.

"Are you hard?" She asked, her fingers working the base of the toy in slow circles, stirring the bulbous bulk of the plug deep within his core.

With a shuddering moan and needing to catch his breath, he let her cock fall free from his lips, his breath hot against her skin as he whimpered in time to her stirring fingers, "Y-yes Shahira…"

Smirking she moved the hand in his hair to his face, caressing his blushing cheek and raising him so he looked at her, her voice sultry, "I knew you would be... I want you to stroke your cock for me."

He blinked up at her, eyes a little watery from the constant pressure on his throat, his lips forming a pink pout, confirmation at least that his lipstick was doing its job, "But I want to stroke your cock…"

"Don’t worry about me baby, your gorgeous little mouth," She started, tracing a thumb across his moist lips, "is more than enough to get me off... But I want you to feel good too. Please?"

He looked hesitant, but couldn’t deny his own cock was screaming for attention. She genuinely would’ve stroked him herself, not adverse to returning at least some of her boytoys lustful advances, but as it stood she could neither reach his length nor spare a hand, so she just smiled and nodded as if to say it was okay.

Staring up at her and drinking in the alluring features of her beautiful face framed in the distinct fabric of her hijab, he relented, nodding too and moving his hand from her cock which now stood straight up on its own, twitching in time with her heartbeat.

"Okay." He said softly and smiled, lowering his head back down, the slick length of her shaft brushing against his cheek briefly before he once again caught it in his mouth, returning to his pace with such a natural ease it was like he hadn’t even been interrupted.

Rewarded with the sound of her moans and her fingers one again lacing into his hair he let his hand move under his body, travelling down until his fingers closed around something so similar and yet so different.

While, like hers, his cock was hot, hard and twitching, his sticky fingers quickly wetting the pale length, it felt completely different to hold. Though his size wasn’t insubstantial, his hand, even when wrapped around the length, leaving a couple of inches of his cock free, when compared to Shahira’s hefty pole it left him feeling a little meagre, not that he, or Shahira for that matter, much cared about his size.

As he stroked himself, feeling his already slick grip grow more so as he massaged beads of pre into his length he felt her fingers pulling and pushing at his plug, each movement making him moan around her cock, sending little vibrations buzzing through the sensitive tip as she slowly began to work it free.

He whimpered cutely at the sudden discomfort of his star being stretched open, his tight ring hugging the plug as she pulled it back to its thickest point, letting him writhe for a moment at the intense sensation, assured by his mouth-muffled moans that at the very least this wasn’t causing him any pain.

She waited a few moments longer, moving the buttplug from side to side to try and get his little hole used to being so stretched, before, with a final tug, it came free of his ass, the boys back arching upwards briefly as his sensitive little star closed up, a surprisingly potent bolt of pleasure lancing up his cock as it did making him whimper.

Smirking, she set the used plug aside, producing another, larger one from down beside her chair which she raised to her lips, her tongue slowly and liberally coating it in her own saliva before she reached back down, beginning to feed it between his cheeks, pressing the tapered tip up against his star, which had only been given mere seconds to rest and recover.

Despite this he pushed himself back against the new plug as it was slowly pressed into him, eager to feel more as its increasing girth made him tingle all over with pleasure.

More than anything Casey wanted the moment to last forever. With her deliciously thick cock filling his mouth, drops of her pre coating his tongue, his bubbly ass taking her new toy with surprising ease and his own hand gliding along his throbbing cock it felt so good and so right.

But he knew he was too horny to hold out for long, too inundated with the intense rippling waves of pleasure that pervaded his body and too lost in the lewd thoughts of what would soon be swimming in his mind to properly control himself and to slow the jerking hand wrapped around his length. He was close, so very close!

With a smirk, and not knowing that he was on the verge of his impending orgasm, Shahira pushed with a suddenly increased force on the new thicker, longer plug, his star stretching obscenely wide for half a second to accommodate the new intrusion before the whole thing vanished inside him, filling him in ways he’d never felt before.

He whimpered suddenly as his cock spasmed in his hand, his moans, louder now than before betraying to Shahira that she had just made him cum, his lips enclosed tight around the crown of her cock as he sucked and swirled his tongue, trying to prompt her to join him in his sudden and powerful climax.

Not wanting to let up on the pleasure he was obviously in the throws of she tugged and twisted the base of his new plug, shifting it deep inside his virgin little hole as he came, her hand moving from his hair to the lower half of her own cock, stroking it quickly, her fingers bumping against his plush lips with each upward motion as she tried to push herself over the edge that she too found she was teetering on, just so close.

Fortunately for her, the all together pornographic sight of the gorgeous Casey cumming hard, moaning like a girl with both his holes full was more than enough to help her take the last few steps to bliss.

"A-ah, yes! Casey baby!" She panted loudly as her climax hit her hard like a hammer, the salacious finale occurring in their sex den of a car obscured to the outside world by the now steamed up windows.

Casey felt relief and joy flow throughout him as her cock was quick to shoot off the first thick rope of her pent-up load into his waiting mouth, the sticky hot mess greeted between his lips by his swirling tongue, trying to taste as much as he could before he instinctively started swallowing, knowing all too well from first-hand experience just how much cum she would be gifting him in the next half minute.

As she came into his waiting mouth, the sensations travelling up and down her rigid shaft overwhelmingly powerful, she had the absolute pleasure of hearing him gulp again, and again, and again, each distinct noise signalling that he was depositing yet another mouthful of her virile seed down into his stomach.

It took a little while, but finally she breathed hard as her climax began to subside, her cock, still hard in his mouth, trickling the last of her balls substantial contents out onto his waiting, tongue, happily sating the last of his thirst.

As she began to recover her whole body relaxed back comfortably into her already reclined seat, a few strands of her, apparently, raven black hair obscuring one of her hazel eyes, having fallen free of her hijab in the last few frantic moments of their desperate coupling.

Panting hard she stared up at the steamy windshield, unable to make out the scenic view in the valley, she instead turned her attention down to the other spectacular sight beneath her.

Though her cock was well on its way to softening and had only a few savoury drops left to offer, he continued to dutifully nurse her tip, knowing that so long as he was gentle with it in the fresh afterglow of her climax, he could still bring her a few more iotas of pleasure.

He was so beautiful to her then, so feminine and girl-like, but without so many of the reservations she had expected to come with it when he had first appeared to her dressed as his sister, anxious and shy.

She’d never have guessed when she first saw him that he would end up being so active and involved in what they were doing, having fully expected instead a shy, passive little thing that would need convincing and coercing at every single little turn, like those few others of his type she’d had in her past. Instead, and to her immediate surprise, she had practically been forced to become the one to set the slower pace between them, having to rein him in to ensure that his body was as ready and able to take what he was already practically begging for, her cock in his ass.

She lay there content, one hand resting on her thigh through her jeans, the other idly gripping one of his plush cheeks, just wanting to hold him as her cock shrank back. At the last he took her soft cock deep into his mouth, feeling the now pliable and flexible length easily slip into his throat as he wrapped his lips tight around the base, slowly pulling up and sucking hard, cleaning every inch of her shaft as she let out a final gasp, a wonderful little shudder passing through her as her now over sensitive cockhead was given its final dues.

Panting hard Casey rested his head wearily against her stomach, his eyes fluttering closed as her hand moved from her thigh to gently stroke at his long brown locks, neatening them back into place. She had meant for it to be comforting after what must have been hard work for her boy toy, but to Casey her touch was like a reward, each gentle caress triggering pleasant little tingles across his scalp, her attention, in any form, something that he knew he would always want for and crave.

She felt a happy little sigh escape her chest and she smiled. He was just so absolutely precious to her, she couldn’t even really explain it. But, it was in that moment as she looked down on him that she knew, without a shadow of a doubt, that, in the long-term at least, they would wind up with one another.

But she reminded herself that the long-term was still a while off yet. Until then, or until something changed, she would just have to keep playing this odd little game with Joanna. Besides, the thrill that came from her illicit sessions with Casey and the way he always looked so much like his sister, if not a little sexier in her opinion, she had decided was well worth the risk of being caught out and the cost of her continued presents to Joanna.

Thinking about the short term she glanced back and to the side curiously, suddenly very aware that the boy had cum in her nice clean car and, as a result, she half expected to find the divide between them dripping with his viscous white stuff, but, she was pleased to see that at his own moment of climax he had pointed his cock straight down, his own substantially more diminutive load mostly soaking into his sisters lace panties, the drop or two that had landed on her seat nothing to cause a fuss about.

She smiled proudly, he was just so considerate, though she knew she’d have to keep the soiled panties for herself. In part so Joanna wouldn’t find out that he had cum, something that would definitely have given the game away, but also as a sort of trophy, a reminder of the evening and something to wrap around her cock and jerk off with later, thinking of Casey while looking at a few suggestive pictures of Joanna.

She squeezed his ass and he let out a contented little purr of noise, almost asleep against her she realised as they embraced, both spent, satisfied and in the best company either of them could wish for.

She looked down at his ass and admired it for a moment, knowing that held deep within it was the key to what came next. If he used the plug enough, which she was sure he would, then in just a few days, his body would finally be ready for her.

She smiled at the thought, her mind drifting as she wondered how it would all play out... She wasn’t sure, but she could wait, it wouldn’t be long after all, though it might feel like forever to Casey.

For now though, there was only one thing left to do before taking him home and dropping him off to debrief his sister. And she had no doubt that he’d earned it.

"Good girl." She whispered softly.

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Pub: 20 Jan 2024 19:42 UTC
Views: 286