Casey was sat cross-legged on his bed with his laptop open before him when he heard the familiar and teasing cadence of his sisters voice. Surprised by her presence he looked up from his laptop towards his open bedroom door, taking in the sight of his sister stood there, leaning casually on its frame, the hall’s lights spilling into his room around her like an aura.
She smirked as she held up her phone, wiggling it from side to side, showing him the most recent text message on display from her girlfriend, Shahira.
“Come on sweetie, let’s get you nice and ready for her!” Joanna winked and motioned with her head back towards the way she’d come from, turning and walking away, trusting that he knew better than to ignore the beck and call of the hijab-clad dickgirl.
Biting his lip Casey locked his laptop and stood, walking quickly after his sister, his voice quavering a little as he caught up, almost coming in at a whisper, “B-But mom’s in…”
“Mmhm,” Joanna smirked glancing at him as she swung open her door, holding it politely as she waited for him to step in ahead of her, eying him over as he did so, noting that his gait was a little off, probably because he’d been sat cross-legged for so long on his laptop, she figured.
“That’s what I said to Shahira too,” She continued once he was inside, “but she wants her dick sucked and you know what she’s like when she gets riled up soooo…” she shrugged and smiled a little too sweetly, “I guess she’s going to take you for a little drive.”
Casey blushed as he sat himself down demurely in the chair before her vanity mirror, swallowing as she fetched a hairbrush and began to smooth out his long brown hair, admiring its soft glossiness as it flowed between her fingers, the activity of preparing him for Shahira almost routine for them both now.
“Wait, so… I’ll be alone with her? Completely?” He asked meekly, looking up at her in the mirror’s reflection, his dark doe-like eyes wide.
Joanna smirked some and nodded, eying him back, “Yeah I guess so? And don’t be so nervous Casey! You’ve done this what? Eight, nine times now?”
“This will be the eleventh…” He replied softly and Joanna snorted out a little laugh.
“Keeping count?” She asked smugly, clearly bemused, his gaze meeting hers only briefly in the reflection of the mirror before he blushed shyly, not responding as her smirk broke into a knowing grin, “Eh, can’t say I blame you I guess, but still, you’ve done this enough times now you really should stop feeling so anxious. It’s just another blowjob after all. And I mean It’s not like you don’t know what you’re doing at this point…”
He took a deep breath, letting it out in a long quivering sigh as he stayed quiet, not engaging her in an effort to avoid more of her snarky little comments. Besides, for all her smugness she had it all wrong, not that he was going to correct her anytime soon.
Sure, he was both anxious and nervous like she had said, he couldn’t and wouldn’t try to deny that, but Joanna believed it was born of embarrassment, humiliation and maybe even a little fear. After all, she was forcing her cross-dressing brother to dress up like herself and blow her hung girlfriend, something she herself refused to do because it was in her mind ‘icky’, so why wouldn’t he feel that way?
What she didn’t know however was that his anxieties and nerves stemmed from something completely different, something Joanna hadn’t even considered. He was excited, genuinely so. From the moment the words ‘booty call’ had left his sisters mouth he’d been buzzing on the inside in anticipation, the fact that for the first time they’d be really alone, without the chance of any prying eyes or ears from Joanna, just added to his expectations.
He watched as she applied her makeup, the subtle differences between their feminine faces vanishing as she worked and he couldn’t help but look at the makeup kit she was using, noting it was one of the many gifts bought for her by Shahira and yet another little secret they held. Shahira may have given the kit to Joanna, but he knew she’d really bought it for him.
The very first time Joanna had forced Casey into this little arrangement, threatening to expose evidence of his cross-dressing habit to their mom if he didn’t cooperate, Shahira had figured him out almost immediately. She had managed to work out Joanna’s deception before his lips had even touched her cock and, instead of getting angry or just leaving, she’d told Casey to play along, to let Joanna think she was getting away with it just so she could keep playing with the fun little femboy.
While Joanna had had to coerce and force him into it the first time, he’d become incredibly glad that she had. The experience had been nothing short of life-changing for him, the event showing him just what he had been missing all his life, something that now he couldn’t get enough of.
“Lips,” Joanna said, derailing his train of thought as he pursed his lips obediently, watching as she applied a pink lipstick, soft matte, something Shahira had specifically bought for him due to its apparent blowjob-proof qualities.
Once she was finished he smacked his lips once or twice, his mind finding a new track to focus on, this one causing him some legitimate worry, “How… How am I going to get past mom?”
Joanna let out a soft, “Hmmm,” as she picked out a cute top, “I’ll go watch TV with her, she’ll hear you leave the house and come back but she won’t see you so… I’ll just tell her you went to Johnny’s to help him out with some computer stuff.”
He nodded a little, figuring that would work, “O-okay. Is there anything I should know? Have you and Shahira been discussing anything recently?”
She shook her head for a second, picking out a skirt and some heels, “No, nothing that really stands-…” She paused, staring at nothing for a moment before turning, “Well, actually yeah kinda.”
Casey looked over at her curiously, his perfectly sculpted eyebrows raised.
“…She’s been talking about taking it further, you know, more sex stuff. Nothing much, just in passing.” Joanna explained as she laid out the clothes, beckoning to Casey with a finger, prompting him to get ready.
Casey stood and stepped towards the bed, eying the outfit she’d picked for him with an almost critical eye, wanting to make sure he looked his best for Shahira. The top was solid in colour, the same shade of pink as his lipstick he noted, the v in it shallow since both Joanna and Casey didn’t have any breasts to really show off. The sleeves were cut to just above the elbow and, he noticed, the length was rather short meaning it would leave an inch or two of his smooth flat tummy on display.
The skirt was a simple black pleated item, and while he knew Joanna wished she could put him in shorter, more slutty stuff, she had to make sure his extra package wouldn’t be easy for Shahira to discover. Pretty ironic he thought, since Shahira would likely appreciate a sluttier outfit on his lithe form.
“What should I say if she asks me about that?” He said as he started to remove his clothes, tossing them in a heap as he stripped down to his briefs, having done this enough to no longer feel embarrassed about being so on show in front of his own sister.
Joanna folded her arms and eyed him up and down as he revealed his stunning figure, slightly jealous that her brother could look just as dazzlingly feminine as she could with virtually no effort, despite how useful it had proven to be, “Just be evasive.”
Casey glanced at her as he worked the pleated skirt up over his wide hips, “She’ll keep asking you know?”
Joanna let out a little sigh, “Yeaaah, I know. I might have to actually put out… Maybe once every month or two, let you fill in the rest with blowjobs.”
Casey worked his arms into the sleeves of the top and pulled the figure-hugging fabric on over himself, careful not to smudge the expertly applied makeup that, in retrospect, he guessed they should’ve done after he was dressed. He’d have to remember that for next time, after all, he did want to look his best for Shahira.
“Well it’s definitely not something I can help with,” Casey said seeing an opportunity, filling his voice full of a confidence that he knew would annoy his sister, “It’s not like I could blindfold her and use my ass. You’ll just have to put out.”
He glanced across at his sister who narrowed her eyes then smirked slightly like he’d just given her an idea.
He had to stop himself from smiling, he didn’t want to give away that it was exactly what he wanted.
After getting him into his heels, in which thanks to his years of cross-dressing practice he could walk in with ease, they stood in front of a tall mirror, Joanna fussing over the little details, making sure his hair was straight, his makeup was fine and he was overall, ready.
As she adjusted his top, making sure it sat evenly with no creases across his flat chest they both heard her phone buzz. As she fished it from a pocket he felt his heart hammering in his chest, leaning over to catch a glimpse of the screen as she unlocked it, a new message from ‘Bae <3’.
“I’m outside x”
“Alright!” Joanna beamed, happy with her work, the slender Casey looking more like Joanna and more feminine in his full makeup and outfit than even she did, dressed for a casual day in the house as she was, “I’ll go distract mom, you ready?”
Casey bit his lip for a moment, “I er, can I borrow a pair of your panties?” He asked.
She rolled her eyes, “Ugh do you have to? You know I don’t like you wearing them!”
“Well I can’t wear boys underwear, you know what she’s like for wanting to squeeze your, or my butt.” He said defensively, “And I can’t go commando in a skirt, I need something to hold my dick in place…”
She eyed him levelly for a few moments, her cheeks puffed out as she thought, clearly displeased, eventually though letting out a deep theatrical sigh, “Jeez, alright, fiiine.”
She walked to her dresser and selected a lacy black pair, noting his own boyish underwear pooling around his ankles when she turned back, his ‘goods’ obscured by the dress as he stepped out of the briefs, nudging them into the heap with the rest of the discarded clothes.
He took the offered panties and stepped delicately into them, unable to hide his blush as he worked the fabric up over his silky skin, enjoying the feeling as he worked them into place, the dark fabric snuggling between his bubbly cheeks and tucking his package away for safekeeping.
“Now are you all good?” She asked in a tone of voice that expressed that yes, he was, regardless of what he thought.
He nodded and she let her eyes drink him in one last time, “Wait a couple minutes before you go downstairs so I can make sure moms out the way. Oh, and here.”
She took out her phone and passed it to him, “It’d be weird if you didn’t have it.”
He took the phone and, with an absolute shortage of pockets to put it in, simply held onto it, nodding a little, “Okay.”
“Do a good job,” she said as she turned, walking out of her room to leave him alone, glancing back only briefly, a smirk on her face, “Or else I’ll talk to Shahira about blindfolds.”
He was glad she had left immediately after what she must have assumed was a good threat because it meant she didn’t see the blush that glowed on his cheeks at her words. He was also pretty glad she’d left before she got to see him walk again since his gait was still a little weird from the thing and he was worried she was noticing…
He only managed to wait a minute or so before stepping from her room, eager to proceed. Sneaking quietly he moved downstairs, listening carefully for any telltale signs that Joanna and his mom weren’t where they were supposed to be, but, only hearing the sound of the TV and not keen to loiter around he opened the door to the house and stepped into the cool evening air, the only light in the night those from the windows of his house, a smattering of yellow street lights and a pair of headlights, waiting for him.
Stepping towards the car he saw Shahira watching him, a sly little smile forming on her face as he crossed his steps, emphasizing the flow of his hips and the length of his legs for her enjoyment as he approached.
Unable to suppress a smile himself he stepped around in front of the car towards the passenger side, feeling her eyes on him the entire way as his footwear clicked on the tarmac, the heels helping to make his body, from his calves to his ass, look all the more womanly and defined, though he knew the skirt was hiding her favourite bits.
“Hey, cutie.” Shahira all but purred, her voice rich in a none too subtle desire and her own vibrant accent which he had grown to adore.
“Hey yourself.” He said, matching her tone and putting on his most feminine of voices as he settled into the passenger side seat, putting Joanna’s phone away in the glove side compartment, “Miss me?”
She smiled broadly, her hazel eyes sparkling as she leaned in, seeking his lips with her own.
Casey felt all his breath catch in his throat and his anxieties melt away as they kissed, albeit briefly. After a moment Shahira leaned back, eying the girly looking boy with glee, he was as beautiful as always and was blushing like a bitch in heat.
“I’ll… Take that as a yes?” He said with a smile, buckling in as she started up the car.
“You better believe it…” She eyed him hungrily for a moment before turning her attention to the road, pulling away from the house in her automatic and out into the night, “How’s my favourite little cocksucker been, hm?”
“I’ve been okay, but I’ve missed seeing you.” He said honestly, his eyes travelling up and down her figure.
She was just so gorgeous. Wearing jeans as she usually did, her curves and impressive bust were complimented by a red button shirt and a long-sleeved leather jacket that she wore open, her hijab sporting a black and red floral pattern that tied the whole ensemble together.
“It’s only been four days since my last booty call,” She said with mirth in her voice, obviously pleased by just how much he wanted her, “or is that too long for you now, Casey?”
He blushed brightly as she used his name, having always used Joanna’s in the past just in case his sister had been lurking in the background.
“It feels like it’s been forever…” He admitted, smiling shyly then glancing out the window, “So um… Where are we going?”
Shahira blew out her cheeks, “Well… I -had- wanted to take you back to my place, but my roommate is home and I don’t want you to meet her just yet,” She paused, concentrating on her driving for a moment as she came to a junction before continuing, “so I’m just taking you to a nice quiet spot where we won’t be disturbed.”
“Is it far?” Casey asked, curiously.
“A little.” Shahira replied, her eyes flickering from the road to his face for just a moment, “Good choice of lipstick by the way, you look gorgeous…”
Casey smiled, utterly flattered by the compliment, his voice shy but pleased, “I mean Joanna picked it but… I’m glad she did.”
“Mm, it’s going to look great wrapped around my cock.” She teased and Casey smiled broader.
“I hope so…” He sighed warmly.
They drove in silence for a few minutes, Casey looking out the window at the passing buildings, growing increasingly more sparse as they left the busier hustle of the town. He looked over to her again, his eyes taking in every gorgeous detail of the face he’d come to fantasise about so often, her makeup subtle save for her eyeliner, striking as always it drew attention to her hazel eyes, their depths so gentle and caring but with an undercurrent of something else he’d come to recognise.
Despite how invested she was in Casey and how much she enjoyed spending time with him, the booty call wasn’t so she could spend time in his company, she was horny and he could see it written across her face.
“Joanna mentioned something before…” He said to fill the silence, drawing a curious little noise from Shahira, indicating he should go on, “She said you’ve been pushing to do more? To have sex?”
Shahira nodded as if she had been expecting this question, “Mmhm, I don’t know how I’m going to manage it yet, but you know I want your ass. Got to make sure Joanna knows it’s coming so she can, hopefully, pass it along to you somehow.”
“I um, think I had a good idea about that,” Casey started, fidgeting his fingers together a little anxiously, “I know she’s not super keen to do anything, so I maybe goaded her a little, saying that she’d have to put out, because um… Because ‘it wasn’t like I could blindfold you and use my ass’.”
Shahira glanced his way briefly and grinned, her laughter coming out warm and rich, the sound washing over Casey to quell his anxieties, “Wow Casey, you really want it bad, don’t you?”
He blushed, “Y-yeah, I kinda do. I’d do it today if I could…” He said voice edged with hope as he looked her way, smiling a little slyly.
“Ha!” She laughed again, bright and vibrant, “Fuck, Casey, I wish I could, but you’re not ready yet. Almost though.”
He heard the reassurance in her voice and pouted anyway, “I’ve had the thing in all the time, are you sure I’m not ready?”
She shook her head, “I’m sure, if we did it tonight it’d hurt more than it should, I want your first time to be special, I want you to feel nothing but pleasure.”
“I don’t mind a little pain…” He said defensively but she shook her head.
“I mind.” She said simply, then hesitated, thinking back a few seconds, “…Did you say you’ve had the thing in all the time?”
“…Are you wearing it now?” She questioned.
“Of course.” He said, a hint of pride in his voice and she glanced over at him again, her full lips curled up into a smile.
“So, when you were getting ready with Joanna…?” She pressed, already knowing the answer but wanting to hear it from him anyway.
“I had the butt plug in, yes.”
“That’s really hot Casey…” She said, her voice heavy with desire and Casey watched as she wriggled slightly in her seat, parting her thighs ever so slightly, “I’ve got the last one with me, use that and in a couple days… Well. We’ll find an excuse to pop that cherry of yours.”
Casey nodded softly and felt a similar, if not smaller, bulge begin to fill out his sister’s panties. The thought of the two of them together, properly fucking had them both swelling in their respective underwear.
Casey cleared his throat, “Are… Are we almost there?” As he looked around he saw there were virtually no buildings, their car snaking up one of the hills that surrounded the valley town making for a destination he clearly had no clue about.
“Another five minutes,” Shahira said and Casey chewed his lip. Five minutes was a long time…
He shuffled in his seat, “Can I um…” He hesitated for a moment, considering the seatbelt across his chest, but found he wasn’t dissuaded by it, “Can I maybe start now?”
She raised her eyebrows and let her gaze flicker to him for a moment, It wouldn’t be the safest idea, but with the gorgeous boy sat there, his doe-like blowjob eyes watching her, wide and hopeful, his plush lips painted a beautiful shade of pink, the offer was far too tempting to refuse.
“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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3 thoughts on “Hot Chocolate Ch.02”
Thanks Tina for picking this story for me. It’s so fitting for another sissy girl like me. I loved it so much
Your stories make me so horney, for cock
And she’s just sooooo hot haha Xx