Hot Chocolate

"Booty call."

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?"

"Pretty much?"

"...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.