[Sissy, Chastity]

“S-Sis, do we really have to do this?”

The voice of a young man who honestly wanted everything to just go away, echoed through his room. For good reason too, considering his sister was currently pulling down his pants and examining his manhood with a surprisingly keen eye.

“Of course we do, Noa. If you go out on a date without a little bit of security, then you’re just going to end up getting drained. In more ways than one.” The boy’s sister, Samantha Natsume, chimed as she gently flicked his thumb-sized prick with one of her fingers. “Especially considering the size of your thing, how come it never grew?”

Her brother, Noa Natsume, gasped and panted as a little bit of pre started dribbling out of the tip of his thing. “S-Stop that, Sis. It’s super sensitive…” He mumbled and muttered, his body shaking and shivering in her presence. Partly because he knew what would happen if he talked back to her, and partly because having her this near was enough to make him start growing aroused…

“Nah. If I stop, you’ll just grow hard anyway.” Samantha shot his pleading down as she slowly and carefully stroked her fingers along the length of his prick, giggling as it splurted out more of that clear substance. “Good grief, I’m glad that I’m the one who picked out your date, I’m not sure how you’d be able to stay dry if you had to meet somebody I didn’t know…”

Thanks to her continued teasing and the way that she just didn’t want to let him take a moment to breathe caused the boy’s cock to slowly stand up straight, growing proper erect for what felt like a brief moment, only for more of that goo to fire out as he had quite the immodest and impromptu orgasm. Once it grew limp, however…

*Click*

When Noa regained his clarity of mind, he found his poor little thing snapped shut inside a brass cage, one with a couple of gaps that let him look at his sausage trapped within. And the one with the key was his beloved sister, who snuck it in between her breasts. “S-Sis, you can’t be serious…”

“Noa, you just came all over your lap. I told you this when I said I’d arrange you a date, I don’t want you making a mess outside. This is the only way I can guarantee that. Otherwise, you’re just going to come home and make an even bigger mess.” Samantha shot back, patting her little brother on the head as she snuck a kiss onto his cheek. “You have to trust me, okay?”

The younger brother slowly looked back up at her before nodding. “I… I trust you, Sis. But… You never told me what my date’s like. I saw her photo on the internet, but…” He paused, feeling his cock gently throb within his cage thanks to how the cold brass rubbed up against it. It made him enjoy it, whether or not he really wanted to.

“You’ll be surprised when you swing by the place I’ve booked. Trust me.” His sister chimed, quietly dancing around the topic of his date’s gender as she giggled. “Now, get dressed. Try on some of my old shorts or that tube top that barely hides anything. You wanna make a great impression, right?”

Noa’s face quickly flushed further red as he nodded, going over to his cupboard to pick out a couple of clothes for himself. Shorts that left little to the imagination, that even began to bulge a bit in the front thanks to the new addition of his cage, and a tube top that adorably said “JUICY”, ready to wrap around his flat chest and emphasize it.

Samantha clapped as he walked over, prompting her to give him yet another kiss on the cheek. “Now, remember, Noa? Don’t blow your load. If you come back home and I find these pants wet, you’re grounded for the next week. And then I’m gonna have to vet every single date you go on for the rest of your life.”

“Y-You can’t just… Sis, please…” He mumbled as she remained authoritarian over him, pouting as she ran a hand through his hair. He knew it was for his own good. That was why she had enacted so much control over him since he was younger.

He just hoped that his date would go well. Then he’d have something fun to talk about when he came home at least.

---

“Where is she..?”

After finally making it to the park where he was supposed to meet his date, poor Noa couldn’t find the girl that he had been looking for. And it shouldn’t be hard to find her, since she was supposed to be wearing a big yellow sundress, kind of like the boy with the big hat over by one of the tables…

“Excuse me?” The young provocatively dressed boy approached the table, shivering as he looked down upon the boy with the wide-brimmed hat. “Y-You wouldn’t happen to have seen a girl dressed kind of like you? I think her name was…”

The hat-wearing boy giggled as he lifted the hat off his head, putting it down on the table to reveal the long blonde locks that reached all the way down to his knees. “Noa Natsume, right?” The boy chimed, his voice ringing through the booty-shorts-wearing boy’s ears like a set of harmonic bells.

“H-How do you know my name?” Noa asked, shivers running down his spine as he took a seat across from the strange boy. It’d be better to get an answer out of him while he was waiting for his date to arrive…

The crossdressing boy giggled as he brushed a hand through his hair. “You’re waiting for Mayume Ritsuko, yes? Well, you happen to be looking straight at him.” He said with a bunch of pride running off his lips, only for them to purse together as he pouted. “I can’t believe that you couldn’t recognize my looks, Noa. I sent you a bunch of pictures too!”

“M-Mayume?! B-But, you looked like, I, I’m…” To say that the femininely dressed boy was surprised would be a gross and inaccurate understatement. He was horrified that he hadn’t realized it, quickly pressing his face down against the table. “I’m so sorry, I’m so sorry, I didn’t mean to make it sound like I wasn’t respectful!”

His would-be-date laughed in the face of his adorable inability to relax. “It’s fine, Noa. I’m just surprised you didn’t notice any of the settings I had turned on. Really, thinking that a boy as cute as me is a girl. You’re so silly, maybe that’s why your sister treats you the way that she does.” Mayume chimed, rubbing his hands against his cheeks as he kept on grinning and giggling.

“M-Maybe… Maybe that is why, I can’t believe I wasn’t able to tell. I’m so sorry, Mayume. Is there any way that I could…” Noa kept on apologizing, only to notice that the boy had suddenly disappeared from his sights. “M-Mayume? W-Where are yooUUUUU-”

Worries quickly vanished from his mind as he felt a hand wrapping its way around his chastity cage, another feminine giggle echoing from below. “Oho, I see Sammy’s been a good girl all this time, teaching you the same things I’ve been taught!” The feminine boy gently rubbed his fingers all over this priceless piece of brass, panting and gasping as he wanted nothing more than to play with it for so long…

“T-Taught? What did she teach you? W-What do you mean? E-Explain, please, I think I’m going to get dizzy if I don’t understand…” The shorts-wearing and chastised boy gasped again as he felt the metal brush up against his rod, a few throbs making it clear that he wanted to cum already, but he couldn’t…

Mayume popped his head out from underneath the table as he carefully rubbed his hands up against the boy’s thighs. “So, there’s a different reason why your sister decided to stuff you in a cage, and trust me, it might sound weird…” The blonde boy explained, pushing the table away slightly as he climbed onto his new friend’s lap, letting his breath brush up against his neck and put him on edge as a result.

“It’s because once you get locked up, and it gets neglected for so long… It’ll blow its load as soon as you touch it. And if Sammy’s anything like when she dated me and made me into a total cum-loving sissy, she wants you to be just like me.” He whispered, as he slowly tugged up his sundress to reveal his own chastity, though his was basically nothing more than a ring wrapped around the base of his cock with a terrifying lock attached. He didn’t even wear panties, going commando despite the risk it posed to somebody like him.

Noa slowly looked at the thing in front of him, panting and gasping as that sissy-sized cock was throbbing, yet it remained as limp as ever. Even as it drooled out droplets of cum that spilled onto his thighs. Even as it threatened to cum right then and there.

“Go on. I know you wanna touch it, Noa. But if you do, you know where you’ll end up, right? Right between your sister’s legs, just like I’ve been. Who knows, maybe she’ll like the two of us down there instead of just one sissy?” Mayume giggled, slowly rubbing his hands up against the boy’s cheeks. “What do you say? Do you wanna take the plunge?”

The boy couldn’t find the words to say no. Nor could he find the ones that would turn him away. All he could do was slowly reach his hand forward, putting those gentle fingers onto the sissy’s prick…

His gentle touch, nothing more than a tiny squeeze, was enough to make a general dollop of clear seed slowly but surely drool out of the blonde sissy’s urethra. He didn’t even say a thing, just letting it cum out on its own. That was the proof of his sissyhood. The proof that he couldn’t his cock like a proper man. He was blessed with a life of drooling everything out in the hands of another…

Just like Noa. The boy was practically drooling whenever he looked at his sister, waiting for her to give him the orders that would let him live his life. If this was the end result, where he’d be locked in a cage or with a tiny ring that’d keep him from getting properly erect, then…

The cock-caged boy let out a moan as a bit of drooling cum slipped out between the holes in his cage, his face turning as deep crimson as it possibly could. The thought of submitting to his sister in more ways than he already did was enough to bring him to a climax, and it was only amplified by how neglected his thing had felt ever since he got locked into the cage…

“I warned you, Noa.” Mayume giggled as he wrapped his arms around the poor boy’s back, kissing him again and again on his cheeks, showering him in affection as his own rod started rubbing up against the caged one, his immodest and near-silent orgasms growing in number as the ground beneath them grew wetter by the second.

Noa lost in pleasure. His cock was drooling alongside his new friend, as his mind was going on a bit of a trip thanks to the affection displayed by the sissy on his lap. He could imagine his dearest sister kissing him just like he was, whispering lovely commands and guidance into his ear, just like always. But this time, she’d be straddling him, pushing her nethers into his cage to tease him further and further. And every time, he’d cum harder and harder…

He could only imagine how much better it’d feel, once he’d descend further into sissyhood with Mayume by his side...