Falling Into the Rabbit Hole

"Falling into the rabbit hole."

Hey again!!! Sorry I haven't posted anything new from My Hypnotized Sissy Son--my mind just went totally blank whenever I tried to keep going with it. But anyway, I'm working on the second part now! Already hit 2,306 words, so... that's something, right?

Okay, so before we start this, I just wanna give a quick heads-up about this story to avoid any side-eye from Literotica's mods.

I really LOVE shady shit--I've always been into non-con kinks, especially those where're medical kinks, hypnosis, feminization, findom, degradation, you name it. But here's the thing: I'm weirdly OBSESSED with digging into how characters actually react to all that horny horror.

So, you know, this isn't one of those violent stories where Nick (our protagonist) gets brutally abused and actually forced into a bunch of terrifying situations as he descends into the abyss. Yeah, this story starts off dark and a bit depressing, but soon, like the rest of LT's stories, he's gonna to love it! He'll just take the long way home to end up exactly where he always wanted to be. So, yeah, this story is a bit dark, but not that dark, you know? Aaah who cares, you've been warned. Bye.

Warning:

This story is pure fiction, just like all its characters. Everyone in it is 18+ and should not be mistaken for minors. Also, fair warning--because of its content, no one should actually read this.

1. Nick.

Nick was a reckless boy who chased cheap thrills online, desperate for any scrap of attention. His dating apps were a graveyard of failed attempts to seduce some gorgeous MILF--most matches ghosted him instantly. The last girl who replied had done so by accident, but Nick, ever the optimist, clung to that glimmer of hope. When she vanished, he spent the night jerking off to her half-blurred photos.

A socially awkward weirdo, Nick hid his insecurities behind a screen. High school had ended over a year ago, and college was a pipe dream--why bother when he could binge games and nasty porn in his dingy bedroom?

On his 19th birthday, his mother shoved a duffel bag into his arms, dragged him to the door, and hissed, "Maybe your useless father will make a man out of you." The slam of the door echoed louder than her goodbye. But his father's house offered no refuge--He was just a distant man who drowned his regrets in whiskey and overtime. Left to scavenge fridge scraps (stale pizza, congealed takeout), Nick survived on greasy leftovers and the occasional crumpled bill tossed his way when Dad was too drunk to remember he had a son.

That was Nicky's life. He spent his days holed up in his room, glued to his laptop--gaming, scrolling, and devouring the three terabytes of porn stored in his hard drive.

Then he met Stefany.

It was a Saturday night, and he was deep into his usual Tinder mommy hunt. His rules were simple: age range set to 35--50, search radius 50+ miles. Every time he stumbled upon a hot mommy profile, he'd stroke his little pinky cock like a possessed--sometimes with his hand, sometimes with his Mia Malkova fleshlight (a drunken gift from Daddy))--edging himself just before climax to avoid a creamy mess. If the woman met his standards, he'd send a heart. If she was a perfect 100/10, he'd even pay for a DM. Swipe. Repeat.

At first, he'd sworn no to cum until one of these milfs replied--but that rule didn't last long. Otherwise, he'd be blue-balled for eternity.

An hour in, swiping through an endless parade of profiles, his cock twitched to life when hers appeared.

Stefany. 43. Single for a decade. Mother of two.

Her first photo nearly made him explode.

Tight black dress. Thigh-high boots. Makeup so sharp it could cut glass.

Her hazel-brown skin glowed under the screen's light, her mesmerizing brown eyes. Full, wide lips, begging to be bitten and put to work on a fat black big cock. A pixie cut that framed her face like a sin.

Nick's eyes locked onto the screen, drool pooling at the corner of his mouth.

Her double-D breasts were strained against her dress, the cleavage so tight they threatened to spill free. Hips wide enough to grip. Thighs thick, toned, begging to be spread. And though she wasn't turned around, he knew--her ass was twice the size of his head.

It had to be his lucky day. That slut was perfect goon material, he thought. Nick placed his phone on its stand, grabbed his fleshlight, slathered on extra lube, and prepared to spend the next hour worshiping Stefany's irresistible curves.

Thirty minutes later, he was a leaky, overstimulated mess. His cock had long since softened, and his fleshlight was filled with a slick mixture of lube and three thick, still-warm loads. He grabbed his phone, took one last longing look at the perfect MILF on his screen, and sent her a text--a hopeless gesture, he knew. Women like her didn't reply to guys like him.

He switched off the phone, dropped it onto the desk, and slumped back in his worn-out gamer chair, exhausted. But just as his breathing steadied, his heart lurched--the Tinder notification tone chimed. He snatched the phone, pulse racing.

It was her.

2. Stefany.

Stefany: "You're a bit too young to be interested in mature women, right? I could be your mom, honey!" She added a couple of heart emojis to soften the tease, letting Nick know she wasn't scolding him--just playing along.

Nick: "Hey! Thanks for getting back to me!" His reply was eager, almost too enthusiastic. "I'm not that young--I've dated plenty of mature women, to be honest. Love how sexy they are. And you? Damn." He cringed at his own words. The last woman he'd talked to was a cashier at the mall, and even she'd barely glanced at him. "Anyway... want to meet up? You're in Jackson, right? We could find somewhere halfway?"

Stefany: "Aw, you're sweet, cute boy. But isn't this a little fast? I don't even know you yet." Another pair of hearts punctuated her message, the digital equivalent of a playful wink. "What if you're some kind of charming weirdo?" Nick grinned at his phone. "I'm doing it!" He thought.

Nick: "Hey, what about a video call? That way we can get to know each other, and you'll see that I'm not a weirdo or anything."

His cock twitched again as he hit send. He glanced around his room--dirty clothes strewn across the floor, his fake pussy still glistening with lube and 3 hot-cumshots deep inside, the AI-posters of Bryce Dallas as a cheerleader and Margot Robbie in blacked lingerie (both tongue out, eyes rolled back) staring down at him. Yeah, definitely not a weirdo.

Stefany: "A video call, really? I don't feel comfortable enough with you for that." Nick was already stroking himself, his gaze locked on Stefany's profile picture--a teasing smirk, curves outlined in dim light topped with an almost phosphorescent lingerie set. Her next message popped up: "What if you're just some creep trying to get off on me?"

Nick: "How about I turn on my camera and you just watch? If you're comfortable... you can turn yours on too."

A pause. His pulse throbbed in his ears.

Stefany: "Fine. I can do that." His hands shook, cheeks burning. He'd actually pulled it off.

Nick: - Holy shit!!! - He screamed. "Cool, cool!!! I promise I won't be weird! So... now?"

The reply took seconds, but it felt like hours. Then--a link.

Stefany: "I'll see u there, sweetie."

Nick bolted from his chair. Dirty clothes were kicked behind the bed, sheets yanked into something resembling order. He scooped up trash, tossed the fleshlight into the shower (where it landed with a wet wap), splashed water on his face, and tugged his T-shirt straight. One last breath--calm the fuck down--then he pasted the link into his laptop.

The site loaded: Interview. No logo, no tabs--just a black screen and a single button: [START STREAM].

Stefany: "I'm waiting for you, babe."

His throat tightened. Fuck it. He clicked.

The camera flicked on, exposing his room--and him. Red-cheeked, awkward smile, fingers drumming the desk.

"Hey? Hello, Steff? Can you--can you see me?" No image. No hint of her. Just his own face staring back, wide-eyed. Then--her voice. Honeyed, playful, laced with something hotter.

Stefany: "Awww, honey. You're such a cute boy! Those cheeks..." A soft laugh. "But what's wrong, sweetheart? Scared?"

"No, it's just... this is weird. We should've used Skype." He squinted at the screen, searching for any trace of her. "I can't see you. How does this even work?"

Stefany: "Mmm, don't worry about that. We had a deal, remember? You show me... and I don't. Unless--" Another laugh, velvet and teasing. "--you're very good."

Nick was so starved for female attention that even the sound of a woman's voice was enough to make him overlook the glaring red flags.

"Oh, yeah... It's ok, really! And you're so beautiful--I loved all your photos! And you're from Jackson? That's only an hour away by bus. Maybe I could visit you sometime, or you could come over? I'd cook for you, take you out for coffee... What do you think?" His words tumbled out in a rushed stream, his excitement making him oblivious to how desperate he sounded.

Stefany: "What a sweet boy you are," She cooed. "I bet girls just adore someone as cute and thoughtful as you." Nick's heart fluttered. Girlfriends? The closest he'd ever gotten to a girl was the cashiers at the mall--and his mother.

"Aah... well, yeah, I guess so... I mean, some girls are nice, but others just care about money or some gym-rat guy. Whatever." His voice wavered slightly. He didn't want her to figure out he'd never actually had a girlfriend.

Stefany: "Aww, sweetheart..." Her voice dripped with playful sympathy. "I know, some girls can be mean like that. But not all of us, hm?"

Nick couldn't stop the grin spreading across his face, his chest buzzing feeling on a cloud nine. Today was definitely his lucky day--he'd cleaned his room, matched with an actual goddess, and now here she was, talking to him!, sounding like she actually cared!

Two hours in, and Stefany had coaxed out nearly every detail of Nick's life--his dead-end life, his lonely weekends, the way he melted at the slightest kindness. He'd tried to dodge the worst of it, but under her soft, probing questions, he'd folded like paper. *Pathetic*. At least he'd stopped short of admitting the late-night habits that stained his sheets and his phone, denied having any kind of problems knowing that he was a chronic masturbation addict. That, he swore, he'd take to the grave.

Then she asked to see his room. He panicked--dirty laundry, his fleshlight, half-eaten takeout, the faint glow of his monitor still on some incognito tabs full of momcest captions--so he'd stammered a refusal. Stefany let it drop, but not without a purr of amusement.

Stefany: "You're just too adorable," She sighed, voice dripping with honeyed pity. "The world doesn't deserve a sweet boy like you. It's cruel, leaving you all alone..." Nick's throat tightened. No one had ever talked about him like that, like he was a human... His fingers twitched toward the video call button.

"S-So..." He swallowed. "Can I see you now? We've been talking forever--you know I'm not some creep, right? Just... turn it on? Please?" He looked for the profile picture again, checking every tab on the screen. It was still empty. "I'll be good, I prom--"

Stefany: "Mmm, but why rush?" Stefany cut in, smooth as silk. "I'm always the one being watched. Isn't it more fun... letting me enjoy you for once?"

Nick's breath hitched. The way she said it--low, deliberate--sent heat pooling low in his gut. His imagination surged: Stefany arching a brow, Stefany biting her lip, Stefany commanding him-- "Did you... have something in mind?" He rasped and just like that, she asked.

Stefany: "Why don't you show me that beautiful body of yours? Come on, baby... Let me see those strong arms, that nice chest of yours."

Nick's face flushed instantly. "You... really want me to?" His mind raced--his scrawny frame, pale skin, the complete lack of muscle, the stretch marks, and a pair of boyish titties he hated. No one had ever asked before that.

Her voice shifted, suddenly cool. "You don't have to if you don't want to." The warmth was gone. He'd disappointed her.

"No, wait! It's just... I'm not exactly, uh, impressive." His throat tightened. A woman like her, interested in him? "Just.... There's not much to look at..."

Stefany: "Honey, I don't care." Her tone softened, velvety and sexy again. "You're probably way too hard on yourself. And it's just us here... nothing to be scared of. C'm I won't be cruel to you."

Nick swallowed. "Mmm... okay. Just my shirt, or...?"

"Everything." She says...

Nick almost choked. "R-really? You want to see me naked?" His mind flashed with unflattering images--his flat, pimpled ass, his skinny, hairless legs, and his hard pink cock, pathetically straining to a mere four inches (and prone to shrinking to less than one when soft).

"Absolutely," She replied.

That single word undid him. Hands trembling, face burning, he peeled off his shirt and tossed it to the floor, his nipples already hard stiffening under her imagined gaze. He stood abruptly, shoving the chair back as he stepped away from the desk. The button of his pants gave way easily; his cock was already hard when he kicked them into the corner.

"Mmmm--hhh... Is this okay?" Only his blue boxers remained, tented obscenely, the fabric damp at the tip.

"I said all," Stefany insisted.

Nick exhaled sharply, hooked his thumbs into the waistband, and pushed them down.

3. Sissy Academy.

Two days later.

Nick was mid-match in Call of Duty: Zombies, thumbs flying over the control, when he tossed his phone onto the couch and refocused on the screen. Two days. Forty-eight hours since his call with Stefany, and not a single reply. His earlier texts sat unread, marked by those mocking gray ticks. The zombies cornered his character, teeth gnashing as his health bar drained to zero. "Fuck!" He grabbed his phone again--still nothing. She'd vanished.

The memory of their call twisted in his gut. That night, Stefany's voice had coiled around him, teasing, commanding, until he'd ended up on his knees, legs splayed, one hand frantically working his hard cock while the other yanked his nose back. He'd groaned, tongue lolling, eyes rolling like some pathetic, ugly pig. At the time, it'd felt hot--the humiliation was the thrill. But now? Now he just felt sick.

He'd spent the morning scouring porn sites, convinced Stefany had recorded him as a joke. Every search-- "amateur humiliation cam," "Tinder catfish exposed"--came up empty. Maybe that was worse.

The Tinder notification chimed. Nick lunged for his phone, heart hammering. *Stefany, finally!* The message was just a link to that same strange site from before. Hands shaking, he copied it to his laptop and logged in.

The screen loaded.

And then--he saw it.

A scream clawed its way up his throat.

On the screen, where the black box with the "Start Stream" button should have been, there was only a lurid thumbnail--a frozen frame of himself, sprawled on the floor in that humiliating piggy position, eyes rolled back, a glistening thread of saliva dangling from his slack mouth.

His fingers trembled as he scrambled to message Stefany. "What the fuck is this?!" But before he could hit send, another notification popped up on his phone.

Stefany: "Watch it. You have 2 minutes."

No hearts this time. Just cold, clipped words.

"Two minutes? For what?!" He stabbed at the keyboard, but the message refused to be sent. A red error icon flashed mockingly. He slammed the app closed, reopened it--only to find his chat history wiped clean. Stefany's profile had vanished. If not for the grotesque image still leering from his screen, he might've convinced himself she'd never existed.

His breath came in ragged gasps. Then--a new horror: a timer popped on the screen, its digits pulsing like a heartbeat. Beneath it, in sickly pink letters:

--"Watch it, or I send this to your parents."--

"That fucking bitch!" He hurled a pillow across the room, barely registering the crack of soda against the floor. Chest heaving, he lurched back to the desk and clicked the video.

The screen went black. Then, line by line in glowing text:

- Name, age, state, address, IP address, cell phone number, school, his Facebook, IG, Tiktok accounts, grandparents' parents' names, addresses and numbers for all of them. -

It was all with his personal information:

Nick's stomach twisted into knots. He mashed the keyboard, desperate to skip ahead--but the screen stays frozen, the cursor a dead pixel. Five agonizing minutes later, the video lurched to life. His laptop speakers blasted to full volume, flooding the room with the sound of his own voice:

"My mom fucking hate me, Stefany. I just sit in my room all day and..."

On screen, a squalid video of himself: naked, one hand jerking his cock, the other pawing at his soft, boyish tits. His recorded self-complaints mixed with the hum of his fist wet in lubricant. Nick clawed at the lid, trying to slam it shut--but the video kept streaming, relentless.

"Shit! Shit! Shit!" He scrubbed at his eyes, tears smearing across his knuckles.

The scene cut. Now he was on his back, legs hooked over his head, fingers spreading his asscheeks wide. The audio droned on--his voice confessing every shameful secret: failed jobs, stolen money, the time he'd cried during his last ghosting.

Gagging, he grabbed his phone and stabbed at the browser. The link Stefany had sent was still there. He searched frantically, but Google only spat back sketchy "interview" sites--none matching the shit on his laptop. The URL was gibberish: a string of numbers, letters, and that sinister tail--.fzc6.

His hands shook as he dug deeper. Forum threads about malware and catfish. Honeypot scams. "Dark web slaves." A sob rose in his throat.

An hour and a half later, Nick lay curled on his bed, cheeks flushed raw, eyelids swollen like overripe fruit. The speakers still hissed with the echoes of his most shameful secrets--whimpers, pleading, the wet sounds of his fist played back in a loop. He'd scoured the web for solutions, but every forum, every thread from, had only scared himself more."

In the end, he'd collapsed onto the mattress, face buried in the pillow, choking on silent sobs. No police. One call, and that video goes straight to his parents' inbox. It didn't matter that he had no friends left to witness it. The thought of his mother's voice-- "Nicholas! What tha fuck is this shit!?"--was enough to make his stomach lurch.

He was fucked.

Then--silence.

The audio cut off mid-moan. The screen blinked out. By the time Nick staggered to his desk, his laptop had rebooted itself, leaving only a void of black and a single neon-pink emblem glowing at its middle:

SISSY ACADEMY

His breath hitched. The desktop was sterile--no icons, no documents, just five pristine folders lined up in a row, each labeled in crisp, academic font:

Classroom.

Course 1.

Course 2.

Course 3.

Files.

Needing answers, he clicked the icon with the school desk--innocuous. The screen flickered to life, instantly activating his camera. His own face stared back: wide-eyed, sweat beading at his temples. The reflection of a terrified boy, not a man. This was real.

"Hello?! Stefany?!" His voice cracked. "Why are you doing this?! I trusted you--you fucking recorded me! ANSWER ME!"

Silence. The camera's red light blinked, unblinking, like a predator's eye, but nothing more.

He waited. One minute. Two. Nothing.

With a snarl, he force-quit the app and kept searching.

Course 1. Course 2. Course 3. All password-locked. Each field demanded at least 30 digits--impossible to force. His fingers hovered over the keyboard before he gave up, dragging the cursor to the last option: a pink notebook icon labeled Files.