Day 5: Kailani (The Cam Session Starts)

The countdown on the monitor drops to zero. Kailani walks into frame with the grace of a predator who knows the prey's cage door is locked—and she’s on the inside. She gives the camera a long, lingering look before finally speaking.

“Evening, sinners.”

Her voice is smooth, confident, stage-warmed. It echoes slightly in the acoustically treated room—just enough to feel immersive without being hollow.

“I know, I know. You’ve all been very patient. And trust me… it’s going to pay off.”

She turns her head, motioning toward you. The stocks stand open and waiting. You’re behind them, heartbeat crashing in your ears.

“I’ve got a guest tonight,” she purrs. “A fresh little boy who walked right into the monster’s den… carrying a sword waaaay too small to slay me.”

She strides toward you and strokes her index finger up your semi-turgid cock. It raises under her touch like a pet begging under its owner's command. She laughs; a sharp, delicious sound. Not mocking. More like delight mixed with cruelty.

“Actually, this filthy little pervert is part of a game. That’s right. One where players score points for sex acts with strangers. And this week, he pulled me from the deck…” she turns slightly toward the camera, her voice dropping into a darker, more dangerous register, "...and a BDSM challenge.”

She lets the words settle into the chat. The scrolling commentary spikes in speed—bids starting, emojis flying, usernames pinging alerts.

“So tonight,” she says, stepping fully into frame, “he’s mine to play with. And yours to bid on.”

She moves to the side of the stocks, running one hand over the polished wood.

“But first…” she turns back to you, her tone serious, professional.

“Consent. You all know my views on that. With consent, it's all fun until someone screams the safeword. Without consent, your 15 minutes of play just turned into 15 years hard time."

She walks over and kneels slightly to look you in the eyes, mask to mask.

“You’re here of your own will?” You nod.

“You understand what’s happening?” You nod.

“You can ask me to stop at any time and I will?” You nod.

You even manage to vocalize a quiet “Yes.”

“Louder, pet. They need to hear it.”

“Yes.”

She nods once, crisp and clean.

“Good boy.”

She rises and turns back to the camera.

“We’re starting simple tonight. Classic restraint. Classic exposure.”

“We’re going to warm him up… in the stocks.”

She paces to one side and gestures you into place. You lean forward, fitting your arms and neck into the waiting grooves of the lower board. She lowers the upper half with a decisive click, locking you in place. You gulp. You're trapped. You can still speak but you haven't even discussed a safeword.

You’ve barely adjusted to the wooden embrace of the stocks when the flatscreen monitor emits a distinct, sultry moan—not loud, but unmistakable. It’s the sound of someone spending big.

Kailani tilts her head toward the monitor, one hand on her hip.

“Ooh,” she coos, “we’ve got a heavy hitter tonight.”

She saunters over and checks the screen, letting her fingers trail over the keys like she’s flirting with the hardware.

“Looks like someone just dropped some Benjamins for a request.”

She pauses, reading the username aloud.

“From a viewer calling himself… RhetturnToMe.”

She turns her head toward you, brow raised.

“Wait. Your game’s being run by a guy named Rhett, right?”

You groan. “You’ve got to be kidding me.”

She laughs and scrolls the message into view, reading it aloud in a mock announcer voice:

“‘I see you got our boy in the stocks there. $500 if you do the whole scene with him wearing a butt plug.’”

You shout at the camera, eyes wide. Surely that can't be part of the game. There must be a rule against making things worse for the players. Mustn't there? You already realize the answer is probably a huge "no".

“Rhett, you bastard! You set me up! And what the hell was with that low kink score?!”

Kailani raises her eyebrows, nodding in agreement. “Right? I’m only a 73 on kink? That’s barely above ‘accidentally owns handcuffs.’”

She grins back at the cam. “First you score me a 9 instead of a 10, then you mark me down on kink?” She gives a dramatic sigh, then glances at you and taps her temple. “Looks like I’ve got something to prove.”

She turns fully to the camera now, confidence gleaming. “You’re watching a 110%-rated session tonight, folks. I’ll earn every digit.”

She grabs a jar of vaseline from the side table and a slim, chrome-colored toy from the drawer beneath it.

“Speaking of which…”

She dips a finger into the vaseline, then slowly begins coating the toy, making sure the camera sees every glistening angle. The chat explodes with reaction bubbles and raised-bid messages.

“But before I get ahead of myself—safeword time.”

She strolls back to you, wagging the slick-coated plug in front of your eyes like a threat wrapped in chrome.

“Almost forgot. You’re new. Soft. Delicate. You might need this more than most.”

She leans in close to your ear.

“Pick a safeword. Something short. One word. If I hear it, I stop. No shame.”

You scramble for something coherent—your mind is racing.

Eventually, you croak out a single word.

“Pineapple.”

She smiles sweetly. Way too sweetly. “Perfect. Pineapple it is.”

Then—without hesitation—she pulls a ball gag from the nearby table and holds it up to the camera. “But of course… we won’t be needing it.”

Your eyes go wide as she fastens the gag into place, buckling it behind your head. You grunt in alarm, muffled and helpless. You can't even use the safeword. This is all kinds of wrong!

She leans in again and pats you gently on the head. “Relax, baby. I just couldn’t resist teasing such a timid little morsel.”

“If you really need me to stop?” She taps your foot with the toe of her boot. “Just stamp three times. That’s our deal.”

She rises again, turning back to the camera, and lifts the plug like a trophy.

“Now… let’s earn that five hundred.”

She steps behind you again, raising the butt plug once more for the cameras to catch its length and girth. Then she lowers it and gently pushes it between your buttocks. The tip of it touches your asshole and you jump so hard you feel like you're about to knock the stocks over. It holds though and she gentle presses onwards.

"If you weren't wearing that gag, pet," she purrs. "I'd say 'Open wide and scream AAAARGH!'"

The pressure builds, pain soon follows as a hole that was only ever used to expel things before is now **** wide to let something in. You shake your head, trying to maintain your rapidly fading composure as the plug is **** within you. You consider using your safety sign, stamping your foot hard, but you need those points. And... And... You have to face it, you're fucking turned on.

Suddenly she slaps the end of the butt plug, slamming it deep into your bowels. Your asshole closes over the thin neck of the plug, trapping it within you and you shudder as the sensations threaten to overwhelm you.

Kailani steps to your side and runs her index finger over the tip of your dick. It comes away sticky with precum which she shows to the camera before running the finger across your lips.

"He pretends to be such an innocent little mouse," she says. "But I think the secrets out about our nasty little pain slut. Don't worry, if you liked that I got a whole lot more planned for you."

The chat hasn’t slowed—if anything, it’s accelerating. But no new high-bid requests have pinged through yet. Kailani glances at the monitor, then back at you with a crooked smile.

“Let’s keep you nice and warm while we wait for round two, shall we?”

She turns to the table, sifting through a few tools with theatrical deliberation before selecting a small, glittering chain. You recognize what’s on either end almost immediately—crocodile clamps. Your stomach flips.

“Now, I could just wait for another request,” she murmurs, turning them so the light catches the metal, “but this one’s on the house.”

She steps in close and shows them to the camera, then lowers one… and then the other… toward your chest. The sharp teeth bite your flesh. You grit your teeth behind the gag, moaning through it as the pain spikes, radiates, and settles into a dull throb. Kailani steps back to admire her work, then flicks one clamp with her fingertip—hard enough to make your whole chest tense in response.

“That’ll keep the blood flowing.”

She steps behind you again. Her hand rests lightly on your lower back for a second—just enough to center you.

“Let’s get those cheeks glowing.”

The first spank is gentle. Barely more than a pat. Then another, just a touch harder. Your cock twitches at each slap, the pressure in your balls slowly building. She works in slow rhythm, gradually adding weight to each blow, watching your body respond. At first, the pain is tolerable. Manageable. Intensely stimulating.

But she’s not aiming for tolerable.

The next strike is sharper. Then harder. A sudden crack rings out, followed by another. Your breathing quickens. The clamps pull with every shift of your muscles, making the pain bloom across your chest and butt like fire.

Then she ramps up. It becomes too much. You gasp through your nose, your foot lifting instinctively. You’re ready to signal the end.

And then—

Mmmmmmhhhhh…

The moan from the monitor stops you cold.

Kailani freezes mid-swing, then slowly turns toward the screen. Her grin returns.

“Looks like we’ve got another tipper.”

She saunters to the monitor to check the request.