Lara Lynn

THE CORPORATE LADDER GOES BOTH WAYS 43: WELCOME BACK!

The makeup that adorned her face followed the same pattern: red and green eyeshadow with a few white touches. She wore cowgirl boots, a leather belt, and had jet-black hair that hung straight and glossy. Around her neck, a leather collar gleamed with "MARIA" spelled out in golden letters.

"Shit… what have they done to you?" The sight before her confirmed Skye’s fears. Her friend had b...

THE CORPORATE LADDER GOES BOTH WAYS 42: PADDED FUN

"Into your sweet sissy ass? I very much hope so," Vivian teased as she tugged the straps, ensuring they cut right into Skye’s butt crack.

"N-no, it’s not only that… it’s the… the p-plug…" Skye whimpered, shifting awkwardly as the overalls pressed against the lacy pantaloons, which in turn pressed the padded Hello Kitty panties and the diaper, which finally pushed on the butt p...

THE CORPORATE LADDER GOES BOTH WAYS 41: DÉJÀ VU GETAWAY

Gloria leaned over, kissing Emilio before turning to María. "Bien hecho. Maybe we keep the belt off a little longer… if you keep behaving. Now clean yourself up, puta. We've got more fun planned today."

"Sí, Señora Gloria," María replied, sated for the first time in months.

After playing some more, Gloria and María slipped into bimbo talk out on the balcony while Emilio reste...

THE CORPORATE LADDER GOES BOTH WAYS 40: MARIA

"I walk as fast… tan rápido como puedo, Señora Gloria," Maryann panted, her words tripping over themselves as she struggled with the English. "These bags are… cómo se dice… heavy! ¡Muy pesadas!"

Gloria stopped dead in her tracks, spinning around with a glare that could cut glass. "¡Oye! You lazy maid, how dare you talk back to me! Apologize at once!"

"Sí, Señora Gloria....

THE CORPORATE LADDER GOES BOTH WAYS 39: SERVING THE SEÑORA

Gloria’s faint but unmistakable moans filtered down, tangled with the rhythmic thumping of what was clearly more than a "stretching" session. That bimbo was getting a good morning fuck.

Raw envy gnawed at Maryann. "Fuck… I’m so jealous."

The moans grew louder. "Ay, sí, Troy, más duro!"

Maryann moved faster, scrubbing harder, trying to drown out the sounds. She finished...

THE CORPORATE LADDER GOES BOTH WAYS 38: A DAY UNLIKE ANY OTHER

"Y-Yes," Skye managed, scurrying out of the room as quickly and quietly as her heels would allow. "Shit. Shit. Shit. What was that?" He seemed beside himself after his words—and that touch. Skye knew he was possessive; who wouldn’t be of someone like Maryann? But what was his game with her? Maryann at a health resort? Unlocked from her chastity? None of it added up. Not with the life Maryan...

THE CORPORATE LADDER GOES BOTH WAYS 37: A DAY LIKE ANY OTHER

"Yeah. Freaking peachy."

"Hahaha! That was so funny. He could have humped you for hours if Natalie hadn’t rescued you."

"It was awful! I mean, what’s with dressing us like sissies and watching us have a slumber party? I don’t get it, Mistress."

"You would if you were on the other side."

"Hardly. It’s a silly kink."

"Too bad for you, babygirl, because I alr...

THE CORPORATE LADDER GOES BOTH WAYS 36: SÍ, SEÑORA GLORIA

"Bitch, this is silk!" Gloria screeched, leaping to her feet as she stared down at the spreading stain. "This costs more than you’ll make in six months, you clumsy idiot!"

"Gloria… I’m so sorry…"

"Oh, I’m gonna make you sorry, alright," Gloria hissed, her hand shooting out as if to grab Maryann by the hair.

Before she could make contact, a voice cut through the tensi...

THE CORPORATE LADDER GOES BOTH WAYS 35: BIMBO MAINTENANCE WORKOUT

Flopping onto the plush sofa, she grabbed the remote and flicked on the TV. It landed on one of her favorites—Plastic Palace, where fake-titted girls screamed at each other over nothing.

Perfect. Mindless drama to match her mindless mood.

She was halfway through an episode, barely paying attention as two girls argued over a spray tan gone wrong, when she heard footsteps and giggle...

THE CORPORATE LADDER GOES BOTH WAYS 34: VANITY TRAP

"Gloria, you are like, wow!"

"No, you—tú sí estás perrísima. Mamacita, you have such a hot body… qué nota. Me muero. Those tetas, mami! I mean, wowzers! I am so happy to have you here. Welcome home. Mi casa es su casa."

"Thanks! Your house is, um, like, a total dream!"

"Ay, it’s a palacio, right? Pure lujo! But let’s talk about you, reina. Emilio’s been bragging...

THE CORPORATE LADDER GOES BOTH WAYS 33: A DIFFERENT KIND OF LADDER

"What do we have here…" Skye whispered, scrolling through another locked folder. "Holy tuck! This is the one! I can’t believe it!"

The sound of a car outside snapped the sissy alert. The front door creaked open. She shut down the computer, locked the master bedroom, and ran into the hall.

"Skye! Skye! Mistress is back from the country club and wants to play! Where’s my sissy g...

THE CORPORATE LADDER GOES BOTH WAYS 32: XXL BLOWN UP

Tomorrow came, and there he was—sleeves rolled, car door open, every inch the man who made her knees weak. "Ready to go home, chica?"

The ride was, like, total heaven: tinted windows, a cute playlist, iced tea chilled in the cupholder. With her eyes closed, the dream-echoes flickered again—ugh, so weird, so messy. Her brain felt like glitter dumped on wet paint, all sticky and random....

THE CORPORATE LADDER GOES BOTH WAYS 31: SCHEDULED

She toed a half-open SteelTech box under the desk. Inside: lacey "office appropriate" lingerie, fishnets, and two neatly packed dildos. No doubt about it—SteelTech kept its sluts spoiled, supervised, and stocked.

Then the nightstand: vitamins, droppers, orange bottles with childproof caps. Skye frowned. In two weeks of growing close to Maryann, she’d never seen anyone take so many pil...

THE CORPORATE LADDER GOES BOTH WAYS 30: 1 LINER

"More fun, more friends. Don’t be such a buzzkill!"

"Yeah, sweetheart, don’t be shy. We know how to show a girl a good time. You’re asking for it, I can tell."

"I’m just… It’s loud in here, and I’m kinda dizzy…"

"I will take care of you, pretty," Maryann’s woman purred, tightening her grip.

"Come with us, ladies. Got a better spot than this sweaty floor...

SISSY IN THE MIRROR PART 1

Hey babes, just letting y’all know this one became public! Have the loveliest Sunday.


Enjoyyy! 💋Xoxo💋
Lara Lynn

THE CORPORATE LADDER GOES BOTH WAYS 29: HOT

"Okay. Just… go slow."

She heard the squirt of lube, then felt Skye’s fingers circling her entrance. Her asshole jolted at the first touch, tightening instinctively.

"Easy, easy. Breathe for me. Let me in. It’s just a little at first."

Maryann gasped, clutching the rug tight as the sensation claimed her—intrusive, but not quite painful. The brush of Skye’s acrylics r...

THE CORPORATE LADDER GOES BOTH WAYS 28: SKYE’S SHOULDER

"A movie? The two of us?"

"Uh, duh!"

"Oh… I… Yeah, I’d love that."

On the escalator up to the cinema, Skye teased Maryann. "So… what about Emilio?"

"What do you mean?"

"Girl, I have seen the way you look at him."

"N-no! He’s just my boss… I would never…"

"You have to admit he’s handsome."

"He is…"

"And he’s so… you know...

THE CORPORATE LADDER GOES BOTH WAYS 27: DAY-OFF PRESCRIPTION

"You’re safe, chica. Go let the afternoon be kind to you."

Maryann stepped forward on impulse and hugged him, quick and careful not to crease his tie. "Thank you," she whispered. "Like, for real."

He patted her shoulder. "For real," he echoed. "Now go."

Skye hooked her arm through Maryann’s and steered them toward the elevators with the brisk joy of a girl who has a missio...

THE CORPORATE LADDER GOES BOTH WAYS 26: BE MY BUNNY

"That’s not the point!"

"Then what’s it, honey?"

"I mean," Maryann pointed at her chastity belt, "he, like, totally cannot do this to me! Like, seriously!"

Elise shook her head indulgently as she opened an official-looking pink-and-gold binder. "Believe me, sweetie, he absolutely can. It’s clearly stated in your S.L.U.T. contract. Let’s see… Ah, here we are."

H...

THE CORPORATE LADDER GOES BOTH WAYS 25: MOUTHFUL OF DUTIES

She thought she’d lose her mind juggling this chaotic agenda, but then she discovered that girls enrolled in the S.L.U.T. program got their

She thought she’d lose her mind juggling this chaotic agenda, but then she discovered that girls enrolled in the S.L.U.T. program got their own virtual assistant, an AI named Shyrley.

Managing her life became a breeze with Shyrley thinking f...

THE CORPORATE LADDER GOES BOTH WAYS 24: SAYURI SHIROSAWA

Maryann slumped against the wall as she watched the men drift into satisfied sleep. "Fuck, I almost can’t feel my legs." Across the room, th

Maryann slumped against the wall as she watched the men drift into satisfied sleep. "Fuck, I almost can’t feel my legs."

Across the room, the lolita—her pigtails askew, her eyes wide with nervous hope—tiptoed shyly up to Sayuri-sama. 2025-08-21 09:00:08 +0000 UTC View Post

THE CORPORATE LADDER GOES BOTH WAYS 23: RED LATEX REDEMPTION

Subject: Welcome, Maryann, to SteelTech’s S.L.U.T. Program! Dear Employees, We proudly announce that Maryann has officially joined the S.L.U

Subject: Welcome, Maryann, to SteelTech’s S.L.U.T. Program!

Dear Employees,

We proudly announce that Maryann has officially joined the S.L.U.T. Program and is fully prepared and eager to serve your needs. Please give Maryann a warm we...

THE CORPORATE LADDER GOES BOTH WAYS 22: ORAL FIXATION

"It’s okay, chica. I know you didn’t mean to be such a pain. You just forgot your place for a minute there. But you’re gonna fix it now, rig

"It’s okay, chica. I know you didn’t mean to be such a pain. You just forgot your place for a minute there. But you’re gonna fix it now, right?"

"Yes…" Maryann's hands reached up to massage his crotch through his slacks, determine...

THE CORPORATE LADDER GOES BOTH WAYS 21: TWO IN A ROW

"And with these pills, your brother will stop having those nasty, inappropriate erections." "Thank you so much, doctor. It’s been difficult

"And with these pills, your brother will stop having those nasty, inappropriate erections."

"Thank you so much, doctor. It’s been difficult dealing with his stubbornness, but your guidance has been invaluable."

"Oh, it's entirely my pl...

THE CORPORATE LADDER GOES BOTH WAYS 20: HOW I MET MY SISSY

"Hey, Skye, um, can I ask you something?" Maryann mumbled, staring at her chipped nail polish to avoid eye contact. "It’s kinda… personal."

"Hey, Skye, um, can I ask you something?" Maryann mumbled, staring at her chipped nail polish to avoid eye contact. "It’s kinda… personal."

"Hey, Skye, um, can I ask you something?" Maryann mumbled, staring at her chipped nail polish to...

THE CORPORATE LADDER GOES BOTH WAYS 19: FOR A FISTFUL OF DOLLARS

"Good girl. Now, do your spin." Maryann lifted the hem of her miniskirt to show the chastity belt locking her sex and did a slow twirl, disp

"Good girl. Now, do your spin."

Maryann lifted the hem of her miniskirt to show the chastity belt locking her sex and did a slow twirl, displaying herself.

"How does it feel, chica?" Emilio asked as he sipped his coffee.

"It’s unc...

THE CORPORATE LADDER GOES BOTH WAYS 18: BREAKFAST IN BED

After the shower, she wrapped herself in a robe and padded barefoot into her living room, collapsing onto the couch with a sigh. The rest of

After the shower, she wrapped herself in a robe and padded barefoot into her living room, collapsing onto the couch with a sigh. The rest of the day stretched out empty before her, and she wasn’t sure if that was a relief or a curse. Her phone buzz...

THE CORPORATE LADDER GOES BOTH WAYS 17: MARGARITA HEAT

Maryann blinked, caught off guard. She wasn’t a big fan of sports, but the thought of a date with Derek was exciting. "Um, yeah, sure! That

Maryann blinked, caught off guard. She wasn’t a big fan of sports, but the thought of a date with Derek was exciting. "Um, yeah, sure! That sounds, like, super fun!"

"Bet. I’ll hit you up with the details. See you then, sexy."

Derek...

THE CORPORATE LADDER GOES BOTH WAYS 16: PAIGE’S SOLUTION

Maryann’s heart skipped a beat. The lie came quickly, almost reflexively. "No, nothing like that. I’m fine." She forced a weak smile, hoping

Maryann’s heart skipped a beat. The lie came quickly, almost reflexively. "No, nothing like that. I’m fine." She forced a weak smile, hoping Paige wouldn’t press further. It was true that sometimes her reflection still felt like a stranger�...

THE CORPORATE LADDER GOES BOTH WAYS 15: HEAT RISING

"Please, I can do it myself, I swear, just undo the cuffs for a minute—" Bertha shook her head, leaning against the stall wall. "Nope. You’v

"Please, I can do it myself, I swear, just undo the cuffs for a minute—"

Bertha shook her head, leaning against the stall wall. "Nope. You’ve lost that privilege. I’ll handle it." She rummaged in Maryann’s designer purse and pulled ...