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 been transformed into a sexually fetishized stereotype.

The sissy kept her distance, watching a...

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 plug stretching her boypussy. The sensation forced her to open her legs wider just to stand without w...

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 rested, giggling like schoolgirls about how he performed like a bull as they sipped champagne straight fr...

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. I’m sorry, Señora Gloria," Maryann mumbled, her head bowing low. She didn’t dare look up, know...

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 foyer and moved to the hall, then the living room—dusting frames, polishing the banister unti...

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 Maryann was living. Skye would drag the truth into the light, come hell, high water, or worse.

The s...

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 already bought you a super-cute onesie, and I am dying to see you in it."

"Mistress! Please don�...

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 tension. "Wow, what’s with all the yelling, my bimbos? Catfight?"

Emilio strode into the living r...

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 giggles echoing from the hall. Peeking over the back of the couch, she spotted Gloria and Troy near the gr...

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 about his hot office puta forever, and now I see why. You’re all plastic and pretty, te ves como ...

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 girl?"

"I’m coming! I’m coming, Mistress!"


Enjoyyy! 💋Xoxo💋
Lara Lynn 2025-09-20 09:54:22 +0000 UTC View Post

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. Lucky thing Paige had doubled her "happy pills." Now everything was wrapped in this fluffy cotton c...

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 pills. She picked up one bottle. "What the…"

Maryann swanned out from the vanity, shining like ...

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."

"At the VIP lounge."

"VIP!?" Skye yelled. "Hell yeah, let’s go! I’m so down."

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 reminded her, stupidly, that her own nails were overdue for a fill. Skye coaxed her open with more lu...

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." Skye did a little hand gesture that meant composed, steady, alpha. "Don’t tell me you wouldn’...

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 mission and an unlimited credit line.

"What’s on your mind, Skye?"

"Emilio must love you a w...

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."

Her voice shifted into a businesslike tone, reading aloud a paragraph of dense, complicated legal jar...

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 for her. The AI displayed her packed calendar, reminded her of her next S.L.U.T. class, and even told...

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.

"あの…ミキちゃん、よくできた？"

Sayuri-sama met her eyes and hugged her. "...

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 welcome.

As you may already know, due to her special circumstances and previous accident, Maryan...

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, determined to have her share of him as she rubbed against the growing bulge. "Mmnh… please… I need to…"...

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 pleasure. Just remember the essentials: always dress him in the frilliest sissyboi clothing you can fi...

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 avoid eye contact. "It’s kinda… personal."

"Maryann! You know I’m an open book. What is...

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 uncomfortable, boss. I can’t forget it’s there."

"Good, it’s important you don’t. What ab...

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 buzzed on the coffee table, and she saw the group chat with her friends lighting up. Of course, they’d...

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 gave her a wink before walking off. As he disappeared around the corner, she pressed her hands to h...

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’s, but she knew that if she dared to admit it, Paige might push her into another session of lucid ...

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 out a fresh pad and tampon. "Lift your skirt! We don’t have all day."

Enjoy! 💋 2025-07-17 09:00:08 +0000 UTC View Post