As you turned to leave Jess’s office, her voice cut through the air, sharp and commanding. “Tom, not so fast,” she called, her tone dripping with arrogance. “I’m not quite done with you yet.”
You froze in the doorway, dreading what was coming next. Slowly, you turned around, and there she was, lounging in her chair with a smug smile. It was the kind of smile that said she knew she had you completely under her thumb.
“There’s just one more little thing I need you to do,” she said, leaning forward on her desk. “Well, maybe not so little.”
You shifted uncomfortably, your pulse quickening. “What else do you need?”
Jess sauntered to the other side of her desk, moving with a deliberate slowness, savoring the moment. “I had some clothes delivered today—some new office attire. I haven’t had the chance to try them on yet, but I think you could help me with that.”
You blinked, confused. “Help? How?”
Jess’s grin grew wider, more devious. “Simple, Tom. You’re going to try them on for me. I want to see if they look good enough to keep.”
Your heart dropped, realizing what she was asking. This was beyond humiliating, and she knew it. “Jess, I’m not—”
“Not what?” she cut you off, her eyes gleaming with amusement. “Not willing to help out a friend? I thought we were trying to be friends now, Tom. Isn’t that what you wanted? To be on my good side?”
You were trapped, and she knew it. You could feel the power dynamic shifting even further away from you. She was your subordinate in title only, but in this moment, she had all the control. There was no winning here.
“Fine,” you muttered, swallowing your pride. “What do you want me to do?”
Jess’s eyes lit up with victory as she grabbed a large shopping bag from behind her desk and dumped its contents onto the chair. “Good boy,” she purred mockingly. “Now, let’s see. We’ve got this cute little pencil skirt, this blouse, and… oh, some tights, too. Can’t forget those! And of course, these heels to complete the look.”
Your face burned as she handed you the items one by one. Each piece felt like a step deeper into your own humiliation.
“You’ve got a full-length mirror in the break room,” she said with a sweet, mocking smile. “Go get dressed, Tom. I want to see how everything fits. Make sure it’s perfect.”
Your mouth went dry, and you stood there for a moment, too stunned to move. Jess raised an eyebrow, her tone suddenly harsher. “What’s the matter? Scared? You’re not going to chicken out now, are you?”
“No,” you said quickly, shaking your head. “I’ll do it.”
“Good. And don’t take too long. I’m sure Amber and Olivia will want to see the results too.”
Your stomach dropped. The thought of showing yourself off to not just Jess, but Amber and Olivia as well, made you feel sick. But there was no getting out of this now.
You left the office with the clothes in hand, your heart pounding in your chest. As you walked through the corridor, you passed Amber and Olivia, who gave you curious looks. If they knew what you were about to do, they’d never let you live it down.
Once you reached the break room, you shut the door behind you and leaned against it for a moment, trying to gather yourself. This was insane. How had it come to this? You were supposed to be the manager, the one in charge. But now, you were about to humiliate yourself in a way you’d never imagined.
With a sigh, you began to undress, carefully putting on each piece Jess had handed you. The skirt clung to your thighs uncomfortably, and the tights were a nightmare to pull on without tearing. The blouse felt soft and far too feminine, the silky fabric making you feel like an idiot. Finally, you slipped into the heels, wobbling slightly as you tried to steady yourself.
You caught sight of your reflection in the mirror, and it was worse than you imagined. You looked ridiculous. The clothes didn’t fit quite right, but they fit well enough to make you feel utterly humiliated. You looked like a walking joke, and the thought of walking back through the office dressed like this made your stomach churn.
Still, you had no choice. Taking a deep breath, you gathered your clothes in your arms and headed back to Jess’s office, every click of the heels on the floor echoing in the silence, each step feeling like it brought you closer to the ultimate humiliation.
When you reentered Jess’s office, she looked up from her desk and immediately burst into laughter. “Oh my God,” she howled, clutching her stomach. “This is priceless!”
You stood there, cheeks burning, as Jess circled you, looking you up and down with that same bratty smirk. “You look absolutely ridiculous,” she said, her voice full of mockery. “But, you know what? This is perfect. It really suits you.”
Before you could respond, she grabbed her phone and sent a quick message. “Amber, Olivia—come to my office. Now.”
Panic rose in your chest. “Jess, please—”
“What?” she interrupted, feigning innocence. “You said you wanted to be friends. Friends help each other out, right? Besides, Amber and Olivia are going to love this. You should be thanking me for letting them in on the fun.”
Moments later, Amber and Olivia strolled into the room, and their eyes immediately widened when they saw you standing there in Jess’s clothes.
Amber was the first to react, bursting into uncontrollable laughter. “No way! Jess, what have you done to him?”
Olivia covered her mouth, barely able to contain her amusement. “Oh my God, Tom, you look so… cute!” she teased, her eyes gleaming with wicked delight.
You felt like your entire body was on fire, your face red with shame as the girls circled you like predators, their eyes taking in every humiliating detail. Amber stepped closer, giving the skirt a little tug. “Hmm, a bit tight, don’t you think, Jess? But those tights? Oh, they’re just perfect.”
Olivia snickered, her voice dripping with mockery. “I bet he loves this, deep down. Don’t you, Tom? This is what you’ve been waiting for, huh? To be our little dress-up doll?”
You tried to speak, to defend yourself, but the words caught in your throat. The three of them were laughing so hard you could barely think straight.
Amber leaned in closer, her voice a low whisper meant only for you. “You know what, Tom? I think you look better in these clothes than Jess ever could.”
Jess smirked, crossing her arms. “Maybe I should give you these clothes, Tom. They suit you more than they do me. Would you like that?”
“I… no,” you stammered, unable to form a coherent sentence.
“Oh, don’t be shy,” Olivia teased, stepping around to your other side. “You should own it, Tom. Embrace it. You’re already halfway there.”
The laughter was relentless, and you could feel the room spinning with embarrassment. Just when you thought it couldn’t get any worse, Jess clapped her hands together, her bratty grin growing wider.
“Alright, Tom, enough standing around. Why don’t you strut your stuff back to the break room and change? Maybe we’ll catch you on the way there.”
You hesitated, but Jess raised an eyebrow, her voice suddenly sharp. “Well? Are you going to keep us waiting, or are you going to walk those cute little heels back to the break room like a good boy?”
The smirk on her face told you everything. You weren’t getting out of this without further humiliation. With a resigned sigh, you turned and headed for the door, each step in those heels feeling heavier and more embarrassing than the last. Amber and Olivia watched you go, snickering under their breath.
As you made your way through the office, your heart pounding in your chest, you felt like every eye was on you—even though most of the office hadn’t seen your humiliating getup yet. The hallway felt impossibly long, and each click of the heels echoed louder in your ears.
But just as you thought you’d made it to the safety of the break room, you heard a familiar voice behind you.
“Tom? What the hell is going on?”
You froze, blood draining from your face. You turned around slowly, dreading what you knew you would see.
Standing in the corridor, arms crossed and an incredulous look on her face, was Courtney.
And she had seen everything.
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