Boss Discovers Sissy's Thong Temptation

I never thought my little secret would unravel like this, but God, do I crave the thrill of confessing it all now. I'm Jamie, the quiet 22-year-old intern at Harlan & Associates, the kind of guy—or girl, depending on the day—who blends into the office wallpaper. Five-foot-six, slim as a whisper, with soft features and a shy smile that hides the fire underneath. By day, I wear crisp button-downs and slacks like every other drone in the corporate hive. But underneath? That's where my true self lives: a skimpy pink thong, the kind that hugs my smooth-shaven cheeks and cradles my little clitlette like a naughty promise. It's my armor, my rebellion, making me feel deliciously feminine amid the suits and ties. I slipped one on that Monday morning, the lace riding up just right, a secret buzz against my skin as I hustled into the office.

The break room was my undoing. I'd just finished a killer gym session before work—keeps this sissy body toned and perky—and my gym bag was stuffed with sweaty clothes. Rushing for my third coffee of the day, I swung the bag too wildly. It hit the counter, zipper burst open, and out tumbled my prize: the hot pink thong I'd changed out of, still damp from my workout, landing right at the feet of Mr. Harlan himself.

Time froze. Mr. Harlan—tall, broad-shouldered, with salt-and-pepper hair, piercing blue eyes, and a jawline that could cut glass. Stern as hell, the kind of boss who makes grown men stammer, but fuck, he's handsome in that authoritative, daddy way. He was mid-sip from his mug when it happened, his gaze dropping to the thong like a predator spotting prey. The lacy thing lay there, innocent and incriminating, its thin strap screaming "sissy slut" in the fluorescent light. My face burned crimson. I dropped to my knees, fumbling to snatch it up, but his polished shoe pinned it gently to the floor.

"Jamie," he rumbled, voice low and gravelly, eyes lingering—hungrily—on the pink fabric, then flicking up to meet mine. Electric tension crackled between us; I could feel his stare peeling back my layers, seeing right through to the femme heart pounding in my chest. "Care to explain this... wardrobe malfunction?"

"I-I'm so sorry, Mr. Harlan," I stammered, blushing so hard my ears rang, hands trembling as I stayed on my knees like a supplicant. "It was an accident. Please, don't fire me. It's just... something personal." My voice was a whisper, but inside, a wicked spark ignited. His eyes didn't leave the thong; they devoured it, and I swear I saw his slacks twitch.

He lifted his foot, letting me grab it, but instead of handing it back, he crouched down, close enough that I smelled his cologne—musky, commanding. "Personal, huh? Get up. My office. Now." No anger, just that hungry edge. My clitlette stirred traitorously in my fresh thong as I obeyed, bag clutched like a lifeline, following him down the hall with every coworker oblivious to the storm brewing.

His private office was a fortress: floor-to-ceiling windows with blinds that snapped shut as he locked the door with a decisive click. The pretense hit immediately. "Sit," he said, but I hovered, heart hammering. He leaned against his massive oak desk, arms crossed over his broad chest, eyes raking me over. "That thong in the break room... you wear things like that? Under your suit?"

I nodded, biting my lip, the confession spilling out in a rush because his gaze made me bold. "Y-yes, sir. Every day. It makes me feel... pretty. Feminine. I'm... I'm a sissy, Mr. Harlan. Have been since I was 18. Please don't judge me."

His laugh was dark, approving, sending shivers down my spine. "Judge you? Jamie, I've been fantasizing about sissies like you for years. Soft, obedient little things begging to be used." He stepped closer, towering over me, his hand lifting my chin. "Show me. Lift your shirt. Model it for your boss."

Tension exploded like fireworks in my veins. Trembling with need, I unbuttoned my shirt, letting it fall open to reveal the matching pink thong—skimpy, sheer, my smooth legs leading up to the lace framing my tiny bulge. I turned, arching my back, wiggling my perky ass for him. "Like this, sir?" My voice was breathy, slutty already.

"Fuck, yes," he growled, closing the distance. His big hands groped my ass cheeks, squeezing the flesh spilling over the thong's edges, then sliding forward to cup my growing clitlette through the damp fabric. I gasped, hips bucking into his palm as he stroked me firmly, thumb circling the tip. "So hard for Daddy already. Such a eager sissy slut."

The touch ignited me. I spun, dropping to my knees before he could blink, nuzzling my face against the massive tent in his slacks. "Please, Mr. Harlan—Daddy—more. I need it. Use your sissy intern." My hands fumbled his zipper, freeing his thick, veiny cock—nine inches of girthy perfection, throbbing and leaking pre-cum. I worshipped it with my mouth, but he pulled me up, eyes blazing.

"Bend over the desk, Jamie. Now."

I complied like the good girl I was, palms flat on the polished wood, ass presented high. He yanked my slacks and thong down to my thighs in one rough tug, exposing my smooth, puckered sissy hole. "Look at this tight little pussy," he murmured, spitting on his fingers before pressing one in. I moaned like a whore, pushing back as he worked me open—first one finger, then two, scissoring deep, hitting my spot until I was dripping, clitlette leaking onto the desk. "That's it, slut. Moan for Daddy."

"Harder, Daddy! Finger your sissy's hole!" I begged, voice muffled against the wood, body quaking.

He chuckled, withdrawing to shed his clothes, his muscular body gleaming—hairy chest, powerful thighs. But he wasn't done commanding. "Over here." He sank into his leather executive chair, cock standing like a throne. "Ride me, reverse-cowgirl. Show me that ass bounce."

Straddling him backward, I gripped his knees for balance, lowering my slick hole onto his thickness. The stretch burned so good—inch by inch, I took him, until my cheeks slapped his lap, fully impaled. "Oh fuck, Daddy! So big!" I cried, starting to bounce, my thong tangled at my thighs, clitlette flopping free and hard, bouncing with every rise and fall. His hands gripped my hips, slamming me down harder, the wet slaps echoing off the walls.

"Ride it like the sissy whore you are," he grunted, one hand reaching around to pinch my clitlette, tugging it like a leash. I rode faster, ass clenching around him, the chair creaking under us. But he wasn't satisfied. "On your back. I want to see that pretty face when I breed you."

He flipped me effortlessly onto the desk, legs spread wide, stockings I'd hidden under my slacks now fully exposed—sheer black, gartered for extra slut points. He plunged back in missionary-style, deep and punishing, his weight pinning me as he pounded my hole with long, brutal strokes. "Take Daddy's cock, Jamie. Milk it with that sissy pussy."

"Yes! Pound me! Fill me up!" I wailed, nails digging into his back, my clitlette rubbing against his abs with every thrust. The pressure built—his groans, the slick sounds, the way he owned me. I came first, hands-free, spurting ropes of sissy cum across my stockings, soaking the sheer fabric in sticky white. "Cumming, Daddy!"

He roared, burying balls-deep and erupting—hot, thick jets flooding my ass, claiming me utterly. We shuddered together, his cock pulsing as he pumped every drop into me.

Spent and satisfied, we collapsed in a heap on the desk, his body still covering mine, softening inside me. He kissed my neck, possessive. "You're promoted, sissy. My personal assistant starting tomorrow. New dress code: thongs only under your office wear. No more hiding that pretty ass."

I melted into him, our lips meeting in a deep, sealing kiss—tongues tangling, promising daily 'performance reviews' of rough office poundings. "Yes, Daddy. All yours."

His hands roamed my cum-soaked stockings as he whispered more filthy vows against my mouth, our affair just beginning—

Then, a sharp knock shattered the haze. "Mr. Harlan? Your two o'clock is here early—it's the board!" His secretary's voice, muffled but urgent through the door.

He froze, cock slipping free with a wet pop, cum trickling down my thigh as reality crashed in.