Stilettos & Submission

Trans office girl in heels gets exposed and roughly claimed—pain, pleasure, and total surrender.

Tags: trans, blackmail, nonconsensual, office, age-gap, domination, humiliation, rough-sex, anal, first-person

The office was quiet after hours, the fluorescent lights humming faintly overhead like a distant swarm of insects that refused to settle. I had stayed late again, my first week on the job already demanding more than I’d expected, but I didn’t mind the extra time if it meant proving myself. My glossy black patent leather high heels clicked sharply against the tile as I moved between desks, the tight black pencil skirt hugging every lush curve of my hips and the thick, rounded swell of my backside with unforgiving precision. The silky white blouse clung to my slender torso, the subtle lace trim at the collar brushing softly against the delicate hollow of my throat where my thin gold necklace rested. Sheer black stockings whispered along my shapely thighs with every step, and my slim bangle bracelets gave off a soft, nervous jingle whenever I reached for another file. My long, straight dark hair fell in a heavy curtain down to my waist, swaying like silk with each movement, while the delicate silver hoop earrings brushed the sides of my neck. At five-foot-six and just over sixty-five kilograms, my body had softened in all the places that made me feel most like myself—full, womanly hips, a generous bottom that shifted heavily when I walked, and small, rounded breasts that pressed gently against the fabric of my bra.

Mr. Harrington’s deep voice cut through the silence from behind his closed office door. “Nadia. In here. Now.”

My stomach twisted. I smoothed my skirt down over my thighs one last time, took a shaky breath, and pushed the door open. He was already seated behind his massive oak desk, but he stood as I entered, towering over me at well over six feet. Late fifties, broad-shouldered and solid, with a weathered face marked by deep crow’s feet around those piercing gray eyes. Salt-and-pepper stubble shadowed his strong jaw, and his thick silver hair was slicked back with precision. His crisp white dress shirt had the sleeves rolled up, exposing muscular forearms dusted with dark hair, the loosened navy tie hanging crooked, tailored gray slacks hugging his powerful thighs. The heavy gold watch on his wrist caught the light as he gestured for me to close the door.

The click of the latch sounded final.

He didn’t waste time. “I saw your file, Nadia. The real one. I know exactly what you are.” His voice was low, flat, laced with the kind of authority that made the air feel thicker. “You’re trans. Been on hormones for years. Prancing around my office in that tight little skirt like you think you can fool everyone.” His gray eyes dragged over me slowly, cold and assessing. “Do as I say tonight, or everyone in this building—and every client we have—finds out tomorrow. Your choice.”

The words landed like ice water down my spine. I froze, my large brown eyes widening, my full lips parting in shock. “Mr. Harrington… please. I just started. I need this job. I moved out on my own two months ago, I’m finally living as myself—don’t do this. I’ll do anything, just… don’t tell anyone.” My voice cracked, the bangles on my wrists trembling as my hands clenched at my sides. Tears already pricked at the corners of my eyes, but I forced them back, my heart hammering so hard I could feel it in my throat.

He stepped around the desk, closing the distance in two strides. Before I could back away, his large, rough hand shot out and seized my upper arm, yanking me forward until my hips bumped hard against the edge of his desk. “Anything?” he repeated, his breath warm against my face, carrying the faint scent of coffee and something darker, more masculine. “Good. Then shut your mouth and do exactly what I tell you.”

His other hand came up, fingers digging into the front of my blouse. One by one, the buttons popped open under his impatient tug, the silky fabric parting to reveal the smooth, tan-white skin of my chest and the lacy edge of my bra. He didn’t bother being gentle; he shoved the blouse off my shoulders and down my arms, letting it fall in a crumpled heap on the floor. My small, rounded breasts spilled free as he reached behind me and unclasped the bra with a single practiced flick, the straps sliding down my arms. Cool air hit my sensitive nipples, making them tighten into stiff peaks despite the fear churning in my stomach. His rough palms immediately covered them, squeezing and kneading the soft flesh with bruising pressure, thumbs rolling over the hardened tips until I gasped sharply.

“Fuck, look at these,” he muttered, voice thick with dark satisfaction. “Perfect little tits on a body like yours. So soft and girly.” His hands slid lower, gripping the waistband of my pencil skirt and yanking it down over my hips in one rough motion, taking my panties with it. The fabric pooled around my ankles, leaving me exposed in nothing but the sheer black stockings, my glossy stiletto heels, and the delicate jewelry that still adorned me. My thick, chunky ass was fully on display now, the heavy cheeks jiggling slightly from the abrupt movement, and between my smooth thighs my diminutive three-and-a-half-inch circumcised cock rested soft against my tight sac, nestled in the thick, dark pubic bush I’d always secretly loved on myself.

Mr. Harrington’s eyes dropped, and a low, mocking laugh rumbled from his chest. “Well, well. What the hell is this pathetic little thing?” His big hand wrapped around my small shaft, stroking it roughly once, twice, his calloused fingers tugging at the dense pubic hair around the base. “Tiny dick on such a pretty girl. Barely enough to fill my palm. And this bush? You really think that makes you more of a woman?” He squeezed my tight sac, making me whimper as a sharp jolt of discomfort shot through me. “Pathetic. You look so fucking feminine everywhere else—those thick thighs, that fat ass, those soft lips—but down here you’re just a sad little secret, aren’t you?”

I squirmed, trying to twist away, my voice breaking. “Please… stop touching me there. It’s humiliating. I didn’t ask for this—Mr. Harrington, I’m begging you, don’t…” But my words dissolved into a choked cry as he spun me around and shoved me down to my knees on the carpet. The thick pile dug into my stockinged knees, my stiletto heels scraping for balance, the four-inch heels forcing my back to arch and my heavy bottom to jut out behind me. My bangles clinked loudly as I instinctively raised my hands to push against his thighs.

He towered over me, already unbuckling his belt and freeing his thick, veined cock. It was heavy and flushed, far larger than my own, the shaft ridged with prominent veins and the head glistening. He gripped my long dark hair in one fist, yanking my head back so my large brown eyes met his cold gray ones. “Open that pretty mouth, girl. Time to put those pouty lips to work.”

I shook my head frantically, tears spilling over now. “No—no, please, I can’t. It’s too big, I’ll choke—” But his free hand seized my jaw, forcing my plump lips apart. The hot, salty head of his cock pushed past them instantly, stretching my soft mouth wide around its girth. The taste flooded my tongue—musky, slightly bitter—as he thrust forward without mercy, sliding deeper until the thick shaft filled my mouth completely and bumped against the back of my throat.

I gagged hard, my eyes watering instantly, throat convulsing around the intrusion. Saliva pooled and spilled from the corners of my stretched lips, dripping in thick strands down my chin and onto my bare breasts, then lower, soaking into the tops of my sheer stockings. He didn’t pause. His hips rocked forward in a steady, brutal rhythm, fucking my mouth with deep, punishing strokes that made my head bob helplessly. My bangles jingled with every jolt, the delicate silver hoops in my ears swinging wildly. I tried to pull back, my hands slapping weakly at his muscular thighs, but his grip in my hair only tightened, holding me in place as he drove deeper.

“That’s it,” he growled, voice rough with pleasure. “Take it all, you little fraud. Suck like you mean it. Look at you—on your knees in those slutty heels and stockings, drooling all over my cock like a desperate whore. Even with that worthless little prick between your legs, you still look so fucking girly.” He thrust harder, the head battering my throat until I retched, more saliva pouring out in messy rivulets that coated my chin and dripped onto the carpet between my knees. My full lips were swollen and glossy around his thickness, stretched obscenely, my tongue pressed flat against the underside of his shaft as he used my mouth without restraint.

Pain bloomed in my scalp from his iron grip, my jaw aching from the constant stretch, my throat burning with every deep plunge that cut off my air. I whimpered and moaned around him, the sounds wet and broken, my large doe eyes blinking up at him through a haze of tears. My small cock twitched traitorously against my thigh despite everything, a tiny bead of wetness forming at the tip, but the humiliation only burned hotter. He kept going, hips snapping forward, the heavy weight of his balls slapping against my chin with each thrust, his muscular forearms flexing as he held me exactly where he wanted me.

Minutes stretched into what felt like an eternity of relentless face-fucking. My stockings were soaked with drool now, my breasts glistening, my long dark hair tangled in his fist. My body trembled in the restrictive heels, the arch of my back making my chunky ass sway slightly behind me. He groaned low in his throat, his face flushing darker, sweat beading at his silver hairline, but he didn’t finish. Instead, with a final deep push that made me gag violently one last time, he pulled his thick cock free from my mouth with a wet pop.

I gasped for air, coughing and sputtering, strings of saliva still connecting my swollen lips to the glistening head of his shaft. My chin and chest were a mess, my makeup smudged, eyes red and watery. Mr. Harrington stood there breathing hard, his cock throbbing heavily in front of my face, flushed and slick with my spit.

His gray eyes burned with possessive hunger as he looked down at me. My knees still ached from the carpet, my swollen lips parted and glistening with the mess of saliva that coated my chin and dripped in slow, sticky trails across my small, rounded breasts. I tried to catch my breath, my chest heaving, the thin gold necklace cool against my flushed skin, but he gave me no time to recover. His large hand clamped around my upper arm again, fingers digging into the soft flesh hard enough to leave marks, and he hauled me upright before spinning me around to face the desk.

“Bend over,” he ordered, his voice a low rasp thick with need. “Ass up, just like the eager little slut you’re pretending to be.”

I shook my head, my long dark hair swinging heavily across my bare back, the bangles on my wrists clinking frantically as I pressed my palms against the edge of the desk. “Mr. Harrington, please… I can’t do this. It’s too much—my mouth already hurts so badly, and I’m not ready for anything else. Don’t make me—” My words cut off in a sharp cry as he shoved me forward, forcing my upper body down onto the cool oak surface. My small, perky breasts flattened against the wood, nipples scraping roughly as my cheek pressed to the desk. The four-inch stiletto heels kept my legs straight and slightly spread, arching my back dramatically and lifting my thick, chunky backside high into the air. The sheer black stockings stretched tight over my shapely thighs, the glossy patent leather gleaming under the fluorescent lights as my plush cheeks parted naturally, exposing the tight, smooth entrance between them.

He stepped in close behind me, his clothed thighs brushing the backs of my legs, the heat of his thick cock—still slick and throbbing from my mouth—pressing against the cleft of my ass. One of his rough hands landed heavily on the back of my neck, pinning me down firmly so my face stayed smashed to the desk, my large brown eyes wide and tear-filled as I stared sideways at the scattered papers. His other hand groped my left cheek first, squeezing the soft, yielding flesh with bruising strength, fingers sinking deep into the generous curve before he pulled it aside roughly. “Fuck, look at this fat ass,” he muttered, voice dripping with contemptuous lust. “So round and jiggly, like it was made for taking cock. And that tiny little prick hanging there between your legs—still twitching like it wants more even though it’s ridiculous.” He laughed darkly, his palm cracking down in a hard, open-handed slap that sent a jolt of stinging pain radiating through my cheek, making the heavy flesh ripple and bounce.

I yelped, my body jerking forward, the bangles jingling wildly. “Ow—stop hitting me! It hurts… please, I’m begging you, just let me go after this. I won’t tell anyone, I swear—” Another slap landed on the right cheek, harder this time, the sharp smack echoing in the quiet office. My plush backside burned, the skin blooming hot and red under his repeated strikes as he kept spanking me rhythmically, each impact making my thick cheeks jiggle and quiver. The pain bloomed sharp and hot, mixing with an unwanted flush of heat that spread through my core despite the tears streaming down my face. My small cock—barely three and a half inches even when it stiffened slightly—twitched against the front of the desk, the dense dark pubic bush around its base brushing the wood, a humiliating bead of wetness leaking from the tip and smearing there.

“Girly as hell everywhere except that worthless little thing,” he growled, kneading both cheeks now with both hands, spreading them wide so the cool air hit my tight hole. “You walk around here like a proper young woman in your tight skirt and heels, but this body’s just begging to be used.” I felt the blunt, swollen head of his cock nudge against my entrance, slick with my own spit, and I tensed, whimpering loudly. “No—no, wait, it’s going to hurt too much, I’ve never taken anything that big before without—” But he thrust forward in one brutal motion, burying half his thick length inside me with a wet, stretching push that tore a raw cry from my throat.

The burn was immediate and intense, my inner walls clenching hard around the invading girth, the veined shaft forcing me open wider than I’d ever felt. Pain flared deep in my belly as he sank deeper, inch by inch, until his hips met my reddened cheeks and his heavy balls pressed against my tight sac. I gasped and moaned, my fingers scrabbling uselessly against the desk, the delicate silver hoops in my ears swinging with every shudder. “It’s too deep… I feel so full it hurts—ahh!” He didn’t wait for me to adjust. His hand once more pinned down my neck, holding me immobile while the other resumed slapping my ass in time with his thrusts—hard, punishing strokes that made my chunky backside bounce and ripple each time his hips slammed forward.

The desk creaked loudly under the force of his pounding, the rhythmic impacts driving his thick cock in and out of me with wet, obscene sounds. Every deep plunge sent sparks of stinging pain and reluctant, twisting pleasure shooting through my core, my small cock leaking steadily now against the wood, the tight sac drawing up as my body betrayed me. My sheer stockings whispered against his pants as my legs trembled in the stilettos, heels scraping for purchase. “Please… slower,” I sobbed, voice breaking. “You’re being too rough—I’m going to bruise everywhere…” But he only laughed, low and cruel, leaning over me so his silver hair brushed my shoulder and his breath burned hot against my ear.

“Bruise? You’re lucky I’m not bending you over every desk in this office. Take it like the fraud you are.” His thrusts grew faster, harder, the angle letting him grind against that sensitive spot inside me until unwilling moans slipped from my swollen lips despite the tears. My voluptuous hips rocked back involuntarily with each slam, the bangles on my wrists rattling as my arms shook. He reached around once, groping my small breasts, pinching the stiff nipples until I whimpered sharply, then slid his hand lower to wrap around my diminutive cock, stroking it roughly in time with his pounding. “Look at this sad little thing leaking all over my desk. Tiny cock on such a soft, curvy body—makes me want to fuck you even harder just to remind you what you really are.”

The combination of his thick shaft stretching me open, the relentless slaps on my burning cheeks, and his calloused fingers tugging at my small length pushed me closer to an edge I didn’t want to approach. Pain and heat blurred together until my moans grew louder, more broken. He kept going for what felt like endless minutes, the office filled with the wet slap of skin, the creak of the desk, and my own desperate pleas mixed with unwilling gasps.

Finally, with a grunt, he pulled out abruptly, leaving me gaping and empty, a trickle of slickness running down my inner thigh onto the stocking. I barely had time to whimper in relief before he flipped me over onto my back on the wide desk, my legs splaying wide as he shoved them apart. My glossy black stilettos pointed toward the ceiling, the heels dangling in the air as my knees bent and fell open, exposing everything. My long dark hair fanned out beneath me like a dark halo, my tan-white skin flushed and marked with red handprints on my ass and thighs. He stepped between my spread legs, his muscular frame looming over me, shirt still half-buttoned and tie loose, gray eyes locked on mine with that same cold hunger.

“Legs up and open, girl,” he commanded, gripping my thighs and pushing them back until my knees nearly touched my shoulders, folding me in half on the hard surface. The position left me completely vulnerable, my thick backside lifted slightly off the desk, my small cock and tight sac on full display against my lower belly. He didn’t hesitate—his thick cock, glistening and veined, pressed back against my stretched entrance and sank in deep again in one smooth, powerful thrust. This angle was even more intense; I could feel every ridge dragging along my inner walls, the head bumping that spot inside me with every drive.

I cried out, my hands flying up to clutch at his forearms, the bangles clinking against his skin. “It’s so much deeper like this… I can feel you in my stomach—slow down, please!” My full lips trembled, large brown eyes pleading up at him as he loomed closer, his heavy body pressing down onto mine. His silver hair fell across his forehead, sweat glistening on his weathered face as he began thrusting steadily, the desk rocking beneath us. One of his large hands reached down between us, groping and kneading my small breasts again, rolling the sensitive nipples between his fingers until they ached. The other hand braced beside my head, caging me in as his hips snapped forward, driving his cock in and out with lewd, wet sounds.

“Such a pretty, soft little thing under me,” he taunted, voice rough. “All dolled up in stockings and heels, but that pathetic excuse for a cock is dripping all over your own belly. Leaking like a desperate girl even while I wreck your ass.” My diminutive shaft twitched and leaked steadily against my smooth stomach, the dark pubic bush matted with it, and the humiliation burned hotter as he watched it with a mocking smirk. I turned my face away, sobbing softly, but my body clenched around him involuntarily, the pleasure building despite the rough way he used me. My shapely thighs quivered in the sheer stockings, heels swaying in the air with each powerful thrust. He kept the pace relentless, his heavy balls slapping against my reddened cheeks, one hand occasionally drifting down to slap the side of my thigh or pinch my nipple harder, drawing fresh cries from me.

After long, grinding minutes of being folded and filled, he pulled out again, breathing hard, his face flushed darker. “Up,” he growled, sitting back in his leather office chair and yanking me toward him by the hips. I stumbled on shaky legs, the stilettos clicking unsteadily as he pulled me onto his lap facing him. My knees planted on either side of his thighs, straddling the chair, my thick backside hovering over his throbbing cock. The position forced my voluptuous hips to tilt forward, my small cock brushing against his lower stomach as he gripped my waist with both large hands.

“No more… I’m too sore already,” I whimpered, trying to push against his chest, my bangles rattling. “My legs are shaking—I can’t ride you like this, please…” But he lifted me slightly and pulled me down hard, impaling me fully onto his thick length in one motion. The sudden fullness made me gasp sharply, my inner walls fluttering around him as I sank all the way down until my plush cheeks rested against his thighs. His hands stayed on my wide hips, fingers digging in possessively as he guided me up and down, forcing me to bounce on his cock.

The bangles jingled with every forced rise and fall, my long hair swaying across my back and brushing my shoulders. My small, rounded breasts bounced in time with the rhythm he set, nipples stiff and sensitive. “That’s it—move those curvy hips for me,” he ordered, smirking up at my flushed, tear-streaked face. “Look how your tiny prick bounces around while you take every inch. So fucking girly and useless at the same time.” I moaned unwillingly, the angle letting his shaft grind perfectly inside me, sending waves of reluctant heat through my core. My hands clutched his shoulders for balance, the sheer stockings stretched taut over my spread thighs as I rocked and bounced under his guiding grip. He leaned in, mouth latching onto one of my nipples, sucking and biting lightly while his hands kneaded my heavy backside, spreading the cheeks wider with each upward pull.

I couldn’t stop the broken sounds escaping me—soft cries and gasps that mixed shame with the building pressure. My small cock leaked steadily against his stomach, the dark bush tickling his skin, but he only chuckled darkly around my breast. “Pathetic little thing is so hard for someone who keeps begging me to stop.”

He kept me riding him like that for what felt like forever, the leather chair creaking under us, until his breathing grew ragged. Then, with a final deep groan, he lifted me off and stood, spinning me around to face the large window overlooking the dark city skyline. The cool glass pressed against my palms as he pushed me forward slightly, my breasts flattening against it, my stiletto heels scraping the floor. He lifted one of my legs slightly, hooking it higher so my knee bent and the glossy heel pointed outward, opening me further. His thick cock nudged back between my cheeks from behind and thrust upward into me in a standing position, the new angle making me feel every inch even more intensely.

My forehead rested against the window, breath fogging the glass as he drove into me with powerful upward strokes, his hot breath on the back of my neck. One arm wrapped around my waist, holding me steady, while his other hand reached around to wrap around my small, leaking cock, stroking it teasingly in time with his thrusts. “Look at yourself out there,” he murmured against my ear, voice thick. “All dressed up like a proper office girl, yet bent over and taking it like this. That soft, jiggly ass and those stockings—perfect for fucking.”

The city lights blurred through my tears as the sensations overwhelmed me—the deep, upward plunges stretching me wide, the rough strokes on my diminutive length, the way my body trembled and clenched around him. My chunky backside pressed back against his hips with every thrust, the pain long since melted into a relentless, unwanted pleasure that built higher and higher. I moaned loudly now, unable to hold back, my voice echoing softly in the empty office. “It’s too much… I’m going to… please, just finish…”

He thrust harder, faster, his hand tightening around my small cock until the pressure finally snapped. My body shuddered violently, a reluctant release spilling weakly over his fingers and onto the floor as I cried out. Moments later, he buried himself to the hilt with a deep, guttural groan, his thick cock pulsing inside me as he filled me completely, the hot rush flooding deep within. He held me there, pressed against the glass, his heavy body pinning mine as the last spasms shook him.

When he finally pulled out, a warm trickle escaped down my thigh, soaking into the top of my sheer stocking. I trembled uncontrollably in my glossy black stilettos and jewelry, legs weak, my curvy frame marked and spent, leaning against the window for support as he stepped back, breathing hard. The office fell silent again except for my soft, ragged sobs and the faint hum of the fluorescent lights overhead.