The rooftop of my shitty apartment building is my sanctuary, a jagged perch above the city where I can smoke a joint and let the world fuck off for a while. Tonight, I’m sneaking up the fire escape, the metal creaking under my white sneakers—cute as hell but tough enough not to snap my neck on the climb. My tight pink crop top clings to me like a second skin, hugging my small, perky breasts so close you can see my nipples straining against the thin fabric. It’s cropped high, flashing my flat stomach with every move, daring anyone to stare. My denim mini skirt’s a fucking tease—short enough to barely cover my plump, rounded ass, shifting with each step to show off my long, toned legs. At 5’6” and 56 kg, I’m light on my feet, but my body’s got curves and edges that demand attention.
My dark, wavy hair spills just past my shoulders, catching the moonlight as it frames my heart-shaped face—high cheekbones, a straight nose, full lips slicked with soft pink gloss, and brown eyes with lashes so long they cast shadows on my fair skin. I’ve been living as a woman for two years now, every inch of me shaped into something I love—right down to the tiny cock and balls tucked snug in my lacy pink panties. Up here, though, it’s just me and the night, no one to judge or gawk. I settle against the ledge, light my joint, and take a deep drag, letting the smoke curl from my mouth and drift over the sparkling skyline below.
Then I hear it—a rustle behind me. I whip around, heart slamming in my chest, and there’s a fucking security guard standing there, flashlight beam cutting through the dark. He’s tall, 6’2” at least, with a muscular build that’s gone a little soft around the gut. Caucasian, late 30s or early 40s, with short, cropped hair graying at the temples and a stern face carved with a strong jawline. His uniform stretches tight over his broad chest, name tag reading “Johnson.” He looks like the kind of guy who gets off on power, and his eyes are already stripping me bare.
“What the fuck are you doing up here?” he barks, voice rough and low.
I freeze, joint still pinched between my fingers, smoke trailing from my lips. “I—I was just chilling,” I stammer, my voice shaky.
“Chilling, huh?” He steps closer, eyes narrowing as he spots the weed. “This is private property, and that shit’s illegal. You’re in deep trouble, sweetheart.”
My stomach drops. I can’t deal with cops—not with my history, not as a trans girl who’d get more than a slap on the wrist. “Please,” I say, my full lips trembling. “I didn’t mean anything by it. I just needed a break.”
He smirks, his gaze raking over me—my tits, my legs, the way my skirt barely covers my ass. “A break, dressed like that? You’re begging for attention, aren’t you?” He’s close now, close enough I can smell his cheap cologne and sweat. “Pretty little thing like you, I bet you’re used to getting your way.”
I blush, my fair skin heating up, and fuck if my tiny cock doesn’t twitch under my skirt. His words hit something raw in me—humiliation mixed with a sick thrill I can’t shake. “I’m not—I just—”
“Shut it,” he cuts me off, snatching the joint from my hand and tossing it over the edge. “Here’s how this goes. You keep your mouth shut and do what I say, or I report you. Got it?”
I nod, throat dry. I don’t have a choice. “Yes, sir.”
“Good girl.” He steps back, arms crossed, eyeing me like a predator. “Lift that skirt. Show me what you’re hiding.”
My eyes go wide. “What?”
“You fucking heard me. Lift it. Now.”
My hands shake as I grab the hem of my skirt and pull it up, exposing my lacy panties. My tiny cock and balls barely make a dent, tucked tight against my body.
He laughs, a dark, guttural sound. “Holy shit, look at that. That’s not even a cock—more like a fucking clit. Pathetic.”
My cheeks burn, but my body betrays me, a shiver running down my spine. I’ve always had this fucked-up submissive streak, and him talking to me like this—objectifying me—it’s getting me wet in a way I can’t ignore.
“Take off that top,” he says next, voice hard.
I hesitate, then peel the crop top over my head, letting it fall to the concrete. My small breasts bounce free, nipples hardening in the cool air, and his eyes lock onto them.
“Nice tits,” he mutters, stepping closer. His hands grab my breasts, squeezing hard, thumbs flicking my nipples. I gasp, pleasure spiking through me, my long legs trembling.
Then he spins me around and shoves me against the railing. “Bend over, slut.”
I grip the metal, ass out, and he flips my skirt up, yanking my panties down to my knees. My plump ass is bare now, and I feel the night air on my skin, my tiny cock dangling uselessly between my thighs.
His hand cracks down on my ass, the slap loud as fuck. I yelp, the sting sharp. “That’s for trespassing,” he growls, then spanks me again. “That’s for the weed.”
Each hit makes my ass throb, red welts rising on my fair skin, and I can’t stop the moan that slips out. My cock leaks pre-cum, dripping onto my legs, and he notices.
“You fucking love this, don’t you?” he whispers, breath hot against my ear.
“Yes, sir,” I admit, voice small.
He chuckles. “Knew it. Let’s see how much you can handle.”
I hear his zipper, then the rustle of his pants. I peek back and see his cock—thick, 8 inches long, with a slight curve and a fat, glistening tip. It’s a monster compared to my little nub, and my ass clenches in anticipation.
He pulls a lube packet from his pocket—fucking prepared, this guy—and slicks up his fingers, then rubs it rough over my hole. No warning, he lines up and shoves in.
“Fuck!” I cry out, the stretch brutal. He doesn’t ease up, thrusting deep until his balls slap my tiny ones. “So fucking tight,” he groans, hands digging into my hips.
He pounds me, relentless, my body jerking against the railing with every thrust. The city lights blur as pain turns to pleasure, my ass gripping him, my tiny cock bouncing helplessly.
“Look at you, taking it like a dirty little whore,” he taunts, grabbing my dark hair and yanking my head back. My full lips part, brown eyes watering, cheeks flushed. “Such a pretty fucking face.”
The humiliation fuels me, and I moan louder. “Yes, sir, fuck me.”
He lets go of my hair and keeps slamming into me, then pulls out abruptly. I whimper at the emptiness, but he’s not done. He spins me around, lifts me up, and pins me against the wall. My legs wrap around his waist, and he drives back in, hitting my prostate dead-on.
“Shit, yes,” I gasp, my tiny cock trapped between us, rubbing against his uniform. His eyes bore into mine, watching me unravel.
“You’re gonna cum from my cock, aren’t you?” he growls.
I nod, breathless, and then it hits—my orgasm rips through me, my tiny dick spurting weak ropes against his shirt. He fucks me through it, dragging it out until I’m shaking.
He drops me to my knees, skirt still up, panties tangled. “Suck it,” he orders.
I obey, taking his cock in my mouth. It’s salty, slick with lube and my ass, and I gag as it hits my throat. My full lips stretch around him, spit dripping down my chin as I work him, my long lashes fluttering.
He groans, then pulls out and strokes himself, cumming hard—thick, hot spurts splatter my face, my tits, my lips. I lick it off, tasting him, dazed.
But he’s not fucking done. He grabs his baton—10 inches of thick, black rubber, cold as hell and unyielding—and my heart slams against my ribcage. “No way,” I whisper, my voice barely audible, trembling with a mix of dread and fucked-up excitement.
“Yes fucking way,” he snarls, his voice rough and commanding. He doesn’t wait for me to brace myself. With one hard shove, he pushes me onto all fours, my knees scraping the gritty concrete, my plump ass sticking up like an offering. My skirt’s already hiked up, my lacy panties yanked halfway down my thighs, and I can feel the night air teasing my exposed hole—still slick, still throbbing from what he’s already done to me.
He grabs a tube of lube from his belt, squirting it onto the baton with a loud, wet squelch that echoes in the quiet. The sound alone makes my stomach twist. Then he’s behind me, pressing the tip of that thick bastard against my hole. It’s cold, hard, and way bigger than his cock, and I whimper as he starts to force it in, slow but relentless.
“Fuck, it’s too much,” I gasp, my body tensing, my fair skin prickling with sweat. My tiny cock twitches between my legs, leaking pre-cum onto the ground, betraying how much I’m into this despite the panic. The stretch is insane, a burning ring of fire as my hole fights to take it. But he’s not gentle, not patient—he keeps pushing, sliding it deeper, inch by agonizing inch.
“Shut up and take it, slut,” he growls, his free hand clamping down on my hip, fingers digging into my flesh hard enough to leave marks. “You’re gonna take every fucking inch I give you.”
I try to relax, try to breathe, but it’s impossible. The baton’s unyielding, splitting me open, and I let out a sharp cry as it sinks deeper, filling me in a way that’s both wrong and so fucking right. My long, dark hair falls around my face, sticking to my sweaty cheeks, and my small breasts jiggle with every shuddering breath.
“Taking it like a champ,” he mutters, his voice low and smug, like he’s proud of how much he’s wrecking me. He starts to fuck me with it, slow at first, dragging it out then shoving it back in. Each thrust makes my ass clench around the cold hardness, sending shockwaves through me—pain and pleasure tangling together until I can’t tell them apart. My moans spill out, loud and desperate, echoing off the rooftop.
“Fuck, yes,” I hear myself say, pushing back against it, chasing that twisted ache. My body’s trembling, my toned legs shaking, but I can’t stop—I don’t want to stop.
He picks up the pace, slamming the baton in and out, and the wet, sloppy sounds of it fucking me fill the air. “Look at you,” he sneers, “getting off on this like the dirty little whore you are.” His words hit me like a slap, and I moan louder, my tiny cock throbbing, dripping more pre-cum onto the concrete below.
But he’s not done pushing me. He yanks the baton out with a sudden, wet pop, and I whimper at the emptiness, my hole twitching, gaping from the abuse. Before I can catch my breath, he reaches for his torchlight—a big bastard with a fat, rounded handle, easily twice as thick as the baton. My brown eyes widen, my full lips parting in a shaky gasp.
“That’s too fucking big,” I protest, my voice cracking. “It won’t fit, please—”
He cuts me off with a dark, cruel laugh. “Oh, it’ll fit, princess. And you’re gonna love every second of it.”
He slicks up the handle with more lube, the squelching sound obscene and deafening. Then he’s pressing it against my wrecked hole, the blunt end pushing hard. I brace myself, but when he starts to force it in, the stretch is beyond anything I’ve felt. It’s like my body’s being torn apart, the pressure unbearable, and I sob, “Too much, fuck, it’s too much!”
“Cry all you want,” he grunts, ignoring me, his muscles flexing under his uniform as he works it deeper. “You’re taking it, slut.” Tears stream down my face, my high cheekbones slick with sweat and salt, but he doesn’t stop. With a brutal push, the widest part pops past my ring, and the whole damn thing settles inside me.
I scream, the sound raw and ragged, bouncing off the city skyline. My body shakes uncontrollably, my tiny cock pulsing painfully as my hole stretches to its breaking point. It’s impossibly full, pressing hard against my prostate, and beneath the agony, there’s a sick, growing pleasure that makes my head spin.
“Fuck, you’re stuffed,” he marvels, his voice thick with lust. “Look at that pretty little hole swallowing my torch.” He starts to fuck me with it, slow and deliberate, each thrust making my body jolt. The squelching noises are loud and filthy, mixing with my moans—half pain, half ecstasy—as I start to rock back against it, desperate for more.
“Yes, fuck me with it,” I beg, my voice hoarse, my mind a haze of need. “Make me your fucking slut.”
He grins, picking up speed, slamming the torchlight in and out. My small breasts bounce with each thrust, my skirt flapping uselessly around my waist, my panties stretched tight around my knees. I’m a mess—sweat-soaked, cum-stained, drool dripping from my lips—and I’ve never felt more alive.
Then, just as I’m teetering on the edge of another climax, he rips the torchlight out with a savage yank. I collapse forward onto my elbows, gasping, my hole gaping wide, sloppy and loose. But he’s not giving me a break. He hauls me up by my hair, the sting making me yelp, and bends me over the metal railing again. My hands grip the cold steel, my legs spread wide, my ass high and vulnerable.
His cock presses against my ruined hole, and it slides in effortlessly, no resistance left. “Fuck, you’re so loose now,” he groans, sinking in to the hilt with one smooth thrust. “But still tight enough to milk me dry.”
He starts to fuck me hard, his hips slamming into me, his balls slapping against mine with wet, rhythmic smacks. The sound bounces off the rooftop, mixing with my broken moans. My tiny cock bounces uselessly between my legs, hard again, leaking onto the railing. He reaches around, grabbing my small breasts, squeezing them roughly, twisting my nipples until I cry out.
“Gonna cum again, slut?” he taunts, his breath hot against my neck. “Do it. Cum while I fuck this sloppy hole.”
His cock hits my prostate with every brutal thrust, and it’s too much. My body convulses, my tiny cock spurting weak, watery ropes of cum onto the railing, my ass clenching around him. “Fuck, yes!” I scream, the orgasm ripping through me, leaving me trembling and gasping.
He doesn’t slow down, pounding me through it, dragging out the pleasure until I’m a quivering wreck. Then, with a final, deep thrust, he buries himself inside me and cums. I feel his cock pulsing, unloading deep in my ass, filling me up with hot, thick spurts. But he’s not done marking me. He pulls out mid-climax, grunting as he shoots the rest across my ass and lower back, the warm streaks splattering my fair skin.
“Take it all, you filthy bitch,” he growls, milking the last drops onto me. I feel it dripping down my thighs, pooling with my own cum on the concrete below.
I collapse fully now, my knees giving out, my body sliding down until I’m sprawled on the cold ground. My skirt’s a crumpled mess around my waist, my panties tangled around my ankles, and I’m covered in cum—his, mine, a sticky fucking disaster. My ass throbs, my hole loose and wrecked, and my fair skin is marked with red welts and bruises from his hands.
He steps back, zipping up his pants with a slow, deliberate motion, smirking down at me like I’m his masterpiece. “Not a fucking word about this,” he warns, his voice cold and sharp. “Or next time, I’ll fuck you so bad you won’t walk for a week.”
“Yes, sir,” I mumble, my voice weak, barely a whisper. I’m still reeling, my chest heaving as I try to catch my breath, my body buzzing with the aftershocks.
He turns and walks off, his heavy boots thudding against the concrete, the sound fading into the night. I’m left there, alone on the rooftop—used, humiliated, and fucking loving every second of it. I drag myself up, wincing as my sore ass protests, and start pulling myself together. I wipe the cum from my face with the back of my hand, tug my panties back up, and smooth my skirt down, though it’s pointless—I look like I’ve been fucked six ways to Sunday.
But as I stand there, leaning against the railing, staring out at the city lights twinkling below, I can’t help but smirk into the darkness. My tiny cock twitches again at the thought of it—how he owned me, how he broke me, how I took it all and begged for more. Maybe I’ll climb up here again tomorrow night. Maybe I’ll get caught again. The idea sends a shiver down my spine, a thrill I can’t shake.
I lick my lips, tasting salt and shame, and whisper to myself, “Fuck yeah, I’ll be back.”
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