"God, I need to fuck a sissy so bad!" Henry yelled, slouched at his desk in his cramped bedroom, supposed to be grinding out History 101 homework but lost in a loop of sissy porn instead. He’d swear the obsession owned him; those soft, obedient sluts hijacked his brain and left essays for dead. The thought alone of a perfect, whimpering sissy had his cock aching and his focus shattered.
Pants bunched at his ankles, boxers tangled with them, Henry gripped his leaking dick and stared at the laptop. A blonde bombshell named Sasha was getting railed by some ripped bull, her fat ass rippling with every thrust. Henry’s shaft glistened with slick precum, pulsing hot in his fist. He’d been edging to this same clip for half an hour, hips twitching, breath ragged.
Sasha was pure sin: rail-thin except for that obscene, jiggling ass built for worship. Golden curls spilled down her back, light-brown eyes sparkling with cock-drunk mischief. She always wore dresses two sizes too small, fabric stretched over curves that screamed breed me. Henry lived for the way she inhaled dick: plush lips sealing around a fat head, throat opening like she was born for it. Guys in her scenes lost their minds, roaring as they unloaded, knees buckling while Sasha milked them dry, never spilling a drop. Then she’d pull off slow, lick those glossy lips, and wink right at the lens; Henry had blasted ropes to that wink more times than he could count.
Right now, she was riding reverse cowgirl, tiny caged clitty flopping uselessly, dripping clear strings of precum as she slammed down. Henry’s own slit wept steadily, coating his knuckles. His balls drew up tight; he was seconds from painting his screen.
“Fuck it, I need the real thing now!” he growled, killing the video before he blew. Hand shaking, he snatched his phone, thumbed open Grindr, and scrolled like a man possessed. Ever since he’d learned the app was crawling with desperate sissies, he’d been hunting. He’d already throat-fucked a handful, but midterms had cockblocked him for weeks. Not tonight. History could rot.
One profile stopped him cold: Fiona, a brunette angel in lace. Pic after pic of her in panties so tiny they barely covered her caged clitch. Henry’s cock spat another thick bead of precum. Without thinking, his free hand wrapped back around his shaft, stroking lazy and slow while he read her bio: “Craving a thick cock to worship till it’s empty. 24/7 chastity princess. Make me choke on it, daddy.”
He fired off a message. Sixty seconds later, she replied, already begging for dick pics. Henry sent one: veiny shaft strangled in his fist, tip shiny and angry. Fiona spammed fire emojis and heart-eyes, whining that she needed it stretching her throat right now. She flooded his DMs with shots of her pink cage strangling that little clitty, then bent-over spreads of her smooth brown hole winking at the camera.
Henry damn near nutted untouched. “Get over here,” he typed, voice hoarse. Address sent. Door unlocked. Walk in and get on your knees.
“Ten minutes, sir,” she purred back. “I’m gonna swallow you the second I step inside.”
His heart jackhammered. He glanced down: cock glazed like a donut, strings of precum dangling from the slit to his balls. Before he could even wipe up, the front door clicked.
Fiona slipped in faster than promised, a vision in a black miniskirt and tissue-thin white top. Her perky hormone tits poked through, nipples stiff. Brown hair framed a face even prettier than her pics, maple eyes locked on his bobbing cock like it was god.
No words. She sank to her knees, skirt riding up to flash lace panties and the silver cage beneath. Warm, wet heaven swallowed his head. Those soft lips slid down his shaft in one greedy gulp.
“Holy fuck,” Henry choked. Real sissy throat beat any fleshlight. Fiona hummed, vibrations ripping up his spine as she slurped the precum slime right off him.
“Mmmph, mmmph!” She bobbed faster, tongue swirling the crown, cheeks hollowing. Henry’s thighs quivered; his balls churned like they were about to explode.
“Gonna—fuck—gonna cum!” he warned, voice cracking.
Fiona doubled down, throat fluttering. Henry roared, hips jerking as thick ropes hosed straight into her mouth. She gulped noisily, eyes watering but never breaking contact, milking him till his knees nearly buckled.
She popped off with a wet smack, cum glossy on her chin. “Yummy,” she giggled, licking it up like icing.
Henry hauled her up, spun her around, yanked skirt and panties down in one motion. That perfect caged clitty bobbed uselessly. Fiona reached back, spread her cheeks, offering that tight brown star.
Henry dropped and feasted. Tongue spearing, swirling, painting her hole with spit till it winked and glistened. Fiona mewled, pushing back, begging.
“Fuck me, please—need you raw!”
Henry stood, lined up, and sank in to the hilt. Her ass clamped down like a velvet fist. They both cried out. He gripped her hips and pounded, skin slapping loud enough to echo. Fiona threw it back, cage slapping against her thighs, little clitty leaking like a broken faucet.
She came first, hole spasming, squealing as clear sissy squirt dribbled out. The clench dragged Henry over the edge; he buried himself balls-deep and unloaded, pumping pulse after pulse into her greedy guts.
“Yes, breed me, daddy!” Fiona sobbed, milking him with every contraction.
Henry kept thrusting through the aftershocks, draining every last drop into his new favorite sissy, homework long forgotten.
