[cd] Crossdresser Dominated By Mistress

The Crossdresser’s Demise: A Naughty Tale

In the heart of a cramped basement apartment, devoid of natural light and decorated only by faded posters of scantily clad models, lived a young man named Chad. By day, Chad was an unassuming provocateur, slaving away in an insurance office, his bland existence punctuated only by the occasional vending machine snack or idle chit-chat with co-workers. But when the sun set and the city settled into a slumber, Chad would don a wig, apply lashes, and channel his hidden transgender persona, Chastity.

Chastity was a dominate siren, a vixen who reveled in the application of whips and chains. She longed to wield power over others, to put men in their place and fill a room with their pleas for mercy. And tonight, a young buck named Tommy had crossed her path.

Tommy was no match for Chastity. He was a lanky kid, all boney limbs and scruffy hair, lost in the ways of love and lust. Chastity had lured him in with a sultry wink and a whisper of promises. The poor boy thought this was his lucky night, that he was in the presence of a gentle female, not the dominatrix that awaited him.

Chastity smirked as she watched Tommy wander into her lair, the boy’s eyes darting around the dimly lit space. She loved the look of fear that crept across his face as he realized exactly what he had gotten himself into. With a snap of her fingers, Chastity called two onlookers to Tommy’s side.

“Make this boy strip,” Chastity demanded, her tone haughty and commanding. “Remove his clothes, but leave his boxers. I wish to admire his goods.”

Tommy stumbled as the two grabbed him, fearful of the wrath of this dominatrix if he resisted. Chastity let out a wicked laugh at his plight, twirling a riding crop in her fingers as she eyed the exposed young man. He was a scrawny thing, his chest narrow and hips wide. But he was cute, in an awkward sort of way. And he would be fun to toy with.

Chastity ordered Tommy to present himself in a spread eagle stance. The young man trembled as he complied, his exposed cock twitching in anticipation despite his fear. Chastity moved in close, trailing the tip of her crop lightly across his chest, circling one taut nipple before moving on. She dragged the implement down his quivering body, ghosting it just above his caged cock.

“You may beg now,” Chastity purred, her eyes glinting with sadistic glee. “Beg me to torment you.”

“Please,” Tommy whined, his voice cracking. “Please Mistress, I need you to whip me. To hurt me.”

Chastity tutted. “Boring. Try harder, faggot.”

The young man’s eyes widened and he shook his head frantically. “Mistress, I’m not a faggot! I love pussy! Please believe me!”

“Less talking, more begging,” Chastity snapped. She flicked the crop against Tommy’s exposed erection, making him yelp. “Start by worshiping my black boots, you pathetic worm.”

Tommy scrambled to the floor, burying his face against Chastity’s glossy leather boots. He mewled like a needy puppy as he licked and kissed the smooth surface, desperately seeking her approval. Chastity ground her heel against his chest, forcing him to arch his back and present his bottom.

“That’s it, pet,” she cooed. “You’re learning.”

Tommy let out a keening wail as the first harder strokes of the riding crop made contact with his tender ass. Chastity was relentless, raining down blows on his upturned bottom until the flesh was an angry red. The young man’s skin was slick with sweat, his shuddering moans filled with a pleading mix of pain and grotesque pleasure.

“Look at you,” Chastity mocked. “A whimpering mess and we’ve barely gotten started.”

As promised, she made Tommy eat her ass, plunging his face between her cheeks as she cackled at his plight. All the while, the young man’s cock remained at attention, his arousal undeniable despite his proclamations of straightness. Chastity made sure to clip his testicles tight with clothespins, watching with cruel amusement as his buried his face deeper still, overcome by sissygasm.

When she was finished, Chastity released Tommy. The boy curled in on himself, tears and snot smearing his face, entirely unaware of his present state of undress before a crowd ofObservers. Chastity ran a finger along his jaw, savoring his whimpers.

“Go home now, little piggy,” she cooed. “Keep dreaming of me. Because next time, pet, you’ll worship my cock.”

Blindly, Tommy crawled to gather his clothes, shame coloring his cheeks. But Chastity could see the reluctant yearning in his eyes, the ever-present hardness in his loins. He was a pathetic, hopeless mess. But he was her mess now, to torment and use as she saw fit. And she would call on him again, on that she would make sure.

The End.