The chastity was torture enough. He had his cock locked away by his landlord for months now. The agreement seemed like a good idea at first - his rent would be slashed, so long as he wore the chastity cage and did what the landlord ordered him to do. Every three months, he would be presented with a choice: pay the rent in full and remove the chastity cage, or pay half the rent and continue living in servitude. He had been in chastity for almost six months now. But the chastity itself wasn't the most humiliating thing... it was everything else.
Tonight was Tuesday, which meant the college student had to sit and watch as his landlord fucks his fleshlight, edging himself with the toy. He pumps his hips up into the slimy mouth, the lube dribbing down his hairy balls and onto his taint. He sometimes grinds his hips downwards into the mattress, deep-fucking the fleshlight. It drives the tenant wild. His cock strains against his cage, bulging obscenely around the metal bars. He does everything he can in his power to give himself some pleasure. He tweaks at his nipples, fondles his balls, sometimes even slips a finger into his hole, but it's never enough.
The man always finishes with a roar of pleasure, his feet scrunching and his toes curling as his balls throb and empty themselves into the toy. His thighs tremble and shake with orgasmic aftershocks. Eventually, he pulls the toy off of his fat cock and lets the cum dribble down his still-twitching shaft. The tenant could almost sob at the display of raw sexual power that he's been denied - and sometimes he does. Sometimes his caged cock gives out a spurt of pre-cum in sympathy. Soon after the landlord lets his spunk coat his cock, the stream shuts off, leaving the poor tenant denied, staring at his throbbing caged cock.
(picture courtesy of @wlporn100!)