Robin's Failure

The middle-aged man looked up from the hot iron on the ironing board, meticulously removing the creases from the business suit.

The female voice barked once more. "Robin!"

His seductively-dressed mistress stood in the doorway. She glared at the man, dressed in a pink maid's outfit, as he curtsied demurely. "Yes, Miss."

"Pierre has finished in the garden. Wash his tools when you've finished ironing and wash his clothes." He nodded respectfully, and then she added. "You know it's the 21st today. Be ready for me. I'll be back at eleven."

She swung her long pale cloak over her black Latex bustier and matching stockings and shut the door to the small utility room behind her.

Jordan, the youngest daughter of six had inherited a considerable sum from her father, a property tycoon and retail magnate, when he died a few days before her twenty-fifth birthday. The hedonistic nymphomaniac possessed a mile-wide sadistic streak, and her live-in companions received plenty of attention.

Robin was one of them, and an ex-employee of her father. Seven years ago, he claimed not to know the real age of the girl he bedded, but a subsequent investigation uncovered unsavory material on his computer and the court took a dim view of his peccadilloes. On leaving the justice system, he had no home, no life, and the conviction acted as a millstone around his neck.

Jordan gave him a lifeline. His clerical and advisory duties were replaced with servile, menial tasks. She replaced his clothes with skimpy outfits or nudity, and gave him a tiny bedroom in the cold basement of her opulent Moulton Abbey estate. Over time, she tightened her grip on his life. Jordan confiscated his driving license and made him use the bus whenever he needed to leave - the 47 from the main road to the town center or the 55 to the sex club and store. She made him surrender his phone and his bank account, ensuring that he only watched the TV shows and pornography that she allowed.

Five years ago, after a drunken night at her favorite sex club, she forced her slave into one of Gemma's dresses. The ridiculous sight caused her to guffaw and Robin's erection to ripple the tight lycra. She noticed, and swapped his clothing with overly feminine outfits, especially when out in public. Jordan shredded his "normal" garments, and he wore unsuitable, humiliating slutwear wherever he went. The theater, the supermarket, the auto garage and even when shopping in Regent Street. Back Alley Whore was his new look.

A chastity cage was quickly introduced by the sadistic dominant and she used her strap-on dildo on him one evening to humiliate him. It caused a damp, creamy patch in his lacy panties to form as the dominating woman pounded his rear. A feeling he had never experienced before, and he begged for more.

It intensified their relationship considerably. Before, she humbled him as punishment for the bad publicity his trial caused her father. Now, she could degrade him and humiliate him - and he reveled in it. They both needed it. Robin was her release valve.

The pegging became a daily ritual for a year. She had a selection of dildos from casts made by previous partners and some of them frightened poor Robin. James Smith and Brendan were bad enough, but Patrick's "bratwurst" stretched him and the Joe Dulcetti caused him to tremble in fear and excitement.

Over time, the pegging became less regular, and on the 21st of each month, Robin would be unlocked from his cage before she penetrated him. They had a wager, and one that he had not won in over four years.

That evening, he finished the ironing, cleaned the dirty gardening tools until they shimmered in the sunset and then washed the French gardener's clothes in the washing machine. He could smell the exertion on the grubby blue cotton, and he sniffed the underwear of the muscle-bound tradesman. Jordan had caught him once before and had given him twenty strokes from her favorite cane.

After his duties, Robin douched himself. The tepid rush of water flooding his backside was a common feeling in the cold, unheated toilet of the basement. Mistress had demanded. His domme had ordered him to "be ready" and he grunted as he slipped a butt-plug into his lubed anus.

Jordan arrived home after eleven. The slightly tipsy woman called for her slave, and giggled when Robin, still wearing the ridiculous Maid's outfit, curtsied. "Diana was at the orgy. The one from the Real Housewives of Cheshire. She had her little slave with her too and we might get you two together although she's eighteen so probably too old for you!" He blushed and looked away as she advanced on him. "You ready, slave?"

"Yes Miss." Her high heels tapped and echoed on the marble as she crossed the floor and grabbed her pathetic bitch by his pink collar. Jordan pushed her slave towards the stairs and he scurried to the windowless bedroom.

"This is the fiftieth time and you've lost every bet so far," she reminded her disgraced slave as her strong arms pushed him backwards onto the bed. His butt bounced on his singled mattress, and she pulled his pink lacy polyester panties to his ankles. The key on her necklace liberated his cock from his chastity cage for the first time in a month, and she sniggered as his dinky dick flopped free. "It's getting smaller and smaller," she laughed.

She opened her handbag and rummaged around. Jordan held a sandwich bag in the air, containing two used condoms, tied at the opening. The pearlescent liquid in the teats swilled and she extracted them. Her fingers delicately placed the full cumbags in Robin's mouth and she pushed his jaw closed. "Your present from the orgy," she explained. "Leroy and Jamal were very big. And they wanted an evening with you at their club. I said they could have you when I win tonight."

Robin closed his eyes and groaned as his prick hardened. The sweet taste of degradation. He gasped as she removed the butt plug and let the metal toy fall to the floor. The Latex-clad woman selected a pink dong from the shelf and slipped it inside a harness. Her fingers dug into his splayed thighs, and she lined the dildo with the pink orifice of her slave.

He gulped as the smooth rubber phallus slid into him and rubbed his prostate, biting down on the rubber condoms. He could taste and smell the synthetic chemical aroma and felt the goo slip inside the thin sheath. His dick bobbed as his mistress slammed the fake cock in once more. And again.

She hammered his backside. Pounded him. Rogered him without mercy as her cock smashed into the middle-aged man.

He grunted, breaking the Latex teat. Cum dripped into his mouth as his mistress powered her strap on into him. He gasped and squeaked as his arousal peaked and surged from his loins. He could not control his lust and his tiny rock-hard prick shuddered in mid air. A few squirts of his seed sprayed up his silky sissy attire.

"Sixteen seconds," Jordan laughed. "That's four less than last month." Robin mewed pathetically as she unclipped the harness and tossed it onto his chest. "You'll never win your bet, will you?"

"No Miss," he muttered. She smiled, and pointed towards the door. "Get cleaned up and then we'll lock you back up." Her slave scrambled to his feet and ran towards the door. "And it's another tattoo, Robin."

"Yes, Miss," the pathetic man squealed.

Robin's bet was simple. He would be freed, and she would write him a check for a hundred thousand pounds, if she could butt-fuck him for two minutes without him orgasming. And for every failure, she had her tattooist ink him again. Forty-nine humiliating, subservient and degrading tattoos had already been inked upon his body, legs and arms. Number fifty she promised to let Jamal and Leroy choose, after they had done their sinful acts on her shameless slave, while his manhood was locked in the neon pink micro chastity cage.