The Longest Night

David sobbed as the searing pain of the hundredth stroke speared through his buttocks. He had never known pain like this. Mistress untied him and drew him to her. She hugged him and stroked his hair.

‘Brave boy. Mistress is proud of you.’

David continued to sob. As he felt Mistress’s breasts rise and fall, felt her warmth and soft skin he felt shame that he had let her down again. She stroked his hair again then clasped his chin forcing his head back so that he had to look her in the face.

‘Next time I will not be so gentle.  You are going to take your submission more seriously. When I say that you are in chastity I mean precisely that. You will go away and reflect on what has happened today. You will obey me. You will learn self control and if you have to do it the hard way so be it. You will phone me every morning and give me a full account of each night. You are dismissed.’

At bedtime that night David  knelt by the bed and asked his Mistress for the strength to get through the night unsoiled. He put on the silk nightdress she had given him, that made his cock just that bit less accessible and pulled on the plastic underpants he had been commanded to wear each night. Finally, as a final defence against temptation he pulled on a pair of pink rubber gloves. In these, at least, it would be difficult to wank. He sat up in bed for a moment, holding Mistress before him, before lying down and clicking off the bedside light.

He lay on his front at first, as an old book about the dangers of self abuse suggested,  but soon found himself rubbing his crotch against the sheet. He turned over onto his front and placed the gloved hands outside the duvet. He imagined Mistress looking at him thorough a spy hole. Sleep didn’t come and he realised that this would be a long night, a lonely battle against temptation.

As he lay there, tossing and turning, Mistress began to appear to him, first in a latex dress and stilettos, the ones he had worshipped recently, then in tight PVC trousers with red thigh boots that gleamed in the lights of the dungeon. He felt his hands reach to pull up the nightdress and he began to pump his cock with a gloved hand. As the precome dribbled out over the pink glove he stiffened in horror and pulled his hand away.

‘I just obey I must obey’ he repeated breathlessly.

He rolled over into his front and pushed his hands underneath the pillow. He slept fitfully for a while before Mistress came into his head again, this time in a red PVC dress and black boots. She bent over the arm of a chair and lifted the dress to reveal the new tattoo on her left buttock,. David saw himself creeping forward on his knees to kiss the tattoo slowly and lovingly.

He rolled over. He was hot and sweaty. He pulled off the rubber gloves and again reached for his big hard cock. Mistress was now standing over him, commanding him to come, pushing the sole of her boot into his face. He looked up.  She seemed even more magnificent from this perspective, pushing down harder commanding him to lick the soles, to wank his cock harder. He pumped, he kneaded the tip, he pulled the foreskin back and as he felt the ejaculation surging  up the shaft he remembered and took his hand away just in time.

He sat up in bed panting and switched the light on. He was hard, he was desperate to come, and yet………

‘I must obey, I must obey’

He was hot and uncomfortable in the plastic pants and pulled them off, looking at the precome that stained them. He felt shame. He looked at the clock on the bedside table. Four o’clock. It was starting to get light. He had two hours to endure. Mistress had told him that chastity would be hard but he had to do it, he wanted to do it for her. He must obey. He switched the light off, lay down and fell into a fitful sleep.

Mistress was soon back, peeling off. a shiny dress to reveal her breasts, a tattoo above the left one. She stood before him in boots and  nothing else. She turned round and flaunted the tattoo on her buttock, backing up to the bed for him to kiss it. Then she turned to face him and he saw her shaven cunt, saw her fingering her clit.

‘You’d love to but you never will.’ She laughed a long demonic laugh.

‘Look at it,you’ll never see another one, you’re in chastity, eternal chastity…’

She laughed again as she disappeared. The alarm rang. The sun was streaming  in  through the window. He reached for his cock, pumped and massaged and the thick creamy come was soon running down his leg. He turned over and rubbed his crotch hard against the sheet. It was wet, it was warm, the unmistakeable smell filled the room. There was a large damp patch on the nightdress..

He panted with relief, He had hardly slept. His head ached. Then came the dreaded realisation that he had failed, He had disobeyed. He had advanced no further in his submission.

He reached for his phone and dialled Mistress’ number.

‘Forgive me Mistress I have sinned’ he said as tears rolled down his cheek, tears of shame, of joy too. He would surely learn to love the cane.

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