Sissy Maid

His only desire was to be the best sissy maid that he could be and she had done a wonderful job of teaching him how to perfect his services. She had ordered him to wear a maids outfit with white seemed stockings, garter, thong panties and the perfect black maid shoes.

He was not allowed to ever have direct eye contact with her and he was always to address her as Miss or Madame. His meager quarters were in the furthest corner of the basement and his room was 6 foot wide by 8 foot long. It was his responsibility to wake up at 4 a.m. every morning, make his bed and dress to her specifications.

His shoes had to be polished nightly and the seams on his stockings had to be straight or she would severely punish him. It was his duty to see that she was served hot tea every morning by 8 a.m. and she demanded a small bowl of steel cut oats with brown sugar and a splash of milk.

Once she had finished her breakfast it was his responsibility to see that her clothing of the day was without a single wrinkle wrinkle and God forbid that there be a stain on a blouse, jacket, skirt, dress or pair of pants that she owned. He had made a terrible error of letting her leave the house with a small stain on her skirt and when she returned home she ordered him into her dungeon.

She handcuffed him to the wall making sure that his nose pressed against the cold wall and she shackled his ankles. She brought out her favorite paddle and floggers and spared him no mercy as she paddled his ass crimson red and flogged him. She left him with welts on his back and the she got out the hot wax.

He had not shaved his legs in two days which was a sin in her eyes and she poured the hot wax on the back of his legs and then she applied the hair removing strips and applied them to his legs. She pulled them off with one swift pull and she would then run her hand over the bare spot saying how nice it felt.

She continued to do this until every hair on the back of his legs had been removed and then she undid his ankles and hands and ordered him to turn around. She handcuffed him and shackled him to the wall this time facing her and she continued to was him from his chest to his toes. It was very uncomfortable to have her put the hot wax on his balls and then rip the hair removing cloth from his balls and he screamed out and she could see the tears springing from his eyes.

Once done with the wax removing she undid him once again and ordered him to kneel on the bench and she cuffed him and then applied leather straps just below his elbows and attached them to the rings on the bottom of the bench. She then walked around and rubbed his ass and then inserted the butt plug firmly into his ass.

She then began to stroke his cock as she spoke to him gently and with the kindness one would never expect to receive after being so careless. She asked him if he would like to cum and if he like her fucking his cock with her hand and of course he said “yes miss, very much so miss” and she asked him if he liked her fucking his ass with the butt plug and once again he said “yes miss, very much so miss.”

He was just about ready to cum and she stopped and walked over to her drawer full of toys and pulled out her crop. She slapped his aching balls and cock and told him he didn’t deserve to cum and if he did she would force him to suck the cock that was stuck to the wall and she would fuck him with her new strap on which was huge in diameter and length.

The thought of her abusing his ass made his cock throb and he begged her to please allow him to release his seed. She refused to allow him to do so and she told him she had a gift for him. She removed a brand new cage and applied it to his cock and put the key on the chain around her neck and told him he would wear the cage daily and she would remove it long enough for him to shower then put it back on him.

She could be so cruel but he loved her so much and even her punishment was something he looked forward to at times. His mistress was difficult to please but she would reward him handsomely when he performed to her satisfaction. She never let anything slip by her and she paid close attention to his work and this made him feel so desirable which made him do everything to keep her pleased.

 

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