f***ed to cross dress on Halloween - Sex Stories

f***ed to cross dress on Halloween

... “No… Nothing mistress.” I kept my grip on his balls as I continued. “Why don’t you thank me.” “T…Thank you.” “You can do better than that.” “Thank you mistress.” “For what?” “Fo… For helping me get dressed.” “And?” “Selecting my outfit.” “Good girl. Now, we don’t have much time. I want you to start vacuuming the house, then clean the bathroom and lastly the kitchen.” “Okay.” Who did he think he was? For one last time, I squeezed even harder while I almost yelled. “Okay what?!” “Yes mistress.” He responded in a high pitched tone. Finally, I released him. As he walked past me, taking baby steps in his high heels, I slapped his ass. It sure was lovely having a maid do your housework. *** I could hear the water running in the kitchen. I was getting ready in the bedroom, stepping into the harness straps. After pulling the whole instalment up, I tightened the straps so the big dildo was firmly pressed against my mons. My maid was too busy with his chores to hear me approach him from behind. He almost jumped as I told him to turn the water off. Still standing behind him, I guided him towards the kitchen table. I f***ed his legs apart while I pushed him forward so he was bending over onto the table, his elbows propping him up. I undid the straps of the pinafore apron on the back and grabbed his left wrist. I guided it behind his back and wrapped the soft material around it a few times. His right wrist followed. “Now, you have been a bad girl today. I have to make sure you will ...

... behave tonight when the guests are here.” I said while tying his wrists together with the apron strings. I lifted up the skirts of his maid’s uniform. “Guests?!” He anxiously asked. “Of course dear. Some of my friends are coming over.” My hands found his panties. “I… I don’t know Deborah.” I could feel him pulling slightly on his bound arms to check if he could move. I knew he couldn’t get out of it and so did he. I had enough experience with bondage to know how to effectively tie someone’s hands together. My hand moved to the front side of the panties where I could feel a big wet spot. He was dripping through his cage, soaking his panties. “What don’t you know?” I asked him while slowly lowering his panties just enough to expose his bare ass. “This is fun and all, but I can’t be seen like this.” He pleaded. “Oh, but how can I keep you to myself? I put so much effort into your costume.” I said mockingly as I slowly started pulling out the butt plug. “Ughh… no, but seriously Deb.” He tried again. I had heard enough. The lubed up butt plug was now completely out and I dropped it onto the floor of the kitchen. I lifted the skirt of the dress up so that he was fully exposed. “I think you need to learn a lesson.” I stated as I guided the tip of the big dildo towards his ass. “But, Deb…” He tried once more. With my left hand I parted his butt cheeks a little bit so I could see the stretched hole which was going to be punished for his remarks. Slowly, I moved my hips forward until the ...