“This is perfect for the job. Keep your buttocks spread. You only have yourself to blame after all.”The brush made contact with the cleft of my anus: it was way more painful than anything that I had experienced so far. The brush visited all along the valley of flesh I was so lewdly displaying. I kicked my legs, cried out, begged, but Mistress was determined I was to be thoroughly punished.Just when I thought I could take no more, Mistress stopped. “Now that is a properly spanked bottom. Your wife would be impressed. How do you feel?”“Very sore, Mistress.”“Not as sore as you are going to feel, but we have made a good start. Right stand up and back in front of the desk.”I stood as requested. My penis that had lost its enthusiasm whilst being spanked swelled again. I was after all naked in front of a beautiful semi-dressed woman. Unfortunately, I did not think her plan included entertaining my penis. All her plans seem to revolve around making my bottom suffer.She picked up the paddle. I remember one day we were hanging out and she showed up with another girl about our same age. Alex said that was his girlfriend. His sister sat down with us, eating some chips. The other girl sat next to Alex and they began making our a bit. Alex reached up her skirt, pulled her panties down, and went between her legs missionary style. The girl seemed elsewhere, she would moan with every thrust Alex gave her, but she didn't do much else, just lay there with her legs open. Her moans were really loud, it even sounded like she was in pain. But she kept taking it. Her moaning is something I remember to this day. It was the first time me and Caeser saw sex, so we didn't really understand the whole concept. Alex's sister sat there watching and eating her chips, like it was nothing. Alex finished and his sister walked away. She came back with a roll of toilet paper, that she handed to her friend that was still laying there. She took the roll and wiped her pussy. Throuhout the whole.
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