Tim was regularly spanked by his former nanny Diane and had already received his first good over-the-knee spanking from her daughter, Emma, with her hand and the heavy hairbrush. After the spanking, they discussed it and agreed it wasn't just a one-time thing. It was something that Tim both wanted and needed, and he was happy to have broken the ice with Emma. Being disciplined by her felt so right, and he was looking forw...

Tim has just recovered after another hard spanking from Diane, with Emma, watching. He sat in his room for almost an hour before his eyes cleared up from all the crying and his bottom stopped stinging so much. He also had enough time to masturbate and enjoy two fabulous orgasms. Going downstairs to the living room, he found Diane sitting and reading a magazine. Emma had gone to meet some friends, so it was just the two of...

Tim was in his bedroom, recovering after yet another great post-spanking orgasm. They were the best and most intense orgasms. Just thirty minutes ago, Tim was over Diane’s knee, having his bare bottom soundly spanked with a heavy wooden hairbrush. He didn’t do anything wrong and actually asked for the spanking exactly as he has done almost weekly for the last few months. His life was not always happy, and his childhood wa...

It's been four days since eighteen-year-old Tim's life took an unexpected turn. Four days since he was spanked for the first time in his life, after years of dreaming and spanking himself, trying to substitute the need to be spanked. He tried so hard to find the right person for this important job, and that person was always around, but it took him years to realize that. After some unexpected events and after complicated...

It was a beautiful spring day. Tim had just come home from school and was sitting on the sofa watching his favorite TV show when he heard Diane, entering the front door. She went shopping and had her hands full of bags. Tim was eighteen and was in high school. He was one of the best students in the school, well-behaved, very respectful, and appreciated by teachers. Tim lived only with Diane. She has a daughter, Emma, thre...