Wooden spoon spanking Stories

“6:15. Be Ready.” I read the email from my administrative assistant, Evan. Evan might be my assistant during working hours, but he is also my dominant. Be Ready. That could mean a variety of things. We had a busy day filled with meetings ahead of us, so I knew it unlikely I’d have a chance to ask for clarification. Nonetheless, that niggling mix of excitement, worry, anticipation, and a tinge of fear lay just beneath the...

Pete's neighbor was a hot single mom in her forties. Being the horny teenager he was, Pete took every opportunity he could to catch a glimpse of her. He thought he was being inconspicuous, but his clumsy attempts to steal some eye candy were quite obvious. While she noticed, she really didn't mind the attention. She admired his innocence and internally desired to give him what he wanted. As he grew into young adulthood, h...

Pete, twenty years old, needed a haircut but was tired of the same old generic cut he got at the local barbershop. He searched online for an alternate option instead. He found a listing of personal ads for hair cutting services, and his eyes were drawn to one ad with a headline that said, "Haircuts Available for Good Boys," with a picture featuring a woman holding clippers. Her face was turned away from the camera, hidden...

The cliché hot stepmom fantasy was real life for Pete. He had just graduated high school and was living at his parents's house, trying to save up money for college. His dad got remarried a couple of months ago to a beautiful woman in her mid-forties. She was very sweet and kind to Pete. He found it awkward to call this bombshell mom, but she insisted, and he became more comfortable with it over time. She always wore skimp...

Pete was behaving himself well after his first spanking two weeks ago. He was completing his math homework, and his tutor was quite satisfied with his performance. Pete loved impressing her and started to apply himself to his schoolwork. Despite his progression, though, a feeling was building day after day inside him. Pete was itching to get another spanking. He was a little hesitant to act out, though, because the last t...