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Hairbrush spanking Stories

hairbrush spanking

Neighbor III

Pete thinks he can escape punishment by moving. His neighbor thinks otherwise

A few years passed since he was last spanked by his neighbor, and Pete had moved out of his parent's house to an apartment not far away. He hadn't forgotten her and longed to be punished by her again. She hadn't forgotten him either and wished he still lived next door, so she could punish him for his misbehavior. Pete was running errands and happened to see her at the grocery store. Familiar pangs of excitement and fear r...

Neighbor II

Nosy Pete gets caught and spanked

Pete couldn't imagine taking another spanking from her. The last one hurt so badly. Eventually, though, the thirst to be punished came back. He didn't know how to go about asking for another, but he didn't have to. The opportunity presented itself one lazy Saturday afternoon. As she often did, his neighbor was spending the afternoon sunbathing by her pool in the backyard. Pete knew this was his chance. Throwing his fears...

Law II: Rosie. Part I

An old lady reminiscing

"My fascination with spanking began long before I met Molly, you know." "Rosie, you obviously want to talk about it, don't you?" "If you don't mind, Barbara," Rosie answered. "Of course, I don't mind. We've talked of so many things; it really was only a matter of time. It's so long ago, I thought you may have forgotten." "Well, Barbara. Where would you like me to start? Of all the things my life amounted to, it was one of...

Neighbor

Nosy Pete gets spanked by his next door neighbor

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...

Tim's Painful Yet Rewarding Journey- Chapter V

Tim is caned for the first time, but not the last

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...

New Beginnings - Phil Me In - Pt. 3

Maddy and Tracy enact the plan they'd cooked up in the kitchen the prior weekend.

Maddy and Phil had dinner together to get to know each other better, which was an interesting situation since they’d been neighbors for so many years. They avoided the topic of the day, but it was still ever-present in their minds, and as the evening progressed, Phil felt better about his future insofar as his kinky desires were concerned. All three parties to the day’s extraordinary events had reasons to be excited about...

The Couple That Spanks Together - Part 16: Properly Motivated

Bertie's taking on too much pressure, and Rachel knows how to release it

It had been weeks since Rachel’s last gig. It was the beginning of the summer season, and the university students who had packed the club to hear her spin tunes and sing every weekend since September had gone home. Her business was quiet, and she’d only recently started to search the want ads looking for something to pay the bills for the next handful of months. Bertie knew from experience that little was going to come fr...

Haircut

An F/m Spanking Story

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...

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Night Desk - Back For More - Pt. 2

Jim & Shelley resume their early morning hijinx with an expanded repertoire

Given his late-night activities, he woke later than usual, just in time for breakfast in the hotel. He went to the front desk hoping to find Shelley and was disappointed that she’d left at eight when a colleague arrived to relieve her. He wasn’t sure what he would say to her, but having promised to return, he’d hoped to get her shift schedule. ‘She probably doesn’t really expect me to come back,’ he undersold himself when...

Tim's Painful Yet Rewarding Journey- Chapter III

Emma returns from college for the summer holidays.

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...

The Couple That Spanks Together - Part 10: Trading Places

Rachel learns about Bertie's hidden fantasy, and sets a trap

The sky was clear, the sun shone, and Bertie was standing back in the apartment that he shared with his girlfriend. He rolled his neck as he stepped through the door – the heavy snow had forced him into staying at his mother’s house for the last two days, and her guest bed was far more rigid than the mattress he was used to. While he appreciated having a place close to work where he could stay, he was far happier getting...

Stepmom

Pete struggles to ask his stepmom for a spanking

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...

A Surprise For Max

Heather plans a surprise for Max

After another surprise visit by his favorite neighbor, Max gave Heather the combination to the back door lock. That time, she was completely naked, lying in his bed with a beautiful smile on her beautiful face. Grubby from working outside, she followed him into the shower and bathed his entire body for him, giving special attention to his seemingly always-erect cock. He returned the favor with a tongue bath between her le...

Spanks For Pranks - Lisa - Pt. 2

Kailee's tattling to her daddy has surprising results!

Lisa sat in the coffee shop trying to read a book but couldn’t focus on it. The remnants of her last spanking, just three days ago, had faded from her bottom but not from her mind. She felt like she’d taken her punishment for her perceived responsibility for screwing up her marriage to James with the second visit to ‘Spanks For Pranks,’ when Jeff lit into her with the hairbrush. It hurt so much, but she’d egged him on, fe...

The Couple That Spanks Together - Part 2: Peeping Tom

Bertie's turn - In which much is considered and little actually transpires.

There was no doubt about it, they were an odd couple and had been right from the beginning of their courtship. Bertie had a degree, worked as a restaurant manager, and spoke with the tone and elocution of a university lecturer. Rachel worked part-time as a DJ, had never gone to college, and seldom got out of bed before noon. Those who speculated about their relationship supposed that Bertie’s attraction to his petite, you...