"Have you found anything interesting?" Jacob asked as he opened the thirty-fourth box of the day.
Jacob and his colleague Anne were teachers in one of the oldest schools in the county. Some of the rooms in the basement had not been used in decades, and the principal wondered if some of them could be cleaned up and used again. Unfortunately, most of them had been filled with clutter, which meant that someone had to go through the room and throw out everything that was no longer needed. Jacob and Anne were the only two that volunteered.
Jacob suggested to Anne that they should keep an eye out for anything unusual, funny, or interesting while cleaning, to provide a bit of entertainment. "You'll always find something old and fun in places like this," he said. "Just you wait." Anne knew he was a bit of an oddball, but he could be quite charming.
"I haven't found anything in particular. How about you?" Anne replied as looked around for another box to place on the table.
"I found this. Interesting enough for you?" When she turned around, Jacob was holding an old cane which had probably been hanging in a wardrobe. He grabbed the handle and swung it through the air a few times, smiling to himself at the whistling sound. "Brings back memories."
"I'll have you know I was a well-mannered boy," Jacob said with his nose in the air. "I'll admit to being caned once or twice, but far more often, I could see or hear my less well-behaved classmates feeling the pain. Incredibly fun to watch the most stuck-up girls in class dancing around with both hands clutching their backside as if fearing it would fall off." He whirled the cane between his fingers in an unusually poor impression of a baton twirler. "How about you?"
"They didn't use the cane at my school. They stopped a few years before the ban, so you could say they were before their time." She shrugged. "I've never felt the cane, no."
"It's never too late," Jacob replied with a small bow. "If it would please the lady to bend over the table in the corner, I will handle the rest."
"Stop being stupid," she replied and poked her tongue out at him. She bent over to pick up another box, but jumped to her feet when she felt something smack into the seat of her jeans. She spun around to face Jacob again.
"I know you don't have any experience with this," he said while trying to look strict. "But it's not wise to insult someone who's standing behind you with a cane. It could have consequences."
Anne hurriedly rubbed her backside, and realized that she was blushing. The stroke had not been hard, and the shock was greater than the pain. "Well, in that case, I apologize, and I hope you can forgive me," she said with a sarcastic curtsy.
"I can," Jacob said, and he bowed his head before placing the cane on a table and continuing to clean. Anne rubbed her bottom again and picked up a box.
Fifteen minutes later, Anne was beginning to wonder what was wrong with her. She could no longer feel the little slap that Jacob had given her, but she was still sneaking her hand back to rub the place where the cane had landed. And if she tried to resist the urge to rub, both her hand and her rear would tingle until she gave up. She was glancing over at the cane all the time, as if trying to make sure it hadn't gone anywhere while she was cleaning. Why was she so obsessed with the little piece of wood?
She slowly realized what was wrong. The conversation with Jacob, and the little smack she'd been given, had awakened her curiosity. And she could only think of a single way to satisfy it.
Jacob was sitting on the floor going through some folders when he suddenly realized that Anne was standing over him. She was biting her lip, and he had a feeling she was trying to hide her nervousness. "What is it?"
"Is your offer still available?" Her voice was calm, and she tried to give him a carefree smile.
"What offer?" he said as he stood up.
"The cane," she said, nodding toward the table. She opened her mouth as if intending to explain further, but nothing came out, so she closed it again. She didn't think he'd need an explanation, either.
Jacob stared at her, before shrugging his shoulders. "My services are available if you want them, Anne. If you bend over the table, I will take care of the rest."
Her knees shaking, Anne approached the table. Jacob barely managed to stifle a moan as she bent over. An outstanding backside, framed by a pair of tight jeans, met his gaze. Anne was truly a good-looking woman. He lifted the cane and whistled it through the air, grinning as the sound made Anne quiver in anticipation.
Anne gasped in surprise as the first stroke landed, followed by the second and third, and a slight heat was beginning to spread. Unlike the schoolteachers of his childhood, Jacob used quick, light strokes. He had no intention of hurting or scaring her.
"How is it going? How does the cane feel?"
"It stings, but in an interesting way. Not very unpleasant," Anne replied. "I assume you would usually strike harder than this."
"Much harder," Jacob admitted. "But since this not a punishment, I decided we could start slowly. I can hit harder, if you want."
"Not on my account," Anne said with a shiver.
A few minutes passed. With every stroke, Anne's backside grew hotter and hotter, and when the cane lines crossed each other, the burning pain increased. Suddenly, Jacob lowered the cane. Anne turned to look at him, surprised to feel a tinge of disappointment. "What is it?" she said as she saw the blush on his face.
"Well, that's the thing about canes," he said. "They weren't usually used over your trousers…"
Anne felt a nervous tingling in her stomach when she realized what he meant. "You're only saying that because you want to see my naked butt," she said playfully.
"You wound me," he said theatrically. "That's not the ONLY reason."
Anne barely hesitated before pulling the jeans down to her knees. She had already bent over a table so that her colleague could cane her. This situation was already embarrassing. Making a quick decision, she grabbed her panties and lowered them as well, before bending down and poking her naked bottom in Jacob's direction.
Jacob took a step forward, stretching out his hand to feel her backside. He gently touched her soft skin, rubbing some of the sting away, and could feel himself growing harder. Anne was one of the most beautiful women he'd ever met.
"Hey!" Anne said, trying to sound offended. "Are you spanking me or groping me?"
"I don't see why I have to choose," he said petulantly, as he picked up the cane.
Anne groaned as he continued the 'punishment'. It shocked her how much more painful it felt on her bare skin. At the same time, her pleasure grew stronger as well. The pain in her backside was accompanied by a delightful tingling between her legs.
They had no idea how long they continued, but when Jacob finally placed the cane back on the table, Anne could feel tears rolling down her cheeks, and her bottom was covered in red lines.
Jacob held her close, whispering soothingly as he wiped away her tears. Anne surprised him by kissing him on the lips, and there was an inviting look in her eyes.
"Your place or mine?" he asked with a smirk.
"I think we should go back to my place, but there is one thing I'd like you to do first," she said.
"What is it?" he said. With a prospect like that, there were few things he wouldn't be willing to do.
"In my desk drawer, I keep an extra skirt in case I spill something during the day. Go fetch it for me – there is no way I'm getting my jeans back on, and I have no intention of going anywhere naked form the waist down."
"As the lady wants," he said with a bow. He took the cane with him as he went – he could keep it in his own desk, as he had a feeling he'd use it again sooner or later.
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