It was the last day of December and Emma was the only one at the office. All of her colleagues had taken the week off for the holidays, but someone had to be present, just in case of an emergency.
Emma didn’t mind, she had no plans on the days between the holidays and she’d be home in time today to celebrate the new year. She’d also earn a hefty bonus for volunteering to work this week, not that there was a lot of work to do.
Most of these lonely days at the office, Emma kept herself busy by reading a book she’d brought, watching movies on her laptop and if she did any real work, it was updating the office computers to their latest software.
Like previous years, no real emergencies occurred and by the end of the week, Emma was quite bored as she wandered through the main office room. It was a large open area shared with her colleagues. She had already spent her time cleaning up everyone’s desk, watering their plants and snooping through their belongings.
There was one place she hadn’t been yet however, her boss’ office across the hall.
Previous years her boss had often come by the office to see if anything needed to be done, but this year it seems he’d finally began to trust that Emma could handle things on her own. He hadn’t shown up once.
This had given Emma the opportunity to snoop through her boss’ office for once, but she had resisted the urge thus far. Today was the last day however, her last chance. So shortly after her lunch alone, when she could not think of anything else to do, she made her way to her boss’ office.
Just to clean a bit and water her plants, she told herself. But her main reason was to snoop around.
Her boss’ office was much smaller than the main, shared office-space. There was just a desk facing the door, some cabinets to the left and a large window on the right.
The desk was clean and mostly empty, the plants looked healthy and there seemed little to interest her.
Emma opened the drawers in the cabinets one by one, but found little of interest. She walked around the desk and sat down in the big, comfortable chair, just to feel what it’s like to sit at the boss’ desk.
On his desk was an old mug filled with pencils and pens and a short wooden ruler. Beside that stood a picture frame of her boss with his dog, a large retriever.
He was a handsome man, not much older than Emma, named James. There were no other pictures on his desk, no family photos. She believed he was still single. Emma had to admit she had a bit of a crush on him when they first met. She had forced herself to get past that however, he was her boss after all. It wasn’t appropriate to have a relationship with the man you worked for.
Still sometimes she wished things could be different. James was a good boss, confident, fair, and yet strict when necessary. He had a commanding air about him that Emma found very attractive.
Emma blushed as she sat at her boss’ desk, thinking about the various fantasies she’d had about herself with him, in this very office.
She shook her head. Fantasies were all good and well at home, but at the office she had to remain professional.
Yet she was all alone, no-one would know and no-one would be bothered if she let her mind wander a bit.
Emma imagined being called to this office, to be reprimanded for some mistake or something else that warranted a strict word from her boss. A rare occurrence in real life, but one that happened more often in her fantasies.
She grew horny and excited while imagining her boss told her she’d had plenty of warnings, it was time she paid a price for her actions.
Emma wondered how it would feel to be bent over her boss’ desk for her punishment. She stood up from the chair and blushed. The desk was right there, she could…
Filled with arousal she bent over her boss’ desk. It was just the right height, raising her bottom high with her legs slightly spread. She couldn’t believe she was doing this, but this was the most excitement she’d felt the whole week. Much more exciting than snooping through the desks of her co-workers.
Perhaps that’s why he would spank her, Emma thought. For invading their privacy. She imagined James raising her dress as she raised her own. She blushed at the thought of him seeing her cute, pink panties and bit her lip as she imagined him pulling them down to her knees as she bared her own bottom.
Bottom bared in her boss’ office, Emma spanked her own behind. The sound echoed in the small room and Emma imagined those smacks could be heard across the hall in the large office-space. She knew that room was empty, yet she blushed deeply, imagining her co-workers could hear her punishment.
After a couple dozen swats, her bottom was nicely warm and tingling. She was starting to think that she was perhaps taking things a bit too far, but at the same time she remembered the short wooden ruler her boss kept on his desk. If she wanted this to feel real, she’d need something with more reach and more sting than just her hand.
Emma grabbed the ruler from the mug and ran the cool wood across her backside. She’d gone this far, she might as well continue, she thought.
She moaned softly when the added reach of the ruler and its hard surface turned the stinging sensation in her backside into hot, glowing pain.
As the sounds of smacking her own bottom filled the small room, Emma did not hear the doors in the hallway opening, nor the footsteps of a man approaching his office.
When the doors to the office suddenly opened and James appeared in the doorway, staring in surprise at the scene in front of him, Emma squealed in shock.
Bent over her boss’ desk, one arm in the air, wielding a wooden ruler and bottom bare, red and up in the air, she froze for half a second. Then she jumped up, dropping the ruler at her feet and pulling down her dress to cover herself up.
“James.” She said, completely flustered. “I didn’t know you were coming today.”
Her boss stood frozen stiff, obviously unsure of what to say after what he had seen. He stared at her, looking her in the eyes. Emma could feel a blush creeping up on her cheeks as her boss’ eyes were locked onto her. And as she blushed, she could see a smile appearing on his face.
James put down his briefcase beside the door and took off his jacket without a word, as if he’d seen nothing. He slowly walked around his desk until he stood right behind her.
Emma stood as if frozen with her boss behind her, unable to move while she waited for his reaction. She realized her panties were still down around her knees where he could see, but she was unable to reach down and pull them back up.
She could feel, more than see, her boss crouching down and picking up the ruler she’d dropped. He placed it on the desk in front of her.
“You dropped something.” He said.
Emma blushed. “Thank you, Sir.”
“Did I interrupt something, just now?” James asked.
“No, Sir.” Emma replied.
“Really? It didn’t seem to me like you were quite finished.”
Emma blushed even deeper.
James picked up the ruler again. “Perhaps you want me to continue for you?”
Emma gasped. “What? No, why?”
“Well, you are in my office, so I am assuming it was me you were imagining swinging this ruler in the first place.” James said.
Emma bit her lip nervously, unsure what to say.
“Is that not what was happening? Then tell me, what were you doing, Emma?” Her boss’ asked.
She blushed, but she knew there was no way out of this but the truth. “What you said, Sir.”
“What did I say?”
Emma took a deep breath. “I was imagining you were swinging that ruler, Sir.”
“And why was I paddling your bare bottom, Emma?” James asked as he raised her dress, taking a peek as if he wanted to confirm to himself that her backside was indeed as red as he had seen when entering his office.
“I have been snooping through everyone’s desk while I was alone at the office.” Emma admitted, her arousal growing as she felt her boss’ eyes on her behind.
“Hmm, that’s indeed very naughty Emma, and your bottom is certainly not red enough yet to settle such a breach of office protocol.” James replied. “You should bend over my desk so we can continue where you left off when I so suddenly interrupted you.”
Emma blushed deeply. She could not believe this was really happening as she bent over her boss’ desk. She moaned softly as James ran his hands over her bare, sensitive bottom and took a deep breath when he placed the ruler on her already stinging backside.
“Ready, Emma?” James asked.
“Yes, Sir.” She replied.
He swung the ruler and landed it with a loud thwack across her behind.
Emma squealed. The full swing of his arm hurt a lot more than those flicks with her wrist she could manage herself. But before she could complain, the next swat landed across her backside and made her squeal once more.
Again and again the ruler connected with her bottom, drawing deep red strokes of burning skin on her buttocks. Emma squealed and moaned, stamping her feet on the ground and whisking her bottom left and right as she struggled to deal with the pain.
Her pretend co-workers across the hall would certainly hear these loud swats and definitely the cries that followed them. They would know she would never go snooping through their belongings again.
Emma’s bottom was on fire when James finally took a break from chastising her behind. He gently rubbed her poor backside with his hands, but even that felt painful to her sore, stinging buttocks.
“Do you often feel the need to punish yourself when you misbehave, Emma?” Her boss asked.
Emma blushed. Her bottom might be on fire, but she was still deeply aroused and James’ hands were being very intimate with her bare naked underside.
“No, maybe, I mean…” Emma hesitated. “It’s more a fantasy than a punishment.” She admitted.
“Is that so.” Her boss replied.
He smacked her bottom with his hand. It wasn’t that hard, not after the ruler, but her bottom was sore and sensitive and her boss’ hands were large and strong.
“So you fantasize about your boss punishing you, but you don’t think you really deserve it?” He asked, smacking her bottom a few more times, slowly but firm.
Emma moaned deeply. “Maybe I deserve it a little.” She admitted.
James suddenly peppered her bottom with a dozen quick and hard swats with his hand. Emma jumped and squealed, kicking her feet at the sudden increase in pain in her backside.
“I think you do deserve it, young lady.” James replied, returning to the slow, measured swats on her backside.
Emma moaned deeply, resting her body on her boss’ desk, feeling his hand spreading the sting across her bottom while the warmth of her arousal spread through her loins.
“I probably shouldn’t tell you this.” James said. “But you’re not the only one who sometimes fantasizes about things like this.”
Emma blushed. Had he done this before? To one of her co-workers? “Who?” She asked.
“Me of course.” James replied, without ever stopping the slow onslaught on her backside. “I’ve always wanted to turn one of those cute bottoms of one of you young ladies bright and red.”
Emma bit her lip, the pain in her bottom was becoming near unbearable even at this slow pace. James had fantasized about punishing her? Those few, rare occasions when he had called her into his office, had he imagined spanking her then?
“But you knew that already, didn’t you?” James said.
Emma frowned in surprise. “No, I didn’t.” She replied honestly.
Her boss paused, resting his hand on Emma’s glowing, red bottom. “Didn’t you say you snooped through everyone’s desk?”
Emma blushed. She had, but… not through her boss’ desk, only his cabinets. What would she have found if she had?
“Didn’t you find anything in the bottom drawer of my desk?” James asked.
“No, Sir.” Emma replied. “I hadn’t searched there yet.”
“Get up, have a look.”
Emma got up, without turning around so she wouldn’t have to look her boss in the eyes just yet. Her dress felt cool against her burning bottom as it slid down.
Her panties slid from her knees to her ankles as Emma crouched down and pulled open the bottom drawer. In there, on top of a stack of papers lay a large wooden paddle, made of thick wood, with rounded corners and three holes drilled through the center.
“Give it to me.” Her boss said.
Emma blushed, picking up the paddle. He wasn’t going to use that, was he? She wondered. She stood up and turned, handing her boss’ the paddle as she finally faced him again.
“I know what you’re thinking.” James said. “And no, I haven’t used this on anyone, definitely not any-one who worked for me.” He grinned. “I bought this in a whim, I saw it and I just wanted to have it. I keep it here almost to tease myself, knowing it’s just a fantasy, I could never use it.”
Emma bit her lip. That was not what she had been thinking. She wasn’t wondering whether he had used it before, she was wondering whether he was going to use it now.
“But perhaps I was wrong.” James continued. “Perhaps I can use it, now that I’ve found someone who shares these fantasies.”
Emma trembled slightly. He was going to use it! Her bottom was already sore, it was red and on fire. She wasn’t sure she could take anymore and yet, she really wanted him to use it. It had been a while since she’d felt the ruler and while his hand had been firm and strong, the slow and measured pace at which he had spanked her, had let her catch her breath just a little.
“What do you think, Emma.” Her boss said. “Do you think we were ready with your punishment?”
Emma bit her lip and shook her head.
“Then turn around and bend over so we can continue.”
Emma turned around, bending over her boss’ desk once more. She was nervous and yet excited. She didn’t know how much of a paddling she could take, but she did know how much she wanted it.
“Do you have any plans for tonight?” Her boss asked while he raised her dress to bare her bottom once more.
Emma’s mind blanked. Tonight? She was too focussed on the moment to think about anything else.
“For new-years.” James explained when she didn’t respond.
Emma blushed. She’d almost forgotten that was today, that was why they were the only ones at the office. “Nothing special.” She replied. “Just a night out with friends.”
“Hopefully somewhere you can stand.” Her boss teased while caressing her bare, red bottom. “I imagine you won’t be doing much sitting down.”
“How about you and I do our own new-years celebration. A practice count-down as it were.” He placed the cool wooden paddle against her bottom. “I’ll start at ten.”
Emma braced herself.
The paddle whooshed through the air and landed across her backside with a loud thwack. Emma squealed as her bottom bounced from the impact.
“Ten!” James called out. “Come on Emma, count down with me.”
The paddle swung through the air again and Emma squealed when it landed. “Nine!” They called out together.
“Eight!” Emma and James’ voiced echoed in the small office after the paddle landed across Emma’s poor bottom once more.
Her boss’ voice became louder with each shout, but Emma’s become softer, whimpering each word as the paddle put her bottom on fire.
“Three!” Emma’s was more a squeal than a word.
“Two!” Her buttocks danced under the impact of the paddle.
“One!” She cried as they reached the end.
One last time the paddle swung through the air as their count-down reached zero. “Happy new-year!” Her boss exclaimed as it landed firmly across her sore, red backside. All Emma could do was moan something that sounded the same.
Emma lay panting across her boss’ desk, slowly regaining her breath as the pain settled across her backside.
“You can get up now young lady, I think you’ve learned your lesson.” Her boss said.
Emma pushed herself up from his desk. She really wanted to lay down and rest for a little, but was suddenly embarrassed to lay there face-down, bottom bared in front of her boss.
She got up and turned around, blushing again as she faced James. He smiled at her, she could see his excitement and the pleasure he’d felt at punishing her.
His smile reminded her of how handsome he was and the glowing sensation in her loins reminded her of her fantasies about him. She could hardly believe all this had really happened, but the pain in her bottom was too real to be just a dream.
Emma bit her lip and looked up at her boss. “You know, there is one thing about the count-down we forgot.”
“What?” James asked.
“When you reach zero, it’s tradition that you grab the person closest to you and give them a kiss.”
Her boss smiled broadly and quickly stepped forward, grabbing Emma up in his arms and planting his lips on hers.
Emma melted in her boss’ arms, his hands on her her sore behind, his tongue in her mouth, his erection caught between their bodies. Once more she was out of breath when he let her go.
Emma then turned around again, facing his desk. She hesitated for a moment.
“What are you thinking, Emma?” James asked.
“I saw something else, in that bottom drawer.” Emma said. She bent down to pull open that drawer, not crouching this time, but bending forward, pushing her bottom against her boss’ crotch as he stood behind her, feeling his erection between her still sore buttocks. There was a box of condoms.
She grabbed the box, got up and turned around, handing them to her boss. “How about some fire-works to celebrate the new year?”
James laughed. “You’re not going to turn around and ask me for a promotion when we’re done, right?”
Emma blushed and then defiantly stuck out her tongue.
James grabbed her by the shoulders, quickly turned her around and smacked her bottom before pushing her down on his desk.
Emma moaned deeply as she lay down in the same position as when he had spanked her, waiting impatiently while her boss put on one of those condoms.
She whimpered slightly when James raised her dress and grabbed her sore, red buttocks in both hands. His cock filled her completely when he trust his hips forwards, sliding in easily as she was wet with arousal.
He fucked her hard and fast, hips smacking into her sore behind, his big cock penetrating her as deeply as it could, his hands squeezing and slapping her poor bottom.
Emma moaned and squealed. She had asked for fire-works and that was what she got: fast, hard and rough. Her legs trembled, her breathing was quick and shallow. She replayed her punishment in her mind over and over until her whole body was trembling uncontrollably in ecstasy.
James landed one last swat on her backside, his quick and sharp thrusts came to an abrupt end when he froze with a grunt, grabbing her hips with both hands, pushing his cock as deep inside of her as he could as he reached his orgasm.
They were both quiet for a moment, catching their breaths. After a while, James pulled out, turning around to clean up while Emma stood up and let her dress fall to cover her bottom. She grabbed her panties off the floor and tucked them away in her sleeve, not wanting to pull them on over her sore, sensitive backside.
James deposited the evidence of their activities together in a trash-can beneath the desk and then turned to her with a smile.
“Do you have any new-years resolutions, Emma?” He asked.
“No, not really.” She replied.
“I didn’t have any either.” Her boss replied. “But I do have one now. I’m going to be a better employer and give my employees what they need to succeed in their careers.” He smiled. “In your case, I believe that means regular and strict discipline.”
Emma bit her lip. “I’d like that, Sir.”
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