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Zoe was devastated when she lost her job due to Covid from the local factory, where she had worked as an office secretary since leaving high college. It was all she’d known for the last 9 years, and now she found herself just turned 27, unemployed with no savings and a sizeable credit card bill to unforseen medical bills.

After a fruitless morning at the unemployment office, she was walking dejectedly back through town towards her car. When in the window of one of the more famous bars, she saw a poster advertising for bar staff. Zoe couldn’t believe her luck. She often frequented the bar in the evenings, and getting a job there would be the coolest thing ever!

After a short interview with the bar manager called Dave, where Zoe lied about her bar experience, she was offered the job, starting that coming Saturday. Zoe was thrilled and spent the rest of the afternoon on Facebook bragging to her friends about her new job.

Zoe had a great time on Saturday and seemed to be a natural behind the bar. Over the following weeks, she became a feature at the bar, well liked by customers and staff alike. Each month, the bar had a theme night and last months ‘superheroes’ night had been a gigantic success. With that in mind, Dave put up posters advertising the next theme night – ‘Teachers and schoolgirls’ – hoping to attract a younger crowd from the nearby school.

Zoe was still very short of money and couldn’t afford to order a costume for the night, but she did remember she still had her old black pleated college skirt somewhere in her wardrobe. It was a little on the short side as she’d grown considerably since leaving college, but this combined with a pair of black stockings and suspenders and a white shirt gave her a very sexy catholic college girl look.

The bar was packed that evening with everybody getting into the spirit of the night with several girls wearing skirts much shorter than Zoe’s. The guys working seemed to be wearing “normal teacher’s clothing.” Dave was wearing a principal outfit in a very authoritarian manner.

At about 10pm, when the bar was at it’s busiest Zoe was pouring a glass of lager when the keg ran out. She called over to Dave, who normally changed them, but he was busy with a big round, and he asked her to change it herself. Zoe had never done this herself but she had watched Dave do it several times and was sure she knew what to do. The bar ‘cellar’ was actually just a room behind the bar stacked with bottles, kegs, and other bar supplies. Zoe managed to disconnect the empty keg but something seemed to go wrong with the new one and as she started to connect it lager started spraying out everywhere. She screamed in dismay and tried to stop the flow with her hands but all this did was direct the liquid all over her. Dave came rushing in to see what the commotion was and immediately saw what the issue was, Zoe hadn’t turned off one of the valves. He quickly shut the valve and the lager stopped spraying out, but by now, Zoe was drenched and there was almost half a keg wasted on the floor. He checked to see if she was okay, to which Zoe said yes. He then properly connected the keg and told her to return to the bar and finish her shift and that he would talk to her later.

Zoe was embarrassed to return to the bar as she was dripping wet and her white shirt now clearly showed her black bra underneath. However, none of the customers seemed to mind, in fact some wondered that she had deliberately wet her shirt as part of the evenings fun!

It was well after midnight before the bar had finally emptied and all the staff had gone home. Only Zoe and Dave remained doing some final cleaning. When that was done Dave called Zoe into his office at the back of the bar.

Zoe followed him to the office and noticed that on the way Dave had picked up his wooden ruler and was swishing it in front of him. Once in the office Dave sat behind his desk, and began bending the ruler in his hands as if it were some stress relieving toy. He then asked Zoe what had gone wrong with the changing of the keg earlier in the evening. Zoe halting fumbled through a made up excuse about being a different sort of valve to what she was used to. Dave sat impassively while Zoe tried to explain herself. At the end Dave simply told her that she was lying, and that all kegs had the same fittings. He went on to say that it was now obvious that she had lied during her interview about her bar experience and that she was fired! He also told her that she would not be getting any pay this week to cover for the lost lager.

Zoe immediately broken down in tears begging Dave not to fire her and to give her another chance. Dave stood firm and told her to leave immediately. Zoe was desperate to keep her job and asked if Dave could punish her in some way instead of giving her the boot? Dave looked her up and down and asked her what she had in mind?

Zoe wasn’t quite sure herself what she meant, but thinking fast she said that if she were at college now and had been caught lying she would probably get the ruler…

They both knew this was false, as this punishment had been abolished long ago in even private schools, but Zoe had to try and discover a way to convince Dave to keep her on. Maybe the principal and schoolgirl theme together with the fact Dave kept flexing that ruler in his hands had given her the idea.

Dave seemed to consider this offer for a few moment before confirming with Zoe that she was offering to take a thrashing from him in return for keeping her job. Zoe nodded her head enthusiastically, seeing that Dave seemed to be seriously considering her proposal. After all she wondered to herself, how painful can a few quick strokes of the ruler really be?

Dave finally nodded his agreement, telling her that she would get six strokes for lying and six strokes for the lost lager. All of which would be given on her bare bottom. At this Zoe swallowed hard. She had only wondered it would be a couple of strokes over her skirt. Now she wasn’t quite so sure it was such a good deal after all, but what was the alternative?

Dave cleared some paperwork from his desk and told Zoe to bend over and hold onto the other side. As she did so she realised what a revelling position this put her in as her skirt had already risen up showing the flesh between her underwear and her stocking tops. The high heeled shoes she was wearing pushed her bottom up invitingly toward Dave who had by this time walked around his desk to stand behind Zoe.

What a sight she looked, bent over the desk with her skirt rising up and long slender legs encased in taught black nylon. Dave couldn’t believe his luck. He’d been trying to think of a way to have this girl ever since he employed her. In fact that was the main reason he had employed her in the first instance. Her youthful figure and perky breasts were a very strong attraction. Now it was time for him to enjoy himself. He stepped forward and flipped Zoe’s skirt up onto her back revealing fully for the first time her skimpy black lace underwear. They were stretched tightly across her bottom and framed by her suspenders and garter belt. Dave paused to admire the sight before him and he noticed her legs were trembling slightly. He caressed her bottom and thighs allowing his fingers to linger between her legs before slowly dropping her underwear to just above her knees. He then stood back and picked up the ruler.

And so it begins…

The first stroke landed with a solid *thwack* right in the center of Zoe’s ass. Zoe yelped and couldn’t believe that such a simple piece of wood could cause such pain!

Dave stood back admiring the first red strip and then asked Zoe if she currently had a boyfriend? Zoe seemed a little confused at first, not quite understanding why Dave was asking her questions now in the middle of a caning, but she said yes and his name was Tom.

The second stroke swished in quickly landing just below the first and just as hard. This time Dave asked Zoe if Tom had fucked her yet? Again, Zoe wasn’t quite sure where Dave was going with this, but she answered, yes. This prompted the third hard stroke and the third question, when had she last been fucked?

Zoe was now starting to get the hang of this, realising that Dave was getting turned on by caning her and asking her such intimate questions at the same time. So she told Dave she had been fucked twice last night by Tom at his apartment.

The fourth stroke landed much lower, just on the crease between her thighs and bottom. This time Dave asked her if she had taken Tom in her mouth? Zoe recounted one of her first dates with Tom when she had sucked him off in his car.

The fifth stroke was back to the center of her bottom, landing just above the first stroke. Dave couldn’t believe how submissive Zoe had seem to become during the caning and the way in which she was answering his questions. This time he asked her if Tom was well hung, he wanted to get a mental picture of these two fucking. By now Zoe had got into the swing of this, and despite the burning pain in her bottom from the cane she was enjoying telling Dave about her sex life with Tom. She proudly told Dave that Tom was quite big and that she often struggled to accommodate him!

Dave whipped the sixth stroke down hard, cutting diagonally across the first five, muttering bitch under his breath as the ruler landed. Zoe cried out in pain as this stroke was much harder than the others, and as she stamped her feet on the floor to try and blot out the pain her panties gradually slipped down her legs around her ankles. Dave then asked if Tom had ever tried anal with her? Zoe remained quiet at this question, not sure how to answer. Dave smacked her bum with his hand, asking the question again. This time, Zoe quietly answered that they had tried, but Tom was too big and that she couldn’t take him.

Dave seemed happy with this answer, and he moved forward to examine Zoe’s bottom which was clearly marked with six strong violet welts. Not wanting any repercussions, Dave realised that Zoe couldn’t probably take another six with the ruler tonight, but none the less he still had further plans for her.

So he then told her to stand up and take off her skirt and shirt. Zoe slowly got up from the desk and picked up her panties from the floor before carefully undressing as she’d been told, folding her clothes and placing them on the desk. She then stood before Dave in just her skimpy black bra, stockings and suspenders. He took a step back to admire the girl before him, still flexing the ruler in his hands. Zoe nervously looked down at her feet, not quite knowing what was gonna happen next. Dave then reminded her she still had six more strokes to come and that these would be much harder. Zoe asked Dave if there was some other way she could pay for her mistakes this evening, noticing the tent in his trousers. Dave smiled to himself, he had hoped that the threat of six more harder strokes would give Zoe something to think about. So he then asked her exactly what she meant? As before Zoe hesitatingly suggested that Dave might want to trade the last six for a quick fuck. Even before the words were out of her mouth Zoe couldn’t believe she was offering herself to this man – and all just to keep her job!

And again, as before, Dave confirmed exactly with Zoe what it was she was proposing before pretending to be considering her proposal. Although this was exactly what he’d hoped for. After what seemed an age to Zoe, Dave finally agreed and put down the cheap piece of wood, telling her to bend back over the desk.

She could hear him undoing his pants behind her, and then the unmistakable sound of a condom being unwrapped. She then felt himself positioning himself between her legs and then slowly rubbing himself up and down her crack. Dave then told her to hold on tight as she was in for a bumpy ride, and without further ado he plunged himself straight into her. Zoe gasped as she felt Dave’s hard cock spread her, he certainly was big and despite her boasts about Tom’s size, Dave was much larger and he really seemed to know how to fuck. She felt her self being stretched more than she’d ever been before, but despite this she also felt herself responding to this relentless pounding.

Dave was holding Zoe by the hips as he thrust into her as hard as he could but after several minutes he slowed his pace before pulling out and telling Zoe to turn around and lay back over the desk. As Zoe stood up to get into this new position Dave quickly reached around and undid her bra letting it fall to the floor. He then buried his face in her breasts, nipping with his teeth causing Zoe to gasp. Dave then pushed Zoe onto her back on the desk, then taking hold of her legs in his arms so that she was totally wide open and forced himself back inside her again. He fucked her with long hard measured strokes, each thrust making her breast wobble and Zoe moan. Dave knew he wouldn’t last much longer, the sight of this 27 year old beneath him struggling to take his gigantic member, combined with the vivid strike marks on her bottom and upper thighs was enough to push him over the edge and he came with an animal roar, pumping load after load of cum into the condom.

Dave pulled out of Zoe and carefully unrolled the full condom, he then up ended it and squeezed all the cum out onto her face dropping gigantic globs into her mouth, eyes and hair. Zoe tried to twist away but it just had the effect of spreading the cum all over her face. Satisfied, Dave zipped himself back up and stepped back from the girl laying on his desk, her legs still wide aside and her face glistening with cum. It was a sight to behold, there were little bit marks on her breasts and as she stood up from the desk and turned around Dave could once again see the marks of his ruler on her ass.

Despite his earlier agreement that Zoe should be let off the final six strokes he was very tempted to change his mind and complete the punishment there and then. However, Zoe was struggling back into her panties and putting her bra back on whilst looking for a tissue to wipe her face clean. Once she was back in her underwear she started to look for her skirt and blouse. But Dave picked up the ruler and began flexing it between his hands telling Zoe to stop what she was doing as she had another six to come! Zoe just stared at Dave, she couldn’t believe that after all that he was seriously gonna cane her some more?

Finally, she said that she wondered they had a deal, no more caning if she’d let him fuck her. Dave just said to her coldly that he’d changed his mind, but given the time he would complete the punishment next weekend. Begrudgingly Zoe agreed and quick grabbed her clothes and left Dave’s office…

NSFW: yes

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