The Boss's Bucket List (WaveVelour & Dreamstreet)

[Dreamstreet]

To think it had come to this. The fact that after all the failures he had in his life, and still ended up with such a big oppotunity like this, one that was now at a massive risk, all thanks to one e-mail that he received. Working at the office of a big corporation in the center of town, and being at the top floor as the newest assistance to the big boss lady at the top. One of those jobs that only comes if you either have the quality to handle the high pressure a career lady like that can put you in, or in the case young Nicky Stone, your mother and your boss went to the same school and somehow got to the point where she would take him into her own company. It certainly seemed generous to do that for someone that young, looking like you're nurturing the next big talent of the company. However the truth was very different.

Because Nicky had never been able to keep a job for too long. Despite his enthusiasm and willingness to go the distance at each job, he always ended up in the worst possible scenario. Working in a restaurant, he would get discovered next to the chef sniffing a line of cocaine. Or when he worked at the airport loading the planes, and ended up taking the wrong luggage to the plane, because his mentor told him it was the one. It didn't take long before he got called Nicky Wrong Place, and it was quite fitting for the young man. At one point, his reputation made it almost impossible for him to land a decent job in town, and he had almost given up. Had it not been for his new boss, giving him a hard time but allowing him into working for her, he might have had to skip town all together.

At first things went as well as they could for a guy who was in a league where he wasn't at the level to keep up yet. But thanks to the way he got the job, he was given some time to get used to it, and thanks to his dedications he was getting slowly better and better. It was quickly becoming clear that he was very dedicated to doing his best and prove that his boss didn't make a wrong choice in hiring him. Every day, he hoped that he could prove himself more to her, and most of the time he succeeded at this. However his old nickname would soon come back to haunt him, as was soon in the wrong place at the wrong time.

On this day, as he was checking the e-mails and messages that was headed for the boss, he saw that he had suddenly sent him something which was titled "My Weekend Plans". At first he figured that she was actually gonna be away for a weekend for once and relax a little, but as he opened the mail to see what was inside, his eyes went wide. It showed the boss wearing a black corset and high heels, being bend over a bed and her ass being bright red with a clear handprint of either of her cheeks. His eyes went wide with surprise and he quickly slammed his computer shut. People looked at him like had just watched porn at the office, all while he looked like he had just seen a ghost.

Thinking he had to do whatever he could to save himself, he figured the best way was to take it directly to his boss and talk with her in private. While wearing his navy blue shirt that was a good first around his strong arms and toned chest and abs, along with a pair of light grey pants and navy blue shoes to match, he made his way to the top floor to hopefully get it all sorted. His hand would wave nervously over his short brown hair and his green eyes would look at the door to her office. Knocking a few times and awaiting to permission to enter, he would then slowly enter with his laptop in his arms. He would lightly bow before his boss as the door closed behind him.

"Excuse me, but... I believe you sent me an e-mail today by mistake... An e-mail that was quite, uhm... R-Revealing." He said and blushed while looking away. There was no way to say that he had just seen a picture of her almost naked and with an ass spanked until it turned completely red. All he could do was hope she would't put any blame on him.

 

[WaveVelour]

"Oh.."

When things got busy, more than they tended to be, it was usually inevitable that said busyness seeped into one's personal life. Alright, it was kinda avoidable. It just required a clear mind and undisturbed awareness. She didn't have those at the time, she supposed, sending the wrong message to a very wrong person.

"That's what happens when I spend half of my time responding to complaints about you!" Talking to herself, Lorena sank in her chair, shaking her head at the screen, having just realised she had somehow mixed up her mystery date's phone number with an employee's e-mail address. "They're not even the same thing!" No, they weren't really. But the messaging app and her e-mail happened to be in tabs next to each other. So that was the story, how she managed to send the photos of her arse to someone from the office. She didn't know whether to call him lucky, or herself incredibly unlucky.

This guy.. Just watching him stroll in carefree with the company laptop in one hand, and doing whatever with the other was stirring anxiety in her.

"I'm hoping you didn't think that you had to bring the bloody computer all the way here to show me something you have on it.." Lorena said. As bubbly as ever. Like, not at all. One after the other, her polished nails fell upon the desk. Underneath it all, her legs were firmly folded, her short skirt allowing to flaunt them well.

"Alright. Have a seat," she said, pointing to one of two guest chairs across from her. After a drawn out sigh, she continued. "You know I told your mother not to marry that guy. But she did. And they had you. And I made a promise to her years later. And you're now here." A dreadfully short story without a conclusion, which she didn't shy from reminding him over and over. This time it was kinda different. For once, it was about her mistakes rather than his.

Just like her fiery personality, her jacket was red, matching her skirt. It went well with her golden locks, striking a nice contrast. Apart from that, he wasn't supposed to see that a little red suited her in other ways.

Hacked personal files? A fabricated picture of hers being used? A virus pretending to be her? Several excuses could be found. "Yes. A mishap." Or she could just admit it, apparently. "A mistake that pains me." As if the stupidity of her brain was weighing it down, she propped her head on a hand. "I'm talking about the act of sending it to you. Not what you have.. Actually, what have you seen exactly?" Now that she thought about it, there should have been security protocols present across the systems to automatically filter stuff like that. Maybe the image didn't show at all somehow?

 

[Dreamstreet]

Just like always with Lorena, Nicky had a hard time reading his boss and her mood, even as he told her very not detailed what he had seen of her. He remained quiet while listening to her speaking, looking slightly down as she talked about his mother and how she took him in as a promise to help her out after her marriage with his dad. It made him feel for a moment that he might get fired and kicked out the company. He really didn't want that, and he felt like he had to do something in order to not get sacked.

"Well... I-I saw this..." He said as he put the laptop down on the desk and slowly opened the lid. As it opened up, it showed the picture he received, of Loraine being bend over and her ass smacked. He blushed brightly as he left it there for a few moments for his boss to inspect.

"L-Look, I'm not looking to do anything with this, I-I just wanted to make sure that you haven't sent it to anyone else but me!" He said quickly, as he was clearly already getting quite desperate to not get fired at this very moment.

"I really wanna keep this job and do my best to work for you! I-If there is anything I can do to help you out, please let me know! I'll delete the mail and everything, I just want to stay and work for you more than anything!" His voice still sounding desperate, as he looked at Lorena and hoped that she would either show him mercy or take his words as a promise that he wouldn't go further with this.

 

[WaveVelour]

Oh, there she was. Striking a pose in a corset and showing the viewer her bum, and also how easily it was marked. That self inflicted redness was supposed to raise the question, didn't it look better this way? Of course, her questions were quite different in the office. About work stuff, and deadlines, and such.

Kinda amazing how different she looked when she merely had her hair down. Well not different enough to mistake her for some other woman. Who else had a tush so nice? He didn't seem to have doubts that it might be someone else. And Lorena didn't bother to convince him otherwise either.

"Yeah, just delete it," she suggested, closing the lid. It was clearly a mistake that wasn't small, which was apparent in the photo too. Still, it could have been worse. Could have been a reply to all fiasco. And he had his heart in the right place as well, to come to her directly.

Holding her skirt down, she swiveled and got to her feet, striding across the room towards the door. "In this particular case," Lorena said, "terminating you for staring at my arse wouldn't be fair." So she wasn't standing there to show him the door. To close it rather, which improved privacy. The devil on her shoulder was whispering an idea to her as she returned to her desk. He was there to assist her. Lending a hand when she needed it.

On his side of the desk, she leaned back against it, the edge creasing the garment and digging into her supple bottom. "Alright. Nicky. What do you think about it then?" She asked, allowing him to express his remarks on the subject instead of carrying them home unspoken. "Would you have done a better job?" As if she could hear his inner voice, she answered it too. "Yes, I'm asking about it."

 

[Dreamstreet]

While Lorena moved up to close the door and make sure they were completely alone, Nicky was quickly moving over to to grab his laptop again and opened it, as he seemed to take her order to heart about deleting the photo she had sent. Thanks to his nervousness and fiddly fingers, he did spend quite a bit of time just opening the lid and soon the image was on display again. Seeing it again, even though he had already gotten the image burnt into his mind, he blushed a little as he was just about to delete it, when he heard her question behind him.

It caught him off guard, and as he turned to look at her, he seemed confused like he had just been asked to do a complicated math equation. Just as his lips were about to ask her what she meant, she basically answered it for him, leaving his mouth open for a few moments. Was this some kind of test? Was she asking to see if he would do that to her? Of course he wouldn't... Unless she asked him to. He was looking at her again, as if waiting to see if she meant it as a joke, but she just kept up her unphased gaze on him. It made him feel that she was asked him a serious question, and wanted a serious answer.

"I mean... I..." He looked at her again, then back at the laptop, as if he was studying the redness of her ass, to see how much she would have been spanked to look like that. "I-I've never done something like this but... But if my boss wants me to do it... I think I could do it just as well, and I would do my best to do it even better!" He said as if trying to sound confident at the end, but also to convince himself that this was the truth.

Even as he looked up at his boss, wondering if he answered her correctly, he couldn't help but imagine doing just that. Using his own hands to smack her ass until it would show his fingers on her soft skin. The thought alone made him gulp a little, as he waited for what she would do next.

 

[WaveVelour]

The laptop she'd just closed had been opened again. Most likely to check that questionable photo one more time. She was about to scold him for that. Hm. Though she'd also told him to delete that email, hadn't she? Yeah.. That was probably what he was doing. Well she was admittedly a bit biased. She didn't hate him, but she also couldn't help being stern with him. That was also his mother's wish. 'Lena. Whip him into shape.' Something like that.

Now that she thought about it, maybe this wasn't quite a brilliant idea. After all, her dear friend didn't send him to her for this. But then again, it wasn't a big deal. It could even give him a little boost of confidence? Which was never bad. Well, that might help him overcome this ridiculous mindset of his? Being this extremely unlucky young man whose fate bound him to be always in the wrong place? No. Lorena didn't see the irony, that it had just happened again. Kinda.

"I'm listening." She tapped her foot once, not really knowing what kind of thought process he must be going through.

Haven't done it before? Haven't done what? Smacked a lady's bum? Maybe it wasn't as hard to believe. "Don't worry, I'm rather used to it," she said. A claim that didn't lack proof.

For a moment, Lorena thought he was gonna stand straight at attention and salute. That little promise of doing the best and all. Well enthusiasm didn't hurt. "Right.." she simply said in return. Rather calmly as opposed to his anxious exclamation. "Alright." A slender finger flicked up and down then, telling him to lift his arse. She herself pivoted to face the desk between the two comfy guest chairs. Gingerly, Lorena bent over, propping herself on two arms. Her skirt inevitably ran up. Which may or may not be high enough to show the reinforced part of her tights. It was the reason her legs had a soft sheen to them. Other than that, they were seamless. Sheer, so not really hiding the black thong underneath. It was rather covered by her..

"Skirt, up." Lorena ordered again. "Tell me what you see." Perception and articulation. Any good boss had to test those abilities in her employees after all.

 

[Dreamstreet]

At first, Nicky's eyes were following the weird movements of Lorena around her now closed off office, until he saw how she waved her finger at him. In an instant, he got up from his seat and stood up like he was ready to execute some kind of command. However instead, his eyes just followed her again, as she moved over to bend over the table and letting her skirt slide up along her long, slender legs. His eyes went wide as he saw more of her being revealed.

Despite her skirt not showing off her ass completely, it was still a wonderful sight to behold already for him. It made him take a few more moments before recognizing that she asked him to lift the rest of it up. Quickly he moved over to her and got a hold of the sides of the bottom of her skirt and gently lifted it up over her hips, until her butt was then fully on display. Even with the tights and the black thong in the way, it left very little to his imagination, which was already running wild.

"I see... I see..." He closed his eyes and took a deep breath in order to gather himself and calm down a little. Letting out a sigh, he looked at her again from behind and finally spoke up. "I see, a pair of long beautiful legs that looks so good in those tights. But not as good as your round ass does! Even though I can see it through your tights, it makes me think of how much better it would look without them on." He said and his hands were twitching a little in anticipation of how she would react. His heart was beating fast, and even though his words were direct and honest, he still hoped that they were what his boss wanted to hear.

 

[WaveVelour]

Not quite a womanizer, was he? She'd go ahead and guess that he wasn't particularly good with women. Or maybe he was just anxious because she was, well, who she was. Well it wasn't a bad thing that he knew his place. Right now, that was apparently behind her bent hips. Not exactly the same perhaps, but the position was quite similar to the photo. Head low and bum high. Although she was more properly dressed this time, as in she didn't wear only a lace up corset, it ought to be more exciting than staring at a photo.

Her tight skirt clung closer to her hips, playing along with them. It was short enough to stir certain feelings in its audience. What was the expression? The pencil skirt, deadlier than the sword? As he proceeded, she could feel the hem brushing up her bottom. She wouldn't call it unceremonious either, as Nicky took his time inching the garment more and more.

Alright. There it was then. The boss' bum. A stark contrast to how she was known, stern and sharp. Not from this angle, as it highlighted features with opposite traits. Beautiful, round, just good all around. His words, not hers. "Oh, is that so?" Though she wouldn't argue either.

"Yes," Lorena said. Clear and sharp. "I expect you to pull them down." Not that they provided her with any meaningful protection, but it just sounded more satisfying when she was truly in the flesh and when smacks would eventually begin to rain down. "And don't expect you to stop at my tights either," the woman added. "While at it, allow me to have a good first impression of your handiness too."

 

[Dreamstreet]

The response he got from Lorena was actually making Nicky smile. Finally he felt like he was going something right and to her liking, and all he had to do was be honest with her. This felt good, to think that he was finally doing something well, and something this exciting. It made him instantly think that he wanted to do anything that his boss would ask of him, which of course included the next order she gave him.

The first part of it was very obvious, pull down her tights and her thong, which he quickly moved over and was ready to do.However her request to show a good impression did make him look a little confused for a few moments. Did she want to feel his hands on her body more? To be more touching rather than elegant with taking off her outfit? He knew better now than to ask questions about it. For now, he tried again with what he felt was correct.

As he moved in behind her, her let his fingers slip into the hem of her tights and slid his fingers further down along her soft legs in order to slowly pull down the tights. His hands would push a bit into her skin to make sure he wouldn't tip her tights, but still making them get pulled down slowly. It showed that there quite a bit of strength underneath his shirt and pants that he was ready to use. Thanks to how careful he was, along with the fact that he also took his time, he soon had the tights down by her feet, waiting for her to step out of them so he could put them aside.

Then as he got up and looked at her almost naked butt, he unconsciously licked his lips for a short moment, before he reached forward for her black thong. He would put his hands on her thighs, before moving them up to grab the sides of her thong and hooking his fingers into the hems. "May I say, Miss Lorena... That this is one of the best and most beautiful things I've ever seen in my life?" He said while his eyes were still locked with her ass, while he slowly slid off her thong, removing the last line of defense that also weren't there on the picture. Only big difference now, was the kind of spanking she had taken in the picture compared to now, but Nicky hoped that he might just get a chance to copy that photo himself.

 

[WaveVelour]

It must've been an interesting working day for him. Well the same could be said about her too, she supposed. After all, it wasn't often she let a subordinate lift her skirt. And by not often, she meant never. Flirty skirts and cleavages. The officefolk never got to explore what those teased. Nothing more beyond a few fleeting glances. As the PA though, Nicky's job description involved personal matters too. And things were indeed getting personal. And private.

Staying still over her desk, she let him work. A simple task that involved some delicate parts. Her nylon-clad backside was probably a decent tease for him. Well, the overly careful manner he undressed her was teasing her right back though, which she hadn't thought about frankly.

"Showcasing your diligence, huh?" Lorena asked as he gingerly pulled her tights down. Once the waistband slid past the underside of her cheeks, her bottom was freed. Naturally, the lift offered by the garment was undone too, subtly causing her hips to widen and her buttocks to settle into a more natural shape.

Another waistband. Black this time. It needed to go down too. And it did. Also slowly, admittedly encouraging a bite on her bottom lip. The act rendered Lorena totally bare, leaving nothing unexposed below the waist. Well she'd already sent him a picture of how things looked. But this was obviously way more intense.

"W-well." She cleared her throat. "Seems like you've discovered the eighth wonder of the world." Well he made it sound like that. And Lorena was happy to go along with the praise, a weakness of hers really.

"Now about your handiness.." Now that the package was unwrapped, they could finally go with the plan. "Hand on my bum," Lorena ordered, elaborating on what she wanted. It would probably come off as just putting his hands on it, and not exactly slapping it. So she figured she should rephrase it to be more clear. Though she wasn't in a hurry to do so.

"I mean," she eventually said after a strategic pause. "Give it a swing."

 

[Dreamstreet]

Just as the panties slipped fully off of Lerona's legs, Nicky couldn't help himself but to step back and watched the wonder in front of him. She was bent over so perfectly, her soft and long legs were looking so hot while her sexy round butt just took center attention. No wonder she could get someone to smack it until it would turn red. What kind of man would refuse a request like that?

Those thoughts did go through his head, just as the boss gave her next order. Just like earlier, she would emphasize exactly what she meant before he could ask her about it. His heart went up into his throat. This was really happening! He was going to smack her ass, that big sexy booty of his boss that he had just undressed. "U-Understood, Boss!" He said as the only thing he could truly come up with, before moving over to stand just behind her. Taking a small step sideways to the left, he raised his right hand, opened his palm and looked the place where he wants to hit her.

He raised his hand and let it stay there for a few moments. Not that he was hesitating to smack her ass. There was nothing he wanted more in the world at this moment, than to spank his hot boss. But he wanted to see if she were just teasing and pulling out of this. However it seemed that wasn't the case. This was his chance, possibly his one and only chance to smack the best looking ass in the office, and he wasn't going to miss out on it.

Holding his breath, he swung his right hand down towards her bum, letting his palm connect firmly with her left cheek. It was with enough force that it started to wobble and jiggle from the impact, which only made it look even hotter. His hand would stay on her ass for a few more seconds, before he would slowly pull it away, as if to see if he was going to leave a mark like there was in the photo. An optimistic wish from the young assistant.

 

[WaveVelour]

Mhm. It was in a most ideal position to give it a slap or two, her bottom. It could have very well been more difficult not to go for it at this point. The sheer willpower required to pass the opportunity to beat that arse a little? Yea, it must have been anything but great. At the top of the corporate food chain, yet also a round bottom over the desk, deserving a lil punishment like everyone did on occasion. Yes, Lorena never said it was supposed to feel like a punishment, but she had told him to do a good job at it.

"That's right. Enjoy the view," the blonde manager called out when he took some time stargazing. Not really feeling the need to look back to confirm. After all, where else would he be looking at when she was there poorly covered? "Don't keep me waiting though," she also suggested. Well, everyone knew how much she dreaded tardiness.

It ought to be his first time swatting his boss on the tush. She however had experienced the thrill of being spanked as the head of a company before. In this regard, she was more experienced receiving than him giving. Well it was still exciting for her, regardless how much of it she let on.

Then his hand rose finally. And it came down quickly. Not bad for the first try. And spot on if the target was the east side. It only took one proper smack to break the illusion of total firmness. Right globe more than the other, Lorena's administrative bottom wobbled. She slowly blinked, enjoying this familiar sensation.

"Hm. Up to a good start," she admitted, just when her sting-yearning bottom stopped shaking. Though she didn't expect it to be awfully stationary during the upcoming moments. Start was the keyword here. Surely, she didn't go through the trouble of showing her bare rump to him just to receive a single good smack. She needed more of course. Did she deserve more though? Surely, his inner voice was telling him something about that.

"What about the other side?" she asked then.