A Book for a Bookkeeper Ch. 02

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A shopping trip with his boss and a date with his neighbour.
7.4k words
4.66
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Part 2 of the 2 part series

Updated 06/10/2023
Created 08/09/2020
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kVia
kVia
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"Put on the sluttiest outfit you've got. We're going shopping and I want everyone who sees you to know you're my whore."

It had just been a day since Oscar had used a magical book that had come into his position to take control of his bitchy boss, Nicola. He'd already gotten used to controlling her body and mind. He'd enjoyed the feeling of humiliating her and using her.

Oscar was still lying in bed while he watched a naked Nicola go to her closet and begin rifling through her clothes. She emerged with a very sheer, pale blue, spaghetti-strapped tank top that looked like it would barely cover her tits. Nicola was also holding a plain black skirt that, like the top, wouldn't cover much beyond the bare minimum.

"Please, Oscar, I never wear this stuff. Don't make me," Nicola pleaded.

"Put them on. No bra and a thong," replied Oscar.

Nicola had pulled out a tiny black thong and was pulling it up her legs, It disappeared into the crack of her ass. Oscar could see that her pussy was only just being contained by the strip of fabric. Once it was in place, Nicola stepped into the skirt and completed dressing herself in her barely appropriate outfit. Oscar found it strangely arousing watching the naked women cover herself up. When the top was in place, Oscar was quite happy to see that her nipples could be made out through the fabric. He could sense the embarrassment she was feeling.

They pulled into the car park of the local mall in Oscar's car. He was buzzing with excitement at parading his boss around in public. He took a good look at Nicola as they walked to the mall entrance. From behind, all of her lower back was exposed and the black skirt was tight on her ass but showed off almost all of her smooth, tanned legs. Her top looked like the most narrow strip of fabric that would cover her tits.

Oscar was planning on having Nicola buy some lingerie and some more revealing clothes that he could have her wear around the office from next week. He had another few stops in mind as well. There was a sex shop in the mall. He was looking forward to making Nicola buy some toys and things there. The other stop he had planned was a tattoo and piercing shop. He had always liked the look of pierced nipples and decided that Nicola would get that done.

As soon as they stepped inside the mall, Nicola had begun attracting looks from almost everyone that walked past. Men and boys walking past would let their gazes linger on Nicola's chest, tummy and legs. Oscar could see in Nicola's mind that she wasn't enjoying the experience. He mentally directed her to start walking to the high-class lingerie shop, Whispers. Oscar had never had a reason to shop there but had walked past it regularly. People continued to stare as they walked on.

"All these people are checking you out. You know I could make you beg to fuck one of them? And I bet anyone we picked would do it, given what you look like," said Oscar as they spoke.

He continued, "It's going to turn you on. Whenever someone checks out your tits or ass, you're going to get a bit aroused." Oscar sent a wave of arousal through Nicola as he gave the instruction.

They arrived at Whispers and Oscar directed her and followed her in. There was no-one in the shop except for a young girl moving bras onto a rack. She turned and smiled at the two people that had entered the shop. Her eyes widened as she looked over Nicola.

"Umm... Hello. Can I help you or I can let you have a look around?"

Oscar quickly sent what he wanted Nicola to say into her mind.

"I'm a dirty girl and I want to get some slutty things to make him happy." Nicola gestured to Oscar as she spoke.

The shop assistant was taken aback.

"Well, umm, feel free to have a look around and let me know if I can help you find anything."

Oscar finally spoke, "Thanks for your help." He then directed Nicola to take a quick look around and select a few things that she would be embarrassed to wear to work. While she was selecting the skimpiest items she could find, Oscar had found a wall of items that were clearly designed to be only worn to seduce. One leapt out to him. It was a bright pink fishnet bodysuit. The size of the gaps in the fishnet made it obvious that nothing would be hidden. Oscar took it off the hook.

He went over to Nicola who had a mass of frilly and lacy material. He deposited the fishnet item into her collection. He was standing directly behind her as she faced the wall of lingerie and he moved as close as he could and his chest was against her back and his crotch was against her ass. He reached around her with his left hand and grabbed her boob and gave it a squeeze. As he groped her, he leaned over her shoulder so his lips were at her ear.

"I look forward to having you parade around in these. Maybe you'll do it in your office and some of the guys at work can watch the show."

As he'd done when they entered the mall, he pushed a feeling of arousal onto Nicola. He could feel she was getting turned on. Oscar was also feeling it. His dick gave a twitch and tightened the front of his pants against her ass. He decided it was time to move on.

"Go and pay for that stuff," Oscar told her.

Oscar and Nicola left Whispers and went back out into the mall. Nicola immediately had a bunch of pairs of eyes on her. Oscar felt the feelings of embarrassment and arousal she was feeling. He mentally started her walking towards the sex shop, Erotic Dreamz.

They had just reached the shop and Oscar was ready to guide Nicola in and have Nicola spend more of her own money on butt plugs, beads and other toys for him to use. Oscar saw in Nicola's mind that she had seen someone she knew. Focussing in, he read in her mind that the woman walking towards them was called Danni and Nicola had known her since uni. They were often at the same parties and were always competitive and catty with each other. Oscar looked up and saw a beautiful brunette. She was wearing ripped skinny jeans that showed off her long, sleek legs and pink long sleeve sweater with the sleeves pushed up to her elbows. She was tall and slim. Her hair was a straight short bob that came to just below her ears.

Oscar sensed that Nicola wanted to sink into the floor and disappear. She'd do anything to not be seen by Danni. Oscar pushed an action into her brain and Nicola felt her arm moving up into a wave out of her control.

"Danni! Hi!" She heard herself call out. Danni looked up responding to the call. Her reaction was immediate when she realised she was looking at her friend Nicola, dressed like a prostitute, with a guy she didn't know standing with her. She came over.

"Hi Nicola," Danni said, "That's a wild outfit. Bold." Danni smiled.

Oscar continued controlling what Nicola was saying, "Yeah, This is Oscar. We work together. Oscar, this is Danni."

Oscar spoke up, "Hi. Nicola likes dressing up like this for me." He turned to Nicola, "Don't you?"

Oscar prompted her reply and ratcheted up the arousal she was feeling from having people check her out, "Yes. Feels so good dressing up for him."

Oscar could see on Danni's face she was uncomfortable by this abnormal conversation she was having. He decided to embarrass Nicola as much as he could before they left. He looked Danni in the eye and as he did, he reached out and placed his hand on Nicola's ass and gave it a squeeze, making sure that Danni could see enough to know it was going on.

"We'd better get going," he said to Danni. "We're heading in here. Nicola is going to buy a whole bunch of sex toys for me to use on her. It was nice to meet you, Danni."

He had Nicola speak, "He's right. I'm thinking of getting a buttplug for him to put in me. We should definitely catch up soon though." Oscar had Nicola flash a smile at her friend.

Danni stared stunned, "Ummm, wow, yeah, Bye."

Oscar and Nicola stepped into the shop leaving Danni reeling. It was a reasonably sized store with a number of aisles and even a curtained off section that Oscar suspected kept the most x-rated material out of view of the more fun, jokey items. It was more dimly lit than other shops. There was a skinny, young, white guy at an elevated counter staring at his computer screen bored. He had really long hair that was pulled into a loose ponytail that ran down his back. There were no other customers in the shop. He looked up and noticeably held his view of Nicola for a few moments before turning back to his computer without saying anything.

They slowly walked down a random aisle. Oscar could tell Nicola was totally ashamed at what had just happened. He relished her feeling that way. He could see her thoughts flashing quickly through her brain. He mentally allowed her to speak but made sure she'd speak quietly so that no-one would hear her.

Her words came flooding out, "You asshole! You goddamn prick! Making me talk like that to Danni while I'm dressed like a fucking whore. She's definitely going to tell all my friends."

She had real venom in her voice but it was coming out only a little louder than a whisper.

She continued, "I can't believe you did that. Fuck you."

Oscar was unfazed by her outburst.

"Let's just consider it payback for all those evenings of overtime you made me do. And now I'm going to need to punish you for this little tirade. You should know better than to use that sort of language with me. So this is how it's going to go. I'm going to give you a shopping list of things to get here. I'm going to peruse the magazines. Once you've gotten everything, you'll check out and ask the guy there if there's an office or bathroom that we can use to try some of the things. If he doesn't let you, you'll flash him your tits to try and convince him. Ready for the list?"

"No, Oscar. Don't make me do this. I'm sorry," begged Nicola.

"That's better, but just a little bit late. So here's the list: a slutty french maid outfit, a vibrator, get something that looks like it's got some kick to it, anal beads, some nipple clamps, handcuffs, the biggest buttplug you think you can take, and a paddle or something to spank you with. It seems like you might need more punishments in the future. I'll be over there when you're ready." Oscar pointed at a rack of porn magazines.

Nicola began to turn compelled to follow Oscar's request.

"Give me a kiss and say thank you," Oscar commanded. Nicola turned back and craned up to kiss him. As her lips made contact with his, Oscar grabbed her ass as he'd done outside the shop in front of Danni. Her skirt was so short that Oscar's fingers made contact with Nicola's bare skin on the back of her thighs. He loved the thrill of what she felt whenever he did it.

Nicola broke the kiss. "Thank you." There was scorn running through her brain that Oscar could feel.

Oscar walked over to a wall of porn and idly picked up a magazine. His focus was not on the pages of naked women though. He was paying close attention to Nicola as she went around the shot. She had found the vibrators and had quickly selected one. It was called The Rumbler and the packaging emphasized how intense it was. It has a secondary protrusion coming out of the side for clit stimulation. Nicola selected it.

Nicola moved on to the wall of butt plugs. Oscar was reading her thoughts from across the shop as she looked over the choices. His instructions had been for the biggest one that would fit inside her ass. She dismissed all of the smaller ones. A large metal one caught her eye and she picked it up. It was labelled The Professional. Oscar was in her brain as she weighed up whether she thought she could take the large plug in her ass. She added it to the vibrator.

The rest of the items on the shopping list that Oscar had given Nicola were slowly added as Nicola went around the shop. She had an armful of toys and equipment as she found a french maid outfit. The store only had one and it was cheap and looked incredibly slutty. It was added to the pile. Nicola mentally prepared herself as she headed for the counter where the shop assistant was still barely aware that there were people in his shop.

As he finished scanning the last item and Nicola handed over her credit card, she asked, "Hey. This is a weird question but is there somewhere private that me and him could go once we've bought all this stuff?"

The assistant responded in a deep voice, "There's a breakroom through the back. But customers aren't really allowed back there."

Nicola's heart sank as she knew what was coming next. She felt herself open her mouth, "How about this - would you let us back there if I show you my tits?"

The assistant had finished the transaction and his eyes went to Nicola's tits as soon as she suggested it. Oscar had put his magazine back on the rack and was watching his mental commands to Nicola unfold.

"Okay."

As soon as the word was out of his mouth, Nicola pulled the bottom of her top over her tits and let it sit across her chest. Her large boobs sat out prominently and her nipples were firm from the horniness that Oscar was making her feel. The shop assistant was taking in the sight of the perfect tits.

Nicola took the bag that had been filled with her purchases and with her other hand tugged her top back down over her tits and then turned and headed to the door at the back of the shop. Oscar joined her as she reached the door.

The break room was pretty bare. A brown 2-seater couch pointed at a TV and a small fridge with a table and a single chair. The door had a bolt and Oscar locked it and then faced Nicola.

"You were pretty rude to me out there," he said. "Now that we've got the tools, I can give you your proper punishment. Before we start though, I'm going to let you speak your mind again. It'll be nice to see if your attitude has improved or if you need a bigger punishment than I have planned."

Oscar could read Nicola's mind and she wanted to tear into him again but she calculated that would make her situation worse.

"I'm sorry for before, Oscar."

"Thanks for the apology. You do still need to be punished though. Before we start though, I'd like to hear you say three nice things about me." Oscar thought this would torture her a little. He knew she wanted to unload expletives on him but she'd have to lie to prevent the punishment from being more severe.

"Okay. Well... You're a good worker. And I don't want to say it, but you've got a big cock. And, ummm..."

Nicola had paused for a while.

"Too slow, slut. Oh well. Let's carry on. I think we'll start with a blowjob while I look over your purchases."

Oscar sat down on the couch and patted the seat next to himself. He mentally commanded Nicola to take a kneeling position on the couch so she could lean over and suck his cock. As she climbed into position, she handed Oscar the bag of sex toys she'd just purchased.

Oscar pulled his pants and underwear down and revealed his semi which was already an impressive size. As he did, Nicola was kneeling sideways on the seat to the left of Oscar with her ass on her ankles. She reached and grabbed the base of his cock with both hands to take the head of it into her mouth.

As Nicola began sucking, Oscar stroked from the top of her spine, down her back, over the swell of her ass, and grabbed the hem of her small skirt. He pulled it over her ass cheeks and revealed her tiny g-string underneath and the entirety of her ass. He then stroked and groped her ass cheeks. It was something for him to play with while she sucked his cock and pumped the base with her hands.

The blowjob continued with Nicola getting more enthusiastic with a mental commande from Oscar. He took his hands off her and began rifling through the bag. He took a look at the nipple clamps and handcuffs and thought about how fun it would be to restrain her and tightly pinch her nipples and pull on them while he fucked her. He felt his cock twitch in her mouth at the thought.

He pulled out the butt plug, The Professional. It seemed big. The packaging suggested generously lubing it up before use. Oscar realised he'd left lube off the shopping list. It was an oversight but he intended to carry on and thought the butt plug would be a fun toy to start with and it could be left in for the rest of the day. He left the butt plug out of the bag and continued looking through. The maid outfit looked as if the skirt would cover less than half of Nicola's ass. Next up was a crop. It had a red handle at one end and the other end was a square strip of black leather. Oscar thought he'd have some fun with it now.

Nicola was still sucking his dick dutifully. She didn't seem to be aware that Oscar had made some selections from her recent purchases.

"That's enough, cunt. Strip out of all of your clothes and get down on your hands and knees in front of me facing away."

Nicola quickly took her mouth off of Oscar's dick and got up off the couch. She quickly peeled off her tank top exposing her round tits. Her skirt was still bunched around her waist. Nicola unzipped it just enough to push it down over her hips and take it off. Next she hooked her thumbs into the g-string and removed it as well. Nicola then got into the position Oscar had requested. The view was outstanding. Her pale asscheeks were thrusted up into the air which revealed her light brown asshole and pink pussy.

Oscar took the crop and held it firmly in his hand. He ran the end of the crop along the curve of her ass. He'd never used a crop before but could imagine it would amplify the force put in while swinging it. He brought it up and swung down to make contact right in the centre of her left ass cheek. It made a pleasing crack as it made contact and Nicola yelped in response to the pain. Oscar was excited and pleased. His pulsed quickened and his dick gave a throb. He quickly brought the crop up and back down again with another crack. Nicola jerked but held her position. Two light pink marks appeared on her ass cheek where the crop had made contact.

Oscar rubbed the spot where he'd spanked her with the tip of the crop and around Nicola's ass keeping her in suspense on when the next spank would come.

"That's two," said Oscar. "With the next ones, you're going to thank me, and call me 'sir' and keep count of how many spanks I give you." Oscar also instilled a feeling of arousal in Nicola so that she'd get turned on as the spanking went on.

He continued stroking her ass before bringing it up and back down onto her right ass cheek.

"Thank you, sir. Three."

In quick succession, Oscar continued the spanking.

"Thank you, sir, Four. Thank you, sir. Five." She was struggling to get the words out as the next whip would interrupt her.

"OH GOD, OW. Thank you, sir. Six."

As they went on, each stroke would elicit a loud groan from Nicola that was both pain and raw pleasure. Oscar slowed down around the tenth spank. The pink marks looked fantastic across her pale ass. It wasn't hard enough to bruise but hard enought that Nicola felt like her ass was on fire. Oscar went back to stroking around with the end of the crop. He moved it between her ass cheeks and let the corner of the leather strap graze over her asshole and down over her pussy.

"Good counting, whore," said Oscar, "Just a couple more. Grab your ass cheeks and spread them open for me."

Nicola responded. Her head and shoulders dropped even more as she took her hands off the ground and reached back. It caused her ass to stick even further up into the air. She pulled her cheeks apart.

Oscar rubbed the tip of the crop over her asshole again, letting her know what was coming. He brought it up and swung it down to connect right on the skin of her asshole.

"AHH. FUCK. THANK. YOU. SIR. THAT'S. TWELVE." Oscar pushed a feeling of extreme pleasure to Nicola. He saw her body give a shiver in the after effects of the spank. He let the crop again make soft contact with where it had just whipped her ass and gave a couple of soft taps right on the same spot before bringing it up and down with another hard crack.

kVia
kVia
337 Followers