Waitress

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New waitress has to please two men.
3.1k words
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condy
condy
1 Followers

Cassie had been excited about her first day at her new job. She'd been made redundant at her old job as a shop assistant, and was desperate to impress as a waitress in Creamo's restaurant. For her first night, she had taken great care on her appearance. She was only twenty and therefore put a lot of thought in getting the right balance – she wanted to appear mature and sensible, yet not unstylish or fake. She had been told to dress in a white shirt and black skirt, and she had gone out and bought new ones for the occasion. The shirt was quite baggy – she always had a little trouble buying formal shirts as the ones in her usual size tended to be too tight around her chest. She had done her best to avoid looking sluttish by buying one in a size up. She was also careful to ensure she wore her plainest white bra underneath, as she was desperate to maintain a classy appearance. On her legs, she wore black patterned tights, and a skirt that was longer than she would usually think to wear, but still showed off her shapely hips. It was the same one she had worn on her last date, which was two weeks ago now. She had visited Creamo's with one of her old work colleagues, Rick. During the meal, she had overheard that the restaurant was looking for a new waitress, and when she approached the manager he had seemed very pleased with Cassie. She had been encouraged to apply and now the job was hers. Rick had been pretty left out of all this, and Cassie had not made arrangements to see him again.

Cassie was nervous, but she knew she was a good employee and could do a good job. When Cassie arrived, she made her way thought the restaurant as instructed up to the small function room upstairs, where she knocked on a door and waited outside. The door opened and Chris greeted her. They spent about half an hour going through forms, health and safety guidelines and the restaurant's processes. Chris took Cassie on a tour of the restaurant and introduced her to the other staff – there were three other waitresses in, who all seemed friendly, and two barman, who would be working in the restaurant with Cassie. The kitchen was staffed by a separate team, but Cassie was told she would occasionally need to help the head chef, who was a big black man named Ben. After introducing her to Ben, Chris took Cassie back upstairs. He was happy with Cassie. She seemed to be taking the information in well, but more importantly she was a good looking girl and seemed likely to be very compliant. He was disappointed by her outfit slightly, when she had seen her at the restaurant previously she had been wearing a dressy, low-cut top, and he had really enjoyed the view of her cleavage. His cock tingled a little remembering it.

"A few words on your uniform there, Cassie," Chris said. "First of all, you need a badge making up. We like to give a friendly image, and so we do like you to have a little picture there on your badge, ok? I'm just going to take a picture now, and we'll use this machine here to get a name badge printed up for you."

Chris pulled a Polaroid camera out of his desk draw.

"We're just looking for a kind of passport style head shot, ok?" Cassie nodded and smiled at the camera, and Chris pushed the button. "That seems great actually. You'll get a more professional badge made up in the next couple of weeks anyway, if you stick with us. Your outfit seems fine, you basically look okay. Your shirt seems to be kind of poofing out a bit though, maybe you can tuck it into your skirt a bit more, make it look a bit neater?" Cassie was glad of the advice, and reached up her skirt and pulled her shirt downwards. This made it tighter, and Chris got a better view of the shape of her tits. They seemed quite big. Chris wondered what they'd be like without a bra on. He was 39, quite attractive, successful in business and still single. He'd experienced a lot of women, but it had been a while since he'd had anyone as young as Cassie. He missed seeing breasts that were large yet nice and perky. He was aware of his cock tingling again. "The other thing is Cassie, you really should have tied your hair back," he said, "but don't worry, I've got some spare bobbles in my drawer here." Cassie was still stood in the middle of the office from posing for her photo. Chris walked round and stood behind her. He used his fingers to brush her hair back and tied it into a ponytail. As Chris's fingers brushed across her neck, Cassie suddenly felt herself getting goose pimples and her nipples went hard. It felt very inappropriate, but also quite nice, for him to be touching her there. She began to start thinking about Chris, and whether or not he was attractive, but she got distracted when she noticed him brush against her back. She was sure she'd felt something hard brush against her arse. Cassie's mind started racing. Could he be attracted to her? Was he going to try something with her? What would she do if he did?

"There's something else I need to do for a second Cassie." Said Chris. He moved round to Cassie's front again, and began to unbutton her shirt from the top. He would usually wait a week or so before he tried anything with his employees, but he had to get a look at these tits.

Cassie looked shocked and stepped away. "What are you doing?"

"I just want to see," said Chris. "I'm the boss here Cassie. Let me do what I want. It'll be okay." Cassie needed the job. Chris had offered her really good pay. She decided to let things go a little bit further, and see exactly what it was Chris was expecting her to do. Once he had undone enough buttons, Chris reached round Cassie's back and unhooked her bra. He lifted it up to reveal her breasts. They were even better than her had expected. They had hardly fallen as he pulled the bra away. He put his hands on them and stroked the hard nipples with his fingers. Cassie looked surprised, said nothing and just watched what he was doing.

"These are really nice, Cassie. I think I'd like a picture, for later." Chris pulled his camera out again and took a few shots of Cassie, standing in the middle of the office with her shirt open. "Take your bra off completely for me." Cassie did as he said. She wondered how far Chris would go, but more importantly, how far she was willing to go to keep this job. She had no idea. "and push them together... yes, that's good. Ok, that's enough now." Chris took Cassie's bra out of her hand and placed it in his desk drawer, which he locked shut. "Do your shirt up, Cassie. Don't just stand there with them out like a whore. Or are you wanting me to do something else to you?"

Cassie shook her head and quickly fastened her shirt up. "Should I go and work downstairs yet?"

"Yes. That's all I needed you to do for me. At the moment. Go downstairs and speak to Marie, she will tell you what to do."

Cassie went down and was soon waitressing for the first time. She felt very self conscious, walking around with no bra on. In the kitchen she was fine, as it was very warm, but every time she emerged into the main body of the restaurant her nipples got hard again. This fact was very obvious through her white cotton shirt. Customers were looking at them. Cassie was not a shy girl generally, but this was embarrassing. A couple of the waitresses glanced at them also. Did Chris take their bras as well? Or did they just think she was a total slut? She continued to wonder what the situation would be with Chris. Would he ask her to do anything else, or would that just be a one off? Would she be willing to have sex with him to keep her job? He was quite attractive, she had decided. Cassie had not been with that many boys, and they had all been around her age. Chris was noticeably older, with some grey in his hair. However he still seemed to have a good body, and when he had brushed her back earlier Cassie had felt herself get a little turned on. She didn't know what to do.

Cassie was carrying some dishes back into the kitchen when she felt a hand on her shoulder. It was Ben, the chef.

"I saw your photos," he whispered in Cassie's ear. "Very nice." His hands were making their way up Cassie's shirt. He squeezed her boobs hard, and Cassie gasped as he began to flick her nipples harshly.

"Ow, don't do that," she said.

"The boss said I can do whatever I want. You're clearly a little whore, I bet you'll like a bit of rough treatment." He let her go, and she walked back out into the restaurant. Cassie was worried. He had sounded like they were likely to be rough with her. She would consider having sex with Chris to keep her job, on her own terms. She wasn't going to let anyone and everyone do what they wanted to though. It was a shame, but the job was not what she wanted. She would have to quit.

Cassie walked back up to the office to confront Chris.

"I'm not going to let you do whatever you want to me. I was happy to mess around with you a bit, I was really grateful of your offer, actually, but I have a feeling this is going to go too far."

"Okay Cassie. Bear with me one second. Go on, take a seat. I just need to go get the necessary form to fill it to say you don't want to work here." Cassie sat down. Chris left the room, and to Cassie's surprise looked the door behind him.

Shit, thought Cassie. She wondered what she had got herself into. She had the urge to bang on the door, but there was no one upstairs and she realised there was no chance of anyone from downstairs hearing her. Her phone was downstairs, in her coat. She was trapped. Whatever was going to happen, she knew she could do nothing about it. A drink – some kind of whiskey, Cassie presumed – was on Chris's desk. Cassie downed it.

Chris came back into the room, and with him came Ben.

"Right, Cassie. I'd like to have a bit of fun with you before you go. Try to relax, you'll enjoy it. We'll be really good to you." As Chris was speaking, Ben rummaged through Chris's cupboards. Cassie's hands were pulled behind her back and handcuffed together. Chris pulled out a video camera, pressed a few buttons and sat it on top of a filling cabinet, pointing at his desk.

"We've already seen your boobs Cassie, so I think I'd like to get a look at your pussy now. Is it very tight, Cassie? Is it very tight, or are you a whore? Do you give it out to all the boys? We'll see." Chris pushed Cassie back onto his desk. He was strong. He pulled her arms behind her back and handcuffed them to the leg of the desk while Ben pulled off her shoes. He lifted up her skirt and pulled her tights and knickers off. He spread her legs wide. Cassie felt the air reach her private parts. She felt exposed, and stupid for getting herself into this. She should have said no from the start. She realised she hadn't shaved herself down there since her date two weeks earlier.

"You've got a dirty hairy pussy. I think I'd like to make it nice and wet and sloppy. That would show how dirty you are." Chris carried the video camera over, and held it between Cassie's legs. He slowly rubbed one finger over her clit and watched it respond to his touch. He pushed the finger into her opening. "She is tight Ben," he said, "we'll have to be careful we don't stretch her". He put the camara away. He pulled something out of his drawer. Cassie couldn't see what it was, but suddenly she heard a familiar buzzing sound. She let out a gasp as Chris held a vibrator against her clit. She had a vibrator at home that she regularly used, this one seemed similar, although he seemed to have it turned up very high. Cassie tried to act disinterested, and pretend she couldn't feel it, but the lips of her pussy were already growing moist.

"Do you like what I'm doing to you Cassie?" asked Chris.

"No." Said Cassie, staring at the ceiling.

"I know you do. I bet you do this to yourself every night. I bet you love playing with your little pussy. We can tell you're a little slut, that's why I hired you." Cassie did have a vibrator at home, however she usually used her fingers to make herself come on a night, before she went to bed.

The vibrations began to circle round her clit, which began to feel warm and throbbing. Cassie began to wish for something inside her. She was doing her best to thing of other things. Maybe she could think of a way to get out? It was hard to ignore the warm feelings running around her body. She could feel her pussy relaxing, preparing to be entered. She felt her face start to crunch up as she did her best to hide the fact that she was approaching her orgasm.

"You've turned bright red Cassie. Are you embarrassed to come for us? I know you want to. I want to see your little body shake, for my video."

Cassie was getting really turned on. She stopped caring so much about her situation. She may as well make the most of it, right? She began to long for a cock inside her. She wondered what they would be like. The vibrations stopped.

"That's enough for now. Your pussy's dripping. You need to please us now." Chris and Ben both pulled down their pants and pulled out their cocks. Ben's was average sized, but Chris's was bigger and thicker than Cassie had had before. She wanted it in her quite a lot.

Ben rubbed his cock over Cassie's face. He rubbed it on her cheeks and lips. She stuck out her tongue and let him slide himself across it. Chris pushed himself inside her. She felt stretched by him.

"it's so big..." she whispered.

This spurred Chris on, and he slammed it into her hard. Cassie gasped. He began to fuck her with hard thrusts which made Cassie gasp.

"Do you like it?" asked Chris. "I can tell you love my cock."

Ben unbuttoned Cassie's shirt. He stood next to the desk and took hold of her ponytail. He pulled her head up and began to thrust his dick in her mouth. Cassie was gasping for air – she was good at blowjobs but it was hard while she was being fucked at the same time. She tried to concentrate on sucking him properly, but with Chris fucking her and Ben pulling on her nipples it was hard for her to concentrate.

Chris was also finding it hard to keep his cool. He'd been desperate for Cassie since earlier. He grabbed her hips tightly and ground his cock into her. His balls slapped against her bum. Soon it was too much. He pulled his cock out and held it over Cassie, jerking it fast. He moaned as he let out his load of hot cum, which landed over Cassie's tits. He used his hands to rub it over her breasts. Ben took his cock out of her mouth, and Chris wiped his hands across her face and cleaned the cum off his fingers with her mouth. "Do you want to come, Cassie?" he asked. Cassie was desperate.

"Yes," she said.

"We'll uncuff you then. We'll let you play with yourself, but you're not allowed to come until you've made Ben come, Ok?"

"Ok."

Ben freed Cassie's hands, and pushed her onto the floor. He pulled her into a kneeling position.

"If you're not pleasing me, I'm going to pull your hands away, okay? Now play with yourself while you suck me."

Cassie was desperate to please Ben, but she was also desperate to make herself come. She rubbed her clit ferociously with her left hand, and used her other hand to work Ben's cock. She sucked the tip of it. Ben moaned. He was enjoyed this for a while, but he wanted to be balls deep in Cassie's face. He pushed her hand away and placed his hands on the side of her head. She was glad of this and used the other hand to finger herself while she rubbed away at her clit. Ben was thrusting his cock right to the back of Cassie's mouth into her wet throat. She could feel Chris's cum dripping along her boobs and stomach. Cassie's felt so good. The pleasure she was giving herself was amazing, much better than it usually was at home alone. She heard Ben moan and felt his cum suddenly fill up her mouth. There was a lot. She tried to swallow it but some dribbled down her chin. She moaned loudly as she began to come herself. She stared up at Chris and Ben, her face and body splattered with she cum, and as she enjoyed her orgasm her mouth opened and her head tilted back. She rubbed herself for a few seconds longer.

"Well." Said Chris. "I thought that was good. I told you you'd enjoy it Cassie. I'll leave you to clean yourself up. Then you can go home, I guess. Do have a think about the job though. You were really good today, if you decide to come back I think I'll give you an extra three pounds an hour." Him and Ben left the room, and Cassie was left to clean herself up.

condy
condy
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4 Comments
AnonymousAnonymousover 14 years ago
wished i was her!

wished i was her!

AnonymousAnonymousalmost 15 years ago
Good Story II

I agree w/ "good story". Longer would be a plus. I especially liked her trying to focus on a blow job while someone else is fucking her pussy. I thought that was a nice touch. I'd like to hear more about her conflict between letting someone whom she didn't know examine her body and her need for a job and perhaps being involved in a three-some. "Dumb" puzzles me. If he doesn't like the story, the general content of the story, etc., what is he doing 1) finishing reading the story and 2) on this web site to begin w/? I'm curious about what stories someone like that rates highly. I notice that the highest rated stories tend to be stories about gays.

AnonymousAnonymousabout 15 years ago
Good story

but it could have been a bit longer and you could have drawn out the sex scene a lot more rather than "jumping" into it, so to speak.

AnonymousAnonymousabout 15 years ago
Dumb

However I consider the source and the audience

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