A/N: Wow, this is my tenth story and I really hope you guys like this enough to REVIEW, FOLLOW, AND FAVORITE it. I got this idea from the TV show Mad Men hence the title. Many pairings to come, later on in chapters so I really hope you guys like what ideas I have to offer to the story. All TVD names are the same and will not be changed.

I'll try not to make them OOC for your guy's sake, but if they do then *shrugs* what can I do? I'm so nervous about this story so again I really hope you all like and love it. THIS IS AN ALL HUMAN FANFIC…NO SUPERNATERUAL EVEN THOUGH I WISH I COULD!

I DO NOT OWN ANY THING OF THE VAMPIRE DIARIES OR MAD MEN!

Story is set in the 1960's in Manhattan

All African Americans in TVD will be treated equally, but there will be racism so I'm sorry if any of you get offended by this and then there is sexism. Again very sorry, but it's because of the time period that this story is set in.

RATED M FOR A REASON!

Caroline's Dress, Bonnie's Dress is #5, is now on my profile under the story's name.

Bonnie was entranced at the busy office. Everyone was working well typing at least. The people who typed their fingers away were women and the men were either stuck in their offices' or in a meeting. She couldn't help, but smile at all of it. Me, she thought excitedly, a working girl now, making my own money instead of being a housewife like most of the women were. She disliked having nothing to do all day, but take care of the children, clean the house, or make dinner for her husband.

She was happy that she was still a free woman. Yes, men would "ask" her parents for her hand in marriage, but the choice was hers…and she always said no, wanting to become something more than some silly housewife. Although, she would never voice these opinions aloud in fear of exile or exclusion, but people back in Brooklyn knew that she was very picky about people.

She dare say that her father was proud of her a little though her mother was a different story. She was taught to be a proper lady and that she did become. She was also taught determination from her father so you beat that she worked her ass off to get to where she was right now. Yeah, sure it was only someone's assistant right now, but she had hoped that, that will change someday. She was lucky enough to even be here right now according to her neighbor, Lucy. Bonnie noticed that everyone seemed to be smoking or drinking their way to an early grave in alcohol. She never liked to drink or smoke, but here in the city, it was considered an everyday routine like taking a shower or brushing your teeth.

"Keep up!" she yelled at her.

Bonnie jumped a little in fright and quickly followed behind the tall blonde woman named Caroline. She was very beautiful and blonde too so naturally every man in the office looked at her hungrily, but she simply ignored it. She didn't blush at them or give them a wink or smile, no she just kept on walking. Bonnie wished that she could be like that. Not being able to blush of course, but she did wonder what people were thinking about her right now. She already knew that she was the only colored woman that worked there instead of service.

Bonnie's hair was pinned up in an elegant updo like most working gals had their hair done. She decided to go with her buttoned sided dress that reached up to her knees; it was plaid with the colors of blue and white. Bonnie held her box of supplies in her arms as she quickly followed Caroline. She envied Caroline's figure and her outfit of choice. Caroline was one of those girls that were able to show skin, make it look beautiful and not trashy, and how every thing she wore went with her figure. Caroline did have a look like a model's and even though her dress was grey, she resembled a housewife especially with her short curly blonde hair.

Her lips were a soft pink and you could tell that she used a pearl powder in order to make her face look natural. Caroline walked with a sway to her hips in her walk. Her dress was off the shoulders in an elegant way and she had a pearl necklace decorating her neck. Somehow, Caroline's hair stood in its exact place no matter what she did while Bonnie's was kind of irritating to keep. Bonnie was being led to her desk. She was going to be the secretary of Mr. Damon Salvatore.

The Salvatore Company was very; very well-known in New York and it was the dream place to work in. It was the central company for pretty much every other type of business. They invested in aircrafts, ad campaigns, taxes, telephones, automobiles, TVs, cigarettes, alcohol, commercials, food companies, restaurants, beverages, art, department stores, cosmetics, hair products, and Bonnie doesn't know how, but in some way they have people who are willing to test out the products. Basically, the company invested in every type of business like Coco-Cola, in just one meeting they said yes to their company and in just a month they soon became the biggest thing on the market.

Bonnie looked around the office and she noticed that it was modern and very large. Each office door had someone's, a man's name on it. She also noticed that every woman's hair was up, their nails were painted, and their skirts were above their knees, some even higher. The only sounds in the office were the sounds of typewriters' keys being pressed, and the phones ringing off the hooks.

"You will only address Damon Salvatore as Mr. Salvatore. You are at his beck and call. You will do whatever he says. When to do it and how to do it." Caroline told her, her voice sounding seductive yet sweet. Caroline stopped abruptly and turned around looking at her in the eyes saying, "Got it?"

Bonnie gulped and nodded her head rapidly. Caroline smiled and looked at her from up to down.

"Good." She turned back around and started walking again. Bonnie had heard about her boss…he was a womanizer which always made her blush every time she thought about it. Yes, she had heard many things about him and most of them had to do with his appearance and background. She heard that he was a workaholic, a smoker, but then again everyone was, and he was an alcoholic. That pretty much described everyman in the world right now.

Caroline stopped at the office in the corner and pointed to the bare desks that one was vertical and the other was horizontal. The vertical had a typewriter with a stack of blank paper on the side while the horizontal desk had a lamp, some pencils and pens, and some files and paper.

Caroline smiled at her and said, "When Mr. Salvatore comes in, you'll take his coat, his hat, and his briefcase."

As Bonnie put her box of supplies down on the desk, she asked Caroline, "So who do you work for?"

Caroline tilted her head to the side and a little and put her hands on her hips. "You are so sweet." She sighed. "It almost makes me sad to not be so young anymore."

"You don't look old. In fact you look very young and you are very pretty." Bonnie said and Caroline laughed.

"Like I said before you are sweet…" Caroline trailed off obviously wanting to know her name even though she already told her it.

"Bonnie. Bonnie Bennet." She said brightly, holding her hand out, but Caroline looked at like it was a something not proper and she knew it was because of her skin color.

Bonnie brought her hand back and smiled a little. "It that all?"

Caroline sighed again and turned around walking in the other direction towards the office with double doors. Bonnie had read that her boss was the eldest son of Giuseppe Salvatore was the heir to everything his father owned. They were for sure the wealthiest family and people in not just New York, but possibly the country. They had two sons, Damon, and Stefan who was the younger one and lived in the shadow of his brother. Bonnie had also heard that their mother, wife to Giuseppe surprisingly kept out of the media. She didn't hear much about her only that she was a housewife like most women, but she didn't take crap from her husband…sometimes at least.

Bonnie set her supplies in place on her desks and sat in her seat with a low sigh. She waited for her boss to come in and luckily she didn't wait that long. Once he walked into the office every woman looked up from whatever it was that they were doing in order to look at him and greet him sweetly, "Good morning, Mr. Salvatore.", but Bonnie did no such thing.

She was too busy putting the files that were on her desk in order by alphabet and Damon noticed this. Just as he was coming towards her, taking off his hat, she stood up and waited. She took his hat and helped off his coat and followed him inside the office. He had books on each of the tables, very old books, but still put together. Damon put his briefcase down and turned to her as he stood at the head of his desk.

She hung his coat and hat as he asked her, "Who are you?"

She turned to him and replied, "I'm your new assistant, Mr. Salvatore. My name is Bonnie Bennet. Now is that all?"

Damon couldn't help, but stare at the young girl in amazement and lust. He already wanted to bend her over his desk, let her hair down, rip off her clothes, and fuck her senselessly. She was beautiful, very beautiful in his opinion especially for a colored person. She looked so mousy and proper in some way that probably made her irresistible to all men. She appeared to be very young to Damon and to him he thought that maybe she might be the youngest woman in the building.

"Mr. Salvatore?" she asked lacing her fingers together in front of her.

He nodded. "Yes, that is all, Bonnie."

She smiled and walked out closing the door behind her as she left. Damon let out a breath that he didn't know he was holding and looked down at the pile of work he knew that he had been putting off. Once he sat down and heard the door click, his eyes shamelessly glanced back up at the door, wanting to already see her again. Damon wanted her in that very moment…not just because she was the only woman to not look up, gaze at him, and then blush, no Damon wanted her because she was his assistant and that was the reason his father had even hired her in the first place.

His "loving" father had been picking Damon's pretty assistants for as long as he could remember. They were all pretty and not that very bright, but none of them had ever been colored. Bonnie Bennet was very pretty indeed and Damon had already guessed that, that was the main reason she even go this job. Damon had, had sex with many women especially his assistants.

Damon smirked mischievously at the thought he just had about what in the name of God was he going to do with Miss Bonnie Bennet.

TBC…

A/N: So I hope you all liked this new story that I had in my head for some time now. REVIEW, FAVORITE, AND FOLLOW! Thank you all for taking the time to read this little ol' story. So yeah, their dresses are up on my profile if you guys wanted to get a picture of what they look like.