Ashleigh seemed like the typical pretty girl - tall blonde with piercing blue eyes and a bubbly personality. But there was more to her, she was ambitious and already working a couple of part time jobs during her first year at college to start saving up for her dream of attending law school. Despite all that and having decent grades, Ashleigh couldn't help but feel jealous of her slightly older sister Mia who was also at the same college. To Ashleigh, Mia appeared even hotter with her brunette locks and bigger chest that she liked to flaunt. It was crazy that Mia could attend all these fun sorority events yet have a better GPA than her. Ashleigh was determined to do it her way and grind it out no matter how hard she needed to study or how many part time gigs it took.
Ashleigh was currently working at one of those jobs, bartending during a busy weeknight. There was a creepy older guy who has been staring at her all night and trying to strike up a conversation whenever she walked by his area. Ashleigh was truly busy this night and couldn't have talked much even if she wanted but she did not want to give him any more attention besides serving additional drinks. She had her morals and wouldn't lower them just to get a better tip. At least this shift wasn't all bad, Ashleigh thought. There was a hot guy in business attire that caught her eye on occasion. But she knew she had to focus on her work.
Exhausted from a long day of school and work, Ashleigh went back to her dorm room and straight to bed. Her roommate Diana was still up studying. She was a geeky but pretty Chinese girl studying science with aim of getting into med school. While her parents forced her academic ambitions, Diana was also interested in fashion and modelling. She had a very toned body and was especially proud of her ass that she worked hard to maintain in that firm shape during her gym sessions. But like Ashley, she wasn't blessed in the chest department.
Diana: "Rough night at the office?"
Ash: "Ughh...please kill me know. Midterms are coming up and I'm still a few lectures behind. I don't know how I can keep it up with all this stupid work."
Diana: "Speaking of that, there's this application that just came in for a paid internship. It's not for me but may be something you wanna check out?"
Ash: "Thanks, put it on my desk. I'll take a look in the morning."
The next day, Ashleigh filled out the application. It couldn't be any worse than bartending plus she'd get paid unlike most of the unpaid internships that were available to her. She was pleasantly surprised to get an interview for it soon after. Luckily, the building was in the business hub near campus so she could go over during her lunch break. Ashleigh wore a knee-length black pencil skirt and white blouse to the interview with her hair tied up in a bun. She didn't normally like walking in high heels but she wanted to look nice and professional. She was so nervous, she didn't even notice the lustful male stares she was receiving in this outfit. When she arrived at the instructed floor, Ashley noticed a familiar handsome face just outside the elevator. It was the hot guy from the bar! He walked over and introduced himself as Tim.
Tim: "Hello, I am Tim. You must be Ashleigh?"
Ash: "Ugh, yeah...hi, yes. I'm Ashleigh but you can also call me Ash."
Tim: "Alright, please come this way Ashleigh."
They went into a small conference room and started the interview.
Tim: "So, thank you for applying. Tell me about yourself."
Ash: "No, thank you for this opportunity. Uhm...well, I'm 18 and it's my first year here at college. I'm focusing mostly on English and History courses right now but my goal is to get into law school. I'm very self-motivated and a team player. I'd love to get this job, sir, and help your business succeed."
Tim: "You can just call me Tim, no need to be formal. So what exactly do you know about our business and this role you are applying for?"
Ash: "Well...Tim...to be honest, I've been so busy with school and work that I didn't really do much research. Basically my roommate told me about this application and I decided to go for it."
Tim responded that he appreciated her honesty and continued with the questions. Ashleigh was relieved once the interview was over and they began to wrap up.
Tim: "Based on your application and interview today, I can see you're the most suitable candidate and would like to offer you the position."
Ash: "Oh my god, really? Wow, that is amazing! Uhm...what exactly is it that I'd be doing?"
Tim: "Well, your title would be 'Executive Assistant Intern'. You would need to assist me with my schedule and after-hours activities while you're not as school, of course. Basically help me with anything that needs taken care of so I can do my job efficiently when I'm working late or even outside the office."
Ash: "Yes, I can totally do that, sir...I mean Tim. I am happy to accept the job!"
Tim: "Great, we'll be in touch and I look forward to working with you soon and having you on the team. Know that I deal with many lawyers as part of my business. If you do a good job, I can introduce you and help you network."
Ashleigh scaled back some of her part time work while juggling her various responsibilities as best she could. In between her classes and while studying, she would clean up Tim's schedule on the company iPad she was given. She also spent a couple hours in the office and around town every other evening to take care of errands for Tim. After a few weeks, he asked Ashleigh to come in for a chat. He explained that she was doing a great job and that he could trust her to take on a new responsibility that would be mutually beneficial. He wanted her to start joining him on some of his business dinners with clients.
It was time for the first such business dinner a few days later. Ashleigh stepped out of the cab in front a fancy restaurant wearing an outfit Tim had sent her to wear. She went inside and was ushered to the table where Tim was already sitting with the client. Ashleigh was feeling shameful wearing the dress he had sent her but she assumed it was an honest mistake as he wouldn't have known her exact measurements. It was a beautiful red dress that hugged her fit upper body but was so short that it barely covered her crotch. As she approached Tim's table, she noticed the client sitting with him was in his 40s or early 50s and wearing a fancy suit. When he saw Ashleigh for the first time, he nearly spilled his drink. She looked gorgeous and thanks to the ultra short dress and 5-inch heels she was wearing, he could see the bottom of her black panties from his low sitting position while also admiring her long toned legs. Tim was seated at the only chair by the table, so Ashleigh had no choice but to sit next to the client on the bench opposite from a smiling Tim.
