Ashleigh couldn't believe she had given a blowjob as part of her job. Where were her morals? Her initial feelings of anger gave way to shame. Should she even tell her boss Tim about what had happened? She knew she would have more time to stew on that as he was out of town for a few more days. For better or worse, Ashleigh's worries turned towards her finances which were not looking great. Her financial aid was guaranteed only for the first year of college and she wasn't making enough money from the paid internship and bartending to help cover all costs going forward. Unless her grades improved to be eligible for new scholarships, she would have trouble continuing her degree let alone saving up for law school. Most of her parents' savings had already gone towards her sister Mia's college fund so she didn't have much choice but to rely on herself. This was all too much for the 18 year-old to handle. Her roommate Diana noticed something was amiss and they talked about the financial burdens. Ashleigh didn't know if her roommate could really understand what she was going through considering Diana's parents were loaded and money wasn't an issue for her.
A few days later, Tim was back in the office and Ashleigh went over after school to resume her executive assistant duties and have the dreaded discussion about the Howard situation.
Ash: "Welcome back Tim. I have completed all the assigned tasks while you were away and updated your schedule with upcoming meetings. Let me know if there's anything else you need me to do for you tonight. And...there's also something else I wanted to talk to you about."
Tim: "Hello Ash, the Howard deal went through smoothly and he was very happy with your assistance."
Ash: "Yeah, that's what I wanted to talk to you about. You see, he..."
Tim: "I'm very proud of you Ash for stepping up. Howard told me everything you did."
Ash: "Well, that's the problem I wanted to discuss. It's not something I..."
Tim: "As a reward, I want to offer you a permanent position for $10,000 per month along with generous benefits. You can still go to your classes but I expect you to drop your other activities and be available to assist me at all times when you're not at school."
Ashleigh was in shock. This is not how she had envisioned the conversation going. Her frustration was starting to grow as Tim kept cutting her off and asserting his dominance but this new development was a potential game changer. Then worry started to creep in for Ashleigh that the offer seemed too good to be true.
Ash: "Wow, ten grand per month! That's a lot of money. What...exactly would you expect me to do though?"
Tim: "I would expect you to continue providing me the same great assistance you have demonstrated so far and to ensure client satisfaction is always met. Word has spread about your 'oral skills'. That will now become a strong asset in our 'client negotiation package'."
Ash: "No, no, I can't do that. Not again. This is wrong! "
Tim: "That is disappointing to hear. It sounded like you were the one to take initiative and exceed Howard's expectations. So, take the rest of the night off and get some rest. Once you come to your senses, I'm sure you will appreciate the offer. Of course, there are always bartending openings if that is more to your liking, Ashleigh."
Ashleigh tried keeping her composure but couldn't stop shedding some tears once she had left the office. Her mind raced in different directions on her way back to the dorm. (Fuck, what do I do? There has to be another solution. Why am I even thinking about this? I need to tell him 'no' asap and get it over with. But... it's a lot of money though; it would more than solve all my problems. And it's all just part of business so everyone would be discreet. Right? What am I even thinking? No, this is gross and beyond embarrassing. I can't believe I'm even considering it! Damn it, I need to find some other way of making money. I know I just spent the last few days saying that's impossible but I need to keep thinking. Think, c'mon think!)
Ashleigh got hardly any sleep that night and barely paid attention during her lectures the next day. With her mind finally made up, she went over to the office after school. Once again, she tried her best to keep her composure and remain professional in front of Tim despite how disgusted she really felt.
Ash: "Hello Tim, I have decided to accept your offer. I just want to confirm that I can terminate the contract at any point if I am no longer comfortable with this arrangement."
Tim: "Excellent choice. I knew you were a smart girl and would make the right decision. To answer your question, yes you are free to quit should you ever want to do so. But I doubt that will cross your mind once you begin appreciating what this job has to offer."
After an awkward pause, Tim continued: "You know, I'm also putting my reputation on the line and trust that you will perform your tasks as expected. So it's a two-way street and I can easily terminate the contract as well if you don't meet mine or the clients' satisfaction".
Ashleigh finally responded with clenched teeth: "Thank you Tim, I look forward to continue assisting you and our clients."
After that, Ashleigh settled into her new routine. When not sleeping or trying to find time to do her schoolwork, Ashleigh was either attending classes or doing work. The latter still involved assisting with Tim's errands and going on business meetings. But for the clients interested in more than just flirting, they had the 'Ashleigh Special' to look forward to. She would help get them off by giving blowjobs. They had different preferences with some leaving it up to Ashleigh to pleasure them while others took charge and face-fucked her. Some would give her a facial while others preferred ejaculating inside her mouth. The worst for Ashleigh were the ones that demanded she swallow the cum. The taste was usually gross and it made her feel extra cheap the rest of the night. But she kept telling herself that this will all help in the long run of getting into law school and then landing her dream job.
One Saturday afternoon, a package arrived for Ashleigh with a note from Tim: "Be ready for 7 pm dinner with very important client Jerome. Put on the exact outfit that's in the package and nothing else! Also wear your highest heels, you will need them." Ashleigh realized the outfit did not leave much to the imagination once she had put it all together and looked at herself in the mirror. While the sleeveless dress technically did not show much skin besides her arms, it was made of a thin transparent material. Making matters worse was that the package also included see-through lingerie. Ashleigh felt exposed and vulnerable as her nipples and pussy were visible under the right lighting and viewing angle.
But she did as instructed and showed up for dinner in this outfit. Ashleigh walked nervously in a slow manner to conceal her private parts as best she could. When she finally reached the table, Jerome stood up to introduce himself. Despite being relatively tall and wearing 5-inch platform heels, she still had to look up to meet his eyes. He was about 6'4" with a large muscular upper body that was apparent even through his business suit. Jerome looked more like an NFL wide receiver than a typical businessman. After dinner was over, he asked Ashleigh to come with him to his hotel room.
