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Published:
2019-01-24
Updated:
2020-01-12
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161,070
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52/?
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Yes, Mr. Reddington

Summary:

Liz Keen is dissatisfied with her life, and she sees a Help Wanted sign in the window of a law firm. She applies for the job on a whim, and is hired as Raymond Reddington's secretary. He is eccentric and demanding, yet irresistible to her, so she obeys his every instruction. They embark on a strange, yet satisfying relationship.

Notes:

This is a story where the Blacklist characters are put into the Secretary (2002) roles. James Spader was the 'original Mr. Grey' in the movie Secretary, which I love, so I was inspired to combine the premise and aspects of it with the characters from the Blacklist.

I was also inspired by the song "Not Afraid Anymore" by Halsey, from the Fifty Shades Darker soundtrack (with lyrics): https://youtu.be/9WNxDRJb5ow

Disclaimer: I do not own the characters or The Blacklist or Secretary (2002), and I don't make any profit from this. It's strictly for fan entertainment purposes.

Chapter 1: Help Wanted

Chapter Text

 Liz was generally dissatisfied with her life, and she was craving something new and different. As she sulkily meandered down the street with a cup of coffee, she noticed a Help Wanted sign in the window of a law office. Something about it piqued her interest and she found herself heading for the office building. She went in the front door, looked around the small, modest waiting room and sat down. Liz was alone, but she could hear a man’s voice talking on the phone in the office down the hall. He had a nice voice. She waited for several minutes, sipping her coffee and taking in the surroundings.

 Raymond had heard the door, but he was stuck on the phone with a client who was arguing with him. Without a secretary, he had no one to address the person who came in. He was relieved when the client finally conceded and he was able to get off the phone. He hung up and swiftly walked out into the waiting room to see a strikingly beautiful young woman with dark hair. 

 Liz laid eyes on the man as he walked into the waiting room, and she was struck by how attractive he was. She suddenly felt very self-conscious, and smoothed her hair with her hand before standing up to greet him. 

 “Sorry about that. I don’t have a secretary at the moment. How can I help you?” The man said. 

 “It’s okay. I’m actually here about the Help Wanted sign…” Liz said. 

 “Ah. It’s for the secretary position…obviously.” He said. 

 “Right. I can be a secretary.” She said eagerly. 

 Red was amused; she didn’t seem to know what she’d be applying for when she came in. 

 “Very well…I’ll need to interview you.” He said. 

 “Of course.” She said. 

 “How about right now?” He asked. 

 “Sure.” She agreed. 

 They stared at each other for a few moments. 

 “Okay, well, come into my office…but throw that out first.” He said, gesturing to the coffee cup. 

 “Oh…Okay.” She said, then she went over to a garbage can and carefully put it in, as it was still almost half-full. 

 Liz turned back to the man and he’d been watching her like a hawk. 

 “…That’s better. This way, please.” He said, leading the way down the hall into his office. 

 “Sit.” He said.

 Liz sat in the chair across from him, and waited. After a few moments, he spoke. 

 “I’m Raymond “Red” Reddington, as indicated on the front door. I need a secretary.” Red said, then he leaned back and put his fingertips together in a contemplative manner.

 Liz realized he was waiting for her to say something. 

 “Oh. I’m Liz Keen. I’m—” She said.

 “Can you type?” He asked, cutting her off. 

 “Yep.” She said. 

 “‘Yes’ would be preferable to ‘yep’.” He said. 

 “Oh…Yes.” She corrected herself. 

 Red nodded. 

 “Can you answer the phone?” He asked. 

 “Yep—Yes.” She said. 

 Red approved; she was a fast learner. He leaned forward and put his hands flat on his desk. 

 “Do you really want to be my secretary?” He asked. 

 Something about his voice enticed her further.

 “Yes.” She said eagerly. 

 “It’s very boring work.” He said. 

 “I like boring.” She said.

 Red smirked amusedly, then he stood up; Liz stood up nervously. 

 “Welcome aboard, Lizzie.” Red said, extending his hand. 

 Liz didn’t correct him about her name. She took his hand; it felt strong and warm. 

 “Thank you, Mr. Reddington.” She said softly. 

 Their handshake lasted a little longer than necessary, then Red finally took his hand away. 

 “Can you start right now?” Red asked. 

 Liz was surprised, but pleased. 

 “Yes.” She said, smiling. 

 “Excellent! Now I want you to do something for me…” He said. 

 “…Yes?” She said. 

 “Show me how you’ll answer the phone.” He said. 

 “Oh. Um…” She said, nervously picking up the receiver on his desk. 

 “…You’ve reached the offices of Mr. Raymond Reddington, how can I help you?” She said, blushing. 

 “The law offices of Mr. Raymond “Red” Reddington.” He corrected. 

 “Oh. I have to say that every time?” She asked. 

 “Yes.” He said plainly. 

 “Okay. I mean, yes sir, Mr. Reddington.” She said. 

 Red smiled. 

 “Now let’s hear it. Do it again.” He said. 

 Liz stared at him for a moment, then she grabbed the receiver again. 

 “Hello, you’ve reached the law offices of Mr. Raymond “Red” Reddington, how may I help you?” She said. 

 She looked at him and his expression was something like admiration, but more lustful. She smirked slightly and basked in his approval as she put the receiver down. 

 “That was very good, Lizzie.” He said quietly. 

 Liz was thrilled. 

 “Thank you.” She said. 

 Red abruptly stood up and came around to the front of his desk, which made Liz nervous. 

 “I have something else I need you to do for me.” Red said, standing very close to Lizzie. 

 The inappropriate closeness, plus his tone made Liz think he was going to ask her to get down on her knees, or possibly bend over the desk. She was kind of hoping for something like that. 

 “I need you to type a letter.” He said. 

 “Oh. Okay.” She said, trying to hide her disappointment. 

 Red scrutinized her face very closely, and he could tell she wasn’t enthusiastic about the letter typing task. 

 “…Hm.” He responded. 

 He was so close, Liz was almost expecting him to kiss her; and again, she hoped for it but was disappointed. 

 “Now would be a good time to do the letter, Lizzie.” Red said. 

 Liz nodded and blushed lightly, then she followed him out of his office, back to the front desk. 

 “Have a seat and take my dictation.” Red said. 

 Liz blushed a little deeper at the slightly sexual sounding phrase. She opened the word processor, then he dictated a formal letter; she tried hard to keep up. She really wasn’t even that great of a typist, she’d just applied to be his secretary on a whim. When finished, Red leaned over Lizzie’s shoulder to inspect her letter. He smelled her lovely sweet shampoo, and he was a little distracted, but he recovered quickly when he saw how many errors she’d made. 

 “Delete it all and start over. There are too many mistakes. You need to get the hang of it.” Red said. 

 Liz reluctantly selected the whole letter and deleted it. Red started his dictation again, verbatim, and she wondered why he didn’t just type it himself. She felt like she did much better this time, but he didn’t approve. 

 “Again.” He said. 

 Liz felt angry, but also slightly excited. They went through the process again. 

 “Much better. Although, two typos are still too many. You don’t want me to look like an idiot to my clients, do you?” He said. 

 Liz now felt very bitter, and she was tempted to tell him to stuff the job up his ass, but something made her comply. She sat quietly, waiting. 

 Red leaned over her shoulder again.

 “Lizzie, you have to take it as I give it to you…listen to my voice and follow it carefully. Let my voice go through you, directly to your fingers…try that, sweetheart.” He said. 

 “Yes, sir. I will. I’m ready.” She said. 

 They were both becoming aroused from their tense, close interaction and the sexual innuendos. Liz blushed and Red wanted to kiss her pink cheek, but he refrained. 

 “Alright. Let’s do it again.” Red said, standing upright again. 

 He dictated the letter one more time, and when he inspected Lizzie’s work, he was dumbfounded. It was perfect. 

 “Excellent work, Lizzie. You clearly benefit from my directions. Don’t worry about being new at the job…I’ll give you a guiding hand.” Red said, close to her ear. 

 Liz wanted his guiding hand in her pants. 

 “Thank you, sir. What else would you like me to do for you?” She said eagerly. 

 “Nothing, sweetheart. That’s all for now. I’m almost done for the day, and you deserve a break. Go home. I expect you to be here at eight-forty-five a.m. sharp tomorrow.” He said, then he abruptly headed towards the hallway. 

 Liz stood up. 

 “Oh okay. It was nice meeting you. See you tomorrow!” She said after him. 

 Liz heard the office door close, so she left out the front door, still in shock that she’d gotten hired on the spot. Her thoughts were whirling as she rode the city bus home. She was listening to music, but it didn’t even really register with her; all she could think about was Raymond “Red” Reddington. His voice, his captivating eyes, the way he somehow commanded obedience from her…the way he made her feel. She noticed her panties had a very wet spot. Liz surprised herself; she truly would’ve had sex with him right then and there. She would’ve gotten on his desk, or the floor, or against the wall…or down on her knees in front of him…

 “Oh shit.” Liz said as she missed her bus stop. 

 She pulled the cord and got off at the next stop, then she walked home. She went in and took her shoes off; she looked around and felt depressed again. Being at the office with Raymond had given her a thrill, and this was a big comedown. She sighed and begrudgingly did some dishes and then had cereal for supper. After supper, Liz watched some TV and then decided to have a bath. She ran the bath and got undressed, then she stepped into the soothing warm water. She sighed as she sat down and got comfy, and as she closed her eyes, her mind kept wandering back to Raymond Reddington. 

 You have to take it as I give it to you… She recalled him saying. That was so sexy. She pictured him saying that to her while she was bent over his desk. Liz sighed and put her hand between her legs as she imagined him behind her, commanding her to open her legs for him. She pressed in circles on her clit as she went further into her fantasy. She pictured what it might be like to have him enter her from behind while she grasped his desk. Liz whimpered quietly and moved her fingers more quickly. She imagined him telling her to kneel, unzipping his trousers and pulling his erection out. She whimpered again and her fingers went back and forth on her clit. In her fantasy, Raymond told her to “take it” so she took him into her mouth and began pleasuring him. Liz was on the verge of climaxing. 

 “Ohh Mr. Reddington…” She whispered.

 Her fingers moved very quickly as she pictured him coming. Liz suddenly let out a sharp breath and succumbed to the waves of pleasure. When her orgasm finished, she sighed and wished it had been more than just a fantasy. She felt a bit disappointed; it had been anticlimactic, despite the orgasm. Liz felt depressed again as she reflected on the fact that she was alone in her bathroom, desiring a man she’d just met, who probably had no interest in her other than as an employee. She washed and rinsed, then got out of the bath. She dried off and put some pyjamas on, then she watched TV again until it was snack time and then bedtime. 

 ~ ~ ~ ~ ~ ~ 

 Red’s evening at his apartment was boring and lonely; he did some preparation for what little cases he had to work on, then he watched TV until it was late. He undressed down to his undershirt and boxers, then he got into bed. When he closed his eyes to try to sleep, his new secretary, Lizzie, popped into his mind. She was a very alluring young woman, and so eager to please him. He turned onto his back and let his mind wander further. He bet Lizzie would eagerly submit to him if he wanted her to. She would sit on his desk and lift up an expensive pencil skirt, revealing no panties underneath. Red pulled his boxers down and began stroking himself as he imagined her bending over his desk, with her naked butt swaying seductively as she waited to be penetrated. 

 Red breathed heavier and pushed his tip through the tight space between his thumb and forefinger as he pictured entering Lizzie. In his next fantasy, he told her to spread her legs as she sat on his desk, and he knelt down. He could picture her blushing as he put his face between her legs. Red tightened his grasp on his erection, then he used his thumb to carry the slippery precum from his tip downwards. He wished he was getting slippery from Lizzie’s fluid instead. He gave himself quick, tight strokes as he imagined her bouncing up and down on him. 

 “Oh fuck…” He said very quietly.

 He went very tightly over his tip and just past it, then he felt the immense pleasure wash over him as he came. He spurted onto his undershirt, so when the pleasure died down, he took the soiled garment off and threw it on the floor. Red sighed and relaxed, wondering if he’d be able to remain professional around Lizzie, or if he should seduce her, since she seemed so ripe for it. He would have to test her first, to see if she could handle his proclivities. 

 ~ ~ ~ ~ ~ ~ 

 Liz walked into the law office and the clock showed 8:44 a.m., so she was hoping to be praised by Raymond for being on time. He came out of his office. 

 “Good morning, Lizzie. I need you to type up these notes. I hope you can read my writing. Oh and a coffee wouldn’t go amiss…” He said. 

 Liz was a little astonished. 

 “Oh. Okay. I’ll get you a coffee first. How do you take it?” She said, putting her purse down behind the front desk. 

 “Milk and two sugars; and be quick about it. You need to be working at the desk when people come in.” He said. 

 “Do you have an appointment at nine?” She asked. 

 “No.” He said plainly, then he went back into his office. 

 Liz was puzzled, but she went and found the kitchen and figured out how to work the coffeemaker. She then added milk and two sugars to the coffee, which was the same preference as her own. She stirred it and brought it to Raymond’s office. The door was ajar, so she knocked. 

 “Yes, Lizzie. Come in.” Red said.

 Liz gently pushed the door open and walked in, brandishing the mug of coffee. Red surveyed her and he just realized she was dressed up in a skirt and blouse, wearing some makeup. She’d obviously put extra effort into her appearance. 

 “Where would you like me to put it?” Liz asked. 

 “Right here on the desk.” He said.

 Red pushed some papers out of the way, purposefully sliding them off so they fell on the floor. Lizzie put the mug down and then she automatically turned around and began picking up the papers; her butt was extraordinary, especially in a skirt. Liz could feel Raymond’s eyes on her, and she felt a thrill. One of the papers had gone farther than the others, so she decided to make quite a show of getting on all fours and reaching under the file cabinet to get it. Red was getting hard as he sat at his desk watching her. She got up and came over to him with the papers. 

 “…Thank you, sweetheart. How clumsy of me.” Red said as he took the papers from Lizzie. 

 “No problem. Let me know if you’d like me to redo it…” She said teasingly, then she turned and left before he could respond. 

 Liz sat at her desk feeling very excited; Raymond had obviously enjoyed her little performance, and her cute snarky comment. She took a deep breath and concentrated on the stack of notes she had to type up. As she worked, she heard him on the phone several times, but they had no clients or visitors. It was now three o’clock and Red came out of his office. 

 “You can go home now, Lizzie. We’re done for the day.” Red said, putting his jacket on. 

 Liz was disappointed; she wanted to stay there with him for as long as possible. 

 “…Are you sure? I can stay until five.” She offered. 

 “I’m sure.” He said, collecting his briefcase. 

 “Did you want to check my work?” She asked hopefully. 

 “No. I’m going to lock up now, so…” He said. 

 Liz was peeved, but she grabbed her purse and went outside. She lingered, watching him lock the door. He looked at her. 

 “Have a good evening. I’ll see you tomorrow.” Red said, then he went to his car and got in. 

 Liz still lingered and watched him drive off, then she went to the bus stop and sat down on the bench. She caught the next bus and went back to her apartment, where all she had to look forward to was the next day, when she’d see Raymond again. 

 (To Be Continued…)