27 comments/ 100181 views/ 45 favorites The Diary of a Personal Assistant By: sexandthecity77 My name is Dawn Hughes and I have been a personal assistant for business men and women, as well as a few B-list celebrities sprinkled here and there. I've been doing this for 5 years since I graduated from college. And I have to say that I enjoy the job. It's not to say that I haven't had my fair share of incidents occurs on and off the job as a personal assistant. There's always some client that think that personal assistant means that I get to do all the menial and degrading jobs under the sun. One of my clients called me over at 5 am to unclog a toilet....I had only been working for her for 2 days before I had decided enough was enough. But, that's not even the worst experienced I had while working for someone. But that particular story should be explained in more detail... Monday morning, I woke up bright and early for my interview at Clarke, Patterson, and Schwartz. Clarke, Patterson, and Schwartz is a high end Banking and Insurance corporation downtown. They rarely ever have job openings for personal assistants since their offices are never short of busty blondes and brunettes looking for their future husbands among the middle aged partners. I, on the other hand, am far from that description. I am a beautiful black woman...well I think my complexion is more milk chocolate than black but you get the picture. I have long beautiful black wavy hair thanks to my Native American background, Cherokee Indian to be exact. I stood at about 5'8 with long shapely legs. I have always been told that my body is curvy in all the right places, which is true. I have a plump butt, a narrow waist, and a round set of 36 C breasts. I was blessed with great facial features as well. Oval face, high cheek bones, big expressive almond shaped brown eyes, and luscious full lips. I wouldn't change a thing. But enough about my looks. I was nervous about the interview because I didn't consider myself Clarke, Patterson, and Schwartz material. But mostly, I was nervous because I needed this job badly. This was my last shot and if I didn't get this job, I would have to move back home. And I was not about to let my dream of living and making a name for myself in the city come crashing down like that. It seemed as though I had entered a modeling casting call rather than a personal assistant job interview. There were gorgeous women everywhere waiting for their chance to get the coveted Clarke, Patterson, and Schwartz personal assistant position. I felt awkward and out of place with my black pinstripe skirt and jacket combo. I paired my outfit with black pumps and I had somehow tamed my hair into a business appropriate bun. Luckily, I didn't have enough time to overthink the situation because I was the next to be interviewed. I was called into a midsized office where 3 men and a woman were waiting for me. I felt somewhat uncomfortable under their scrutinizing gazes, each of them analyzing me to find anything wrong or out of place. My interview training kicked in. "Good morning, name is Dawn Hughes," I said as I reached out to shake each of their hands. The introduced themselves as Matthew Clarke, David Patterson, Ted Schwartz, and Veronica Stone. It was then I realized that I was actually interviewing to be the personal assistant of one of the partners. Jesus, I thought it was just going to be some secretarial job. I felt like a minor league player in the starting lineup of the major leagues. The nerves started to kick in immediately. The partners and Ms. Stone, who was the head of human resources, each asked me questions about my background and other personal assistant and secretarial jobs I held in the past. The interview lasted about 30 minutes and I thought it was a homerun. I found out a lot about the partners. Matthew Clarke was all business but also liked to have fun outside the office, David Patterson loved to crack jokes and he had a fiancée who used to be a secretary there, and Ted Schwartz was basically an ass who kept visibly staring at my boobs during the entire interview...I hoped to God that I didn't have to work with him if I got the job. And that was a strong IF. To my surprise, I got the job. Ms. Stone called me the next day to tell me I got the job and that I was a perfect fit for what Mr. Clarke was looking for. I would be starting Monday. It was Monday and I had started my job. I was running around little things here and there. Going downstairs to get copies of this client's paperwork or going out to get coffee for Mr. Clarke. It wasn't boring, I was always doing something. Two weeks into the job and I had gotten everything down to a science, everything came easy. I knew where everything was. I had gotten lost going to the break room 3 times since I had begun working there and I had finally gotten there with no problem 4 times straight. Mr. Clarke had unintentionally made me work through lunch and offered to take me out with him after work. I needed to learn how to relax and have fun, as he put it. I agreed...it's awkward to turn down your boss...especially since it was his first time reaching out to me as his employee. I felt accepted. We went to a nice little jazz spot called Grooves. It was a couple of blocks away from the offices. It was sleek and new age with free form jazz musicians playing on stage. It was a nice place. We sat down in a booth that was close to the stage. "Do you want anything to eat or drink...maybe both?" I checked the menu and decided to go with just a root beer. "A root beer, really? I'm getting a scotch on the rocks...I need to unwind from today's work load." I instantly regretted my decision. "Well, you've been here before right? What's a good drink?" He looked me up and down and studied me intently, which seemed to go on for an hour. I blushed and fidgeted under his intense gaze. He turned away and checked out the menu for a second. "You seem like a mojito kind of girl...you ever had one? Very good." "Ok, I'll take it." He went to the bar to place our drink orders. I looked around the lounge. It was very nice, the crowd was very sophisticated and laid back. Everyone was just there for the music and the atmosphere. I had to tell my friends about this place later. "Here we go, a scotch on the rocks for me and a strawberry mojito for the lady." Matthew, as he begged me to call him, placed my drink in front of me and slid into the booth next to me and smiled. I couldn't help but think about how handsome he was just then. He was a good looking guy; there was no denying that. He had light brown hair, light olive skin, and the deepest blue eyes I had ever seen. He had thick dark lashes that gave him a boyish charm. His chiseled face and masculine jawline complimented each other perfectly. And his thick lips only added to the already complete package. The way the candlelight only succeeded to make him look more tantalizing. My mind imagined what our bodies would look like in the throes of passion... I quickly wiped these thoughts out of my mind...this is my boss...this is my boss...this is my boss. I repeated that phrase over and over to myself almost as if I was programming it into my head. "So, how were your first weeks of work? Not too much work I hope. Last girl ran out in a month." Oh, God... I hope I wasn't in over my head with this job. "Oh, it's been great! I haven't run into any problems yet so it's pretty much been smooth sailing." I sipped on my strawberry mojito...he was right, it seemed like I was a mojito girl. We continued to talk and drank and sampled some of the lounge food...eclectic and delicious. Definitely coming back to this place again. By the end of the night, I had 4 mojitos and I was feeling all 4. I was so embarrassed. First time hanging with the boss and I had gotten drunk. I tried to hide it as much as possible. He paid for everything, which I insisted he let me pay for my drinks and he ardently refused. I was noticeably struggling to put my coat on. Matthew chuckled and held the jacket up while I slid my arms in; trying desperately to hold on to some dignity...I didn't want him to think I was a lightweight when it came to alcohol. I wasn't, I was actually known in college and among my friend as being somewhat of a tank. We went outside and Matthew offered to have his driver drop me off. I didn't want to do that at all. He had taken me out for food and a night cap and paid for everything. Now he wanted to drive me home too? No, I couldn't allow it, I wouldn't allow it. He waved his hand and said it was a "business courtesy". Drunk me considered the statement and deemed it legitimate. We got into his town car and I told his driver me address and we were off. Before I knew it, we had arrived at my apartment. His driver got out and opened the door for me. My brain was so intoxicated I wasn't even on. I slowly slid out of the car and stood and let my legs get accustomed to walking again. Matthew laughed and got out with me. I was puzzled. "What are you doing?" I asked, apparently drunk me had no filter. He blushed a bit then said, "I want to help you get to your apartment...no offense or anything but you look like you're going to need a bit of assistance. Don't worry, this falls under business courtesy." He winked. This made me feel better. We walked up to my building and I punched in the code. The door opened and we took the elevator up to my floor. While we were in the elevator I felt something brush the hem of my skirt. I held my breath. Was he trying to touch my ass on the slide? I pushed these drunken thoughts out of my head...it was probably and accident right? The elevator door opened and we walked down the hall to my door. "Well, this is me." I fumbled with my keys trying to make a dignified escape from the increasing strange situation. "Let me help you with that...." His soft hand guided my hand to the keyhole. I felt his breath on the nape of my neck as he tried to help me open my door. Matthew's body was right up against mine. He was hard! A cold sweat broke out on my forehead. Why was he so close....and aroused? The whole damn hallway was spinning. I needed to get out of there. I quickly turned the key and opened my door. "Thanks for seeing that I got here safely, goodnight Matthew!" He put his foot in the way so I couldn't close the door. "Do you mind if I use the bathroom before I go?" "Well, I was going to actually get ready for bed right now..." That's when I could see him get irritated. "Awwwhhh, c'mon! I rode all the way up here to drop you off...it's a long drive back." He started to push his way in. I was getting scared now. He was getting aggressive and he was so strong. It was only a matter of time before he got in. He slammed his massive frame into the door and it flew open throwing me to the ground. I hit my head on my hardwood floor. Matthew was on me in a flash. He was quick as lightning as he used both hands to yank my white blouse open. Buttons scattered everywhere. My hands flew up to his face in defense. I landed a series of blows before he deftly grabbed my tiny wrists and pinned them over my head using one hand. Using his other hand, he ripped open the front of my black lace bra and began his assault on my breasts. He hovered over my boobs for a second as if to savor the scene and sucked my nipple into his warm mouth. He suckled it and licked the tip slowly and lightly biting it. His other hand gently massaging the other breast. "Please, please, Matthew, stop. This is wrong," I begged. He said nothing and moved toward the other boob. This time his treatment of the nipple was a bit aggressive. Matthew bit the nipple and sucked on it hard. I winced in pain and tried to move my body away from him. He stopped and looked at me intently. Then, he back handed me across the face. As if the throbbing pain from hitting my head wasn't enough, I now had to deal with the blinding pain that radiated from my cheek. I was seeing stars. He continued to bite and lick my boobs until he grew bored with them. He hiked up my skirt and yanked my panties down all with one hand...I wouldn't be surprised if he had done this before. He parted my legs and put his face between my thighs. Ohhhhhh, god he was lapping at my inner folds...my most delicate and private place was on display to this man. He looked up at me from between my legs. Jesus, I have to be dreaming, this has to be a dream. My boss of two weeks had gotten me drunk and now was licking my most intimate area. I was ashamed and I felt stupid for letting myself get so drunk. All I wanted was for him to leave but my body was so weak I could barely move. The assault on my pussy continued. He was more earnest now in his licking and prodding my entrance with his tongue. His tongue was driving deep inside. He was working my body over. Matthew's lips held my clit in place while his tongue did everything it could to bring me pleasure. He sucked on it so hard; I thought I was going to die. He licked and massaged up and down my pink valley giving every inch of my pussy the proper attention of his tongue. It had been so long since a man had touched me like this and so well. But God it was wrong, did he take me being appreciative for going to the lounge as a green light for a quickie? My thoughts were interrupted by a blazing fire deep in my belly. I arched my back and let the orgasm roll through me. I moaned and bit my lip. My body returned to its catatonic state. He hungrily licked his lips and stood up to kiss me. His tongue snaked into my mouth as if to say "look at what I made you do...and you loved it." His kissed me passionately. He then moved between my legs and rubbed his hard shaft over my sensitive clitoris. I started crying then, the realization set in that I was about to be raped and no one was coming to help me. He forced his way in to my tight opening. I could feel every inch of him painfully pushing his way into somewhere he was not invited. I sat up to protest but he shoved me hard back on the floor. He finally spoke, "don't make me hurt you...you'll enjoy this. I promise." This could not be happening! "Please, put a condom on at least," I sobbed. "Condoms aren't my thing...and it's not exactly ladies night, if you know what I mean." He thought that was funny. He started to slowly push in to me. Then pulled out, and slowly back in. He was getting a rhythm going. It started out slowly at first and then he built up power behind his cock. He thought he was a fucking champ. Banging some secretary with no condom...he didn't even have to ask. I hated myself. I closed my eyes and thought about anything but the present. He was really pounding me now. I cried out in pain with each of his frantic thrusts. I wasn't used to his girth and my pussy was sopping wet. Just gushing everywhere. When he slammed his cock inside of me, I could hear and feel the juices going everywhere. In and out in and out. Stroke after stroke, my pussy was expanding and taking more of Matthew's raging bull of a cock inside me. I guess he wanted me to join in on all the fun he was having and he reached down and started massaging my clit. It instantly sprang to life, my body eager to betray me. "Uhhhhh fuckkkk! Are you ready?" He exploded his manly musk inside of my bruised walls. Rope after rope of steamy cum coated my walls while he toyed with my clit. My body shuddered as a tidal wave of pleasure hit me. I moaned and writhed on the floor. He pulled out of my drenched pussy and commanded, "Lick me clean." I laid there in disbelief. He had raped me and now he wanted a blowjob? Matthew was obviously not going to wait for me to refuse. He pulled me up into a kneeling position in front of him and positioned his glistening cock in front of me. He grabbed my hair forcefully, causing me to cry out in pain. He took this opportunity to ram his cock in to the hilt. He groaned in sheer ecstasy at the feeling of my hot mouth encompassing his cock. He took both sides of my head and started to slowly slide his cock in and out of my mouth. I felt like a disgusting sex doll. He was gaining speed and ramming his dick brutally in my throat. I couldn't help but to cough and gag around him. He had his eyes squeezed shut and was moaning audibly now. Without warning, he pulled out of my mouth and ejaculated his hot semen onto my breasts. I was shocked and humiliated...no one had ever done that to me before. I closed my eyes tightly and a dozen hot tears rolled down my cheeks. When I opened my eyes he was watching me...and he smiled and leaned down to kiss me. I turned my head away so fast I thought my neck was going to break. He grabbed the back of my hair holding my head firmly in place. Matthew pulled me up into him and he made out with me. Pushing his lips onto mine, desperate for some kind of pass for the events of that night. But I refused to give him one, he had raped me...plain and simple. He pushed his tongue into my mouth and found mine and messaged it. He finally gave up and removed his tongue. He laughed, got dressed, threw me a towel and said "That was great, I'll see you Monday," and Matthew walked out and left me with my thoughts. I hated what he did to me tonight and I hated that he thought I enjoyed it. But most of all, I hated that he was right. I would see him Monday bright and early with a smile plastered on my face as if nothing happened. I cried myself to sleep. The Diary of a Personal Assistant Ch. 02 The weekend flew by as if nothing had happened to me that passed Friday. On Friday, my boss at my new job offered to take me out for a stress free evening at this hip lounge, Grooves. I had a nice time with my boss and thought that this job would work out well. That was until he forced his way into my apartment and raped me. The worst part about this situation is that I desperately needed this job. I was actually considering biting the bullet and continuing to work there. At least until I found other arrangements. The dreaded Monday morning had arrived and I had to beg myself to get out of bed and get ready for work. I arrived at the offices of Clarke, Patterson, and Schwartz at 8:30 am on the dot. Good, I could camp out in the break room and finish my breakfast before the workday started at 9 am. Apparently, my rapist of a boss, Matthew Clarke had the same plan. He was walking towards where I was standing more preoccupied with whatever he bought from Panera Bread. I wanted nothing more right then to knee him in his crotch and kick him over and over while he writhed in pain on the ground. That thought made me smile a bit. I regained my composure and acted as though I hadn't seen him walking towards the elevators. "Oh, good morning, Ms. Hughes. You're here early." "Good morning, Mr. Clarke. Yes, I had to do some quick filing before the day started," I lied. The elevators door opened and we stepped in. He pushed our floor number and as soon as the doors closed, He turned his full attention to me. His cool facade was left behind in the lobby. "Listen about what happened Friday," he began. I braced myself for an apology. "I hope you understand that whatever goes on outside the workplace, it's best for both parties to keep it separate from work." What was he saying? "I guess what I mean is that if we ever wanted to consider making it a common occurrence, we need to be mature about it and be professional at work. We can't have the partners talking," he chuckled. He was full of shit and I had heard enough. "Hell no I don't want to make my rape a common occurrence! What the hell is wrong with you? Were you not-" He closed the gap between us in the elevator lighting fast stopping me from continuing my train of thought. In an instant, he had dropped his briefcase and Panera bag on the floor. He was now towering over me menacingly. "Let's get one thing straight, Dawn. You were not forced to do anything you didn't want to do as I recall. And as I also recall very clearly, you loved every minute of it. You loved this white cock slamming into you. So if you're thinking about dragging my name through the mud over your dignity, you can forget about it." I was utterly shocked by what he had just said to me. It terrified the hell out of me to see how vicious and cold he had instantly become. I wanted to get out of that elevator. I shrunk back into the corner of the elevator and said nothing. He wasn't letting me off so easy. He followed me into the corner and painfully grabbed a handful of my ass through my pants. I yelped in pain as he roughly squeezed and kneaded the soft flesh. Matthew whispered in my ear, "You know, I can have you anytime. You work for me and whether you want to admit it to yourself or not, you loved me inside of you. You loved taking my cock covered in your juices into your mouth and cleaning me. You loved my seed drenching your milk chocolate tits just as much as I did. Let's be truthful, you want me." I shuddered at his words...I was afraid he was going to take me in the elevator. I swallowed down the lump of fear painfully growing in my throat. He continued to message my ass cheeks and he nuzzled and nibbled on my ear lobe. His other hand slowly ventured under my sweater and deftly slipped under my bra. He fondled my breasts gently and twisted my nipples until they were taut. He moved his hand from my ass to the front of my now damp panties. Matthew caressed my sensitive nub. A small moan escaped from my mouth before I could stop it. He chuckled and started to suck on my neck, feathering kisses from my collarbone. What was I doing? I was letting him have his way with me. He attacked me in my home and I was willingly giving myself to him in my place of business—in the elevator of all places. I had to get away. I pulled away from him and threw myself at the button panel. I pushed a button, any button to escape him. The elevator jerked to a halt and I hurried out without looking back. The rest of the day consisted of me doing as much work as I could. I wanted to leave before Matthew to avoid another perilous elevator situation. I worked through lunch and opted to just eat and work at the same time. I was determined to get out of there early. Matthew came back from his lunch and tossed his coat on my desk sending papers and files every which way. "Take care of that would you?" Then he went inside his office and closed the door behind him before I could utter a word of protest. I was pissed; it would take forever to reorganize. I snatched his jacket from my now cluttered desk and marched in the office. "Since when does my job include hanging up your coat? I have never done it since I started working here." Without looking up from his computer, he said, "Well now is as good a time as any. Think of it as a new responsibility being awarded to you. You're a great employee and I'm giving you more responsibilities around here. And here's another one, I'm going to need you to work overtime with me tonight. I have to put together a presentation tomorrow for one of our big clients. It has to be spotless so I could use a second pair of eyes." The thought of staying here alone with Matthew tonight shook me to the core. I nodded my head numbly and turned to walked out of his office as he added: "Oh by the way, he faxed more documents over to add to his account portfolio. Can you get them downstairs and bring them to me?" I left his office to retrieve the files from the fax machine. Maybe tonight wouldn't be so bad. After all he was being very business-like and he needed to complete and perfect the presentation so there shouldn't be anything to worry about right? I got the new documents and brought them back upstairs. I knocked on Matthew's door and entered. "Mr. Clarke, I have the documents you wanted." He looked up from his computer. "It's quiet. Has the entire office left?" "Yes, I believe so. I didn't see anyone when I went to go and get the files." He then stood up and walked over to me. He took the files out of my hand and tossed them on the floor. He pulled me into his strong embrace. His kiss was passionate and urgent. It seemed to go on for hours. I pushed against his chest, trying to get some space between us. But it was no use, he was as twice as strong as me. He finally broke the kiss. "There is no presentation tomorrow. I can't stop thinking about you or your luscious body for that matter. You make me crazy." His breath was ragged as he leaned his forehead against mine. My head was spinning. I was so angry, confused, and turned on at the same time. I didn't want to become his little office slut. At the same time, I yearned for the way he touched me. He brought me more pleasure than any man had. "I don't want to do this, Matthew. Please, we can go on as if the past couple of days hadn't happened. I don't need complications in this job. I need this job too much." I wanted him to be reasonable. He reached up and pulled the pins out of my hair that held it in a tight bun, ignoring my plea. My silky black hair fell gracefully down to my shoulders. He ran his fingers slowly through my hair, relishing the feeling. "I promise you that this will not be something you will ever regret." He sounded so sincere and trustworthy. I let him take me by the hand and lead me to the couch he had in the corner. He started to remove his clothes: tie, shirt, pants, and finally his underwear. I followed suit. He took my body in, slowly moving his gaze over every inch of my naked body. I blushed under his intensity. He laid me down on the couch. He knelt down between my thighs and tenderly spread my lips apart with his fingers. I shuddered at his touch as butterflies fluttered in my stomach, awakening my desire for my boss. Matthew closed his eyes and inhaled my arousal. He looked up at me and said, "Tell me you want me." Then he blew on my throbbing nub. My toes curled and I arched my back in utter delight. "I want you," I said breathlessly. That was all the encouragement he needed from me as he dove down into my pink folds. He slid his tongue up and down my slit and finally pushed his way into my dewy opening. I threw my head back and moaned, pleasure rippling through my body. His skillful tongue worked its way in and out of me building tempo with each thrust. His tongue would momentarily exit to give my clit the attention it deserved. He used the tip to trace lazy circles around it, teasing me until I couldn't take anymore. I was thrashing around on the couch and crying out for relief. He sucked my engorged numb into his warm awaiting mouth and my orgasm hit hard. My thighs clamped around his head and I almost screamed as waves of pleasure washed over me. I slumped back on to the couch with tiny beads of sweat forming on my forehead. He positioned his ever ready cock at my slick opening and eased his way in, determined to feel every inch of his manhood. Once he was all the way in, he pulled slowly out. Matthew pushed himself in a bit more eager to feel me adjusting to his size. He grabbed onto my hips and started to pick up speed, his balls slapping my ass. My pussy was making slurping and squishing noises every time he slammed his meat into me. My juices were forming a puddle on the couch but I didn't care. I was getting the best fucking of my life from my boss. I wrapped my legs around his waist and he took the initiative to beat the pussy up! He drove himself relentlessly into me grunting and groaning. I screamed and moaned aloud. "Fuck me! Harder, harder!" I egged him on; I was totally lost in my sexual euphoria. The eyes were rolling in the back of my head. "Yeah, ohhh fuck yeah! Fuck, you want me to bury this in your cunt? Shit, I'm gonna ruin you. Ughhhh, ohhh fuck, I'm fucking coming in you!" He slapped my ass and surged forward one last time before he fired off load after load of cum in me. I was right behind him. My hands grabbing the couch cushion as another powerful orgasm knocked the wind out of me. He collapsed on top of me and held me in an embrace. Our breathing slowed and we just lay there, sweaty. Then he moved his hands down and cupped my face and kissed my lips softly. He brushed the hair out of my face and smiled. "Want to go again?" I laughed and propped myself up on my elbow. "Yeah, but I want to be on top this time." He held on to my hips and rolled over. I was straddling his waist and he was laying on the couch ready for me. We kept having sex for another 3 hours blissfully unaware that Ted Schwartz, one of the partners, was listening to our sex session the whole time.