Personal Assistant

Derick Holster sat in his office staring blankly at his computer screen. He finds himself doing this often as his mind drifts away thinking about his wife Karen. Derick was a widower after his wife Karen lost her battle with breast cancer the previous year. He often thinks about her straight blonde hair, long eyelashes, and beautiful blue eyes. He and Karen had been soul mates and they spent every moment they could together. He loved her with all his heart. When she was diagnosed with breast cancer, Derick didn't want to believe it, he spent every free moment searching the internet for cures and different doctors that she could visit. Karen, however, seemed to accept her fate, and even though she fought diligently to defeat the disease she also spent the rest of her life living it to the fullest. 

The day before Karen passed, Derick was sitting by her side in the hospital holding her hand as she slept. He was exhausted himself and his body ached for sleep but he refused. He was going to spend every second he could with his beloved Karen. Suddenly he felt a gentle squeeze on his hand. As he looked up he saw Karen looking at him lovingly. 

She whispered in her raspy sick voice "D listen to me (D was her pet name for him), when I'm gone I want you to be happy, I don't want you sulking around for the rest of your life. Live it to the fullest, and don't be alone. There is someone else out there that will love you as I love you." 

Derick thought about her words often. As he sat there at his desk, he thought about trying to date again and quickly dismissed the thought from his mind. For some reason, it still felt like cheating on his wife. In fact, since her passing Derick had not been with a woman sexually and even abstained from self-pleasure. As a man in his late 20s, this took a physical toll on his body and his manhood ached for release. He just couldn't let himself let go, for some reason he felt that since his wife couldn't enjoy such things then he couldn't either. In a way he was punishing himself for a crime he didn't commit, he knew this but for some reason, he just couldn't move past it. 

"Is there anything else you need before I take off for the day?" 

Derick looked up to see Mary, his executive assistant standing at the doorway in his office and then at the clock, 6:30 pm already? 

"Mary, I told you that you can go home at 5:00 with the rest of the staff, you don't have to wait for me," Derick said. 

"Oh, I had to catch up on some data entry that I've been putting off for weeks," she replied. 

Derick knew this was not true, Mary was so devoted to her job that she would often stay at the office whenever he was there just to make sure he had everything he needed. In fact, she often came to his house to help him organize, pack clothes for business trips, and even cook on occasion. 

"You are too good to me Mary, no I'm fine you go home I'll see you tomorrow," he said. 

Mary gave him a little smirk and turned to leave. As she did, Derick noticed how her skirt hugged her hourglass figure and how her long slim legs ended with beautiful red velvet heels on her feet. As his mind started to wander he quickly shook his head back and forth as if to literally shake the thoughts from his brain. 

Mary had been hired by the board of directors after Derick started struggling with the everyday tasks and the responsibilities that were assigned to him. Derick was the CEO of a Fortune 500 company, in fact, he was one of the youngest CEOs ever appointed to a publicly-traded company worth over 500 million dollars and he was good at his job.  His staff loved him and was able to increase company profits by 80% year over year, but he always struggled with mundane tasks such as answering emails, signing paperwork, and preparing for business trips. When the board ordered him to take on an assistant, Derick resisted, he had never needed an assistant before and he had gotten that far. But after a while, he relented and promised to hire an executive assistant to help him out. After 3 months without interviewing a single applicant, the board took it upon themselves to hire Mary. 

When Derick first met Mary he immediately noticed her beauty. She was about five foot five inches tall, slim waist with round rump and decent sized breasts. She had long brown hair and brown eyes. The woman could have been a supermodel. Maybe this was the reason he was apprehensive at having her be his assistant at first. Surely a woman this beautiful couldn't be a good assistant as well. He was wrong. Mary was a fantastic assistant. She had the ability to see what Derick needed before he knew it himself. One time as he was meeting with an important client he had clumsily spilled his coffee cup onto his dress shirt and slacks. His entire outfit was completely saturated with dark brown coffee. As he walked out of the conference room and notified Mary of what had happened, she quickly opened the bottom drawer of her desk and took out a small duffle bag, and handed it to Derick. 

"What is this?" He asked as he took the bag from her. 

"Dress shirt, slacks, necktie, and underwear, go change in your office" she replied. 

Mary had anticipated that something like this might happen and had prepared ahead of time. What was even more amazing is that she had bought all the clothes in the correct size and even knew the type of underwear that he liked. Yes, Mary was truly amazing. 

An hour had passed since Mary had left and Derick decided it was time to go home. As he walked out of his office and passed Mary's desk he noticed that she had left her wallet on the floor next to her desk chair. 

"It must have fallen out of her purse as she picked it up to leave," he thought. 

Mary liked to stop at Starbucks every morning before coming into work and he knew she wouldn't notice the missing wallet until she went to pay for her morning chai tea latte. Derick decided he would drop it by her apartment on the way home. He had been there once before to deliver a get-well card and flowers when she was out for a week to have her appendix taken out, so he knew where she lived. 

Hoping it wouldn't be weird if he just stopped by, he grabbed her wallet and headed out. 

Derick hesitantly knocked on her door with the wallet in hand. 

"Derick?" She exclaimed as she opened the door "is everything all right?." 

"Yes, you left your wallet on your desk and I wanted to return it to you, I knew you would be upset if you couldn't buy your morning chai tea latte," he said. 

"Oh thank you so much!" She replied as she took the wallet. "I just finished making some dinner and have way too much, join me." 

"No, I couldn't" he replied, "you have spent enough time assisting me today." 

"Derick, get in here and have some dinner, it's orange chicken and fried rice, one of your favorites." Boy, she really did know him well. 

"Well if you insist" Derick replied. 

"I insist", she said as she smiled at him and opened the door wider to let him in. 

As she did, Derick noticed that she was wearing shorts that ended at her upper thighs and a midriff tank top with no bra. Her nipples were gently poking through the thin shirt and he could make out every curve of her perfect body. As he looked up he noticed Mary was grinning at him, "did she just catch me checking her out?" He thought. If she did, she didn't seem to mind. 

Mary led Derick to the table and served him the Chinese food with a glass of wine. As they ate, Mary told him about her childhood, and how she left a promising career as a model to become a businesswoman and personal assistant. Derick was fascinated with her life, and their conversation continued for hours. 

As they were sitting on the couch, the conversation turned to relationships. Mary explained that she hadn't had a serious relationship for 2 years when she had suddenly come home to find her boyfriend sleeping with her sister. 

"You have to be kidding, that's the type of stuff you see in movies" Derick exclaimed. 

"Unfortunately I'm not" she replied. "I haven't talked to my sister or to Steve since that day." 

"I'm so sorry Mary," Derick said. 

"What about you?" She asked. "Have you dated anyone since Karen passed?" 

"No, it just never seemed right you know?" He replied. 

"D, you know Karen would want you to move on" 

Hearing her call him D reminded him of that day Karen had asked him to move on. Derick looked at Karen's eyes and saw something else in her. He saw someone who cared and loved him, the type of person that Karen had told him to find. 

"Yes, I suppose you are right," Derick said as their eyes locked.

"So you haven't been with a woman at all? Not even a one-night stand?" 

"No, I haven't even masturbated," Derick replied. Why was he being so honest with her? Was it the wine?

"You're kidding me?" She asked. Not even once?

"Not even once"

"Wow, no wonder you're so wound up," she said, jokingly. 

Derick chuckled, "yeah that probably has something to do with it."

"Do your balls ache?" She asked with a wince.

"Ha! Yes, a lot of the time they do. Especially when I see you answer the door with that tank top and shorts." He said with a grin. 

Mary blushed and said, "you know D, I am your assistant and it's my job to assist you in any way that you require." As she said this Mary put down her glass of wine and slowly crossed the couch and leaned over Derick's body. Their lips are inches from each other. Derick felt like his heart was going to beat out of his chest. As Mary leaned in for a kiss she could feel his rock-hard cock press against her belly. Finally, their lips touched and Derick let himself truly kiss this amazing woman. 

As they started making out on the couch, Mary flung her top over her head and Derick got his first look at her breasts. They were as perfect as the rest of her body. Round with perfectly shaped and colored nipples. Derick guessed they were about a C cup as he slowly caressed them and kissed her hard nipples. Mary then unbuttoned Derick's shirt and removed it, throwing it to the floor. She then released his belt buckle and removed his pants and underwear freeing his stiff cock. She started kissing down the front of his chest, across his belly, and down to his member. She gently kissed the head, then moved down the shaft and took one of his testicles into her mouth. Derick moaned with delight. 

"Oh, Mary" he exclaimed as he threw his head back in delight.

"Mmm, you like that?" She asked.

"Yes, I won't be able to last long" he replied. 

"Oh I know," she said as she put her mouth over the head of Dericks cock and started stroking his cock with her mouth and tongue. Mary could sense that Derick was about to cum and removed his cock from her mouth. 

"Sorry, not yet D. It's my turn" Mary stood up and pulled down her shorts. To Derick's surprise, she wasn't wearing any underwear. He got his first look at her perfectly shaped pussy. Mary had obviously waxed recently as there wasn't a sign of hair anywhere. As he looked at her his cock started pulsing with desire. 

Mary laid back on the couch and spread her legs. Derick slowly leaned forward and put his face near her wet slit and softly licked it. Mary moaned with delight as he continued to devour her pussy with his tongue. After a few minutes of this and Mary started convulsing with desire and orgasm. 

"Fuck me D" she screamed.

Derick obeyed and gently inserted his cock into her tight pussy lips. He started slowly pumping in and out, picking up the rhythm as he continued. Faster and faster Derick fucked Mary until he could no longer hold back. 

"I'm cumming" he shouted as he pulled out of her pussy and squirted his thick white cum across her body, face, and hair. Derick never had such a hard and satisfying orgasm in his life. 

He laid back on the couch, breathing deeply and smiling from ear to ear.

"There you go, don't you feel better now?" Mary said smiling as she wiped the cum from her face with the back of her hand. 

"Mary, that was amazing. I never thought I could feel this way for another woman since Karen." He said as he looked her in the eyes. "You take such good care of me, I love you, Mary."

"I love you too," Mary said as she blushed with excitement. "Now let's go take a shower together, drink some more wine and do that again." 

"Sounds like a good plan to me" Derick replied as he stood up and reached his hand out to Mary. "I think the office could do without both of us tomorrow." 

Mary smiled, took his hand, and stood up. Derick grabbed the small of her back and brought her in for a passionate kiss.