New Assistant

This is the first in what should be a series. i hope you enjoy. As always, I enjoy feedback so please feel free to rate, comment or message!

*****

Over my corporate career I have discovered that there are certain milestones that you pass. I started my first job at 22 and had spent twenty one years slowly, but steadily climbing up the ladder. I began in a small shared cubicle, then earned my own. As the team I supervised grew, I eventually earned an office, then finally, one of the corner offices with the windows that wrapped around.

My company was a bit old fashioned. Most other organisations had gotten rid of most offices or made them out of glass, preferring a more open layout. Here, however, they kept to the more traditional layout with cubicles on the lower floors and executives in larger offices on the upper levels. Outside of each office was a small desk where an executive assistant would sit.

I was pretty proud of myself for having achieved all of this. I grew up a small town kid, smart but a bit awkward. As I moved the last of my stuff into the large space on the 35th floor of a 38 story building, I felt like I had finally made it.

It had not been overnight. Some of my colleagues were a fair bit younger, kids who grew up rich with all the right connections. That was not me. I was 43, and I had fought the trust fund babies all my career, crushing them and stepping over them, step by step all leading towards here, Senior Vice President of the Eastern Division.

I sat down in the large, super ergonomic chair that was behind my wood desk, and leaned back, savouring the moment. The company was traditional in the office design as well as the layout. Behind me I had two walls of windows that gave a panoramic view of the city and let in light. My desk was large and wooden, with the front going down to the floor. I had two comfortable leather chairs facing my desk and a leather couch and a coffee table on the side of the room. There were bookcases on the walls that weren't all windows but they were mostly empty. I knew I would fill them eventually.

I walked to the tall mirror on the wall beside a coat rack and looked at myself. I had held up pretty well over the years, I thought. I was 5'10, my hair was blond, and cut short. I ran my fingers through it. It was a bit thin, but still there. My light blue eyes regarded myself above my full trimmed beard. I was wearing a blue suit with a white shirt and dark blue tie. I ran most mornings so I was in pretty good shape. I was pretty pleased with myself at that moment.

I straightened my tie with my left hand and glanced at the simple gold band that I wore there. It reminded me that I had promised to call my wife later and let her know how my day was going.

My self reflection was interrupted by a knock at my door. I called out for the person to enter, looked over and saw a young woman standing there.

She was beautiful. That was my first impression. Her auburn hair was pulled back in a tight, professional looking bun, with only a single strand loose, hanging over her cheek. Her face was oval, behind heavy black framed glasses, her nose was small with brown freckles across the bridge and her cheeks. Her lips, plump without looking fake, were painted with a subtle color.

I could not stop my eyes as they wandered down her body. She was wearing a black and white striped sweater with a neckline that cut down in a V. It was professional looking but I caught a small glimpse of cleavage. The sweater was large enough to mask her true bust size but I got the impression that her breasts were quite large. She had on a black skirt that came to mid thigh and hugged her hips, and presumably her ass, quite nicely. Her legs were clad in dark stockings and had cute, anklet boots with a short heel on her feet. I guessed her height was somewhere around 5'4, 5'5.

I shook my head, hoping that I had not been ogling her for too long. That was the last thing I needed. An HR complaint on my first day in my new role.

"Um," I said, a bit confused as to why she was there. "Hi? Can I help you?"

"Are you Brian Whitecastle," she asked.

I nodded. That was, indeed, my name. Her voice was a bit husky, something I had always found sexy in a woman.

"Great," she said. "I'm Tara, your new executive assistant. Very nice to meet you."

I was very confused. I had interviewed a dozen candidates for the role of executive assistant, and had hired a young man named Pete. This was clearly not him.

"I think there has been a mix up," I said. "No offence, but I didn't hire you. I don't think I even interviewed you?"

"I don't know anything about that, sir," she said. "I was just told by HR yesterday to report here this morning to help you get set up and take on the assistant duties. So, is there anything you need? I'm already working on your schedule and will have that done in about half an hour. Would you like a cup of coffee?"

"Sure," I said, still a bit flummoxed. "I'll take a coffee. Black."

She turned and left the room and shut the door behind her.

I reached for my phone and punched in the extension for the woman I knew in HR.

"Mandy," I said when she answered. "How are you?"

"I'm good, Brian," she replied. I had always liked her. She was in her thirties and quite pretty. Occasionally we would flirt a bit at office parties. "How are you settling in? It's pretty early on your first day to be calling HR. Did you just want to chat with me?"

"As much as I love talking to you," I said, chuckling, "I'm a bit confused. There is a girl here. Tara I think she said her name was, and she says she's my assistant? I thought I hired Pete."

"Oh," Mandy said, "did I forget to include you on the email chain? Damn. I'm sorry. Pete had a family incident so he can't start work for a few months. I had to find a replacement quick and Tara's old boss, you know Mike? From finance? He retired. So I transferred her to you. You'll love her. She's great at her job!"

"Oh," I said. "Damn. I liked Pete. I hope he's ok. But what about the others I interviewed? I kind of wanted to build my own team."

"She was the best I could do at short notice and I really need to place her somewhere. Don't worry. I think you will like her a lot. And if she doesn't work out, come to me in a few weeks and we will figure something out."

I sighed. I did not really like having someone thrust on me like this with no notice.

"Ok," I said. "I'll give her two weeks, but likely I'll want to hire my own."

"Ok, Brian," Mandy said. "Sounds good. Look, I have a meeting, so I have to go. Follow up in a couple weeks. Bye!"

I sat back and hung up the phone. I shook my head and placed my laptop on my desk, opening my email.

Tara returned a few minutes later with my coffee. I glanced up at her, thanked her and took a sip. My eyes widened. This was the best cup of coffee I had ever had in the office.

"That's really great," I said.

"I bring my own beans from home. I'm glad you like it," she said smiling. She had dimples when she smiled, I noticed.

"Oh," I said, unable to stop myself from smiling back. "Don't waste the good stuff on me."

She laughed.

"Only the best for you, sir. I take pride in my job, and my job is to make your life easier and better. So, shall we go over your schedule? I have today done and am working on the week, but need some feedback."

She walked around the desk and looked over my shoulder, leaning forward, hand palm down on the desk beside me. I couldn't help but notice that she was very close to me. I could smell a faint flowery perfume wafting from her. Her sweater fell forward a bit, a gap between the knitted fabric and her body forming and I couldn't help but steal a glimpse.

I saw more cleavage, and freckles across the tops of her breasts and collarbone, and just the edge of a white bra. I quickly flicked my eyes away to my laptop screen, hoping she hadn't noticed.

For years I had shared an assistant with other managers, and that meant I had to do a lot of these types of things on my own. It was new to me to see my day perfectly laid out without having to do anything.

It all looked very good. My morning was blocked off for review of documents that I would need to understand for my new role, and the afternoon was mostly taken up with a staff meeting with my team. Introducing myself and setting expectations.

"What's this purple time here," I said, pointing at the time block between 1pm and 2:30.

"Oh," she said. "That's for your lunch break."

I shook my head.

"That's too long," I said. "I usually take around 15 minutes. An hour and a half isn't necessary."

"I think you will find it is, sir," she said, almost firmly. As if she knew better than I did. "You will often have lunch meetings that will take at least that long. Also, most upper management takes at least that much time. If they find out you aren't, they might resent you for making them look bad."

I sighed. There were obviously office politics that I didn't fully understand going on. I moved on the rest of the week, requesting some adjustments, and after a bit we had it all figured out.

"Well," I said. "I guess this looks good. I'm going to read some of this." I tapped the pile of papers beside me.

"Good," she said. "You will find my summaries on top of each file with all of the pertinent points laid out. And post-it arrows pointing at all of the sections I believe are worth reading deeper yourself."

I raised my eyebrows.

"When did you have time to do all of that?" I asked, surprised. It must have taken hours.

"Oh," she said, and smiled shyly. "I wanted to be ready for today so I worked on it last night. It's just me at home, so I guess I had time."

I was surprised to know that it was just her. I had assumed she must be married or with a live-in boyfriend. She seemed like someone that would be locked down.

"Ok," I said. "I appreciate it, but please don't burn yourself out for me. I'm pretty independent."

"Just part of my job, sir," she said. "I'll be just outside at my desk. Buzz if you need anything. I'll close the door behind me."

"You can leave it open," I said.

"Most people close them sir," she said. "For privacy when you get calls and stuff."

She left and closed the door behind her.

Her summaries, it turned out, were perfect. She was clearly good at her job with a sharp mind. She caught aspects of the documents that I might have missed if it wasn't for her work. I carefully read the first few documents thoughtfully just to be sure, but soon realised that I could rely on her notes. It made the work go much faster.

Soon it was one PM and I heard a knock on my door.

"Come in," I called out and Tara entered.

"What would you like me to order you for lunch," she asked. "I'm sorry I should have asked earlier."

In the past I had seen the parade of nice meals heading up the elevator to the executive levels and had always been a bit jealous. It had not occurred to me until just now that I was now privy to all that.

"I hadn't thought about it," I said. "I guess I could go with a burger. What are you having?"

"A salad today, I think," Tara said. "I made one this morning."

"Did you want to eat in here with me?" I asked. Then frowned. Wait. Maybe she wouldn't want to spend her time with her boss. "Only if you want to of course. I'm just not used to eating alone."

"Of course, sir," she said. "I'll bring it in when it arrives."

"You don't have to call me sir," I said. "Brian is fine."

"That's ok, sir," she replied. "If you don't mind I'd prefer to call you sir. I like calling a man Sir."

She turned and walked out of my office. It seemed like she blushed a bit when she said that, but I dismissed that as just my imagination. I could not ignore that hearing her say that made me... feel a certain way. I licked my lips but then shook my head. I was reading into her statement things I was sure she did not intend.

I felt a pant of guilt and picked up my phone, dialling my wife's work number.

"Brian," she said, picking up on the other end of the line. "How's it going? How is your first day?"

"Pretty good Janice," I said smiling. My wife was very proud of me and my success. "I think I'm settling in. I guess I will find out as time goes by. How about you? How's work?"

Janice was a social worker, working for the city. It was a thankless job, and it took a lot out of her. To her credit she had not become jaded and still enjoyed helping the people she could.

"Not bad," she said. "Same as usual. How is that new guy, Pete, working out? What's it like having an assistant?"

"Funny thing," I said. "Well not funny. I guess he had a family thing and can't work for me anymore. They gave me a different one. Her name is Tara. I think she might be better than he was anyway, so it might work out. I'm trying her out for a bit."

"Oh," Janice said. "That's too bad for him. I know you were looking forward to working with him. What's she like?"

"She seems very competent," I replied. "We will see, I guess."

There was a pause.

"Is she pretty?" Janice asked. It sounded like she was teasing but I had no intention of falling into any kind of trap. Normally Janice was not a jealous woman but she occasionally had her moments.

"Yes," I said honestly. There was every chance the two would meet and it wouldn't help me to lie now and get caught out about it later. "I guess she is. Young, though. I'm thinking mid twenties? Seems good at her job though."

"Ok," Janice said and then laughed. "Well don't get caught checking her out. We don't live in a world where you can get away with that anymore, thank god."

"I know," I said laughing along with her. No jealous crisis here, I realised and felt better. "One wrong move and I'll be 'Me Tooed' right out of the building."

"And you should be," Janice said. "If you were to act like that. But I know you. I'm sure you will be good. Anyway, are we still on for supper tonight to celebrate?"

"We sure are," I said.

Tara knocked on my door just then and came in carrying takeout bags. I gestured for her to place them on the desk.

"Ok," I said. "I have to go. My lunch is here. Love you."

"Love you too," Janice said and hung up.

Tara and I cleared the desk and spread our lunch out.

"Was that your wife," she asked.

"Yeah. Janice," I said. "We are going out to Hank's Steakhouse for supper tonight to celebrate the promotion."

Tara nodded.

"I think I can do better than that, if you want," she said. "Nothing wrong with Hank's but I know a girl who works at Maison D's. I could probably get you in.

I raised my eyebrows. Maison D's was one of the hottest French restaurants in the city.

Tara pulled out her cell and made a call. I couldn't help but watch her as I ate. She sat up very straight, but now that she was closer and I had the time I could really check her out. She was not trying to be sexy, I knew, but it oozed off of her. I mentally guessed that her breasts must be D or double D sized, above what looked like a thin waist. Her legs were crossed but that made her skirt ride up a bit, showing me more leg. Her stockings ended high on her thighs but the way she sat I could see the darker edge to the top of them. I couldn't help but wonder what kind of panties she was wearing.

"Done," she said finally, interrupting my examination of her. I quickly averted my eyes, hoping she hadn't noticed. If she did, she said nothing. "Reservations for 7:30. I'll cancel the ones you have at Hank's.

She opened the plastic bin that held her salad and I dug into my burger.

We chatted for the forty minutes I had left in my schedule for lunch and got to know one another a bit.

I learned that she was 24 years old, and had taken some basic business classes, but had found a good paying job as an assistant and dropped out to pursue that. The pay was good and she didn't like school. She was unmarried and did not have a boyfriend. She lived alone in an apartment not far from the office with a cat.

I'm not sure how I even learned all of that. Looking back the conversation seems like a blur. We easily moved from subject to subject.

She learned that I was 43, had been married for 12 years, did not have any kids but did have a dog. I lived in a townhouse downtown, and had been a career corporate worker.

Finally it was time for me to have my staff meeting. I stood up, pulling the napkin out of my collar where I had tucked it to protect my clothing and crossed to the mirror to re-tie the tie I had undone to eat.

I was about done when Tara walked up to me and reached out, grasping the knot and fiddling with it, straightening it. Finally she nodded and placed her hand, palm down on my chest and looked up at me, smiling.

"You look good," she said, her hand lingering there. I was suddenly aware that she was standing rather close. I wasn't sure if I should step back, if I was being inappropriate, or if that would offend or startle her.

The warm hand on my chest felt heavy, but comfortable. I swallowed, suddenly very aware of the woman in the room with me. I could feel my cock starting to get hard, and was worried I would make an ass of myself.

"Thanks," I said, unsure what to say next. "You, you too?"

She chuckled.

"Thank you sir," she said, finally stepping away.

I hurried off to the meeting, trying to subtly adjust the bulge that just standing near Tara had caused in my slacks.

+++++

The meeting had gone well and I left shortly after it was finished. I knew most of my team from previous projects so I knew that I could trust them to do a good job, and they knew that I would be looking out for them.

I drove home, arriving before my wife for once, and took a quick shower and got ready. She arrived shortly after that and soon we were on our way to the best restaurant in the city.

She was wearing a nice dark blue dress that showed off her figure quite nicely. Janice had always taken care of herself, and she looked very good for 39 years old. Her brown hair was done up, rather than the loose style she usually wore. She had a simple silver necklace I had bought her some time ago around her neck, bringing attention to her lovely collarbones. Her breasts were still firm, a nice handful that I loved to explore every chance I got.

I pulled her to me and kissed her, but she pushed me away giggling.

"Don't wreck this makeup," she said, laughing. "I don't wear it often, so it'll take forever to fix.

I had not told Janice about the change in reservations, wanting it to be a surprise, and she squealed happily when we pulled up in front of the place.

"If your assistant can pull this off,"Janice said, "make sure to keep her!"

We had a very nice meal, basking in my success. It was eleven small courses of perfectly cooked french food with the woman I loved. I couldn't imagine a nicer evening. I had to drive home so I only had a couple glasses of wine but Janice got a bit tipsy, before we were done.

I drove us home and we went into the house, up to our bedroom on the third floor. My wife thanked me and wrapped her arms around me, kissing me.

I returned the kiss, my hand sliding up the front of her smooth dress to take her breast in my hand. I ran my thumb across her nipple, pressing my now hard cock against her stomach.

She broke the kiss and stepped away from me.

"I'm sorry, babe," she said. "Do you mind, not tonight? I'm feeling a bit wobbly and we both have to work tomorrow."

I sighed and turned away from her, undressing and getting changed into the pyjama pants and tee shirt that I usually slept in.

"Of course," I said. "If you aren't in the mood, that's fine."

When my wife and I met we had had an amazing love life. We fucked multiple times a week and had not seemed to be able to keep our hands off of one another. Unfortunately as the years had gone by the libido of my wife had plummeted while mine had stayed steady or even increased. It was the one sore spot between us.