Disclaimers: As usual, any and all people partaking in sexy stuff, are 18 or older. If you think you know any of my characters, let me tell you right up front, you don't. This story is 100% fictional. This might be the most different type of story I've written, so bear with me. Also, this could fit in several different categories, and has two distinct parts. One, a very lighthearted mature story, and the other, a fairly serious romance story.
Let's see, where do I start? I'm Cooper Donaldson. Graduating from Seattle U, with a degree in Business & Finance, just a few months ago, I started working with a medium sized accounting firm, starting in the financial planning department. I just took my place in this department of nearly twenty people, with me at the very bottom of the ladder.
I figured at nearly twenty-three years of age, I could really learn quite a great deal in this area.
I just kept my head down, and my nose to the grindstone, absorbing every bit of information I could.
All this work, left me a minimum of time for a social life. I did have a pair of girlfriends in college, but neither of them were much more than short term flings. I did find out more than a little about sex, after growing up in a very conservative household in Leavenworth, Washington.
Our little city, about two and a half hours north east of Seattle, noted for their Christmas celebrations that ran the entire month of December. Located in the Cascade mountains, we were a tourist attraction, with visitors from all over the country. During December, our population of 2,500, could swell to well over 15,000, most every weekend.
If it was up to my parents, neither my older sister nor I would have ever learned anything about sex. What little we both learned came from our town library.
It took until my second year at Seattle U, that I lost my virginity, to my first girlfriend. Believe me, it was nothing to write home about. At least these sexual encounters didn't leave me scarred for life.
I did meet a few of our clients, just observing the more senior members of our firm. One in particular, I had heard could be a real piece of work. Mildred Harris, a widow, in her late sixties, to early seventies, and quite wealthy. I also overheard some of my colleagues saying Mrs. Harris was a bit on the eccentric side.
Even though I never had direct contact with this lady, I had seen her coming and going from our offices. All I could tell, she was on the short side, and always dressed impeccably. I also noticed she didn't look her age.
Once or twice, I would see her coming or going, and noticed her looking my way, and smiling.
I soon learned that every April first, one of our planners would visit her for a day, or two, seeing if any changes needed to be made in her sizeable portfolio.
It must have been the last week in March, when my boss called me into his office.
When I sat down, he handed me a fairly thick folder, and told me to review its contents, and to come back, after lunch. It took me over an hour to get through all of Mrs. Harris' investments. Whatever her husband did, he did very, very well. I was truly impressed.
When I finished, I started thinking, why on earth did I get this folder? Did they really trust me enough to give this lady any guidance with her family fortune? Or, was I being punished, for some unknown reason?
Come on, Coop, don't overthink this, I said to myself.
After lunch, I went back to my boss' office, and was told that I'd be assisting this wealthy, old lady, and to be at her house by 9:00 AM, sharp, Friday morning.
Wow! Either I truly fucked up and am being punished, or they really trusted me to assist with this most valuable client.
As I was leaving work on Thursday afternoon, several of the older men in my department told me to keep a smile on my face, and remember to be courteous.
I had no idea what this little adventure would entail, but I knew if I did well, it would put me in a good light, at work.
I knew a little about the neighborhood Mrs. Harris lived in, but what I had heard, didn't do her house justice. I knew this area was 'old money'. Driving up her driveway, my mouth must have been hanging open.
In front of me was an estate, not just a house. Sitting on nearly a full acre, with a view of downtown Seattle, plus, the Olympic Mountains off to the west, this place was magnificent.
I was guessing this house was probably a hundred years old, and more than likely close to eight or nine thousand square feet.
When I rang the doorbell, I almost expected a butler to answer, but through an intercom, I heard, "is that Mr. Donaldson?"
When I answered, yes, the door unlocked, and I entered. I just stood in the entryway, gaping at the artwork on the walls, and the marble floors.
"Don't just stand there, come straight ahead, into the study", she ordered.
I thought to myself, this is going to be a long day.
Entering the study, I saw Mrs. Harris, dressed as if she was going to the opera. Extremely fancy clothes, jewelry that I could only dream about, but with a welcoming smile.
"Good morning, Mrs. Harris", I said.
"OK, lets get one thing straight, I'm Mildred, and if you're nice, I might let you call me Millie, got that?" She did end this with a broad grin.
"Fine by me, so please call me Coop," I replied.
"Coffee, or tea?"
"Coffee, black, please."
Again, I expected to see servants, waiting on us, but she made me a cup and we sat at what I assumed was her late husband's desk.
"Before we get started, Coop, I want anything you're going to explain to me, done in language I can understand. And, let me be clear, don't try to bullshit me, I'm too smart to be snowed."
To say I was stunned at her language was an understatement.
I just grinned, and told her I wouldn't think of doing that.
As I started getting out the reports and spreadsheets, and placing them on the desk, facing her, she just sat there, smiling at me.
I did take notice of her striking good looks. She did not look her age, which I knew was nearly seventy years old. Yes, her face had lines, but still she looked like the beauty she was in her younger days.
After nearly an hour of going over how her investments were doing, she quietly asked if I had a girlfriend.
"Not at this time, Mildred," I answered with my cheeks turning a little red.
As we continued, she moved a bit closer, saying she wanted to look at a particular file. I felt her shoulder against mine, but thought she was just getting a closer look.
"You're a very good looking, young man, Coop. I hope its OK for me to say that."
"Yes, and thank you. You're a striking woman, Mildred."
She just smiled, and went back to reading the reports. After a few questions, she told me to relax, that lunch would be ready in a short while. She told me I could look around her house and gardens, if I wanted.
As I was walking around the grounds in back of her house, I happened to glance back, and saw her near a window on the second floor. I didn't want to stare, but the blouse she was now wearing looked nearly transparent in the reflection of the glass.
I quickly looked away, not wanting to be thought of as a peeping Tom.
Heading back towards the house, Mildred appeared with a tray of sandwiches and a pitcher of lemonade.
"It's so nice, today, lets eat outside."
As I nodded my approval, I took another look at her blouse, and, yes it was nearly see-through. I nearly choked when I saw her nipples fully erect. I knew it wasn't cold, so I wondered why she was so excited.
"Am I embarrassing you, dear boy?"
"Um, not really, just a bit surprised."
"Surprised that I just might be excited, or that my nipples are on display?"
