My Wonderful Weekend

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?"

"Both, I guess."

Smiling, we started eating this lunch that magically appeared.

Just making small talk, while we ate, she literally knocked my socks off, when we finished.

Moving around the table, she sat in my lap, laying her head on my shoulder.

"Please, just hold me, Coop, I haven't been held by a man in some time."

I just looked her in her piercing, dark blue eyes, and lightly kissed her lips.

"If I didn't know better, young man, I'd think you were trying to put a move on me."

Smiling, I leaned over and kissed her again. This time, a little deeper. She gripped me around my neck and kissed both my cheeks, and started nibbling on my neck.

"Who's putting the move on who, Millie?"

Without saying a word, she sat up and starting unbuttoning her blouse.

"Should we go inside?"

Silently, she removed her blouse, letting me have a glimpse of her breasts. Not all that big, but having four children, coupled with her age, they did have some sagging. The thing that caught my eye, was the size of her nipples. It wasn't cold, but they stood out nearly an inch.

"Does my body look OK?"

"Absolutely beautiful."

She moved onto my lap, facing me, and kissed me with a little more urgency. I decided to get brave, and tried pushing my tongue into her mouth.

Her eyes shot open, but she slowly opened her mouth, allowing my tongue entrance.

I moved one hand down, cupping her already aroused breast, feeling just how hard her nipple was.

"Now, I think it best to go inside, my dear."

Picking her up in my arms, we headed inside. She nodded towards the stairway, and up we went.

Finding the master bedroom, I gently set her on the bed, laying down, next to her. I leaned over, softly licking one very erect nipple. Just hearing her soft moans, I was fairly certain where this was leading.

When she whispered to me that I was a bit overdressed, I got up and started undressing.

Now I don't claim to be in the body builder class, but at just over six feet and a fairly solid 180, I guess I looked pretty good.

I unbuckled my pants, letting them fall to the floor, showing my already growing bulge in my briefs. Seeing the look on her face, let me know that she was anticipating my briefs being removed.

When they hit the ground, her eyes opened very wide.

"You have to be very gentle, my dear, its been a long time, and that's quite a bit bigger than what I was used to."

Moving next to her, and kissing each nipple, my hand moved to between her thighs. With just the tip of one finger, I slowly rubbed up and down her very puffy lips. With a very hard nipple in my mouth, I gently pushed one finger into her sacred spot.

I knew by her body movements, and her moaning, I was on the right track. My finger pushed in farther, as I moved between her open thighs. Moving my solid seven inches up and down her pussy lips, I eased my way inside.

The look in her eyes was priceless. Sheer excitement. Her hips started to slowly respond, as I picked up my pace, just a bit.

She grabbed my face and kissed me for all she was worth. She wrapped her legs around my backside, as my pace quickened. Now we were really getting into the theme of things.

She must have had two or three orgasms, when I finally exploded, deep inside of her.

"Oh, Jesus Christ, Coop, it feels like a fire hose went off inside of me. Can you help me up, please, I don't want to fall over."

While she was cleaning up, I did the same, as she stared at me and commented that I was still hard.

"Shall we lay down and just cuddle, Millie?" I asked.

"Only if you can behave yourself."

Laying back on her bed, with her cuddled right next to me, I could still feel her body shaking, just a little bit.

Seeing my cock at nearly full mast, again, she just gave me a 'are you kidding me' look.

Giving her a very soft kiss, I silently moved down her body, kissing her every few inches. As I neared the junction of her thighs, I heard a very quiet, "I've never done this before."

When my tongue found her very puffy outer lips, she let out a little scream. Along with her putting her hands on the back of my head, I knew I had permission to continue.

Finding her throbbing clit, I very lightly took it between my teeth, as another orgasm shook her body. Licking up and down her pussy, I moved back putting my cock back inside. After a few minutes, I made the brash suggestion we roll over, and for her to get on top.

You'd think I'd have asked her to fly to the moon, but as soon as I positioned her on my manhood, she leaned over, allowing we access to her swaying breasts.

Catching one nipple at a time, I kept up my pace, as both her moaning and body shaking were keeping pace with my fucking. Just as she collapsed on top of me, I shot stream after stream of cum deep in her interior.

"Oh my God, Coop, just hold me, I can't move."

As she caught her breath, she actually apologized for dripping on me.

"I think all this fucking is for the young kids, Cooper!"

"You're only as old as you feel, my sweet Mildred."

"Are you serious, telling me my body is OK with you?"

"Millie, seriously, do you think I'd get this excited if your body didn't turn me on?"

I then made the suggestion that really had her wondering if I had a screw loose.

I invited her to take a shower with me, as we both were drenched in sweat, plus my second dose of cum.

"Are you kidding me?"

"Nope, come on, I'll lead the way."

Carrying her into her bathroom, she started the shower, and in we went. I washed her as gently as I could, making sure I had a hold, so she wouldn't fall.

While soaping her breasts, her nipples were like granite. Her hand was behind her, taking hold of my cock, and softly moving back and forth.

As it got back to full strength, it touched her tender rear end.

"Not a chance in Hell, cowboy," she gasped.

I turned her around, put both my arms under her legs, tucking them around my sides, and started slowly moving in and out of her very wet cunt.

"Easy, Coop, I'm a bit out of shape, down there, so just go really slow. Oh, shit that feels so fucking good."

Slowly, I started in and out, holding her body as close to mine as possible. Her grip on my shoulders became more intense as she was starting to shake, even a little harder. When I finally shot my load into her sopping wet cunt, she could barely hang on to me. I had a hold on her, tight enough to make sure she wouldn't fall.

After drying off, and laying next to each other, in bed, she just kept looking at me and quietly asked if I had any regrets over these past three or four hours.

"Do you think for one minute, Millie, that I would have been able to do the things we've done, if I didn't thoroughly enjoy myself?"

"Just checking, my dear Coop, just checking."

It took us both about two more minutes to be sound asleep.

It just felt good to have this very sexy senior, cuddled up to me. Each time I'd look at her sleeping, peacefully, she seemed to have this very contented grin on her face.

Saturday morning, we were eating breakfast, after another great fucking, when Millie got a phone call, which she took in another room.

She must have been talking for twenty minutes, or so, when she came into the living room, where I was sitting.

I could tell something was bothering her, so I asked her what was up.

"Just family issues, Coop, nothing that I want to burden you with."

"What if I tell you it wouldn't be a burden?"

"Oh, shit, its just my oldest granddaughter who just doesn't get along with my daughter-in-law, her mother."

"And?"

"She wants to come and stay with me, and get some things straightened out with her life. It seems as if she just has never fit in with any group all through school. Plus, she's just survived a serious bout of cancer, on top of everything else."

"Is there anything I can do to help?"

Millie just shook her head, no.

"Just so you know, if you need anything, all you have to do us ask."

"Does that include another great weekend of fucking? Before you answer that, I'm going to tell you this might not ever happen, again."

"I know, and I'll always cherish these couple of days, with you."

As I got up to leave, Millie moved next to me and gave me a very soft kiss, and hug.

"I can't thank you enough for making this old broad feel young and alive, again."

All the way back to my place, I had this smirk on my face, wondering if this was all just a dream.

First thing Monday morning, I got a package on my desk, with no return address on it. I cautiously opened it, and found a very nice, framed, autographed, picture of my very favorite baseball player, Edgar Martinez, the greatest designated hitter of all time, from the Seattle Mariners.

I guess someone in my group, must have told her I was a huge fan.

For the next few weeks, I'd see Milie and her granddaughter in our office. Let me describe Joanna, her granddaughter. She was on the tall side, maybe 5'9" or a bit more, and was quite heavy, but I'd never guess her weight. I could tell she wore a wig, guessing she'd lost all her hair from her cancer treatments.

On the third trip into our offices, Millie finally brought her into my little cubicle.

"Joanna, I'd like you to meet Cooper Donaldson. Coop, Joanna Harris."

As I stood to greet her, I couldn't help but notice a sadness in her eyes. I had her sit down, and just as we sat, Millie excused herself, and left my area.

"Is my grandma forcing you to talk to me?"

"Nope, don't you consider the fact that I just might want to meet you?"

This brought a little smile to her cute face.

"Can I tell you a bit of my family history, Joanna? I never met my grandmother, since she died of ovarian cancer, when my dad was six years old. So, please count yourself lucky the treatment you've received has worked so well."

As we talked a little more, I did find out that she was turning twenty-one the following weekend.

Just then, Millie came back and told me I was invited to her house for this birthday bash.

Let me interject, here, that ever since our sex filled weekend, we'd done nothing more than a friendly hug, or two. She did, however, give my ass a squeeze or two during these hugs.

Was Millie trying to fix me up with Joanna? I'm not sure. I did know that I'd never shared that fact with anybody about my own grandma.

The following Sunday afternoon, I was back at the Harris estate, with a little surprise for Joanna.

As she came into the foyer to greet me, her eyes opened as wide as possible, when she saw that I had completely shaved my head.

"You big goof, did you do that to try and make me feel better?"

"Something like that, I guess."

I took hold of her shoulders, and gave her a very nice hug, holding her body as close to mine, as possible. I could feel her body shudder just a bit, when Millie came out and just stared at my very shiny head.

After meeting all four of her children, and three spouses, I was just starting to wonder where Joanna's mother was, when a lady came into the room, I hadn't met, yet.

"Cooper, this is my mother, Diane Harris. Mom, this is my friend, Cooper Donaldson."

After a semi cordial greeting, I could tell why they didn't get along. Where Joanna was very full figured, Diane was pencil thin. Almost to the point of looking anorexic.

Where Joanna wore an E cup bra, if not bigger, mom barely needed one.

All during this lovely party, nobody mentioned anything about my shaved head. Who knows, maybe they thought I kept it shaved all the time.

As we mingled, I was pleased that Joanna kept introducing me as her friend. After our fantastic lunch, and most of the guests had left, leaving just the family, I was bombarded with questions about my intentions with Joanna.

"To all of you, I hope you know that we've only known each other a few weeks, and we are just friends, for now."

"Cooper, this is just my family protecting me, and not trying to interfere."

As we sat, talking for a while, I realized she had her arm through mine, and I had to admit, liked it.

As I got up to leave, her father, Craig, came up to me and very nicely told me he had his eye on me, and for me to be on my best behavior. He said this with a grin. Her mother, on the other hand, just nodded my way, as I was leaving. What a bitch.