In Hot Pursuit of a Very Hot Milf

My stories are in chronological order. I encourage you to follow along and read these stories in this order as a prelude to this one:

I Hire Monica The Maid

Monica's First Day as My Maid

Monica the Maid's Three Hole Day

I Partner with Linda, A Salon Owner

I Massage Monica the Maid

Hot and Sexy Business Opportunities

I Become a Therapeutic Instructor

The Affair Continues in Las Vegas

I Rub an Asian MILF the Right Way

Going Where No Man Has Gone Before

Cumming Where No Man Has Cum Before

That Was The Weekend That Was

I'm Rewarded for a Job Well Done

Fun in Las Vegas with my MILFs

That Was The Week That Was

I Take My MILF Lisa to Mexico

I'm Ambushed by a Very Hot MILF

The CFO Gets Her Assets Worked Over

For background, let me share the main characters in my stories:

I became a widower unexpectedly in January. I was lonely and in pain; I made an offer my maid Monica could not refuse. She stayed on as my maid and became my part time sexual playmate. (I Hire Monica the Maid; Monica's First Day as My Maid; Monica the Maid's Three Hole Day, I Massage Monica the Maid).

Coming out of my funk, I decided to learn how to give massages and I met Susan, a bathing suit model, who was my massage instructor, and we became friends. Between Susan and Monica I came up with some new business ideas (Hot and Sexy Business Opportunities).

I met Lisa, a divorcee, who was a student of Susan's when I was a substitute instructor. We became lovers. (I Become a Therapeutic Instructor).

Lisa and I went to Las Vegas. (The Affair Continues in Las Vegas and That Was The Weekend That Was). I hired two ladies, Diana and Dana, to be with Lisa at the adult pool. Lisa arranged for my first threesome when we included her friend Michelle. (My Great Night in Vegas - not written as of this date).

After I met Lisa, and while I was casually dating her, I seduced Akiko, the lady who owned a local dry cleaners. I invited her over for a massage (I Rub an Asian MILF the Right Way). We traveled to Las Vegas (Going Where No Man Has Gone Before) where we met with Marie and Carmen.

The next day in Las Vegas (Cumming Where No Man Has Cum Before) I took Susan's virginity and enjoyed sex with Dana. On Sunday and Monday in Las Vegas (Fun in Las Vegas with My MILFs) I had sex with Dana and Sandy (a hotel food and beverage employee).

I enjoyed my second threesome in LA with Eva. She was a manager at one of my client companies. (I'm Rewarded for a Job Well Done).

Leading up to the photo shoot for CYN Suits, I spent a week between LA and Las Vegas (That Was The Week That Was).

After the photo shoot, I had a lucrative business deal close. I made a lot of money that day and a friend of my late wife re-entered my life (I'm Ambushed by a Very Hot MILF).

This story takes place after I met Catherine and also after I had sex with Cynthia (The CFO Gets Her Assets Worked Over").

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Catherine and her two daughters, Marie and Natalie, went off to Quebec on Sunday for a month long visit to her parents.

Early on Wednesday morning she texted me: when can you come and visit me here?

I texted her back: When do you want me to come?

She replied: I wish you had come with me and the girls on Sunday, I miss you terribly.

I answered: I'll fly in tomorrow and will send you flight details after I buy a ticket.

Catherine: How long can you stay?

I texted: I won't get a return ticket, we can play it by ear. I have some business stuff going on so I will have to shuttle back and forth starting sometime next week. But I only need to be in LA for a couple of days each trip.

I got a little red heart back in reply.

When I set my phone down, I looked around my empty house and said out loud, "Why should I stay here?"

There's nothing here for me. There's no one here for me.

Since I spent two nights with Catherine I had also slept with Cynthia, Dana and Julie.

Gloria I had to put on hold because Cynthia's virgin pussy was quite the attraction to my young middle aged cock.

But as I took inventory so to speak, Akiko was in Japan; Lisa was in the Midwest; Monica was in Mexico; the other ladies, Marie, Carmen and Sonia were in Las Vegas working.

I had just spent two nights and days being with Dana and one great night with Julie but I was alone now.

I wasn't interested in being alone.

I ended up quickly packing a bag and flying to New York on Wednesday leaving LA just after noon and spending the night in Manhattan.

I reached the conclusion (duh?) that I simply did not like to sleep alone.

It's a wonder my dick was still functional because as much as I loved my late wife we didn't have this amount of sex as far back as I can remember.

So I rested up on the plane. Six hours of smooth air and relaxation. I'm a little like George Clooney; if you didn't see the movie 'Up in the Air,' you should.

The airline I was flying didn't serve the champagne I liked so I settled for Bud Light. Two ice cold cans. And some baseball highlights on ESPN. Plus a stack of magazines that had piled up and a few issues of the WSJ.

Since I started my business, I've always flown first class. It's not that I am so big I won't fit in a coach seat. And I'm not a snob by any means. It's that the ride is smoother and the crew is friendly up front. Plus the passengers tend to have nicer manners. Not always but most of the time.

I also will only fly an airline when I get to choose the seat I am paying for.

I simply like being able to make my own decisions about where I sit.

Next to me on the flight was an attractive young lady that I thought would fit well into one of our suits so I invited her to check out our site and I gave her our pre opening price and a business card.

I walked around Times Square for a couple of hours that night and I hit the Museum of Natural History for an hour in the late morning before going to the airport.

Thursday at two I caught a flight to Quebec.

Two quick beers and we were descending.

Going through customs was a breeze, Canadians actually like people visiting their country. Especially Americans. I declared myself not to be a terrorist and they said welcome! Please spend money! Stay as long as you like!

Catherine was standing at the bottom of the escalator in baggage claim in a summer dress and sandals.

She looked Stunning. With a capital letter.

That megawatt smile was beaming at me and she was jumping with excitement when she saw me at the top of escalator.

Our hello kiss turned passionate which surprised me given her fairly public conservative nature. Her ample breasts crushed into my chest and she hugged me like she was never going to let me go.

As our lips parted, Catherine had tears in her eyes. Wiping her eyes she told me "You have no idea how much it means to me that you are here."

She kissed me again, deeply.

While we waited for my bag to show up she just held me tight, whispering to me, like lovers do, sharing what they'd been doing since they arrived, how everyone was looking forward to meeting me and how much she missed me.

With a gleam in her eye, and a smile on her lips, she told me, "You're still dripping out of me."

I kissed her back and said, "You bring out the very best in me and a lot of it. When can I have the pleasure of filling you up again?"

"Soon", she kissed me, "soon. But this time you sleep in the wet spot," laughing.

She snuggled up closer to me and said, "Not that you need them but those blue pills are a lot cheaper this side of the border."

I feigned surprise that I used Viagra, but followed up but "Tell me what it takes to get a prescription, just in case I am interested."

She said "We'll go to the doctor and then go to the drug store and get the pills. It's pretty simple. Like in America."

I said "Any doctor is going to take one look at you, then look at me and tell me that there must be something really very wrong if I need these pills."

She laughed and said, "We'll tell him they're just in case I'm horny and you're passed out drunk."

Catherine looked around to see if anyone was close enough to hear and then whispered "I can't remember how many times I came when we were together. I loved just being naked with you, just the two of us. Making love."

She kissed me, hard.

Then Catherine pulled me down so that her lips were right next to my ear and said "I've been masturbating each night thinking about when you ate me out."

She said "We fit together perfectly -- You are the perfect fit for my pussy. Which is why it feels so good when we make love."

Her eyes sparkling she asked me "Would you trim my pussy hair again?"

I replied, "I'll trim you anytime you like. Or, should I just shave you bare?"

She kissed me again and said "That might be fun, but you'll need to do it at least once a week."

Then laughing at me, she said "You'd be up for shaving me every day if I let you. Wouldn't you?"

I just licked my lips in reply and she kissed me deeply again.

She said "Tomorrow night I told my folks and the girls that we were going on a date so could we get a room for a few hours?"

I said sure, "We'd find a place. Did you have a preference?"

Catherine replied, "No, just a large swimming pool to exercise in and a big bed for us to be naked in for a few hours."

It was almost like we were in our own little world despite the fact that we were surrounded by hundreds of travelers.

When we got in the car we made out like teenagers. She pulled the car to a deserted corner of the parking garage. I'm sure we were on a security video but we didn't care. Things got so hot I had her dress down to her waist and her bra off so I could play with her fun bags. She came just from the kissing and nipple stimulation and I had the pleasure of taking her panties off to dry while we were driving.

She looked at the tent in my pants and said "You're going to have to take care of that yourself. We're going to be late to dinner if we don't leave right now."

Once we left the airport she told me "My folks live on a lake about an hour north of the city."

We went straight to a restaurant overlooking the same lake to meet the family for dinner.

Her folks, Tom and Isabella, were friendly and Catherine's daughters, Marie the oldest, and Natalie, the younger one, remembered me from my visits to their fourth grade classroom. They all told me that they were sorry to hear the news of the accident. I told them I appreciated their kindness.

Tom was a tall, barrel chested guy. He had a friendly way about him, a warm handshake and nice smile. You know that this is a stand up guy when you meet him. Tom had a great laugh and turned out to be a great story teller.

Isabella was a very pretty woman and I could see where Catherine got her looks and figure from. She was a hugger and kisser and she wasn't shy about wrapping herself around me. It was almost over the top until I realized it was her way, to be very physical.

Isabella greeted me with a kiss right on the mouth!

Catherine had briefed me about the sleeping arrangements on our drive. I had my own room at her folks house but she was planning on leaving the girls with her folks so we could have some alone time. And for the girls to have alone time fun with their grandparents.

We did do this, but not how she had originally thought it out.

She'd told her folks about me. They were cautious about a stranger dating their recently divorced daughter. This was my initial interview to get their first blessing, to persuade them I wasn't some flake. Or worse, like her ex.

Catherine didn't exactly say it that way to me, but that was the message I heard.

And, as for the girls, they were highly protective of their mom. They didn't want to see her get hurt again and they didn't want someone taking time and attention away from them.

We had fun at dinner, lots of stories and laughter.

Tom wanted to pick up the tab but I asked him if he would allow me to pay to thank him and his wife for their hospitality. He acquiesced, saying he'd get the next one.

When we got back to the house we spent the rest of the evening around their outdoor fire pit on the lake telling more stories and jokes. Catherine sat between her girls but we maintained strong eye contact.

The girls were impressed that I remembered what they studied in fourth grade and some of the activities they participated in. They were even more impressed when I knew some of their classmates, particularly the boys that had been behavior challenges for my wife.

My body was still on California time but when everyone else went to bed around 11, so did I.

Catherine came in to check on me and she kissed me goodnight, thanking me again for making the trip, promising me she'd make it worth my while.

Behind the closed bedroom door, I gave her two gifts.

The first was six Visa gift cards, each with $500 on them.

I also gave her an AMX gift card worth $3000.

I told Catherine "Use them for whatever the girls or your parents need when you're here. Groceries, dining out, movie tickets, clothes, gas, whatever. I don't want anyone not to go do something or not get something because they didn't have the money."

I didn't know her parents financial situation and I didn't want my visit to be a burden on them. Tom and Isabella might have been millionaires for all I knew but I wanted to pick up "our" share.

Catherine started crying and I just held her until she stopped.

I said, "Let's make this the happiest summer we've ever had, okay?"

Wiping away her tears, she smiled and said "Okay I'm all for that."

I said, "No tears on this gift."

It was an American Express Platinum card with her name on it.

I said, "This is for you. Maybe if I am very lucky someday the last name on it will change, but I don't ever want you to worry about not having money or not being able to buy something you or the girls need."

She held that card like it was a gold bar, beaming at me through the tears.

She looked at me with a sly grin and said, "Can I buy more little silk black panties that I won't wear?"

I just laughed, we kissed for a long time and she looked up at me and said, "I wonder how a new last name will look on this card. Catherine Colton. Mrs. Catherine Colton. I think it would be very, very nice."

I turned her around, patted her on the ass and said, "That is the question for the summer, isn't it? I'm ready for bed, let me go to sleep."

Catherine whispered "Good night dear."

My first morning in Canada Tom was up early and so was I. We sat outside on the wooden deck overlooking the lake, drinking coffee. I learned that he was born in Canada. His parents got out of France just before the German army took over the country in 1940. His parents were buried in Quebec.

He was retired, sort of a forced thing, he wasn't happy about not being needed or productive and I could only imagine what kinds of discussions he and his wife had cooped up in the house through 8 months of winter each year.

My impression was that he was bored out of his mind and needed to get back to work. But I kept my mouth shut.

Tom asked me about my business, and I told him the truth, I was a hard working, educated man and, fortunately I didn't have to work another day in my life. Except for the fact that I loved what I did and was in the process of diversifying my business interests and my real estate holdings.

I told him I wasn't bragging but he asked a direct question and I answered it in the same spirit it was asked.

He nodded and got direct with me about my intentions with his daughter. His only daughter. His only child. I was expecting his question and gave him another straight answer.

Catherine and I were getting to know one another and we were falling for each other but we were moving cautiously because we both felt that the girls needed time to get comfortable with the possibility of their mother having a boyfriend and even getting married. And, the girls needed time to get to know me. I needed to get to know everyone in the family.

I also told him my wife had passed not many months before and I was still grieving. I shared that it was hard coming home to an empty house and that I'd gotten used to spending nights in hotels.

I simply asked him to judge me on my words and deeds while I was here and maybe we could talk more about this before the vacation was over. I also told him I might need to fly back and forth to Los Angeles for business.

Tom said that was fair and added he had never seen his daughter so happy and he thought the girls were warming up to me too.

Catherine came out soon after with Isabella, and they had had laid out a long road trip with activities for the next three weeks.

I had told Catherine on the ride from the airport that I wanted to make this a summer holiday that her entire family would always remember.

That I needed to keep busy and traveling around Canada with her and her family would be a good way to help me with my wife's passing.

While I didn't know Tom and Isabella's financial situation, I had the means to cover the costs for our traveling expenses, hotels, rental cars, meals and all that.

I made it clear I had to work while I was there, but it wouldn't interfere with the fun. And if I had to leave for California for a few days I'd return to whatever city they were in.

As they outlined the calendar, Isabella could see how happy Catherine had become since we connected.

Tom and Isabella took the girls shopping for the trip.

Catherine and I headed out on our date. We checked into a Marriott on the other side of the lake. With my elite level status they upgraded us to a suite. We had a view of the lake.

We checked into the room and she undressed in front of me.

One look at her and I was on the rise.

Then she undressed me, kissing me and all over my body as my clothes ended up in the closet.

Catherine and I got into bed and did some serious kissing and fondling then she kissed my hard cock and gave me a nice blowjob. I moved my body around and pulled her on top of me so we could 69. I licked her to a nice orgasm, and she came quickly. I came just after, she swallowing my heavy load.

We snuggled for a bit and then we got dressed in workout clothes.

She went swimming and I worked out, then we took a nice long bath together.

Out of the bath, Catherine and I stayed nude, and we cuddled on the sofa, just enjoying being with each other. Lots of kissing, fondling, rubbing and spooning.

I liked the way she looked, felt and smelled.

Looking out over the lake, enjoying the early evening shadows grow.

I spent a lot of time gently rubbing her pussy, teasing her, getting her close, then backing off, ramping her up again and then cooling her down. All the while whispering to her dirty things that I knew would get her hot.

I entered her partially from behind as we lay there spooning, teasing her, not humping, just letting my cock soak in her juices, all the while teasing her nipples and her clit.

Finally I let her cum humping my fingers and you could have heard her scream down the hall.

She just shuddered over and over.

We ordered in a light dinner and champagne and Catherine stayed in the bedroom nude while room service delivered our meal.

She sat on my lap feeding me. In no time flat she got me hard and the spent the next 30 minutes moving around, rubbing up against me, changing her position.

Catherine straddled me, rubbing her golden pussy hair up and down on my erection. Then she turned around and rubbed her crack up and down my cock.

She dripped some salad dressing on my cock. She stood up, put her hands on her hips, looked down and said, "I better clean that up."