Roadblocs Pursuing the 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

In Pursuit of a Very Hot MILF

The Second Time is Twice as Nice

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Having spent an almost sleepless night in my cottage and backyard with a sexed up, sexually open minded and very fit Lorraine, I fell asleep on the plane before it took off and stayed that way almost the entire flight. A sleeping pill helped; I just hope I didn't snore or drool too much.

I woke up as we descended into Montreal and the flight attendant thanked me for being the easiest and most pleasant passenger on the plane.

I smiled and replied "I'm in Las Vegas and LA a lot so text me if you want to have a cup of coffee." I handed her my CYN Suits business card and said to her, "Look at the website for one you like and I'll measure you personally to make sure it's a good fit." She grinned and said she would.

When I cleared customs in Montreal I was surprised to see Catherine and her entire family waiting for me.

I kissed Catherine and gave hugs to the girls. Isabella kissed me on the mouth again and Tom pumped my hand like I was his best friend.

I had carried a bag with me so we got into the SUV quickly and headed to the hotel for dinner.

Catherine had arranged for us to have adjoining rooms. She put a shower cap on to keep her hair dry and as we showered together before dinner I gave her part one of my conversation with her ex. The good part. Not that there was a bad part.

She washed every inch of me, kissing me like she hadn't seen me in a month. Seeing Catherine naked and her washing my back and front caused a sleeping giant to emerge.

Although she didn't need it, I used the bar of soap as an excuse to get my hands all over Catherine.

She said "I like what I see" and after she dried me had me lay down on the bed where she gave me a quick blow job, swallowing my load as I erupted in her mouth.

"That should hold you until tonight" she mused as she licked at my balls.

Holding hands we met everyone on the rooftop restaurant. We were the last two to the table but that was fine.

My God Catherine was beautiful! I know I was only gone for two nights but it seemed like two years.

We had a nice dinner and everyone wanted to know what I did in Los Angeles. I filled them in on my clients and what was going in those companies. I left out my sexual escapades. I also did not share in front of the girls that I had met with their dad (Catherine's ex) or leased the house or bought the two view lots.

After dinner, Isabella took the girls to the hotel gift shop and Tom, Catherine and I had another glass of wine, finishing the second bottle and enjoying the view.

In front of her dad, and she had prepped me while I was in the shower, Catherine asked me about my assets. She had been asked a couple of questions by her dad when I was gone so she told me to be ready.

Catherine asked me, "Jack, can you please share with us what all you have and do, business wise?"

I replied: "Well, my house is paid off. Like most places in California it's over valued but for arguments sake it's worth a million. I bought a house nearby but in a different city about a month ago that's worth half a million. There's a mortgage on it of about $50,000 and I'll pay it off by the end of the year. Just before that I picked up a three bedroom town home about a mile from my house for $500,000. I owe $50,000 on it and I'll pay that off in three months. So, hard assets of $2 million or so."

I took a breath and continued.

"In addition to my mergers and acquisitions business I own a profitable dry cleaners with two locations. We have six employees working there. I'm a part owner in a specialty medical clinic that's profitable and throws off a lot of cash. Under 20 employees. I'm also a part owner in an after market automotive manufacturing business. We have 100 employees. I just launched an internet clothing company in Las Vegas. We're up to 12 employees. I'm looking at franchising a pool and spa cleaning business nationwide. The clothing company is a start up but is projected to break even starting next month. So, roughly, these businesses throw off, combined, over a hundred grand a month. Some months a lot more."

Catherine was looking at me with a dazed expression on her face. She had no idea about my finances. Tom had a sterner look on his face which I couldn't read.

I emptied my wine glass and continued.

"I've invested the life insurance settlements with a financial advisor who is growing it nicely. I haven't touched that money. I just got paid for the sale of that business that Gloria worked for. That was three million. I've invested some of that. I've been approached to invest in a new hotel in Las Vegas. I'd be a minority partner. It's been recommended to me to look into buying or starting a limo company. I just opened escrow on two view residential lots in a gated golf course development near where I live now. My plan was to lease a house there and build a custom home for us."

Catherine reached out and grabbed my hand and squeezed it.

"I also have five more businesses in the pipeline to sell in the next two to three years which will generate at least a couple of million, depending on the sales price. And, there will probably be more of those coming into my sales funnel."

This was what Catherine was teasing me about the night Gloria got sick and Cynthia got on the bus. She wanted to know how many harems I had. How many companies I had as clients. I told her but she had no idea about any of the other ladies in my life.

The waitress came by and Tom said to her "Another bottle please." We were drinking Silver Oak Cabernet. Napa. Most Excellent!

Catherine looked at me and I looked at her and we kissed, in front of her dad.

Tom cleared his throat and said to us, "Jack, you have a lot going on and if you'll pardon me, maybe you're a bit too spread out."

I laughed and replied, "Tom, I know I am but it's by design. When my wife passed I was so lost I didn't know what to do. I started drinking and questioning my faith, asking why God did this to me. I didn't sleep, couldn't eat and was going to hell in a hand basket. Then one morning I woke up and said I just have to go on. It was a little bit like that movie Cast Away with Tom Hanks. He reaches an understanding about what he has to do, twice in the movie. Since then, I've intentionally kept overly busy so I wouldn't dwell on losing my wife."

The waitress uncorked the bottle and brought us clean glasses. Tom left to visit the restroom.

Catherine kissed me and said "I told my mom you asked me to marry you but you'll need to ask my dad for permission. He's kind of old school that way."

I asked her "What did Isabella say to you when you told her?"

"Jack, she started crying. She said her prayers had been answered for me and her granddaughters. She is so excited. She loves you Jack, she knows you're a good man and will be a good provider. She also told me we would make beautiful babies together."

I kissed her and said to Catherine "It'll be fun making them won't it?"

She laughed and said "We can start warming up tonight."

Tom sat down and we resumed our talk.

I said to him, "Tom, I'm not going to ask you for Catherine's hand right now. Lets spend more time together and hopefully, we can get to know one another better. But I want you to think about something. How would you feel about spending nine months a year in LA, and returning to your lake home in the summer? I have a need for a CFO at that after auto market manufacturing plant I'm part owner of. I know you can do the job with your eyes closed. You and Isabella can live in my house. I've got a arrangement with a dealership and every year you and Isabel will be driving new cars and they cover all the gas, insurance and maintenance."

I looked at Catherine and said "You get a new car each year too sweetie. It will be waiting for you at your house when you get home."

Catherine clapped her hands and kissed me, laughing in celebration.

I continued, "Plus Tom, you'll get the opportunity to buy into this manufacturing company and be an owner with no money out of pocket. I want you to think about it. Whatever your last salary was we'll give you a twenty percent bump, plus full benefits for you and Isabel. Its a casual work environment so no need for suits or ties and there is a four day, ten hour work schedule so you will have a three day weekend every weekend.

Tom took a drink and said "Keep going."

I replied "I don't know what else you need other than to see the place so maybe you and Isabella can fly out to LA and check everything out sometime in the next couple of weeks. You know, when we finish our vacation here. And we can hit a couple of games at Dodgers Stadium if you like."

He laughed and said "Should I bring my clubs?"

I nodded as I drank some more wine.

"Yes, we can play at any number of courses."

Isabella and the girls walked up to us at that point, sharing all they learned on their walk through the hotel gift shop.

And they showed us what they bought.

Shopping is a gene found most often in the female of the species and they learn it early on. Marie and Natalie were well on their way to learning the craft of spending.

Isabella sat down and Catherine got up and took the girls to their room to get ready for bed after we said good night to them.

Isabella wanted another glass of wine.

Tom turned her and asked "How would you feel about living near our granddaughters nine months of the year?"

Isabella smiled and said "As in move to somewhere warm and sunny where we don't have to shovel snow and be indoors for months at a time? And we can stop freezing our asses off? How soon can we go?"

Tom laughed and said "We can fly out in a couple of weeks and check it out. How do you feel about me going back to work?"

Isabella looked at me and asked "Are you offering Tom a job?"

I nodded and drank some wine.

Isabella said "Thank you Jack, he's driving me to drink just sitting there in front of that damned Fox News channel all day long. He is always talking back to the television. He doesn't really understand that I don't care about that stuff anymore."

Tom laughed and said "Are you curious where we'll live?"

She shook her head. "I'll live in a tent. I'll be near Catherine and the girls that's all that matters to me."

I said, "You'll be living in my house and you'll like the neighborhood and the neighbors. It's got everything you need except for clothes and you can buy them when you get there."

"How far from Catherine's house?

I counted on my fingers and said "Two stop signs and two traffic lights so maybe five minutes."

"But" and I looked at Jack, "If we get married and move into the lease it will be two stop signs and three traffic lights so maybe ten minutes."

We talked about LA and all the places they could get to for three day weekend trips. Isabella couldn't wait to go. She already had the harsh Canadian winters in her rear view mirror.

Having put the girls to bed Catherine rejoined us and got another glass of wine.

"The girls wanted to know if I was going to marry you Jack" Catherine shared. "Their biggest concern is what they would call you."

Everyone looked at me and I said "Let me suggest that they call me D2, as in dad number 2." They all laughed.

We weren't feeling any pain when we left the restaurant and I have a sneaking suspicion that Tom got lucky that night.

For dessert I dined at the Y lying between Catherine's tanned toned thighs. Even though I had only been gone a couple of days I could see that her golden colored pubes had grown and as I teased her pussy, bringing her to the edge and then letting up until she was begging me to let her cum, I extracted from her that I would get to shave her completely in the next 24 hours. At that point she would have given up her ass just to cum but I didn't add that into the negotiations.

I brought Catherine to the brink and beyond as my tongue licked from her asshole to her clit while my hands tickled her tender inner thighs. I stuck my right finger into her molten hot cave and found the soft pad of her g spot while my tongue rode her clit. My left hand reached up and pulled on her ample right breast and found the tight tip, her large eraser size nipple.

She gushed for me for the first time, drenching my face and the sheet as she screamed in excitement, her left hand pulling on her left nipple. She literally shivered as she came down from her orgasm, getting into the fetal position with a pillow between her legs.

I moved up behind her and held her. Catherine started laughing her bedroom laugh, saying "Oh my God Jack, I came so hard it scared me. Do you see what you do to me? I'm going to have to start traveling with you. My body can't take you being away for even a night!"

She could feel my hard cock between her cheeks and in a couple of minutes she stretched a bit and lifted her right leg and said "Honey put that big beautiful cock in my pussy." She was sopping wet and her lower lips gripped me but I slid in all the way with a single push. It felt unbelievably good. So fucking good.

Catherine turned to her right and said "Let's practice making a baby sweetheart." And we did, I took her in six positions from the book finally dumping my load deep into her welcoming cunt after bringing Catherine to two more mind blowing orgasms.

We moved to the bed in her room to avoid the huge wet spot. I told her if her girls knocked on the door I'd go back to my bed.

Catherine and I fell asleep in each other's arms. She kissed me and said "Catherine Colton. Mrs. Catherine Colton. I could get used to that name. In a hurry. I love you Jack Colton."

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My body clock wakes me at 5:30am to work out and I did. Catherine was dead to the world. We didn't have anything scheduled so I left the room and found the gym.

I got my workout in and for the first time in almost 24 hours checked my phone for texts and emails.

There was an email from the attorney that had handled my civil case against the car dealer. The message was to call him after 6am LA time on Friday. He left his cell number.

At 7am I was sitting in the lobby restaurant at a table drinking coffee and reading the paper when Isabella walked up and sat down.

I wasn't expecting her but I welcomed her with a smile and a kiss. She kissed me on the mouth, it's just her way. The waitress poured her coffee and Isabella said "I knew I'd find you here. How was your workout?"

I replied "It's hard to get out of bed but I have to do it or I'll get lazy and then fat."

She smiled and said "We haven't spent anytime alone and I wanted to speak with you if that's okay with you."

I nodded and replied "Sure."

She smiled and said "Tom isn't in the best of health so if you have a job for him it can't be too stressful. And if he can work reduced hours that would be helpful. I won't have him dying at his desk."

I asked her how old Tom was and she said, "I went to work for him right out of high school. His first wife had passed and we hit it off and we got married when I was 22. We had Catherine when I was 23 and Tom was 35. So he's 65 now and I'm 53."

Isabella smiled at me and said "If I was single and just a few years younger I'd have you in my sights Jack."

My mind drifted back to Wednesday when I spent the night with Lorraine who was in her mid 40s. She was hot, tight, wet and oh so willing. A three hole lady.

I smiled at the memory of Lorraine taking my cock up her ass. I looked at Isabella and said "I can hire someone to be Tom's strong right hand at the manufacturing company so he doesn't have to be there all the time and you and I can plan out the calendar so that the two of you go out of town on the weekends to relax. Sometimes with us and sometimes with the girls. I also know a dynamic personal trainer he can work with everyday. I can have her work with you too if you want. If you like I can hire a personal chef to cook meals for you and Tom. And hire a housekeeper. Did I miss anything?"

"Just one thing Jack. The money. He stresses over money."

"What do you mean Isabella?"

She reached over and took my hand. "Jack, he's worried about not having enough money for me if something happens to him."

I nodded and said to Isabella, "I think I know how to address this. You worked in accounting right?"

She nodded.

"I'll put all my businesses under a holding company and I'll make you the treasurer. You'll handle the money and we'll put you on the payroll and we'll get life insurance on both you and Jack. Will $10,000 a month be enough for a salary for you?"

Isabella started to tear up which was not my intent.

"Isabella, don't cry. I just want you to be good with things. Okay?"

She nodded. And a weak smile emerged.

I took both of her hands. I said to her "Isabella, you need to listen to me. I'm going to put you in charge of the money but I'll be counter signing every payment made and every cent we spend."

I continued "But you need to know that what goes through the business is only between us. You can't share the information with anyone else. Not Tom. Not Catherine. No one. Understood?"

She nodded.

I said "Nothing is illegal but some of my business dealings are in the gray area. I don't want to have to explain it to anyone. I'm not avoiding taxes or hiding cash. But I am being very private about my dealings. I trust you to keep it all confidential. And tell no one."

She nodded again. Then she asked me if what I had in mind for her was full time and I said "No, probably three hours a day max. If you wanted to volunteer in the girls classrooms you'd have time to do that. And time to play tennis. Did Tom tell you about your car?"

She shook her head no.

I said to her "You get a new car every year. When you and Tom come out to LA you get to pick the one you want."

Isabella looked at me and said "You are an extraordinary man Jack. Now tell me about this clothing company you started in Las Vegas."

So I did and as I did, I understood where Catherine got that bemused look on her face when she was skeptical of what I was telling her.

When I finished Isabella said "I have a few questions Jack. First, did you get this idea to meet pretty girls?"

I replied "Initially I started it because I wanted to sell something globally online at a premium price that had sizzle. I was looking to make money when I was sleeping. People are living on their iPhones and I want to be part of that."

Isabella continued "And do you meet a lot of women with this bathing suit business? I would imagine you do if you're selling sizzle."

I said "I am constantly meeting attractive women who I think would look great in one of our creations. I met one on the plane yesterday."

I continued "I have a couple of suits in mind for you to try on."

Isabella smiled and said "Jack, I'm flattered but let's stay on the topic. You strike me as a very attractive man with considerable financial means who has no trouble meeting and let's call it dating women. Dating could be anything from having a harmless cup of coffee to a night in a hotel room filled with nothing but sex. You've been single for more than six months and you've been in a sexual candy store most of that time."