I Rub an Asian MILF the Right Way

Late April

It had been a very busy first half of the month for me, not only with client work but getting going on two business opportunities, meeting and starting to date Lisa, mentoring Susan and keeping Monica going on her massage and sexual education.

Each Tuesday, Wednesday and Thursday morning my contest with Monica continued.

She tried to get me to cum quickly using only her mouth and I tried to stave off exploding down her willing throat.

I tried all the usual mind games but in the end she got better and better at giving head to me.

Having her watch the videos helped and I sensed she was winning most days but in the end I always won.

How can you not win when you come down the throat or into the mouth of a very hot babe who loves to suck and swallow?

I cannot begin to count the number of times she thanked me for all the sex I was giving her.

Monica felt respected, wanted, appreciated and sexy.

I paid her well so she would have financial security.

I had plans to include her in my two new business opportunities.

I had made a decision to hire a personal trainer for Monica, to get her into shape for a photo shoot I was thinking of doing in Las Vegas.

My plan was to make her the first model wearing our new swimsuit line and use her heritage to market the line in Mexico and other countries south of the border.

I had Monica go to the gym and work out with the trainer three days a week for 90 minutes, each Tuesday, Wednesday and Thursday morning after she took care of my sexual requirements, cleaned the kitchen and the bathrooms and did the laundry. She also had massage class in the afternoon.

The personal trainer was female and I had interviewed her in person to make sure it was a good fit.

I wanted someone who was friendly and would make it easy for Monica to work out and want to work out.

Her name was Julie and see seemed to be a nice and competent.

Like most personal trainers, she was sort of a gym rat but she had some meat on her bones.

I thought she might make a good swimsuit model but I didn't say anything.

I immediately noticed a drop in Monica's weight, saw some muscle tone in her arms, butt and legs and she had better posture.

When she was done working out she came back to the house and I often joined her in the outdoor shower.

Monica liked that I washed her hair and we sometimes made love on the lounge chairs under the covered patio.

Being naked outdoors and fucking was primal.

I found myself spurting more into her when we fucked outdoors.

Monica noticed I came more when she blew me outdoors, whether we were in the pool, the hot tub or on the lounge chairs.

My decision to invest in Monica was a good one for the bathing suit business and the pool cleaning business.

My contractor announced that my cottage was finished early and it was ready for me to move in.

I brought in the same interior designer my late wife had used for decorating our house and told her I wanted the cottage done. Her name was Kim.

Anyway, the third Tuesday of the month, after another glorious early morning blowjob from Monica, but after she left for the gym, I had Kim come over to show me her recommendations for decorating the interior of the cottage.

She was very attractive.

I had limited dealings with her in the past but I remembered how impressed I was at her beauty.

She was somewhat flirty with me, and she did a lot of touching of my arms and hands.

Maybe it was her way, or maybe she was interested. I couldn't tell for sure.

I enjoyed talking with her and her sense of humor and her laugh.

I didn't see a wedding ring. I thought I had noticed one when I met her previously.

I wrote her a check for her estimate and added $500.

I told her I wanted it all in and done by Friday at 5pm.

She could work around the clock if need be, the neighbors didn't care and neither did I.

If she could do that, I would have a bonus for her.

As soon as Kim left and Monica returned from the gym I gave Monica a thorough tongue lashing of her still sweaty pussy. I reminded her to close her eyes and imagine it was Susan's tongue bringing her pleasure.

I'd never seen Monica get so heated up so fast. She had a very vivid imagination because in no time she was holding my head with both hands begging me to let her cum. The river flowed and she groaned loudly as she climaxed. I was glad I had turned on the waterfall to mask the noise.

I turned her over and pounded her doggy style until I came into her hot wet snatch. It was a big load.

Monica asked what had gotten into me and then she smiled at me, knowing that Kim had gotten into my head -- I had been fucking Kim in my mind while tonguing and fucking Monica.

I had Monica clean me with her mouth; she knows how much I enjoy this so she took her sweet time, paying special attention to my balls and she rimmed me too.

Monica shampooed and conditioned my pubic hair and then trimmed it up nicely. She was a woman of many talents.

She finished the morning by giving me a second blowjob as I sat on the steps of the pool, imagining Kim's lips and tongue pleasuring me.

What would I do without her?

Kim did meet the Friday afternoon goal and when she came over to check on things, I gave her the bonus I had in mind, three days and two nights in Las Vegas, airfare for two, hotel and meals plus spending money.

I asked her to dinner that night and she accepted. We went on a date to the local Morton's and got drunk. Well, not exactly but we kissed a lot and it got hot and heavy. Fast. She didn't sleep with me but I knew I could get her there.

My wife had been a great customer of Kim and also referred a lot of business to her.

When my wife died, a chunk of Kim's business went away and I could tell, without asking, that she was hurting financially.

I wasn't sure if Kim had a boyfriend or what.

She was being coy about being with me but we did text and talk daily the next few days, just to say hi.

Kim seemed interested.

At our first date I did talk to her about going on retainer with me because I was looking at buying some houses and office buildings. I wasn't trying to bribe her. I recognized professional talent when I saw it.

Over the weekend I had a visitor; the story follows below, but let me finish on Kim first.

On Monday morning I mailed her a retainer check for $15,000 to cover the first month and a half.

I didn't tell her I was sending the check in advance.

Kim must have been out and got home later in the day.

Once she got her mail she texted me and said can I come over?

I said please do and she showed up about 20 minutes later, looking gorgeous as usual.

Summer blouse and shorts, great tanned legs and a beautiful smile.

Before I could close the door behind her she was kissing me and then she started to cry, she was so grateful for what I had done.

We ended up going to the local Mexican place for fajitas and margaritas and I brought her back to my place where we fooled around a bit before she left to go home.

I wanted to get her into the hot tub but I settled with getting her blouse and bra off, fondling, kissing and sucking on world class natural breasts (movie reference: Thank you for Smoking) with very sensitive nipples and playing with her pussy through her panties.

Kim was trying to be a good girl and holding off getting naked for some reason.

I knew it wouldn't take much to get into her panties. Just one more date and I would be in heaven.

So, Kim was a work in progress. Another iron in the fire. And causing a fire in my pants. I did my best to start a fire in her panties.

So what happened over the weekend between when Kim and I went to dinner on Friday night at Morton's and when I dropped that check in the mail on Monday morning? Plenty.

While I had originally thought I would have Monica, my maid, run various errands for me, I changed my mind once I really had time to think about things.

Don't get me wrong, I did use Monica for errands because my travel schedule required it. But I was strategic in my use of her.

If there was a good looking lady working at a place that I thought I had even a remote chance of having sex with, I decided that I would not send Monica there.

As an example, I live near eight Starbucks locations. Two have some very good looking women working in them.

So, if I sent Monica out for coffee, I'd direct her to any of the other six locations.

I didn't want anyone thinking that Monica and I were together.

My dry cleaners were on the no fly list.

I got to know the Japanese lady who owned the dry cleaners because I frequented her business.

Her dry cleaners were more expensive than the competition, and she did provide higher quality.

But more than that, the reason I kept going back was because she was very pretty, with a great figure and a nice smile.

She was a Very Fuckable Asian and I just knew it would be a nice ride if I ever got the opportunity.

Her eyes were bright and she was always reaching out, touching my hand or on the back so I knew there was something clicking between us.

Her name was Akiko.

Once a week or so I would drop off and pick up my suits, ties, pants and shirts.

I'd usually come in towards the end of her week, mid to late afternoon on Saturday.

If I missed a Saturday she would ask where I had been, and I always told her a business trip. This meant I had spent the weekend with Lisa.

For many months her husband was there too, he was a nice guy, very friendly and we'd talk a bit.

But I found out later she wasn't married.

She was divorced, no kids.

The guy I had been speaking to was her brother, and he moved back to be with their aging parents as he was the oldest son.

I found this out when I just came out and asked her why I didn't see her husband anymore.

Akiko burst out laughing and said it was her brother, that she used to be married by no more.

All this time we'd exchange pleasantries and have brief conversations, but I noticed she was now often alone in the store.

I knew she enjoyed my company because her face lit up when I came through the door.

My plan was to invest some time in seeing if I could get something going.

The memories in the house were painful.

This is why I was spending so many nights in hotel rooms.

My backyard cottage was just finished and I was planning to spend the night in my new bed.

As I was dropping off and picking up my dry cleaning and said to Akiko, you look tired.

She said she was, it had been a long week.

I asked her if her feet and back hurt and she looked up in surprise at me, how you knew.

I said you have a retail business, you are on your feet most of the time standing on concrete and you work long hours every day.

No wonder your back and legs hurt. And your neck and shoulders probably do too.

I think she was genuinely taken back that someone she hardly knew would be as insightful and considerate about her as a person.

I reached into my wallet, took out my credit card to pay her and after I paid the bill, handed her my masseuse business card.

When I gave her my card, I did it the Japanese way, with both hands offering it, head slightly bowed.

She said what is this, I thought you were a business man.

I replied that I was, but that I also gave massages and if she was interested I would give her one to help her back and feet if she wanted.

I did not expect her to say yes, I just wanted to plant the seed in her mind.

She thanked me and tucked the card into her purse.

I wished her a nice weekend and said goodbye.

To my surprise, I got a text from her about 30 minutes later, asking me if I could give her a massage later that afternoon after she closed the store.

I had a long week at work but the prospect of new pussy got me reinvigorated.

The kind of pussy I had been thinking about.

A chance to break in my brand new bed.

I replied in a few minutes saying yes, I was all set up at my home and could accommodate her anytime after 6pm.

We exchanged a few more text messages, with my address and all that, and I also told her she would benefit from being in the hot tub before the massage, so she needed to bring a bathing suit.

When I hit send I wasn't sure she would go through with it, but she replied back with a happy face.

Then I sent a message saying that I was going to order some food in for dinner and what did she like?

She replied with the name of her favorite restaurant in town (it was one of mine too) and she told me what she wanted.

My next text was beer or wine and I heard back Chardonnay.

Any label in particular?

La Crema.

I had some in my wine rack and I transferred four bottles to the fridge. And I loaded up on champagne too.

For insurance, I popped a 100mg Viagra.

Bob Dole, if this stuff worked for you, it will work for me and I'm a lot younger.

I knew enough about alcohol and Asian women to know they can't handle their liquor very well so I figured I really had a chance to poke her if she drank enough.

Akiko arrived just before 7pm, and she told me she had quickly gone home, changed into summer clothes and grabbed a swim suit.

After a tour of the house, which she said impressed her; we went to the backyard for an early dinner.

She asked if I was married and I told her I was a widower.

I wasn't looking for sympathy but I am sure I earned some from Akiko.

I had turned on the waterfall so the backyard was filled with the sound of flowing water, restful and soothing.

Not knowing what kind of music Akiko liked I put on some slower jazz and piped it into the yard, at a very low volume.

We ate on the patio in the shade, misters on to address the heat, making small talk and drinking our wine.

Akiko was very animated and excited, it was as if there was a very different person having dinner with me than the lady I knew from the dry cleaners. Her English was pretty good but there were a few words and phrases she got tongue tied on.

I tutored her over the language humps and she was often reaching out and touching my arm, a good sign.

We had a lot of eye contact and laughs. We were sitting perpendicular at a table overlooking the pool and waterfall and there was some innocent touching going on.

I kept the wine in an ice bucket with a white napkin covering the bottle.

I made sure her glass was never empty.

I never filled up her glass, I just kept it at about half full, and so she wouldn't realize how much she had consumed.

Being very polite and kind, I pumped her with questions about everything in her life, and she opened up like a floodgate.

At one point Akiko had tears in her eyes when she shared the details of her divorce.

Apparently she and her husband had opened up the dry cleaners together and her husband had been stealing from the business from the get go.

The missing money kept the two of them always struggling to make ends meet.

When her husband didn't show up at work one morning and neither did the cute 22 year old girl that worked for them, Akiko had to call her parents and brother for help getting through everything.

By now we had been outside for about 45 minutes enjoying dinner and wine so I got up and stood behind her and started in on her neck and shoulders.

After a few minutes of massaging her through her clothes, I suggested that we get into the hot tub and relax her back muscles.

As she grabbed the bag with her suit, I took her hand and we walked over to the cottage.

She didn't resist the hand holding.

As we entered, I pointed out the massage table in the sitting area, and then took her on a quick walk of the rest of the place; the bath and a half, small kitchen and the bedroom.

I said please freshen up and change into your suit and I will clean up the dinner and meet you in the hot tub.

Ten minutes later I was still in the kitchen putting things away when I saw her walk over to the hot tub.

She walked fairly steady for someone who had consumed almost 3/4 of a bottle of chilled white wine but I knew she was close to her danger zone.

I admit, she looked good in a swimsuit.

She had put her hair up and the color of the suit was a good match for her skin tone.

Her breasts were large, strapped in, flat stomach, with great legs and a nice ass.

For someone I estimated to be in her late 30s she looked fine.

The suit she had on was fairly conservative. Which is what I expected.

The sun was setting quickly behind the hills and I turned off the misters and turned on some of the lights in the backyard but kept the hot tub area dark.

I came out a few minutes later in my suit, carrying out a bottle of champagne and two flutes.

When I stepped into the water, Akiko said to me, you have a beautiful home and I thank you for inviting me here.

She was looking at my body when she said this, and smiled at me.

I'm not young anymore but I do keep in pretty good shape.

Normally I'm working out at 5:30 each morning for about 45 minutes.

I thanked her, popped the cork and handed her a flute of champagne and then toasted to removing her neck, shoulder and back pain.

She laughed and we drank, looking in each other's eyes.

I put our flutes up and asked her to turn around and sit in front of me.

With that she smiled and did what I asked.

I said you need to keep your chin above the water but keep your shoulders below so the water will relax your muscles.

I put my hands on her shoulders and started to massage them.

She said it hurts a bit but I know it will feel better soon.

I told her I needed to have her untie the strap around her neck and she reached up behind her and undid it.

Akiko pulled the loose straps to her front and she kept her hands holding up her top, covering her breasts.

For a few minutes I worked her neck and shoulders.

The combination of the wine, the warm water, the end of the workweek and my massage helped her to relax.

Akiko began leaning back into my hands, which was fine.

I then asked her to stand up so I could massage her back.

Standing behind her I asked her if I could unite the strap across the middle of her back.

She said sure, I undid the strap and she took her top off and put it on the ledge of the spa, so she now stood topless with her back to me.

Akiko put her hands on the side of the hot tub to brace herself, her ass sticking out a bit in my direction.

I was getting a semi but I knew if I snuggled up to her butt like I really wanted to I would be hard pretty quick.

She had a great ass.

So I kept a little distance between us.

I massaged her back by pushing on the muscles with both hands side by side trying to stretch them out and she groaned a lot.

She had me stop a couple of times to drink more champagne.

Akiko wasn't shy about drinking. My guess is she rarely let loose and when she did she felt safe doing so.

The alcohol may have also been her choice of liquid courage.

I was fine with that. Her courage allowed me to be bold.

Akiko stood up straight to drink but she never turned to face me.

What she didn't realize was that there was a reflection on the glass door of the house, so the entire time she was getting her back massaged I could see her tits.

They looked impressive, fairly firm and capped with large light brown areoles and prominent 1/2 inch eraser nipples.

I couldn't wait to get my hands and mouth on them.

When I had done as much as I could with her back I asked Akiko to sit across the tub from me and keep her feet underwater so I could massage her toes, soles and calves.

She looked over her shoulder and said okay, but you need to close your eyes, tell me when you are ready.