I take My MILF Lisa to Mexico

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

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

I became a widower unexpectedly in January. I was very lonely and 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).

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). I hired two ladies, Diana and Dana, to keep Lisa company 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).

This story takes place in June, after I had the first photo shoot for the new swimsuit line (CYN Suits).

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In the middle of June

My world was changing very rapidly.

It was just over six months since I buried my wife.

I'd started a number of relationships with women since then.

Some were ending and some transforming and some were being put on hold.

New ones were being made.

All were good for me coming out of the untimely death of my wife.

Akiko, my Japanese MILF, the lady who owned the dry cleaners, had returned to Japan for who knows how long. Maybe forever. Please read my stories about her: "I Rub an Asian MILF The Right Way" and "Going Where No Man Has Gone Before" for background. Before she left she sold me her dry cleaners and her town home.

It was not an easy parting. She had been by my side for just a couple of months and the one thing I knew was that she would not only take care of me, she looked out for me. Maybe it was because we were both business owners or maybe it was because we had lost someone close to us and understood the pain of loss.

I don't know why specifically we connected on so many levels but I respected her family's wishes that she return home and I helped her make the transition as easy as possible.

I did hire Akiko to develop business in Japan and the Far East for CYN Suits. We were already starting to get hits on the website from Japan and we changed the website so you could read it in over 120 languages; you just clicked on the flag of your country to see it in your language. We obviously avoided adding the countries where this kind of clothing was not welcomed (Iran, North Korea, Saudi Arabia and so forth).

I thought about meeting her in Hawaii because many Japanese travel there on vacation; literally by the planeload. Rather than sell our suits retail, on the beach, I knew there had to be a better way and I left that to Akiko to figure it out.

Monica, my maid, was in Mexico and couldn't return to the US for legal immigration reasons. Following the photo shoot in Las Vegas she had gone to the courthouse in her town for something trivial in her past and was arrested and quickly deported. I took care of the legal stuff including hiring an immigration attorney. That failed, so I bought her house to avoid her losing her equity in foreclosure.

For the time being I had Monica's two daughters living in Akiko's town house. To earn their keep, Monica's daughters were running the dry cleaning business and helping me out there. I knew I could trust them to do a good job with the customers and the cash.

I was still dating Lisa on a regular basis. I met Lisa in "I Become a Therapeutic Instructor" and "Our Affair Continues in Las Vegas." She was also instrumental in getting me into a threesome ("My Great Night in Vegas").

(I still need to write about the CYN Suits photo shoot and my first threesome in Las Vegas. Just bear with me, writing a decent recap is time consuming).

In June after getting the photo shoot behind me for CYN Suits, Lisa and I made a quick weekend visit to Puerto Vallarta where Monica was living. I wasn't worried about Monica but she had gone from her home to the courthouse to jail and back to Mexico in a blink of an eye, never to return to America again.

So, I was making the trip for personal and business reasons.

I had arranged for a videographer and a photographer to take shots and tape of Monica on the beach and around the hotel pool in various suits for the website. Lisa and I had not talked too much about the purpose of the trip. Lisa trusted me and let me pick the places we traveled too on the weekends when her husband had visitation with their children.

I talked to Lisa on the plane about being in the shoot. Lisa was excited to become a model. Like most women, she didn't think she was pretty enough, didn't have the right figure and all that. But she trusted me and I said she would be great, she said okay.

Once she agreed to be a model, I told Lisa I would pay her a nice royalty on every suit with her name on it that was sold, around the world, for a full year.

I had her look at the suit on the plane.

Lisa could not believe how tiny it was. I assured her it covered the essentials, barely.

The female flight attendant saw Lisa holding up the suit and proceeded to ask where she could buy one!

So, once we got to our destination I expanded the scope of the shooting to include Lisa.

As you recall, CYN Suits named each creation after a female. Our first suit was The Michelle. I had also created The Lisa, a suit I designed with my main squeeze specifically in mind. I spent a lot of time with different types of cloth draped on her body.

Lisa didn't know what I was doing because I didn't tell her -- I wanted it to be a surprise. She got tired of being my live mannequin so I rewarded her with massages and several severe tongue lashings of her beautiful pussy which I continued to shave using the bristle brush on her pussy every time we were together.

Lisa not only loved getting shaved she realized that because she was bare she was horny all the time. This forced her to sneak away and come to my house to get her itch scratched. I did it many different ways, all which left her purring and wanting more.

Or, I had her rub one out and asked her to video it and send it to me. If she didn't do this once a day I would text her and tell her I was waiting to see her with her fingers on her clit and pulling on her nipples. Or, I wanted to see her sliding a dildo in and out of her steaming cunt.

I'm not saying Lisa was like Pavlov's dog but she was always moist when I undressed her. I could smell her aroma as I peeled her tiny thong panties off. Her anticipation was high and I never disappointed her.

Lisa loved it when I ate her out. She craved it, my tongue and fingers and lips on her most intimate parts. She was far from silent when my tongue touched her pussy. I had her pulling on her nipples, but I would release her hands and she would grab my head and hold me to her crotch, she would hump my face and a couple of times she flooded the bed, creating a gigantic wet spot.

The first time she flooded she was embarrassed but I wasn't. It was just a barometer of how worked up I was getting her. One time she started crying she was so overcome with emotion. I held her until she was laughing and smiling again.

She thought when I first rimmed her it was very naughty but in no time she started to love the feeling of my tongue on her asshole. Her resistance melted away for good once I pierced her virgin hole in Las Vegas four times in two days. After coming in her ass, she started to crave anal sex almost as much as she liked oral sex. Crave might be too strong of a word but she enjoyed it, that's for sure.

I sometimes had Lisa close her eyes and had her pretend I was her friend Michelle licking her as she had done in Las Vegas during our threesome. She went nuts over that visual combined with my hard tongue placed firmly on her clit and one of my fingers fucking her fantastic ass.

My oral pleasures gave me a lot of credit with Lisa and she allowed me free reign with her holes. We tried new positions, new places to have sex and she made sure I came in at least one hole and often all three holes when I was with her, time permitting.

Lisa also liked it when I came on her. Like on her face, between her tits and on her back. I preferred to come inside her, but I didn't mind coming on her either. She rubbed my man juice on her body; she liked my scent. I think it was primal, her way of feeling she belonged to me.

Not near her home, but when we were gone for the weekend, away, I had Lisa dress with less, meaning; I wanted to show her off. And she loved it. No panties, under bust corset, thigh highs and sometimes braless. We had an ongoing contest to find the tiniest thong for Lisa to wear.

Back to the bathing suits. I created The Lisa with my young hot MILF lover in mind. My thinking was that the Lisa's of the world would only wear their tops temporarily out by the pool, lake and beach so the bottoms were more critical. I designed the bottom based on the various types of pussies I had enjoyed.

Female pussies do not look the same on the exterior although they all function the same. If you don't believe me, go look at an old Playboy magazine. The issues after the girls started trimming and shaving.

Design creativity was our competitive advantage at CYN Suits. We design your suit based on your pussy type and your nipple and breast size.

Before we left for Mexico I had planned both photos and videos in the suite, on the balcony, at the pool, in the hot tub, on the beach, in the surf and at the outdoor shower.

I had in mind Lisa and Monica together and separately, with their suits on, topless and nude.

I was going to be careful with the pictures so Lisa's face wasn't shown. I knew the suit would rapidly become a best seller once we posted the pictures and a video. Especially of the two ladies playing in the surf!

Monica texted me that she hadn't had a man since being deported. My prick was willing to fill the void.

It isn't a super long flight from LAX but when we arrived at the hotel Monica had arranged to give us a massage in our suite.

Monica met us at the door of our suite in a white robe. When the door closed she dropped the robe.

Her fantastic body had stayed the same but her bush had grown back.

Monica greeted us with kisses and hugs saying "Hello Mr. Jack and Miss Lisa. This weekend I am your servant."

She apologized for her hairy bush and asked me to please shave it before the photo shoot. This broke the ice and Lisa laughed and said "Monica he will shave you first then me." Then she said "Maybe I could help Jack out on that" smiling at Monica.

Monica smiled and said "I'd like that Miss Lisa."

Lisa and Monica hit it off immediately and Monica wasn't shy about suggesting without saying so about wanting to eat Lisa's shaved pussy. Monica couldn't take her eyes off Lisa. Or her hands as it would turn out. Or her lips, tongue, mouth or teeth.

Lisa loved the attention of another female and the touching.

Monica wasn't aggressive but was able to persuade Lisa to allow join her in the shower to prep for the massage.

They spent some time in there and I heard some giggles.

Monica took charge and got a clean, dry, and ready to be massaged Lisa on the massage table, face down, nude.

With the lights and music low, Monica gently rubbed Lisa to sleep.

I noticed this trend with Lisa; either on the way to or soon after we arrived at a destination she would fall asleep. I wanted to think that she was so relaxed with me that she fell asleep because she was comfortable doing so. Turns out having two little kids wears a mother out and so she crashed because she could. We were never in a hurry once we got to our destination and sometimes we never left the hotel.

Covering Lisa with a light blanket, Monica quietly undressed me and took me into the shower.

I don't mind saying that I had really missed Monica. It wasn't the daily blowjob and swallow, or putting a load into her very welcoming pussy, or even pushing my hard dry cock into her tight dry rosebud to maximize my pleasure at the expense of her pain. It was that Monica cared for me. And I cared for her.

She washed me quickly not wanting to do anything behind Lisa's back.

Monica took me out to the living room, my erection bobbing in front of me.

She sat me on a towel on the sofa and knelt on the floor between my knees.

Monica whispered to me, trying not to wake Lisa, "Mr. Jack, I've missed you."

And then the tears started. Our reunion was emotional for Monica. She didn't understand being deported and she hated being away from her kids. She had to leave a great life in America and now she was living in a place she had left behind 20 years before.

I consoled her as best I could. Her head was on my leg and I ran my fingers through her hair as she cried. My cock shrank as the tears, literally silent sobbing, continued.

It was all pent up emotion laid bare. Her life had changed and not in a good way.

When the tears ended I had her join me on the sofa and I just held her. I rubbed her back. Ran my fingers through her hair. Stroked the side of her face.

She looked to me and we kissed like long lost lovers. My cock grew rapidly as her beautiful and ample breasts rubbed my chest.

Monica pulled my mouth to hers with her hands as our tongues got reacquainted after a forced separation.

She just wanted to be held. Monica was lonely. She needed companionship. She was a stranger in a strange land. She didn't say that but I knew it.

In a few minutes she moved over, straddling me. Monica smiled at me. She knew she was about to be fucked for the first time in a long time. She was ready, very wet and hot and my erection slowly filled her as she slid me into her very hairy and very tight pussy.

She shuddered and climaxed as I entered her and she moaned lowly as waves of pleasure rippled through her.

She held on to me tightly until her orgasm finished, trying not to groan too loudly which I know she wanted to.

Monica whispered in my ear, trying not to wake Lisa "I needed that badly Mr. Jack. So badly. Thank you."

She kissed me and with me still very hard and inside of her, Monica started moving up and down on my cock to repeat her pleasurable experience.

She mouthed "I love your BIG COCK."

We kissed deeply and in less than a minute she came again silently but powerfully, like an aftershock of a big earthquake, only this time she collapsed into me. She was very wet and when she came, her moisture ran down my thighs.

Monica and I kissed for a long time and she leaned back and put her hands on my knees so I could suckle her large breasts. I licked at her nipples and sucked, careful not to bruise or nip before the photo shoot.

She knew I liked doing that and it kept me incredibly hard.

Monica lifted off my knees and whispered to me "You fill me up real good Mr. Jack. You always filled me up so good." She shivered -- a good vibration.

That got her hot and wet again (actually she was in heat and never cooled off) and she started riding me again, kissing me and rubbing her clit against me.

Monica came for a third time, this was a lower intensity orgasm. She smiled, kissing me and thanking me. She liked being naked with me, close to me, her bare breasts rubbing my chest, my lips on her lips, our tongues playing with one another. My hands on her body, her hands in my hair, holding my head to kiss her.

She whispered to me "Now it is your turn Mr. Jack" and legs shaking, she dismounted and knelt down on her knees between my legs and looking up at me, proceeded to suck me to a quick ejaculation, focused on the sensitive head and not deep throating me because she did not want my loud groans to wake Lisa.

I had been on the verge of coming since I slid into her. Her pussy was tighter than I remembered and the bush was a new erotic feeling. A different feeling.

But her mouth, tongue, lips and throat were created to provide maximum pleasure for me.

Her head moved rapidly and her tongue did wonders despite her juices on my penis. Her lips and mouth went to work focused on bringing me exquisite satisfaction and Monica out did herself.

As the ultimate moment arrived, I held her head down as I came into her throat for the first time in weeks.

I stifled my groan so as not to wake Lisa.

God how I missed that morning blow job and swallow!

Monica swallowed many times, my tip in her throating. The sensation was incredible.

When she pulled off of me, she ran her tongue around her teeth and showed me that she had swallowed my load.

She bent her head and licked at my balls, then, she started licking me until I was clean.

But her fingers continued to play with my balls - it was clear she wanted another load.

Her licking felt so good I remained hard, pretty much ready to go again.

Leaving my cock bobbing, Monica found another blanket and joined me on the sofa and we spooned.

I had both hands on her breasts and my cock fit nicely in her crack.

As I laid there I realized I had missed our daily sex sessions.

Her orbs felt so good in my hands and her crack was the perfect place for my erection.

In another life, in another place, we might have been a couple, with her kids, a house, a dog.

But my mind wandered back to where I was; in a hotel room with a willing naked woman.

My cock was solidly in her crack.

It didn't stay there long as Monica moved around a bit and reached beneath her to put me inside of her still dripping wet pussy.

Monica basically did all the moving and while I kissed her neck and ran my tongue around her ear, I also played with her nipples, while her right hand found her clit.

I came silently and she quietly shuddered as she came again.

I want to make it clear we weren't hiding anything from Lisa. We were simply trying to be quiet so as not to wake her.