I take My MILF Lisa to Mexico

If we had wanted to hide what we were doing we could have gone into the bedroom, or stayed in the shower.

Monica and I spooned on the sofa under the blanket and I moved my right to her sopping hairy pussy.

I rubbed her; pussy playing with it and her clit surfaced after a time and I rubbed her to yet another orgasm.

By now I was hard again and I first kissed and then whispered into her right ear "suck" and she got off the sofa and stuck her head under the blanket as she kneeled on the carpet.

Monica had learned to lick our juices off of my cock. It was something I enjoyed and sometimes I know she didn't like the taste but she never complained. She might slow down and take smaller licks but she always finished the job to clean me or to make me big.

As she took me deep into her oral cavity her left hand began to tease my tired balls. I spread my legs to give her better access and her right hand rubbed my belly. Her long hair teased my bare belly and thighs and she started to hum, enhancing my pleasure.

We had this contest, this battle, many mornings and I wasn't interested in fighting the inevitable as I finished in her mouth for the second time that evening.

Monica swallowed it all and proceeded to clean me again. Her tongue was tired but I encouraged her by putting my hand on her head to keep her on task. She knew how much I treasured her oral skills and she did not want to disappoint me.

She got back up off her knees to snuggle with me again. My hands went back to her orbs and I fell asleep with my cock between her cheeks. I was clean but dripping a bit. Monica didn't mind, she loved being next to me under the blanket.

At some point I felt Monica get up.

I kept my eyes closed and heard her kiss Lisa and say "Ms. Lisa, should I continue your massage?"

I heard Lisa's blanket being removed and then I must have drifted back to sleep but I woke up as Monica was climbing up on the massage table between Lisa's thighs, head down and ready to eat the young blonde MILF's shaved pussy.

There is nothing more erotic than two women making love to each other.

Its every man's fantasy to see this happen and I was blessed to be part of this on many occasions. Life isn't fair and I had more than my fair share of these delightful opportunities. To watch and to play.

Sometimes when the women got into it I felt like a bystander but in this case I was the facilitator and also a willing participant.

I came many times that weekend but I made sure the two ladies came more than I did.

That's how you build loving relationships: give more and take less.

I got up off the sofa and stood behind Lisa's head, my hands pulling on her ample breasts telling her to keep her eyes closed and enjoy the pleasure on a female tongue on her pussy. Lisa came twice in quick succession before gently pushing Monica's aggressive tongue away from her sensitive clit and slit, now very wet saying "No more, no more."

Monica kept her head between Lisa's open thighs, kissing and licking all around Lisa's sensitive pussy but avoiding direct contact.

My hands, meanwhile, massaged Lisa's head and face and then neck, calming her down, allowing her to relax from her orgasm.

I asked Lisa to keep her eyes closed and just enjoy the time of two people pleasuring her. Loving her.

Monica kept at her licks and kisses and in no time at all, my hands returned to rubbing Lisa's ample chest but I deliberately avoided her nipples.

I used some light oil with the goal of re-heating her love engine.

Monica kept her head down and her mouth, tongue and lips out, and her focus was on the soft inside of Lisa's thighs, avoiding her sensitive button.

As Lisa spread her thighs to ease Monica's access, Monica targeted Lisa's lower lips, still wet with dew.

Using only her tongue, Monica licked Lisa's pussy like she was eating oysters on the half shell.

My hands returned to Lisa's large and taut nipples as the love thermometer started to heat up.

As I looked down at Lisa she was under assault by Monica's tongue and my fingers and hands on her breasts.

It didn't take long for Lisa's clit to rise and when that happened, Monica penetrated Lisa's lower lips in search of her g spot with a finger and Monica lifted her head just slightly to allow her tongue to participate in the fun of licking Lisa's clit.

Between the probing finger inside of her tight pussy, and Monica's wonderfully hard female tongue on her clit, with my hands on her tits, Lisa started to buck for another orgasm.

Oh my God she came. She humped Monica's face, her hands reached out to hold Monica's head to her groin as she groaned and then flooded Monica's mouth.

Lisa shuddered and shuddered and cried out "Jack hold me!"

I climbed up on the table and just held her as she shook and shed tears crying at her very intense orgasm.

Monica, of course, lifted her head and got off the table, coming to stand beside me as I held Lisa on the table.

As I held Lisa, Monica rubbed my head and neck.

"Is she okay Mr. Jack?" asked Monica, very concerned.

"Give her a couple of minutes, Monica, she'll be fine" I replied.

With my right hand I reached back and Monica grabbed my hand and she pulled it to her crotch; it was sopping.

When Lisa got up her legs were shaking and she needed Monica's help into the bathroom.

While we waited Monica had me back on the sofa and she started licking my cock again, more to keep busy than anything else.

I had my hands on her head, encouraging Monica on.

Emerging from the bathroom Lisa sought out Monica and the two nude ladies hugged one another until Lisa pulled back and sought out Monica's mouth for a kiss.

And they kissed, and I can tell you it was fucking hot to watch.

It didn't take much effort on my part to convince Lisa to return the oral favor to taste Monica. But first I shaved Monica's forest off.

I dragged it out, actually putting shaving cream on her with the brush three times, under the guise that her hair was thick and required more use of the razor. The truth was I removed the blade the last two times because Lisa had her hands all over Monica and they kissed like lost lovers and Monica was moving around and I did not want to nick her.

Post shave, Lisa got between Monica's thighs to pleasure my Mexican MILF and I took Lisa from behind. I hadn't fucked my blonde MILF in more than ten days and sliding into her was so incredibly good I almost came instantly. Thank God I had been blown by Monica twice otherwise I would not have lasted long at all.

The rest of the weekend was a blur. I got into the action too, blasting into warm, wet, willing shaved pussies and tight, pulsating assholes that night. Monica blew me in front of Lisa and Lisa learned a few things about pleasing me orally. I loved it when both of them went to town on my cock. Two tongues are truly better than one.

The photo shoots turned out far better than I had hoped.

The affection they had for one another, or maybe it was lust, was visible.

It wasn't a Sports Illustrated fake smiles shoot but real laughter and feelings. The smiles were genuine.

The sexual tension was always high between these two. I was a tool that weekend as these two ladies devoured one another.

Our last night there, Monica pulled out a strap on and asked Lisa to please use it on her. Hey, when in Rome, right? I think Monica preferred a dick but trying a plastic one was worth a shot.

Lisa was tanned, exhausted and dripping from two holes and fell asleep on the plane ride back to LA. Before she fell asleep she told me that using that strap on was hard work and she appreciated all of my pumping!

Monica was satisfied beyond belief. She was crying when we left but she was secure, financially and otherwise and I sent her kids to see her the day I got back.

Not much more than a week later I sent Susan down to get CYN Suits Mexico up and running and Susan decided to stay there for awhile. It seems that my goal of seeing if Monica and Susan had made a love connection worked. Monica turned out to be quite the carpet cleaner according to Susan. And Monica told me that she made Susan lick her to an orgasm, sometimes two, before she would return the oral favor. Tit for tat; no, twat for twat. Lick for Lick.

I wonder how often they used the strap on?

You can enjoy my stories about Monica: "I Hire Monica the Maid," "Monica's First Day as My Maid," Monica the Maid's Three Hole Day," "I Massage Monica the Maid," and "Hot and Sexy Business Opportunities" so you can see what an important part of my life she was after my wife passed away.

Susan's stories are "Monica's First as My Maid," "Sexy and Hot Business Opportunities" and "Going Where No Man Has Gone Before" and "Cumming Where No Man Has Cum Before."

Lisa, my recently divorced MILF girlfriend, told me a few days after we got back from Mexico that she was spending the summer with her children at her parents house in the Midwest. Here are my stories about Lisa: "I Become a Therapeutic Instructor," "The Affair Continues in Las Vegas", "That Was The Weekend That Was." As I look back I am sure I read the signs correctly: that she was done with LA and would be moving back home in time for the kids to be enrolled in school.

Kathy, the salon owner, reconciled with her husband. As you will learn when I post the story about the photo shoot, Kathy got sick in Las Vegas and stayed sick for a few days before we could get her home.

Kathy and I had spent one night together, you can read about that in "That Was The Week That Was" but I never slept with her again. In Las Vegas she was ill and then when she returned home she reconciled with her husband. Which was good, I hate to see marriages that could be saved fall apart.

Sonia became my new part time maid because Kathy didn't want Sonia around her house when she wasn't there. She simply couldn't trust her husband not to fuck Sonia. I was introduced to Sonia in the story "That Was The Week That Was." More about her in a few lines.

Diana and I spoke after the model shoot and she said she had fallen for my web guy in San Diego so she continued to work on the CYN Suits website but was out of my personal life. It had been a very fun ride. She was just a beautiful lady ands my clients loved her. On a personal note, I was able to introduce her to anal sex which she enjoyed the more she participated - the more times we did it. She moved to San Diego and I was happy for her.

Marie was in Las Vegas working more than full time on CYN Suits. I needed to find someone to run the business. Carmen the stylist was around Las Vegas too but other than a dinner and a one-time sleepover I hadn't seen her.

The swimsuit business had taken off far beyond my expectations. Because of Diana's web marketing expertise (please read my story "The Affair Continues in Las Vegas") and Susan's much improved selling ability (see my story on "Hot and Sexy Business Opportunities") we were able to set up kiosks at all the adult pools (and at the other pools as well, selling tamer / lamer / more conservative suits).

I avoided having retail shops in the hotels. The hotels wanted me so sign leases, hire people, bring in inventory and all that but I stuck to my guns. I didn't want the overhead. The kiosk business poolside was seasonal and it worked for us.

Out at the pool, we actually fit clients and sold our bathing suits within two hours of purchase. A client would come into the kiosk, go behind the drapes, get measured, the team would send the information to our nearby factory and the suit delivered by courier within two hours but often in about an hour. Handmade. We allowed our clients to change into there new suit in our kiosk (or Cabana).

This ramped up the interest in our suits and we often had to have our prospects take numbers because there was a wait.

If a guest arrived at their hotel after the pool closed, we could send out the fitting team (two ladies for safety reasons) to their room and have the suit available the next morning (we had a graveyard shift cutting and sewing at the factory). We even took measurements via FaceTime and were able to FedEx the suits to clients around the world.

Sometimes clients wanted a tour of the factory but we were hesitant to show off our version of the secret sauce. I was paranoid about the Chinese stealing our designs and had a constant stream of paperwork flowing out to competitors and would be competitors. I didn't hesitate to send out a young gun attorney to visit someone to show we meant business. We'd file lawsuits quickly and aggressively. Sometimes my attorney worked a deal and we bought out the competition, which was essentially designs and customer lists.

The pool cleaning business was going slower but we had bought some routes in Las Vegas and had a couple of contracts at smaller hotels in the area. I had planned on Monica working in that business but she couldn't come back. I needed a plan B. Or maybe not. Maybe this was a business not worth building.

My clients in LA were fine. I was spending less time in Las Vegas than during the startup phase of CYN Suits but I was up there every week for at least one night, and sometimes more. I never slept alone. I didn't always have sex but I always had someone sharing my bed.

Lisa's friend Michelle was interested in me once Lisa left for the summer. We fucked a few times. I took her to a couple of some nice hotels along the coast in Santa Barbara and Palos Verdes but we both knew it was just for the sex and a good time. Don't get me wrong, it was very, very good sex but there was no magic in our relationship beyond the bedroom. We connected when naked but otherwise not. She turned a lot of heads and was good eye candy on my arm. She had an incredible body. I never said anything to Lisa about Michelle and I don't think Michelle did either.

I found work for Kim, the interior designer, in Las Vegas, working with smaller hotels and condos. I set her up in an office at the factory under her own company name and she designed our poolside kiosks, co-branding with the hotels.

I won't go into details but I did end up having sex with Kim a number of times in Las Vegas. The sex was great but as you recall, there was some reluctance on her part when I was trying to bed her. She was thinking she liked girls after her husband left her and so when she met me she was in no man's land. But I convinced her that getting dicked by me was a lot better than what her ex provided and she became a semi-regular of mine when I was in Nevada.

Kim also designed some special tee shirts that helped us to promote the business.

The first was a crop top, sleeveless, cut just below the breasts, to go with any of our bottoms. We called it Skin. We made it available in several colors, the biggest sellers were light colors which made the shirt transparent when wet. You'd be surprised how many ladies had no issue wearing tiny, wet and provocative tee shirts at the pool. Those tee shirts went very well with whatever bottoms they chose to wear. Or no bottom at all.

The second one (we called it Window) was a play on our diamond shaped tag sewed into all of our suits. The same crop top tee shirt had a diamond shape cut out revealing, depending on the breast size of the wearer, a significant portion of their breasts. Combined with water, this was about as revealing as a woman could be without actually being topless. At the request of one rather large breasted woman we sewed cups into this shirt for support. We made it optional and many women opted for the support feature.

The third one (we called it Strips) was one I designed specifically for the "nude" part of the day at the adult pools. I had Sonia in mind when I designed it. I assumed she was bottomless, and the top was a soft color (light green in her case) of strips from her neck to just below her breasts. Each strip was about one inch wide, with a one inch gap between, allowing plenty of "peek a boo" space for prying, hungry eyes. The back was open with only the bottom of the shirt across her bare back, sort of like a thin bra strap.

On the Sundays when I was in Las Vegas and the pools went nude optional at 3pm, I had all the ladies wear this revealing blouse (they got to choose the color they wanted) as they went bottomless.

Now here is the thing. The girls that wore Strips with hair on their pussy out sold the ones that were shaved. I don't know why. I just took advantage of it.

Sales skyrocketed at the kiosks those late Sunday afternoons. I had to bring in extra help to handle the volume.

As I discovered with my massages of females, the exposed part of the body feels more exposed when another part of the body is covered.

Kim's success at branding got me thinking about the potential of the business beyond Las Vegas to Cancun, Europe, the South Pacific.

Since that weekend preceding the photo shoot, I had made Dana my main squeeze. I had Dana with me most of the time. She wasn't living with me but we had a steady thing going.

I still had sex with other women, but I regularly fucked Dana in all three holes.

My older ladies (Akiko, Lisa Monica, Diana) had moved on but there were still plenty of playmates for me to chase after and I did.

But I had been burning the candle at both ends and after thinking about things I decided that sleeping regularly with a firm bodied young beautiful lady with a gorgeous face, large breasts and a near virgin pussy was not a bad thing, at least in the short term.

So, we somewhat cohabited the cottage in my backyard and various hotel rooms in Las Vegas.

Dana was very nice, she was hot and she loved to have sex. Yes, of course, she was on birth control.

I let her drive the car I had arranged to let Lisa use. Lisa gave it back to me when she when home for the summer.

I sent her to driving school so she would be better prepared to drive in LA traffic.

She did the grocery shopping and some errands around town and I had Sonia do the cleaning and cooking when we were there.

I also had Kathy do Dana's hair, changing the color from dirty blonde to brunette. Same with her eyebrows.

I wanted Dana to have a more serious look when selling. I didn't want her to get tagged with being a "dumb blonde." She was getting her degree and I wanted her to be taken as a professional. Being beautiful helped.

Looking the part was key so I invested in her clothing, spending money at Neiman Marcus on whatever I thought she needed.

I arranged for Dana to get a manicure and pedicure at Kathy's place regularly.

I also sent her to what used to be called a finishing school. Not that she lacked polish, but I wanted her to be up to speed on etiquette for business meetings, meals and all kinds of social situations.

They don't teach anyone these things in college.

My goal was a polished Dana who could and would be comfortable in every situation she would find herself in, business wise.

As far as Dana's bush was concerned, I allowed the dark blonde hair around her pussy to grow out and shaved the rest. It started to itch a lot and I'll get to how we addressed that in a second.

I wasn't sure exactly what the process was for dying the dark blonde pussy hair to brunette but Kathy taught Sonia how to do it and I supervised the process; both the trimming and the coloring.

Dana was responsible for keeping Sonia's pussy hair trimmed.

Trimming twats was a regular occurrence by my pool.

These two turned each other on when they did this task. I always scheduled it for first thing in the morning. It was something they looked forward to.

I wasn't shy about telling Dana why my plan was; I wanted her to wake me up each morning with a nice back massage in bed before I worked out. When Susan did that for me in Las Vegas it set the gold standard for how to be awakened.