I Seduce a MILF at The Adult Pool

This is an adult sex story.

All the characters are of the age of consent or far over it!

Any children named or mentioned are not involved in anything sexual.

This is story number fifty five (55).

This is the story of how I spent my summer vacation in Las Vegas, Nevada, USA.

Enjoy and thanks for the views and votes.

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When you last saw me, I was sitting out by the adult pool of my hotel in Las Vegas, watching a very nice looking MILF by the name of Cheryl Mills from Denver, Colorado struggle with her too small, too tight of a bathing suit.

Not only did the suit not fit, it wasn't a good color for her.

Some women look good in black, some in red, some in white; some in stripes. (Some look better in no suit at all).

Cheryl had on a red suit but with her skin tone and brunette hair she needed to be in dark blue.

I didn't want to approach her directly, and scare her off, so I had one of the ladies from my new health club (Las Vegas Fitness Challenge) come out to the pool from the hotel and welcome her.

I handpicked Lourdes, a young Latina, because she was very nice, liked to meet people and was in no way threatening.

If you've read my stories, you will remember Lourdes. Originally from Mexico, she was one of my first CYNSUITS models, and I plucked her cherry (her virgin pussy) and her virgin ass one weekend earlier in the year, in the same hotel, once I was able to separate her from an overbearing, over protective chaperone. (The chaperone was a pretty nice piece of ass too).

That was all covered in my story That Was The Week That Was (story number fifteen (15)).

Lourdes was also something of a showcase, or testimonial, when it came to health, wellness and fitness and I had coached her to share the "before and after pictures" to all of our new Challenge guests to inspire them.

After greeting Cheryl, and spending a few minutes talking to her, Lourdes brought Cheryl over to my air conditioned cabana and in between doing some very pleasant tasks, the delightful Miss Mills essentially spent the afternoon and evening with me.

The guests all received a nice hotel room with pool view and early check in, late check out, free bathing suits, free custom gym wear and shoes, and a clothing allowance for dinners out and a few cultural excursions and tours, like visiting Liberace's museum.

I didn't set this thing up to find new women to have sex with. I was more interested in getting my hotel rooms filled.

But as it turns out, it was a great way to meet MILFs; I just had to be careful and not be greedy or stupid.

You know, chasing too much pussy in crowded airspace. Or in a crowded hotel.

I made a management decision to pick one woman each week to seduce. Hell, I mean to get naked with. To fuck.

With that in mind, I targeted Cheryl to be my bedmate and party girl while Lisa the UNLV professor was out of town visiting her parents.

You'll hear more about Lisa in a future story.

****

It didn't require much effort on my part to seduce Cheryl.

She was lonely, bored and like all women her age, horny. Add a few drinks, a hot day, out at the adult pool and you get spontaneous combustion.

The perfect combination, the best intersection, for me.

Yes, I know, you are thinking that this guy Jack Colton, well, all he has to do is look at a woman and she's wet between the legs, panting for his cock, bent over, thighs spread, ready to satisfy his every want, his every desire.

The truth is that I had to work to get laid just like every guy.

But unlike every guy, I had three things that were in my favor.

The first was the trappings of success, or put another way, I had money and resources.

The second was that I was always looking for new, fresh pussy to fuck.

(Most guys work long hard hours and don't have time to chase skirts. When they do get it, it is either on the road, away from home, or it's someone they work with. With me, it's almost my full time profession).

And third, I wasn't tied down to a wife. Yes, I had a wife but we were separated and when in Las Vegas, like I was, well, sport fucking was the game I played pretty much 24/7. And why not?

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Cheryl was divorced, no kids, but she was conservative, as most bankers are.

What was working in my favor was that she was in Las Vegas.

She knew what she was getting into when she made the reservation.

Cheryl wasn't topless out at the pool that first day but I will share with you that it was my unstated goal that all my Challenge participants graduate from the class by being topless at the pool.

This after a hard week of working out, weight lifting, seasoned with just a bit of booze to reduce the inhibitions and making lots of new female friends also topless made it easy for conservative types like Cheryl to brazenly parade around a pool with about three percent of their body covered.

We also sponsored and promoted the idea that these topless women (and we always got a group picture) would meet again at my hotel for an annual reunion and another expensive session at the Las Vegas Fitness Challenge.

I've explained before that I am seeking for divorced or widowed professional women to seduce.

They need to be educated, not interested in a boyfriend or marriage; score in the 6 or 7 or 8 range on the ten scale; be fun, in decent shape, articulate.

It helped my cause if they hadn't been laid in awhile but I usually only learned about that condition once I had their bra off.

If I got the bra off, I knew I was home free. Maybe not at that moment, but soon.

Oh, and one last thing.

I believe that my cock is standard size for a man of my stature; I'm just over six feet tall.

Many of the ladies were, so they said, astonished or amazed, at the size of my erection.

I did not want any of these women freaking out that I was "too big" and fortunately, none of them said that.

When women first see my dick, in an aroused state, many gasped, some smiled (meaning, "Thank you Lord"), a few nodded (as in, I could get into this) and the remainder just took it in as if to say "All in a day's work. But is this going to be fun or what?"

I know this sounds unbelievable, but they after that initial response, all of them licked their lips in anticipation of the meal they would soon enjoy because the women I date like to suck on a cock to see what they're getting into. Or what's going to go into them.

But all of them took on the opportunity to pleasurably partake, to enjoy, what I think all of them would admit was the biggest cock, if not one of the biggest cocks, they had ever seen.

****

It took me until the third "date" to bed Cheryl; to poke her.

I knew she wanted to do the dirty deed with me from the get go; when we first met out at the pool.

And when I did, when we did fuck that first time, and the other times, it was good, very good.

I made sure that she thought I was good and that she was fully, completely satisfied.

I used my fingers, my hands, my lips, mouth, tongue and cock.

It was a fun game, this game of seduction; sometimes frustrating but worth the effort and worth the wait.

****

Lourdes escorted Cheryl over to the cabana where I smiled, shook her hand and got a good look at her close up.

Cheryl stood just over 5'6" tall, with a slender shape that just made her boobs, not small to being with, stand out that much more.

My first thought was that she was cute, with freckles across her nose, and as I discretely noticed, across her ample chest.

Cheryl had a nice smile and liked to laugh and tell stories.

She was a brunette and well maintained. She took care of herself, mostly, but she had gained a few pounds, mostly in her ass and chest, just based on what I could see.

I'm not a fan of the Big Booty but this lady didn't have the Kardashian A$$.

I knew that just a few sessions in the gym plus not sitting in an office chair would slow down and maybe reverse the hated "Secretarial Spread" that office working women get in their forties.

Cheryl's larger body parts were struggling to get into a bathing suit from her past.

I didn't mind that her tits were coming out the tops and sides of her suit because I rather enjoy looking at half naked adult females.

I soon discovered that she was smart, articulate and seemed like a nice person to know, to have around and to be around.

I asked about her background and we quickly established that we knew some very professionals in common in the banking community and more specifically, in the Denver area. I encouraged her to reach out to them for a reference on me.

Cheryl was a bit embarrassed about her bathing suit being a bit tight, a bit small, and it looked uncomfortable, so I pulled out my iPad and reminded Cheryl that as part of her Las Vegas Challenge fee, she was entitled to up to five bathing suits from CYNSUITS. I explained that if she would pick the suits she wanted, Lourdes could measure her and that the suits would be delivered within the hour.

I had Lourdes go get a bathing robe, those soft white pool suitable garments that went to mid thigh so Cheryl would have something to wear while we enjoyed lunch together.

Agreeing with my plan, I stepped out of the cabana and closed the drape behind me, providing privacy for Cheryl to take off her suit and for Lourdes to measure her for new ones.

I knew that Lourdes was going to have her hands all over Cheryl. Discretely, at first, but later, brazenly.

Cheryl may have been a horny MILF but she had restraint, decorum.

At least while sober.

Lourdes, on the other hand, loved both men and women and when it came to sex, was open to anything.

Anything.

I knew what was happening inside the closed cabana. Lourdes was undressing Cheryl, and taking her sweet time doing it.

Lourdes liked to undress her female prospects by first putting their hair up, exposing as much skin as possible.

Then, after a short little massage of the neck, Lourdes would say something in Spanish tinged English "I must remove your top to massage your back" and presto, the target would be naked except for her bottoms.

Lourdes would ask the lady in question to put her hands up on her head, thereby lifting her breasts.

This would Lourdes the opportunity for a little side boob rubbing, before coming around the front of the target and checking out her headlights (by now on high beam), and then running her hands down the lady's sides, Lourdes would get down on her knees, her face crotch high, where she would proceed to peel the last bit of clothing off the target.

Lourdes always complimented the ladies on their legs, and when she did so, her hands were usually on their thighs, while she was sizing up their pussy.

All of this is quite innocent, yet very intimate.

Then, standing, Lourdes would proceed to measure the lady, taking her time, not being at all shy about where her hands were, and while not overtly teasing the lady, getting her aroused nevertheless with the constant movement of her tiny hands all over, all under the guise, I mean, assignment, of getting a good measurement for the complimentary swimsuits.

I listened for awhile and told myself that this was proceeding nicely, and then I ordered two bottles of expensive French champagne to help get this two person party started.

The great thing about bubbly is you drink it in these tiny flutes, and if you keep filling the flutes up, the lady in question has no idea how much she has consumed.

Lourdes discretely called over the measurements to the factory and followed that with an order on the iPad. We don't do anything without the proper paperwork!

The factory was a bit slow that day so each of Cheryl's suits were assigned to an experienced seamstress and they were completed in record time. I even showed the live cam as the suits were being measured and cut, and based on Cheryl's measurements, the finished suits, one at a time, were put on a mannequin for a quality check that Cheryl could see.

To get Miss Mills alone, I asked Lourdes to check on Cheryl's room and to make sure that her luggage was taken care of.

Cheryl and I had lunch out by the pool, under the shade and the misters, talking business and personal. The two bottles of bubbly went down fast and they didn't seem to dent her brain.

Two bottles down, I ordered a nice bottle of white wine. After first sipping, and then gulping the large first pour of Cakebread Cellars chardonnay, Cheryl started to loosen up.

When we first were together she would clench the top of her robe closed, but after about mid first glass she sort of let it open, allowing me a nice view of her freckled chest and the tops of her large breasts. She had a pair worth sneaking peeks at.

Cheryl also stopped holding the robe over her legs, allowing me to see most of her thighs but she kept her honey pot under wraps as every lady should.

She had a great pair of legs; those also came into my vision.

I couldn't help wondering what it would be like to be between those tanned thighs, licking and teasing her to orgasm after orgasm, prepping her for a bout with my very hard cock.

Given her bathing suit, I figured that she had a shaved or waxed pussy or something damn close to it.

I also wondered how tightly she would wrap those gorgeous gams around me as I pounded her steaming twat.

At one point my eyes must have glazed over thinking about fucking her when she caught me looking at her legs.

She just started swinging them, knowing full well I was entranced by their beauty.

When I came out of the horny fog I lifted my eyes to hers and she smiled, asking me with a light voice, "Like what you see?" to which I nodded and said "I sure do."

Now down a full bottle of champagne and one big pour of ice cold chardonnay, Cheryl was much, much friendlier to me. She knew I was looking at her; she knew I was interested, but wine or no wine, she couldn't actually throw herself at me. That would be what a wanton slut would do.

And Cheryl Mills was no slut. She was a good girl. But she wouldn't be for long.

I'd make her first solo trip to Las Vegas a memorable one.

For the first time in a long time, Cheryl knew someone found her sexually attractive.

So, we played the mutual attraction game.

It was only a matter of time before we would fuck. And we both knew it.

****

Post lunch, I complimented Cheryl on her selection of suits.

Lourdes hand delivered them to the cabana and without preamble, took her own top off to go topless for the rest of the afternoon.

Cheryl looked a bit surprised but Lourdes simply said "I like being topless."

Cheryl sifted through her five suits.

She had done a nice job picking her CYNSUITS, and they all looked like they would not only fit her, but that they would make her look good; very good in fact.

When she held up the bottoms all she saw was a tiny strip of cloth for her backside.

Cheryl said she thought she was getting suits with full coverage of her ass but the ones that got delivered only had a thong.

Cheryl protested that the new suits showed far too much of her to ever leave the cabana, but after the second large pour of Cakebread was finished she needed to pee.

I asked her if she wore thong underwear and she laughed and said "Yes. But not in public."

I responded with "Look around you. Women are half naked and no one cares and no one stares. You'll have more cloth on you than most of the women out here."

She looked at me trying to decide if I was lying or telling the truth.

Changing the subject because I was pushing her boundaries and I knew she really wanted to go out in public but was looking for me to give her permission, I teased Cheryl, saying that she couldn't wear her robe anymore.

"Make a choice" I directed.

Despite Cheryl's misgivings, but fueled by the champagne and fine white wine and the need to pee, Lourdes took Cheryl by the hand and they went the long way around the pool to the restrooms.

On their way out of the cabana I did a combination ass pat and rub on that MILF ass and Cheryl jumped in surprise and then laughing, wagged those nearly bare cheeks at me.

I liked spanking that ass. I liked watching that ass too. I was going to really like fucking it.

Two ladies holding hands is a turn on for guys, and for some ladies too.

It helped that Lourdes was topless; she had a great rack in a city of great racks.

I don't doubt for a minute that many people watching the parade assumed that the two of them were lovers.

Cheryl, being the older of the two, was the "man" of the relationship and Lourdes was the "woman."

That was my fantasy too, but I wasn't going to bet money on it, just let it happen, if it was too happen. Lourdes was always up for pleasing me, and if I asked her to take care of Cheryl, let me just say I'd like to be there, watching.

But only for a short while, because then I would want to participate.

I had a vision of Lourdes fucking Cheryl with a strap on, thereby expanding the banker's sexual library. Or having Cheryl use the strap on to pleasure little Lourdes.

This pair of hotties walked around holding hands, allowing everyone out at the pool that day to get a nice long look at Miss Cheryl Mills.

Not only did she turn heads, she received more than a few compliments from both men and women. The men wanted her number and the women wanted to know where she got her suit.

Talk about a transformation!

Lourdes also got looked at, but she was topless and well, plenty of the guys stopped to speak to Cheryl even though they were looking at Lourdes big firm bare tits.

****

I had Lourdes keep sun screen on Cheryl.

Lourdes got topless at my initial suggestion and stayed topless; not to show off or show up Cheryl but I wanted Cheryl to see how easy it was to be topless.

Once they got back from the restroom, Lourdes told Cheryl that she needed lotion on her.

Cheryl nodded and finished off another glass of cold white wine.

Sitting behind her, Lourdes undid the neck strap of Cheryl's suit and then undid the tie at mid-back.

Cheryl modestly held her top so that her breasts were covered.

Lathering her hands up with the sun block, Lourdes went to town, very liberally depositing the lotion on Cheryl's neck, shoulders, back and back of her arms.

Lourdes also did a short massage on Cheryl's neck which Cheryl seemed to enjoy.

I stood in the doorway of the cabana, taking this in.

Then Lourdes turned around and said "No peeking Mister Colton. I have to finish putting the cream on Miss Cheryl."

Lourdes had me stand in the doorway, blocking the view of the voyeurs.

I soon turned so that my back was to the opening so I could enjoy the show.

Then Lourdes had Cheryl move to sit facing away from the opening and Lourdes moved so that she was kneeling on the deck while Cheryl sat in front of her.

Lourdes got comfortable kneeling by pushing Cheryl's thighs apart.

Initially she did this starting at Cheryl's knees, but her hands moved up Cheryl's thighs until they reached the apex.

I knew exactly what Lourdes was doing; she wanted Cheryl's hips spread meanwhile her fingers were just outside of Cheryl's new bathing suit bottom. I am sure that some fingers did some gentle, unspoken teasing for a few short seconds to light Cheryl's fire.

Smiling, a confident and every helpful Lourdes gently removed Cheryl's top so that Cheryl was completely topless, but Cheryl was hunched over, covering her breasts with her arms and cascading hair.

Lourdes whispered "Please sit up straight Miss Cheryl so I can see you" and with that, Lourdes reached up with both hands and put her hands on Cheryl's shoulders and gently pushed Cheryl upright, so that Lourdes could see the beautiful large bare mounds and pink peaks.