More Trouble in Paradise

Trouble In Paradise

DAVE

I had to adjust my sunglasses which had started a slide down my nose in the hot tropical sun. Grabbing the sunblock from the table next to my chaise, I was extra careful not to knock over the just delivered frosty Corona beer. Applying the lotion liberally, I took care to take extra special care of my exposed dick and balls. Can't be too careful when it comes to the tools of the trade. In fact, Little Dave was starting to puff up a little because my favorite topless and close to bottomless waitress, Maria, had just brought the beer and had blushed when I flirted with her. She and her delightful titties were tempting but off limits since she was married to my friend Philip who also happened to be the 6'8" poolside bartender on the other side of the pool deck.

I could just have moved out of the sun to be under one of the poolside umbrellas or cabanas but the scenery was just too good this afternoon on the pool deck. I am after all a dirty old man of the first water. The entire pool deck was now crawling with topless and a fair number of bottomless ladies. It was unusual for so many unescorted women to be at the pool but Phillip had told me that there was some sort of Real Estate Brokers Seminar being held at the hotel and the girls were attendees. Actually I thought, "girls" was being generous. Most were, shall we say, mature and quite frankly were on the slightly droopy side but then naked is naked and I never get tired of looking at bare tits. I surmised that the group nudity had to be part of a dare or team building exercise. It was still fun however to observe the many varied breast and nipple types. Better yet there were several ladies who were definitely MILFs. More in the mid 30 to mid 40 range, athletic builds with nicely proportioned bodies. Anyone of them would be acceptable in my mind. Having parted company yesterday with a cute red haired divorcee from Omaha, it was time to select my next project.

I am in my mid forties but some folks have told me that could pass for ten years less. Over the last four years I have been on a strict regimen of diet, sex, exercise, sex, sun and yes sex. I am back down to my college weight of 180 and with my swimmer's 6'1" frame I knew I looked good. I have also been blessed with what could be called a pretty cock. It is just 7 1/2" long but it is smoothly unblemished and hangs full and relaxed from my shaved package.

After I finished my beer I got up, stretched and walked casually around the deck trolling for interested ladies. I then dove into the pool and proceeded to do a series of laps using both crawl and backstroke. By the time I climbed out of the pool and walked back to my chaise, two of the more attractive MILFs had moved over to the recliners adjacent to mine. As I dried off, I stood facing the ladies and opened a dialogue as they openly admired my shiny wet cock dripping just feet from their chaises.

"Hello ladies. My name is Dave and I've been told that you folks are real estate sales wizards and you've come to this clothing optional paradise in the pursuit of fun in the sun and of course to learn all kinds of new real estate tricks."

The woman closest to me held out her hand to shake and introduced herself as MaryBeth from Cleveland and her companion as Betty from Akron. She then went on to indicate that they were interested in studying more than just real estate but also the mating habits of the local male species and could I recommend a guide. As she spoke she idly scratched her right nipple calling attention to her very nice and perky 34 B's.

I held her hand a little longer than necessary and gave it a squeeze as I checked out the rest of her trim body. Unfortunately her puss was covered by a bikini bottom but other than that, I liked what I saw. I then turned to Betty and gave her the same once over. She was slightly more full bodied than her companion, probably a firm C cup but really an all around nice package wearing a thong bottom.

"Could I interest you ladies in a margarita or one of their fruit punches? Phillip does make excellent concoctions. Another thing you might be interested in might be the swim up bar. You get to cool off from this intense sun, get a little tipsy and check out the local talent."

The women gave each other a quick glance and both nodded with a subtle grin and stood to take my outstretched hands. With an arm around each pliant waist we moved together to the edge of the pool. My cock proceeded us into the water with a nice half hard display. Kicking off flip flops we entered the water via the steps and waded to the bar at the 3'6" depth.

At the bar I was in my element and by the third fu fu drink in a coconut, the girls were feeling no pain. Both of them wore wedding rings and from their conversation, their roving hands checking out my cock and the lack of objection when I fondled their nipples, I was not surprised when after 45 minutes we were headed to my private cabana adjacent to the pool area. Within minutes I was up to my balls fucking Betty from behind as she ate MaryBeth. Having lots of endurance because this was my second fuck of the day, I plowed Betty to several loud orgasms before I tapped her on the shoulder and told her to switch with her friend. After making sure that MaryBeth was satisfied in a similar fashion I asked her where she would like my load and she panted out "My pussy please." And so I gave her three more thrusts and let my load fly into her clutching womb.

Relaxing between the two women in the afterglow of sex, I toyed idly with their nipples and studied their bodies.

"I do have to say ladies that both of you really do take care of yourselves. Your figures are trim and firm and either you are blessed with fantastic genes or you work out a lot. I do have to ask through, both of you are obviously married and judging from the size of your diamonds, you married well. Do your hubbies know about your extra curricular activities?

Betty and MaryBeth raised up a bit and looked each other in the eye before Betty answered.

"The answer is most probably yes. A month ago we caught the two of them on a so called "fishing trip" to our family cabin with a couple of young ladies. The four of them were swimming without suits, only two beds had been used in the cabin and from the used condoms on the floor, nothing good had been happening. The boys were informed that the penalty for their cheating would be our trip here to study the mating habits of clothing optional resort patrons. You are our first case study and I must say the experience has been most positive and we are looking forward to even more data collection."

The girls and I partied together for the next two days before I introduced them to Harold and Perry, two black entertainers who were reputed to be the proud owners of 10+ inch cocks. The days with the girls had been fun but it was getting a little tedious knowing that all of the various sex acts we performed were mostly to charge up their memory banks to get revenge on their husbands. I knew that the black cock experience would really get them going and I was right. Running into the boys a week or so after the girls left, they thanked me for the hot hook up and complimented me on being able to keep up with them for as long as I had. Apparently by the time they poured them onto their flight home they not only exhausted Harold and Perry but the rest of their band as well.

Another reason for passing the ladies on was because I needed to recharge my batteries and rehydrate before Gail McFergeson arrived. I had met Gail for the first time years before in a strictly business capacity. She was a first rate bank representative and also it turned out a terrific little sex machine. She was now four years into getting revenge on her cheating spouse. I was happy to entertain her and to help her regain her sense of sexiness and self worth. She was a real tiger in bed and was charming, witty and intelligent too boot. I had once been the marrying type and Gail would have certainly have been right up my alley. However, that had been burned out of my system by my first wife and the best I could offer Gail was my friendship, banking business and whichever side of the bed she wanted. As I thought about Gail and marriage my mind had traveled back 25 or so years to my college days and the first love of my life Celia Packard.

I was 19, had just finished my sophomore year the the University of Pennsylvania and was relaxing in the sun as I surveyed the tanned bodies surrounding my life guard station at the Ocean City beach. It was a windy day, the the surf was high and there were few swimmers in the water. It was however a prime day for the girls to work on their tans in the smallest bikinis or thongs that their mothers would allow. In fact, even a few of the moms or MILFS had cut back on the size of their suits to take advantage of the June sun.

That was also the day I rescued a seven year old boy who had ventured out too far and had gotten sucked in by the undertow. When I carried him out all it took was a couple of chest pumps and the kid was puking up the inhaled water and tearfully crying for his sister who came running up crying hysterically. Despite the seriousness of the scenario at hand I was smitten by the girl. She was about 5'4", maybe 110 and with the most beautiful tanned figure imaginable. As she sobbed, her cute little B's almost popped out of her top and I had to fight to stop a growing hard on.

In short order, the head lifeguard took over. He praised me, checked over the kid for problems and finding none, praised me again, told the sister she was lucky that good old David was on duty and returned to his station to write up the incident. Celia was the sisters name and she hugged me so hard and long that I almost came in my trunks. She just couldn't let either her brother or me go and kept asking me what I wanted for a reward. I told her that the hug was reward enough but that her name and phone number would be nice.

When I called her that night her mother answered the phone and cried and kept thanking me over and over. Eventually she yielded the phone to her daughter and I told her to please cool it with the extravagant compliments because I was just doing my job.

"No way. You are the hero of this family and we don't give a shit if you are embarrassed. Now are you going to get your ass over here so I can kiss you again or not?"

Of course I went over that night. I was living for the summer with seven other guys in an old house that was close to but not on the beach. My swim team had a deal to provide 8 Red Cross certified lifeguards for the town's Parks Department. The job paid just enough to make it worthwhile but the bonus was free housing and 20 bucks a day for food. Since I was on scholarship and needed the extra cash for walk around money, who could resist? The obvious added benefit was exposure to lots and lots of ladies. The downside was we slept barracks style on a large porch so if you connected with a honey you had to improvise privacy in a car or sand dune.

Anyway, back to the story. After Celia's relatives got over the emotional stuff it turned out that they were really nice people and as a bonus they had a smoking hot 19 year old daughter. Celia and her brother were spending the summer at her Grandparents beach house. The Parents worked in the City and only came out on the weekends. It just so happened that the parents, grandparents and a bunch of other relatives were all there for the weekend and so I got deluged with a whole lot of unwanted attention for my five minutes of doing my summer job really well. Of course I did the "aw shucks" clean cut college boy routine and they all sucked it up.

After a nice cook out dinner and a lot of polite conversation, Celia and I managed to sneak away and walked down the beach. She very naturally took my hand and later was quite receptive to my arm around her waist and then a pause in the walk to collect that kiss. A simple kiss soon grew into "THE BEST KISS EVER." It went on and on and quite naturally I got a hard on to rival all hard ons and she rubbed right up against it. Eventually we broke for air and all I could say was "Wow." and then "I'm sorry."

"For what"

I pressed my hard on against her a little more firmly and she just purred and murmured "you never have to apologize for something as natural and impressive as what I'm feeling right now."

With that we kissed again and I grabbed her tight little butt cheeks with two hands and we rubbed together until she cried out as she came.

"Fuck, now I have to have you in me and fast."

It was dark but the beach still had strollers so we headed into the dunes and found a quiet little sheltered spot and there, 12 short hours after meeting her, Celia and I fucked for the first time. She was not a virgin, nor was I. Luckily I had two condoms in my wallet and I could have used a third. We were so hot for each other it was just unbelievable. From that night on you would have had to use a crowbar to keep us apart.

Once we started dating, I dumped whatever had been going on in my private life and concentrated solely on Celia. I had had several friends with benefits that had been local hook ups. I politely told each of them that I was going to be exclusive with another girl and I assumed that Celia did the same. We never talked about our past sexual histories but I think it was obvious to both of us that the other had not just read a really good sex manual.

Celia and her friends or she and her brother became a fixture at the foot of my guard tower the rest of the summer. Celia in my backseat every night also became a fixture and by the end of the summer three jumbo packs of condoms were history. She was addicted to my cock and I to her tight little pussy.

Our only problem on the horizon was what was going to happen in the Fall. I go to school in Philly and she was up in Princeton a good hour away. The distance would be a good test of our relationship. The only saving grace was that there was good one hour bus service between the two cities and so we would be able to get together on weekends by alternating who took the bus. There were of course exceptions especially when I had swimming meets but we did manage enough meetings to keep the horns filed down. I also found that it was a lot more enjoyable and fun to spend weekends making leisurely love in a real bed as opposed to furtive fucks in the back seat of my car or in the dunes. During the week we communicated through texts and email and I think we found out a whole lot more about each other with this written contact than we did in a whole summer at the beach.

By Christmas break we had discovered quite a bit about each other, most importantly that we really liked one another. Besides being highly sexed, we were both very good students and focused on our goals. Celia was on the Deans List at Princeton and was excelling in the Chemistry Department. No slouch myself, I was in the Honors program at Wharton and expected no difficulties in getting into the Investment Banking business.

The next four years flew by. There was lots of hard work and even a lot more passionate love making. By the time we walked across our respective graduation stages to get our Masters, Celia in Organic Chemistry and me with my Wharton MBA, we were more than ready not only to get to work but to get married. We took care of the later in June and after a two week honeymoon of sun and sex in Cancun, we settled into a NY loft and started work. I went to work for Chase in the Investment Banking Dept. and Celia joined the Chemistry faculty at Columbia as a lecturer. Our sex life at this point was the typical newlywed pattern of a quickie in the morning shower and monkey fucking at night. Our days were a different story. We worked at the opposite ends of Manhattan and we developed friends and acquaintances each in our own area. Therefore, something as simple as stopping off after work for a drink together was out of the question but all in all we were happy, in love and the sex was great as always. The only contact we had with each others colleagues was Christmas parties and the occasional dinner at an associates house. Inadvertently the pattern that was established in the early part of our careers would cause a problem later in life. We both came home tired from our work. We would give the cliff notes version of what happened that day but I know that I didn't really pay close attention to her struggles with the hierarchy at Columbia and I know she didn't really follow what I was up too. I think that both of us tuned the others business out except when it came to food or especially sex.

One of the keys to doing well in my industry has always been to develop a good contact network. The starting point was the Wharton connection. Probably 30% of the staffers in my Department had come from there and frankly we were sort of a closed group. Unofficially we had mentors and mine was Joseph Preston III. He was Joe to his friends and Three Sticks to his enemies. I had worked closely with him on a couple of projects and we clicked. We had compatible interests, senses of humor, intelligence and interest in women. After 18 months or so he officially took me under his wing as Assistant To the VP of Major Account Development. Joe's primary job was to convince wealthy major financial players to use Chase's services and to help them with their investment decisions. This wasn't really just being a financial advisor, it was more how to move various assets or currencies from A to B to C etc in the way most conductive to keeping the lowest profile regarding taxes and government observation. A crass individual might call this money laundering, conspiracy to commit fraud and other unsavory names. We called it smart, efficient investing.

Joe was the top earner in our Division and I was his golden boy assistant. His clients were organizations, companies and individuals who wished to make investments around the world without attracting attention. Here's an example. Picture a company that wants to buy another company here or abroad but for whatever reason they don't want to publicize that transaction, the new ownership or maybe even the flow of funds used to make the purchase. Picture a politician who is a crusader against the oil industry who sees the profits and wants to buy a fracking company. Picture a wealthy man who wants to conceal major assets from a cheating wife. Picture me soaking up this knowledge for ten years from the master and then going out on my own. I rented a small suite with a shared secretary. With Joe's cooperation, I started with a handful of very lucrative accounts and built from there.

After being so thoroughly exposed to the darker side of "legal" Investment Banking, I had become just as jaded and untrusting of others as had been my mentor. I now knew and used all of Joe's tricks and techniques to invest for my customers and on the side for myself. On the record I had a comfortable salary of 200k+ with great benefits. Off the record I had, through shell corporations, straw purchases and tax avoidance, created an off shore alter ego that was worth $10m and growing. Celia was not aware of Mr Alter and I really can't explain why I never told her about him. I didn't have any reason not to trust her but I think because of the sort of shady kind of dealings and complex hard to understand processes involved, I just kept these things to myself. She did however know everything about my on the record finances and I hers. She made about the same as me and had similar benefits with the University. Together we were comfortable even though living in NYC is expensive. We were able to take some nice weekend trips and an annual excursion to someplace warm and sunny in the winter. We each had our own credit cards, savings accounts and retirement 401k's. Each of us also had a generous payroll deduction deposit into our joint checking account for our common expenses like rent, food, utilities etc. Any surplus would go towards buying a joint CD, pay for a vacation or make a stock purchase.