The Key West Vacation

Jim and Carol had been married for ten years and had not been able to take a vacation for the past five. Jim ran a successful contracting business in their New Jersey home town, while Carol was a stay-at-home mom, but also ran her own yoga gym part time. They met in college and wed just after graduation. Their two children came along four and six years later, respectively, and their lives had followed a steady, if not predictable, course.

Jim's business provided the bulk of their above-average income, and he never tired of reminding Carol and everyone else of that fact. Standing 5'9 tall and weighing over 180 pounds, he had definitely let himself go physically, but it did not stop him from coming across as a bully at times — particularly if he was drinking alcohol.

Carol's gym added "mad money" to the pot, and the steady workouts helped her recover her body shape quickly after each child was born. At 5'6" tall, 115 pounds with washboard abs, complimented by 36D breasts, Carol had ridiculously narrow hips for a woman of her age... especially one who had given birth to two children. She was the envy of every woman and an object of desire for every man. Her raven-colored hair came to her mid-back and framed a beautiful face, set off by luscious full lips and striking green eyes.

The couple had a beautiful home, which had been custom-built by Jim's company, and they both loved to entertain their wide circle of friends whenever the opportunity presented itself. During one such occasion in January, during the dead of a very cold winter, Jim proposed a February trip to the Florida Keys for everyone who could manage to join Carol and him.

"I am considering the purchase of a large vacation house on Key West, and we would love all of you to join us to get away from this absurdly cold weather. However, I want to be clear that this will be an adults-only trip — no kids. So, while Carol and I are planning to spend at least two weeks there, you guys can join in for as much or as little of the trip to paradise as you wish," Jim offered.

"How many of us can you accommodate?" one of the twenty party guests asked.

"Everyone here," Jim answered. "It has ten bedrooms and ten and a half bathrooms, plus two sleeper sofas. We'll need you to let us know by the end of next week, so that we can plan everything."

Jim's offer was a combination of him being magnanimous and a showoff at the same time. He suffered from a "Napoleon complex" because of his height, and overcompensated for it by pretentious displays of his wealth and his trophy wife. His offer had the desired effect, however, as the only topic of discussion for the rest of the party was the impending trip.

By the next week's end, Carol had received RSVPs from eight of the couples who had attended. "Well, it looks like our trip south is a hit with our friends," Carol reported to Jim. "I have everything arranged with the kids and the dogs for two weeks. Did you get the tickets?"

"Yep — we are going to fly to Fort Myers and then take a jet-powered catamaran to Key West from there. It's about a three and a half hour boat trip, which should be fun," Jim explained.

"OK, cool," Carol answered. "The couples will be arriving on different days throughout the first week that we are there. Looks like everyone will be at the property by Friday of that week and none has to leave until the following Tuesday."

The intervening three weeks went by very slowly, with mother nature making life in the Northeast even more miserable than usual by dumping several inches of snow on their town twice during that span. Finally, however, the day of departure arrived and the couple set off after goodbyes to the kids and pets. Arriving in Fort Myers, they were met by a limo driver who gathered their bags and drove them directly to dockside where the 160 foot Sunset Express Catamaran was waiting. With a cruising speed of 34 knots, it cut through the Gulf waters with ease during the three-and-a-half-hour trip. It had three decks of comfortable indoor/outdoor seating and a full bar, so the trip went quickly.

After docking in Key West, Jim picked up a custom rental Jeep that had a lifted suspension and removable top for use during their stay, and they drove directly to the house named 'Tropical Haven'. He had closed on the property two weeks earlier and had retained a local property management company to run it as a vacation rental whenever Carol and he were not there.

"Oh, honey, this is even prettier than I had imagined from the photos," Carol exclaimed to Jim.

"From the moment I flew down here and saw it, I knew you would love it," Jim responded. "I have already blocked out Halloween week down here for us. Key West is a wild place that week and I am really looking forward to it."

None of their guests would be joining them for the first three days of their stay, so the couple took advantage of the time to settle in and get acquainted with their new investment property. Tropical Haven came equipped with two full kitchens; two spacious living areas; ten private bedrooms, each with an en-suite bathroom. Add in two private pools and flat-screen TVs everywhere, and the result was a luxury accommodation with plenty of room for large groups.

Jim loved to show his beautiful wife off whenever the opportunity presented itself. He picked out many of her clothes and pressed her to wear outfits that showed off her body. As dinner time approached on their first night, he laid out items for Carol from some of the clothes he had bought for the trip. He began with a very short white denim skirt that was meant to be worn low on the hips. He added a pink tank top that was cropped to end a couple of inches above the bellybutton, and a pair of white sandals. "I would like you to wear this to dinner tonight," he said to Carol as she came into the bedroom after taking a shower.

"OK, sure," Carol agreed after seeing the outfit. "Any color preference for my panties?"

"I would prefer none," Jim suggested hopefully.

"I bet you would, pervert," Carol chided. "That skirt is so short, I won't be able to protect my modesty all the time, but I am not going to give people a gynecological view of my crotch. How about pink, to match the top? I'll bet guys will like catching glimpses of that."

"OK, fine, pink. But make it the really shear ones that I bought for you," Jim conceded.

As she pulled the tiny panties up her legs and over her hips, Carol noted that her small patch of pubic hair was clearly visible through the fabric. Her stomach did a little flip when she thought about a stranger getting a look up her skirt and seeing what she had on display. Donning the skirt, she worked to get it down on her hips so that the hem was at least a couple of inches below her crotch. The waist of the skirt was several inches below her bellybutton which displayed a beautiful expanse of her tight abs above it.

Not even bothering to ask if he wanted her to go braless, she slipped on the tank-top and looked at herself in a full-length mirror. The top was constructed out of a very thin material that clearly displayed the details of each nipple underneath.

"Other than a bikini, this is about as few clothes as I could legally wear in public — even in Key West," she thought.

After pulling her hair into a ponytail and adding a few jewelry accessories, including an ankle bracelet made from pieces of coral, Carol announced that she was ready to leave for dinner. As she was maneuvering the tall step up into the Jeep, she realized there was no lady-like way to get in or out of the vehicle. Anyone within eyeshot was going to know what color her underwear was, no matter what she did.

After a short drive, Jim parked the jeep just off Duval Street and Carol inadvertently provided a couple of passersby with a quick glimpse up her skirt as she dismounted from the jacked up vehicle. They walked a short distance to a bar right on the water near the famous marker that stood at the southern most point in the continental United States. Conch Heaven was a spot were both locals and tourist gathered. It featured live local musicians every night, a tasty seafood menu, and friendly bartenders that poured excellent drinks.

Jim selected two barstools that were on each side of a 90-degree corner of the bar so that rather than sitting next to each other, they were almost facing each other. He turned Carol's stool so that it was slightly sideways to the bar which put her legs in a position facing his side as well as the tables behind him. This meant, of course, that anyone sitting at the tables would have a crotch-level view of Carol's legs, which is what he had intended.

"See?" Carol said to Jim. "This is why panties were necessary. It doesn't surprise me that you have positioned me to entertain the crowd. I still don't understand why you like to do this kind of thing, though."

"It's simple, honey. I like to show off what a hot wife I have and I enjoy knowing that plenty of other guys wish they could have you. It really turns me on and I wish you could get a bit more into this kind of thing," he explained.

"Well, I think I have come a long way from where I was a few years ago, babe. It was very difficult for me to go from "mom mode" to hot wife. Plus, we know a lot of people that frequent the places we would go back home, so dressing like this was not something I was comfortable with back home. But, we are in the islands now, so I am ready to loosen up a bit, if you are sure that is what you really want," Carol offered.

"That is what I really want," was Jim's simple response.

"OK," Carol thought. "Let's see how this goes."

With that, she allowed her knees to part just a bit from their tightly clenched position. Her skirt was so short, having risen to where the hem was a little over an inch from her crotch, that even this slight adjustment provided onlookers with a glimpse of pink fabric. She lifted her gaze from her legs to the tables in front of her and saw that people at two of the tables were looking in her direction. At one table were two young boys, probably late teens or early twenties, who were unabashedly staring up her skirt. At the other there were two couples. Both of the men were looking at her slightly parted legs, while it appeared that the women were giving them grief for doing so.

"Well, I'm popular with the guys, but not so much so with the women," Carol said to her husband.

"Fuck the women. Most of them are already jealous of you anyway no matter what you do or say. Go with what works best for you while you have it. You are a thirty-five year old mother of two with the body better than most twenty year olds, so show it off and enjoy the attention you get from men. Let the wives and girlfriends stew in their own juices," Jim suggested.

There was truth in what he said. Even though Carol was a kindhearted and even-tempered friend to their female acquaintances, they really never accepted her as one of them. As far as they were concerned, she was the pampered, trophy wife of a wealthy snob of a husband. With that thought in her head, she parted her knees another couple of inches, which provided her audience with an unobstructed view of her full crotch. She pretended to be fully engaged in conversation with her husband — oblivious to the show she was putting on, but, out of the corner of her eye, she checked the attention she was getting from the tables.

The boys had actually repositioned themselves at their table to improve their viewing angle and were making no secret of their voyeurism. The women at the couples table, however, had reined in their men and were insisting they pay their check and leave. As soon as they departed, three older men took the table and its prime viewing angle of the hot MILF.

Another thirty minutes passed during which Carol shifted her position a few times. Crossing and uncrossing her legs; holding them tightly together (much to the frustration of her admirers) and then letting them drift apart again displaying a lovely view of her pink-pantied crotch. Jim was on his fourth bourbon by this time and was fairly well drunk when one of the boys approached and stood in front of Carol.

"Hi, you are beautiful. Would you like to dance?" He asked without hesitation.

"Sure, if it's OK with my husband," Carol replied with a glance at Jim who simply waved the back of his hand as if to shoo them away. "I guess that's a yes," she said as she slipped off her stool causing her short skirt to ride up even higher. Her new dance partner made no attempt to be a gentleman about the situation — instead he stood back a little and stared directly at her crotch to enjoy the view.

The young man took Carol's hand and led her to the twenty by twenty foot dance floor that had been built directly on the beach next to the bar. Once there, he pulled Carol to him and began to dance in sensuous Latin motions. He mashed their abdomens together and pressed her chest into his as he skillfully led her through the steps.

"Wow, you are really good at this," Carol noted.

"I grew up in Miami and I have been going to latin clubs since I can remember," he replied. "My friend and I have been enjoying looking at you and I just had to get closer to your fantastic body, so I asked you to dance."

"Well, this is definitely closer," Carol observed realizing that she could feel his hard-on through the material of his cotton pants.

He shifted his motion from a side to side rolling to a straightforward humping in time with the music, while moving a hand down to her left thigh just below her butt cheek to pull her in even closer. Basically, he was dry humping her on the dance floor.

Carol looked over at her husband and was disappointed that he did not seem to be paying any attention to them whatsoever. When the boy next pulled her left leg up so that it was next to his hip, she knew that a good portion of her ass was exposed and that her panty-clad pussy was now directly against his crotch.

Meanwhile, he had shifted his right hand from her back to the side of her left breast and immediately began to stroke it with his thumb, working his way closer and closer to her nipple. As she felt this, Carol glanced at her husband again. This time she saw that he was in conversation with the other boy from her dance partner's table who had seated himself on her barstool.

"I wonder what that is about?" she thought just as a jolt of electricity shot from her nipple to her brain.

Her partner's thumb had made its way to the rigid, nerve-filled target and had flicked it causing the sensation. At the same time, she felt a release of fluids from her vaginal canal in response to the humping of his crotch against hers and the stimulation of her nipple. And, now he was moving in for a kiss.

"Oh, shit," she thought as she turned her head away providing him with a cheek to kiss versus her mouth, but not stopping his thumb rubbing or crotch humping immediately. "This is moving from dancing to sex on the dance floor."

Moving away from him, she lowered her leg to the floor and shifted her left arm to move his hand away from her breast. "This has been fun, but I think I should rejoin my husband now," she told him.

"Sure, sure, sure," he quickly replied. "I hope my dance did not offend you."

"Not at all, I quite enjoyed it, but I am technically old enough to be your mother, so some of your moves would be better served with a younger partner, I think," she replied.

"I'm nineteen!" he countered. "And you are what? Twenty-five?"

"Try thirty-five and the mother of two, my young friend. Sorry," she informed him.

"Holy crap! For real? Wow, that makes you a MILF and the hottest one I have ever seen," he observed.

"Well, thanks, I guess. It's good to know that you would like to have sex with me, however inappropriate that would be," Carol smirked.

Reaching the bar, the other young boy exited her barstool and moved next to his friend as they both waited for her to mount the stool, which she did without the level of caution that she had used before. The result of her vaginal fluid release on the dance floor was an increased transparency of the material covering her vagina, which afforded the two boys an almost clear view of her lips, clit and pubic hair.

Feeling a degree of safety and comfort now that she was back in proximity of her husband, Carol left her legs a few inches apart to allow her admirers the show they were hoping for.

"That was a sexy dance you two were doing out there," Jim announced. "For a moment there, I thought you were going to fuck on the dance floor."

"Well, I guess he was paying attention," Carol thought.

"Sorry, sir. Your wife is just so sexy and such a good dancer that it brought out some very passionate moves on my part. I did not mean to offend either of you, sir," her dance partner explained.

"No need to apologize, my young friend and don't call me sir. My name is Jim. I actually found the dance to be very entertaining and I was disappointed that you two stopped. Doesn't my wife have a great body? I think it would be a crime to keep it under cover, don't you? That's why I pick out outfits like this one for her to wear. I like showing her off to other guys."

"That's great, sir... I mean Jim. Not many husbands would think like you do. It certainly makes it fun for those of us who get to see her," her dance partner said.

"That's what I like to hear! A little appreciation for my efforts! Carol, give these boys a better show. I've just agreed with Mark here to fund a boat trip with them this weekend. Mark tells me your name is Carlos, right? Well, I will provide the boat and you two will be our crew, if that is OK with you, Carlos.," Jim proposed.

Without hesitation Carlos quickly agreed. Turning to his wife, Jim asked, "Is that OK with you, honey?"

"Sure, I suppose it could be fun," Carol nodded.

"Great! It's settled then! Now, sweetheart, stop being so shy and give these boys something to look forward to on Saturday," Jim ordered.

Looking her husband in the eye, Carol slowly spread her legs apart. The excitement of the moment was causing a continual release of vaginal fluids from her canal and, as her legs parted, the liquid was visible on her panties and the stool beneath her.

Observing his wife's wet crotch, Jim said, "Well, it appears she really likes this. You can touch it, if you like."

Quickly recovering from the shock of her husband's offer to the boys, Carol snapped her legs together just as both of them were moving their hands toward her pussy.

"Looking is one thing, husband. Touching is something way past that. Not at all OK," Carol scolded.

"All right, I'm sorry. I was just trying to let the boys have a little fun," Jim disingenuously apologized.

"I'm sure you were, Jim. Now, it's time to get you home. Nice to meet you, Mark. Thank you for the dance, Carlos and I guess we will see you two on Saturday," Carol closed out the evening.

"Yes ma'm, Pier 5 at the marina - 9:00AM. I gave your husband my mobile number earlier," Mark said.

Carol drove the Jeep back to Tropical Haven and helped her husband get inside. His drinking had been getting worse over the past couple of years and his behavior when drunk was wildly unpredictable. Thankfully, this time, he passed out and slept it off until morning.

They both busied themselves with settling into their new vacation house and prepping for their visitors that would be joining them on Saturday. Tropical Haven employed a full-time staff of three, which made everything much easier for them.

The first of their arrivals were not scheduled land at the Key West airport until 1:00PM on Saturday and everyone else was due in on the next flight at 2:00PM. Jim had arranged a van to pick up both groups and drive them to the house. Carol was concerned about the boat trip scheduled the same day at 9AM, but Jim assured her they would be back in plenty of time to greet their guests.