Chapter 9: Caribbean Playground

Over the summer off from school and their graduate studies, the girls each got part time jobs so they could build up some job experience and burnish their resumes. Kat became gofer for a small contract marketing company that helped get small businesses known in their marketplace. Edie’s summer work was for a web developer, where she helped two other people develop content for their clients’ websites. Amber became an intern in the information systems department of a local manufacturing company that made avionics equipment.

By the end of August they were each ready to leave their summer jobs and return to school, motivated to complete their master’s degrees.

Throughout the summer, they continued to go on occasional ‘dates’. The summer season in Florida was not the busiest time of year for them. The out-of-town business trips that executives took avoided the searing heat and afternoon showers that frequented the Florida peninsula.

Each of the girls buttressed their relationships with their new boyfriends over the autumn: Amber with Mike, Kat with Brad, and Edie with Martin. At least every other week, Mike and Brad’s aircraft made a trip north and south with either the men or the girls inside depending on timing. More often than not, the girls flew up to Boston to see the two men, and often to engage in their foursome.

Over the Christmas season holidays, the girls fanned out to see their parents, and then joined their boyfriends for some fun and relaxation before winter classes resumed.

Amber lay in Mike’s arms. The two of them were naked and sexually sated after a morning romp in his large bed. They were watching snow flurries put an additional coat of whiteness over the Boston area through his bedroom window. Another foot of snow already lay on the ground.

“What are we going to do today?” Amber asked. “Play in the snow?”

Mike thought, “I need some R&R this week since the business is all but closed until the first Monday in January. I’m tired of cold and snow already, and it’s only late December. I was thinking we could go someplace warm– a place with sunny skies, water toys and sand, but not Sarasota. Further south, like some Caribbean island. Would you like that?” He looked to see her reaction.

“I’d love it. Anywhere you are is where I want to be, even here in this bed all week.”

“Then let’s do it.” He sat up on the bed more alert than ever.

Amber asked, “How about we take some of the others in our circle, like Kat and Brad? What were they planning to do this week? Also, I’d like to see Margo again and your parents; do you suppose you’d be willing to invite them? I’m sure we’d keep you busy.”

Mike thought a moment, “I love that idea. Let me make a couple of calls. I’d end up asking Margo to find us a place anyway. Having her come with us is even better.”

Amber teased, “It’ll be even better if she makes you cum too.” She reached down and took hold of his flaccid shaft and made a few masturbatory strokes. He knew she was teasing. After their night and morning, they both knew Mike needed some recovery time. She still knew she could provide some pleasure to him though.

Several phone calls and an hour later, they were dressed and packing. A few miles away the sleek Gulfstream 650 was being rolled out of its hangar and prepared for departure, and elsewhere at least five others were also racing around tossing bathing suits and warm weather clothes into suitcases.

Having been on so many upscale dates the girls traveled ready for about anything their ‘date’ might throw at them. Despite their travels that time of year to a wintery New England, they always carried some warm weather clothing and bathing suits. After all, a micro-bikini or two took up very little room in a suitcase. At this point in their escort careers, they knew they could also buy clothing almost everywhere they went.

Mike and Amber were the first to arrive at the airport. The taxi they’d taken dropped them at the door of the general aviation terminal. Ten minutes later, Margo appeared with a roll-on bag in tow, and looking enthused about the trip, but very professional.

Margo joined the pair and was surprisingly vocal and enthusiastic, “Wait until you see what I got for us. It’s a beautiful villa with lots of privacy. The staff of the place is preparing it for us now with provisions. They’re expecting us about four or five o’clock. I also have dinner reservations in Christiansted for tonight.” Margo was amazing in what she could get arranged. She’d formed an alliance with one of the travel agencies in the city and they’d do anything to keep her happy.

Amber heard Margo whisper to Mike, “The surprise you asked me to arrange is all set too. They were very willing.” Amber wondered who the ‘They’ were.

Kir and Jim appeared next, wearing winter clothing you’d expect at the North Pole. Lots of hugs and kisses prevailed. Last to arrive were Brad and Kat who’d come from his suburban town house. Brad was already wearing shorts, and looked peculiar because he also had on a heavy winter coat.

Mike had been talking to the pilots. He gestured and everyone pulled their luggage into a single pile, and then trooped out to the large corporate jet. A few minutes later the stairs were raised, doors secured, and the plane engines started. The light flurries continued as they taxied to takeoff on the long runway.

Mike and Margo met with the villa’s caretaker who’d waited for the group’s arrival. He gave them a rundown of the house and key points about living there for a week. Margo was taking on the role of ‘Queen Bee.’

Amber and Kat ran down a well-landscaped path to the beach ready to dip their toes in the water. After splashing into the Caribbean Sea up to their knees and then checking out the chaises and other beach furniture, the pair walked back up the path to the villa.

Just as they reached the Great Room of the house – the impressive cathedral ceiling living room, the door chimes sounded, a bit like Big Ben and just as august. Mike smiled at Amber and said, “Will you get that, Darling?”

Amber opened the door, and there stood Edie and Martin with huge smiles on their face.

The squeals and a million words passed between the two women in mere seconds as Martin and then Mike looked on a smiled at the close friends.

“What are you doing here?” Amber finally demanded, looking back over her shoulder at Mike.

Edie laughed, “Surprising you, more than we expected we would apparently. Margo explained what was happening, and Martin also wanted to take the week off, so we flew down here in his plane from Chicago.” Edie walked into the house, “This place is spectacular.”

Mike and Martin introduced themselves to each other as they came into the villa. Mike helped with their luggage, which they left in a pile by the stairway to the second floor of the large house. They hadn’t met, but both were well aware from stories their girlfriends had shared that the other man had sexual relations with their girlfriend. Neither mentioned those facts, but they did smirk at each other and nodded knowingly when they each saw Kat and the others welcoming Edie. Mike suspected that the subject would surely come up later.

Margo called the group together and announced that cocktails were about to be served poolside by the home’s caretaker, and then the group would be going off to dinner. She also stated that everyone had to dress and behave from ten in the morning until three in the afternoon because of the home’s staff being present to clean and maintain the house, but other than that we could wear anything or nothing as we saw fit. She also had a jitney picking us up at seven o’clock to take us to our restaurant for dinner.

Kat, Amber, Edie, and Kir grabbed their bags and went off to their assigned bedrooms and changed into their bikinis. They were back poolside in seconds, and swimming a microsecond after they converged. Mike and Brad joined them at a more relaxed pace, breathing in the beauty of the four women.

Martin and Jim also reappeared in shorts and flip-flops and helped get drinks for everybody, even those in the pool. Margo also reappeared dressed more appropriately for the islands in a sarong and wearing low-heeled sandals. She had a sedate one-piece bathing suit on too. The tenor of the group changed from formal to relaxed in those changes of clothing.

Margo looked satisfied with the small miracle she’d created that morning after Mike’s call to her. She’d rented a high-end villa for the week, organized the flight, set up the surprise with Martin and Edie, arranged transportation, and even made dinner reservations. The few loose ends, she’d contended with over the Internet and a satellite phone during the flight down to St. Croix.

After dinner and some wonderful rum punch, the group went dancing in a small club adjacent to the restaurant. There was a lot of mixing of partners, and Margo was continually but reluctantly pulled into the celebrating fray and the spirit that everyone enjoyed. The group was so excited and juiced up that they infused the band and the other dancers with their enthusiasm and love of life. The night was exceptional.

Eventually, Margo herded the partiers back into the jitney like a mother hen for the twenty-minute ride to the villa. During the ride, some interesting pairings were made. Amber ended up with Jim, Mike’s father; the two of them making out in the back of the small bus. Kat snuggled into Martin, Edie’s fiancé but someone she’d fucked several times over the past several months. Edie was with Brad, a first for her although she’d met the handsome man several times with her friends. Kir had latched onto her stepson Mike; and Margo briefly sat alone up near the bus’ front near the driver.

As the bus proceeded slowly over the bumpy country roads towards the villa, Amber came up to the seat opposite Margo. “Margo, please come back and join me and Jim, and stay with us after we get back to the villa. I want to make love to you again, and I’m sure you’ve met Mike’s father. We both like you and want to pleasure you.”

Margo looked slightly shocked. “I’ve never ... I’m not sure.” She looked deep into Amber’s eyes and confessed, “When you and I made love that was the first time, and then the weekend with Mike and you, well I’d never been in any situation with more than one other person. You’re so experienced ... and I really like you, but ... I just don’t know what it would be like with someone new and everyone would know what I was doing.”

Amber leaned in and kissed Margo. She took her hand and led her up the short aisle in the mini-bus and seated her next to Jim, and then sat on her other side. Both Jim and Amber put their arms around Margo and kissed her very tenderly. Margo ended the short journey looking worried.

The couples on the bus continued together at the villa, with each going off to various bedrooms but leaving the door open at the insistence of the girls in an open invitation to visit, join, share, or swap. Amber, Jim, and Margo went to Mike and Amber’s room where there was a large bed.

Despite the sex appeal that Margo displayed by way of a thin summer frock showing a fair amount of cleavage and CFM heels, she was nervous about being with Amber and Jim. He was especially sensitive to her feelings and tried to be as charming, sensitive, and empathetic of her feelings as he could be. Amber had long ago passed any feelings of nervousness in a new sexual situation, so she wanted to move ‘full steam ahead’ with her friend. She tried to moderate her full speed approach to seducing Margo.

Margo finally allowed Jim and Amber to pull the thin dress up over her body, carefully folding it over a nearby chair. Amber detached her demi-bra next, revealing Margo’s gorgeous curves to Jim and her, and giving Margo a shudder as a breeze from the window caressing her beauty.

Jim had been kissing Margo, and she’d participated most of the time despite her obvious nervousness. Through his new wife’s tutelage, he had become adept at locating and using to advantage the various erogenous zones a woman guarded. Margo wasn’t guarding anything, so he was having a field day around her face, ears, neck, and then her available breasts as he stroked her back.

Jim suckled on each of Margo’s small breasts, careful to not overdo the small bites and sucks. The moan he got from her signaled that what he was doing was ‘just right’. As he worked on her, Amber stood to the side and removed her clothing, soon displaying her buff body to the pair beside her. When Amber was naked, she moved to also kiss and fondle Margo, heightening further the sexual excitement for both of them.

Margo finally whispered, “Yesssss,” in response to the loving, gentle, and sexually-inclined assault Amber and Jim continued on her sexy body.

Amber kissed Margo’s lips and told her softly, “I promise you will like this. I promise that you will love every combination of people that make love to you this week. You are so beautiful and every person here wants to be with you, to have a deep and sexual relationship with you, and to bring you pleasure to every pore of your body.” The kisses that followed were even more stimulating and erotic.

Amber helped Margo shed her bikini briefs, and then led Jim and Margo to the large bed. Jim and Amber surrounded Margo and gradually as they both further toyed with her body, Margo took the initiative and started to touch her bed mates in intimate ways. Margo’s hand grasped Jim’s hardening cock and pulled and smoothed his passion. Her other hand snaked into Amber’s vee with two fingers sinking into the small woman’s vagina with equal passion to what Amber was doing to her. Margo’s reluctant compliance gave way to her active participation.

The trio played together for many minutes, bringing each to a brink and backing away. Jim eventually rose over Margo, and made love to the gorgeous woman as Amber watched and appreciated the new willingness to give herself over to a new lover. Jim culminated his lovemaking to Margo, and moved away, leaving her orgasmic body to Amber, who ensured several more breath-taking climaxes to her friend as Jim watched. Eventually, Jim serviced Amber too as Amber coaxed Margo into straddling her head so she could eat out Jim’s remaining cum from Margo’s sweet tasting cunt.

The trio cuddled together. Gradually, they seemed to fall asleep in the pleasure-induced coma a long and satisfying day had brought. Margo lay awake a long time thinking about the evening and what she’d done.

Amber awoke to the sun shining brightly on a palm tree just outside the bedroom window. Beside her, staring into her eyes with a smile was Mike, and on his further side Margo still asleep.

Amber smiled at him, “I love you.”

“I love you too.” He leaned in and kissed her.

“What are you doing here? I’m not complaining but I expected to wake up with your father; that’s how we went to sleep.”

“I’m here because I like Caribbean islands with pretty women on them.”

Amber chuckled, “I mean in bed with us? And, by the way, ALL Caribbean islands have pretty women on them.”

“Oh, that. I wanted to be with two women I love when they woke up.”

Amber teased, “I bet you love all the women here at the villa. You made love with Kir last night, and I know you love Kat and Edie.”

Mike smiled, “There is that too, but I love you two the best of all.”

They kissed again. Amber whispered, “Thank you.”

From Mike’s other side, Margo said in a throaty voice betraying her awakening condition, “Do you really love me, because you know I love you.”

Mike turned to put an arm around Margo and pulled her naked body to his chest as he did the same to Amber. “Yes, I love you, Margo. I always have.”

“But, our chemistry was off; I thought there were four things wrong. First,...”

“Just take what happens and don’t try to analyze everything like they taught you in business school. This isn’t the office. You’ve changed, and loosened up over the past year. The fact that you’re naked in bed with Amber after spending last evening with Jim proves it. Our chemistry is much, much better these days, and will get better with time.”

Margo reached across Mike and stroked Amber’s arm. She said, “That’s Amber’s doing. She keeps seducing me. So did Jim. Now I’ve slept with four men in my life.”

“I’m glad,” Mike reflected. “It’s made you more attractive and desirable.” He kissed Margo very tenderly. The love between then was palpable. Amber was glad.

Amber poked Mike in the side and teased, “So, what am I now, chopped liver?”

Mike kissed her and then again kissed Margo. “Nobody is chopped liver or any other thing other than desirable. I want you both. Can’t a guy like more than one girl at a time?”

Amber said to Margo, “He wants all the women in the house, so I think it’s only fair that we should want all the men, don’t you think?”

Margo sat up, “I guess if I’m giving it up to discover a new way of life that’s more pleasing to my boss, that’s the right attitude.” She looked at Mike for some kind of validation to what she’d said.

“It?” Mike questioned in a teasing tone.

Margo looked down at her hairy pussy. She pointed with one finger at her privates, “It! You know, my little cunny that you seem to like so much, or you used to. You’ve neglected it for the past weeks.”

Mike said, “I still like ‘it’ – a lot. I always will.” He sat up and kissed Margo, and then helped Amber into a seated position. He said, “There is a magnificent swimming pool just outside that French door. Come on. Time to wash all of last night’s sex away and start all over. Skinny dipping is the favored mode of swimming. Poolside sex is the recommended activity throughout the day.”