Part 10 -- The Girls Go to the Islands

 

It's probably not the best idea to get a new camera before going on vacation but I found a used Canon FTb at a camera store for only $75. It was 25 years old, but I planned on using it with black & white film and it meant I wouldn't have to beg my dad to use his camera. The purchase did mean that I needed a bigger camera bag, I found a nice backpack at a thrift store that would work for me and also have enough room for some clothes and things like that.

 

Rita told us that Jan tended to over-plan things, but for someone who would probably go to work in the shipping business that's not a bad thing. The way the flights worked we would have to spend the night in Toronto and so, instead of having to sleep on the floor in the airport, we would arrive early enough where we could get dinner and a hotel room near the airport. Rita warned us we would no doubt have to listen to the two of them fucking but I told she and Jan would have to listen to me and Lisa also. Jan had explained that our checked bags would be sent through to Sint Maarten and not leave the airport, so we would only have to carry our overnight bags through Canadian customs.

 

Our original plan was to take the train to Chicago and then a Metra train to O'Hare; but Amber had a simpler plan. She was leaving Saturday morning for her home in Wisconsin and she was willing to drop us off at the airport and that would save us a lot of time. Friday night I went over to Lisa's dorm to spend the night, dragging all my gear and luggage, mumbling about me inheriting my mom's tendency to overpack.

 

When I went into the room Lisa was on her knees between Amber's toned thighs, licking her roommate's delicious brown pussy. I got my shirt off so that Amber could play with my boobs and raised her legs a little so that I could get at her butthole as well as her pussy. We were relentless fucking our friend, driving her to orgasm after orgasm. We took turns sitting on her pretty face; Lisa experienced a very juicy, gushing orgasm, soaking Ambers black hair; I actually fell off of Amber, falling to the floor moaning and writhing, my thick legs shaking and kicking. I tried out my Polaroid camera, taking several shots of the three of us with our legs spread wide; they photos weren't Playboy quality, but Amber assured me it would provide her with many pleasurable nights of pussy rubbing while she was at home.

 

We got breakfast before we left, Lisa was happy there was French toast; but she admitted that mine (and even my mom's) was better. I got a nice big to-go cup of Darjeeling tea, it was cold and damp that morning and I was already longing for the warm Sun of a tropical island. We promised Amber that someday she would get to meet Rita, and maybe Jan as well. Amber did tell us some spring she wanted us to come with her back to the reservation someday. There was a big celebration and dance party every year and she promised us we could watch her practice her dancing while she was naked; we liked that idea.

 

Jan and Rita were waiting for us at the Air Canada counter. We were happy to see Katherine and Erin there, they had driven them to the airport, and they both blushed when me and Lisa gave them each a big hug. Lisa tends to get annoyed with people who she sees as bossy. but she gave Jan a break that day because he was the one who knew what needed to happen and where we needed to go. He actually had a checklist that he went over; I looked over at Katherine and saw that she clearly approved of his diligence. If he could win Katherine over to him his chances of actually getting serious with Rita were much improved because Katherine would no doubt pass on her opinions to Mrs. G.

 

I let everyone else check in before I did; I wanted to see what the process was so that I didn't look like a total bumpkin (it's one of my great, recurring fears). I breathed a sigh of relief when my suitcase weighed less than 70 pounds (damn you and your overpacking Mom!), I showed the agent my passport and my ticket and I got my boarding pass and we headed to security. Remember, Dear Readers, this was in the days before 9/11 so security was not nearly as cumbersome as it is today. We found a place to sit at our gate and I did my best not to present the image of a girl who has never been in a large airport (or really any airport) in her life. I was holding Lisa's hand tight as we boarded, I was in the window seat and she was in the middle; she knew I really wanted to look out the window. Once again, she helped me fasten my seatbelt, actually biting my tit in the process (I giggled). One of the flight attendants smiled when she saw me holding Lisa's hand; she was quite pretty but I was too nervous to think a lot about sex.

 

The flight to Toronto was not a long one and I spent the entire time looking out the window; Lisa was leaned up against me, her cheek on my shoulder. I did get some more tea and I was even brave enough to try to pee on the plane. Going into the restroom I could not believe that some people fantasize about sex in one of those; it was about as romantic as a construction site Port-A-John. Lisa was pleased I did not want her to join me.

 

We landed and got off the plane, heading for the hotel that was attached to the airport. Jan was using his parents reward points for the room, which would have two queen beds. To get there we had to go through customs and that had me shaking from nerves. Lisa was nervous too, she had never left the United States either. Jan and Rita went first, and we listened to what they said so that we could basically say the same thing.

 

I handed the guy at the desk my passport and tried to be calm and smile; out of nervousness I was very formal and polite to him (that never hurts). He was all business, but he was also trying to be nice to me because he could sense my unease. By now he knew the plan for our group and he sent me on my way with a cheerful, "Enjoy your stay in Canada Miss Manning."

 

The hotel was part of the airport, so it was just a short walk to get there. Jan checked in and we took our bags, small though they were up to our room. We were pretty high up and I was totally mesmerized by looking out at the window at the city sprawling off toward Lake Erie. I had been to the top of the Sears Tower and the Hancock Center in Chicago, but only in the daytime; seeing a city lie Toronto at night was something totally new.

 

Lisa came up behind me, putting her arms around me and sliding her hand up under my shirt, "It's amazing, isn't it sweetie?"

 

I turned around, grabbing her firm butt and pulling her in close so our boobs mashed together. "Pity we're sharing the room, I'd love to fuck you right in front of the window." That got me a smack on the butt from Rita.

 

We had dinner downstairs and headed to the hotel lounge, taking advantage of Ontario's lower drinking age. I got Lisa a glass of sherry (she loves her strong wine) and I was happy the bartender (a very cute, chubby brunette) could make me a Dark & Stormy. Normally I find people who think they know everything to be somewhat annoying but in Jan's case I was OK because I wanted to know about the place we were going to, and he really did know a lot about the island.

 

He told us about the history of the island, going back to the days of the West India Company; he made some mention of his family's connection to the Company, but he clearly didn't like talking about it. I could see why; the Dutch West India Company had made a mountain of cash in the slave trade and Jan really didn't like thinking about the money that had given him such an amazing life and so many opportunities being founded on one of the greatest evils humans had ever inflicted on one another. He said we would go to the French side of the island too and, looking at me, we would shop for dark rum. He told us about exchanging money; dollars will work everywhere but guilders (or francs) tend to get you a better price; food, flavors from all over the Caribbean and all over the world (I was already hungry); and a reminder that we needed lots of sunscreen.

 

"So, we can be naked on the beach?" My excitement was clear on this, but Jan did set me straight.

 

"Yes, there are clothing-optional beaches, but you have to realize the people on the beach are not all porn stars; most of them look like regular people. Imagine a beach filled with naked versions of your parents." That threw some cold water on me. "It's not sexual for the people there, you can't just fuck on the beach; in fact, it is considered very rude for guys to have an erection on the beach."

 

Rita put her arm around him, "Jan will have a problem there, you'll see."

 

"Anyway," he said, playing with Rita's dark hair, "Once you are far enough out in the water then you can get your freak on, just don't be too loud."

 

It was weird sharing a hotel room, though it was certainly better than sleeping on the floor at the airport. Lisa and I were kissing quietly and rubbing our bushes together. We could hear Rita and Jan going at it and they were definitely not embarrassed that we knew how much Rita liked his cock. Our orgasms were quite tame by comparison and we went to sleep snuggled close together.

 

After breakfast, not a very big one I must admit, we were at our gate. Lisa let me sit by the window again and she was in the middle. Lucky for her the aisle seat was taken by a little girl, probably about 10, so she had some room. Naturally the girl asked about Lisa's hair and she was very patient, as she almost always is with little kids, explaining it. Sandra (the girl) and her family were staying on the French side and she was looking forward to snorkeling and seeing all the fish; the last time they had been there she had seen a turtle. I had to admit I was hoping I'd get to see a sea turtle too.

 

I was not nearly as nervous as I had been the previous summer, but I still gave a squeak when the pilots throttled up the engines and I felt myself mashed back into my seat. We both napped on and off, Lisa was leaned over on me holding on to my arm, her head resting on my shoulder. I excitedly woke her up when I looked out at the window and saw the ocean.

 

"Babe! It's the ocean!"

 

She gave me a quick kiss on the cheek, "It certainly is sweetie, I wonder where we are?"

 

Jan looked over the top of his seat, "That's the coast of Delaware, from here on it's a long flight over a lot of blue ocean."

 

He was right, it was hour after hour of nothing to look at but more water. I got up to pee and Lisa and I swapped seats so that she could lean against the window and I could lay my head on her shoulder.

 

About three hours into the flight Lisa woke me up, "Look, there's an island!"

 

"Hey Jan, do you know where we are?"

 

"Those islands are part of the Turks & Caicos, they're some British islands."

 

I though Jan was just some sort of genius, it turned out he was listening to the radio communications from the flight deck; it didn't hurt that he had made this flight many times. He told us that the flight from Amsterdam was way more boring; lots more ocean. I plugged my headphones into the socket in the arm of the seat and I was captivated listening to the flight deck crew. They checked in with air traffic control in Puerto Rico and then I heard them talking to the controllers at the airport we were headed to. A lot of it was chatter I didn't understand, but I heard the controllers tell them to begin their descent in to Princess Juliana (that's the airport) and I felt them throttle the engines down. It was hard to tell if we were getting closer to the ocean or not, there wasn't any perspective, but then suddenly I saw people on the beach and then seconds later the wheels touched down and we were on the ground.

 

As we waited in line to get through customs Jan told us about Maho beach, the one we had flown over, and how the plans are only a few hundred feet off the ground when they fly over the beach. I remarked that Granddad would love that, owing to his love of airplanes (and all machines). Jan, having a Dutch passport, got to go through much faster than the three of us. I was nervous, I always am when I don't feel in control, but everyone was very polite to us. We gathered outside and a car from the resort where the house is located was there to pick us up. It wasn't very far but traffic was awful; and I say this as someone who lives in Chicago. I described it as "chaotic" and every time another car got way too close to us Lisa would grab my arm, I was holding her hand tight. Jan, only partially joking, said if we had bicycles we could get to the house almost as fast as driving.

 

The house was part of a resort; as we drove to the house Jan pointed out the various restaurants and clubs, the swimming pools, the bicycle rental, and of course the beach. I was looking to see if I could spy any naked women; I didn't see any but a few were topless and that definitely made me tingle. We dropped our bags at the main desk (someone would take them to the house) and we went to get some pizza. It was getting late and Jan had big plans for the next day; he really loved the island and thought of it as a second home. I think he really wanted Rita to love the place as much as he did, and I could totally see them living in the tropics.

 

We walked to the house and checked it out. It had two stories, the first floor was a large living room with a bar and a small kitchen. We could eat in the resort's restaurants for breakfast and lunch, dinner we had to pay for. Jan said we could make our own drinks and I found some dark rum and ginger ale (not ginger beer, sadly) and some lime juice; I made Lisa a French 75. Upstairs there were two bedrooms with a nice porch, Jan called it a veranda, that went around three sides of the house so we could lay in bed and look out over the ocean; it was quite the view.

 

Lisa and I had actually brought t-shorts to sleep in; this wasn't the law firm's house in Michigan where we could be naked all the time. I was sure we would get to hear Jan and Rita fucking (Rita gets loud) but we were OK with that. We stood out on the railing, looking out at the Moon reflecting off the sea with our t-shirts barely covering our butts.

 

I finished my drink and grabbed Lisa's hair, bending her over, "The Pirate Queen wants your delicious cunt wench."

 

"Yes, Captain, it's all yours."

 

I knelt behind her, pushing her t-shirt up, and spreading her firm legs wide so that I could run my tongue along her wet, yummy pussy and her butthole. She was really wet; all the talk of nude beaches had gotten both of us quite wound up. It took only a few minutes alternating with my tongue and my fingers before her tight butt began quivering and she let loose a gush of warm juices, making quite the puddle on the floor.

 

Now Lisa, now fully into her Mean Girl role, she pushed me down into one of the chairs and spread my legs wide so that she could tease my clit with her tongue while she slid two fingers up inside me. She held me in the chair as I thrashed around, I'm sure the noise carried across the next few houses. Lisa got in bed, but I was still looking out over the ocean, totally mesmerized by it, when I saw the star.

 

I went and got my camera and set it up on the veranda, Lisa got up, putting her t-shirt on, still half-asleep.

 

"What's so exciting sweetie?"

 

"See that star, the bright one just barely above the horizon? That's Alpha Centauri, the closest star to the Sun. I promised Dr. Hirschhorn I would get a photo of it for him."

 

Lisa patted my butt, "You're a good friend to Dr. Hirschhorn; I think he considers you to be a new granddaughter. Now come to bed baby, we have a big day tomorrow." She walked back to the bed pulling her t-shirt off, her pale butt practically glowing in the moonlight. I took then hint and jumped in bed with her, holding her tight with my boobs pressed against her back.

 

I woke up a few times in the night from the sounds of energetic sex from the room next door. Rita tends toward loud orgasms and, from the sounds of things, so did Jan. I was content to lay there in bed with Lisa holding me from behind with her hands on my boobs. It was sometime after the Sun came up that I was awakened by Rita crawling into the bed. She rolled me on my back and spread my legs so that she could rub her big nipple on my clit. By now Lisa was awake and she was playing with my hair as I writhed and moaned and ultimately almost kicked Rita in the face. She moved over and gave Lisa a mighty dovefucking as well and being rewarded with a lovely wet orgasm.

 

She lay on her back between us, both of us sucking on her hard nipples and playing with her almost bald pussy. She gripped both of us by the hair, moaning loud enough that I was sure early-morning beach goers heard her joyous orgasm.

 

Once she caught her breath she sat us, "I really missed you two. Jan is great, don't get me wrong, and sex with him is wonderful but he's still has a lot to learn about a woman's body. Here's why I came over to see you, it wasn't just to fuck; I made Jan promise not to bring this up with you because I didn't want him to come across as pushy, but here's the deal, he really wants you two to join us."

 

I laughed softly, "I was wondering when that would come up. So where is Jan on the Kinsey scale?"

 

Rita thought for a moment, "I'd say he's a two or a three. He really like girls, but he has fucked a few guys in his life." Here she looked at me, "I know this may surprise you, but he's more attracted to you Cindy than he is to Lisa. I think the thought of wrestling you nude really gets him hard."

 

Lisa laughed and kissed me, "See, people notice you. It's not always me they're staring at, I've told you that lots of time."

 

"I know babe, I just have a hard time believing it."

 

"So girls," Rita continued, "What do you think?"

 

Lisa looked at us both, "I can't say I'm totally opposed to the idea, but it would have to be both of us."

 

I leaned over and gave Rita's big breast a nip, "I love you sweetie, but I'm just not ready for that. I'll go with the Magic 8-Ball answer, `Answer Hazy. Ask Again Later.' I'm not ruling it out, but I would want to watch him fuck another guy too."

 

"OK babes, I'll let him know. You two need to get ready, Jan says we're going to visit two more countries today. We'll meet you for breakfast."

 

We showered quickly, for us, which meant no pussy eating, just some boob rubbing. Lisa did insist on shaving my legs. I had tried; honestly, I really did! but I didn't do a very good job. She even trimmed my bush up a bit, "Can't have that lovely fur showing from under your swimsuit" she said, giving my clit a little rub.

 

We talked some about our conversation with Rita while I braided Lisa's hair. She had gotten a haircut before we left home; while I might love seeing her white hair all the way down to her butt she found the upkeep tedious and I just had to deal with that. We were both intrigued by Jan's interest in us and Lisa said she was open to the idea, but only if I was there too. I was really torn by the idea. The way I described my thoughts on the whole was that the idea of fucking a guy would be like getting fucked with our dildo. It's nice, I do get an orgasm out of it after all, but there's no romance there. I've way more interested in who the dildo is attached to and guys just done stir any passion in me at all. We decided to revisit the idea come summer and see how we felt then.

 

Breakfast was quite European; in other words, small; I sensed I would be snacking all day. There was an old Toyota Land Cruiser in the house's garage and Jan, who knew his way around the island, was going to drive. My first experience with traffic on the island (it's a densely populated place) made me glad to ride in the back seat with my sweetie.

 

We only had been driving a few minutes when we stopped at a sign that read "Bienvenue en Partie Française" (Welcome to the French Side) with a white line pained across the road. Of course I had to get my photo taken with one foot on each side of the line (me and hundreds of other tourists). I was wildly excited, I had read so much about the French colonization of North America and now here I was; technically I was now in France. Rita got a photo of me on the French side and Lisa on the Dutch side with us kissing across the line. Rita got Jan to blush (she really enjoyed doing that to him) suggesting that she wanted a photo of Jan on the Dutch side and her on the French side sucking his cock across the line. We so loved our dirty-minded friend.

 

Apart from the line on the road and the different license plates the French side looked exactly like the Dutch side. As we drove we learned more about Jan; he really didn't want to talk about his family's money (though there was obviously loads of it) but he did get really excited talking about global shipping. Rita let us know that their love of ships was the thing Jan and her dad had bonded over. We also learned one of the reasons Rita's mom and Katherine were suspicious of him; he was seven years older than Rita. When he had finished the Dutch equivalent of high school he had, much to the disgust of some of his friends and much of his family, decided not to go to college right away but had instead enlisted in the Dutch navy. He had spent four years in the navy and he had spent most of that time stationed on the island of Curaçao (which is down south, really close to Venezuela) on a ship called the Pelikan. It was his time in the navy that had caused him to fall in love with all the little islands of the Caribbean. He laughingly agreed with me that 300 years ago he might well have been a pirate.

 

Lisa, hoping to helpful, asked, "Do Rita's parents and Katherine know about your time in the navy?"

 

"No, I didn't think there was any reason to go into that."

 

"You should tell them, especially Katherine. I think that would help earn her respect." I nodded in agreement, appealing to Katherine's sense of duty was never a bad move.

 

We arrived in the town of Margiot, which Jan and Rita (she had been to France as a little girl) both said looked very much like a French seaside town and parked near the dock. J an bought us four tickets for the ferry to the to the town of Blowing Point on the British island of Anguilla. Waiting for the ferry we went to a café right along the water. I got several photos of Lisa, looking wildly glamorous, sipping her wine and Rita got one of the two of us (me with my Dark & Stormy. I told Jan I could happily stay at the café all day, but he said we had places to go.

 

We went to Anguilla mostly just to say we had been there. What was most memorable was the incredibly clear blue water in the channel between the two islands. Lisa had told me, quietly, that we needed to fuck in every country we visited. We found a secluded place in a park in Blowing Point where we could slide our hands into each other's shorts and finger our way to two very nice orgasms. After a few hours of walking around, and some more drinks, we boarded the ferry back to Margiot. As much as I would have loved to seen Lisa's hair blowing free in the wind I knew that it would have gotten horribly tangled and the de-tangling would not have been fun. I was sitting in a deck chair taking in the wonderful day when Lisa came and grabbed me, pulling me up out of the chair.

 

"Babe, come up to the bow!"

 

"What is it?"

 

"You'll see! Bring your camera!" Lisa was supremely excited, so I figured this was something good. It certainly way, in the bow wave in front of the ship there was a group of dolphins (Lisa said it was called a "pod") keeping up with the ferry, diving in and out of the water. I used almost an entire roll of film, hoping to get one clear shot (I wouldn't know until I got home).

 

Most of the afternoon was us making slow progress around the island. My constant need for photos, usually including Lisa (sometime Rita and Jan) definitely impeded our progress, along with Rita wanting to stop when we saw a nice beach to wade in the ocean. I admit, it was a wonderful feeling to be in such warm ocean water, very different from Lake Michigan. Jan did drive slowly along Orient Beach, where we saw our first nude beach-goers. He had been right, hardly any of the people looked like models or porn stars, most of them were just ordinary folks who liked being naked in the tropical Sun. That said we did see some devastatingly beautiful women and I could not help pointing out that some of them hadn't shaved their legs either.

 

It took us a long time to get through the town of Philipsburg on the Dutch side because of the traffic (the French side has fewer people); Jan pointed out some bars with Pride flags flying and said we could come back tonight if we wanted to. When we got back to the house we crashed for a little (OK, we fucked) before dinner.

 

Lisa and I were pretty quiet, we certainly weren't as loud as Jan and Rita. We sat out on the rattan couch on the veranda looking at the ocean and kissing (lots of kissing). We had enough privacy to get our tops off and we took turns sucking on each other's boobs. Lisa pulled my shorts off and tortured me for easily an hour slowly licking my pussy before she finally let me climax. I leaned her over the railing, if anyone had looked up they would have seen her beautiful boobs, and I licked her pussy and her butthole from behind; not stopping until she had left another nice puddle on the veranda.

 

Dinner was incredibly good seafood, being near the ocean makes that possible. We caught one of the buses (it was just a van) to Philipsburg; we would have been totally lost without Jan, I already admired his incredible sense of direction. We went to a bar just off the main street with a big pride flag over the door. Inside was mostly guys, a few who seemed to know Jan; we found a table and (the dinking age on the Dutch side being 16) went straight for a dark rum that was made on the French side (it was incredible). Lisa and Rita both got piña coladas (they love really sweet drinks). I was taking in the scenery, remembering Katherine's advice to always know your environment, while Lisa was dancing. I love dancing with Lisa, but her energy is almost limitless and sometimes I'm happy to just watch my sexy girlfriend. Several guys invited her to dance, she told me they were all complete gentlemen and "totally gay," and several girls as well. I knew Lisa could take care of herself, so I sat with Jan. Once he got a few beers in him he got really talkative; he grilled me all about Rita's mom and Katherine having deduced that they were the ones who he had to convince that he was worthy of Rita. To his credit he never brought up wanting to have a foursome with me and Lisa and Rita; Rita must had been very clear with him on that. By the end of the evening I knew that his true dream was to own one or two cargo ships and to make a living running between all the islands of what he called "The Windwards." I could see where that would be an appealing life, especially if you already had plenty of money.

 

The bartender, a very busty redhead who was shorter than Rita, announced the sign-up for Karaoke and Lisa was ready to go. I wasn't feeling bold enough for George Thorogood or Joan Jett, so I picked one of my favorites, The Kinks "Celluloid Heroes." Lisa went with Madonna's "Crazy for You", our duet of "The One That I Want" and (of course) "You'll Never Walk Alone."

 

I got polite applause for my efforts, Lisa performing Madonna had me, Jan, and Rita all pretty much masturbating in our seats. Our duet got the crowd going, especially the lesbian section when we got to the line "I need a girl and my heart is set on you" but she brought down the house with "You'll Never Walk Alone." That song will, if nothing else, let you know who the Liverpool FC fans are in the crowd and there was a very drunk group of guys singing along with her and they carried her around the bar on their shoulders (thankfully they didn't drop her) when she was done.

 

She and Rita had all the sweet fruity drinks they could handle, I was happy one woman bought me another rum. This woman sat down with us, a bit bleary and quite talkative. She introduced herself as Shawna.

 

"Where are you girls from?" We tried to explain the geography of Illinois (Shawna was from Rhode Island) but finally we went with "Just south of Chicago." Shawna told us she worked a theater in Newport, Rhode Island that had recently put on Carousel, the musical that Lisa's song came from, and that she hoped that someday Lisa would come out east. She also made it plain we would both have a place to stay; she had her hand on my thigh very near my pussy and I was feeling quite warm.

 

We stayed for a while, now having had enough that it was acceptable for us girls to be pawing each other. I looked over to the bar and I was pretty certain that a guy had his hand down Jan's pants. I mentioned it to Rita and got a slurred, "That's so fucking hot!" It was a good thing Lisa and I had fucked that afternoon because Lisa was out like a light, she didn't even brush her teeth. I curled up next to her and I was asleep pretty fast.

 

Before this amazing Spring Break the furthest I had ever traveled from home was Panama City, Florida so this was all so new for me. If you are liking the story I'd love to hear from you (cattingcindy@yahoo.com) and please consider a donation to the Nifty archive (https://donate.nifty.org)