My Big Mistake Pt. 01

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I invite my friend Joan to join us on vacation.
10.5k words
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Part 1 of the 3 part series

Updated 06/11/2023
Created 10/09/2022
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DawnR
DawnR
302 Followers

MY BIG MISTAKE

By Dawn Ramble

For those who love Saint Martin a memory of what might or might not have happened there years ago. All characters are over eighteen.

Part 1

A Short History

Where should I begin? I guess it was when George said we should go to Saint Martin again.

No actually I should start ten or so years earlier when we went on a Caribbean cruise with our good friends Doug and Joan Rivers. No, not the Joan Rivers, the comedian; she was not on our radar except when folks our parents' or more likely grandparents' age, chuckled at Joan's name. Actually, Joan's name when I first knew her was Joan Bailey. She just happened to meet and marry a guy named Doug Rivers. But I'm rambling.

The point was Joan and I had been best friends at an all-girls university in New York City. We both came from very conservative families although hers were Republican and mine were staunchly Democrat. That I suppose is why we found ourselves in such a place. No complaints about the education we received but I thought we had both missed out on a different education we might have been having at that age.

At least until our final year when we went on a ski trip in Vermont. There we met a couple of sexy ski instructors, who caught us up on some of what we had missed. I had lost my virginity in a rather messy encounter with a boy I barely knew after a dance the previous year, but it had all been drunken fumbling and over quickly. Joan on the other hand had been taking advantage of vacations since her sophomore year to gain some experience of her own. She'd told me briefly about these, but I had only half believed her.

These ski instructors, one was Austrian, and the other was Australian, spent their year moving between the ski slopes of Australia in our summer and Europe or the States in the winter. I didn't even know Australians skied. Anyway, two days into the trip we all ended up in bed together, and I had Joan to thank for that. I was willing enough but would never have had the nerve on my own. After that rather sad first attempt I admit I was more than ready to try sex again. I felt I was missing out on something.

I was! Joan and I were sharing a room, so there was not much of an option for privacy. I say we all ended up in bed together. There was one large double and one single bed. At first, we were paired up and trying to do our own thing. At least I was. Joan had other ideas, as did the boys. I say boys but the Aussie was late twenties and I'm think the Austrian was mid-thirties at least. It's hard to be discreet in the same bed and by the end of the trip there had been a lot of random coupling and my education had grown by leaps and bounds.

First, I found out that I really like sex, sometimes rough and rapid, sometimes sweet and slow. Then, I had my first orgasm and many more to follow. I found I had multiple erogenous zones on my body not just in my pussy and tits, although there were plenty there. I also found out that when I am extremely aroused, I am less fussy about whose cock in in me. At first, I felt ashamed by this discovery, but then it is what it is. I resolved not to get myself into those situations in future.

Fucking the students may be against the rules but I gathered it was a regular perk of the ski instructor business. My niece, who is in her early twenties as I was then, tells me it still is. They just have to be super-careful in this day and age that it is clearly consensual, or it is not just their jobs that are in jeopardy. My niece is my confidante about a lot of things, including some, but not all, of the things I'm about to share.

Joan and I are about the same height and there the similarity ends. I'm a brunette with perky breasts that fit nicely in some A, but more often B, cups. Joan is a blonde who amply fills her C cups. I have small areola and prominent nipples. Joan has large areola that cover the top of her expansive breasts, but her nipples lie almost flat. She insists they are still extremely sensitive. I know mine are. I'm generally somewhat shy, especially with people I don't know. Joan is loud and assertive and likes to be the center of attention.

My name is Holly by the way. After school we went our own ways. I took a government job in Albany and Joan wound up in Idaho. I met and married a man called George Bush. Yes, really, and so became Holly Bush. Speaking of which, she and I wrote Christmas cards to stay in touch and that's how we discovered a few years later that, both now married, we and our respective husbands had all found jobs in Washington, DC. We got together about once a month and that's when we decided to go on a Caribbean cruise out of Fort Lauderdale together.

I won't bore you with the details, but the point is one stop was in Saint Martin. We thought the island kind of cool because it is half Dutch and half French. We woke up to find everyone getting on lighters that ferried us to Philipsburg on the Dutch side. However, we had been told the best beaches were on the French side and there were lots of minibuses and taxis ready to give us a tour of the island or transfer us to Orient Beach. We opted for the beach and by nine thirty we were getting out of the bus in the car park next to a bar/cafe called Pedro's. It seemed more of a rudimentary wooden shack largely open to the elements which at the time were warm sunshine and a gentle breeze.

On the way over the driver had told us the beach on the right was clothing optional and the beach to the left required suits. Freshly armed with either beers or rum punches the group from our bus decided to brave the spectacle of seeing naked people. Together with the occupants of another minibus we set off like a patrol from the foreign legion over the sand and some in the group were visibly disappointed when we came to a sign clearly stating photography was not permitted.

Frankly, I felt like a bit of a shabby peeper as it was. It was clear that only the early birds had arrived as there were large areas of loungers that were empty and many of the nudists were strolling up and down the beach. I noticed that in our group most couples were hanging on to their partners as though they might be spirited away.

We turned round just before the end of the beach close to a restaurant named Papagayo. On the way back George suggested we refresh our drinks at the Perch Bar. I was still sipping my punch, but George and Doug were ready for another Heineken. We sat down and talked with an interesting lady bartender. I think she was called Willi. The rest of our group had kept going and were headed for the other part of the beach.

As we moved back on to the beach I wasn't entirely surprised when George suggested we stop here.

Joan said, "What take our clothes off?" and George just nodded.

"I suppose I'm OK with it if you guys are," Joan said, and in the same breath she pulled her top off, let it fall to the ground and shimmied out of her shorts and stood there in the slinkiest bikini I had ever seen. The bikini came off so fast I wasn't even sure I'd seen her undoing it. A nude couple nearby smiled and gave silent handclaps as she stood there a pastiche of tan and pale whitish-pink skin. The rest of us followed her lead rather less hastily while giggling nervously. We were all clearly newbies from the amount of untanned flesh we exposed, but we earned more silent applause from our nude neighbors.

George peeled off his clothes without hesitation and I saw he was a little chubby in the penis department, but nothing inappropriate. Being naturally shy I was a little slower, but I experienced a certain thrill as I slid my panties down to my ankles and stepped out of them. Doug was last and I drew in my breath as his shorts came off to reveal a very large bulge in his underwear. For a moment I thought he must be erect, but in the next he slid them off and I saw his large but flaccid cock unroll.

Soon we had paid for umbrellas and loungers and that's how we ended up spending a day naked at the beach. Everyone was very well behaved and the atmosphere, while possibly a little erotic for some, like me, who are not used to it, was not openly sexual. However, while nobody seems to be paying you the slightest bit of attention, I found it impossible not to look and was glad I had my sunglasses on to hide my wandering gaze.

When I took a walk after we had been sitting for a while, I noticed some women had their legs hanging either side of their loungers exposing every inch of their womanly parts. Those I knew could be quite varied, but I had never seen such a display before. Joan's pussy lips don't really show unless they are played with, whereas my labia are always visible. I had always been embarrassed by that but now I realized it was quite usual.

As for men I had never realized penises could come in so many varieties from super tiny enveloped in belly fat to long and lazy. That day, I only saw one man who seemed to be sporting a partial erection and he was drawing frowns from many of the nudists. I also saw some men, and women, with rings in various parts of their genitals. I learned later such things are not so uncommon, and there were tattoos, sometimes all over and sometimes discreetly in the most surprising places.

George has a nice penis. I think it may be a little above average size, but I continued to be surprised by Doug's flaccid cock. It was definitely large; maybe even longer and thicker, than George's erect one. I wondered if Joan found one that large painful or exciting. It certainly isn't George's penis that gives me orgasms. I guessed I knew her well enough to ask, but would I?

Around five o'clock people started to move off the beach. We caught a minibus back to the dock in Phillipsburg. Back on board we showered and got ready for dinner. At dinner we discovered some people had just toured the island and shopped. Some had been to a butterfly farm, and some had just stayed in Phillipsburg and shopped. As far as we could tell we were the only ones who had gone naked for the day but that was information we weren't really sharing.

George and I did share with each other how liberating we found the experience not to mention arousing. We fucked like crazy when we finally got bed, and I needed less attention than usual to have a really fulfilling orgasm. We woke up as horny as we had been the night before and we fucked again before showering and meeting Joan and Doug for breakfast.

I won't describe the rest of the cruise except to say there were no more nude beaches. However, George and I who were used to having sex two, maybe three times, a week could not get enough of it. We went to 'take a nap' after lunch every day, even on two occasions forfeiting the trip into port. By the end of the week George and I had decided we would come back and spend a week in Saint Martin, and the following spring that's what we did.

That was ten years ago, we are now in our forties, but from then on it has become a regular pilgrimage. Sometimes once a year, sometimes twice; sometimes one week, sometimes two. We have never engaged in any naughtiness at the beach, well maybe once or twice in the water. Overt sexual behavior by anyone was rare apart from the ladies who spread their legs. Occasional erections were more common than I had realized, but few men flaunted them. That was just what the British would call 'bad form.'

However, somehow, we always experience the same erotic tension that leads to great sex back at the villa. George has a strong sex drive all the time, an over-active libido if you like, and since that first trip to Saint Martin, we fuck almost every day at home. On vacation he just goes into overdrive. We do it in bed when we wake up, sometimes he'll be ready again before we even go to the beach.

By lunch time he often says, "The winds getting up, let's go back to the villa for lunch." The villa comes with a private pool, so we have a swim and a shower and somewhere along the way we do it again either before or after lunch or both. One thing about a private pool is it allows you to enjoy a change of venue for your sexual activity. After lunch we either go back to the beach or just hang out reading by the pool, but sooner or later if we stay there, he'll be feeling me up or holding a semi-erect cock in front of me asking if I'd like an appetizer. Before the end of our stay, I'm about done. George is relentless.

How has he got the stamina? Well, there has never been any suggestion of an erectile disfunction but at age forty-six he has persuaded his doctor to prescribe Viagra and it works like a charm. At least as far as he's concerned. I gather he's not the only guy using it as a recreational drug rather than to cure a known problem.

Over the years we had met with Doug and Joan quite often socially in Washington, but never again vacationed together. Sometimes we'd go out to a restaurant or a show and sometimes we would meet at their place or ours. We have made no secret of the fact we loved going back to Saint Martin and Joan often expressed an interest, but Doug said he had no interest at all.

Nevertheless, as they have a swimming pool in their backyard that is very private, a few times we have all gotten naked for the afternoon in memory of that day on the cruise. I don't mean we have ever done anything, just enjoyed being naked together. I'm always intrigued by the sight of Doug's large penis. It never seems to get aroused; George's does so easily. In their hot tub I have often felt the temptation to reach out and touch it, but of course I never have. I don't think Joan would worry as she's constantly flirting with George. Once early on, when his penis got a little chubby, she did reach out and give it a shake saying, "naughty boy," and we all laughed.

But I never got any indication over the years that Doug would welcome that attention from me. I wondered if maybe he didn't find me attractive, although he always seemed glad to see us. He's a delightful, educated man; funny and the perfect host and I had decided he was just shy like me. However, a few years ago I approached the topic of our respective sex lives by complaining to Joan that George is a little much, I gathered their situation is quite different.

She didn't really open up except to say he's affectionate, but they rarely have sex. I think his libido must be as low as George's is high. She once suggested they get it on with another couple to spice things up, perhaps even us, but he had zero interest. In fact, she said he was shocked at her suggestion. No wonder she likes to flirt with George, I think the pheromones just pour out of him.

That brings me back to where I started: to the summer three years ago when George said we should go to Saint Martin again. We planned our trip; we rented a villa for two weeks and booked our flight. That's when Joan called me to invite us to a barbeque at their place. Doug was going out of town on business for a month and she thought she might invite a few friends over. I told her we were sorry, but we had our trip to Saint Martin booked and she said lucky us. She would postpone the barbeque idea until we got back.

Then, out of the blue, I said why didn't she come with us. There was room in the villa, so she only had to find a flight and pay some share of the living expenses. I think my subconscious was already devising a plan that should work well for everyone, but more on that later.

No, better to say it now. Time to fess up, although it came from my subconscious, I quickly realized that my invitation to Joan to join us was prompted by a wish to share George's appetite with her. I was sure they would both be good with it. Joan, it seemed clear, had not been getting her fair share from Doug, possibly for years. Frankly, at least on vacation, I was getting too much. In that moment I thought a little sharing could be good for all of us.

When I told George that Joan would be joining us, he was surprised.

"Won't that be a little awkward?"

"She'll have her own bedroom."

"I know but we can be pretty loud, and anyway we do it in the pool or wherever we please."

That's when I had to come to terms with what had been circulating in my mind.

"What would you say if I said it would be all right for you to...to..."

"To what?" He was clearly confused.

"You know...you and she have always flirted...I think I would OK if you ...you know took it up a notch."

"You mean to have sex with her?"

"Well, not necessarily... but maybe...if you both want to. Apparently, she and Doug rarely have sex. I think I might have mentioned that once."

"I think you did, but I didn't really think it was any of my business. I just wasn't surprised."

"Why?"

"Well, I suspect he's gay even if he's still in the closet, as they say, but I could be wrong. As I say, it's none of my business," he paused, "Are you really saying it is OK for me to have sex with Joan or just some of what we used to call going round the bases?"

"Well, I guess I am," although now as I said it, I wasn't quite sure, "It's like one of those 'whatever happens in Vegas' things. I'm not writing a script, I'm just saying you know how perpetually horny you are when we're in Saint Martin, and if something happens, I'll be all right with it," I hoped I would...was this a big mistake?

He just looked at me and we said no more. I was a little stunned by his comment. It had never occurred to me that Doug might be gay. Knowing Joan's appetite for sex how on earth could she be all right with that. I dismissed the idea as foolish, and my mind returned to my decision. I wondered if I should have been so explicit or just waited to see if anything happened, but at least this way I knew that whatever happened it would not be construed as cheating.

Sunday

As it turned out, Joan was able to get on the same flight as us and we arrived at the villa in Orient Beach village after a stop at the supermarket for groceries and booze. We showed Joan around and gave her one of the two upstairs bedrooms. It was a bit late to go to the beach, so we all got naked and hung out at the pool. Joan was fascinated by an iguana playing in the coconut palm beside us.

Around five-thirty George opened the bar; that is, he made us all a rum punch.

"I'm going to shower," I said, as I finished mine.

"Good idea," said Joan.

There was just the one shared bathroom across from the two bedrooms and it had a large shower with a rain head rather than a tub. As we were already naked, it was simply a question of turning it on, stepping over the low surround, and pulling the curtain across.

"Memories of a ski trip," said Joan and I laughed as I handed her the body wash.

"Room for one more?" asked George stepping through the curtain.

"Of course," said Joan, before I could say anything.

We washed and turned to wash each other's backs and at some point, things got a little flirty and George washed first my breasts and then Joan's and she shamelessly reciprocated by carefully washing his penis. It, of course, quickly showed its appreciation of the attention.

We were only half dry when he pushed me down on the bed and we were at it. The door was not even fully closed, and I wondered what was going through Joan's mind. I did not bring her down here to torture her. But then George pulled out and switched to a sixty-nine-position feeding me a stiff cock covered in my juices, while he alternated between nibbling on my clit and thrusting his tongue into me. This is always a surefire path to orgasm for me and any other thoughts left my head.

We didn't talk after as we went downstairs. Joan was sitting on the patio reading. She had helped herself to another rum punch and George poured me another one. Then he pulled some pants and a shirt on so he could walk over to pick up pizzas. We had all agreed that after the flight down we would leave the fancy dining for a day or two.

DawnR
DawnR
302 Followers