The Biggest Mistake

A while ago I posted a story called Cuckold Landing, that tale was mostly fiction with some actual real life story in it. Part of the real life story included a situation that happened on one of our many trips to an infamous resort in Jamaica.

In one of the comments on the other story someone said they would love to hear more of that story. Like any story we need some background. Both about the situation and the players involved. Since it is about real people and a real event I'll have to fudge the details and names a bit to protect... well just to protect.

My wife and I met some twenty years ago when I was sent to her mill to train on a new process we were going to start up at my mill. We just clicked I guess and well you know how these stories go, we ended up doing a lot more than clicking and ended up in a long distance relationship for almost three years before I finally got a chance to move to where she worked and lived.

Carol was 5'4" and 115lbs when we met. She wore her brunette hair long and curly and well I guess big was the expression for it back then. Hey it was the early 90's and we were in the south so it wasn't unusual. She had deepest blue eyes that had me wanting to do anything she asked had me from the start. But the thing that kept me hard and wanting all day with her was her ass. I mean it was heart shaped, had the right rounded curves, and damn it looked so good in those tight grey slacks she wore the first day.

Me I'm Dan and back then I was 5'11" 180lbs and while not all muscle it was in pretty good shape. I am a bit shy with women and haven't really been all that successful but like I said we just clicked and soon I was flirting with her pretty bad and then I worked at trying to seduce her. I figured what did I have to lose since I would be leaving after two weeks and probably wouldn't ever see her again.

Since this isn't that story let's just say I succeeded and that it was worth all the effort and then some.

Fast forward a few years and we are living happily together in the mid-south and it's better than good. Sure there's stress from the job and her kids and all the other things people stress about but we are happy and still horny.

So about two years after we started living together we got to go on a cruise and had a pretty good time but the most fun was the day we spent in Jamaica. After that every time we discussed the idea of getting married it was always followed by a honeymoon in Jamaica.

So when we decided we were really going to do the deed I was looking for a place to stay for the honeymoon and found that if you stayed for seven days at Sandals resorts they gave you a wedding for free. At first it was kind of just joking but since we were just going to do a Justice of the peace type thing here at home we finally decided why not.

Then I go to book the wedding / honeymoon package and Sandals has changed their policy a bit. Now it's 500.00 for a wedding but the happy couple gets a free Royal Dalton china set. Now we are a couple blue collar workers in a small southern town and don't really care about China as table ware or the country really.

So the search begins anew. I soon find out that Superclubs offers a weddingmoon package that is just the ticket. Stay seven days, free wedding, gift basket, special dinner reservations, and the works. Now I just need to select a resort from the many offerings.

So being the over the top romantic type I am I went with the lowest price. I mean I didn't know anything about any of them and the services and facilities looked about the same. Heck three of them were on the same stretch of beach. So hello Hedonism II you are our winner in the search for the ideal honeymoon spot. Talked it over with Carol and she was fine with it, and yes I told her it was mostly price driven but she agreed most of the places looked about the same. Besides the name Hedonism just sounds really naughty compared to one named Breezes.

Then there was an awkward moment when I found out that Hedonism didn't just sound naughty. I discovered that we had booked not just our honeymoon but our wedding as well at an internationally known swingers resort.

Now most of what I know about swingers is from movies or stories about free love and such back in the 70's. What the hell am I going to tell my bride to be.

When we booked we knew there was a nude side and a prude side, well actually I think the room choices were Ocean View and Garden View with the same offerings in Au Natural. We had booked a Garden View room on the prude side and after discussing the whole thing decided it didn't matter what the others did we didn't have to do anything we didn't want to. Who knows we might even sneak over to the nude area and be crazy for a little bit, not that crazy mind you just a drink on the beach while naked.

So there's tons of plans to work out, we had to get copies of our divorces and birth certificates and all that stuff to send to the wedding coordinator. There's shopping too for sun dresses, bikinis, wedding dress, and even some PJ's because there's a pajama party one night in the disco and we think that might be fun to go see.

Finally it's time and we head off on our grand adventure. Both nervous as hell but to tell the truth the whole swinger aspect doesn't even make the top ten on the list. What if they didn't get the wedding set up or we are missing paperwork or... any of a hundred different scenarios took top billing to something as minor as being on a resort known to attract swingers.

Finally we get to Jamaica and check in at the desk in the airport. We are introduced to Bill and Paula since they will be in the same van as us for the ride to the resort. Now we knew as soon as we got to the van which side they were staying on. We had two large bags with a smaller bag as a carry on for stuff she just could not survive without. They had two small carry-on bags.

We talked a lot to them on the 2 hour ride to the resort and they seemed normal enough if you didn't dwell on the whole run around naked in front of strangers and heaven forbid even have sex with strangers.

By the time we got there we had made friends of a sort with them and agreed to meet them at dinner and such over the week. We figured it would be nice to have a couple that had been there several times before to show us around and all that even if we didn't follow them to the nude area.

Now given the title of this tale and this little bit of narrative so far you may be thinking that Bill and Paula ended up being the biggest almost mistake. No they were not, but they may have been somewhat of a gateway into the mistake.

What they were was a genuinely nice couple that did show us the resort, introduced us to many of their friends and even ended up being the witnesses at our wedding. Said wedding was better than could be hoped for by the way. Beautiful garden area near the ocean warm sunny day and just about the most relaxed setting ever conceived for a wedding.

It didn't start out that way at first though. First hurdle was they didn't get any of the paperwork and didn't even have us scheduled to be married. We had copies of all the paperwork so no big deal there. A little scrambling by the wedding coordinator and we were booked for Thursday afternoon. Our wedding coordinator was from Canada and just working there for 6 months. Oh and she was a very attractive woman to boot. I wanted to check on the wedding plans several times a day but she assured me it was all fine.

On the big day just a couple hours before the wedding it clouded up and decided to pour rain. So the wedding party was all gathered in the piano bar drinking champagne and waiting out the downpour.

Just a few days earlier if you told me I'd spend the afternoon with two couples that were swingers and not only not be offended but actually enjoy their company I'd have said you were nuts.

But it was a good time, no pressure from them to engage in their private games or anything like that. We just talked about stuff normal everyday couples would. Drama with the kids, our jobs, hobbies you know just stuff. All together there were eight of us in the bar Carol and I of course, Bill and Paula I've mentioned already, Jim and his Wife Nina, a photographer and the ever so cute wedding coordinator.

While waiting out the rain we had a bit of champagne and it was the first time I discovered how that effected by normally beer drinking bride to be. Nothing bad mind you but it does go to her head rather quickly compared to her usual beer. So we talked and drank and we learned a bit about our new friends.

Fist was they didn't like the label swingers. I guess it just brings up the whole 60s free love orgy scene many people associate with it. The term is "lifestyle couple" but that can mean so many things so there's further definitions like full swap, soft swing, and a dozen other different well let's just call it comfort levels.

For example many of the couples we met would not play out of sight of each other. This is partly for safety reasons and partly for voyeuristic reasons. Others might allow their partner to go off alone. And many are couples where the woman is bi-sexual and she plays only with other girls and the guys stay with their own partners.

It was an education to say the least and in another setting might have seemed a bit strange. But being where we were and when we were and having a bottle or three or champagne is was all okay. It seemed almost normal in many ways. Most of the couples we met were just open and friendly and well seemed to be connected to each other. This trip was our first exposure to the lifestyle and at the time we had pretty much figured it would be the last.

Another notable thing before we finish our wedding afternoon was while walking around the resort to take pictures we noticed most of the people on the "prude" side were watching us and generally just commenting among themselves about it. Positive or negative we didn't know and pretty much nobody talked to us as we passed.

Then we crossed the magical line that separated the sides and suddenly people were smiling and offering congratulations as we passed. Passing the nude volley ball team became a photo op and we still have a picture us in our wedding attire surrounded by naked people. Many people got out of their beach chairs and shook our hands. I mean it was a night and day difference in attitude.

Our wedding reception was a toga party emceed by Jim and he introduced us to the whole resort. Following the dancing and some more drinks we ended the night by finding a remote spot on the nude beach and consummating our wedding under the stars. That alone was worth the price of admission folks.

With Tree frogs serenading us and relatively cool night air laden with salt from the ocean combined with the sounds of reggae music from the pool side bar all worked to make a magical moment for us.

We did the pajama party and it was really hot being in a semipublic setting with Carol in her little purple lace teddy. She started the night with a matching cover up but soon we were dancing the night away with her lovely ass more accented than covered by a thin strip of lace.

We did get brave enough to visit the nude area on two more occasions other than the night of the wedding. The first adventure was late at night after more than a few drinks and it consisted of us getting naked on a chair near the pool as quick as possible and then getting in the water and staying neck deep the whole time.

But a funny thing happened once we were in. Basically nothing happened. We met some people had a drink and it was no different than a pool party anywhere you might find one, well except we were all naked.

So the wedding and honeymoon were awesome and we had a great time in Jamaica, so where is the mistake you ask...

Three years pass after the wedding trip and we are living a normal life in a small southern town. Kids the main source of drama as usual but life is good. We have talked about the trip of course over the years and some parts almost seem like a dream.

We have managed to save up a bit and it's time we travel someplace without the kids again. A return to Jamaica was always in the cards so we looked at the website and find out there is a brand new Hedonism resort. Hedonism III was only open or a year or less and since it was our third anniversary and Hedo III we figured it was fate of some sort.

This trip we knew more and planned a bit better. Also the new resort had a sort of middle ground area that was clothing optional. We booked a pool side swim up room in the Quad that surrounded the clothing optional area.

At Hedo II you are dressed or naked no in between. Sure most of the time you could go topless on the prude side if you really wanted but it was still against the loosely enforced rules. But at Hedo III in the quad you could easily have a couple that while she only wants to go topless he can be nude or any combination you care to imagine.

First day not much happened. Carol did spend a lot of the day by the pool topless and with her fairly new boob job she felt pretty confident. Guys you know that when a woman feels sexy she will act sexy and the sex gets better.

Don't get me wrong the sex at home on an average night is good, but sex after a night out dancing and flirting or in a hotel is always just a little hotter. So lying in the sun with her tits exposed to the heat of the day and the gaze of so many men did get her motor running pretty good. I was still hoping to make it to the nude side a lot more this trip than the last but it was up to her to set the pace.

The first night we met two couples at dinner that were from a nearby state. Funny you travel so far to meet someone just three hours from your home. Anyway we had a great time with them during dinner and afterward at the piano bar and later at the disco.

In particular Carol seemed to click with Dawn. They were each other's bad friend in just a matter of hours. You know the one your wife goes out for a girl's night with and you really aren't comfortable with it.

The next day finds us hanging out on the nude side with our newfound friends. From then on it's the six of us going and doing everything together. This trip turns out even better than the last and there's even more adventures thanks to our friends.

Highlight is another night by the ocean making love; well fucking is more like it really. There's a pier that goes out into the bay on the nude side that at night is mainly used to sex. Sure it's against the rules to have sex in public even at Hedo but that's pretty much a daytime thing. At night there are no rules.

So it happens that we are on the pier with our new friends, and two or three other couples that a little more than silhouettes in the dark. The sounds and smells of sex mix with the salt air and tree frogs with a clear sky and moonlight providing the mood lighting. Richard and Dawn are across the pier from us and I can see her riding on him. Carol is on top of me and slowly riding my cock.

I cannot find the words to explain how much fun that was. And while we were out there another couple comes out and takes the chaise lounge right next to us and begins to fuck. I have no idea who they are just that they were a black couple and she was riding him like a dime store pony. I mean they had the pier rocking in no time at all.

So I have the ever so nice feeling of my lovely wife's pussy slowly milking my hard dick and the visual stimulation of a very nicely shaped black girl getting fucked hard right next to me. I mean I could have reached out and pinched her nipple when she would slow for a moment. And yes the thought occurred to me.

By the end of the trip my formerly reserved wife was pretty much a confirmed nudist and we were hooked on the whole hedonistic package. We knew when we left that we would be back. Just didn't know how soon.

We met Richard and Dawn at their house shortly after we got back and over the course of the next few months things just got more fun and before we knew it we were booked to go back to Hedo in October.

So we went from three years between trips to something like 5 months. And that set a pattern that lasted for 4 years. Each trip things got a little more intense with more sex in public and even several times where we had sex in the same room as Richard and Dawn.

The girls became very close and had a great time picking out "slut wear" for the trips and planning matching outfits for all four of us in the disco for the theme nights.

Somewhere around the third or fourth trip there the girls were teasing me and Richard by lying in bed together and kissing and feeling each other's tits. And then they were not just teasing. I know it started as a game but it became their first time with another woman. Carol kept asking me if it was okay, seriously I'm standing there with a dick so hard you could pry a car trunk open with it and you're going to ask me that.

This did add a new dynamic to the games we played and it wasn't long before we would spend time with the girls taking turns pleasing each other while the guys watched. Of course there's always a little growth in situations like this and before long me and Richard were lying on either side of whichever wife happened to be on the receiving end of the pleasure and adding our own to it.

Basically it was just each of us taking a nipple to lick and suck while she got her pussy licked.

So we spent lots of time with our new style of play and it was so much fun. I have to admit it was a little strange the first time I realized Dawn was stroking both Richard and Me while we sucked her nipples, and odder still when it was Carol with a dick in each hand but the girls seemed to be really enjoying the games and it was all just natural reactions I guess.

Things went along this way for a while but like they say all good things must come to an end. We began to feel a little pressure from not so much Richard but Dawn to take things farther. At first it was just kind of light suggestions like Dawn would say things like "do you think you'll ever want to have sex with anyone else" or "Sometimes I wish I could feel what it would be like to get fucked and suck someone at the same time."

Soon the suggestions were not enough and she pretty much stated that if we didn't want to play that way she was going to find new playmates for her and Richard. And I thought well fine that's probably what you need to do. I was sure that Carol would feel the same way since we had discussed this very real possibility before.

The problem was that I had not accounted for how deeply Carol felt about Dawn. I know now she loved her as both a friend and lover and that the thought of losing her to another woman or couple scared her. The other big problem was that when Dawn did begin to act like she had found that other couple to play with we were at Hedo and had been drinking so it wasn't even close to the right time to be making decisions.

When the treat became real Carol went into damage control mode and pulled Dawn and the rest of us up to a room and started to play our usual game. At first it was the same as usual but I could feel things were not quite the same.

That was confirmed when Dawn came over to me and began sucking my cock. Now I'll admit it was fine with me to have a new set of lips on my dick. However it wasn't as fun when Carol started on Richard. But they seemed to have worked this out and I figured we would talk it over afterward and I'd tell her I think this should stay a one off deal.

When Dawn started to move up my body like she planned to ride me cowgirl I looked to see Carol in a similar position on Richard and I freaked. I stopped the play and I guess ended our relationship with Dawn and Richard.