Swinging Goes Awry: Beginnings

We had finally decided to take the plunge. We were going to try swinging. The wife and I had booked a trip to a swingers' resort in Jamaica for two weeks. We had been wanting to try swinging for a few years, but with our professional lives, we couldn't do it without risking our careers. For some reason, we thought that leaving town would make it all safer. We had heard of a great swinger resort in Jamaica through the internet and had researched it and thought it was perfect.

I, Bruce, was 34 at the time this happened. I was working as an accountant for a big firm in Chicago, so I didn't want any of my coworkers to know about my predilections. I am Italian by ancestry, by way of New York and Jersey, so we put bacon in our carbonara and garlic in our alfredo. At the time, I was 5'11, reasonably fit, though I didn't have a six pack or anything. I had been balding since my late twenties, so I had finally accepted it and shaved my head fully. I had a fairly hairy chest thanks to my background, with a treasure trail leading down to my five inch dick.

My wife, Mandy, was 26 at the time this happened. She had a fit, smaller body, at 5'4, and was quite lean. She had a nice bubble butt, though, which I always loved massaging and worshipping. Her hair was dyed blonde, which hid her Mediterranean ancestry, a mix of Greek, Italian and French. All of her fat went into her ass, so she had smaller breasts. She looked like a blonde Remy Lacroix and I was deeply in love with her.

Mandy had been a child prodigy and graduated high school early and college with a degree in engineering at 21 and started at a large civil engineering company after her practicum. She was smart as a whip, but because of her early finish, she had not had the same social opportunities as her fellow students.

I had managed to find Mandy on a dating website and we had gotten married a year later. She had a thing for older guys and being successful and our having similar tastes certainly helped. Our sex life had been great for our first year. Mandy was super kinky and always talking dirty in bed. One thing that really turned me on was when she would talk about us inviting other people into our bed with us, specifically other guys. I really loved the idea of seeing Mandy get fucked by other men and also I wanted to fuck some other women for variety.

Mandy had been a late bloomer in the sex department and I had been her first. She had an active imagination, but didn't have the experiences to match it. I had had a few partners in my life, but none that could match Mandy. As I wanted to broaden Mandy's horizons, we came up with the idea of trying out swinging. Because of our issues with our careers, we thought the only way to do it safely would be to take a trip to a resort where we were total strangers.

That is how we found ourselves on a flight to Jamaica in March for a two week vacation at a swingers resort.

"Baby, I am so excited!" Mandy said as we were taxiing to the airport in Montego Bay. "I can't wait to see the resort. It looked amazing in the pictures."

"I know." I replied. "Hopefully the people match what the website showed and it isn't just old people trying to rekindle their sex lives."

"Don't be such a downer, baby. I am sure we will find some people worthy of our attention."

"Alright, I will do my best." I replied.

We disembarked and went through passport control, eventually picking up our luggage. We followed the signs to the shuttles to the resorts and eventually found our resort's shuttle. We boarded with a pack of other couples and a number of single women in a group. The shuttle bus sat 20 or so, with two to each bench. Our driver was a handsome black man and there was a guide as well, also a handsome black man, both appeared to be in their twenties.

Mandy and I sat at one bench across the aisle from a couple who looked like older versions of us, with both men in the middle. The gentleman was an average looking man of middle-age, with dark hair streaked through with grey. He had a bit of a paunch, but not as much as some of the men that age that had given up. He looked to be a mix between Irish and Italian, so I figured he was from New York or Boston. As soon as he spoke, he confirmed my suspicion with his thick Brooklyn accent.

The New Yorker's partner was significantly younger than him, much like Mandy was to me. She looked to be in her early forties, but was very fit and attractive still. She had clearly had some work done on her face, but it didn't look fake or shiny, as some women do. Clearly her husband had some money to throw around if he was able to pay for plastic surgery that good. She was otherwise a classic blonde trophy wife. She had large breasts, which I suspected were fake due to how little they moved, a slim figure, and a tight ass. She must have spent a lot of time at the gym to maintain such a figure, which meant she didn't work much. She had a great smile and a pretty face, though I doubted that it had looked that way originally. She had thankfully not gotten lip fillers and had a naturally thin upper lip with a thicker lower lip.

The guide had us all checked in and situated in the bus before he directed the driver to head out. There was going to be quite a drive to get to our resort location.

"So where are you folks from?" The New Yorker asked me after we had left the airport parking lot and were driving through Montego Bay.

"Uhhhh," I replied, while looking at my wife. She smiled at me and nodded, so I responded "Chicago."

"The Windy City? Love Chicago. The wife and I make a yearly visit, ain't that right, beautiful?"

"Uh huh." Even with so few words spoken, I knew the trophy wife was from the South.

"We love it, for sure. Always check out the new scene with that food chemistry stuff, what do they call it?" He asked.

"Molecular gastronomy." I replied.

"That's it. And deep dish, of course. It may not be a New York pie, but hell, we are big fans nonetheless, ain't that right?" He again asked his partner.

"Uh huh." She again replied.

"So, how many times have you two been to Jamaica?" He asked.

"First time." I replied.

"Really? And your first visit is to this resort? During this season? Damn, you are brave. Honey, it's their first time." He said to his partner.

"Uh huh?" She replied, with a querying twist.

"Are you guys full swap or just soft swap swingers?" He asked.

"Well, we've never actually done any swinging, but we have been interested in it for a long time."

"You have never been swinging, either? Well, shit. You are our new favorite couple, right, beautiful?"

"Uh huh." She replied again. I realized that she was fixated on something at the front of the bus, so I looked up ahead and saw that she was obviously looking at our guide, who was speaking to the driver of the bus.

The New Yorker saw his wife looking at the guide and leaned over and whispered in her ear. She smiled in response and nodded to him. "Go on, then, baby." He said. His wife climbed over him, kissing him on the mouth, then headed up the aisle. "She wants to start early." He said to us. "By the way, I am Johnny." He reached over and offered his hand. We each shook it and introduced ourselves. "My wife is Mel, short for Melrose."

I looked to the front and saw that Mel was now speaking with the guide at the first row of the bus. "What do you mean by 'start early'?" I asked.

"We come to Jamaica for a particular kind of guy. My wife gets off fucking black guys outside of our marriage, pretty much exclusively. We use the whole interracial cuckolding thing in our fantasies a lot. So, when we are here, it is like a sexual smorgasbord for her. I basically let her run free." He gestured to the front of the bus and I looked again. Now Mel and the guide were making out hot and heavy. Soon she moved to straddle him and the bus erupted in cheers all around us. Mel lifted her fist to the sky and the crowd got louder.

"Is she fucking him?" My wife asked Johnny as Mel began to lift herself up and down in her straddling position. We could only really see her bouncing, as the rest was covered by the usual bench seating on a bus.

"Of course." He replied. "What else do you expect a dirty slut like her to do when she sees a beautiful man like that?"

"I don't know." Mandy replied. I looked over and saw that she was clearly enjoying what she was seeing as well.

"You let her just fuck the staff like that?" I asked Johnny.

"I let her fuck whoever she wants, Brucy." He replied. I didn't like that nickname, and I had heard it many times before. He could see my eyes narrow in response, but he continued smiling his privileged smile. "If I didn't she would do it anyways, so I might as well enjoy it."

At that moment, the bus entered a stretch of road that was quite beautiful, so Mandy and I were busy looking at the scenery for the next five minutes, though we both did make several glances over to the spectacle at the front of the bus. Mel seemed to be enjoying herself and was riding the guide like her life depended on it.

Eventually, the road re-entered a more densely forested area and we turned our attention back to Mel, who was riding her guide hard and fast until he grabbed her tight and pulled her down on him and we heard a guttural moan coming from the front. The other people on the bus once again cheered as Mel and the guide kissed passionately. Then Mel got off the guide, readjusted herself, top to bottom, and headed back to her seat.

Mel was all smiles as she approached the three of us. "Hey, hubby." She said to Johnny. "Hey, wifey." He replied. She kissed her husband on the lips and then scooted across him into her seat by the window.

I could overhear their conversation from my seat in the aisle. "How was he?" John asked his wife.

"He has a lot to learn, but he has the equipment to join the ranks of the real men." She replied.

"Did you save some for me?"

"Of course I did. Almost all of it. We will have to get to our room quickly when we arrive." I had no idea what half of their conversation meant, so I ignored it at the time. I would later reflect upon those words and how much foreboding I should have felt from them.

Mandy and I didn't speak with Johnny and Mel again until the bus arrived at the resort, a half hour later. Then it was just cordial farewells and "hope to see you later."

So it was that we ended up at our Jamiacan resort in the early afternoon standing in line at the check-in counter. Looking around, there were quite a lot of attractive people walking around the resort. The check-in area looked out over one of the pools and there were a number of young, good looking people on the deck and in the pools. Most were white people, with a few other ethnicities mixed in.

We finally were at the front of the line and a beautiful young East Asian woman waved us over to the counter. She was wearing what appeared to be the standard uniform for a number of the staff members, a black suit jacket over a white tube top with a short black skirt underneath and ropey sandals with exposed feet. Mandy and I walked over. "Hello and welcome to paradise," she said without a trace of accent and a large smile. She had a nametag that read 'Cindy'. "Can I get your names?"

We gave the receptionist our names and she plugged them into the computer. "Ah, here we are. Two weeks. And first timers?" She asked with her eyebrows raised toward us.

"Yes, that's right." I said.

"But experienced swingers, yes?" She asked.

"No, this is our first time trying it." My wife replied.

Cindy looked at us with her raised eyebrows for a few more seconds. "Well, I guess if you are going to do it, you might as well jump right in. I see that we received your bloodwork two days ago, so you are clear to go condom-free for the duration. All of our staff and visitors are regularly tested, so please do not worry about infections. In the ten years I have worked here, we have never had an issue."

She continued typing on the computer for a few more minutes and then handed us wristbands. "These are your wristbands. They are keyed to your rooms, so they will let you in and out, just tap it on the door. The button on the side there lets you give access to other wristbands, just tap it and then tap the wristband against the one that you want to give access to and they will be able to enter your room. Do the same thing once more and you will deny that person access. You can also hold it for 10 seconds and it will reset all access except your own. I see that you have purchased a suite with two bedrooms this weekend? Planning on having fun?" She said, smiling at me and winking at Mandy.

"Hoping." My wife replied. I smiled at her and Cindy.

"Good. Well, as it is your first night here, selection will occur at the main pool at 8:00pm, just after dinner." Cindy said.

"Selection?" We asked, simultaneously.

"Yes, all visitors are provided with one of our local... staff members who will keep you company and take care of your needs. Bruce, are you bisexual?"

"Sorry?" I asked, spluttering.

"Do you enjoy the company of men as well as women?" She asked again, more pointedly.

"Ummm... no?" I replied, confused by the question. I hadn't really thought about the prospect of men having sex with other men at the resort.

"You seem uncertain. I will put down a maybe for now. If anyone asks you to do something you do not want to do, you can always refuse. We treat consent and issues of sexual assault very seriously here." Cindy continued tapping on the keyboard. She eventually asked us for our payment information and we provided it. "As you know, everything is included here, but there are a few places where you can get additional expenses. They will always be clearly marked or you will be notified in advance. If you take issue with any of the services that you pay for, let us know. Tipping is totally banned here, and all of our staff are more than happy to assist with anything you need, free of charge."

Cindy reached down and pulled out a brochure. "Here is a map of the facilities. It also indicates the areas of the resort where you can get certain kinds of visitors. You will see that we are in the reception area here." She pointed to a spot on the map with a desk visible and reception marked. "The area from here to the beach is the clothed section. It is preferred that you do not linger in this area naked for long, but only pass through. If you need to go from one side to the other, please use the beach walkways, as clothing is always optional on our beaches. You will see that the North side is the full swap section in green, this is where your rooms are located. It is also where a number of events occur throughout the week. The pool in the full swap section is no clothing allowed, only robes. The other areas I am sure you can explore on your own."

Cindy then went through the different restaurants located at the resort and the spa facilities. "Is there anything else you need?" She asked.

I looked at my wife. She shook her head. "No, that should be everything." I said.

"Well, enjoy your stay here in paradise. If you need anything in your room, feel free to contact me directly." She smiled at my wife and I.

Mandy and I left and headed towards our room. Our luggage had been taken there for us already. On our way we passed by the full swap pool and saw once again that the average resident was young and attractive, unlike what we had feared.

We finally reached our suite and used our wristbands to enter. We were very happy with what we saw. There was a large bar area with an almost kitchenette, as well as a large living space in the central area. That led out to a balcony overlooking the full swap pool area. The living space was between the two bedrooms, with each having their own ensuite bathroom. There was also a smaller powder room in the central area. We checked the fridge and saw that it was stocked with beers and snacks. The bar area was stocked with a number of liquors as well as a fridge with mixing materials, like lime and lemon juice. It also had basic cocktail-making tools.

Each bedroom was fitted with a king-size bed with a light duvet and stylish sheets. There was also a couch facing the beds in each room. The ensuites were beautiful with full baths and windows facing outwards. The living area had a large television and a number of couches and was clearly meant for entertaining. Mandy and I unpacked our stuff into one of the main bedrooms and then changed into more suitable clothes for the locale. I wore shorts with a light cotton shirt and sandals and Mandy wore a light blue strapless sundress with sandals. As Mandy was getting dressed, I pulled her onto the bed for a quick fuck, dumping my load deep in her pussy in the missionary position as she came on my cock. We cuddled for a few minutes before having a shower and then redressing.

"What do you want to do first?" Mandy asked me. It was getting late in the afternoon now, so I suggested that we grab dinner at one of the restaurants before whatever the main event was. We took a look at the food brochure and decided on the place with the Jamaican cuisine. When in Rome, I guess.

We headed down to the restaurant around 6:30pm. It was a classy affair, with nice tables, casually dressed servers, and a band playing a number of instruments, including the classic steel drum. All of the staff were quite attractive and local. Mostly male, with a few females, like the hostess and the bartender.

We were sat at one of the tables looking out on the beach by the pretty dark-skinned hostess who informed us that our server would be someone named Winston. After a few minutes of waiting, an attractive, well-built black man walked up to our table in his tropical shirt and shorts. He was almost the spitting image of Lance Reddick, with a powerful chest, but still thin and tall. He did not have a bald-head though, sporting a more ragged-looking natural haircut.

"Hello, my name is Winston." He said in his Jamaican accent. "I will be your server this evening. We gonna take real good care of you two." He smiled at us both, with bright white teeth set against his black skin. "What are your names?"

"I am Mandy." My wife replied, putting out her hand. Winston did a slight bow and kissed her on the top of her hand and she blushed. "And this is my husband, Bruce." She indicated to me, not taking her eyes off of Winston.

"Hello." I said and shook Winston's hand. He had a firm grip.

"Welcome to Jamaica, Mandy and Bruce."

I looked at my wife and saw her glancing down at Winston's shorts, so I took a quick glance myself and saw that he was either packing some serious cock or he was stuffing his shorts.

"I get you two some pina colada's, okay?" Winston asked.

"Sure." Mandy and I replied, in unison.

Winston walked away. I turned to my wife again. She opened her mouth as if to say, "did you see that?" I nodded my head.

"Baby," Mandy said. "Would you be okay with me fucking Winston?"

"I never knew you were into black guys", I said. "Or that you were a size queen." I replied.

"I didn't either, and I don't think I am. But Winston is pretty cute and I wouldn't mind seeing what he is packing."

"It would be pointless to come here and not experience all this place has to offer. I just hope that there are some cuties for me as well."

"Cindy was pretty cute."

"Sure, but she is staff. I'm not sure that they let staff fraternize with the guests. And her question about me liking men kind of put me off a bit."

"Aww, is honey a little sensitive about his sexuality?" Mandy teased.

"No, I guess I just hadn't ever been asked that question before."

"It's a fair question. You know how we have read that some swingers communities don't like male homesexuality in their groups, even though they are perfectly fine with lesbianism."