Swinging Goes Awry: Beginnings
Dive into “Swinging Goes Awry,” a tantalizing gay sex story that explores unexpected connections and thrilling encounters. Join the adventure as desires clash and boundaries are tested—perfect for readers seeking a passionate twist on swinging!
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.