Swinging Goes Awry: Beginnings

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.”

“True. Maybe I am making too much of it.” I conceded.

Just then, Winston returned with two large pina coladas. He placed them in front of us. “Please, take a drink. I want to know if I gauged your tastes right.” He said. Mandy and I took a sip. Mine was quite strong, just the way I liked it. I could see that Mandy also liked hers as her eyes lit up and she raised her eyebrows. We put out an “mmmm” in appreciation.

“Delicious.” I said. “And strong, just the way we like it.”

“I thought so. For dinner, may I choose as well? We like to help our customers by choosing things we know they would like, so we do the la familia style of food. Is this ok for you?”

Mandy looked at me and I shrugged and nodded. “We would love that. Please surprise us with some Jamaican delicacies.” Mandy told Winston.

“Oh, I certainly will.” He winked and left us.

Over the course of the next hour, Winston served us with a number of delicious local delicacies. We had crispy plantain and prawn tacos as an appetizer, jerk chicken as an entree, and a banana and taro dessert. By 6:30, we were very satisfied. We had also had a number of chances to chat with Winston and he was very friendly and flirty with Mandy. I was getting turned on thinking about my wife having fun with Winston and wondering who I would get a chance to be with.

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