Swinging Goes Awry: Beginnings

As Winston cleared the last of our plates, he asked “Are you two going to selection tonight?”

“Yes.” Mandy replied.

“Excellent. I look forward to seeing you there. I just have to change before I go.”

“Oh, are you one of the guides?” Mandy asked.

“Guides?” He said, looking somewhat perplexed. Then his face cleared. “Ah, yes. I suppose I am a guide, of a sort.”

“So do we get to select you tonight?” Mandy said with flirtatious eyes.

“Oh no, Mandy my sweet. Here the guides select the couples.” He smirked.

“What if we don’t like our guides?” I asked.

“Well, that has never happened, so I suppose you would get your money back, but you should trust the process.” Winston replied. “I must take these plates away and get changed, so I will see you two in a bit.” Winston left us to our own devices.

“They choose our guides?” Mandy said to me.

“I guess so. I didn’t think that was going to happen, but alright.” I replied.

“Well, I hope we get Winston, he is delightful.”

“He is very nice. Don’t I get a female guide?”

“Oh, honey. I am sure there will be lots of opportunities. Heck, you could fuck… what was her name?”

“Who?”

“The woman on the bus?”

“Oh, Johnny’s wife?”

“Yes.”

“Ummm… Mel?”

“That’s it. Damnit, that was going to drive me crazy.”

“We might see them at selection, should probably remember their names.”

Mandy reached over and slapped my arm. “Fuck you, I remember names. I was too busy focusing on her getting fucked on the bus to remember her name.”

“Fair, that was pretty hot. I wouldn’t mind getting into some public sex myself while we are here.”

“Mmmm, that does sound fun.”

“Well, shall we?” I asked, indicating leaving the restaurant.

“Mmmhmm.” She replied.

We both got up and headed out. We thanked the staff for the meal as were leaving and headed out. The area around the restaurant was quite empty, which we suspected had to do with the selection event being soon. We headed in that direction.

We arrived at the open space near the main pool where the selection was going to take place. There was a stage set up in front of a large number of chairs. Most of the chairs were already taken. I estimated that there were around 30 chairs pointed towards the stage. As we approached, Johnny got up from one of the chairs next to his wife and came over to us.

“Brucey, Mandy, why don’t you two come sit with us?” He suggested.

“Sure.” I replied, more politely than enthusiastically. Mandy and I sat beside Johnny and Mel, with Johnny and I beside each other. We were pretty close to the stage.

“How was your day so far?” Johnny asked.

“Very nice. We didn’t get up to much. Just went to our room and then to dinner at the Jamaican restaurant.” I replied.

“That place is great. We have also been mostly in our room anticipating this event. Have they told you much about it?”

“Not really. They called it selection and we just heard that the guides select the guests that they will show around.”

“Yeah, that is basically it. Each selection lasts a week, so whoever you get tonight will be your man for the week. Pretty sweet, right?”

“I guess. Are they all knowledgeable about Jamaica and its traditions?”

“Of course. They are very well trained. Remember the guy from the bus who Mel fucked? He is only a trainee, so you can imagine how much more skilled the actual guides are.”

“Okay.” I couldn’t remember the guy on the bus telling us much about Jamaican traditions, but figured that he could have if he had been asked.

“Oh. Here we go.” Johnny said as he pointed to a stunning, tall, blonde woman dressed in a gown approaching the stage from the side. Music started coming out of recessed speakers in the area.

“Who is that?” I asked, leaning over so Johnny could hear me.

“That is the Director, Britney. She is the best.” He explained. She certainly was worth looking at. She had long blonde curls, a slim but athletic figure, and very natural-looking large breasts barely contained in her full length light blue gown.

Everyone in the crowd started applauding as Britney ascended the steps onto the stage. I could see that she was wearing a microphone on a headset, one of those clear plastic things that musicians sometimes wear. She moved to the front of the stage and bowed to the crowd.

“Welcome, welcome, queens and your boys! Welcome to paradise!” Everyone applauded again. As the applause died down Britney began speaking again. “For some of you, it has been too long, and for others, it feels like you only just left. And for a very select few of you, it is your very first time.” She looked directly at Mandy and I for a moment and then looked over to another couple as well.

“For those of you that are new, let me lay out the ground rules. The first rule is that you are here to have fun, so have fun. Please leave any and all sexual or emotional hang-ups back home where they belong. This place is for freedom and exploration. The second rule is that the men make the choices. If you don’t want to do what they say, then you just have to say no. But we all know that really, you want to say yes.” Another cheer erupted at this. “The third rule is: an open door means ‘come on in’.” Britney paused again. “The rest of the rules, you will figure out as you come to understand what it is to be in paradise.

“Without further ado, let me introduce the men who will be your guides.” Another round of applause. “Our first man is one who needs no introduction: the man many of you have been coming back year in and year out to try, our largest specimen in a number of ways and also one of our most experienced, Samson!” A roar erupted from the crowd, and Mandy and I applauded along with them as a massive black man came out from a clump of bushes and onto the stage. He was wearing only a Speedo, and even then, his dick barely fit inside it, stretching the fabric out and leaving a gap between the fabric and his abdomen. The man attached to that dick was huge. He must have been 6’7 and easily 300 pounds of solid muscle. His chest was a V-shape and his legs were massive. He was rippling with muscle and had clearly either pumped up before the event or had been lathered in oil, as he had a sheen on his body. He was bald with a handsome face and a salt and pepper close-cropped beard. He appeared to be in his forties. Once up on the stage, Samson did a few poses to a number of cheers. The poses stretched out his cock in his Speedo so that the head was peeking out the top and Samson had to readjust before he took his position on the end of the stage.

Mandy leaned over to me. “Jesus Christ, that thing would split a woman in half!” She laughed.

“I know, fucking absurd. Could anyone enjoy something that big?” I laughed back.

As the applause quieted down, Britney made her next introduction. “Our next man is one of our newest additions, and also one of our youngest, but very skilled, please welcome, Julius!” Another black man approached the stage, also wearing a speedo, very young-looking and much smaller than Samson. He had short-cropped hair and was athletic, but not large, as if he mostly did calisthenic workouts. He looked like he was fresh out of high school. His speedo was quite full as well, though you could see the outline of his long penis within, as if it was a garter snake. He jumped up on the stage and did a bit of a dance to some cheers.

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