Chapter 1

When I made the switch from working as a “customer” to being a “vendor”, I had no real understanding what the difference was. There were a lot of great people I liked working with, but some were over the top while others reminded me of sales people I didn’t like at all. One aspect I heard a lot about was “making club” where if the sales person overachieved their quota by a certain percentage, then they would get a three day vacation in a warm climate. I heard rumors about what sort of parties and outrageous behavior took place, but no one shared many details. Honestly, it sounded really cool, but it didn’t really matter since I was in Business Development, and we were not eligible.

That is, until the new head of Sales entered the picture. He believed that inviting a few “token” support functions would be a way of saying thank you to the whole company and encourage everyone to do more for the company. I guess I had been doing enough good things for the sales team that my name got thrown into the hat and then picked as the lucky winner. When they announced my name at the Sales Kickoff meeting and invited me up on stage, I was shocked. As I stood in the wildly cheering crowd, looking at all the others still waiting to find out if they made it, I just wanted to call my wife. There was no way she would hear me though, it was so loud.

“Honey, I have good news to share.”

“Really? I thought today was mostly wrapping up?”

“The rules changed a bit this year, and I was picked to go to the Chairman’s Club as a token representative for bizdev. We’re going to a resort in Mexico at the end of April for three days.”

“I see. That certainly sounds good, but tell me everything now.”

“Well, I don’t know much yet, but...”

It’s been long enough since I was picked that I just want this to be over now. What clothes should we wear, or buy if we don’t have the right ones? What activity did we want to sign up for? How many pairs of shoes to bring for basically going to the beach, but there is a gala event. What does that entail? So many decisions, I let my wife worry about most of them. I don’t care what I wear and have found it easier to just let her pick my outfits. It’s all so exhausting and not what I like focusing on at all.

We’re finally here. We had to leave early in the morning to get here before the welcome reception on the beach. Even as I saw the number of people drinking heavily, I kept going back to something my wife had said on the plane this morning.

“Ken, I know this is important for your work, so I’ll play the dutiful wife. You’ve earned this, so enjoy it. You just tell me what you need me to do and who to be nice to.”

Kathy has always supported me in my career, including changing to this new company. But she’s never really enjoyed the holiday party and forced mingling. I think she’s worried this will be more of that. I am too for that matter.

I started introducing her to people I knew and then we were introduced to an employee I didn’t know and his wife. Tom was an enterprise account executive, but we had never worked together for some reason. Like most sales people, he could be both overbearing and a pretty likable person at the same time, and could turn on the charm if he wanted to. He was a lot bigger than I am, and his handshake tried to crush my hand, which I didn’t appreciate very much. He then started focusing on Kathy, asking a lot of questions and telling some stories in turn. I turned to his wife, Laurie, who was almost my height and almost as pretty as Kathy. Out of the gate, she was asking how long we had been married and it only got more personal from there. I kept glancing over at Kathy who was the smallest of the four of us, but she was holding her own against Tom.

“So Ken, why don’t you two have any children? Have you been trying?”

“Laurie, that’s a pretty personal question which I’m not going to answer.”

“Ok, sorry, I’ll switch topics to something more fun. Is this your first club?”

“Yes, it is. I had no idea it was even possible, but I’m excited and honored to be here.”

“Have you heard about some of the things that go on at Club?”

“Besides the heavy drinking and organized parties, I haven’t heard anything. Why, what are you suggesting?”

“Well, Tom and I have been coming to Club for years. After a while, it’s just another beach at a pricey hotel. We’ve left the kids at home, there’s no real work allowed and we’re in a different country. Rules were made to be broken in situations like this.”

“I see, well, we’re a pretty quiet couple, not very interested breaking any rules, especially since we’re only included as a token.”

“Awww, have some fun while you’re here, I know we will!”

I caught Kathy’s eye and indicated it was time to go meet other people. We told Tom and Laurie that we’d see them later.

As we walked away, I carefully put my arm around Kathy and she snuggled into me. “They are a very strange couple.”

“What did you and Laurie discuss while Tom was hounding me.”

“She was suggesting an orgy I think, right after saying that rules were made to be broken. It was a bit odd.”

“Tom was probing as well, asking how open our marriage was. I played dumb and made him explain what he meant which embarrassed him. I had no idea people at your company could be like this. Why haven’t you said anything before this?

“I don’t know Tom at all and normally nothing like this normally happens at work. This is something different. Hey, I see Rob, I’d like you to meet him since I work with him every day. Let’s wander that way.”

Tom and Laurie cornered us in the pool the next morning by sitting right next to us. Tom was talking with Kathy while Laurie sunbathed next to him. I just kept reading my book while the drinks kept flowing.

At some point the two ladies headed off to the bathrooms, leaving Tom and I alone. We talked mostly about work topics until Tom moved to the chair next to mine. If I felt buzzed, I can’t imagine how drunk Tom was at this point.

“Laurie and I really like the two of you. We’e always excited to make new friends.”

“Us too, this has been a fun trip so far.”

Tom caught the eye of the waiter and ordered another round of four strong margaritas before turning back to me. “Listen Ken, I’m getting the feeling from the two of you that you are a pretty quiet couple, but also that you could be interested in broadening your horizons. Especially on vacations like this.”

“I guess, this is definitely not how we usually travel.”

“This might be too bold, but Laurie is interested in you, and I’m interested in Kathy. We’d like to see what fun the four of us could get into together.”

I wondered if he was really going to push and I now had my answer. After a few seconds thought, “I’m not sure. I’d have to see what Kathy said of course. Your wife is a lovely woman, but she’s not worth my marriage.”

Tom’s face brightened when I didn’t reject it out of hand. “Of course, that’s what Laurie is discussing with Kathy right now.” He leaned towards me, reminding me of how much bigger he is than I am, let alone Kathy.

The thought of Kathy underneath him felt like a punch to the stomach, but imagining Laurie on all fours with my cock in her from behind was equally exciting. “This is very strange, hard to imagine really.”

“Just play it cool and I think you’ll be in for the ride of your life.”

“We’ll see.”

The two ladies returned but other than an raised eyebrow from Kathy, neither one looked like anything untoward had happened.

The margarita’s showed up and the afternoon continued. Lots of other co-workers wandered by, but Tom and Laurie stuck next to us the whole time.

As the door closed behind us, Kathy turned to me and asked, “Did Tom proposition you like Laurie did to me?”

“Yes dear, he thought we might have some fun switching partners. I told him I would need to talk with you.”

“Laurie had a hard time getting it out, she kept alluding to having fun, but couldn’t quite say it out loud. Eventually I had to just ask her to spit it out. She was blushing like crazy. I told her I had to talk with you. Honestly, she’s not the smartest cookie, I’m pretty sure it’s Tom’s idea, not hers.”

“I see.”

“Look, these are your co-workers and you have to show up for work next week, not me. Plus, I did say I’d do whatever you needed me to here, so tell me, what do you think of their proposal?”

“Honestly, it terrifies me a bit. I don’t like that he’s leaning on me to do this. I don’t like that he has the ability to make my life more difficult. I don’t like that he might hurt you in some way. Laurie’s pretty, but nothing like you. I guess it all makes me uncomfortable.”

Kathy stared at me for a bit before suddenly smiling. “Honey, I think this is going to work out great. If Tom or Laurie ask you, just say that we’ve decided. It’s Yes. If they don’t bring it up, no harm done.”

The party tonight was in their lazy river which started at a bar with waiters in the water. The pool wound through a little forest, everything was shaded and private.

Kathy had a single pool noodle holding her up while I was in a round tube. We were slowly drifting around, enjoying our drinks and chatting with everyone.

I sensed Tom right before he lassoed Kathy with a pool noodle and pulled her towards him. Laurie latched onto my tube and pulled herself in front of me. She carefully placed her breasts on the tube and then looked up at me with a big smile. “Here you guys are, we’ve been looking for you.” I felt her feet gently find mine and rest on top.

We were still drifting along when I realized that Tom had stopped Kathy and they were falling behind us. I looked over my shoulder, but Laurie put one hand on my face and carefully aimed it back at her. I could see her nipples hardening in front of me through her skimpy bikini top.

“Ken, it’s ok, let them talk for a bit. Tom asked me to keep you company for a few minutes. Can’t we just enjoy this going around the circle together?”

“Sure, you are lovely company, but I don’t want anyone to get the wrong idea.”

“Ken, look around. I’d say half the people here are not standing next to their spouse. The other half are, but even then, see how they are pairing up into foursomes? Some of these people have been coming to club for a long time. They know exactly who they like and want to spend time with. There’s also a bunch of first timers like yourself and Kathy. Keep watching, I think you’ll be surprised by what you might notice.”