It seemed like a great idea at the time, but don't most cluster fucks start out as strokes of genius? Cindy's older sister, Chloe, had asked us if we would be interested in being chaperones on her daughter's class trip to the exotic Caribbean Island of Kokomo. All we had to pay for were our airline tickets. My wife quickly accepted the offer.
Chloe even offered to watch our two kids, who were nine and seven, while we were on the trip. Chloe's husband, Will, was an up and coming lawyer in the middle of a big case. He simply could not take the time off for this trip.
"I've heard some horror stories about kids, especially girls, on these trips to the islands. If I can't be there to keep an eye on Trish, then I want you and Dave to be there," revealed Chloe. "Make no mistake, Cindy. You and Dave have my permission to take whatever steps you feel are necessary to keep Trish out of harm's way. If you feel you have to tan her butt to keep her from getting into trouble or danger, go ahead and do it. I'd rather have her come home with a bruised ego, and ass, than have her disappear, or worse, on this trip!"
"Trish has never given us any problem, Chloe. She's our god-daughter and we love her like our own. Rest assured that we will take good care of her. I really doubt that she'll cause any trouble," responded Cindy.
"Cindy, we both remember our class trips," reminded Chloe. "We were lucky that we didn't get into some real trouble. I heard how you split that bottle of bourbon with two other girls and all three of you were sick the next day. I was caught trying to sneak out my bedroom window, and we were staying on the third floor! I was lucky that we had good chaperones. There will be 75 kids on this trip and 15 adults to keep an eye on them. You'll have your hands full!"
"Dave will have his eyes full with all those young women running around on the beach in skimpy swim suits," laughed Cindy. "I'll be spending more time keeping him in check than the kids."
"Thanks, Sis. I appreciate you doing this for me, and for Trish. She thinks that now that she's 18, she can do whatever she wants, so be warned," advised Chloe. "She's still in our house, we're paying for her college, and she will toe the line."
I was thinking exactly as Cindy had suggested. I was going to spend a week on a subtropical island with 75 kids just graduating from high school. I had to believe that at least 35 or so would be female and most of them would look pretty good in little bikinis. Cindy could worry about the discipline. I was going to relax and enjoy myself. I'd be keeping an eye on the kids alright, the female kids!
We took two rickety old buses from the small airport to our hotel rooms, which were right on the beach. I had spent the plane trip trying to remember the names of the kids, as well as the chaperones. I soon realized I would never remember them all, so I eliminated all the unimportant names. That was pretty much all the males. That made it a lot easier, but I still was having trouble, so I eliminated some of the older female chaperones.
Cindy and I were the youngest chaperones, except for a couple of teachers. All the parents that went were at least in their late thirties. Most were in their forties and a few in their fifties. Miss Marie Beauvais and Mrs. Joan Davis were the two teachers whose names I committed to memory. I salivated thinking about them in tiny little swim suits. If I were any judge of the female form, they would fill their suits out very nicely!
It was still early afternoon, so everyone was eager to change and get out to the beach. That was when I had my first surprise. Cindy came out of our bathroom wearing the smallest bikini I had ever seen! Shit! Now I had to keep an eye on her and make sure all the teenage boys with raging hormones didn't get too frisky. Then there were the other male chaperones. How the hell was I supposed to chaperone my wife around adults? Things suddenly became complicated.
Cindy was a beautiful woman of 34, who could pass for a twenty-something. The only apparent effect the two kids she delivered seemed to have on her had been to enlarge her breasts a cup size. Now they were trying to spill out of her top.
"You like my suit, Dave? I knew you'd be making a fool out of yourself ogling all these beautiful girls on this trip. I thought I'd try to do something to help take your mind off them. The only thing I could come up with was to try to get you to ogle these girls," teased Cindy as she cupped her breasts in her hands.
The first few days went pretty well, all things considered. I couldn't range too far from Cindy when we were on the beach. If I left to get a drink or a towel, I'd return to find several of the high school boys had found some reason to chat with Cindy. They always had at least one of the male chaperones with them, too. I always tried to take it in stride and smile as the crowd dispersed upon my return. They always seemed to remember someplace else they had to be when I came on the scene.
"What's that smell?" I asked Cindy when I returned to her side after an unusually large group of horny young males had been visiting with her.
"I don't smell anything, except the ocean, Dave," replied Cindy.
"I think it might be testosterone, hanging like a cloud around here, Cindy," I told her with a straight face. "It's either that or acne medicine. I can't really tell for sure."
"Dave!" laughed Cindy. "Those young men are always very polite, even if they do seem to get bulges in their trunks all the time. I'm glad they don't wear those Speedos that show everything. It's nice to be appreciated by young, virile men."
"What the hell am I?" I demanded in mock anger. "Most people don't consider 38 as being over the hill. I still get a bulge in my swim suit!"
"I noticed that when I saw you talking to that Dakota and her friend, Grace," observed Cindy. "You need to be a little careful, Dave. Those girls are looking for some fun here and you look like the alpha male in this group. Don't lead those girls on, and don't ever find yourself alone with one of them. You are here to protect them. Be sure to keep it that way."
I blushed a little at Cindy's comment. Those two girls were absolute knock-outs and they did seem to enjoy being in my company. As I considered my fantasies with those girls, I thought about Chloe, and the other parents, expecting me to do my best to keep them from harm. I already had the hottest woman on the island. I knew that. I had to make sure I kept my head out of my ass and appreciated my situation. It was okay to look, but Cindy was my woman and still my best fantasy.
Some of the kids wanted to play tennis, so Cindy, who happened to be an excellent player, and a few other chaperones went with them to the courts. It had been explained to all the kids that none of them were allowed to go anyplace by themselves. Half an hour later, I was approached by Trish and her two friends, Dakota and Grace.
"Uncle Dave? Dakota, Grace, and I are going to stroll up the beach a mile or two," stated Trish matter-of-factly. "We're following the rules by checking in with a chaperone before we go."
"I don't know if that's a good idea, Trish. I kind of feel responsible and I don't like the idea of you getting that far out of my sight," I admitted.
"Then you should come with us, Dave," suggested Dakota. "We can't be any safer than when we are with such a big, strong man. You can keep us in your sight all the time."
Trish gave Dakota an annoyed look. That was enough to make up my mind. If Trish didn't want me to go along, it was probably best if I did.
"Okay, girls," I relented. "Lead the way."
We chatted about all kinds of things as we walked. I realized I was having a good time. Having three beautiful 18 year old girls with me had a lot to do with my contentment. We were almost two miles up the beach when I saw a sign near the dunes. As we approached it, I noted that it was written in several languages. Luckily, English was among them.
"Wait, girls," I cautioned. "This is a nude beach! We'd better turn around and go back."
As I finished reading the sign and turned to face the girls, I found that Dakota was totally naked and Grace was topless and sliding her bottoms down. Both girls looked absolutely incredible! I had to admit it. I also had the presence of mind to know that I had been set up. They had known where they were going. That was obvious.
"Girls, please put your suits back on and we'll go back. You should have asked a female chaperone to come with you if you had this in mind," I complained weakly.
"Oh, Dave! Do we look so terrible?" laughed Dakota. "Should we be ashamed to be naked on the beach? Do the other girls here look better?"
I looked ahead and saw numerous naked women and men walking, chatting, and just sunning themselves. What sort of mess had I gotten into?
"You girls look fantastic and you know it, but this is not right!" I admonished. "I can't go naked and I won't be able to watch you if you go up that beach. I want you to get dressed and we'll go back right now."
"Keep an eye on our suits, if not our bodies, Dave," grinned Grace as the two of them took off up the beach.
I turned to face Trish. At least she had the sense to be embarrassed. Her face was red, and she still had her suit on.
"I'm so sorry, Uncle Dave. I should have told you what we were planning. I couldn't believe it when they invited you to come along with us. They had to know I'd never get naked in front of my own uncle," whined Trish.
I picked up the fragments of fabric the girls had been wearing and took Trish by the hand.
.... There is more of this story ...