Travel Companions Cayman Isles

My name is Penny, but please call me by my Travel name, Seine.

My mission in life is to see the world, even if I have to fuck a lot of rich men for the privilege.

My trip to L.A. kept me humming through the first week of dealing with my software clients that haven't got a clue. They needed help with the simple movement of files on their personal computers, and I was there to teach them the intricacies of a data collection and correlation program. Perhaps they will be functional one day, but it wasn't going to come as fast as their superiors were hoping for.

When the email showed up about going to the Cayman Islands I almost quit on the spot, but there was that voice in my head saying, "don't jump too soon!"

I booked the extra day that I would need, and when they balked, as I knew they would, I told them that I needed the day as a mental health day, so give it, don't give it, but I won't be here.

It is so much easier to negotiate when you have ten thousand dollars in your freezer, and a month's salary in your savings account.

The Cayman's is now part of the international bank reporting system, but they have no income tax, and they accept cash! My little sister was my new financial consultant, and she agreed that I could move the money, but I should wrap it carefully, since it probably had enough cocaine on it to trigger the drug dogs. She even wired me 5k to open an account for her after she confirmed with one of the Island's banks that it could be done by proxy.

I met Charles Higgins in the Cayman terminal, right after I landed. He was still wheeling his own bag, but he took my heavy carry-on too.

"Yikes! Are you carrying money?" He surprised me with his bold question, but this place is well known as a tax haven.

"Just a few stacks that I didn't need my Uncle to know about," I admitted.

"Here, let me wheel it," I offered to my new client.

"I like it to look like we are a couple, and I would never let my girlfriend carry anything, especially when she is drop dead gorgeous like you!" he explained, and turned towards the pickup area.

"We should have a tour guide picking us up," he announced while craning his neck to see if he could find our transport. He was a tall, but light skinned man, perhaps 38? He had a heavy beard and a bit of a gut starting, but otherwise I felt pretty lucky.

A tall older black man walked boldly up to us, wearing a Yankees ball cap and a broad smile showing white teeth that contrasted severely with his complexion.

"Mr. Higgins, I presume, I am Sigmund Winfree," he told us, looking first to his employer and then to me. "Who would this gorgeous creature be?"

He impressed me with his astute judgment and his delightful Victorian English accent.

"This is my very good friend Seine. Seine, meet Siggy, our tour guide here on the island."

I smiled at Sigmund, but he hadn't released my hand yet, so I thought that I had better say something.

"We have banking to do first, Siggy. Can we hit the financial district first?" I asked our native guide.

He took one of the bags and started wheeling towards a parking lot.

"If I had a woman like that, and I was twenty years younger, I would not need a guide," he announced over his shoulder. "Especially when you're only here for two nights!"

He had a point there, but it was up to Mr. Higgins to spend his money and time as he sees fit.

We were soon on the way, and I got to snuggle up to my new patron.

"So you have banking too?" I asked.

"Yeah, I got a little something extra in my Christmas stocking, so I thought that a quick trip, with a lovely lady, was in order," he responded.

"Your needs are aligned with mine perfectly," I intoned.

"Well, I'm sure that you will satisfy my needs too, so it's my pleasure to help you out, Seine," he added.

The banking was easy, with the introductions that Kerry had prepared for me. They handed me a receipt for my money and a separate one for my sister.

Chuck was waiting for me when I came from the Vice President's office.

"I already have an account, so it was faster for me," he said.

He took my hand and turned to the exit, but I pulled him back.

"I didn't get my hello kiss yet, and it is very important to me," I admitted, then tilted my head and tried to make my lips look very kissable.

He moved in tight, pulling me into his bear-like arms, and gently kissed me, holding it, but not invading my mouth. His hands did not wander.

"Siggy says that our hotel is only ten minutes away, so I thought that maybe you would like a nap before we headed out on our first tourist excursion? Is that okay?" he looked into my eyes with what I thought was a fragile confidence.

"I am not tired, but I would love to spend an hour or two just getting to know you better," I responded honestly. The return smile showed me that his self confidence was restored.

The resort was busy around the registration desk, but Siggy took over by showing us to the bar, then he took our documents and stood in line for us.

"I will text you if my niece can't help me," he claimed with a wink.

Another Islander set me up with a Pena Colada and Charles got a dark beer that they called an Island Pale Ale. I thought that it went well with his lumberjack look.

"So what do I call you Charles?" I doubted that his friends call him by that royal name, but who knows, maybe his dad is Chuck?

"My friends call me Monk, but it's actually a short form of Monkey Fucker, which my mother would not approve of, so they shortened it to Monk, and mother thought it was because I was so introspective and spiritual," he explained.

"That is so perfect," I laughed, accepting his Monkey Fucker name to be just adolescent banter, and not a reflection of some bestiality tendencies.

"My real name is Penny, but you can call me shine, or make up your own nickname for me," I suggested.

"It's only a name, Penny,... Seine" he mused. "In a hundred years no one will care."

The room was ready and they had a golf cart to take us there.

"I will visit with my niece while you two have your little nap," Sigmund reported, handing Monk the extra room entry-card and his paperwork.

When we got to our room, I kicked off my shoes while my new friend took care of the bellhop. I unbuttoned my blouse and let the air conditioning cool my skin.

"Yikes, you looked great before, but... are those for me?" he asked, while undoing the buckle on his belt.

I unclasped my bra in front, and let loose with my girls, pulling the thin, but highly supportive bra from around my shoulders.

"Yeah, they are for you. They are real too, although I've been told that I will have to have them tweaked in a few years when they start to sag," I explained to my admirer.

He undid his shirt, and I could see that the hair continued on his chest, but it thinned out to nothing, well before the belly button. He was well muscled, but he needed more cardio if he was going to trim the waistline.

I pushed the zipper down on my skirt, then let it fall to the floor so he could enjoy my matching garter belt and stockings. I hadn't worn the crotch-less ones, but the panties were lacy and almost see through.

"I offer no apologies for my gut," he offered. "I love to eat, and I try to stay fit, but..." he trailed off.

I moved in fast to comfort him.

"If you didn't have a little muffin top, you wouldn't need me," I offered. "That makes me the lucky one," I whispered in his ear, then nibbled it seductively.

He picked me up like I was a child, and carried me to the bed. His beard tickled my belly.

"Tell me how you like it Monk. On your knees?" I teased.

"Oh, I'm pretty good on my knees," he confessed. "My first wife said so anyway, but she still wouldn't give me any head." He laughed at his own past, so I wanted to satisfy him with my mouth even more.

"How many wives now," I asked as he pulled his pants off, then I helped with his socks.

"Only that one, and we divorced ten years ago," he continued. "I've had a few tries at cohabitation since then, but nothing that stuck for more than a few days."

"You have a way of tenting out your boxers that is so sexy," I murmured, while reaching for the tent pole.

His cock was as big around as my wrist! Thankfully it was only a little longer than normal, I thought as I pulled back the elastic band on top.

"Does little Monk want to come out to play?" I asked his mighty cock.

He nodded his head, so I pulled it free, then pulled the undies to the ground for him to step out of.

He was now more naked than me, but I was sure that he would remedy that in a flash.

I pushed him onto the bed, though I was only half his weight.

"Do you mind if I show you how a good blow job can help you to please me?" I asked, expecting the answer that I always get to that question.

"Oh god, that would be wonderful!" Monk replied with an un-monk-like smile.

I warmed his cock with my hands while I ran my tongue over his ball sack, and sucked each of his testicles into my mouth, but I was watchful that I wouldn't make him blow his load before enjoying my tongue on his shaft.

Finally I pushed it in and gripped him with my lips as I pushed down. He was too big to go anywhere in my throat, but the four inches or so was obviously more than he was used to and my tongue was doing it's normal dance. One hand was lifting his balls while the other helped to keep the extra length pumping in time with my lips.

He lasted about 60 seconds.

"Oh yes, you are a good cock sucker!" he moaned and lifted his hips in an unmistakable pre-orgasmic thrust.

"Yessss," he started to pump, but I wasn't going to stop. I wanted him to remember me when he planned his next trip, and I was thinking St. Bart's or Aruba.

His cock was definitely one of the fattest that I had ever engulfed, even in college, but it worked like any other. I could tell that he hadn't been this excited in a while as he spasmed out stream after stream of jizz.

I cleaned him up then crawled up the bed to lay next to him.

"Wow, I had forgotten how good that could feel," he confessed.

He turned on his side to face me, then idly played with my left nipple while studying my face.

"How do you like it, Seine?" he wondered.

"Cock, fingers, tongue,...I like them all," I whispered.

"Then let me get a good taste before I mess you up," he replied.

"Let's just turn this into a sixty nine so I can energize that sexy cock, while you get your little taste, baby," I insisted, while shimmying into position. He pulled into me using my ass cheeks as handles.

I started to lick him with the honest intention of getting him hard again, but I lost focus when he pushed a wet finger firmly, and completely up my pucker hole.

When I was on the brink he started to slowly ass fuck me with that finger, which distracted me from my reward. His steady strumming of his tongue came back around to focus my attention on my approaching orgasm. When I finally started to cum he pushed his thumb between my labia and he whisked it back and forth extending the sweet spasms of love until I was spent and dazed.

A little life in the cock was all I needed to feel before I started the vigorous licking of the underside. Soon I knew that I could mount him.

"Play with my nipples while I search for life," I joked while reaching for his expanding manhood.

I leaned my chest into his mouth's zone of influence, and he did not disappoint me by being shy.

I found my own wet slit with my eyes shut and fed the hungry wolf to my lusting snatch.

I kept my nipples where he could please us both, pivoting my ass in a 5 inch arc into his groin, smashing my muff with a satisfying slap.

My hours of cardio were paying off, as I kept up a steady beat until he was biting a little too hard on my nibs.

I pulled up and he used his hands to hold my body higher while he slammed into me with twice the velocity of my strokes, making me cry with the start of another fabulous spasm.

He slowed a fraction as he burst into me but I was still absorbed in my own pleasure.

He might have fallen asleep, and many lesser men would have, bringing me with them. This one was made of different stuff.

"Okay, let's go check out a waterfall!" He jumped up and headed for the shower. I quickly joined him there, but we didn't fall into shower sex. I could feel his need to be active, and I instinctively wanted to support him in whatever adventure he was on.

We were soon reconnected with Siggy and we headed out to their tropical backyard for some waterfall fun.

"It is a lengthy walk, but the destination is well worth the effort," our guide encouraged us as we hit the footpath itself.

We had to walk in the river a lot of the time, as the jungle had swallowed the trail. The sun was hot, but we were in the shade much of the time and there was a breeze coming down the valley.

About an hour passed before we could see our destination ahead and it made us move faster. The sound was different too as we were now deep in a valley and the cacophony of the rushing water echoed off of the walls and covered the excited sounds of the birds and monkeys. The air was damp and musty with the smell of wildflowers.

There is no doubt that I was the youngest and fittest in our party, but Siggy moved with grace, and a familiarity that few would possess, while Chuck was sweating like a bull after servicing the herd of cows. He was certainly strong though, and he was chivalrous enough to offer his hand whenever it might be needed. I used his help too, knowing that would make him happy.

Finally we arrived, and it was worth the effort. The solitude made it very special. Sigmund set up a spread of fruit and sandwiches. He used water from the stream to turn a concentrated fruit mash into an exotic drink complete with ice and rum, then he relaxed for a few minutes and had some refreshments himself.

"I will leave you too for some romance," he informed us, but I have to feed my own soul for a few minutes. I am sure you understand."

He leaned back, and let the cool moist air bring his body into a relaxed state, while we explored the area.

A half hour later he was set to go.

"Don't forget to check out the cave behind the water curtain," he finally said, as he gathered the things that he would carry back out.

Now that we were alone we stripped ourselves out of our shorts and shirts, but we maintained our shoes, so we could swim and walk on the rocks without cutting ourselves.

I thought that we would continue our 'playing' in the small pool at the falls, but it was far too cold to stay in for long, let alone expect a fat wanker to stay firm. Instead, we continued on to the spray of cold water and through to the cavern behind. I was much warmer inside and out of the spray.

The cave only went 25 or 30 yards, but it had a slab of rock that looked just like a table. I wondered if people had housed themselves here in ancient times.

We explored for a bit, but the light was weak in the cave, so we decided to sunbathe for a while to warm up.

When we came through the curtain of water and back to the bright light, there was a middle aged couple holding hands, and just stepping into the water. They were wearing swimsuits, which contrasted distinctly with us.

"See Barry, it is okay to go nude!" The woman proclaimed with obvious joy and she reached back to pull the strings on her top, releasing her girls to bounce nicely.

"Look at the size of that guy's Johnston!" Barry proclaimed. "Divert your eyes baby!" He laughingly instructed his wife.

"Oh, I'm sorry we didn't expect anyone," I apologized but didn't bother to cover anything.

"Yowsers!" Monk cried as he covered himself with his hands.

"Hey, Barry, he's shy!" the woman responded. "We better get naked before they feel embarrassed!"

They both had their bottoms down, before we could intervene, but on reflection, I think it was the kindest thing to do.

"My name is Seine and this is Monk," I told our new friends, since they had instantly become my friends.

"He sure doesn't look like a Monk? She responded, licking her lips. "I'm Sharon, but my friends call me Sharky.

"A real man-eater," Barry continued the intro, but his eyes were looking at me, as if they had finished undressing me, and they were continuing with what came naturally. His cock was now loose and growing rapidly.

Monk was still frozen in place, but at least he had dropped his hands so the Shark could have a good look.

Sharon continued into the pool until her saggy tits were uplifted by their buoyancy.

My client had moved out of the spray and his cock was lifting up with every step that Sharky took.

"He looks yummy Seine, do you mind if I touch it? She was kind to ask.

I didn't say a word, but I was wondering what Barry had in mind.

She now started to emerge from the other side, right in front of Chuck, but they had removed their shoes so she had to stay low, due to the sharp rocks. She stayed there, perhaps deciding that she could only enjoy that cock if he brought it closer.

"Do you mind Seine? It could be fun," he asked, flipping the decision back to me.

"Whatever you like hun, but I can't have his cock in me without a condom," I insisted since I have no idea of his sexual history.

"We have some!" Sharon reported with glee. "See Barry. 'Be Prepared' pays off again!"

Chuck took two steps and let the Shark have a close up inspection of his fully engorged monster.

"At my age, we are more worried about sunburn than herpes," she reasoned...But I don't see any, and I don't have any, and we better get that pink cannon covered, Hun!"

She licked the end and under the head, holding it in both hands she moaned in delight.

Barry was watching me from below but not far off.

"Is there anything that you need sucked or licked, Sweety? We are an equal opportunity team," he offered, but stayed there to make me accept or decline based on where I went.

I looked at my date and he nodded, so I took the two steps forward and found myself resting on Barry's face, with my feet spread twice the width of my shoulders.

As I saw Chuck close his eyes and arch his back, I knew that he was enjoying himself, so I cupped my tits, closed my eyes and let myself enjoy the experienced tongue and fingers of the Sharks Mate.

I was the first to cum. The cold water doesn't affect me as much as it would a man. It had engorged my tits though, and now they were sensitive as I pinched the nipples. Barry did not let me go though, and his continued interest and intensity practically forced me to stay in place and watch my client burst onto Sharon's face as she jacked him and licked as much cum as she could get.

The Shark kept her grip on the Monkey Fucker, forcing him to regain his blood supply. She took her wet finger and circled his anus, bringing him back to nearly his full size.

I had only briefly seen Barry's cock as he had it underwater soon after taking off his suit.

I hoped he was a grower, not a show-er, but I have been to College, so of course I have been fucked by some 3 inchers more than once, without regret.

I personally believe that a fat five incher is perfect. It doesn't rub your G spot, it hits it, if you use the right angle of entry. It stretches your labia too, which has a lot to do with how much you lubricate yourself. If he can tap tap tap his way onto my labia, he will make me cum until he stops!

"If she has a condom that will fit me, I'm going to have to return the favor Seine," he stated while looking at me, perhaps for approval.

"If Barry fucks as good as he gives head, you may regret that decision Monk," I complimented my Pussy Licker while giving an okay to the sharing plan that my employer was offering.

Barry turned for shore but took my hand. He wasn't going to get any blood in his boner unless he got out of the water and warmed up. I was happy to add the warmth of my breath and hands while I inspected him for signs of an infection, but he was completely shaven, so it was easy to see that he had nothing obvious. I still pushed a condom down over his fatty while the three inches expanded to five. With his trim waist I was in for a treat.