Travel Companions Cayman Isles

"Hmm, when was the last time I left you hanging?" He boldly challenged.

We learned a bit more about sex and drugs in the 80's, surprising me with this stately man's past.

"Sigmund Winfree can trace his family back to slavery in Jamaica. His grandfather not only won his freedom, but his entire family was educated in England. Siggy is the only one to return, with his degree in History, he became a teacher, right here in Georgetown," Simone filled us in on the personal history of the Winfree family.

"That is ancient history," Sigmund insisted.

"He fell in love with the beautiful daughter of a Dutch Banker," Simone continued, "It was a great scandal, almost costing Sigmund his job, but they lied and said that Charlotta was pregnant, so they were married, but they had to live outside of town, so their 'unnatural' union would not be seen in the City." Simone finished the romantic tail.

My admiration for both of them doubled on the spot, and tears came to my eyes.

"Ah! You're a romantic, Seine. Are you sure you're in the right career path? She asked, then realized that she had gone a step beyond decorum.

"Oh, Shit. I didn't mean that in a bad way dear," she rushed to apologize for referring to my occupation.

"No. No need to apologize, Char," I held up my hand gesturing for her to stop apologizing. "I want to see the world, and I'm a big slut, and I love shagging a new guy every other week. These guys are always horny, and I am happier where I am right now, than in anything else that I've put my energy into." I explained to the small group, including a few women from the kitchen.

"If I had a chance like that when I was 20, I'd be sitting on a beach in Rio with a Pena Colada in each hand," One of the older women mused.

"You might have to suck a cock after that drink," I informed our audience.

"I like to suck some dick, I do, you bet," she returned. "But he better get his tongue busy for me too, sister, cause it's tit for tat in my bedroom!" She fairly hollered as she let everyone know her preferences in the boudoir. We all laughed and cheered for the truth of her confession.

It wasn't fair to Siggy to stay out any later. When he dropped us at the hotel, Charles told him not to pick us up until after we got back from our snorkel outing around the Eastern Cayman Islands.

It was hard to believe that it was only day two! Our sail boat picked up a dozen people from our resort, and had 6 tourists and 4 crew already. That made 22, and the boat was probably limited to 20! The crew never sat though, doling out heavily loaded drinks of fruit juice and rum, or water, in the case of us hungover customers.

These islands are lightly populated but the villages are permanent, with one room schoolhouses for the youngest kids. Once the young ones are 12 they are transported every day by high speed ferries, to the High School in Georgetown for the furtherance of their studies. There are scholarships for any Islander that has the GPA to go to University. Many move into tourism and return as resort managers and business owners within their own islands.

The birds are the great attraction here, with the red footed booby being the greatest draw. Their reefs are a secondary attraction, but the variety of colorful fish and vegetation may not be as significant as the reefs off of Belize, but it is still a great swim.

Every time Monk helped me put on more sunscreen, I wondered what we were doing out here, but I knew that the sex would be that much better after hours of wanting it.

When we got back to the hotel I sent Siggy a text that we needed a small nap, then maybe he could meet us in the lobby, or hammer on our door to wake us up! He gave me a thumbs up and a smiley face emoji.

We came together in the shower, with Monk holding my jugs from behind and his long thick cock bouncing up between my legs and tapping on my swollen labia. He lathered us both up, partly to rid us of the sticky layers of coconut sunscreen, and partly because it was fun.

Eventually his cock found it's home in my pussy, and he hammered me as I leaned forward, letting the warm water hit my back and splash in his face.

We didn't want to lay in the bed, since it was all made up, but we did fuck on the balcony, while looking out over the bay. We saw the twinkle of a telescope on the balcony across the parking lot, but we didn't care.

"Let them watch and learn," Charles growled in my ear as he propelled me into another delightful orgasm, then he roared as he filled me with his passion, even if it was only a squirt, having delivered twice in the shower.

I caught the tinkle of the house phone when we came back inside, and knew that we were expected in the lobby.

Sigmund and Charlotta were taking us to a resort on the other end of the main island, for a dinner show of Caribbean dancers and singers. They had us participate in some of their skits, making us dance with them and playing games like passing a bottle man to woman using only your knees. Even Siggy and Char joined in the fun.

We ended up back at the Vagabond for drinks and Lemon Meringue pie.

We only had the strength for a quickie when they dropped us off, but it was still sweet.

In the morning we had shower sex, taking the time to make sure that every part was first satisfied, then cleaned and dried.

We packed, and brought everything down to the lobby before we went for breakfast.

"Where are we going next time Penny?" Charles finally asked.

"The real question is when?" I responded. "Any paradise will do for me, Lover."

"Hmm, I can afford just about anywhere in the Carib, if it's only for a weekend," Monk decided. "What about Cuba?" he suggested.

"Never been there, and I am available any weekend after mid March," I let my new friend decide.

Charley handed me an envelope.

"Your tip, but don't open it until you're on the plane," he explained.

"I enjoyed your company tremendously, Charles Higgins," I admitted. "...and I look forward to another time and another place, if you don't feel that a different woman is necessary to make you happy.

"I don't suppose we really know where we are going to be in 6 months, but I loved my time with you, and anyone new would be an unknown," he explained his decision to stay with me, which is why guys stay with girlfriends that they sometimes can't stand.

I decided right there, to gently reject his next invitation, and insist that he sample more of the 'fish in the sea'!

Siggy dropped us both off, though Monk's flight was an hour later than mine. We enjoyed each other's company until I had to board.

The envelope had 10 hundred dollar bills and a note.

"Penny, I know that you are new to the business, so I am going to travel with someone else next time. If you want to see me in a year, then we can meet at the bank exactly one year from our first visit. It's kind of like Cary Grant and Deborah Kerr meeting on the Empire State Building. If you're still in the business, you'll have some cash to make it worth your while. If not, I wish you the best." he signed it Monk.

Well, I guess he was smarter than he looked.

I sent a text to my Travel Agent, from the Uber, letting them know that I am home, with another happy customer. Sid gave me a thumbs up, but nothing about another trip.

Sue, the Condo Manager dropped in when she saw that I was home, and I invited her in for a cocktail. I had some Jamaican cream rum from the Duty Free, and she wanted the highlights from my latest sexcapade.

"He was like a Canadian Lumberjack," I described my latest client. "Full beard, some winter weight around the middle, and a cock like a fat hatchet handle." I was feeling a little horny, just describing him.

"He gave you a tip of a grand?! How did you earn that, sister," she asked with a mischievous look on her face, like it didn't matter what I did, she would have done it for free.

"I just gave him my body, he is only a man, so getting what I want is easy!" I confessed.

Yes, I do love to travel...but the sex is fucking great too!