Fantasy Sex Cruise 01

This story is about a journey and like all journeys it is best if you begin from the beginning.

Sometimes you think you know where you are going when you set out on a journey but then you may discover that you have arrived at a destination that is not what you expected. But such is the nature of journeys.

There are numerous references to songs in this story. It would be helpful to more fully understand the situation that is being described if you could go to a music site and play the song and then read the passage again while you listened.

Sunday morning breakfast was usually a quiet time for my wife and me. An extra hour of sleep, some freshly ground coffee in the French press and a muffin or an omelet instead of a bowl of cereal made it a little more special. That's why I was surprised when my wife looked across the table at me and asked "Ed, what is your best sexual fantasy? And don't say you don't know or you don't have one because everybody has at least one and they are very clear about what it is."

"Well..." I hesitated and finally admitted that I had always wanted to have sex with an Asian woman. "Of course I've also wondered what it would be like to be with two women at the same time. Is there a point to this question or are you just curious?"

"There is a point" she replied. "I don't want you to take this the wrong way but you must realize that our sex life has cooled since we first met. I'm not complaining mind you but we're like comfortable chairs that we've gotten used to and I've been thinking that we're both turning 50 this year and I wouldn't want you to feel like you had missed out on something exciting that you want to do while you're still young enough to enjoy it."

"Since you brought this up, do you have some ideas about reinvigorating our sex life?"

"Actually, I do. It's not exactly a well thought out plan yet but I've considered a few things and done some research on the Internet and there are some possibilities that I would like to talk to you about."

"OK, I'm always ready to listen to suggestions. In this case, I'm rather intrigued to hear what you have to propose."

"I explored the usual things, porn movies, toys, swingers clubs, going to a sex club in Las Vegas and while I haven't completely ruled out making some of those activities part of our life, I felt like there should be something more appealing and less intimidating to jump start this experiment. But first I had to be sure you were OK with this and that you didn't think I was having a middle aged crisis or just going crazy. I still love you every bit as much as I always have and I wouldn't want to do anything to mess up our relationship at this point. I really need you to understand that I think this can be a lot of fun for both of us. It scares me a little bit to think of turning 50. That's the time when so many marriages get into trouble and somebody ends up having an affair or runs off to 'find themselves' and I don't want that to happen to us."

"Even though I'm surprised by this, I do get what you're saying and I'm willing to try something as long as we're both comfortable with it and it doesn't wreck our marriage. I love you very much and I appreciate the risk you've taken to even bring this up. Now, what else have you considered?"

"When mother died last year she had a life insurance policy worth half a million dollars with me and my sister Marsha as beneficiaries. My half of the money has just been sitting in CDs at the bank and some of them are due to mature soon. What do you think about going on a really nice cruise?"

"You mean they have some sort of sex cruises for swingers or singles that have orgies instead of shuffleboard for entertainment?"

"Well actually they do have those but I don't think that's the best way to begin. I was thinking we could each find somebody that could fulfill our fantasy and spend a week indulging it while we visit places we've never been before. In and out of bed."

"I'm not sure exactly how that would work. Are you talking about us staying in one cabin and having our fantasy partners down the hall so we could just trot off to them whenever we wanted to?"

"No. I think that would inhibit us. That could get the jealousy thing going if things didn't work out for one of us the way we expected. It would also be unfair to our partners to make them feel like they were just sex toys that we could switch on an off as we felt like it. I think it would be best if we each go on our own cruise. That way we could be totally selfish and do only what we want without worrying about what the other one was feeling."

"OK, I agree that would be a more prudent approach. Have you given any thought to where you want to go and more importantly, how you're going to find these people to be our fantasy partners?"

"I have. There are web sites where young men and women advertise their availability for unorthodox arrangements in order to finance their college educations. I've looked at some of these sites and I'm sure we could find some willing participants that would jump at the chance to take a nice cruise and pick up some extra tuition money in exchange for doing what they'd be doing anyway with somebody else. This way it wouldn't seem like just hiring a prostitute; we'd be contributing to someone's education."

"Well that does sound like a more genteel way to proceed. Do you really think we could find somebody that was nice but could also be a fantasy lover?"

"Ed, the internet is a wonderland of possibilities. We could post an advertisement and see what kind of response we get. We would of course have anybody who responds thoroughly checked out before proceeding with an interview and committing to accepting them. Jerry across the street is a lieutenant on the police force. I'm sure he would check somebody out for us if we tell him we're thinking about hiring somebody to work for us as an assistant."

We headed off to my office and Linda showed me some of the web sites she had seen. One of them had pictures and bios of very nice looking young people most of whom were looking for a long term 'room and board' type of situation with the implication that sexual activities would be included. I figured some of them might be amendable to a short term arrangement if the incentive was enticing enough. We each sent emails to about a half dozen prospects and then posted our own advertisements with carefully worded descriptions of what we were looking for.

We discussed the details of the cruise and what we were willing to spend on each of our companions. It was decided that the cruises should be from the same port and should depart and return on the same days. This way we could travel together to get there and return home. Besides paying for our partners' travel, we agreed on a base of $300 per day with the possibility of a bonus if warranted. This would give our companions over $2,000 to further their educational pursuits. As I thought about what we were doing through the rest of the day I have to admit I was becoming more enthusiastic about the idea. That night I was noticeably more turned on than I had been in some time and Linda and I had a hot sex session before we went to sleep.

"It looks like you're responding to my suggestion already Ed." She said as she turned out the light. She was right. I dreamed a very sexual dream and woke up in the morning with a hard-on.

I slid over and put my arms around her. I pressed my cock into her ass crack and kissed the back of her neck. I lifted her leg up with my left hand and slipped my cock between her legs and began playing with her clit with my fingers. I could feel her slit begin to get wet and it wasn't long until I pulled her ass cheek up enough to insert the tip of my hard cock into her moist opening. With each movement my cock slid deeper into her pussy. When I was able to stroke in and out to my full length, I fondled her tit and gently pinched her nipple. She began to moan softly as the tempo of my strokes increased. I pushed her over onto her stomach and lay completely on her back and began to fuck her vigorously. After a couple of minutes I felt my balls begin to churn and then released several strong bursts of hot cum into her as she pushed back against me and squeezed my cock to milk out every drop.

"Ummmh, that was fantastic. You really are starting to get into the spirit of things."

"I still enjoy making love with you even without fantasies." I replied.

We showered and had breakfast and then went to the computer to see if anybody had sent a reply to our contacts and ads. I didn't expect anybody to have responded in just one day so I was shocked to see over 20 emails in my in-box. There was an equal number in Linda's. We spent the next hour reading through the replies and eliminated most for various reasons and each of us ended up with 3 that we wanted to follow up on. We decided to send an email to our picks informing them that we were considering them for the next step and would be in touch by the next Friday with further details.

"I guess we'd better go see what cruises are available. It looks like this is really going to happen."

We began searching for cruises and decided on Ft. Lauderdale as our port since it seemed to have the most options. We found the perfect itineraries. Seven days with one going to the western Caribbean and one going to the eastern Caribbean. That way we would not be going to the same places. We picked a date toward the end of January since that would give us plenty of time to get everything together and would be a great time of the year to go since it would get us out of the cold weather where we live. We booked grand suites with balconies because they both included concierge service that provided a lot of extra amenities. I told Linda she could pick the one she wanted and I would take the other one. They were on different cruise lines so we could exchange opinions about them when we got back.

During the next week we received close to a hundred responses and by Thursday night we had narrowed our selections down to 10 each. We sent emails to the ones selected which detailed the next step in the process. They were advised of the time of the cruise, the requirements to sail such as having a valid passport and suitable evening attire including a formal gown or tuxedo. They were asked to respond quickly so that we could pick the 3 finalists that would then meet with us for an in person interview. By Friday night, 8 of the men and 6 of the women had informed us they wanted to be interviewed and were excited about the prospect of going.

Because most of the candidates lived in places that were not close by we decided to conduct the initial interviews using Skype. This would be fair to everyone and not interrupt schedules due to traveling here to see us in person. If the selections got down to just two, we could do in-person interviews if necessary. We agreed that we both would be present for each interview but whoever was not doing the choosing would be a silent observer in order to give a second opinion.

We made a list of questions that we would ask everyone and give each person a score on them. We would end with asking each candidate why they thought they would be the ideal person to fulfill our sexual fantasy. Linda added a question for the women I hadn't thought about: Will you be having your period on any day during the cruise? I added two additional requirements for my partner: no tattoos and no pubic hair. Finally, each person would be allowed to ask us questions.

It took about 4 days to conduct all of the interviews. They all went quite well and each person seemed very suitable to the task. It was actually pretty difficult for each of us to pick a winner. Linda was more definite about her choice than I was. His name was Bradley Stevens and he was a second year law student at a well-known law school and didn't have much time for a steady girl friend so a week of sex on the high seas was something he could really use. He was nice looking, in great physical shape and was sexually well endowed.

When he stood up and dropped his pants to show Linda his penis as an answer to one of her questions, I could hear the quick intake of her breath and knew she liked what she saw. He was also black. This might have surprised me since we hadn't really discussed what her sexual fantasy was for this cruise but it was apparent that she wanted somebody completely different for this experience. From the look of him, I'd say she was definitely going to get it.

I was a little more indecisive regarding my choice. I was trying to make up my mind between two delightful young ladies. One was from California but her parents were from Vietnam. She was graduating from a university in June with a business degree and wanted to get an MBA but was having trouble finding the financing. Her parents were just about tapped out from paying for her schooling up to now and she didn't want to have to stop and get a job now to save money for later. In the looks department she was everything I could have hoped for. Pretty, exotic, poised, sexually uninhibited but still somewhat reserved in her demeanor.

The other woman lived in Miami. A big plus since it wouldn't cost anything to get her to Ft. Lauderdale for the cruise. Her name was Kealani and she had been born and raised in Hawaii. Her father was a native Hawaiian and her mother was Japanese. She was discovered by a photographer on the beach in Oahu and had been a professional model since she was 18. She was now 27 and had managed to get a college degree by taking courses in several schools between modeling jobs. She knew she wanted to do something once her modeling career was over so she had decided to become a physical therapist and was making plans to attend the University of Miami next year. She too needed help financially to pay for tuition. Beautiful, tall (5' 8), exotic, sophisticated, perfect figure, she said she loved having sex and liked girls almost as much as she liked men. Her answer to the question about why she thought she would be my ideal fantasy girl was 'I've spent my entire adult life being a fantasy for men.'

Linda helped me make up my mind when she told me that if I didn't choose Kealani, she would. I really believed she meant it. I briefly thought about making this a threesome but decided that could wait for another time. To each his or her own on this trip.

We sent emails to everyone thanking them for their participation and telling them we would keep them in mind in case we decided to do this again sometime. We told Brad and Kealani they had been chosen and both were excited. We asked them to send us copies of their passports and to sign a letter of consent to have a background check run. If everything checked out, the tickets would be purchased and confirmed. They would be kept informed of plans as we got nearer to departure.

I was very relieved to have this part of the process finished. Now we could really begin to enjoy looking forward to the cruise. We had less than two months until we left. We kept in almost daily contact with our companions by email and text to coordinate things as we got closer to departure.

The big day finally arrived for us to head for Florida. Because of the amount of clothes we planned to take and the fact that we could make it to Ft. Lauderdale in about 12 hours, we decided to drive the car rather than flying to the port. We planned on arriving a day early so we could be rested from the trip down. We got there about six PM and checked into the hotel. We had a leisurely dinner and went back to the room to go over all the last minute details for the next morning. We called our companions and confirmed that everything was on schedule for meeting up the next morning.

We slept late, had a nice breakfast then checked out of our room and made arrangements for parking the car for the week and taking the shuttle to the terminals so we could be dropped off at our respective check-in kiosk for the luggage. This is where we would meet up with our companions. We had our cell phones and kept in touch with our partners to let them know how things were proceeding. Linda's terminal came up first and I kissed her goodbye and told her I loved her. She hugged me and told me to have fun then walked down the steps of the shuttle.

The ships didn't actually leave until 5 PM but you had to be on board by 3. Kealani told me she had already contacted the concierge desk and that since we had a suite we could check in at noon, which she insisted that we do. She said this was a very big ship and there were a lot of things to do and explore so we needed as much time as possible on board before departure.

As the shuttle pulled up to the curb at baggage check-in my pulse was racing and my hands were sweaty. I was really excited by the prospect of what was about to happen. After I tipped the shuttle driver for getting my luggage off the bus I turned around to see if I could find Kealani. That wasn't hard to do. She was 30 feet away walking toward me like you would expect a model to walk. She had a baggage handler in tow with a cart for my bags. She was an absolute vision. White tailored slacks, cork soled sandals with cloth straps that had gold thread woven into pastel flowers with just enough of a heel to be sexy but still easy to walk in. She wore a silk chiffon blouse in a coral color that had the top two buttons undone exposing exactly the right amount of her ample jiggling breasts. A broad brimmed hat with a floral band topped the ensemble. Expensive amber colored sunglasses and a flawless make-up job completed the look.

"Hello Eddy, are you ready for the best week of your life?" I was still looking at her like I had never seen a woman before. "Before you answer let me answer one of the questions you asked me during the interview." Before I could even think of what she was referring to, she put her arms around me and kissed me. It felt like a jolt of electricity went through my entire body. The way she felt, the way she tasted, the incredible fragrance of her perfume, the sensation of her breasts pressing against me combined to literally take my breath away. I was stunned.

"Well, am I a good kisser?"

I could barely remember that I had asked her that question during the Skype session. "Amazing "was all I could say.

"Now if you'll just give Carl here a couple of twenties, he'll see to all our luggage and we can go check in."

I fumbled with my wallet until I could find my cash and gave the baggage handler two twenty-dollar bills and pointed out the three cases that were mine. Kealani put her arm through the bend in my elbow and somehow got me walking toward the terminal. I was still half dazed by that kiss but we managed to get inside the terminal and headed toward a queue for check in. There were separate lines for guests with suites and we made our way up to the agent behind one of the counters. My mind started working again and after a few minutes we had completed the check-in procedure and were told to go up the escalator on the right side of the terminal.

Almost immediately I sensed something about Kealani. She made me feel like I was the most important person in the world. The way she looked at me, the way she held my arm, her smile and the way she spoke all combined into an attentiveness that I could not remember anybody else ever showing me. I realized that I needed to make a concerted effort to be more like that with Linda. Familiarity may not always breed contempt, but it can induce a mild indifference and lull you into taking somebody for granted. I just hoped I could put someone else at ease as naturally and gracefully as Kealani. It was the first of many lessons I would learn from this enchanting woman.

As soon as we got to the top of the escalator there was a hallway leading to the gangway. About halfway down the hallway there was a place set up to take our picture with the name of the ship in the background and some plants on either side of where we stood. I started to walk by the booth but Kealani gently pulled me over and said "Don't even think about skipping this Eddy, we're going to document this cruise as completely as one of my modeling shoots. So get used to it." I thought the guy taking the pictures would keep her there for the rest of the day. He must have taken 10 shots.