The Bruise Cruise Part 1

[ve****]

This a part 1 of a Jay D Strapper short story

I thought you might be interested in my story. I am an older man, now retired, single after my wife passed, an empty nester with grown *** who are successful. Through hard work in a successful career and good investing I am well off – not wealthy mind you but well off enough to be able to enjoy the finer things in life. Gambling and traveling are two of my passions among many others. I stay busy.

Sometime back I was introduced to the concept of a hot wife somewhat by accident. I was staying at a Casino/Convention Center outside of Las Vegas which was fairly new, plush and had great perks. I was not part of a convention that was going on, but noted that it was there. I was there to gamble and relax for a weekend get away. That Friday evening, I was taking a break in the bar area having a drink when a stunningly good looking older gal sat next to me and offered to buy me a drink. Who am I to say no? We sat and talked for a while during which she mentioned that she was a wife there on vacation but was a little vague on the vacation part since she did not seem to be with anyone else. In my mind I started to wonder if she was a hooker but two things dampened that thought. She was older than most in that trade and second she had previously said that she was a wife. During our talking, she casually mentioned that she and her husband were in an open relationship and that her husband was elsewhere. That of course piqued my attention. One thing lead to another and we ended up saying with each other for weekend, enjoying each other's company and I had some great guilt free sex as did she. It was great with no strings attached an with no addresses exchanged. Moving a little forward in time I am a little older and sort of lonely as well. I do not discount my getting romantically involved again but time is marching along.

In the fall I shirt to my second home in Florida and begin what I call my cruising season. Since I have nothing but a dog to be responsible for, I am able to adjust my schedule as I wish. I usually take at least 3 and sometimes 4 or 5 cruises until the next spring. The cruises are normally from 7 to 10 days in length primarily due to the boarding the dog. He is older and has anxiety issues and I do not like to board him longer even though I pay for premium care for him. So I am restricted to shorter cruises at this point. Cruises fit my life primarily since it gives me a break from the day to day humdrum and provides me with the opportunity to gamble. I no longer even get off the ship in the ports since I have been to all of them numerous times. Instead I stay aboard, take advantage of the amenities and work out of my suites. I always try to book at the highest end possible so the lodgings are comfortable. Part of that is because I get special comps for gambling and part because I just can afford. Cops always include suite upgrades and all kinds of amenities from free play in gambling to chocolate covered strawberries in the room to champagne upon arrival. I always use the same cruise line which is a high end line and I am good customer which adds to the luxury. I do work during the day writing and doing research and sometimes completing investment I am interested I as well. The rest of the time I use for relaxation and of course gambling. It does get lonely however. I have thought of various ways to remedy that loneliness with some success primarily by bringing my kids along or taking my older grand***. The problem is that they all lead very busy lives with grandkids still below 16 and the parents busy with their own careers which meant scheduling cruises over Christmas breaks or spring breaks. So during the last cruise season I thoughtI should just invite a lady friend I have to go with me. We had keep in touch over the years since she had been my executive assistant for eight years before I retired but had not seen her for several years. So on a whim, I called her and asked if she would like to go. I promised to be a gentleman but we would be sharing a cabin. I had some hopes that since I thought I had detected a chemistry when she worked for me, but that was not meant to be. She had a live in boyfriend and problems all her own which I will not go into detail about. I paid for her flight to Florida and her return as well as the cruise, her drink package, internet access, and excursions for her to go on in ports. We had a great time. I took her out to some specialty dining and showed her the night life aboard and what she could do with her days when I was working. She was the belle of the ball, meeting most of the other guests aboard, partying hard, learning to gamble which I gave her an allowance for, as well as getting massages and Spa days all of which I financed. In return, I got to hang out with a lot of folks I would otherwise not have met. It was a great deal for both of us. She got an all expenses paid vacation and I enjoyed her company despite no sex involved. When we returned to Florida, she gave me some advice to join one or two matching sites and told me that I should look online. I took her up on that.

I learned some lessons from that trip. First, I had all the advantages being older and more mature has. I am experienced and mature in my actions. I have enough disposable income to treat my guest well within reason, and finally I can also indulge my BDSM kink which is being a Dom. The second lesson I learned was that you had to find a connection to other kinky people to find what you are looking for. The sites I researched gave me that in. I researched the sites and picked the three most popular and older kink sites as well as one site for more mature people. After much trial and errors which i will not get into, I settled on one site I use. I fought off the AI chat scammers, the Bots, and the fake profiles, I delved deep into that site and found that the real action is underneath the surface of the site and how to actually talk to women again. Some of those lessons came hard and some were easy but all had to be learned or re-learned in my case. Some are still not learned. In any event, my next brainstorm was to put an ad or status on my profile for those who dig a little deeper. Now I was getting contacts but most of them turned out to be hookers, escorts or scammers.
While I was happy to pay for a vacation, I did not intend to pay for sex. I thought back a while to my stay in Las Vegas and determined that what I was looking for was a sub/slave single woman or a Hot Wife with no strings attached who might like to take an all expense paid vacation. In return, she would provide me the company I desired. Of course this provided problems of it's own to figure out. First was that I wanted to make sure we were compatible which meant some kind of in person meeting with said subject. The second was trying to avoid scammers who would try to take advantage of my largess. The first I solved by making short trips to those who answered and were on my radar. The second is that I used non-refundable tickets for airfare and not attaching my credit card to her account until she would arrive on seen. Because the Suite was already booked, I could buy packages in advance and get returns to my credit card if she canceled at the last minute. While I would sacrifice the air fare, I figured it would be worth the risk. Some risk had to be borne regardless.

I tried to make my overtures discrete but detailed. Her limits would be observed scrupulously. She would have the days off but I expected her to be my companion to dinner, gamble with and ultimately have time together after hours. If she chose, we could spend even more time together but that would be her choice. In return I would set up special packages for her luxury including a Spa day and massages. As we got to know each other online, I would get her measurements and order us some role play costumes for her which she could keep as hers. She could even choose maid, slave, pet, schoolgirl outfits whichI would have delivered to me. I would supply the implements and devices. This was her chance to live out a fantasy at a price of nothing except for perhaps some souvenirs from the ports since she would also get some onboard shopping ***. I thought it was a good deal all the way around. Again I had lessons to learn.

Again I got lots of responses but none panned out. Obviously I was missing something but I had no clue what it was. It ended up being what I would call trust. I had not been vetted long enough for the ladies to feel it was real. A tie went on an I dug deeper into the site, posted more, gained more friends and linkages, I suddenly started to get noticed more and taken seriously. Now I was getting the responses I had first expected. As I chatted with the women, I made sure I was honest and open about my intentions. Regardless of all else, this would start off as a no strings attached relationship which was likely to be fated to end when the return flight started. It didn't have to end that way but most likely it would unless we made a very special connection we wanted to continue. I also made it clear that a longer term relationship might be preferable to me simply since ti would solve my problem of having a traveling companion in the future. As all of that happened, the dam burst. Well anyway, I got some serious responses.

As always I try to be kind outside the bedroom. I always answer my chat requests and I try to be a gentleman in public and would honor that on the cruise as well. In my mind, she would never be anything than a friend I had made online and I was treating to a vacation.

I sorted though the responses and chatted with the women involved carefully vetting them and planing on how I would arrange discrete visits to them so we could meet in person. A lot of time was spent in planning in how details wold be worked out such as transportation to and from, what items she wold need to bring, where we might go on cruise, and those kinds of things. The most important to me however was to meet her and to decide it we would be compatible. That was the final test to start making real plans.

In some ways that was easy as some wee within driving range from my home in Michigan or from my home in Florida. The list winnowed out as I came closer to when the cruising season would start but I had already limited myself a little since I was taking the friend I had previously taken on a cruise in November, limiting my cruising days open but also giving me more time to arrange meetings and cruises as I limited the cruise days available to January through April and perhaps if needed into May although I did have some conflicts in May for other functions I had to attend.

I made the arrangements for the cruise in November while I worked the details for the other cruises. It got complex. Finally I managed to get some finality for three cruises after the first. One in January, One in February, and one in April after meeting with three different women. All of whom were highly satisfactory to me.

[re****]

My greatest bondage tool is trust. Though generally during play is restricted to velcro or belted cuffs, simply because due to my hyper independence I will go into a sort of hyper awareness and possibly panic if it's not something I can get out of on my own. That defeats the purpose for me. There is a rare occasion and it's discuss that I would agree otherwise. Never spontaneously.