Bruise Cruise 2 part 1

[ve****]

The sub that had elected to go on the second cruise was named Sally. She had contacted me prior to my leaving back to Florida from my summer home. Sally was someone who I had seen online before and had been attracted to but she had failed to answer my message. She is Generation X and is 55 years old. She lives in a very nice suburb of a major City South of me several hours by car or a short hop on a plane. Looking at her profile you might think she is just another pretty face – perhaps even a chat bot or fake profile. She had just a few pictures but each showed as a slim, good looking woman, modestly dressed and looking nice fo her age. She described herself as an almost empty nester meaning that she likely had a youngest one still living at home if not more than one but that they were almost out the door. She put up front that she wanted a long term relationship but that is common theme across almost all the single women I have viewed profiles of and of course she was looking for love of some kind. On the other hand, she was honest enough to admit that she was into the BDSM/Discipline scene as well as that of some k ind of role plays. She had little experience except for a relationship where she said she had dabbled in the life and had found it satisfying to her, even to the point where she acknowledged it was something she craved. She was looking for someone who is independent and well disciplined and she would welcome that discipline into her life. Generation X members were raised with little direction and often left to figure things out for themselves. Unlike the boomers who were spoiled and coddled and believed themselves as special, they became self reliant, they had to figure out how to navigate the world, and usually have a sarcastic or sardonic view of the world. They grew up with MTV and had to navigate between the digital and analog world as they grew up and reshaped rock and roll in the process. They were known as latch key kids for a reason since many of them came from families where both parents worked when they were lucky enough to have to parent. They would let themselves into their own homes at an early age, took responsibilities for younger siblings and made sure that chores and homework was done. Often they had to actually fix or pick up dinners for their families. They were not given favors nor did they expect them. Even today they have little belief that any safety nets will be in place for them in their old age. While their parents might have talked to them in ways to provide them with a path through life, they probably viewed it skeptically. Instead they learned the hard way, by making mistakes and then correcting them. As a whole they are reliable and viewed as a bridge between the generations. They are do not demand attention but instead view the actions of later generations with some disgust when they viewed the participations trophies, grade inflation and helicopter parenting techniques. They thought even less of the older boomers who they often view as spoiled and overrated. They even feel cheated as power was held back from their generation in politics and other public acclaim. So using some of that information which I have gleaned over the years, I read between the lines of her profile as best I could.

She gave enough information to provide a site user with what she desired but did not expand much beyond that. While she had been a user for a fair amount of time, she had obviously spent much of that researching the site and the lifestyle but not interacting with others. Instead she was on her own hunt not only for interaction but also determining what she wanted. She also had time since she was not of retirement age and still only approaching her empty nester phase. I am sure she had many suitors but se probably let few of them into her life unless she had time to actually get to know them. She was cautious. She had probably learned not to jump into anything without proper research no matter how good it sounded like. She was recently separated which I took to man her husband and she were in the middle of or at the end of a divorce and considering the neighborhood she lived in, she was likely getting some kid of child support if not alimony. She would not jeopardize that until her last child had been taken care of for sure. I assume she had married fairly young and had been for some time because she did not talk about former relationships. She also was vague about her experiences in the lifestyle only referring to a previous relationship where she had dabbled and found it exciting. She was still learning. Still I gave her great credit in putting it out there. She was honest about where she was in her life. Again an assumption, on my part was that
she had never had the chance to really sow her wild oats in the past. She wanted some excitement and adventure and was ready to go after it but only on her terms. She wanted to be confident she was not going to end up on the short end of a stick. Even the name for her profile seemed to be carefully crafted to provide notice of where she was heading. He needed some kind of safety net, some time to adjust, and someone who was willing to take a chance on her and teach her how to have fun. As I said, I had been interested and had actually had hoped several months before that she would contact me but had given up any hope since I may have been too old for her to consider. On the other hand, I never give up hope and filed her profile into my favorites even as I gave up any chase.

When I placed my ad, I was surprised to hear back fro her saying that she might – with the emphasis on might – be interested. Even so, she couched her reply in very vague terms which is something I have learned to be wary of since it is often the prelude to finding out that it is only a scammer or bot looking for easy prey. Even so, I answered her chat message with usually cheery “Hello, what can I do for you to bring a smile to your face or a blush to your cheeks. We bantered back and forth while I tried to figure out if she was just a chat bot, asking her about her neighborhood, her life a little, while she cam back and inquired “What I was interested in?” Since my profile is pretty detailed, that is often another indication that person had either not read my entire profile which can be off putting since it is blunt and plain spoken or that again she could be a fake profile waiting for me to entirely believe her story. There is one other possibility and that she was being very cautious indeed and perhaps just a little bit afraid of what she had read about me. Now I am the first to agree I can be somewhat frightening if you have not met me in person and even then I can come across strong despite my tendency towards tenderness, generosity and kindness. In my own mind I gave her the benefit of the doubts and we continued to have longer and longer chats. Slowly but surely she started to draw 0out from me the details of what I wanted, which as I said previously is a set of travel companions, which I could perhaps ultimately draw down to one, who would like to experience adventure and excitement with me and perhaps have it occur to them it might turn into a long term relationship. There were quite a few long conversations concerning my thoughts on my thoughts that the best way to find out was to take a person on a vacation doing things we might both find enjoyable but also be allowed enough time to explore intimacy. In the end, I also assured her that not only would I be patient, respect her limits, but also that I knew that no means no. I have no desire to overwhelm a person who does not want what I have to offer. I gave hr my word that it was perfectly safe since we would be aboard a place where help was seconds away among the crowd on a cruise ship, that if she decided she did not even like me much, we would just endure a few days together with no sexual activities, and that really the sexual aspects of the trip were not the most important to me at all since I was looking more for companionship in which I could enjoy the environment in. This was all conducted online of course without meeting or even seeing each other online just on chat. That seemed to break the dam and she agreed first to some phone calls and then to a personal meeting. This proved to be something of a problem since I was face with an either or choice. Since she was a few hours away by car I could either choose a trip of a couple of days with the risk that the initial meeting would be a bust, perhaps even a no-show by her, or that I might have to have a second or third meeting for her to decide. On the other hand, I could fly in, rent a car at the airport and show up at the meeting spot and then fly out. I would have to board my pup if I were to be gone overnight. I finally decided to make the drive, book a hotel near her neighborhood, arrange a meeting in a neutral space in the hotel bar where we could get lunch. If it was a flat out bust, I could get get home fairly quickly and get the dog out of the boarding facility which would cost more than the entire trip since I board him in luxurious surroundings (that is true even when I take cruises since his boarding is often almost what I pay for the cruise for me. He is a spoiled mutt, well loved, but spoiled.)

I made the drive and checked into the hotel. We met and we hit it off, albeit slowly. A lot of our conversation at first was telling each other our backgrounds and I was open and honest with her about myself. She was a she presented herself, younger than me and pretty. Athletic and bubbly. We talked about a lot of other things as well and decided I would take her on a real date that evening out for dinner and then drinks. I begged her not to make me dance since I was lousy at it but promised if it went well, she would have a chance to see just how lousy I was. We spent a little time on actually taking the cruise, but I did mention to her that I was taking my female friend on a cruise where no intimacy was going to occur and this was the second time we would be doing it. I described the funny incidents that had occurred on the cruise we had taken together and explained that I knew that relationship was never going to work long term and why. I also explained that if she did not want to be intimate with me on a cruise, I was happy to take her and I could be a gentleman the entire time even though we would share a suite together. Perhaps that helped make her decide. I don't know. I do know we had a good time together even though we did not have relations on that trip. We continued to chat after I got home and at some point, she decided or perhaps was able to carve out some time when she was available to try a cruise with me. Perhaps she had decided if nothing else she would get a free vacation in a warm place during the winter. Again I have no way of knowing what made her make the decision but I was thankful she made it.

Chatting online again, we decided on a set of dates and I set forward to make the plans. I would have to fly her down to meet me the day before the cruise started. I could get flights easily for her since she was fairly near a major city. I let her choose her flights and I sent her a check to repay her for them. This time we chose a little larger ship but still the same line I always use since it gives me the perks and gambling I want. We set the dates in late February. I made sure she was aware that I was dating other women as well since I did not want that fact disturb her in any way. Better get it on the table rather than have some kind of kerfuffle later. As the schedule came together while I made the arrangements I made sure she had good input for everything I planned. I decided it would be safer to expect that she was something of a novice on everything and take it slow.

Much like I had with my previous dates, I laid on lots of extras with massages, a spa day, excursions she might like to do, a drink apckage and the internet as well as some more intimate things like special dinners and other such things.

[Ba****]

Write a book why don’t you?

[Mr****]

Do you not have anyone to talk to?? I mean I believe it if not. One of your memoirs I read would have been enough to get you arrested.

[ve****]

Give me a break. I type fast and it is a hobby. Hope you enjoyed the stories.