Bruise Cruise 2 part 2

[ve****]

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 a package and the internet as well as some more intimate things like special dinners and other such things.

Since we chatted with each other almost every day, I had a chance to more fully get to know the things that drove her. Not only did we share information, but we also payed some little games online that also helped. She new about my cruise in the fall with my friend and I shared some of the things we did on the cruise with her. I also shared with her not the specifics but the at least the preparations of my cruise I was going to take with Linda in January. When I got back from that cruise I would share some things about that cruise with her as well, not the personal things so much as the more impersonal things we did such as our gambling results and that type of things.'

It turned out the games we played on line helped my to figure out a lot more about her. Sine as most of you know, I like to use fantasies as an outlet. So we played fantasy chat games where we would alternate one to another telling a story for example and allowing each of us to to steer the story into areas that we might like. Over time the stories became spicier and spicier. As they did, she steered them more to exhibitionism and *** as an area she was interested in. At some point, it became apparent to me that she was using these story telling hats as a way to relieve herself by masturbation and ultimately I steered he towards my providing some scripts or at least prepared things that I had written so that while she could provide comments, it steered her to imagine herself in those situations. That in turn gave me a little bit of an opening to start to dominate her online by telling her what to do and then demanding she either tell what she was doing or send me a selfie to provide she had done it. More and more she started to look forward to those session with me online and more and more I became aware of what excited her. As that matured, I started to write out some prepared scripts and things for us to entertain ourselves with on the the trip. She particularly liked stories about being in front of others in humiliating situations that she had no control of, having to either wear or use device on herself in public areas, and to having sex where there was a likely hood of being seen. She also enjoyed being in a situations where she seemed like she had no choice the matter of sex and was humiliated during her obeying someone. I figured out a variety of ways we might have some spicy intimate moments using that insight.

Over the next couple months while we were waiting for the cruise, she asked me to send her some fantasies that I had written so she could read them (I also suspect she wanted to use them for her own self satisfaction). So I spend some time working on fantasies where the single woman had been directed to expose herself in public, usually at a strip bar, an adult bookshop, or in front of random men who were strangers to her including a bachelor party. I also wrote some stories of a woman being humiliated in a variety of ways for her master being subjected to facials, being a target girl when men had masturbated on to her body, writing phrase on her body and other such things. The idea I had was to acclimate her to some of the things I might have in mind. It was clear by now that she was into exhibitionism, ***, *** (not being necessarily hurt by her master) , having videos and photos taken of her and her thinking that might be shared with others, and sex in public areas or risky situations.

When I got back from my cruise with Linda I did indeed share with Sally many of our adventures without of course making any reference to who Linda was. She was very obviously excited about my having Linda share her own photos and video with her husband as well as the fact that I had Linda share her pictures within her Private Gallery with me having access. Over the last month before we left, I pressed her a little in the games we play to move further and further in the areas of her sexual excitement. I also introduced her to the ideas of some games such as Indian Strip Poker as well as playing some games of Truth or Dare since it gave me a chance to ask her all kinds of embarrassing questions of her and giving me more information on how to best meet her needs on the Cruise. I was looking forward to this cruise tremendously and spent a lot of time thinking of ways for her to humiliated in public without actually outing her and ow to make things exciting for her. I used Amazon to purchase some devices I could control remotely as well as a number of softer implements to use in disciplining her so that I did not have to resort to the usual harsher implements I normally used.

The day of her arrival loomed. She had found non-stop tickets from her airport into the Florida airport she had chosen ( I have several within a one hour drive of my place) and I again assured her I would be there to pick her up. As she landed and was on the tarmac, she should text me so that I could leave the cell phone lot, and then proceeded to gather her bags and come out to the curb underneath her airlines sign.

All was working to plan. I had taken the dog into the Kennel that morning, we would stay at my Florida house overnight and then drive to Fort Lauderdale the next day early, boarding at around noon. As I waited in the parking lot, I checked her flight and it was on time and when I saw it land I made sure I was ready for her text. It came shortly that she was on the ground and heading to the baggage claim. I tested back that I would have the car at the arrival point for her airline.

As she came out of the airport, she was dressed in white slacks and a nice top, looking bubbly but a little apprehensive as well. I jumped out of the car and opened the hatchback to put her bags in. I gave her a little peck on her cheek and asked “Are you hungry or can you wait 45 minutes of so until we get into town?” She decided she would we wait.

As we drove I kept up a little dialogue of telling her about this area of Florida while also asking all the little things like “How was your flight?” Everything work out OK?” and stuff like that. When we got to town, I gave her a quick discussion of my town as we drove to a very god place on the water to get lunch. We sat overlooking the entrance to the harbor and had a couple of sandwiches, hers a burger and mine a fish sandwich while we made small talk, getting more comfortable with each other. I drinking a beer and her a white wine. She seemed to feel pretty comfortable as we left. I gave her a driving tour of the area as we went, showing her the beach and some of the other hi-lights of the small town and explained why I liked it so well such as the small eateries, nice diversions, and the fact that traffic was low in comparison to other areas. When we arrived at my place I parked in the garage. I showed her the guest bedroom which was hers to use as a private space as she desired and the bathroom, dropped her bags in there and then gave her a short tour of the place. I told I would be waiting for her to get comfortable thinking she might want to use the bathroom or get something more comfortable to wear, but she basically followed me to the kitchen where we sat at the table and talked for a while. I told her we would be going to dinner this evening to a nice place but that it was casual in nature so she need not change. We had a couple of hours until then so we just basically relaxed. Then we left and went back down towards the beach and the place I had picked out which was pricey but had very a very nice view and good food. We sat on the deck outside to take advantage of the night and also it was more secluded so that if she had questions I could answer them. I explained we had an early morning the next day, getting up about 5am for me and she could sleep until 6am. I would pack up the car later tonight with the bags and she could just leave out the things she needed in her carry on. I suggested she wear shorts, running shoes and a t-shirt or other comfortable top for the day since we would have our bags well in time to dress for dinner and events afterwards. She asked if we could book a couple of excursions she had decided she might like to go on and as we sat there I used my app to book them for her. I explained we would board 11am after we made the drive starting at 7am. I expected we would stop for a McDonalds or something on the way but left it for her to let me know what kind of fast food in the car she might prefer. We have all of them close by my place. We had another drink and then decided we would head back. Since it was still light enough, I took the back way into the community I live in and showed her the amenities we had such as the club house, pools etc. It was a short excursion. When we got home I sat her down at the small table where we could face each other and asked “What would you like to drink? I have beer, wine of different kinds, all kinds of hard drinks or after dinner drinks or I can crack a bottle of champagne although you will get lots of that aboard the ship.” She chose a white wine and I opened a bottle and got myself a beer. As idid I brought a pack of cards in with me and said “I hope you like to play card games because that is what is planned. I thought this would be a great way to break the ice between us. Do you know how to play Indian Strip Poker? She shook her head with almost a little embarrassing look as her cheeks flushed a little. I doubt she thought I was going to be so direct.

“It is really easy. We both get one card, which neither of us are not allowed to look at. Now the ante is one piece of clothing. We will both start with the same amount of clothing so the stakes are even. One piece of clothing equals on “Truth or Dare. So when betting, you can bet a Truth or Dare to the other party. Two pieces of clothing or two Truth or Dares equals one Challenge which can also be used for betting. So, as a practice round, we each name a piece of clothing we are betting. We hold our cards up to our forehead so the other person can see our card but we cannot. Based on seeing what the other person's card is and how they bet, you make your bets. So for example, you might look at my card and bet me one Truth or Dare. To stay in I must match your bet and call, or I must raise your bet. So you have bet one Truth or Dare and I decided to raise you considering how you bet, so I might either say two Truths or Dares or I might say one Challenge which is equal to two Truths or Dares. I could even go higher. We mark each bet down for the pot. Since you bet one Truth or Dare and I bet a Challenge, we now have one Truth or Dare and one Challenge in the pot. You can fold but now must forfeit your piece of clothing plus you must accept a Truth or Dare and you must accept my Challenge. Challenges are kind of like penalties, so it might be something like a Spanking or something else you must do for the other player. Challenges are only paid off at the end of the game. The game ends when one of us had no clothing left. We keep tabs of the Challenges you have won and you may turn in Challenges to get pieces of your clothing back. The nature of the Challenges are not revealed until the end of the game when the winner will have them all. Since if you turn in a challenge to get clothing, it is moot and neither of us will allow a challenge to go unused. Ok, so lets play a round.

I could see she thought this was silly but she was game. We were essentially playing a game that middle schoolers play although it was a little more serious than that. I dealt us each of us a card face down reminding her not to look at. “Ok, hold it to your forehead so I can see it and I will do the same but do not look at your card.” She came up with Jack. I saw her smile a little bit and I figured I had a small card held up. “Ok, it is your bet, what would you like to bet. You can either bet a Truth or Dare or you can bet a Challenge.“
“I bet a Truth or Dare”
I knew I was going to lose this round but I figured that by doing so it would help us break the ice.”
“Ok, I will call. We can show our cards now.” As I looked at the four in my hand I said “Ok, You win. So I will take Truth.”
“Wait, you said this was a practice round.”
“Oh, I will keep my ante of clothing alright but I will pay of the Truth or Dare. So ask me anything.”
She screwed up her face a little thinking of a good question to ask me and finally said “How many women have you taken on these cruises of yours?”
I acted like it was hard to come up with the number, as if I was counting them, and then said “Two but one of them I have taken twice, so really I have taken three cruises but only with two women. Do you want to know how it went?”
She nodded her head so I continued”Quite well actually. The first woman was a friend of mine who used to work for me. She was a lot of fun but things did not work out romantically between us at all. But we both did have fun. As a matter of fact, she is the woman who I invited on a second cruise that we just finished up in November. The other lady I took was in January. We had a great time. It was a vacation for her. She is married so I figure there is nothing long term going to happen between us but we might do it again if both of us are still available in the future. She and her husband have an open arrangement.”
I could see she was intrigued by all of that but did not ask further questions and I just let it lay for now. I poured her another glass of wine and got up to the get another beer for me. “Got it now? Are you ready to play?”
I guess she felt she had the game pegged but of course you never know the hand you will be dealt and of course bluffing, even with a bad hand is the name of the game.
I dealt us each another card. This time she was showing a seven but she also did not seem inclined to bet, so I figured I was holding a pretty good card. Seven is about average since the Ace is high. She when she chose to pass I decided to bet a Truth or Dare which she accepted. When we put down our cards I was the winner and she lost one of her shoes. Now we bot just had shorts, shirts, shoes, and underwear on although she wore a bra, so I made sure she threw in both shoes to make the initial start fair to me. When she had kicked off her shoes she said “Truth”.

I had already given some thought of this so I asked the question fairly quickly “What are and describe the top three times you have been the most humiliated in your life having to do with sex.”

She sat silent for a minute thinking about the question. I figured these might be good and they were.

She started her answer “Ok , the third worst time was when I was pledging my sorority in college. All of pledges had to strip down and they made us go through what they decried as Hell Night. They made us do all kinds of things the worst being with sex toys and devices, as well as kissing each other and in using our fingers on each other. “
Needless to say I had some questions to help her clarify “And did you enjoy it while you were playing with each other?”
“Well yes and no. It was horribly embarrassing but it was also very exciting since all the upper class girls were watching us and jeering a and calling us names, criticizing what we doing and telling us to do other things as well. It went on for hat seemed like a really long time but it was just a bunch of women. It would have been much worse if men had been involved as well.” I let that one slide a little. “Ok what was the second worst time?”
“Well this one is a little worse. I had let my boyfriend take some Polaroids – you know those pictures n the old days that developed themselves. He wanted nude pictures of me and I did it. After that he held onto the pictures. Of course, a few months or so later, I decided I wanted to break up with him since he was kind of a shit. When I asked for the pictures back he refused unless I perform a strip tease in front of a group of his friends. I didn't agree at first but decided a day or two later to do it with the guarantee that none of them would touch me and that he guaranteed not a word of it was leaked from the group. He got his little group of 5 friends together and I went ahead and gave them a strip tease. They hooted and hollered as I did and demeaned me a lot but none of them actually touched me at all. I got the pictures back but I have always wondered what those women think that work in the clubs.”
“Did you get excited while you were stripping?”
“Oh yes. I still get excited thinking about it and later on in college I actually participated in one of those amateur contests down here in Florida. It was one the most exciting times of my life. I felt like I was a real slut but it was really delicious.”
“Ok, so what about the worst time?”
“Well that is a pretty ***ful experience it was so bad. My boyfriend, a different one than the last one, were out parking in the backwoods to get some privacy. I was a thing we all did fro my small hometown. So anyway, I did not have my top on or my bra and I was kneeling in front of him on the passenger side of the car in this woods. Obviously someone had seen us enter the woods and it was private property. They called the Sheriffs office and they sent two deputies to investigate. So I was giving head when they knocked on the windows with one on each side of the car. They shined their flashlights into the car and tapped on the window. They told us they were going to have to give us a ticket for trespassing but if I finished what I was doing while they watched they would let us off. So I finished and my boyfriend gave me a facial while they watched. When I was done, the only thing they had said before they left was “Have a nice night now!” then they drove off. I cleaned myself up and e drove off the property.”
Having had that same situation happen to me and a girl, I doubted anyone had actually called the Sheriff. More likely the two deputies were just checking out known areas where couples parked to have sex in a small town. Of course I didn't say anything about that thought to her. Instead I asked her again if she had been excited afterwards and she said “Oh hell yes. I was truly exciting.

Now I am pretty good at playing Indian Strip Poker but from that point, it seemed to me like she was trying to lose. She did everything except fold a obvious winning hand. She bet recklessly and built up both Truth a Dares which she paid off with answers to my questions and Challenges which I turned into a spanking, a belting and a caning. She also lost all of her clothes while I still had one shoe on. It was glorious and she came out of shell in a big way, telling me all kinds of sex acts she had tried with men, about the first tie she had given a blow job, how she had tried anal and also ho her sorority ***s had paddled the pledges. It took us a couple of hours to get to the end since we talked so much. My final comment to her when she paid off her last Truth or Dare was “You were indeed a very naughty, naughty girl, a slut and you deserve to be punished as I led her into my bedroom to provide her with her spanking, belting and caning.

She had obviously been spanked, belted and caned previously since she did not flinch when I showed her the implements I was going to use. When I strapped a vibrator device into and on her she did not object and actually smiles as I turned it on low making sure she was being stimulated both inside her and on her clit. Quite honestly she took the moderate spanking and belting very well. I did make sure she had a safe word to use but I never had to give her a gesture since she never really made much noise either to make me gag her. Instead, she took the caning I gave her with the switches and light canes I had with a little wiggle of her butt and seemed to want more. I would have given her more but it was getting time for be bed since we had to get up early. She gave me a nice blowjob to finish me and then I allowed her to cum while I used a medium cane on her backside. She had her orgasm which lasted some moments and must have been satisfying. I laid her on the bed and put some soothing gels on her backside along with some Icy Hot. She relaxed while I packed things up where they needed to go and threw in a few more serious implements I had been thinking of leaving behind. When I asked her if she wanted to sleep separately since I had to get up earlier than her, she simply rolled over and got under the covers of the bed. I set the alarm and both of us drifted off to dreamland. I must have pleased her since during the night she gave me another reward.

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