The Bruise Cruise Part 2

[ve****]

The meetings overall were great. They were designed to put the minds of the women at ease and that I was no a crazy lunatic. I would meet them in neutral places so they were comfortable. If they came to me then it was in a coffee house or a restaurant. I did not try to wow them with lunches or dinners but instead just coffee and a danish or something of that nature. When I went to their towns, we would meet in a place selected by them or in the case of me taking a flight, we would often meet in the hotel I was staying at, normally the airport hotel which always had some kind of little restaurantI or bar of some kind. We wold chat about their likes, dislikes and they got a good look at me with all my warts exposed and of course the reverse was true as well. I never expected or pressed the to have sex with me when we met, instead of allowing them to make the offer to me if they wanted to move further into the game. I ended up making 5 flights to various cities around the country, usually staying overnight and only twice did I have sex with one of the interviewees. Instead, my intent was to find someone who I would be comfortable with for a few days even if the sexual chemistry did not work out. Again it, it was a risk that had to be assumed. In the end of chatting online, on the phone, and in person, I ended up with a total of six women who made my cut and I made my invitations to the women in the order I thought I preferred. Of course, my preferences were not the most important part. We also had to arrange schedules for them as well as for me. Although I have few responsibilities, I have some. All of this kept me quite busy for a couple of months and I had not even arranged the cruises we would take. This was something of a benefit since I did get some discounts for late booking but sometimes the amenities were not as high in quality as I might like or the cruises or destinations were simply not available for scheduling purposes. That process ultimately left me the three cruises. Remember I was playing the long game, what I wanted in the end was a list of prospects who I could call on in the future as well as the initial three cruises. So the time and effort was well worth it in my mind. I had some people who I could ask to accompany when I found good deals or great cruises or premier cruises an then see if any of them wanted to schedule. I felt I got that list. On top of that, it gave me the opportunity to put together a spreadsheets of desires each lady had, wants, dislikes, and other it3ms. It also helped me to hammer out the rules, benefits for them, produce what I wanted on each cruise. In other words I was able to personalize the experiences for them.

I realized up front there wold be difficulties inherent in the process and the actual execution so I had to guard against getting my hopes too high and guarded against theirs getting too high as well. I meant to under promise and over deliver on both counts although at first I would tend to perhaps curb my enthusiasm. I wanted to indulge them and not make too may demands on them in the process. I also wanted to ensure that we eased into our intimate activities and concentrate ore on getting to know them as people,preferring to have them like and enjoy what they were doing than to *** them into situations where they were having second thoughts. Again, I was in it for the long game. The perfect companion for me might be out of reach but a choice of several was within reach. If the perfect one came along, the other might fall by the wayside after we had cruises together. I had a goal of several years of cruising, preferably with one companion but ultimately if not that, then with people I liked if not loved.

The first cruise started to loom. I had another great cruise in November with my friend, It served as something of a test case again. Spoiling her just as a good friend, making friends aboard, tuning how much her allowance would be for gambling, how we arranged her excursions and other onboard amenities and what she liked to do. How I would schedule around thing she liked to do such as shows and other events aboard. As always she had a full package set, with onboard spending and the tips and other charges coming to my credit card bill. It gave me a chance to make sure the things I promised could be made true. The cruise with my friend was great despite no sex involved again. We laughed, lapped up the good life and gamble together. She had a great ie as well visiting ports she had not been to before which I had scheduled at her request so she cold see some new things. All in all a great test case and some ore lessons learned. Now I looked forward to the first real case.

Linda was the first woman. We had met in Florida so hers was an easy one to pick and schedule. We had hit it off well and she was eager to be pampered. I set up some massages and a Spa day in advance for her which included hair and other beauty stuff for a night when we would go to specialty dining which was also a dressy night. Since she would not know anyone when we pulled into the first port which was the cruise line owned port catering to a much younger crowd with para sailing, beach cookout, skidoos, and such as excursions. Instead I talked her into staying aboard, getting a massage, meeting new friends around the ship and I would accompany her around instead of working as long as she wanted. I wanted her to be comfortable in her surroundings.

I picked her up in her town at the bus station where where had parked her car and we chatted on the 45 minute drive to my house where she would stay in my guest bedroom. We had drinks before dinner and then went out to a nice restaurant. When we arrived back home, I served after dinner drinks and allowed her to re-pack some items while I gave her some hints on what she might not need and found things for her she had not though of. We had to make a little Walmart pickup. We chatted through the evening and even played some little games as icebreakers like truth or dare and a form of Indian Strip poker whichI enjoy and while we ended up half dressed, I did not press into sex. Instead she came pretty willingly to my bed. I gave her a light spanking and we enjoyed the closeness of the moment. Again, I preferred to keep it slow. I did have some more severe implements and devices that we out in the bedroom so she saw them as we were in there. When we were finished I reminded her we would be getting up early and she might prefer some privacy if she wanted to retire to her room. She did and we went to bed separately. I did remind her that she should contact her husband, tell him she was sage and that she would not be able to contact hi as easily as we were on the cruise despite out internet packages since it was via satellite and often unreliable. What she told him about the trip so far I had no idea. Linda was a real beauty. She was slim but had nice breasts. A natural blonde and cute. Very athletic looking and blemish free. A tattoo here or there and nipple ring piercings. I wondered why they vacationed separately. He was lucky to have her. Their ids were older now and out of the house. I guess perhaps it was their time to sow some oats.

We got up the next morning at 5am, packed out luggage into the car and drove the 3 hours to Fort Lauderdale which was a familiar route for me, munching on McMuffins on the way. When we arrived, I dropped her off, gave her a $5 bill for the porter and dropped the bags for him while I went to park the car. We boarded without incident and found that our room would not be ready for about an hour or so and went to have lunch on the 9th deck which was the Lido deck. On the way I told her about the ship and how to find her way around since it can be a little confusing. When our room was finally cleared, we went down to our room to do our safety brief, check on our luggage and get used to the room. Linda was visibly impressed with the room although it was one grade down from the level I had asked for but had been sold out. No concierge service for us but there was a nice bottle of champagne on ice, some goodies from the Casino and of course it was large and spacious. The deck was large. Our luggage had not yet arrived so we would go to our life station, check in and then decided to tour a little and then have a drink in one of the bars on the third deck until we started to head out to sea. I showed her the large auditorium where the hows were, the casino, where the dining room was and which we could use almost any time but explained that there were lots of smaller venues s well and the lido deck always had things out as well as served a huge set of different varieties of food for each meal. Then we went a dec up and I showed her where the shopping was and explained that she had an onboard credit she could spend in anyway she wanted to buy small gifts or souvenirs. Finally we went to a bar that I knew was open and sat and had an afternoon cocktail. We left the dock at 4pm exactly and moved towards the ocean. Now the crowds were thinned out for the elevators since everyone was settling in. We skipped the Bon Voyage party on purpose since it was just a crowd of people drinking on the 9th deck around the pool. Instead we went to the room to unpack before dinner. I had all her measurements and had arranged for some clothes for her two wear l some costumes. I laid out a very nice forest green outfit under which she could fit amazing lingerie I had bought her that was very sexy. She found it nice that she was able to take the clothes with her since they were in her sizes. I had also bought her a little maid outfit, a SchoolGirl outfit and a sheer harem outfit for our use in the future as well as another dress and lingeries set for a future dressy night.

She came out of the bathroom dressed in her stockings held up by garters by the crotchless green bustier which displayed her breasts on a platform bra. Green shoes just the right shade would complete her outfit. We inaugurated leaving port by toasting each other with champagne, a little bit of paddling and spanking and then a romp on the bed. As I said, we were still getting used to each other. Neither of us were really hungry so we went to the lido deck instead of the Dining room.. We had a drink with our dinner from the bar setup and then picked at some food we got at one of the stations. Then it was down to gamble for a little while tonight. We played Roulette just to see if I was lucky and walked away $200 down – a hundred for each of us. Then we went to the slots and I picked out a couple of games I knew that had seats open next to each other and chatted as we played, neither of doing much good but not too much down. She hit a small jackpot and I sowed her how to bank it on her card and explained how she should manage her ***. It went like that for a while with us moving machines to find new things and see if we could get lucky. My experience has been that you normally can find hot machines for the first couple of nights before they dialed back down. She was gambling at a low level and I was gambling at a high level when I finally his a pretty good string of luck. We had to stay on that machine until it got cold again which we did. She still moved from machine to machine in the row of machines but not far from me at any particular time. We had drinks as we gambled. I was playing the fee play the Casino provided for me so I was still up when I hit the hot streak and I ended up being about $300 ahead of break even when it went cold. I explained to her we had a couple of choices, we could shift machines again to keep playing to find another streak or we could goto a club or onto the Lido Deck for late drinks or we could head back to the room for a session. I reminded her that she had a massage the next day in the morning and that we would have all afternoon to gamble since it was legal in the waters around the island. She opted we go back to the room. On the way, I bought myself a couple of Manhattans and two white wines for her. We carried them up to the room. When we got to the room, I ordered her to take off the dress but leave her lingerie and shoes on. She stripped down really enough while I prepared for her session. I marked out her spot on the floor and ordered her to stand in her little square marked out by duct tape I had brought with her hands behind her head. I recorded her body with phone camera. I pressed her forward so her hands were on the bed and inspected her body with care and with my hands taking time to explore areas I had not been before. When I was done, I gave a her a nice spanking to warm her bottom up and make her excited. I placed my fingers into her to see how wet she had become and was pleased to see she had heated up. I used a vibrator on her for minute or two to retain the heat and then inserted a remote control butt plug into her ass which she took well despite it's size and she moaned with pleasure when I put pressed the button on the remote. As I did all of that I explained I was going to test her *** limits for a while increasing the impact on her ass with the different implements and I showed her the paddle, belt, and cane I was going to use on her explaining that if it approached the level when she really could not take any more then she say her safe word and I would pause until we talked it out and got it sorted. I also however told her that I wanted her to take the *** and I would watch carefully to make sure she could.

I decided to use the belt first because I wanted to see her welt up from the edges of the belt knowing it would sting but not bruise too deeply. I struck her pretty hard with the first blow and she took it well so I started to build up to where I anticipated she could take it. She started to roll forward as I hit her on the ass with it and uttered a few groans and grunts. I cautioned her not to make too much noise since I did not want to gag her. I checked her slit, reminding her that she was not allowed to cum until she had permission. Without a gag she could ask anytime but if I gave it or not was in question. My fingers came away slick. She was getting heated up. I decided to make her maintain that heat and fitted a clitoris stimulator on her that was combined with a dildo that could be strapped on. Then set it on low and told her to control herself. She was wiggling around a lot.

I had her kiss the paddle to acknowledge what she was in for next. When the first one hit she squealed like a pig and I told her to settle herself and brace herself for the next one, a little harder since I wanted to put down some deep bruises on her ass. She was having a hard time with the paddle as some girls do. She was small and the paddle was big. When it hit with *** she could not bear up to it and so either had to rock forward onto the bed or stand up. Neither was acceptable and I told her to “Stand Firm”. By now tears were streaming down her face spoiling her makeup but exciting me in the process. I love to see the makeup run down the girls' cheeks. After a few more licks, her shoulders wee shaking and she was working hard to keep it in. I decided she needed a breather so I decided instead to play with her breasts for a while until she settled down. I pulled up a chair, had her turn around and kneel in her spot. While she was down I had her again put her hands behind her head so I had unfettered access to her ringed nipples which I made erect using some ice from the ice bucket. Then I tugged and played with them while she groaned in some agony or perhaps pleasure. I fondled her as the vibrators continued unabated inside her. I had her stand up and spread her legs so I could check to see how wet she was and found she was dripping. Clearly she was not going to last too long after this so I asked her if she was ready to try to the cane. She answered she had never been caned but she was willing to try it. Again she went over the bed on her hands. I showed her the medium cane I was going to use and made her kiss it. Then I reminded her she was not allowed to cum without permission. She nodded her head she understood. When I laid the first stroke she rocked forward and emitted a loud yelp. Again I cautioned her about noise or the gag would go on. She nodded her her head as I checked her wetness agin to give her a little more of a break and let the *** set in. Then I provided her with 5 more strokes measured in strength to give it a little harder each time. By the time the sixth one arrived, he head was coming up as I hit her and noted she could go a little hard but not that much harder. I told her I was going to give her three more with increased strength and then three rapid fire ones and she would be done. I gave her the next three, each harder than the one before and then asked if she was ready for the final three and she nodded her head. I asked if she needed a gag to stay quiet and she nodded her head so I put a penis gag in her mouth. Just before I started again I increased the strength of the vibrators and got her moving her butt again. “Ready?” She nodded her head. I gave her three fast strokes as hard as I could across her ass. As I did, she rocked forward twice and collapsed on the bed with the third stoke, curled into a ball as the *** hit her. As it did, she tried to call out and I gave her permission to cum. She had a good orgasm. I decided that was enough for a first night and decided to take my pleasure in her mouth. Again, she knelt before me like the slave she was and serviced me. I used her head the way I liked. I had her get me down her throat firmly and held her down on it to ensure she could take and then had her give ling strokes up and down until I was ready to come. As I came I told her to accept it in her mouth and hold it. I spurted my cum and told her to keep her mouth open so I could see it. I took a picture of her mouthful of cum and then told her to swallow which she did. Then I had her clean me up making sure she cleared the vent at the end of my dick. She did a nice job and I told her “Good Girl” and patted her on the head. I made her stand in a corner to cool her ass off for a bit while I sipped on my Manhattan. When I released her from the corner, I handed her one of her wines and pated her to lie down on the bed so I could put some gel on her ass to sooth it. I slipped my fingers between her legs to give her another orgasm. Then we sat in bed, chatted, ate some chocolate covered strawberries courtesy of the Casino while watching a movie. As the movie went on, she slipped into drowsiness and I whispered, “Think what the masseuse will think when she sees your ass tomorrow.” She opened her eyes a little and winked at me.

[Zo****]

Man, I just love your Stories 👍

[ve****]

Thank you so much.