Cruising With The Crazies

(This story is loosely based on my first cruise, obviously the names have been changed to protect the innocent and I'll leave it up to your imagination as to what is real and what is not, you may be surprised! If there is enough interest, I will submit more of the story. It does become more involved with more people as it goes on. )

It was my first vacation in 6 yrs. My first vacation since my marriage broke up. I had given my travel agent (one of my best friends from college) carte blanch as far as choosing what type of vacation I was going to have. It was going to be a last minute booking, although I had already arranged with work to be off then. I've basically worked seven days a week for the past 6 years. With my marriage over, I buried myself in my work. It was my way of coping. My ex, Debbie had gone on a girl's vacation and came back and told me it was over. No warning, no previous "I'm not happy anymore" no signs or signals that I could even see looking back. It was a horrible end to a 10 yr marriage. I was devastated to say the least. I hated women and decided to have nothing to do with them until I felt good about myself again. I'm no stud, I'm 58 yrs old, 6'3", slimish build, with grey hair and goatee. Basically I had the classic dad bod.

Besides work, I loved walking. I walked 5 miles a day to stay in shape. I met a lot of women on walks and yes, I got laid often enough. I just didn't want any relationship. I didn't golf or anything like that, I just walked and stayed to myself when not at work mostly.

It was Thursday afternoon when Bonnie my travel agent called. "I got a killer deal for you!"she announced. "How would you like an 11 day cruise to the western Caribbean?" Flight, hotel, cruise fare, drink package,spa package, and all gratuities paid for up front, $4500 US?" it was an all in one breath statement.

"Whoa! Breathe" I said. "It sounds great to me. When do I leave?"

Your flight leaves Sunday morning, you'll spend 2 nights in southbeach Miami and leave from there. Then you'll fly back home on the Saturday 13 days later. Do you want me to book it?" She asked.

"Yes, yes, a thousand times yes." Was my response. I had never been on a cruise before. And 2 weeks off work was going to be great. I went home and packed. A lot of shorts and t-shirts, socks, limited underwear(I hate wearing them, I prefer to let the boys hang free), and a few dress pants and shirts and my favourite tie. I figured that would do.

Sunday morning came quickly, my taxi ride to Hopkins International was ontime and pleasant enough. I waited in the airport lounge for about an hour before my flight took off without a hitch. A taxi to the hotel, and I was kicking back with a beer on the balcony by 3pm watching various NFL games on the television. The two days in Miami flew by. I watched TV, drank beer and sat on the balcony smoking cigars as i was watching all the scantily clad Latinas walk by. I've never seen so much ass hanging out of shorts shorts as I did that weekend.

Day 1

I woke up at 6:30 a.m., my usual wake up time. I had a port transfer booked for 11:30 a.m so I figured I had plenty of time. I sat up in bed contemplating my next move. My morning wood was informing me that I should go pee, but I was a little too comfortable to want to get out of bed so I fluffed up my pillows sat back and grabbed the remote. I flipped through the channels on the TV watching news bits and infomercials until the urge to urinate was almost overwhelming. When I got back to the bed it was only 7:15, I still had plenty of time. Looking out the window, it was an overcast day, no sense sitting on the balcony, nobody would be out and about this early today. I continued flipping through the channels and landed on a soft porn channel playing "The red shoe diaries", this episode, a muture woman making love to a younger man, fantasy stuff I thought, like "Dear Penthouse". It was okay for porn, I'm more used to the harder stuff, but this was doing the trick. I could feel my penis shift under the sheet, gliding along the fabric as it filled with blood moving into a more upright position. It wasn't long before I had a light grip sliding up and down on my shaft. I matched my stroke speed to the apparent strokes on the TV. I watched as the older woman's breasts bounced up and down while she rode her young suitor, then as he mounted her from behind and when they shifted positions once more to missionary style.

I tried to time my release with the TV and had to stop a few times to let the young gentleman in the show catch up. There wasn't really much of anything other than tits on the TV, but it was more of what was suggested, still, that suggestion was making me feel good. I was two or three strokes behind the young buck as he evidently filled his mature lover and I ejaculated over my belly. That felt pretty good I thought, probably a good thing seeing a I wasn't sure if I would be doing this every evening on the cruise or if I would be bored out of my skull every night sitting by myself in a crowded ship. It was 9 am when I got my ass out of bed and into the shower and cleaned myself, got dressed, repacked my luggage and headed downstairs to check out. The receptionist informed me that my shuttle was on time and that if I wanted, I could sit in the restaurant and enjoy a complimentary breakfast. I did so, and enjoyed a wonderful stack of pancakes, 2 eggs, toast, bacon, and coffee. I finished in time to head back downstairs and watch my shuttle pull up to the entrance, there were 13 of us waiting to get to our cruise ship. Among the group were a few older couples, a few younger couples, a lesbian couple and myself. I spent the half hour bus ride glancing around at the women, their chests jiggling happily as the bus bounced, and rolled its way to the port.

Boarding the cruise was easy but took a long time. My scheduled check-in time was at 12:30, and when I got to the dock, the lineup was incredibly long. Multiple check-ins with my passport, body scans, luggage checks, and finally the reception desk where they took my picture and gave me my pass key, my itinerary and a cretificate for a complimentary bottle of white wine. Again it was about 3pm when I had my first drink, an AMF, in my hand. I wandered around the ship, checking out all the bars, the pools, and the walking track. I was taking everything in including some of the bathing beauties that had already slipped into a bikini and were basking in the sun. I stopped at the spa to find out what my package included. Apparently I had 4 massages booked for me. Did I ever mention Bonnie was a fantastic travel agent?

My first massage was early tomorrow morning. I spent the rest of the day drinking AMFs, wandering around the ship and talking to people around the pool and bar side. I ate at the pool side buffet, enjoying a cheeseburger, some potatoe salad and veggies, with fresh fruit for dessert. I watched as we left the port at 6 pm, watching all the people from shore and the ships we passed wave as our ship took to the open seas. At 7:30 pm I decided to head to my room and get everything settled. Once all my luggage was unpacked, organized and stowed away, I sat out on the balcony watching the ocean waves and sipping my drink, my fifth or sixth one since getting on the ship. It was dark on my balcony and hot as hell. A slight breeze but humid and sticky. I looked around, and decided to shed my clothes and sit on my balcony nude. It felt amazing, no one bothered me or sat on the balconies next to me. Although they were somewhat private, if you really wanted to see your next door neighbor, all you had to do was lean over a bit further. I went to bed around 11 pm. I was tired and had an early appointment for my massage.

Day 2

In the morning, I did my usual routine. Shave, trim my goatee, brush my teeth, go in the shower, soap, shampoo, and shave my balls. Yes, Debbie had requested it once, a while back, and I can't get past the stubble after 2 days. The itch drives my crazy. I dried, put on a pair of shorts, a t-shirt, donned my Olukai flip flops, and headed for the spa. Delana was my massuese, a small Phillipino lady a bit younger than me, but cute. I filled out the paper work, signed the documents, and listened to her broken English explaining my massage treatment. When she was done, she told me to undress and get under the sheet, she would be back in a couple minutes. I qustioned her before she left, "All my clothes?"

"Yes please Mr Bob, it makes it a bit easier for us." After she left and closed the door, I dropped all my clothes, placed them neatly on the bench, and hopped under the sheet face down. This was my first ever massage like this. I've had therapeutic massages before but never one that I had to be nude for. I was intrigued for sure.

She came in two minutes later "Okay, Mr Bob are you ready?" She asked

"Yes I am anxious, I've never had a massage like this before!" I stated.

"Just relax, and if anything hurts just tell me. This is a deep tissue massage so there might be some slight discomfort with it. " I was told.

She started on my legs. As she folded the sheet back to work on my right leg, I kinda felt that I was a little exposed back there. I didn't say anything, and besides, her hands felt really good on my calf muscles. I stand all day at work and this felt wonderful. I was a little shocked when her hands massaged my ass cheek, and could have swore her fingers made contact with my nut sac. She did my entire back side and then told me to flip over as she held up the sheet. I rotated and layed on my back. She covered my eyes with a warm wet cloth that smelled vaguely of lavender(probably a good thing, she was cute and my mind would have wandered) and she began on my right leg again. I'm sure I was partially exposed as she moved the sheet again. Her hands rolled over tight muscles in my thigh and i flinched. "I'm sorry Mr Bob, your legs have very many knots in them. I will try not to press too hard, but they need to be worked out. " she said. I told her not to worry, it only startled me a bit and got her to continue on as she was doing. She started once again with renewed vigor. After a bit, I again felt her hands brush ever so slightly against my genitals. I said nothing, but I could feel my body reacting. My cock was definately enjoying the massage. As she moved to the other leg, I could feel my semi hardon shifting underneath the sheet. I felt the need to apologize and said to her " I'm sorry, it's just your massage feels so good!"

"OH, no worries Mr. Bob it is completely natural, we see it all the time. We just ask that you don't try anything else. She said

I told her" I promise, I won't. I have never had a massage like this, it feels really good. "

The massage ended after 1 hr as scheduled and I dressed and went on about my day. I had a good breakfast at the buffet that consisted of bacon, eggs, hash-browns and a cherry filled crepe and of course a few cups of coffee. I filled up my big Yeti with water and went back to my room to shower and relax. The hot water from the shower felt wonderful as it cascaded over my body. I washed off all the massage oil, washed my hair and stood under the hot water for a bit. I shut the water off, dried off, took care of the after shower rituals, and then decided to have a nap. Three hours later I left my room fully refreshed again and headed to the pool side bar. I mostly people watched for the afternoon, and by people, I mean all the bikini babes. I chatted with the bar tenders and met a few people. We laughed and joked and after much discussion, decided to meet them for dinner at the main dining room. Dinner was wonderful. I enjoyed a wonderful seafood pasta with a glass of red wine and a peach cobbler for dessert. Afterwards we headed back up to the poolside bar. Our group was loud and obnoxious but people around us just seemed to be drawn in by the fun and raucaus laughter. I was pretty drunk by the time I headed back to my room, I barely managed to get undressed before passing out on the bed.