Tropical Cruise Pt. 01

AN: With the blessing of the author I have created this revised version of their excellent story. If you haven't read Sethp's story Ship Wreaked with Mom and Esther, I recommend reading it. All characters in sexual activities are 18 or older. Thank you and I hope that you enjoy this story. Let me know what you think.

~*~

Ryan Donovan watched as the gangplank to the Cruise Liner he was currently standing on was removed. The ship's massive horns sounded signaling that the cruise ship was pulling away from the dock and was making its way for the tropics. Ryan sighed heavily as he followed the steward on his way to his cabin. While many of his classmates were envious of him, Ryan wasn't exactly overjoyed to be here. Sure, it was a pleasure cruise and they would be seeing exotic locals and (hopefully) sexy, scantly clad girls and women. But the notion of getting on a giant ship and cruising around the middle of the ocean, miles away from any land... or help, just unnerved him. His opinion was primarily based on watching event movies such as Titanic, Castaway, and other stranded-type movies growing up. His friends thought he was being silly as to what were the odds of something like that happening to him but that didn't keep Ryan from worrying about the possibility.

After years of spending five summers at Boy Scout camp (earning his Eagle Scout by the time he was 16) followed by months at various sports camps, Ryan had been looking forward to one carefree summer before he went away to college in the fall. Despite this being a dream vacation for many, Ryan wasn't excited to have a large portion of his summer taken up by this trip. Before being informed of the cruise he was making plans with his friends, most of whom were going out of state to various colleges. In addition to this, Ryan was hoping to finally go out with the cute girl down the street who was finally single. He was hoping that the two would hit it off well and maybe, just maybe, this would be the summer that he finally lost his virginity.

Alas, Ryan's father, Douglas Donovan, is one of the biggest and wealthiest realtors in their home state. Douglas was 5 feet 11 inches tall (only an inch taller than I was), very lean, and at 48 years old was extremely gray-haired, bordering on white. Ryan remembered his world crashing down when his father informed him and his mother of the cruise just two weeks before Ryan graduated from high school. This would be an extended cruise as Douglas was meeting several other realtors for networking. Douglas assured Ryan he wouldn't be bored and that he might meet some interesting people his age as the realtors were also bringing their families. Ryan immediately saw this trip for what it was. His father would be working while golfing, swimming, or whatever event the realtors had planned at the same time. In fact, he wouldn't be surprised if the trip would be deducted from their taxes as they were working.

Then there is my mother. Rebecca Donovan (nee Wiley). She was 5 foot 8 inches tall (two inches taller than her assistant). She was far from the typical trophy wife (like the ones he saw on the arms of his father's associates). Many of these women were slim (probably via liposuction) bronzed (via tanning beds), had really bad blonde dye jobs, and had more plastic in their breasts than their stepkids' toys.

My mother, worked out religiously at the health club with her friends and at our home gym when the girls weren't available, to keep her trim figure. My mother's tan was natural from time spent outside sunning at our Olympic-sized swimming pool (which she also used quite often to keep in shape). While my mother did frequent the salon, she kept her original Chestnut brown hair color. Sure, she would have it touched up to mask the gray hairs, but it was very natural looking and had no dark roots like the bottle-blonde bimbos. Of course, the final major difference between the trophies and my mother were her breasts. My mother has natural D-cup breasts. She was smaller before giving birth to me but based on pictures she was considerably larger than a D-Cup (from photos at the time) before finally settling at D. With her slender frame, due to rigorously going to the gym, she tended to appear a little too top-heavy, but I always she was perfect. Also, she was the only original wife of the group.

When my father announced the plans for our vacation the one thing my mother insisted on was that in addition to the three of us, was that my father book passage for her assistant to accompany us. I thought it odd but It was the one thing that made her like the trophies only their assistants were off corralling their various young charges. While there would not be as many things for Elena to do on this trip Rebecca was very insistent, so Douglas relented.

The assistant's name was Elena Domingez. She started working for my mother when I turned 13. She had light tan colored skin, so light that sometimes she was mistaken for Caucasian. During the summer when she dressed business casual, I noted her skin darkened, probably from spending time in the summer sun during her off hours. She was shorter than his 5 foot 10 inches but average for most of the Hispanics that I went to school with. She wasn't fat by any means (save for her breasts and ass). She was borderline plump, but I preferred to think of her as curvy. She had full lips, chocolate brown eyes, and long wavey black hair that traveled down to the small of her back. During working hours, she always kept her long hair braided as she had to look professional.

As I implied earlier, Elena was the proud owner of a pair of massive boobs that always seemed to be on the verge of bursting out of her blouses. I have witnessed many times these massive orbs bouncing about when my mother has her rush to go collect something or others around the house. I tended to avoid her as much as possible as she caused my cock to tent whenever she was around. From time to time, I would sit in the living room and watch her tits jiggle with a book or my laptop concealing my cock as she did this.

Half an hour after we disembarked my father and the associating families were still on the main deck socializing. I had said hello to several of the teens (all girls) and a few of their younger siblings and was ready to make my way to my cabin. Elena appeared happy to be here, but a bit put out as my mother hadn't dismissed her so that she could go to her cabin and unpack yet. As the trophy wives kept my mother's focus on their conversation I took pity on Elena and got my mother's attention. Informing her that Elena and I would be going to our cabins to unpack, I led the grateful assistant away from the massive congregation. As we made our way to the stewards so that we could find our rooms we made small talk as she didn't know anyone else onboard. Making our way down the corridors I would find myself taking glances at my mother's alluring assistant. Since this was a leisure cruise it was the first time that Elena could dress casually. As I took in her simple sundress, I couldn't help but think that she was even more striking than I had imagined in my bedtime fantasies. We made our way to the concierge desk and said our goodbyes before my steward led me away.

"Your Cabin sir." The steward informed me.

I step into the room and am surprised at how spacious it is. I had to ask the man if he was sure that I had the right room and not my parents' room. Double-checking his manifest, he assures me that this is my room. With my bags placed in the master suite, I give the man a tip and go about placing my clothes in the closet and dresser. I was just about finished when I heard a keycard unlock my door. In walks a stewardess and... Elena.

"Oh... your roommate is already here." The young woman states.

"Roommate?" I say. I came to find out later that the reason I have such a large room is that my father, to save money, booked this suite so that Elena and I would share it.

To say that I was upset with the man would be an understatement. My father, in his infinite wisdom, had managed to cockblocked me from finding any willing girl by giving me a babysitter. I wanted to scream but didn't as that wouldn't appear very mature in front of Elena. Also, what could I do at this point? We were underway and the only option was to jump ship. Not something I was willing to do until we reached land.

With no other recourse, I did the gentlemanly thing and insisted Elena take the master suite while I slept on the pullout built into the couch. The master suite was divided by a closeable door so she would have her privacy. Elena of course begged off insisting she take the outer room but being a true gentleman I held firm that she take the master suite. Seeing that I would not relent on the issues, Elena reluctantly aqueous to my request. We worked out how I would access the bathroom and how she would give me a heads-up in case my mother called her and she needed to cross into my area.

To assure Elena that I wasn't upset with her about the situation I politely requested her company for dinner. Just the two of us. She tried to stave it off, but again, I was very insistent. She relented much easier this time. I inform her that it is formal, and she tells me she has just the ensemble for the occasion as she reminds me what a stickler my mother is on appearances. I chuckle as I know only too well that fact (which is the reason I have a suit with me on a leisure cruise).

Elena and I went our separate ways for a few hours to get our feel for the ship. When my watch beeped I returned to the cabin to find Elena was already in the shower. I patiently waited for my turn and when the water turned off I heard the door open and Elena call out to see if I was there. I was sitting patiently on the bed and had a large white terry cloth robe ready for her. Extending her lightly tanned arm she graciously accepts the robe and I turn around to wait for her to exit the bathroom. A few moments later my beautiful roommate exits wearing the robe and a towel around her head. I inform her I won't be long so she doesn't disrobe while I'm trying to make my way across the room. While I won't lie and say I wouldn't mind seeing her naked (heck I'd kill to see her naked), I want to be a perfect gentleman for her.

I quickly wash up in the shower and after letting her know that I was exiting the bathroom make my way past the beauty who is sitting at the edge of her bed. She follows me to the door and smiles as she slowly closes it behind me. I swear she was blushing as I passed and let out a sigh as I caught a whiff of her scent as I passed and she smelled amazing. It didn't take me long to dress. I had your standard black suit and white shirt with tie and fancy dress shoes. Elena however was wearing a beautiful red dress. It was sleeveless with a deep V-neckline (thank you god) so her abundant cleavage was prominently on display. The skirt went down to the floor and was slit to her upper thigh. She was wearing matching red heels which made her about the same height as my mother. I am momentarily speechless but when I find my voice I inform her she is stunning which earns me a blush and a thank you. Holding out my arm, she takes it and we make our way from the cabin to the VIP Dining Room.

As we made our way to the dining area I ran into some of the teenaged girls of my father's associates. They were on their way to the club. Dressed to the nines several of the girls finally took notice of me and they boldly invited me to join them rather than have dinner with the parents. Apparently, they must have thought I was just escorting Elena to the dining room. As this was not the case, I politely turned them down. I think I bruised their egos doing this and the girls all walk off in a huff. Elena informed me she would understand if I would prefer to go with the girls as opposed to having dinner with her, but I assured her that she was who I wanted to be with at that moment. I saw her blush as I took her hand and led her to our destination.

Elena and I dined at a small private table and got to know one another for the first time in five years. She told me all about herself (I didn't know that she had just turned 40. She didn't look a day over 30 in my opinion). We talked about our lives (she knew most of mine having been a part of my life for 5 years) and during this dinner, Elena confided in me that while she was looking forward to the tropical locals that we would be visiting she hated boats. I placed my hand atop hers and informed her of my aversion to them as well which earned me a big smile. It turned out she had seen almost every lost at sea, stranded, etc movie just as I had and that weighed on her mind when taking this trip. As we continued to talk she asked me about my plans for the fall. I informed her that I would be going off to a prestigious college and was very excited to get out from under his family's reach and explore the world.

"You must be very excited," Elena states.

"I can't wait," I reply.

"I can tell. There are so many sights to see... and so many young women."

I was drinking my club soda until she said that statement, at which point I almost choked on my drink. Elena laughs initially but then begins rubbing my back as I try and catch my breath.

"I'm sorry," Elena states.

"It's ok... it's true... just unexpected."

She isn't wrong. The world was my oyster and all I had to do was survive this last family outing with my parents. As I was stuck in his floating city, I prayed I could find a sexy and willing girl to hook up with and finally lose my virginity.

"I'm going to miss seeing you around the house when you're gone." Elena offered.

I was shocked really. I didn't know that she noticed me while going about her daily routine. Still, it was a heartfelt statement, and placing my hand atop hers, I swore I felt a spark pass between us. "I'm going to miss seeing you every day Elena."

We sat silently for some time before we finished our drinks and then returned to our suite to rest up for the next day.

The first few days of the cruise were fairly uneventful. During my time on the ship, I managed to stay clear of his parents and their associates. When she wasn't working for my mother I made time for Elena who had not made any connections with the other passengers. Sure, many guys made passes at her but it was obvious that they were only looking for a one-night stand or a short-term fling on the ship. Elena was having none of that. We spent most of our time together at the pool deck sunning and swimming. My mother gave Elena all of Wednesday off (something I learned from her at Dinner the previous night). I decided to be adventurous as we were nearing our first island stop. I set my alarm earlier than I was used to getting up. Elena had the shades drawn so as not to be woken up by the first rays of the sun. Sneaking into her room I go through her wardrobe and find her swimsuit. I'm disappointed that someone as beautiful as she is opted for a simple black one-piece bathing suit but I have to make due with what we have. Bathing suit in hand I plop down on the side of the bed beside her and she is startled awake. She pulls the covers up as she is wearing a simple black Chemise (ok... I looked).

I inform my roommate that we are going out today. I leave her with the swimsuit and tell her she has five minutes to get ready or I'm coming back in no matter what state of dress she is in. She obviously took me at my word as exactly five minutes later, the very demure-looking Elena exited the room in her swimsuit and a sarong that I didn't realize she owned. Taking her left hand and dragged the older woman to the back of the boat. Elena is perplexed and has no idea where we are going until we arrive at our destination. We are the first to arrive and thus the first to select and take out a jet ski.

Elena was very cute as she tried to back out of going with me. When she realized she was not going to be let off the hook, she tried to get me to select a side-by-side Jetski but again, I refused. Climbing on, I insisted she get one with me and helped her onto the seat. Her body felt very warm as her arms came around my waist. I reeve the engine and soon Elena is screaming as we rocket out of the back of the ship.

As we bounced up and down in the water Elena held me close. The screams initially were ones of fright before she eventually let herself go and began enjoying the ride. I was smiling the whole time as her large abundant breasts were pressed into my bare back. The faster we went, the tighter her arms were wrapped around my body. Soon her hands were firmly pressed into my six-pack abs and chest. I had to admit, this was the best part of my trip to date, bar none. I began to wonder why I hadn't done this sooner.

Wanting to keep in shape during the trip, I would get up early in the morning and work out at the ship's gym for an hour or two. Depending on how many people were present factored into how long I worked out. At such an early hour I usually had the run of the place. Occasionally someone would join me but very rarely and usually they were guys. The only good part about that was that I had someone to spot me while I used the bench press.

Friday morning was the first time that I ran into Elena at such an early hour. She was usually still asleep and by the time I returned she was awake and running errands for my mother. Fate seemed to want to bring us together as I ran into Elena coming out of the gym. She was in a hurry for some reason or another and I accidently bumped into her sending her crashing to the ground. Apologizing profusely, I help her back to her feet. My mother had sent Elena on a fact-finding task, and she was making her way back to my parent's cabin with the information.

Ryan was so concerned for the older woman, that he didn't realize that Elena was going through an existential crisis as she looked up at the handsome younger man. Her voice was failing her as she took in Ryan's amazing form. She had gotten only a glimpse of how he had matured over the years as she was usually too busy to see him at his house. Their first day at the pool and every time since she would get choked up by how much of an adonis this young man truly was. Also, unlike many men with his handsome looks and physique, he did not act like God's gift to women. He was very down to Earth and level-headed. As she stared up at the young man hovering over her, Elena couldn't help but admire Ryan's build. No longer was he a gawky little boy at 13 but within the year had sprouted several inches. By the time he was 16, he had grown to his current height, towering over her and slowly muscling up. Ryan's physique reminded her of Bruce Lee. Not bulky, very slim but well-muscled. Ryan helped her back to her feet and in such close quarters, she couldn't miss his sweaty, masculine musk. Once she was stable Ryan stood aside so she could continue on her way.

Elena gave him a warm smile as she passed. Before she could get on her way he stops her in her tracks and asks her to join him for dinner, just the two of them. Elena smiles and agrees. Not realizing it at the time she promises to buy him a drink later, a real drink, as a graduation present.

As he watched her pass Ryan marveled at Elena's shapely backside. Leaning back against the wall he smiled and thought how she was the only person in his household that he was going to miss when he went away in the fall. Yes sir... he did like her.

As the trip progressed, Ryan eventually managed to meet several teens that he was surprised to find were going to the same college he was in the fall. Currently, they all had plans with their families for the evening but made it a point to go out the following day. Ryan saw that one of the girls, a nerdy but very cute (think sexy librarian) was smiling and blushing at him. She lingered behind just long enough to whisper her name (Kelly) before racing off to rejoin her group.