The Cruise
A Short Story
By Maryanne Peters

It was my last year in Middle School and because I was off to High School across town at the end of summer Grandma offered to take me with her on her cruise around the Caribbean. I had been to camp in the first couple of weeks of July saying goodbye to some friends who would not be going to the same high school, so I had the time to be with her later in the vacation period; plus, I liked my grandma and liked being with her. She was a stylish lady and a young sixty-eight, whereas my Mom was an old forty-one and struggling. Both my older brothers were working over summer, so in any event there was no chance of a family holiday.

I went around to Grandma’s place to wait for the cab and she insisted on repacking my suitcase while I watched tv.. She is very organized and I just let her sort things out. I was just wearing jeans, but she insisted that I wear some new trainers and a sweat-top that she had bought me. That was nothing unusual, except maybe the big patch on the front of the top. My grandma buys me things all the time. Mom says it is all we ever get out of her.

It was not until the gangplank was up and land was just a green strip on the horizon that I learned that things were not going to be anything like I planned. I just figured that I would hang around the pool and catch some sun, and spend plenty of time gaming, and then stay with Grandma on any excursions.

Our cabin had twin beds, but a bathroom for privacy, so it would be no problem sharing. It had a desk with a computer screen and there was internet access which is all I wanted. It was just that Grandma did not buy the data package. She had other plans for me.

My hair was long. Mom did not like it long but Grandma always said she preferred it that way, and Mom said that as the favored grandchild I should go along with it. The first thing that Grandma required as it got closer to dinnertime, was that I wash my hair, and that I use her special shampoo and conditioner.

“We need to make a good impression for the ‘Welcome Aboard’ Dinner”, she said.

It was not until I got out of the shower and saw my suitcase open alongside hers, that I knew that I was in deep trouble. There were none of my clothes in there. My case was full of girl’s clothes. I checked hers, which was full of her stuff. My stuff was gone.

“Ever since you were little, I have known that you have secretly played with my stuff,” she said. “So, while we are on this cruise, you will not be my grandson Timmy, but my granddaughter Cindy. This is my present to you, Sweetheart. By the time I am done with you, you will be the prettiest girl on this ship. So just relax and trust your old grandma. Tonight, you will wear what I have laid out for you.”

Sure enough, on the bed she had laid out panties, stockings, a strapless bra with gel inserts, a slip, ballgown and a pair of heels.

“Grandma, I wasn’t playing with your stuff,” I protested. But as I said, I have always admired her style. Is that really cross-dressing? I was just … well, it did not seem perverted to admire her clothes and her makeup. It was not sexual or anything weird like that.

“I am going to blow dry and brush your hair and put it up in a bun,” she said. “It is such beautiful hair. You know how much I have admired it. I have always longed to have you let me style it. Now we have the whole trip to do that.”

I was trapped. She had planned this. There was not a stitch of my clothing aboard. Even the sweat top she had bought me was now missing the patch in front and was emblazoned ‘Sailor Girl”. The last pair of my pants had gone out the window and was now floating in the sea. There were only girls clothes and we were at sea, now miles from land. and she was blow drying my hair.

“Grandma, I can’t go out on deck like this,” I whined, when my look was starting to take shape.

“You look gorgeous,” she said. “We will attend dinner in the main dining room followed by the dance in the ballroom. You will be like Cinderella and I will be your fairy grandmother.”

“Except I’ve got a cock, Grandma!” It was about as crude as I had ever been with her.

“Nobody will know,” she said reassuringly. “And I have a special bikini gaff to make sure of that.”

I had no idea what she was talking about, but I was to find out the following day.

But in the meantime, we were both getting ready to attend the formal dinner, and her excitement was almost infectious. And when I looked in the mirror and saw the grumpy look on my face, with a pendulous bottom lip extended, I saw something that startled me – I saw that I was pretty.

It was like falling in love with myself. I looked at the person and I wanted her. I wanted her to look at me the way she was looking at me now.

I think Grandma saw it too. She said: “You’re going to have so much fun being a girl!”

I made a show of shrugging my shoulders and being reluctant, but the truth is that I was looking forward to stepping out of our cabin. Maybe it was like: “What the hell?” but I thought it could be exciting, or at least a bit of fun. I did not look like a boy, so how bad could it get?

Grandma gave me instructions on walking and also on how to keep my arms close to my body as a woman should. When we sat at the table she whispered little corrective instructions, but always in a happy way. I could see how having me as her granddaughter was a real joy. That made me glad.

As a regular cruise-goer Grandma was invited to sit at the large Captain’s table, and with Grandma next to him on my left I was sat next to another young person, Mabel on my right, and across the table were two young men, Nathan and Roop. I was introduced to the captain as Cindy, the granddaughter of his favorite passenger. I smiled at everybody.

“We’re going to have such fun on this trip,” said Mabel, who was very keen to make friends. “It will be like one long sleepover. And there are boys over there staring at us.”

She was right. I could see that just giving them a glance made them fidget with pent up excitement, and a smile could make them almost swoon. It was all very odd, but it was fun.

I had to lie, of course, but I was pretty good at that. Even at that age I had heard that the best lie is to stick as close to the truth as possible, so I did. I had been to camp and now I was on a cruise with my grandmother before starting high school, it was just that I was Cindy.

“Your grandmother asked that I sit you young people together at the table tonight,” said the Captain. “You all come from very good families so you can expect to have a seat here every night, but you may want to dine together in the future.”

I hardly felt that I was from a good family, but it seemed that the others were, although none of us had met each other before this voyage. It soon became clear that we had little in common with the older guests and after we had dessert, we asked to be excused so that we could go on deck together.

We just talked. Mabel was there with her mother who was a divorcee who took high class cruises in search of a husband. Nathan was an only child, and he was travelling with his parents who were from a wealthy family of jewelers. They sat at the end of the table. Roop was short for Ruprecht and he was from Europe. He was travelling with an uncle and staying in a three bedroom suite. His uncle had chosen to dine in the suite, but he was keen to mix. He said that the trip was for education and to improve his English, but the truth is that he spoke our language better than we did.

It was late when I got back to the cabin, but Grandma had waited up. She took down my hair and had me brush it.

“I have a feeling that you enjoyed being a girl tonight,” she said. “This may be your last chance to be like this,” she said. “It won’t be long before your body changes and you will become a man. But right now, you are in a between space. It is where your sex is not obvious; where you can sway the other way, even if only for a few days. You will never get a better opportunity to look at a life that I have always felt privileged to live. I have loved life as a woman. A grandmother wants to share with those who follow her the very best things in life, and this is one of those things. You can have a moment in the starlight, as long or as short as you like. But this is the best time. It will be so difficult to do after you get muscles and whiskers, and you lose that beautiful voice of yours.”

Somehow the idea of having muscles and whiskers, which I had always looked forward to, seemed suddenly rather disgusting, especially when I looked at my smooth unblemished face in the mirror and saw my long hair shining in the mirror light.

I had a dream that night that I was a girl. I was wearing a prom dress and I had two boys asking me for a dance – Nathan and Roop. It was a wonderful dream.

Grandma introduced me to the gaff and showed me how It could hide away my bits and pieces. She had a swimsuit for me with a little frill in front just for insurance. I was happy to wear it to the pool but I was still a little uncertain so I wore a sarong. In the top half of the swimsuit she had some slight padding that gave the hint of early breasts. Somehow that made me look more mature, and I wanted that.

“But never forget that you are still a child,” she said. “As I told you last night, there is a fork in the road ahead of you as you start high school. The road bears left but there is also a right road open to you.”

I had no idea why she was saying any of this stuff to me, but I have always loved my grandmother and tried to please her, and it is not because she is rich and my parents are poor – it is because we have always been close.

She helped me put my hair in a ponytail and add a little mascara before I went to meet my new friends. It made all the difference.

That day we just explored the ship. That was a day spent mainly at sea, but the days that followed included stops at Caribbean Islands with shore visits and outings. I spent time with my grandmother, but she was happy that I should spend time with my new friends as well.

Everyday she would pull from my luggage new outfits for me to wear. You might think that a grandmother would have no idea what a girl my age should wear, but the reality was that I had no idea. Grandma had obviously researched it well, or gone to the right boutiques, because Mabel told me that she was so jealous of my clothes.

“My mother has no idea,” she said. “She has only one look – rich slut.” It was really very cruel, because her mother seemed nice. It was just that she was missing a man in her life, and that struck me as being sad.

Roop approved too. He said that my clothes reflected my personality – bright and yet sophisticated. It would have been nicer if I had really chosen them. But I started to wonder if it might be the other way around: Can wearing the clothes make the wearer bright and sophisticated? It certainly seemed that way.

I started playing around with my hair too. I tried braids and curls, ups and downs, and half ups, and one evening Grandma even arranged a French roll. Honestly, I never thought that a hairstyle could make me feel so different. It made me act differently, and Roop too. When he saw me that night, he kissed my hand and pulled out my chair for me.

He complimented me on my dress. Grandma had selected it for me. It was like I said – she had chosen clothes that were modern and suited to my age, but this was different. It was cut low in the front and it needed padding and some tape to create the hint of a cleavage.

“You are still a child and too young to be sexualized,” she said. But in this outfit, I felt sexy.

It was the formal dinner, so Roop was dressed up too. He looked like he had been born to wear a tuxedo. It must have seemed to the other passengers that we were just four pre-teens pretending to be adults, but we felt more grown up that night. Roop suggested that we drink berry juice from wine glasses with our dinner. It was great.

A dance followed. I danced with Nathan and Roop, but mainly with Roop.

“The voyage will soon be over,” he said. “And I am terrified that I will never see you again.”

Who says something like that? I had to kiss him. I just had to. because the truth is that I felt exactly the same way about him.

Cruises are supposed to be like that. Mabel’s mother complained about it that night. She had met a man but they would never see one another again. She told Mabel that she would not be in their cabin that night. We all understood what that meant. But it would end there. She had not found her man. It would just be a momentary pleasure.

But even that would be denied to Roop and me. This kiss would be all that we could ever hope for.

“Will you come and visit me in the summer?” he said. “My home is very big. In fact all my homes are.”

I was not even impressed by that. I hardly heard the words. I was just looking into his eyes and my heart was screaming: “Yes, yes, oh please, yes!”

“I am … I will disappoint you.” That is what I said.

“It would disappoint me if you said ‘No’.”

Whatever Grandma knew about me that I did not know, it became clear that night. It did not upset me later when she explained that she had been putting something in my tea to delay my puberty and give me the time and some maturity before I should choose my path. There was a fork in the road and I took the right fork. Veering left may have kept me on the seal, whereas the path to the right was winding and rocky, until it opened onto a beautiful avenue with cypress trees on either side, and a palace at the end.

Because I really met my prince on that cruise. Ruprecht Von … actually, the rest should remain private. We are much older now, but a very private couple. Ever since that time we met, we have taken a cruise every year, just to remember where our happiness began.

The End

© Maryanne Peters 2020

Author’s Note:
People may know that I post little things on Fictionmania inspired by images and captions I see, which I like to call "sketches" - exercises in the writing art. Some time ago I wrote one of these called “Granddaughter” about a grandchild taken on a cruise. I often receive reviews for these pieces and I always say that if something is worth extending I am up for that. There were plenty asking for it here and one reviewer suggested "have [her] meet an honest to God, royal prince". I was up for that too!