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Copyright Information : (c) 2001, by Sarah London. All rights reserved.
Interactive Versian available on http://www.geocities.com/sarahlondon2001

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This is a work of fiction. Any resemblance to any persons living or dead is pure coincidence. You should also be aware that this work contains adult themes and language. If you're not legally allowed to view such material then be warned. I have no further responsibility if you break the law.

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Email: sarahlondon@another.com    Web: http://www.geocities.com/sarahlondon2001

 

Summer Cruise          by: Sarah London                 sarahlondon@another.com

 

 

Chapter 1: A holiday about to begin

It was my first night in a new city. We had been travelling across the states for the last summer. We had arrived at our final destination, an amazing port city off the cost of Florida. I was travelling with my friends Tom, and David whom I had been a friend with since High School. As we drove along the waterfront, past all the marinas, we marvelled at all the huge yachts anchored by the dock. Occasionally we would wave at one of the glistening ladies sun bathing on top their boats. Every so often, much to our enjoyment, the bikini-clad beauties returned the wave.

Eventually after a long winding drive we arrived at a decent looking hotel. Once we arrived inside we realised how wrong we were. Inside the hotel wasn't great, in fact it was quite a dingy place with cockroaches in every corner of the room. I hung up some of my shirts and trousers and since I didn't have a lot of clean clothes left, I left the remainder in my bags. Just then Tom walked in.

"Unpacked?" he asked

"Yes" and ready for some sleep, I am exhausted" I replied

"We are going out later and tomorrow we have a busy day, we are going to meet my parents on the boat. They are arriving at the West Marina early, so they can spend the day with us."

That night we all went to a nightclub. I picked up a really hot girl, called Talia, she was perfect, she was beautiful, interesting and sexy. She had long blond hair, sparkly blue eyes and was really fun to chat to.

After making out in the club for a while, we decided to leave and go back to her place. As we were leaving tom grabbed me and joked that I mustn't go falling in love as they needed me to drive back tomorrow evening with them. Talia stayed in one of the main apartments on the waterfront, near the marina. It had an absolutely amazing view, from the balcony you could see out for miles across the ocean all the way to the twinkling lights of the huge ocean liners that sailed in and out of the city every day. She had a soft white couch on her balcony where we made out for ages, occasionally stopping to gaze out over the sea; it was impossible to be in a more romantic place We left the club and went back to her room where we made out on the couch for ages" I really like you a lot, " I said to Talia "its a pity that I have to go home tomorrow night"

"I am going home tomorrow afternoon with my friend on her yacht" she said" She has the whole yacht to herself, so it will be just us and the crew

"The crew," I said astounded "How big is the yacht?"

"3 decks" she said "Her father once had about 20 people staying on board when he had his birthday party"

"Wow, that sounds amazing," I said, "Why can't that sort of thing ever happen to me?"

"Why don't you come with?" she said, "there's plenty of room"

"I can't Tom's sister is getting married and we all have to be back home for the wedding," I said "Even though I am not crazy about her, Tom and David won't speak to me if I make them miss for her wedding""

"Pity, I would really love you to come with me," said Talia as she stroked my face.

We kissed for ages more before Talia led me into her bedroom where we made love and cuddled the whole night

In the morning after waking up and having breakfast, the conversation turned back to me leaving later on that day.

" I have been thinking about your offer last night, and I have decided that I would really like to come with you. Tom and David could probably manage without me, they will probably have to stop over an extra night without another driver in the car but they can manager. I am still not sure but to tell you the truth I am not crazy about going to this wedding.

"I would love you to stay with me" Talia said, "I am going to the yacht in a few hours, so you must make your choice quickly." She told me that her. I was stuck, I couldn't pass up such an amazing opportunity just to go to a wedding of a person I didn't like. How could I stay I thought to myself, Tom's parents were at the dock at the moment waiting to take me out on their boat and the way I thank them is to abandon their son and snub their daughter's wedding. Yet on the other hand, I looked at Talia who was wheeling her bags into the entrance hall, I could spend an extra few weeks with a gorgeous girl going around the Caribbean.

Just then Talia's mobile rang, she picked it up and said "Where are you?" She suddenly grabbed my hand and dragged me over to the balcony. She started waving frantically down to the marina. I looked down and saw a gorgeous bikini-clad girl in sunglasses waving back. She was standing on the front of one of the largest yachts in the marina. I thought to myself, for a few weeks on that yacht, I could miss a wedding. My eyes suddenly diverted to the boat moored next to it and I was horrified to realise that Tom's parents were sitting in the boat next to them. I pulled back from the balcony and run inside the apartment.

"What's wrong" said Talia

"The boat next door is owned by my friends parents" I replied, " I hope they didn't see me. How am I going to get on the boat? It would be such an affront if they were to see me get on another boat and deliberately snub them and the wedding, they wouldn't speak to me again." If I was to get on the boat, I could call them tomorrow and tell them that I was mugged or something and they took everything, anyway I can think up an excuse"

"Well we are due to leave in 15 minutes so make up your mind now are you coming or staying?"

"I am coming", but how am I going to get past Tom's parents, maybe if I wore sunglasses and a cap they wouldn't recognise me " Tania looked down at the boat and said" I think your friends have arrived, they are sitting down at the table next to Tom's parents"

I froze, there was no way that I could fool Tom or David, they could recognise me straight away.

"Well I am going to take my stuff down to the boat, she said as she wheeled her bags to the elevator." you think about how you are going to get onto the boat There was no way that they could see me, if they did I would miss out on this amazing opportunity to go on holiday with Talia. As for my clothes back at the hotel left and the Caribbean was so cheap anyway, that I could buy some clothes and toiletries tomorrow at one of the stores. I had my wallet in my pocket so it would be easy to stay with Talia, anything I needed I would buy.

Just then Talia walked back into the room. She was wearing a short white skirt, white flip-flops and a tight pink bikini top she had her glasses and hat on.

 

"I don't know what to do" I said, "How am I going to get to the boat without my friends seeing me? They are sitting opposite us right next to your friend's yacht".

That's not a problem" Talia said, "All you have to do is go in disguise!"

"What disguise?, I can't exactly go out and buy a monkey costume and anyway, if I walk outside this building I could be seen."

"I have a few ideas," Talia said with a grin on her face!

She pulled me into her room and opened up her cupboard. "We have to work quickly the yacht will be leaving soon," She opened up her cupboard and to my surprise pulled out a matching set made up of a black bra and panties.

"You can go as my girlfriend!" Talia said with a huge smile, "Your Friends are waiting for a guy in shorts to arrive not a girl in a skirt and high heels!"

I looked at the clothes and shook my head and said "but I don't look like a girl"

"Hurry up, otherwise I will have to leave without you, come and try this on and we will see how you look". I got undressed down to my boxer shorts. . Talia pulled out a pink skirt and a small backless top. I reluctantly stepped into the skirt. It was a strange sensation as the cold elastic material slid up my leg. I was trying to adjust it so that it would stay up when Talia came up behind me. She put her hand on my exposed shoulder just next to the top's strap and quickly pulled up the zip on my skirt.

I felt the skirt tighten. I adjusted the tight top while Talia fastened it behind me. While I was straightening out the top, Talia took my hand and started moving her manicured hands up and down my arms as we kissed.

As she moved her hands down to my chest, I began to feel really hot as the silky material rubbed on my chest.

"We need to do something about that chest of yours," said Talia "Come into the bathroom for a second" said Talia. I followed her in. She pulled out her razor and gently shaved all the exposed hair on my body, it wasn't a perfect job but from a distance my legs and body looked hairless. She turned me towards the mirror. I was shocked as I stood next to Talia and couldn't help posing. My body looked extremely feminine with the skirt on. From the waist down I looked almost like a girl.

By the time, I had finished posing, Talia had pulled out a pair of black high heeled sandals and had placed them on the floor in front of me. I stepped into the shoes and Talia helped me to fasten the straps. The feeling of standing in high heels was really awkward. It felt as though I was about to fall over forwards, when I walked forward my feet felt off balance, I had to steady myself, however the heels weren't that high so I soon regained my composure and was able to walk relatively normally. I stood next to Talia. From the neck down, I looked completely feminine, and quite attractive. Talia took my hand and started moving her manicured hands up and down my arms as we kissed.

"I can't wait, its going to be amazing, she said, "Let me do your makeup so we can get you onto that yacht"

"We don't have a lot of time," she said "I am going to give you my sunglasses to wear so all we will have to do is put some lipstick on you. She pulled out a tube of dark red lipstick and applied it to my lips, Its important that you look like you are wearing lipstick if they look at you."

"How do I look" I said as I posed in front of her. Just then she looked at her watch, "We're late, quickly" she said grabbing my hand. I was concentrating hard on not falling over as I ran in my heels. As we were going down in the elevator, Talia told me that I should walk next to her and try not to look at the boat with my friends on it. When we got down to the ground floor, I quickly began to cross the street and hurried on to the yacht

 

Chapter 2: The Journey Begins

As the boat gradually left dock, I was sitting downstairs. Talia came downstairs and said that it was clear. I went upstairs to see Candy standing there with an angry look on her face. "You strange pervert, I can't believe you came onto my boat dressed like that."

She turned to Talia and said "You know my father would freak out if he knew we had a boy on the boat with us. We don't have time to turn around otherwise we will be late for our docking place at the next port. We will leave you there. In the meantime you will have to stay like that and hope that the crew don't catch on. To them you must just be one of my girlfriends. Lets see we'll call you, Arabella, that's a nice girl name. "Talia giggled

Candy looked sternly at Talia and said" Talia, SHE's your responsibility"

"Don't call me "she"" I said irritated "there is no one else here, we don't have to pretend" Candy was shocked for a second, she grabbed my arm and said "listen honey while you are on my boat you will do as I say and be what I say otherwise one word and you will be dealt with by the crew who I am sure will be very angry that a bloke snuck on to the boat and besides you don't deserve to be a he. Real men don't go around in pink skirts and heels so come on Arabella dear, go make yourself look pretty. Talia help HER fix HERself up."

I felt terrible I ran out the room as fast as I could go. I ran into one of the bedrooms and began to rip the tight top off my body. I grabbed the hem of my skirt and tore it off my waist. I was tugging at my heels when Talia came into the room.

"What are you doing?"

I stood up and said that I was leaving. I just wanted my clothes back. Talia said that she didn't have them. She asked whether I had brought them back from the flat. I was stunned. Here I was stuck on a boat in the middle of nowhere without any male clothes. Talia said that I was too big for Candy's clothes to lend me something. Until she unpacked some more clothes, I would have to stay like that. I looked in the cupboard in the room to see if there were any clothes to wear. As I opened the cupboard, I saw that all there was hanging was a lilac one-piece woman's bathing suit. Talia pulled it out of the cupboard and held it up to my body. "You must be kidding"

"What else are you going to wear? You can't parade around the boat in boxer shorts. Come on James, since you are going to be one of the girls for the rest of the trip, you might as well stop fighting it. Try it on, you might like it. I know I do. " I snatched the costume away from her and stepped one leg into the lycra swimsuit. I put my leg into the swimsuit.

"It feels really tight on my one leg I think it's too small" I said with a sigh of relief. " No its not" Talia said as she took the costume and stretched the other leg hole open for me to step into. She then slowly raised it up my body until it fitted tightly below my waste. The soft material clung to my skin as I pulled it up my body. I put my arms into the straps and turned around to face Talia. The swimsuit felt tight as it clung to my body. The tight lilac costume also had the effect of feminising my curves. After Talia had convinced me to remove the remaining hair from my legs, and chest, Talia handed me a light pink wrap around skirt, which she wrapped around my waist. We sat down at the mirror.

She opened up her bag and said, "I am going to apply a little makeup to your eyes to feminize your looks". She applied some mascara to my eyelashes and a light shade of eye shadow to my lids. She finished off by making me apply a light pink shade of lipstick to my lips. Afterwards we both admired the look in the mirror. Both of us had bare shoulders except for the thin straps. Talia's swimsuit top was sticking out a lot more than mine due to the size of her chest and her smooth legs looked amazingly sexy. It suddenly struck me that when I looked down at my own legs, that to Talia I must have looked identical to her. Talia must have noticed that I was staring at my legs and she said "Don't worry sweetie, your legs look great, Candy and I would kill to have legs as sexy as yours,"

I looked at Talia who returned my gaze, we embraced for several minutes, when suddenly Candy knocked on the door and opened it. She looked a bit shocked, by what must have seemed to be two girls kissing, but she regained her composure and said "Quit playing around girls, lets go sun bathe on the front of the boat. We all picked up some towels on the way to the deck and after setting out our things; we all lay down and started sunbathing. As I was lying there, all thoughts and discomfort with what I was wearing seemed to fade away as I looked aroung and realised how beautiful the view was with the open sea and the blue sky. Suddenly my attention was drawn to the boat's front window. My eyes caught sight of one of the crew staring out of the window. I immediately sat up and pulled a towel on to cover myself.

"What's wrong?" said Candy

"One of the crew was staring at us"

Talia and Candy looked around but didn't see anyone. Candy said that if I felt disturbed by this then we would sunbathe on the upper deck. We all lay down again and continued sun bathing, I could see that Talia was getting turned on by my humiliation as occasionally she would gently move her fingers up and down my lycra swimsuit, and gently touch herself at the same time.

We spent the whole day out in the sun; eventually we decided to take a break to get something to eat. Candy said to us that there was a restaurant on a nearby island which the captain was stopping at.

 

Chapter 3: Out to dinner in a new dress

I protested but Candy said that I could easily pass for a girl; they will just have to help me get my mannerisms girly enough. We all went downstairs; into candy's room it was a large double bedroom with extremely ostentatious decor. She walked across to her cupboard and pulled out a shortish black dress. She then pulled out a pastel pink bra and pantyset. She started rustling the bottom of her cupboard and pulled out a pair of white sandals. I was hoping that I was going to see Candy getting changed; she was after all a really sexy looking girl. My hopes were dashed when she suddenly handed them to me and told me go get changed. She could see that I was about to protest but she put her finger over my lips and told me to keep quiet and pushed me towards the bathroom. I shut the door to the bathroom. I was really upset; I sat down and looked at myself. I was stunned when I looked down to see myself in a wrap skirt and a women's swimsuit. I then looked down and saw the heels, and dress and the effeminate underwear and thought to myself that if I would have left Talia, I could be at home now. I heard a knock on the door and a voice said hurry up Arabella, we all need t get changed. I quickly took off my clothes. I pulled on the panties and pulled on the halter neck bra and fastened the straps. I slipped on the dress, it was really short and only went down to just above my knees, and it felt a bit loose. I slid into the heels and fastened the straps, after admiring myself in the mirror; I opened the door and walked outside. Both girls were sitting on the bed with their legs crossed chatting. They both turned their heads when I walked in. Candy smiled and Talia said welcome to the girl club, with a grin on her face.

"Why don't you give us a twirl Arabella?" said Candy

I immediately gave a quick spin around which wasn't easy in my heels. Talia suddenly stood up and walked over to me and turned me around and said, "You haven't zipped yourself up2 She immediately grabbed the zip and zipped me up on my back. I hadn't even realised that there was a zip.

"I am still new at this" I said almost with a girlish giggle.

"Don't worry, you'll get used to it" said Candy as she started going through her cupboard. The dress I was wearing had suddenly become much tighter, I looked in the mirror and Saw that my curves were now looking much more feminine, in fact I looked a lot like a girl except that I wasn't wearing any makeup, that I could see. Talia grabbed my hand and sat .me down on the bed next to her.

"Cross your legs like this" she said and I did my best to copy her. "I want to do your nails and makeup so we can go get something to eat.

Candy walked into the bathroom to get changed while Talia opened up a bottle of purple nail polish and began to apply it to my nails. After a few minutes Candy emerged from the bathroom just as Talia had finished helping me with my makeup. Candy looked quite hot she was wearing a pair of blue denim shorts and a white strappy vest with a pink heart on it. She was wearing an identical pair of sandals to mine.

"Hurry up Talia, get changed so we can eat"

Talia walked out the room, leaving just Candy and me alone. Candy sat down next me and looked me in the eyes.

"James, you look just like a real girl"

 

Chapter 4: Girlfriends

She said that she had always fantasised about sleeping with a femboy as she called me. Just then I felt her hand touch my knee, I responded by immediately crossing my legs so that her hand was knocked off my knee. I immediately pulled the hem of my dress, in a vain attempt to cover more of my legs. Instead of being put off she moved closer to me so that she was sitting right next to me. She gently put her hand on the inside of my leg and started moving it up my leg.

"You see Arabella, you are already acting like a girl, here you are sitting with your legs crossed, and the way you adjusted your dress, almost was like you have been wearing dresses your whole life. Have you ever worn feminine attire before?

I shook my head, but suddenly caught my breath as I realised that Candy had put her hand all the way under my skirt. Just then we heard footsteps coming down the corridor and Candy pulled away and crossed her legs.The door suddenly opened up and Talia walked into the room. She was wearing a pair of cropped black trousers and a blue strappy vest, and sandals. Talia smiled and exclaimed wow that's what I didn't expect to see, two girls sitting cross-legged on the bed. Just think, James, this morning, did you think that you would be one of those girls?" Said Talia

"And did you think that of all the girls in the room, you would be the only one in a dress?" I just blushed as we all left the boat and took a launch down to the restaurant. We sat in the corner of the restaurant and had a great meal. I was convinced that we were getting looks from the boys sitting at the other tables. I must admit when I gazed at girls at the other table, they returned back frowns. As though they were jealous at the attention we were getting. Candy, Talia and I spent the time chatting; occasionally Talia would giggle when she looked at me. Eventually the subject turned to suntans. We were all comparing suntans when candy took the strap of my dress and pulled it off my shoulder. "You have really bad strap marks, maybe tomorrow you should wear a bikini so that you get a better sun tan," Candy laughed.

After lunch we went back to the boat and went back down to the room. Talia said "look at the time, we can still catch some sun before the sun goes down. Lets get into bikinis and go and sun bathe on the upper deck. So no one will look at us. I was just about to go with Talia when candy said stay with me. Talia said ok and that she would meet us on the upper deck.

Just as she left the room candy closed and locked the door.

"I am shutting the door for some privacy, I am going to get changed why don't you pick yourself out a bikini and a skirt to wear with it"

Just as she went in, I stood up and went over to her telephone. I called Tom's parents just to say that I was ok. Little did they know I was sitting on the bed, legs crossed in a dress and makeup and shortly I would be putting on a bikini to go sunbathing? Just then Candy walked in

"What are you doing?" I immediately hung up the phone. "Since I can't trust you will get changed here, in front of me" She walked over her cupboard and pulled out a pink bikini. She turned around and said "strip, I want you

wearing nothing except your nail polish, you don't have to be shy, we are all girls here. " She said with a glint in her eye. After I had finished getting undressed. Candy held out the bikini bottoms for me to step into. A shiver went down my spine as the soft Lycra bikini briefs slid up my shaved legs. Candy took the bikini top, and put it onto my chest she put her arms around me and fastened the straps behind my back. As she did this she rubbed her semi naked body up and down on mine. She turned me around and fastened the halter neck behind my neck. As she walked around me admiring her work, she said "wow you look really great in that bikini Arabella, I think I will give it to you, Let me look at you in your little bikini"

Candy suddenly couldn't resist and started to embrace me, we kissed for what seemed like ages.

"Talia will probably be getting suspicious, we had better go up to the deck" Candy said as she threw me a pair of tiny denim shorts. I slipped them on and pulled on the tight white shirt that Candy handed me. Even though these could be called unisex, when I looked in the mirror and saw an image that looked more feminine. I don't know what made it look so feminine, whether it was the long shaved legs or the fact that you could see my pink bikini top through the shirt, or even my makeup and painted nails.

I put on a pair of sunglasses that Candi gave me. We walked up to the main deck and sun bathed until the sun went down. Candi and Talia were whispering to each other the whole time while we were sunbathing. I couldn't hear what they were saying but I was so relaxed that I didn't care much. Eventually as the sun went down, we all got up and went down to eat. Candy disappeared for a while, but when she came back she said that we would be stopping at an island nearby where there was a really great bar, with a great atmosphere. Talia said that she was staying on the boat. I thought that she was upset with me kissing Candy.

I went down to Candy's room to find that Candy already had a dress laid out on the bed for me. I was just slipping it on when Candy walked in. She and I fixed up our makeup, slipped on a pair of heels and took the small boat out to the bar.

We laughed, drunk and flirted with each other for the whole night. It was really embarrassing because Candy was taking the lead all the time. It was her who bought the drinks, it was her who gently held my side and it was her who was paying me all the complements

"You look really cute in that dress Arabella"

"Thanks, Candy" I said almost automatically responding to the name Arabella.

The next thing that happened was we were kissing again, more passionately than before. "You are so hot," said Candy in between kisses "I would love to take you back to my boat and make love to you. Do you want to come back?"

"Yes" I said almost shuddering with excitement.

"Great you can dress up all sexily, for me"

 

Chapter 5: A sexy surprise

Eventually we arrived back at the room, I opened the door to the bedroom to see Talia lying on the bed in lingerie, stockings and heels. She sat up and smiled when we walked in she walked over to Candy and kissed her on the lips and then walked up to me she held my hand and stated kissing me on the lips. I could feel her nylons rubbing on my shaven legs I could taste our lipsticks intertwining.

Talia pulled back, and looked at Candy. Candy nodded to Talia and said to me that I had experienced a lot as a girl but now I was going to take it to the next level.

I stared in disbelief as Talia dangled a sexy pastel purple bustier in front of me and said that it was for me.

"I am going dress you up so sexily for Candy and me. In lingerie, heels and makeup like me. " said Talia.

I looked at Talia and immediately thought to myself that I had always dreamt of having a girl in lingerie undress me, but I never though that I would be the one to be adjusting the stockings on my leg and wondering if my mascara was running.

Talia looked at me and said" hurry up and get undressed, and don't give me any of that stuff about you being a boy; you don't look like a boy standing on those high heels and in that dress."

I dropped my head almost embarrassed and started to unzip my dress. The dress fell to the floor leaving me in my bikini. I took it off and stepped into the g-string that Talia was holding out for me. I slipped on the bustier and then sat down and pulled the nylon stockings up my legs. And attached the straps. I slipped on the high heels that were waiting next tot the bed. I looked at Talia and smiled at me and said, "You look so feminine that you could be one of the girls"

 

We sat down at the mirror and we did our makeup. Talia made sure that my makeup looked as sexy as they way I was dressed. She used lots of pinks and purples and blended them all in so I looked really sexy. I was feeling and I looked really sexy, I picked up a bottle of Candy's perfume and sprayed it onto my chest. We both stood up and looked at each other. We hugged, I looked down and saw two sexily clad bodies and found it hard to believe that one of them was mine.

Talia suddenly pulled back and exclaimed,"You are completely feminine now, James, you are wearing nothing that a male would wear. You even smell feminine."

Just then Candy walked in, dressed in trousers and a collared shirt. Candy was pretending to be a guy! She still looked like a girl, but Talia and I played along. We both looked at each other and walked daintily up to Candy who grabbed us both around the waists; she even put her hand onto my bum, which was now exposed thanks to the g-string. I wrapped my leg around Candi's as Talia had done to me. Talia eventually pulled back. I sat on Candi's lap on the sofa and let her run her hands up and down my nylon-clad legs. The night carried on like this eventually we were exhausted Talia handed me a sexy silk nightdress to sleep in.

When I woke up in the morning the girls had left and had left me a note saying thanks for last night. We will always remember Arabella, I hope you will too. Next to the note I saw my clothes and wallet that had been left in Miami. The clothes had been washed and folded. Next to them were a fresh bra and panties as well as the dress I had worn last night. It was as though they had left me a choice whether to go dressed as a boy or girl. I was unsure for a moment, when I thought how I felt so comfortable in the dress yesterday and how sexy I felt in the lingerie. I though to myself that instead of choosing one, I could have the best of both worlds so I slipped on the bra and panties and then pulled on my clothes, stood up and walked off the boat, to find my way home.

 

(c) 2000/2001 Sarah London
sarahlondon@another.com
Interactive Versian available on http://www.geocities.com/sarahlondon2001

 

 

© 2001
The above work is copyrighted material. Anyone wishing to copy, archive, or re-post this story must contact the author for permission.