Stranded on Tranny Island
Copyright© 2026 by storyace
Chapter 3
Erotica Sex Story: Chapter 3 - Captain Fred's boat 'Sweet Christine' is damaged and gets towed into a nearby Philippine island. With his pregnant bunk mate 8 months along, they have to stay. Fred ends up getting stuck on the island of tanssexuals, in more ways than one.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Shemale TransGender Fiction Interracial White Male Oriental Female Anal Sex First Oral Sex Pregnancy
When I woke up the next morning, there were two very attractive ladies cleaning in the kitchen with Heath, who was already eating his breakfast.
I knew them both; one was a nurse, the other a technician at the hospital. They looked different now though; they both had their hair down, wore tight short dresses, and makeup.
“Uh, good morning.” I said as fresh croissants and coffee were placed on the table.
“We want to be your girls.” The nurse informed me as I tried to remember her name.
They both smiled at me anxiously.
“Not for money.” The other one, Henrieta, added. “We both have jobs.”
“What do you want then?” I asked.
“We want to serve.” The nurse told me.
“We cook, clean, care for the boy, wash clothes,” Henrieta added, “And ... we...” her big dark eyes rolled sideways and we all laughed, which was great.
They were nice, and good looking, and the coffee was good, and I was very horny.
I looked at my boy, who had been washed, dressed, and fed. Oh man, was I being offered free tranny threesomes every night?
“I have to take Heath to school.” I told them.
It was a half hour walk down with the boy, and 20 minutes back. I knew the two applicants slightly. I sure could use a good blowjob; what about Leonie though? Should I reject two sexy eager girls for the possibility of one who was way out of my league?
More importantly, I needed the help that the two ladyboys offered. I was just starting the biggest project of my life, cash was short, I’d taken on several solar power installation contracts that I had to finish up too.
I didn’t have time for a relationship with demanding Leonie.
I went to her club. The door was open and there were people inside cleaning up. I went through and upstairs to her apartment. I knew where it was, even though I’d never been in there.
Leonie’s grin was what I saw first; then I saw the man on his knees at her feet, hands tied behind his back. He was wearing a dog collar, complete with a lead, which Leonie was pulling on. In her other hand was a riding crop, which was not for horses as there were none on the island.
She sat on a divan, her immensely long legs adorned with mesh stockings spread wide. Her hair was tightly pulled back, and she wore a bustier / corset.
The man eagerly sucking on her cock was the governor, my landlord and boss, Barry.
She saw me and her face dropped. Her slanted eyes went round, which was sort of funny.
I backed out the door, back downstairs and walked towards home, feeling oddly lighter.
I’d been conflicted. Leonie was a force of nature, her sexuality too powerful to resist. She was not at all what Heath and I needed; she was a hurricane, her powerful beauty simply too intense for survival. And she’d seduced me, and it had been fantastic. And she wanted to dominate me, and I would have happily let her.
Now though, after that one glimpse of her with Barry, I was free of her. There was no betrayal. She’d made no promises, no declarations. I felt hugely relieved; I’d been terrified of Leonie, and now I wasn’t.
As I started up the hill, I looked up and saw the two dark heads of Henrietta and Leh looking down at me from my balcony.
They seemed good; just what I needed, especially now that I was about to have so much work outside the house. Cash was going to be tight for a while; what did they really want?
I got to the house sweaty and slightly out of breath. The two transexual women stood silently on the balcony, and it was awkward. We had no common ground yet; I didn’t know what to say, and neither did they.
I looked them up and down silently in the cool shade of the bright morning. Leh was a feminine girly ladyboy; makeup, long hair, colorful dress, slim waist, medium breasts (apparently), and 2” heels. She was small, only as high as my nose. Delicate, vulnerable.
Henrieta was more androgynous. Her face was not as feminine as Leh, yet you still wouldn’t categorize her as male. Her hair was practical-short, cut off just below the ears. She wore no makeup, and looked good anyway. She had similar breasts, and wore bright yellow cotton trousers and a matching T-shirt.
I dropped into a chair as we all considered the situation for a long minute of silence.
“I have to think about this.” I told them, and went to have a shower. I noticed that the bathroom was clean; even the grout between the tiles was gleaming white. I’d never managed to achieve that myself. I was impressed; that showed determination.
There were only small towels though; they’d taken my big bath towel away. I dried myself and went out to find the two ladyboys had come inside and were now standing on either side of my bed, like sentries. And their four eyes were all focused on my cock.
They were perfect.
Beautiful, hard working, willing, and waiting for orders. How could I refuse them? How could I accept them?
It felt like a betrayal to take these two. They were what Heath and I needed though; Leonie was not.
“Ok, look, you girls are wonderful.” I told them, and their faces lit up like light bulbs, “You’re both beautiful, I can see you cleaned and cooked already, I just need to know what you want from me?”
They looked at each other uncomfortably, then at me again. Slowly, Henrieta’s hand rose, forefinger extended. She pointed at my soft dangling dick.
“That’s all?” I asked.
They both nodded, as if mute.
“We need a man.” Henrieta said softly, her eyes pointing at the corner of the room. “We know you’re a good man. We’re good ladyboys, we’ll do everything.”
She seemed to run out of words for a moment. Then she asked; “Tell us what you want, just tell us, we want to ... serve. We want you to ... be...”
“Yes, go on, say it. You want me to be what?” I insisted.
“Our master.” The cute ladyboy choked, yet her eyes locked on me again. Leh nodded, standing still and silent.
“Why?” I asked. “You both have jobs. You don’t need me.”
“Yes, we do.” Henrieta insisted, as Leh nodded silent agreement. “We had a man before, a good man, we served him and we were happy. Now we have no man. Let us be your girls, we make you happy, we will cook and clean and, and ... do what men need.”
She was staring at my cock again, and it shifted as I looked at her cute little face, which made her smile, which made me horny.
I sat on the bed, upright against the headboard with my legs stretched out. The dynamic was interesting; they were still dressed. I had no idea what they even had under their clothes. I was vulnerable, naked, exposed. At the same time, I was the power. I had to make the choice; accept two young pretty ladyboys who were begging to serve me, or ... what? Why was I even hesitating?
“Ok.” I said, waving my hand over my groin, “Go on.”
Sexy Leh crawled onto the bed and dropped her face over my rod without a word, moaning in pleasure as Henrieta watched with delight and triumph on her face.
My cock was rock hard in a second; the girl sucked eagerly, her beautiful smooth silky black hair flowing as her head bobbed up and down my cock, the sensation simply exquisite as I throbbed with powerful pleasure in her eager mouth.
I should stop questioning good luck, and just accept it.
I saw Leonie on the veranda, looking in through the window; I pretended I hadn’t, and looked at Henrieta, stretching out my hand. She brought her face to my palm, and I looked into her soft eyes as Leh eagerly pleasured my cock. My heart seemed to contract; I could love them.
Leonie was vanquished. Yes, she was more sexy than Leh and Henrieta combined. She was not what I needed though. Could these two really want to clean my house, cook, shop, look after Heath, and all they asked was to share my bed?
My erection throbbed at full power as I looked into Leh’s pretty face. It felt wonderful, yet it wasn’t right. I pulled back, and she crawled forward to keep her mouth on me, sucking desperately on my stiff rod until I pulled it from her.
She looked at me blankly and sat back on her heels.
“Ok, listen.” I told them as I sat on my bed, “You girls are fabulous, but let’s slow it down a little and talk for a while.”
“We talk later, now I have to go to work.” Henrietta said, standing up in her cute yellow outfit.
Leh sat next to me as Henrietta left the house.
“You both know my story, I want to know yours.” I told her as she looked at my stiff wet rod hungrily.
Her story came out in confusing, hesitant pieces. She didn’t want to talk about herself until I insisted. She put her pretty little head on my shoulder and I let her hold my stiff rod in her small hand as she told her tale.
She was from a small village a couple of miles inland on one of the larger islands.
“My family was poor, my father would drink and my mother did any work she could get. Some of the boys at school would go to the coast where the tourists were, and dress up like girls, and suck cock for money. The real girls never did that! Haha. Anyway, I started doing it too, and I liked it. I liked the excitement, and the money, and the way it made me feel when I did it. And the white men, they were all so big and rich.
It was wonderful; I was good at it, and I liked it, and they paid me money.
I brought the money home to my family, and I thought it would solve our problems. Instead, my father gambled and drank it all, and he demanded I bring more money, and still more. I stopped going to school and went to the tourist beach every night and suck more cock.
It was never enough; my father beat my mother and I, and one day when he owed too much money, he sold me to a brothel.
I’d never done it, you know, all the way. I was ready though, I was willing. I knew I had nothing else of value. My first time was with an old man from Japan. He was very gentle, and had a small cock, and it was nice.
I know that sounds terrible, but it was a better there than at home. At the brothel, I was valuable property, and treated well. The boss made sure I was well dressed and happy. He said a happy whore is a good whore. He promised that when my debt was paid, I could keep half my earnings. Until then, I had to have sex with men in the night, and work in the kitchen in the day.
My boss said I should get my testes out, because I was still a girly looking ladyboy and even my voice was still high pitched. He told me if I didn’t agree, my body would change and I’d become ugly. Asking for my permission was just pretense, I had to do what he wanted. He owned me. He said someday, if I worked hard enough, I could get surgery and get a pussy, and if I still looked like a girl I’d have five customers a night. He seemed to think that would be a good thing.
I liked the sex at first. Especially kissing and touching, I always like that. A lot of the ladyboys wouldn’t do kissing at all. I liked it, and so did the tourist men. I was popular, and earned very well because I enjoyed the physical part. After a while, I wanted more, and I had feelings for a customer, an Australian. He was SO nice to me, just he way he spoke, and I told him if he would buy out my contract, I’d serve him day and night. He did buy me, but then he told me that he was married and had children, and I was free. How could I be free though? I was a whore ladyboy with no family. I’d been protected at the brothel, because I was the property of a powerful man.
I got work in a restaurant, and I was confused. The work was like a holiday after the abuse in the brothel. I was afraid though; everyone knew what I was. Men looked at me like they wanted to kill me or fuck me or both. Women ignored me.
Then I saw Henrietta with her Swede, Olaf. He was big and grey, she was holding his hand and looked so happy, like sunlight came from her face. We talked on the beach as he went surfing, and she said I could be their housekeeper. He’d rented a big house and was living on the island all year.
I was very happy there, because Olaf was big and rich, I was safe. I cooked and cleaned, and I enjoyed the work. It felt good to serve him, he’d look at me with his foreign blue eyes and smile, and I loved him before I ever slept with him.
I was like a virgin the first time I did it for love. My body made the same feelings, yet my mind exploded with joy when he ejaculated in my mouth, looking into my eyes so lovingly.
Olaf would go surfing while I cleaned and cooked and washed his clothes, and when he came home I sucked his cock before dinner, and he’d make love with me deep in the night. I was content; but Olaf insisted that I should study to be a nurse, because that was one of the only good jobs for ladyboys. He said one day he would be old and sick, and I could care for him. Anyway, I did whatever he told me to do. If he said I should study and qualify as a nurse, I did.
A few years later, Henrieta and I were both 22. I was a registered nurse, Henrieta was a medical technician, because she’s so smart. Only no one would hire her because she was a ladyboy.
Olaf didn’t like it there, the beaches were too crowded he said. And then we heard about this island, with the ladyboy hospital. Olaf found a beach on the other side of the island with good surf, and we came to live here. Henrieta got a job at the hospital.
I found a big rash on Olaf’s shoulder. It was too late, it was malignant melanoma and he went home to Sweden for treatment, and never came back. We waited for him, the sea looked baren and empty without him in it. Last year, he stopped answering his phone.
I started working when he went away. I just needed something to do, and actually I like it. And also, now it’s time for my shift.”
The cute little ladyboy released my cock and got out of bed. I watched her as she brushed her long hair, tied it up into a bun, put on a simple dress and flat shoes. She spun to look back at me; she was totally feminine. Even plainly dressed and without makeup, Leh was a sexy young woman.
She gave me a little kiss before she left.
I watched her walking down the hill path to the village. She wanted to serve me; all I had to do was agree.
Henrieta came back before sunset, as I was about to start dinner. She was wearing worker’s coveralls, yet somehow she looked great in them.
“Leh told me you only talked all morning.” She said, “Can I cook for you? Please, I want to. Cooking is woman’s work.”
“That’s not true for me.” I told her, “On my boat, everyone has a galley day.”
“Well, this isn’t a boat, is it?” she argued, pushing me aside, even though she was half my weight. “If you let Leh and I live with you, we’ll be doing the cooking and cleaning.” She informed me. “It’s important for us to perform the traditional female roles. It helps us feel the way we want to feel.”
Unlike Leh, Henrieta had no hesitation about telling me her story.
“When I was 14, I knew I was a girl inside. I had two older brothers and no sisters. My father had a small transport business, we were middle class. A nice house, a cleaning woman, and a cook.