Stranded on Tranny Island
Copyright© 2026 by storyace
Chapter 4
Erotica Sex Story: Chapter 4 - 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
The mud, rock, and sand from the river bottom was dumped on my marshy field, raising the level about a meter. The locals watched in awe as the JCB loader pushed hundreds of tons of material into a wide flat surface, and placed the 2000 cast concrete slabs over it. A row of huge steel interlocking profiles was driven into the mud at the water’s edge, creating an almost instant deep water mooring that would last around 20 years. It was up to me to dig out a trench on the inside and build a permanent concrete quay before the steel rotted away.
My big rolling crane was assembled, a few containers of material and tools dropped too. The water rat boys were amazing; they worked 10 hours and seemed to get 20 hours of job done, then went to town and partied at Leonie’s club, the took their new ladyboy girlfriends to bed.
That was about the time my work had to start; setting up the port had 1000 details to fix. So it sure was great to have my energetic young ladyboys looking after the house, Heath, and myself.
Mornings they would alternate; one of them would get up to make coffee, breakfast, and get Heath ready for school as the other cuddled in bed with me.
Leh would kiss and stroke me, she just loved to make my cock hard. I didn’t like to ejaculate in the morning, I liked the energy I got from keeping it in. Just cuddling, kissing, holding her lean smooth little body and enjoying her boundless adoration was what got my day started.
If Henrieta was in bed with me, we talked. She wanted to know everything about everything, and she already knew most things.
In the evenings, after dinner, there was sex. Henrieta wanted it up her cute round ass on her nights, Leh liked to kiss and fondle, then suck me off. We rarely had threesomes; it was too complicated.
A few months after they moved in with me, Leonie brought Leh and Henrieta’s missing Swede Olaf up to the house, he’d just arrived and was looking for “his” girls. A strong young guy carried his bags.
He was dying. He looked terrible, razor thin with haunted sunken eyes, blotched skin, and no hair.
“My phone and my laptop were stolen from my hospital room.” He told us. “I just had to come back and see my girls again before I die.”
He hugged them, and the love was almost palpable. The three of them went in and talked as I stood on the balcony with Leonie watching the sunset.
“Sorry, he showed up looking for them.” She told me.
“It’s ok.” I said. “He hasn’t got much time left.”
Henrieta slipped out of the bedroom and came out to join us. She was a tiny thing compared to Leonie; I was wasn’t sure how they felt about each other.
“I have to go to work.” Leonie said, and was gone with a twirl of her long skirt.
“He’s asleep.” Henrieta told me, then stood silently.
“He needs you and Leh to take care of him.” I said after a minute.
“Yes.” She agreed, “But we are with you and Heath now.”
“I know you both still love him.” I said gently, “You want to love me that way, and maybe in a few months you could.”
“Do you love us, Fred?” she asked me quietly.
“Of course I do.” I answered, “You and Leh are perfect; but I know you have to take care of Olaf.”
“Will you go with Leonie?” She asked neutrally. “Because if you go with Leonie, Leh and I can be with Olaf.”
“I don’t know.” I said, “Anyway, you don’t owe me anything. You and Leh are wonderful, precious, and free to choose your own lives. I tell you though; I’ll always be your friend. And if I have a job, so do you.”
I went down to the growing town with Leonie, leaving Leh, Olaf, and Henrieta with Heath.
I sat in her club as she played music from behind a mixing board while dancing a little. She looked fabulous; her great hair swinging around her face as she towered above us all in her high heeled boots, impossible long legs in net stockings and a skirt so short that from time to time, I thought I saw the tip of her cock under the hem.
The place was packed with white tourist men and sexy ladyboys. Most were already paired up, some were hunting partners. These were ‘girlfriend’ candidates; they’d go with a guy for the duration of his stay, and pretend that it was about a relationship with longer possibilities; that they might get married and taken away from here. And it had actually happened a few times too.
I recognized a few of the girls; one who worked in the grocery shop, another who did hair, one who sold fish down at the pier. I wasn’t even sure of the last one’s gender.
It was a bit fishy.
There was one white woman, and we talked a bit. I was amused to see Leonie looked jealous.
At 1AM, the town generator was shut down for the night, which meant the powerful air-conditioner in the club went off, and it was closing time. The men all shuffled back to their hotel rooms and cottages with their dates. The white woman I’d been talking to slipped away too, and Leonie sat with me in the battery powered light as her girls cleaned up.
“We need to talk.” She told me, spearing me wither vicious sexy stare. “Come upstairs.”
I followed her tight round ass up the narrow steps to her boudoir, which was air-conditioned through the night by a battery system we’d installed recently.
She was wearing a corset on top of her shirt, and she left it on as she took off her skirt, boots, and stockings. She sat against the headboard of her oversize bed and spread her luscious legs wide. I didn’t want to get beck into bed with Leonie. Sure, she was the sexiest person in the world, she was also oversexed and crushed hearts like they were eggs for breakfast.
She looked at me and smiled; I couldn’t resist that, and she knew it too. “Leh and Henrieta are good girls, they’ve served you faithfully for months. They were with Olaf for years though, and now they’re in bed with him. Did you see how they looked at him? He’s a walking corpse, and they still love him. It’s so sweet. Suck my cock.” She added casually, “While I tell you what’s really going on.”
I had that hot sausage on my mouth before I could form another thought. I looked up at her beautiful smiling face, her perfect skin stretched over those high cheekbones, her white even teeth, her glistening dark evil sexy eyes as her stiff hot penis filled my head with weird hot pleasure.
I knew she was dangerous; I couldn’t resist sex with her that night, she was going to do me and that was a given. I just had to remember what and who she was, and hold my emotions tight.
“Oh yeah, that’s good baby.” She sighed as she held my head in her spider fingers and her rod throbbed with evil irresistible power in my mouth.
“My family used to run the country. Even now, my cousins, aunts, and uncles are generals, politicians, and judges. If power flips in the general election next month, we’ll be in power again. I was sent to the US for schooling, then I went to law school in Manila before I joined the police force. Here, look at this.”
She stretched one arm across the room and pulled a photo out of a drawer to show me. It was her, yet it wasn’t. A tall handsome young man in a police uniform with an officer’s cap, standing a head taller than a smiling grey haired man wearing a lot of medals and such.
“I was captain Leon Silva, that’s my uncle, head of the national police.” She told me. “I got into a little trouble when I had an affair with a diplomat’s son, he was underage and they got all upset. Uncle said I should come to the island and get a handle on the place. I decided to transition; not all the way. I thought I’d do the transexual thing for a year, make my big case, and then reverse back.
“It turns out that the ministry doesn’t want a case; they just want me to report the numbers, so they can check that they’re getting their agreed cut. And something else happened that I never expected; I like being this way. It’s a kick; I’m attractive to men, even straight men can’t keep their eyes off of me.”
I sucked on her hard rod as I listened in fascination; I was sucking cop cock? Her wonderful legs wrapped around me as I wondered who it was she was infatuated with.
“You stay here for the boy.” She said, writhing and thrusting a little as she stared into my eyes, “You pay your workers honest wages and treat them well. And you’re so damn good looking.”
I want numb with fear; she was making her play, she’d decided,
I kept my face in her groin and tried to get her rod down my throat, so I wouldn’t reveal my horror, terror, and delight.
She was half my age and twice my worth. It would never last; and when her emotions for me evaporated into the clouds they’d come from, I’d be in big trouble.
“Don’t say anything, just keep sucking my dick.” She told me, running her long fingers through my thinning hair as she looked down into my eyes while pushing her stiff rod deeper into my face. “Yeah, love; it’s bullshit, yet it’s the only thing that’s real. Let’s not talk about it, ok?”
She pulled her penis out of my mouth, and for a while we cuddled and kissed in silence; she stroked my stiff cock with her fingertips, and then in the quiet darkness of the tropical island night, we slept.
I woke in her arms; her long limbs encircled me like a sea serpent from an old saga. She was still asleep, and dreaming. Her body twitched a couple of times and her fingers clutched on my arms.
I’d been stumbling along without a plan for years. Sailing wherever the wind wanted me to go, sleeping with whoever wanted to share my bunk, I washed up on this island, stranded, shipwrecked, castaway, exiled in paradise.
I’d never gone to meet the child I’d made with Heather, instead I loved the boy who was not my child. Why? Because I had to, there was no one else for either of us.
Then the parade of transexual women who had been my friends and my lovers; each one totally different to the others. There was no generalizing possible. Like the rest of humanity, everyone was different.
Some were really women with cocks; some, like Leonie, had no particular gender identity. What was this need to categorize everyone? Race, nationality, social economic standing, age, gender, beauty. We humans put everyone and everything into imaginary boxes, labeled them, and then tried to keep them there.
Leonie was not a committed transexual. She was dabbling with it, experimenting, tasting the joy of femininity without surrendering the power of masculinity.
What if I had an affair with this long gorgeous sexy powerful person, and then she turned back into a he?
I could love her; shit, maybe I already did. Maybe I was fucked. Maybe I wanted to be fucked, because it sure felt good when she did that.
I untangled myself (physically at least) and went home to get there before Heath woke up.
I looked in through the door of my bedroom; Olaf, Leh, and Henrieta were tangled up in each other, sleeping like a litter of contented puppies. I had to stare for a few seconds; their black hair and perfect young skin, wrapped tightly around his blemished old damaged body.
There was something desperate about them; trying to recapture the happiness they’d once known. The love was still there, hovering between the three of them like a mist that could almost be seen by the naked eye.
I had work; an appointment on the other end of the island to plan and price out a solar power installation for a 4 room hotel.
There was some competition now; a crew from a nearby island had turned up and was making low offers. I had to be better than them; that meant being on time.
Henrieta appeared like a beautiful elf in her cute pink coveralls, and I sat on the back of her little motorbike as she rode us along the road that ran the length of the southern shore. The first half had been paved with hot tar and gravel; we passed where the road crew was still at it, and the second half of our journey was a rutted dirt track We went so slowly that we could talk.
“Will you and Leh stay with Olaf now?” I asked her, holding her tightly as we bumped along.
“I think so.” She said. “I’m sorry Fred. We were sure he’d died when we came to live with you.”
“You still love him?” I asked gently.
“We LOVE him.” She sighed. “We love you too, and Heath of course, you just have to understand, we lived with Olaf for 10 years. He gave us our educations, he taught us, he fed us, he ... well, you know. So now he needs us, and we have to care for him, love him to the end. We need to give him that, we want to give him that.”
“I understand.” I said, feeling sympathy for their pain and admiration for their loyalty. “Will you still work with me?”
“Of course! I like the work.” She said. “Will you go with Leonie?”
“I guess so.” I said, “She’s ... sort of impossible to refuse.”
Henrieta laughed hard, her strong little body jiggling in my arms. “We know you’re hot for her, and she has eyes for you too. I hope you’ll go with her, because then Leh and me will feel ok, you know?”
She and Leh; there seemed to be no reality where they were separated. That was when I realized that they might love Heath and I, they surely loved the big dying Swede, but they loved each other with a depth and totality that the rest of us could never match.
Henrieta made notes and said nothing as I talked to the customer. There was no regular power supply out here at all, people ran their own generators and battery banks. Many had PV systems already; mostly small setups. With the increasing tourist trade as well as increasing resident population, the demand for power was huge. And the prices of PV setups were dropping at the same time. I sold the hotel owner on a good system for a good price.
We bumped back along the road, I held her tightly. She was a good person, clever, hard working, and sexy. I’d miss fucking her cute round ass; at least I got to keep her as a friend and colleague. In reality, there were a thousand ladyboy asses on the island I could fuck. And very few, if any, other competent technicians.
When we got back to the house, Leh was in the kitchen, and Leonie was sitting out on the veranda talking to Olaf. Heath was at school.
“I know a house for rent on the other side of the town.” Leonie told us, “We’re going to go have a look, and I can bring Heath home afterwards.”
I watched Olaf shuffle slowly down the track; he had been a surfer, a proud and strong man. Now he was like this; barely able to walk.
I talked shop with Henrieta. We had 4 jobs scheduled and paid in advance, and 12 more wanted estimates.
“The other guys are selling cheaper.” She noted. “They use flimsy mounting hardware.”
“Yeah, wait until the next good storm.” I said sorrowfully.
We built systems as if they were on boats; because the island climate was the same. Salt, wind, and occasional heavy weather. We soldered cable lugs, built massive framing and used stainless steel fasteners. It cost a little bit more to do it right.
“I’m going to be busy full time at the marina soon.” I told my cute sexy and very competent assistant. “We need to hire some more help. Can you get on that?”
“Sure thing boss.” She answered, and I knew she’d take care of it, and I thought no more about it.
I went to Leonie’s for the night again. Olaf and the girls would move into their new place the next day.
I didn’t like the music, or the club, or the tawdry coupling of the island ladyboys with tourists. I was a creature of the day; of sun, wind, and fresh salty air.
Leonie was the opposite. She ruled the night, her business boomed and stank of alcohol, the hopeless hopes of the poor transexual Asian girls who gave their asses and dreams to transient men who used them and made promises everyone knew would not be kept, and dumped them 98% of the time.
Everyone was lying. The men and the ladyboys tried to feel more than they did, pretending that it was more than money and sex. And sometimes it was; there were men like Olaf. And like me I guess. We were rare though, literally one in a thousand.
The generator went down, the airco went off, and the room heated up quickly. A dancing person will emit 500 to 1000 watts of heat; and there were 30 of them in the closed room.
Once more, my face followed her towering legs and lovely young ass up the steep stairs to the waiting bed.
I sat down and watched in awed silence as she slowly stripped while facing me. piece by piece, her soft coverings were removed from her long thin body. She wiggled just a little, twisting and stretching seductively, even though we both knew I was already seduced.
Her big breasts fell forward, she shook out her great hair, smiled with her sexy mouth, and pushed her skirt down her miles of leg so her cock stood up between her net stockings.
Yes, she was gorgeous; the world’s longest legs, a perfect ass, and a stiff cock. It was her smile that made her impossible to refuse though. Her bright happy delighted grin, her girly giggle as she waved her rod in my face with a little twist of her hips.
“I’ve always been a top.” She said softly, clutching me as we lay down together. “I fucked women, men, boys, and ladyboys. Yet with you, I feel weird, afraid, vulnerable. You could hurt me. At the same time, knowing that we’ll be together is like a weight has been lifted from my heart. You know I’ll never serve you like Leh and Henrieta.”
“I know.” I conceded. “God damn, Leonie; you’re the sexiest person in the world.”
I kissed my way up the back of her insane legs to her perfect ass, then licked her spine as I crouched above her. I couldn’t say that I loved her, not yet. The prospect was terrifying, and the only reason I went along with it was because I really wanted to have sex with her again, and because I didn’t believe for a second that her emotion would last very long.
She twisted around and we grappled and kissed, our naked bodies sharing heat and pleasure as skin contacted skin, lips, tongues, fingers, penises.
She lifted herself up on one elbow and stared down at me with her vicious inescapable eyes, her wonderful hair falling around us while she grinned her infectious grin.
“I want to fuck you, and live with you, in your house.” She told me, “I want to look after Heath, and look into your crazy blue eyes while You suck my cock, and when I suck your cock.”
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