Stranded on Tranny Island
Copyright© 2026 by storyace
Chapter 6
Erotica Sex Story: Chapter 6 - 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
Heath was growing; he was 10 years old now, and a dynamo of crazy kid energy. Money was rolling in; I was unloading a boat every day, raking in dock fees. I was doing repairs too, I had a few boats up on the dry and I hired a lady welder. I thought she was a ladyboy until she told me she was pregnant. I had a carpentry shop, engine repair, and an electrician.
The solar power business was going stronger than ever.
I stayed celibate for a couple of years after Leonie left me. My heart, my cock, and my ass needed to recover.
I had the idea I could get Leh and Henrieta back when Olaf died; He said it himself when we were there for dinner.
“Damn Olaf, when you got back to the island we all thought you were a goner.”
“So did I.” he said, “I gave away all my money and resigned myself; and instead, I’m in remission. Man, every day of life here with my girls is a gift from God. My last scan was completely clean, I even went for a surf yesterday. Thank you, Fred.”
“Me? I didn’t do anything.” I said in surprise.
“You helped me a lot, and you helped my girls. Henrieta says you’re the only man who ever treated her as an equal.” He said.
“She’s not my equal, she’s better than me.” I said, looking over at where she and Leh were laughing with Heath over a video. “She’s built a business with 30 employees, it makes more money than the marina.”
I started thinking about getting together with another lover; there were straight tourists now, yachties, all sorts. And then Heath came running into my room one morning waving his Ipad excitedly.
“Helen is coming!” he exclaimed.
Well, that would be a first, I thought prophetically.
I met her at the plane, and rode her up to the house on my motorcycle. She hugged Heath, and I left them to catch up. We’d stayed in touch by email, but we hadn’t seen her in 4 years.
Helen had changed; her bright happy demeanor seemed scorched now, she was traumatized by what she’d seen.
Leonie came up for dinner, and we all had a great time. Hellen slept at Leonie’s place.
The next day she came back, and we talked more; like we used to, our brains seeming to synchronize over coffee.
She was only here for a visit. I looked into her bright clever eyes longingly; She wasn’t crazy sexy like Leonie, yet I still loved her. She’d changed though; there was pain behind her eyes now, a darkness that she tried to hide.
Helen was much smarter than me, and better educated, and she never rubbed it in. She spoke gently, so unlike our towering governor.
“Stop that!” she admonished me. “It’s good to see you, but you know I’m not staying.”
“Why not?” I asked, “We sure could use a doctor who understands trans issues.”
“I’ve been working in Gaza.” She said, “It’s crazy there, I’m working 16 hours at a stretch sometimes, people are dying like flies, at the same time I save lives every day.”
“It’s dangerous though.” I argued, “You’ve done your bit there now, don’t you think?”
“You don’t get it.” She told me, “I love it; saving a life is a kick. I’m just here to see you and Heath, and to...”
“Yes, what?” I pressed her.
She got up and stepped into the house, facing me from just inside the doorway as she opened her trousers and pushed them down her thighs. She had a little patch of black hair between her legs, and nothing else visible. She stared at me blankly, trying to hide her fear.
Fear of my rejection, I realized. This amazing person, war-zone surgeon, was worried I might reject her.
“I’m fully transitioned.” She said, “I had the operation almost a year ago.”
She looked into my eyes meaningfully as her meaning slowly arrived; she’d brought her new virgin vagina to me.
“Shit, Helen.”
“No!” she laughed, “No more shit, that’s the whole point. The anus has a biological function, and sex isn’t it.”
I got up and stepped inside too, took her hands and looked into her dark eyes; her pants were still around her legs so she was sort of helpless. I reached around behind her and gently ran my fingers over her lovely little ass. She looked up at me and smiled nervously.
I wrapped my hands around her bottom and pulled her tight as I lifted her from the floor so her feet came out of her trousers; she laughed and wrapped her arms around my neck.
“So, you just came as a sex tourist.” I said, “You want to have your fun, then go back to your job, leaving another broken heart behind you.”
“Yes.” She laughed, and kissed me.
Ah, Hellen. I loved her more than any of the others. She never needed me for anything, and she didn’t need me now either. She wanted me, and that was beautiful.
We saw Leonie walking up the hill with Heath; they looked funny, she was so tall they could barely hold hands.
Later, the boy was asleep and we were alone again at last. I took her hand and led her to the bedroom where I’d banged her in the ass hundreds of times. I undressed her slowly, and made love with her again.
Her skin so soft, so smooth, her hair, her mouth, her lovely ass, so nice to touch.
Her vagina; well, to be honest it didn’t look great. It tasted ok, nothing like a natural one though. Anyway, the anatomy was never the important thing to me. She looked afraid, and I did what I could to calm her, reassure her that she was beautiful, desirable, and that I still wanted her.
“Well, I guess you still want me.” She noted with a laugh as she held onto my hard cock.
“Do you still want me though?” I asked, which might seem an odd question after she’d flown thousands of miles to get here.
“I’m afraid.” She admitted as I opened her knees and put my tip against her untested slot, “I don’t trust anyone else, not for this. Only, well, maybe I should have started with someone a bit smaller!”