The Cruise to Heaven and Hell

Yeah well this is my story of what happened to us over the last few weeks but first some of my background. My name is Andrew, or Drew for short, though not many people call me that. I live in Sydney in Australia. I'm half Australian, of Irish descent, and half Japanese. I don't know who my father is. All my mum knows is that he was a Japanese businessman on a business trip staying in a particular hotel in Sydney.

To be perfectly honest, my mother used to work as an escort, that is, a prostitute. I gather that she worked for an agency who arranged her clients. They were always businessmen on short visits to Sydney. She would dress up nicely, go to dinner with them, even dinner parties, sometimes go to a night club for dancing or karaoke and of course later have sex.

Don't get me wrong. I love my mum. I'm not ashamed of her in any way. She is my best friend and I don't think any boy and his mother could be as close as we are. I don't think we've ever had a serious argument except for that time when I tried to find my father.

All my mother knows is that he was a Japanese man in his late fifties, she knows the approximate date and the hotel. Nothing else. I actually look half Japanese but there were other reasons that she knew he was the guy that she won't go into. My mum wasn't too happy about it but I worked up the guts to call the hotel and ask for their records from that time. Of course they basically told me to fuq off. My mum helped me to lawyer up... Well, you might think how can the teenage son of an ex-prostitute single mother lawyer up? There is something I haven't mentioned yet.

When I was five years old, my mum bought a lottery ticket. One of those jackpot lotteries where the prize accumulates if the main prize isn't won. Well she won it. The prize was thirty-eight and a bit million dollars. That sounds like a lot but just because my mum worked as a prostitute doesn't mean she isn't smart. At least she is smart enough to employ good financial advisors and I guess lucky enough not only to win in the first place but invest the money lucratively.

She's now worth about two-hundred million and that doesn't include my personal trust fund which is over five million. Something keeps poking money into my day-to-day bank account and it has over a hundred thousand in it. I have to be careful if I ever withdraw cash from an ATM because if I press the wrong button that amount is displayed on the screen. So yes, we are loaded but don't get the idea that we are posh. We're not. My mum and I are very down to earth.

Anyway, back to the story of my dad which is after all a complete flop. It never went to court. The hotel cooperated, or said that they had cooperated to their utmost but the records no longer existed. I have a long letter explaining how they had upgraded their computer systems multiple times over the years and that they were only legally required to keep seven years of records. The worst part was that they did actually have the old hard disks from computers that had been replaced until very recently when they had been sent away for secure destruction. All that was in a letter attached to a statutory declaration so my lawyer said that if they'd lied, they'd go to gaol.

So all of that story is just to say that the only serious argument I ever had with my mum was over that. I said that she should have realised that at some point I'd want to know who my dad was and looked into it earlier. She said that she was sorry but there's nothing that can be done now. Anyway from what she remembers, the guy would be in his seventies now. Who knows, he might already be dead. Frankly, I'm completely over it and I'm more sorry that I had that argument with my mum over it than anything else.

Though the other thing that my mum did that was in retrospect something I should roast her about was putting me into a high class school. She left school after year nine. She had a hard life. Her mother, also a single mother, died from alcohol when she was ten and for the next few years she was looked after by her grandmother. I just remember her, my great grandmother Marjory. I visited her in a nursing home but she died when I was six. At least my mum had the money to make her comfortable in her last days.

So she enrolled me in this high class school, the name of which I won't mention here. What's worse, it was run by the Anglican Church. I guess she wanted to give me the opportunity of a good education that she never had. Primary school was okay except for the religious stuff but when I got to the highly selective senior school, even though I legitimately got the grades required for admission, I was like a square peg in a round hole.

It's said to be hard for someone who comes into sudden wealth to maintain their previous circle of friends. My mum managed to do it. Yes of course she gave away a lot of money, sometimes paid people's debts, sometimes even put up bail, but her friends, though often considered to be on the bottom rungs of society, are not the types to sponge off of her. Not excessively anyway.

Yes my mum and I live in a nice apartment with a spectacular view over Sydney Harbour but on Friday and Saturday nights, we are often joined by the weirdest and most amazing group of people you can imagine. Sex workers, strippers, drag queens, extremely avant-garde artists and writers, transgender women, well in fact representatives from the whole LGBTQI+ spectrum, a few television personalities and movie people. So many times I've had to go down to the lobby to explain to the security guards that someone is an invited guest, oh and the thing I forgot to tell you is that my mum thinks that she's bisexual. Actually she's a lesbian going from the fact that she's only dated women for as long as I can remember.

Of course all these people have influenced me. I have a very open mind and very liberal attitudes. My mum's friends are just as much my friends, I might even say they are my family. They've influenced the way I speak which can be colourful if I don't watch myself. They've also always respected what I have to say and never treated me like a kid. For my birthday one of our friends, a tattoo artists among other things offered to do me a tattoo as a present. My mum had to give written permission because of my age and she didn't want me to have anything too big. I got a turtle on my upper arm while under the influence of some pretty special cannabis.

Actually that's one thing my mum doesn't tolerate. Addictive drugs and excessive alcohol, at least not inside our apartment. She only allows social drinking and cannabis and I wasn't even allowed those on the nights before school.

What a shock when I got to high school. Every boy, it was an all boys school, acted as though they had a baseball bat permanently jammed up their arses and spoke as if they had an egg in their mouths. I had to wear this extreme uniform. My hair had to be cut short at the back and sides and I couldn't let my mum's friend Grace to put plats or bright colours in it. She still came over and cut it every week with as much style and as little artificial colour as the requirements allowed.

Another thing I didn't mention is that my mum, now just over forty, is spectacularly beautiful. I don't think many sons, especially gay sons would say that about their mums but it's true of mine. She's just naturally beautiful but she does work to maintain it too. Grace comes over every week to do her hair, her nails and stuff to her face. Actually she does some of the same things to me which I don't mind. They've always made me wear moisturising sunscreen even when I'm not going out. Yes I've definitely inherited my mother's proportions as well as my father's Japanese eyes and nose but my mother's friends think I'm very handsome. They all fuss over me and put on a great act as if an adonis has arrived when I enter the room. When I got a pimple, the only one I ever got, it was like a special meeting of the United Nations Security council had been called.

Yeah, I mentioned in passing that I'm gay. I know realising that you're gay, coming's out to yourself and then coming out to the various circles of family, friends, etc.. is a big trauma for most boys but it was no big deal for me. It was funny that when I started high school, some of the guys often said that I was gay. They meant it as an insult but I'd grown up with guys who are gay so it was no insult to me. I never denied it and when I realised it was actually true, I said so.

Actually I realise now that the thing about trying to find my dad was something to do with realising that I'm gay. It was funny that we were watching a show on TV called Ninja something from USA with a few of my mum's friends. Some of the women were talking about which guys were hottest. I just got caught up in the conversation and gave my opinions on which types of guy I thought was sexy. When the show was over I said I had to go and do some homework. When I finished I came back into the living room and saw that all eyes were on me.

We shared a few cones and then we got talking. Yeah I know some crazy religious types will say that those people made me gay but that's just crap. Me, my mum and her friends just had a very open, honest and intimate conversation helped along by the cannabis after which it became very clear to everyone, not least myself, that I'm gay. I guess what is even more unusual is that my mother seemed stoked.

A few days later we had a party to celebrate my coming out after which we all went on a tour of Oxford Street, the main gay area in Sydney. The people I was with had the connections to get me past security, even into a basement leather bar. At each place they made the announcement that I had just come out which caused a huge cheer and many people to try to buy me drinks. My mum only allowed ginger ale though. After that my mum or one of her friends shouted drinks for everyone there. That happened at a dozen places that night.

Now I don't want to give you the wrong impression about my personality. I'm an introvert. Of course I'm very comfortable with my mum's friends and as I've said, they are just as much my friends. Even though they are all at least eight or ten years older than me, they are the people I've gone to see movies with, gone on trips with, hung out with etc. often without my mother. I never made a single serious friend at school and until very recently, I'd never had a friend my own age.

Of course I pretty much got along with everyone at school. I was one of the top students academically in one of the top schools in the country. I admit that I'm good looking and smart and that attracted people to me but I just couldn't make any strong friendships with them. Part of that might have been because I was the only openly gay boy in the school and so other boys were worried that if they got too close to me then they might be thought to be gay too. Another part of it might have been that I just had enough friends outside of school and I didn't have to struggle for acceptance with them. To tell the truth, I just wasn't interested in the boys at school. I didn't have anything in common with them. If they'd invited me to their homes, they'd have been embarrassed by my attitudes and the way I spoke and frankly, if I'd invited them to mine, I'd have been embarrassed by theirs.

The headmaster and some of the teachers didn't approve of me and they would have liked to get rid of me but in addition to the substantial fees, my mum had made a few large donations to the school. When it became common knowledge that I'm gay, I was hauled into the headmaster's office and given a lecture on the Christian values and beliefs of the school community and that I'd have to respect them if I expected to stay there.

They could threaten all they liked but a private school would never expel someone with my academic performance because to them, school rankings mean money. Nevertheless, I came to realise than some of the teachers marked me harder than they did other students. Of course the final exams were independently assessed by the state education department so I didn't care a lot.

When I came to swimming on the first day of the season and everyone saw that I had a tattoo I was hauled off again, well actually, the headmaster came to the dressing room. I had no idea what their problem was with my tattoo. I still don't. It's just a turtle for fuqs sake. Even though there isn't anything explicitly in the school rules against having a tattoo, I was suspended and they called my mum to complain and ask her to come to a meeting about me at the school. She basically told them to fuq off, not in those exact words, and she didn't go to any special meeting. I had to wear a band-aid over my tattoo at swimming which always soaked off anyway.

In whatever spare time I had, I read. Ancient history, archeology, anthropology, art, religion. At school during the breaks I usually sat by myself and read. My mum says I should go to university next year and I want to go too if I can find a good archeology degree. Of course there's no hurry. It's not as if I have to find a job.

Statistically, there must have been other gay guys in my classes at school but I never even suspected any of them. Of course I knew plenty of gay men in my mum's circle and some of them flirted with me but none of them ever tried to touch me sexually. I'm guessing my mum had laid down the law as far as that goes so it shouldn't be any surprise that I finished high school last year a total virgin. I didn't even have anyone to go to my graduation formal with so I didn't go. I was supposed to accept some award for getting the highest score in the final exams and give some speech but I just flipped them off.

Of course I fapped all the time. Too many times my mum caught me which is pretty shocking. Once I had been edging and finally decided to let go when she walked in and started asking me something.

"Oh, oh, sorry Andy. I didn't see anything," and she backed out. Seconds later she was back, her hand over her eyes, my orgasm ruined.

"Just let me get this school blazer. If you get cum on it you'll never get it off."

She picked up the blazer from my bed and backed out again.

"What the fuq mum!" I yelled after her. It cost me a terrible case of blue balls. And by the way, if anyone else calls me "Andy" without my express permission, I will poke them in both eyes.

She caught me fapping to porn on my MacBook once. Later she demanded to see what I was watching. I reluctantly relented. It was just a Helix movie of two hot young guys fucking.

"Yeah, that's okay," she said but then proceeded to give me a lecture on what kinds of porn are not okay. Actually as you can probably tell we are pretty open with each other about everything. You'll probably be pretty shocked to hear that I see her naked very often. She sleeps naked and mornings she wears a silk dressing gown that she doesn't even bother to tie up around the front unless guests are staying over. Sometimes not even then.

To tell the truth, I am the same. Even though I have my own shower I usually use hers because I like the hand shower thing that she has. Yeah I could have one installed in mine but what's the point? I sleep naked too and mostly I walk into her bedroom and in and out of the shower naked. I know some guys are shocked by that but why would I care if my mum sees me naked? I'm pretty sure that she's seen me naked every day of my life. She even comments on my cock, flatteringly I might add, and I'm guessing she's seen enough to know. I have to be careful if she's got a guest, always another woman, in her bed and of course I'm not comfortable with her catching me fapping.

The thing she's never caught me using and she doesn't know I have is a dildo. Actually one of my mum's friends, an old gay guy called Paul bought it for me as a birthday present and snuck it to me at my party. Paul is what's called a "daddy" and he's into guys much much younger than himself and that includes me. He does flirt with me and I don't mind that but he never goes too far. I wouldn't be surprised if he gets off imagining me using his present on myself but that doesn't bother me either.

I do chat to guys online, mainly on gay servers on Discord and occasionally I've fapped and even used my dildo on video chat there but I always do it with guys in the US, Europe to India and I avoid showing my face. I don't use any of those hookup apps because I'm just not into the idea of a hookup. I really can't say why. If you pinned me down I'd just say that I'm too scared but that doesn't really cover it.

Our apartment is a very weird shape. Like an eye. Lenticular to use the correct word. One whole side is glass looking out over the harbour and there is another apartment building over to the left but my mum says that the glass is mirrored and no one can see in during the day. That doesn't stop her, and to tell the truth me, walking around the apartment at night in the nude with the lights on. If they want to look with binoculars, who cares?

Her fortieth birthday was in the last week of January and she got all weird and immature about it. We decided to go away on a holiday to avoid her friends making a fuss. She booked a cruise that took in the Caribbean, Central America and Mexico that started in Los Angeles in California and ended in Miami in Florida and went for six weeks. It would have to go through the Panama Canal which I thought would be interesting but I was excited by it mostly because there would be excursions to various Meso-American ruins.

It wasn't the first time we'd been overseas on holidays together. We've been to Japan twice, New Zealand, Bali, Thailand, Greece, Turkey, India twice, France and England but never to America. The first time we went to Japan we flew economy because my mum had this crazy idea that we weren't posh enough for first or business class. She gets this way every now and again though that was the only time she did it on air flights. Why torture yourself when you don't have to?

We flew Sydney to Honolulu, spent a few days there and then flew on to LA. The ship was amazing. It wasn't one of those huge theme park like modern ships with water slides and things. It was smaller and older but fitted out in extreme luxury and retro style. There were no children allowed and although everything about it was classy, it didn't take long for me and my mum to get the vibe that this was a cruise for wealthy swingers.

The passengers were also vastly disproportionately single women. The few men that I saw other than the crew averaged in the seventies. A lot of the crew were young hispanic guys and some of them were extremely cute but whenever I got over my shyness enough to flirt with any of them they got very formal and rebuffed be. I'm guessing that fooling around with passengers is not allowed. My mum thought I would be bored. I was a little but I occupied myself with reading about the places we would be stopping.

Then on the third day out at dinner I saw a guy about my age also with a woman about my mum's age sitting at a table across the restaurant. When he saw me looking at him he smiled and waved. I waved back. When we were finished eating the guy came over to our table followed by the woman.

"Hi, I'm Autry," he said to me. "I think you're the only dude my age on this ship."

"Yeah I think so," I replied half standing to shake his hand. "I'm Drew." My mum glanced at me. She doesn't like Drew. For her it's Andrew or the annoying Andy.

"Oh this is my ma," he said.

His mum smiled at me and then at my mum.

"Hi, I'm Carol, Andrew's mother. Would you like to join us for a drink or coffee?" said my mum.

"We'd love to," said Autry on behalf of both of them but still smiling at me.

"Hi Carol, I'm Dahlia," said his mum to mine.