Captain Outrageous Ladyboys.
.
.
.
Captain Outrageous
is one of Asia’s leading ladyboy photographers. He has lived in the region for donkey’s years and has been involved in the ladyboy scene since long before the advent of the internet and digital cameras. We got together over a case of Beerlao and had a bit of a chat.

Captain, how many boob jobs do you think you’ve sponsored over the years?
Three and a half! In each case I have paid up for someone I cared about. In one case there was a distinct possibility that the ladyboy in question would have been passed A1 for drafting into the military. Up to 10 percent of 18-year-old Thai youths are selected each year for two years’ military service.

She was terrified at the possibility, and nearly fainted with happiness when I offered her the boob job. Extreme feminacy is about the only way out of being drafted ‘ the army isn’t big on troops with tits. The half, by the way, was for a ladyboy who only had 50 percent of the cost of the operation. I told her she would look silly with one tit, so I gave her the balance as a birthday present.

You’ve been involved in the ladyboy scene in Asia longer than most, long before there was any such thing as the internet. How did it begin for you?
I was a young journalist on my first ever trip to the Far East, to Singapore. I was with a small group of other people, and we were met at the airport and taken out for the night. We went to Newton Circus for some hawker food, and then one of the local people suggested a visit to Bugis Street. None of us had heard of the place or its reputation, but anywhere that sounded like Boogie Street had to be fun.

Old Bugis Street SingaporeOld Bugis Street

We arrived and sat at a small table. The place was packed. I was tired, drunk and jet-lagged after the 14-hour flight. Probably the best state to be in to witness what came next, for at about midnight, out of the shadows and the sidestreets, came these gorgeous creatures. They looked to me like delicious oriental girls, and there seemed to be an endless number of them.

If there were women seated at the tables, they would pose for photographs. Where there were only men, they would sit down and whisper in your ear such dirty things! I had no interest in men, and in fact I was married. But I felt hot with excitement, the kind of rush you feel when you are an adolescent getting to know girls for the first time. I didn’t really understand what they were, but I knew that I desperately wanted to find out.

The old Bugis Street is something of a legend. Tell us more about it.
Bugis Street was on the edge of Singapore’s old Arab Quarter. It was named after the Bugis traders who would sail between Sulaweisi and Singapore during the colonial era. It was simply a crossroads lined with old shophouses, but at night it became a streetmarket with the most wonderful food served from the shops and from hawker stalls lit by kerosene lamps. There was no traffic - the street was totally blocked by food tables. You would sit and eat, and drink endless bottles of cold Tiger Beer.

Captain Outrageous LadyboysI don’t know how it became a magnet for ladyboys, but I assume sailors used to come here in the 1950s and 60s for the food and beer and the souvenirs you could buy from the market. But gradually, the ladyboys became the main attraction.

The Singapore government of course hated it. The street was knocked down in the mid 1980s, ostensibly to make way for a station for the mass transit system. Although many people couldn’t help wonder at the fact the station was underground! I walked around the area when it was being demolished, feeling very melancholy.

So was Bugis Street all transsexual or was it mixed?
It was ALL transsexual! Not a genetic girl in sight. I came to realise later that the ladyboys were from Thailand, Malaysia, Indonesia, the Philippines. A lot were from Indonesia. Almost none were Singaporean, I would think. The ladyboys would have been doing what their ‘daughters’ do now: come into Singapore on whatever length visa they could get, make as much money as they could, and ship out on the day their visa expired. Only to come back again as soon as they could. The kind of money they could make in Singapore would have been fantastic compared to what they could make at home. And it still is. Two Thai ladyboys who are close friends have made enough money through a couple of trips to Singapore recently to pay for a sex-change operation.

Did you already know at this time that Thailand had a large ladyboy population?
No, I had no idea. I had never been to Thailand. And when I did make my first trips, soon after my first visit to Singapore, I glutted on the genetic girls. It took me a while to find the ladyboys. But when I did, of course, I became a helpless addict.

Captain Outrageous LadyboysLondon must have seemed pretty drab?
I bedded my first Bugis Street ladyboy, and when I got back to London I made the mistake of telling people in one of the local pubs about it. I presented the episode as an interesting and colourful experience, rather than the mind-altering sexual explosion it had been. The hostile reaction I got made me button my lip on the subject for the next 16 years. It was only the advent of the internet that allowed me to open up on the subject.

But back in London, I longed for ladyboys. There was a porn shop opposite Victoria Station that I used, and when I came back from that first experience I went looking to see if they had any material on ladyboys. I found a couple of American magazines about transsexuals, with mostly black-and-white photographs, but the models were so unappetising that I never looked at them again, and threw them away, shredding them carefully before I put them in the dustbin. The nearest thing to a ladyboy that I found in London was a rather sad little queen who worked in an after-hours drinking club I went to in Fleet Street. I looked at him, with his see-through top, and thought’.no, not even in my desperate state, I couldn’t’.

The British dramatic arts have always been a fertile breeding ground for campness. Danny La Rue was a famous female impersonator way back in the 1960s. As kids we just laughed and forgot about it. We went back to our National Geographics and the ladies underwear section of mail order catalogues for sexual fulfilment. Did such acts ever prod your curiosity?
Not in the slightest. I found Danny La Rue to be tedious and embarrassing. As you say, there is a long tradition of men dressing as women in pantomimes and in stage farce, but even as a kid I would find them silly and completely unfunny. Drag queens are a different species, but they always seemed to be middle-aged men trying to fulfill fantasies of their own, and I had no interest in them, didn’t find them provocative or entertaining.

Captain Outrageous LadyboysThai theatre also has a long history of casting males in female roles and of course there are the famous ladyboy cabarets. What is the history of those?
Ancient Buddhist texts including the Tipitaka, on which the Buddhist scriptures of Thailand, Burma, and Sri Lanka are based, recognise the existence of at least three sexes, and sometimes as many as five. What is apparent is that transsexuals have been recognised in Thailand since very early times.

Traditionally, Thais believe that karma is the reason a person is born as transsexual. The kathoey is paying back for transgressions in a previous existence, and is therefore to be pitied and possibly even envied, because she is in the process of working off a large spiritual debt, presumably leaving the way clear for a better existence next time round.

So the kathoey is accepted as being part of society?
Yes, you will find them throughout Thailand. In provincial towns everywhere, you will find a kathoey community. In the remotest villages you are even likely to find one or two. Visit a village fair, and you will almost invariably see a kathoey beauty contest, or a stage performance featuring kathoeys. So the cabaret concept grew out of this. You will find in the rural areas and even in Bangkok small groups of kathoey entertainers forming a cabaret, and they get booked for community parties and so on.

The big Tiffany’s style cabaret theatre is however a recent innovation. Some years ago, I got to meet the man who started Tiffany’s. He was gay, but not a kathoey. In the late 1960s he had opened a gay bar in Bangkok, which he said was the first of its kind. Trying to decide upon a New Year party theme one year, he had taken up a suggestion from his German boyfriend that he stage a transvestite cabaret. The German had in mind the notorious transvestite shows in 1930s Berlin. What was staged that New Year was far more modest: one of the bar workers was dolled up in a wig and a dress, and lip-synced to records. But it was a huge success.

Captain Outrageous LadyboysNot long after, the bar owner heard that the lease on a small bar in Pattaya, then an emerging resort with little more than a huddle of beach bungalows and entertainment outlets, was available. The bar was just a beer bar, a conventional shophouse, and it was called Tiffany’s. He took on the lease, and staged transvestite shows there. The place became famous, and eventually a local businessman became involved and Tiffany’s moved to its present huge theatre in North Pattaya. Several of the players went off on their own, and formed Alcazar, which now has an equally large theatre on the opposite side of the road.

We’ve both been around the region for a long time. Is it my imagination or has the ladyboy population in Bangkok exploded over the past 10 or so years. If so, why do you think this is?
Yes, it has. And it has very little to do with genuine transsexualism. I don’t think it is possible to identify one particular reason, however. I can see several. One of course is that gays are more accepted than ever before, and an effeminate boy might be more confident taking his lifestyle to the ultimate and becoming a ladyboy. But not all ladyboys are gay, at least not in the accepted sense. I believe that for some it is a form of rebellion against society, and Thai society is still essentially very conservative.

Most ladyboys are from the poor working class, and for them, even if they have a reasonably good education, the options are limited. The vast majority of Thais come from this class, because the middle class is still a very small part of society. A sensitive young boy might feel repelled by the more macho aspects of being a conventional working-class Thai man. He might feel attracted to show business, or the chances of earning big money by having sex with men, preferably foreign men. At school and at college he mixes with boys who have the same thoughts. They experiment with makeup and with their sisters’ clothes, and someone introduces female hormones into the group.

Hormones are very inexpensive and easy to buy in Thailand. If you start taking female hormones when you are in adolescence, then you are unleashing something it is difficult to control. You begin to develop breasts, and you start taking an interest in boys.

Captain Outrageous LadyboysThe idea of escaping poverty by having sex with someone of your own sex is not as unlikely as it may appear. It is hard for us to appreciate just how dirt-poor so many Thai families are. In the rural areas, many of them still live off the land. The tolerance of Thais towards homosexuality means that young Thai men tend not to have hang-ups about same-sex escapades. This is why, if you go into any of the gay bars in Bangkok, Pattaya, Phuket etc, you will find most of the young guys working there are essentially straight, not gay. They are doing what they do to earn money, and they probably don’t feel too guilty about it.

I mentioned earlier the Thai military draft, and I think this is also a factor in many young boys becoming ladyboys. One of the few ways you can avoid being passed A1 for the draft and a ten percent possibility of being selected for two years in the armed services is to show extreme effeminacy.

Ladyboys don’t just earn a living from show business or from the sex industry. There is a huge number working behind the scenes in Thailand’s enormous media industry: in wardrobe and costumes, makeup and hairdressing and so on. Thailand has one of the world’s largest cosmetic and beauty sectors, and ladyboys will be found here, in the beauty salons and the hairdressers and the department stores, because they are often brilliant with makeup and styling.

They make outstandingly good dress designers, and the garment sector is a major employer. You can also find many working in the travel industry and for hotel companies, and in restaurants and shops and offices. Sometimes it seems as if to be a ladyboy is actually a positive factor in going for these types of job!

What I’m trying to say is, that for many youngsters the options open to them as ladyboys might well seem more attractive than the options as young men. They are often making this choice in their early teens, so it is not always a rational choice, but you can see how they might be pulled and pushed in that direction.

One more thing. I have begun to see in recent years a growing number of families that have more than one ladyboy member. One son will decide to be a ladyboy, and he will look so good that his younger brother will decide to follow. So you can see how easy it is to influence a young person in this way.

Of course Bangkok has always been famous for it’s nightlife, which has attracted people from all over the world. Now the internet has given ladyboys much greater exposure than ever they had before, and people fly in to meet them. What is the attraction?
Captain Outrageous LadyboysThere is no doubt that the initial attraction is that you have a girl who has a cock. The penis is a remarkably beautiful part of the body, but usually it is stuck on the end of a smelly, aggressive man. Put one onto an attractive girl, and you change the equation. You also tend to lose the idea that admiring an erect penis makes you gay. In my experience of ladyboy lovers, and believe me I have met or corresponded with a vast number over the years, most are heterosexuals with a strong libido. Their interest in sex takes them beyond the conventional, but not into the realms of being gay.

Once they experience a relationship with a ladyboy, they find out how addictive it is. You have a partner with the aura of a girl, but she will still have the sex drive of a male. The result can be explosive sex. And you are going further than before, doing things you maybe would not have thought of, but then finding out just how erotic they can be. You are seeing a body that is a blend of female and male, something you have never seen before. You also find yourself getting to know a different type of person. Possibly a vulnerable person, a mixture of emotions and desires and insights that gives you a different take on humanity altogether. Life can seem very bland when you get back home, because this is possibly the most exotic, erotic experience you have had.

Have you ever tried to live with a ladyboy as a regular couple?
I have tried it only once, and it was a good few years ago now. This was with a ladyboy from Pattani, in the Deep South, and she was one of the most beautiful human beings I have ever seen. But Thais from the Central, Northern and Eastern regions are very wary of their Southern cousins, who they regard as being volatile and dangerous. Ethnically they are hard to define: there is a fine cocktail of Malay and Indian mixed in with many Southern Thais, along with Burmese and Chinese blood. And of course, as events are currently illustrating all too well, the South is an uneasy place, prone to exploding into violence. So was she, I’ve told the story on my own blog; The Third Sex - Some like it hot

Last question, but one that has to be asked. We all know that shooting porn is about creating fantasies but that behind the scenes it’s hard work and probably not as glamorous as it looks and you don’t get to screw all the models afterwards. BUT, you’ve got a ladyboy waggling her bum enticingly, the tropical sun is baking the pavement outside, the air con is rattling away on max but hardly making a difference and you’re streaming with sweat. Have you ever just thought, “oh fuck it!”, tossed the camera aside and given her one?
Sorry to disappoint you, but no, never! The reason is, that she is there to be photographed and that is what she is being paid for, and if I don’t finish the shoot I don’t have a photo set. Although this might surprise a number of people, I am very self-disciplined. I’m very critical of self-indulgent people. Plus, and I have to say it, I live in a very ladyboy-centric world. Sexual frustration is not one of my problems. I can survive a one-hour photoshoot without losing control of myself because an evening of galvanic sex is only a phone call away.

There is usually a degree of sexual touching during a shoot, and if she is a really hot model this can become quite absorbing. But really I’m trying to get her to a stage where she can wank off for the camera and produce a nice, sticky end sequence. But those I like, I invite back. There are a lot of them. They NEVER say no. I get to meet some great ladyboys that way!

Click the ad to visit the Captain’s main site or click here to visit his blog, The Third Sex