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Transport of delight

ladyboyEarly on Friday evening, Sukhumvit Road being jammed solid with traffic, I decided to take the Skytrain to Siam Square. Getting on at the same station as me was a ladyboy. She was very much the in-your-face type: as tall as me in her high heels, and wearing a bright red little cocktail dress that had no back and which was open at the front so that her silicon boobs were almost popping out. She stood a few feet away from me in the packed carriage. She was not at all my type, so I simply stood strap-hanging, wearing the absent-minded expression that I use when I’m watching people.

The train was full of office workers, there were a few school kids, and even a handful of girl scouts. Nobody paid any attention at all to our fellow traveller, who stood demurely minding her own business next to the door. As unobtrusively as I could, I looked at all the surrounding faces, and there was not one sly look, not one giggle, not one whisper. Our friend disembarked, as I thought she would, at Nana, no doubt bound for one of the ladyboy bars in Nana Plaza. As she stepped out of the carriage, there were no embarrassed grins, no rolled eyes…nothing. She had simply been another passenger.

This I think says a lot about the Thai character, and about the tolerance of ladyboys in Thai society. I would not have given much for the chances of our friend if she had been travelling on the London Tube. But to the Thais, a ladyboy is a ladyboy. End of story.

Of course we are all aware, those of us who follow Thailand’s third sex, of how there has been an enormous increase in the ladyboy population in recent years. Of how there are now so many ladyboys in schools throughout the country that separate changing rooms and toilets are provided for them. Of how if you visit a beautician or hairdresser, or pass through the beauty section of one of the big department stores, you are going to find a number of ladyboys and femboys working there.

My neighbourhood 7-Eleven has three ladyboys on the staff, out of a total payroll of no more than ten. During a stroll through the nearest supermarket the other evening I noted a ladyboy on the fresh foods counter, another in the drinks section, and a third helping take deliveries of a stack of groceries. A 19-year-old student who turned up for a photoshoot at the weekend, and who is studying art at one of the big universities, ran out of fingers when she tried to count how many of her fellow students are ladyboys. (Good potential for new models there!)

One wonders how far it is all going to go. As far as work in the mainstream is concerned, then there is plenty more capacityladyboy to absorb more ladyboys. Given the increasing tolerance, there is no reason at all why a well-educated ladyboy should not enjoy a long and fruitful career in the public or the private sector doing the kind of job that we do not necessarily equate with the third sex. During the course of photography I have met ladyboy students on business administration, computer studies and marketing courses, to name a few that come to mind. A few years back I discovered a whole ladyboy community on a local government administration course at one of the Bangkok universities, and they must all be well on their chosen career paths by now. Thai society itself is changing, as anyone who follows the political situation will know, and there is a growing class of people who are coming out of the working class and moving into the middle class. Ladyboys, it would appear, are part of the movement.

Bottom of the class

ladyboy schoolgirl

Sargent Shameless and I were talking during the week about a ladyboy we had both known a few years ago who worked at Hi!Boss in Pattaya. She was not only one of the cutest ladyboys I have ever seen, with real star quality, but she was also a smart little cookie. I remember going with her once when she wanted to draw money out of her bank account, and peeping over her shoulder at the ATM screen I saw she had almost a quarter of a million baht in her account. And she was still only 19. 

She had always refused to have her photograph taken, by me or anybody else, which was a great pity because she really was a girl, and nature, as a joke, had stuck a willy on her. She would have been fabulous to photograph. 

Talking to the Sargent about this natural beauty she had, I mentioned that she had told me she began taking hormones at about the age of 12. She said that at her school in Pitsanulok there had been as many as a third of the boys in her year who were experimenting with becoming ladyboys. The Sargent was shocked (he is hard to shock, believe me). If that is the case, he said, then there really is a third sex emerging in Thailand.

We went on to speculate about the effect that adolescent ladyboys have on the other male members of a school.

We all remember what it was like to enter adolescence and to suddenly become aware of girls, and the obsession one develops about them. But how would we have reacted if some of our schoolmates had begun to develop into a third sex?

Okay, for those of us from the West the idea is derisory. The nasty, stinky little kids in my school were already grotesque enough as males. And when I go back to London these days and see the feral youth that the country is breeding I doubt even their own mothers find them attractive.

But transfer this prospect to Thailand where ladyboys are, and have long been, part of the culture. Where ladyboys can be far more beautiful than genetic girls. Where a boy taking female hormones and wearing girls’ clothing can look like a little doll. The memory of my little friend from Hi!Boss comes before me as I write this.ladyboy pubic hair

So, what does that do to your emerging masculinity, if you are a straight kid, given that ladyboys are by their nature sexually provocative and not demure like genetic girls? When you are literally bursting for sex, but the girls in your school and neighbourhood are off limits? When the fledgling ladyboys are taking female hormones and looking for boyfriends?

I’m sorry, but I don’t really know.

The Sargent told me of a ladyboy friend of his who, so she told him, would regularly entertain the local lads after school, and that she would often find an easy way of earning some cash when she was walking home through the fields. A lot of Thai men enjoy going with ladyboys. Many keep a ladyboy mistress. There is no stigma about having sex with ladyboys. All I can think is, they learned this at an early age.

Utterly Shameless

captain outrageous, shameless

For those of you who still think that  Sargent  Shameless is an alter ego I created, today I offer some evidence to the contrary.   You see, out of nowhere, the Sargent confronted me with this highly personal questionnaire knowing  very well that although I am a private sort of chap it would be awkward for me to refuse his request.  So I pour my heart and soul into answering the questions as best as I can, and what do I get in return from the Sargent?  Snappy one liners mocking my thoughtful answers. Would I put myself through this if I was in control of the Sargent’s persona?  Definitely not.  I am thinking I should have ignored him and his  questions, but I do get him to tell the world about his entertaining personal life, so it’s only fair that I tell something about my own.  So , here I am more raw and vulnerable than ever before (and never again Shameless!).

I was very impressed by the Captain´s follow-up piece to my reflections on Thailand´s ladyboy boom.  His own reflections are underpinned by years of experience and expertly drafted showing his fans why he is the CAPTAIN and I a mere Sargent. Well, at least the Captain admitted that I am not just a big hairy dick on legs seeking at all times to lodge inside sweet girlie-boys butt cheeks.  I would like to further establish my credentials as a visionary on ladyboy buggering by challenging the Captain as follows:
10 Straightforward questions the world is dying to know about the Captain:
 (followed by your Sargent´s TAKE on the unexpectedly (for me!) candid responses by our sweet and sensitive Captain.)

captain outrageous, shameless

1.At what age did you have your first ladyboy experience? 

I was very young! Young enough never to have heard of ladyboys. But this was pre-internet. Unless you travelled to the Far East you were unaware of their existence. I saw my first ladyboys in Singapore, in the old Bugis Street. I did not know what they were. But what I did know was, that they looked gorgeous and they came on really strong at you. For a young English guy, on his first Far East trip, recently married as I was at the time but deeply unhappy because the relationship wasn’t working, it was all heady stuff. Were these girls really girls? What was under those dresses? It really wasn’t difficult to find out.

The Sargent´s TAKE: It sounds like the 1974 classic movie “Emmanuelle” but starring a confused Brit instead of the sexy Sylvia Kristel.
2.Had you previously had sex with anyone with a penis?  If not, did you think about it?

No, I hadn’t. I hadn’t even seen anyone else’s penis, except under changing-room conditions or during the wanking-off sessions that nasty, stinky little English schoolboys get up to. I hadn’t even thought about it, except to idly wonder from time to time, as we all do I suppose, what it would be like to be in the girl position. But I never fantasised about it. Never thought about performing fellatio on anyone. My thoughts were entirely about girls, and I was obsessed by them like any other normal youngster. I quite simply did not, and do not, like men. I find men to be physically repulsive. I knew very few people of my own age who were gay, and those I did know didn’t talk about their preferences. People didn’t in those days. captain outrageous, shameless
The word “gay” wasn’t even in general use then. There were a few middle-aged homosexuals around, but they kept themselves to themselves. In my very early days as a foreign correspondent I remember fending off the advances of a Saudi taxi driver, and of a Swedish man in a Stockholm bathhouse. Incidents like these were so rare that they made good stories for later. That shows you how sheltered a life I must have led. The only indicator that I can fish up out of my memory as to the future course of my preferences was an absolute obsession about girls’ bottoms. I could fall in love with a girl because of the shape of her fully-clad bum. And I certainly fantasised about having anal intercourse with girls. But this was a far more straitlaced era and it was difficult enough to find a girl who would have ordinary sex with me, never mind about taking it up her rear end. Suddenly, from a rather stuffy and buttoned-down English background, in Singapore I was in an extraordinarily erotic environment. The exoticism overwhelmed me. I’ve always, throughout my entire life, been up and ready for adventure. Thus it all started…The funny thing is, that although I had never given much thought to penises, they have become another obsession. The cock is an extraordinarily beautiful and exciting thing. A ladyboy with a lively cock – it doesn’t even have to be very big – is breathlessly exciting for me.

The Sargent´s TAKE: In brief: the Captain went for ladyboys because the women in his life were not surrendering their poop chutes to him; in the process, he discovered he liked Sai Krok (big, juicy Thai sausage).

3.Your photoshoots are unique in that they show models more raw and boyish than any of the other websites. Does this denote your own preference or those of your members?  Are you personally more into passable ladyboys or feminised boys?

captain outrageous, shamelessI have to say that it is the young ladyboys, still boyish yet with a feminine aura, that I find the most attractive. It is the natural blending of the sexes that I find alluring. I don’t really go for the heavily made-up ladyboys, or the over-the-top types. I don’t find young boys per se attractive. If they are very pretty and demure and slightly feminine, sometimes. But boyish boys, no. It comes back to my distaste for masculinity. The litmus test for how you feel about boys and girls is who you find yourself looking at when you are out in the streets: boys or girls. For me, it is and always has been girls. But when a teenage boy dresses as a girl, puts on a little makeup and sheds his masculine aura, then my interest switches. And this really can only happen at a young age. Once the feminised boy crests the age of 20 or so, the time is gone. She can go on and become a devastatingly sexy ladyboy, of course. But not a femboy.

The Sargent´s TAKE: The Captain likes young girlie-boys and is happy to share his interest with you.

4.Having got to know so many outstanding ladyboys, how have you managed to remain unattached?

captain outrageous, shamelessI think it is the sheer number. And the fact that ladyboys are always available. A ladyboy will never decline sex unless she really has a valid reason. When there are so many, it becomes difficult to manage time, never mind about managing a relationship. If that sounds a little presumptuous, so be it. I have fallen for a few over the years, but the current has always been flowing so strongly that my feelings have been overwhelmed. It is only when I look back at the photographs I took at the time that I can bring back the emotions I felt then. But ladyboys change physically, and quickly. That gorgeous, seductive 18-year-old will become almost unrecognisable within a handful of years. Typically, she will by her mid twenties be thinking about her future, about entering the mainstream as a woman, about opening a small business in her home town. She certainly won’t be the person you fell for a few years previously. Anyone entering into a relationship needs to think ahead.

The Sargent´s TAKE: The Captain is wallowing like a pig in shit.

5.If you had to choose between having sex only with genetic women or with ladyboys for the rest of your life, which one would you choose? Please give a brief rationale for your choice.
captain outrageous, shameless

It has been a while now, a couple of years, since I had sex with a genetic girl. I can’t say I’ve missed it that much. On the other hand I travel overseas regularly, and whenever I get to my destination I immediately start to miss ladyboys so much that I begin counting the days to my return. When I do get back, in the taxi in from the airport I’m on the phone making arrangements for the evening. I think that says my mind and body is telling me something. So, as long as I get to look at genetic girls, I could live very happily with only ladyboys.

The Sargent´s TAKE: The Captain is long past the point of no return!
6.  Do you relish ladyboys more for the sex or the access they allow you into their fascinating world?

captain outrageous, shamelessTheir world is fascinating, certainly. I like to find out all I can. But it has to be said that many ladyboys just don’t want to talk about it. They have made a decision and they have accepted it, and it no longer seems so strange to them. Much of my information and insight comes from regular sources, ladyboys who are real friends and who I have known for a long time. So I have to say that most encounters are for that explosion of sex, and once it is over I am happy for my friend to be on her way.

The Sargent´s TAKE: For the Captain access into a ladyboy´s world is pretty much the same as access into a ladyboy´s ass.
7.  Roughly, what percent of the models you photograph for the Captain Outrageous website do you have sex with? We know you don´t have time and have to remain professional, blah blah blah…but surely you must help the poor models clean up the little groin mess you make them do…please spill the beans.

The percentage is actually small but the number I photograph is very large! Many of them I do not feel attracted to. And then there is the fact that while she is being provocative, the model would certainly be up for sex if I was to put the camera aside. But once she has shot a load, then she has lost interest. As one does. She wants to get off home, or to work, or see her friends. Whatever. I do help them clean up. I do like to gently squeeze a slippery cock and run my fingers through pubic hair that is dripping with cum. captain outrageous, shameless
I do follow them into the shower, if they don’t show any signs of objecting. I do like to watch their little bottoms twinkling as they scurry into the bathroom. If I like her I will ask her back. Then I have the very pleasant anticipation, knowing what she can do, having seen it all up very close, and knowing that shortly it will all be mine. But I do have to admit that sometimes the shoot has been so highly charged that I can’t stop myself, and off come the clothes and the model has a little extra work to do. It seldom takes up much of her time! I think the point I have made before about not having sex with the models has referred to the fact that I never stop a photoshoot simply to gratify myself. I’m actually quite a self-disciplined person, believe it or not. Whatever does happen, happens after.

The Sargent´s TAKE: The Captain DOES fuck his models during the shoots (but not nearly as often as I would!).
8.Is there any sex act you would do to a ladyboy that you would not let her do to you and vice-versa?
captain outrageous, shameless
No. I have always maintained that if you like someone enough to take off your clothes and get into bed with them, then acting prim and proper and saying “I’m not doing THAT” is not really acceptable. I used to make the same case to the genetic girls I went to bed with, the English girls mainly. I might just as well have been talking to myself. Sex is as much about pleasing your partner as it is pleasing yourself. I have done pretty well everything. Do unto others as you would have them do unto you, and so on. I would hate to think there is an experience I have missed.

The Sargent´s TAKE: Over the years, the Captain has taken the equivalent of one case of beer in ladyboy semen and the length of a horse racetrack in ladyboy cock.

 9.  Although you must have been with, I can only guess, several hundreds of ladyboys you never mention any really wild stuff (group sex, girl and ladyboy sex, fucking the maid and/or her ladyboy son, crazy BKK nights, drugs, booze, fights).  Are you really a quiet type or is there a wilder part of your life you choose not to share?
captain outrageous, shameless
I went through some wild stuff with genetic girls a long time ago, with crazy nights in Bangkok and Manila and Jakarta and Hong Kong. Group sex and foursomes and twosomes and sessions with lesbians…and there was the time in Manila when a furious girlfriend set fire to my hotel room…but I digress. Somehow I don’t feel the need to do that with ladyboys. The intensity of having sex with one ladyboy is something to be savoured. Often two together. But if I was going crazy, then I would miss the intensely erotic experience. A beautiful ladyboy or femboy is for me an incredible high. No drugs, I’ve never touched them, never even learned how to smoke ordinary tobacco. Booze, no, I’ve done my bit in the past to support the breweries, distillers and vineyards, but my system rebelled at some point and nowadays the stuff just sends me to sleep. As for my maid, you have never seen my maid!

The Sargent´s TAKE: The Captain didn´t deny he fucked the maid´s ladyboy son… I KNEW he had done it!…

10.On a deeper existential level is the ladyboy addiction a blessing or a curse?
captain outrageous, shameless

I would say it is a curse. It means that I am shackled to Thailand. I could go elsewhere, to the Philippines or Indonesia or South America, but I think that Thai ladyboys are simply the most beautiful. Also, as I speak something of the language and have a little understanding of the culture, their world is open to me to a degree that it wouldn’t be if I was somewhere else. In another ladyboy country, I would be just another john.

The Sargent´s TAKE: The Captain´s curse would be a blessing to most of us! Thanks for the candid answers! Long live the Captain!

School daze

captain outrageous, ladyboy prim

A cute young model arrived for a video shoot last weekend wearing her college uniform, having come straight from Saturday morning classes.

“You want me to get changed?” she asked, showing me a small bag into which she had packed a brightly coloured top and some shorts.

No! I said. You look perfect the way you are!

But I did give her uniform the once-over before we started, to make sure there were no distinguishing badges or other marks. The buttons had a school logo, but that wouldn’t be visible in a movie. I also reassured her that I have long ago blocked the site from being accessed within Thailand, so none of her teachers or schoolmates would see it.

Anyway, she was happy enough, although very shy and nervous, and we did the shoot.

Ladyboys turning up in their school uniform happens with surprising frequency. As I have written before on this site, there are now so many ladyboys attending schools and colleges throughout Thailand that the educational system makes allowances for them, providing them their own toilets and changing rooms and letting them wear the female uniform.

Often they cut classes to come and see me, or they come straight from school, tempted in by the chance to earn some easy money and to have their photograph taken.

There is a standard university uniform in Thailand, that only deviates in its detail. Girls wear white tops and black skirts, boys white shirts and black trousers. Badges and buttons distinguish the various institutes, and sometimes a necktie. I do have hanging in my props cupboard a number of uniforms, including uni uniforms, but very often the model you see on the main site is actually wearing her own uniform.captain outrageous, ladyboy prim

In the streets I frequently see ladyboys dressed in the female uniform. I have only ever seen them behaving demurely, and in fact in many instances it is only my super-rated ladyboy-detector vision that has picked them out as being ladyboys rather than genetic girls. Of course, they are under obligation not to let their school down, but the impression they give is that they have simply chosen the lifestyle because it seems natural to them, rather than being a revenue earner.

I had a heap of emails following my comments a couple of weeks ago on the youthful ladyboys of Buri Ram, and elsewhere upcountry, and of course very young ladyboys are also to be found in Bangkok. Eight-year-old fledgling ladyboys are not a great rarity. The fact that these youngsters are going through primary school, secondary school, and on to college or university in full ladyboy mode must surely be giving the educational authorities cause for much thought and perplexity.

Or maybe not. This is, after all, Thailand

The white stuff

I was with a particularly cute little ladyboy one evening during the week. She was straddling my chest, playing with her dick, when she suddenly shut her eyes and shot a load. Most of it went up my nose. “Sorry,” she giggled. “I didn’t mean to do that.”

I was just getting over a cold at the time, and the sudden infusion of warm cum made me sneeze. The funny thing is, that the next morning my cold had completely vanished. Does semen have any medicinal qualities, I wondered.

I remember a while back, living with a ladyboy who swore that semen was good for her complexion. She actually had beautiful skin: being from the Deep South, her skin was coffee-coloured and of a smooth and creamy texture. She avidly followed beauty treatment tips, and somehow got this notion that rubbing semen into her face each day would give her complexion an even more alluring glow.

It was pretty tough on me, I tell you. Each evening when I came home from work she would instruct me to lie down on the bed. Then, with her warm bare bottom in my face to provide some visual stimulation she got busy with her hand and within a very short period was smoothing cum into her face, in the same way she used cold cream, sitting in front of the dressing table mirror while she rubbed it into her skin.

For two or three nights she subjected me to the same treatment, kneeling over me and bringing herself off with a brisk hand, directing the hot stream carefully onto my face: because if it goes into your eyes, it smarts like the blazes.

I found that as it dried on my face, it gave a very uncomfortable feeling, as if I was wearing a mask, and that when I smiled or spoke it felt as if my face was cracking. So, after a while I demured. She, however, kept her own facials going for seven or eight evenings before staring intently in the mirror and sighing that it didn’t seem to make any difference. So we stopped.

But does it actually help your skin? I don’t really know. If you look at our movie section on the main site, at the movie I did of Bea and Dee, you will see Dee kneeling over Bea and about to shoot a load. Bea however giggles and says something, and Dee instead moves back and cums on her tummy. Bea is telling Dee not to cum in her face, and afterwards I asked her why. “Give me pimples!” she said.

One thing is for sure, however: it certainly can taste good. Much depends on diet, but a clean-living ladyboy (lots of vegetables and fruit, little meat, no alcohol, no smoking) can deliver a warm, creamy, nutty flavoured load that really is quite addictive.