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Archive for December, 2010

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!

The mechanics of masturbation

captain outrageous, ladyboy apple

It really cannot be that easy, wanking off while someone is standing over you with a camera. That thought occurs to me from time to time, as I stand hunched like Quasimodo over a ladyboy who is pulling and pulling at her cock, trying desperately to reach the elusive point where the reflex is triggered and the semen starts its way through the plumbing system.

“Daeg lao!” she might utter, which translates as “broken now” and I concentrate hard, waiting for the spurts of white cum that will follow over the next few seconds.

But, as I say, it can’t be easy. Especially if the ladyboy in question is taking hormones. Especially if she has spent all night with a demanding customer who is enchanted by the fact that his “girl” can cum more times than he can. Especially if she has no stimulus, and here I often get asked if I have any gay magazines in the house that she can look at to get in the mood. I don’t. It doesn’t occur to me to buy gay magazines, until I get asked by a ladyboy trying to get her dick up and running, and then I think, must do that later. Then of course I forget.

When you are shooting as many photos and videos as I do, you become very finely tuned to the mechanics of masturbation. I can look at a flaccid dick and think, yes, that one will work fine; or, no, that is not going to do very much. I’m not always right, of course. But then again, I’m not often wrong.

I watch very closely, trying not to be too off-putting, as she works herself up to a good hard one. And as she progresses, it is not just her cock that I watch for the signs, it is her body language: the curling of the toes, the movements of her feet, the twitching of her legs, the rippling of her stomach muscles, the biting of her lip. Sometimes the head of her cock will change colour shortly before the spurt. Sometimes, a cock will lose some of its hardness just before shooting: with others, it becomes even bigger and harder. Sometimes the pre-cum will signal the moment, with that inviting squelchy sound made by fluid and foreskin.

Then there is the magnitude and volume of the spurt. Sometimes I am awed by the white fountain and the flying droplets. Or it might be a thin jet, hitting nipples and chin, or even a fine spray, going over tummy and thighs and bed sheets. Other times it is simply a pumping out of thick white fluid onto black pubic hair and brown tummy, and that’s fine by me too. But hormones will reduce the amount and the whiteness, so that maybe it’s only a colourless trickle, or maybe an oozing up of a very small volume, or even just a slight stickiness that I don’t immediately notice, especially if it has emerged into the palm of a hand. 

But sometimes, even I get bored. Especially in the case of shooting a video, and the wanking session goes on and on. I don’t dare relax, because if I missed the event I would spend the rest of the day kicking myself. Afterwards, I sit at the computer and look back at the long minutes of not very much happening, except for the frantic pulling and pumping. Sadly, I discard most of it except for some exceptional clips or angles or facial expressions.captain outrageous, ladyboy apple

Last weekend I was shooting a video and the model had been working her dick especially hard. Eventually, she stopped. I looked at the poor, reddened thing lying on her tummy. I think you had better have  a rest, I said, and put the camera down. She played listlessly with her cock for a couple of minutes, and it came back up hard. Then with a couple of swift hand movements, while I was still scrambling for the camera and the “on” switch, she came. Not much, but it was something. I just about caught it. 

That was easy, eh? I said. She gave me a sweet little smile. Then she fell asleep. I left her there in bed for half an hour. She  had worked hard. She deserved a snooze. 

Bib and tuck

captain outrageous, ladyboy cherie

I watched a ladyboy wanking off this afternoon, and when she had finished, as she leaned against the wall gasping, I told her with genuine admiration that she had a big cock. I suppose it’s because you exercise it every day? I said.

“No,” she replied, earnestly. “It’s because I have to pull hard every day and tuck between my legs. Lot of ladyboy have same problem.”

I was a bit doubtful about the pulling having any effect on dick length, but she did have a point about the tucking away. Ladyboys have to do something to hide the bulge. Imagine a ladyboy bulging out of tight jeans, or suddenly experiencing a tent-like erection in a cotton frock. Well, personally, I like the idea: but of course it would rather spoil the illusion that the ladyboy was all girl.

I’m not sure if KC3 still do so, but in years gone by they would always insist that their dancers tape their dicks well back between their legs so that they didn’t suddenly stand up and burst out of their pants while on stage. This was very unattractive, because the sticky tape left a residue. Time and again I would have someone turn up for a photoshoot and I would discover tell-tale traces of sticky tape. You work at Bar King don’t you, I would say.

“Yes! How you know?”

The residue was often almost invisible, but the studio lights pick it up and it’s a real nuisance. Difficult to remove, too. Often we would stop while I applied soap and water and then scraped it away with a finger nail. But that didn’t work too well, and it was easier to get rid of the marks later on screen, using Photoshop.

If you look at a naked ladyboy from the rear, when she has her cock tucked up between her legs, the effect is rather startling. A good big one will be staring back at you from directly beneath a cute little bottom, and as soon as you reach out a tentative hand to stroke it, it will vanish and swing up into the action position on the other side. Quite good fun, actually, on a lazy weekend afternoon.captain outrageous, ladyboy cherie

Some ladyboys are so adept at this trick of pulling their cock back between their legs that they produce a neat little dimple that looks for all the world like a pussy. I remember one girl who could do this very effectively, and she would stand in the mirror admiring herself and saying, “I just like lady, yes?”

Well, she was until I gently ran my hand down her bottom and gave the protruding length a gentle squeeze, whereupon of course the serpent would release itself and rise up in front of her. Some lady, I would tell her. I thought you were a real girl. Cue helpless giggles from my friend, and an irresistible urge on my part to get her to shoot a load, by whichever means were uppermost in my mind at the time.

I’ve said it before…real girls can’t do that.