Noi has all the aura of a female, and if you saw her in the street you would assume she was a girl. She is slightly built with a firm body, yet has the softening and cushioning of the skin that hormones induce. Her skin is almost completely blemish-free, and is soft and hairless. Her bottom is one of the most beautiful I have seen this year, being soft, smooth and creamy in texture.

Her cock is firm and has a cute little curve to one side. Despite the hormones it sprung into action immediately, and a glistening little dewdrop appeared on the end. It took her a while to cum, but she is a horny little minx. The kind of overt sexuality that sends hot shivers up and down your spine, and elsewhere. “You suck my cock now, and I cum very quick, sure.” Yes, well, we have all heard that one before, haven’t we. She got there in the end. What a lovely mess she made.

I had just returned from an overseas trip when I shot her pictures, and had been starved of ladyboy company for ten days. At that moment, if someone had put Noi in front of me together with an identical female Noi, I would without hesitation have chosen the ladyboy Noi. And that is from someone who has no problems whatsoever with women.

Of course, this is not the first time I have given thought to this, and have mentioned it before on this site. It is just that every now and again I find a ladyboy who is so utterly gorgeous, that I realise GGs so often trail a poor second.

I was talking over the weekend to a friend, and he casually mentioned his new girlfriend. “Female?” I asked, knowing his liking for ladyboys.

“No,” he replied. “Ladyboy. GGs just don’t do it for me anymore. I’ve finished with them.” I have a couple of other friends who say more or less the same. And the theme of any conversation with them is, that they have no interest in the gay scene or in males: it is only the ladyboys.

As for myself, even after all this time, I find ladyboys to be a continuous adventure. Many of them I photograph are brought to me, sight unseen, and I often never know quite who is going to walk through the door. On occasions I am disappointed. On other occasions, I am unmoved. But the Nois of this world, the Annabelles, the Pinkies, the Yings – all recent discoveries – leave me almost breathless with excitement. The same sort of feeling I had when I was a teenager. In those days, girls were almost untouchable. But ladyboys…well, they come looking for you.

There are a few hotels where I know I am reasonably safe, as I have used them for years without any trouble, and the staff know me. I’m a generous tipper under such circumstances. There are also a few apartments, one of them being in a riverside tower block, and featuring a particularly spacious balcony with a 180-degree view of the river and the street 15 floors below.

For a long time I used this balcony as a setting for the photographs, devoting the first part of the set to shots there before moving inside. In the end I used it too much. Even I realised that, but it was only when Webmaster Spike suggested that if he saw another balcony set he would throw me off it that I decided with reluctance to stop venturing out there with ladyboy and camera.

But it was a splendid setting. And it was also interesting in that it brought out the personality of the ladyboy I was photographing, for their responses to posing provocatively on the balcony were many and varied.

First, there were those who took one look at the unaccustomed height (Thais are not high-rise creatures) and declined to even venture out of the room. Then there were those who were convinced that, as they could see the entire world, the entire world could also see them. In vain I would argue that we were overlooked by no other buildings, that the nearest tower block was a hotel a mile or more away round the bend in the road, and that I had been on the ground level myself trying to see if I could see what was on my balcony, and that I could see nothing. It was simply too high up. The angle was wrong unless you moved a long way back along the road, by which time anything going on there was simply too small to see.

Then there were those who would stand in the shelter of the 6ft high potted fern and gently ease their pants down, which I always used to find pretty exciting. I got many good sequences with that type of model, particularly when the lighting was such that dramatic shadows of the fronds were thrown across wall and girl.

Best of all though, and I have to say these were pretty rare, were the ladyboys who would prance out onto the balcony, completely naked. Cherie was a master of this particular form of exhibitionism, always willing to display her gorgeous little body to the world in general. And taking shots of Cherie, and the others who pulled a similar stunt, was enormously exciting. The fact that they were there, totally naked, with life going on behind them unseeing and unknowing, was a big turn-on for me.

When you think about it, exhibitionism is what it is. We all, I think, have this tendency to want to do provocative things in public. Especially if we know we are safe.

Ageing is a problem that ladyboys face more acutely than anyone else. I see them in extreme close-up, and I can usually work out roughly how old they are at first glance, before I even check their ID. Female hormones will of course distort the appearance in some ways, plumping out faces and bodies and keeping the skin soft and supple, but I can usually tell when the ladyboy before me is 25, rather than 22, and certainly 18. This is especially so when the clothes come off. I very seldom photograph a ladyboy in the upper-20s age range. This is mainly through personal preference. I do know some of the older ones of 30 or so who have matured well, mainly through good genetics rather than any systematic attempts to stay young. But the bloom has gone, the sexuality of a young ladyboy beginning to realise just how desirable she is, and the mature person standing before me will look a lot different to the way she looked ten years previously. But by that age anyway, many ladyboys have removed themselves from the scene. They have gone past the stage of working in the bars and have graduated to either being taken care of by a regular partner or have gone into business, gone back upcountry, or joined a cabaret, which tend to prefer the more seasoned and reliable types, rather than the youngsters who will disappear at the slightest chance to make more money.

If they are cabaret performers, then their free time is limited, with evening shoots usually out of the question, and although I have taken photos of many cabaret girls, they have generally arrived late in the afternoon and been in a great rush to get to the theatre in time for costumes and rehearsals. So, when you go to see a ladyboy cabaret in Thailand (and I do recommend it as hugely entertaining, although almost entirely free of sexual innuendo), be aware that these are mostly mature ladyboys, more so than those you will meet in the go-go bars such as Cascade and KC3. I am sure that Honey will do well at the Samui cabaret. She has always been a cabaret performer, but usually it has been with travelling shows, of which there are many in Thailand. Often I have received a call from her, sounding full of fun, telling me she is in Phuket or Hua Hin or out in the sticks somewhere taking part in a friend’s travelling show. She is a natural mover, and being about five-seven in height and very slender, I am sure she will look fantastic on stage.I asked her why she is moving to Samui. She told me she has no money, and that in Bangkok she was finding it difficult to get regular work. Because of her cabaret work over the years she has plenty of contacts in the business, and when the offer came up to go down south, she took it. She told me that she wants to have a boob job done, and to try and save. She can do this by working in Samui. I’m going to miss her.

“Hang on, hang on,” I said. “Not yet! I’m not even holding the camera.”

I explained to her that I needed to take shots of her clothes coming off, as that was very sexy, and once that was done she could do whatever she felt like doing. She gave another little smile, and tugged her pants and shorts back into position.

Ladyboys are not shy. This is part of their appeal. They will peel their clothes off without hesitation (it helps if money is involved, of course) and stand starkers in your home or your hotel room, waiting for you to do whatever you want to them. And if you are holding a camera, that (a) gives you even more authority, and (b) makes them even more provocative.

This particular model was a little bundle of energy. We quickly reached the point where her pants were off again, and she turned and parted her bottom cheeks, giving me a spectacular view of a very inviting little opening. Yes, I did manage to keep taking the photos, thanks. Then grabbing her cock she shot a great wet load in about sixty seconds flat, and lay back with her eyes closed. Clearly, she needed that.

Even the shyer ladyboys have no qualms about undressing in front of me. They arrive looking a little bit scared, but my assistant Ek has already reassured them I am not a monster (hah!) and the first few minutes are spent putting the model at her ease. A glass of water, a chat about where she comes from and what she does, a couple of jokey comments…anything to relax her. Then off we go. By the time the session is finished, we are on very friendly terms. I have watched her do the most intimate things. She in turn has been treated with respect, had a bit of a laugh, and earned some money. Although I have on occasions dealt with models who have been surly, I have never, as far as I can remember, ever had a bad session. Never had to stop and cancel a shoot, never had an argument.

But to return to this lack of shyness about undressing. Ladyboys will undress in front of me with no hesitation whatsoever. But they are scared witless at the thought of being seen naked by their friends.

During the week I did two shoots back to back during the course of an afternoon. Both the models were from Cascade, in Nana Plaza, and they knew each other. The first one came in while the second one waited with Ek in the food court area of the building. After we had done the first shoot the model went into the bathroom to shower and, I thought, to get dressed. So I called Ek and he arrived with the other girl, just at the time the first one was emerging completely naked from the bathroom. She had in fact left her clothes in the bedroom.

It would be difficult to say which of the two girls was the most embarrassed. The naked one almost went into hysterics. This however was a girl who during the preceding hour had undressed in front of me, got onto her elbows and knees so that I could photograph right up her bottom, played with her dick in the most tantalising manner, and then wanked off and spurted cum all over herself. Not shy at all. And of course both girls were no doubt perfectly at ease wandering around in Cascade dressed only in skimpy bikini outfits, acting in the most provocative way possible to entice customers into taking them out for the evening.

This fear of their friends seeing them naked extends to the photographs. A model will quite happily stand naked next to me while I show her her own photos on the screen, but if she has a friend about to come into the room for a shoot, will ask me please not to show her friend the pictures. I was playing a video back to one of my recent models while she was standing, fully-clothed, watching with satisfaction. When a tap at the door signalled the arrival of Ek and the next model, she flew into a panic. “Not show, not show!” she gasped, waving her hands at the screen. I closed the video. I’ll go along with it all. I rather like them modest, to be honest.

I expect the Captain will write something at the end of this article. The fact that in this here blog I am just a Sargent does not mean I feel less authoritative than the Captain about all aspects of ladyboy warfare. So, today I would like to talk about ladyboys’ first sexual experiences and let’s face it: the fact that I, unlike the Captain, don’t live in Thailand means that when a ladyboy falls into my lap (at 18 years of age or older definitely) she probably has been passed around quite a bit among the natives, the expats and the sex tourists.

Yet, more than a few times I have been with ladyboys who said I was their first. What could they possibly have meant?

The first possibility is that they literally were virgins and I was the first man to anally penetrate them. This is highly unlikely and not many have tried such a lie on me. Becoming a ladyboy invariably involves some degree of gay experimentation in adolescence and boys being boys a sweet accommodating girlie ass does not likely go unporked through prep school. If the Thai prep school studs do not get it first, it is highly likely that their older countrymen who are cunning (and btw much more predatory than the expats) will buy, cajole, or force their way into an effeminate boy’s backdoor. In brief, by the time the girlie boys reach the ladyboy bars and seafront boardwalks, the chances of them being virgin are next to nil and, even if they are, it would by definition all be over after the first full-service customer.

Having said that, I may have on a couple of occasions been the first to break a sweet ladyboy’s rosebud. It is a fact that some ladyboys refuse anal sex under several pretexts. I myself have been told my cock is too big, it is against their Buddha, they have diarrhoea, or they were saving it for their true love. Most of the time these were excuses to avoid the pain or subservience of taking big farang cock up the poop chute. Being the creative type, on such occasions I satisfied my lust in different manners but I also managed to persuade a few of them to surrender their treasure. I knew most were lying about being virgins in the first place, but a few (who were not bar workers or streetwalkers) may have been.

With a greater degree of certainty, I can say that I have made it possible for several ladyboys to lose their virginity as tops. Again, some may have been pretending, but I believe a few never had a shot at topping anyone as nearly all Thai men and many farang consider it not macho to allow insertion and also ladyboys like to live up to their female illusions by being strictly passive. I remember a ladyboy who had worked in KC3 for a couple of years telling me she was a lady and would not be able to top anyone, but after I proved her wrong she saying with what sounded like genuine satisfaction how good and easy it was.

And even with greater certainty, I think that by “first” the ladyboys were saying that I was their first farang. In fact I am pretty sure this was the case as, on most such occasions, I had met them in non-tourist venues, and nothing in our interaction indicated they had been with tourists or expats before. I like to believe this was what they meant by being their “first.” But as regards getting to ladyboys first, the Captain with his decades on the prowl in Thailand is probably the leading authority on the subject. The final word is yours, Captain.

A ladyboy can be whatever you want her to be! They are after all living a life of illusion. I would hesitate to say that ALL ladyboys tell you what they think you want to hear, but it’s a fair bet that those working in a commercial setup will. There is also, as you rightly say, those who are afraid to do it because of the pain or the risk of physical damage, or who may be recuperating from a previous log entry, or simply have a dose of the runs; the latter, with Thailand’s spicy food, being a non-infrequent condition. But, Sarge, a little visual inspection, and possibly a cautious fingertip, will give you a pretty good idea whether or not your beloved of the moment is joshing you. The back door to paradise is surprisingly small. Despite what many people seem to think, it was not designed to take a big cock. A genuine ladyboy virgin will have a very tight little opening. It will look small and smooth, with minimal puckering, and the inserted fingertip (or, better, tongue) will detect the tight little ring of muscle that is the sphinchter. Once our ladyboy friend has acquired a taste for being rogered, the appearance of this gorgeous little hole changes. The puckering becomes more evident, the opening takes on an appearance akin to a tied balloon, and sometimes you begin to see tiny little bobbles (or worse) where the skin has been stretched or damaged. As for the ease of entry, with the more experienced girl and a spot of lubrication, it becomes nearly as easy as vaginal sex. I have seen countless ladyboy bottoms up really close and intimate, and I’m pretty confident I can spot a virgin (or near virgin). As to being a virgin at the other end of things, all I can say is that it only hurts the first time! And those who decline, usually for purely macho reasons, are missing out on one of life’s great experiences. Forget the conventional squeamishness. You are with a girl who has a cock. The rulebook goes out the window.
- Captain Outrageous

“It is toward the south end of the road on the side farthest away from the beach. As you travel south along the middle road you will see on your left an orangy coloured building with Loma Massage written on it, take the next left after that and Tootsie Massage is tucked away in this cul-de sac. They usually have five or six girls to choose from.”

It’s been a couple of years since I was last in Phuket, so I’m a bit out of touch with the ladyboy scene there. But I googled the name, and found that Tootsie has its own website . They feature pictures of some of their girls, and they really have some lookers. Time for a visit, methinks.

Maybe Tootsie is the vanguard of a coming wave of ladyboy massage parlours. In my previous post I went on a bit about the economics of such a place, and while it might be a costly concept in Bangkok, it might well be more feasible in Phuket or Pattaya, where the rents will be cheaper if you are away slightly from the beaten track.

For a massage parlour to make money, you need volume. The massage process takes, say, an hour. It also takes up a sizeable room, so you need a largish building. The system works with GGs, and on a smaller scale with gays. But as to having a ladyboy massage parlour, maybe the economics simply does not stack up. Maybe there are just not enough customers. Yet.

A massage from an energetic ladyboy is certainly a thrilling experience, if organised at home or in the hotel. Not that long ago I had a regular ladyboy visitor who liked to join me in the bath, and rub her soapy little body and hard cock all over me. Another liked to give me a dry body massage, using her own body, which was exhilarating but didn’t last long because I would soon feel a hot damp patch spread over my stomach or back, at which point she would collapse upon me with a giggle and a sigh. True, I didn’t get much muscle relaxation, but she did point out, as she rubbed her cum into me, that it is good for the skin.

Yet another had a very neat line in sitting, carefully, on a very sensitive part of me, with her back to me, and giving me a massage with her bottom. Those sessions were quickly over too, although I was the one who was first to cause the damp patch.

And yet another would walk along my spine while I lay face down on a mat. She was an expert masseur, having gone through a course in her home town, and she was so light and well balanced that what might sound like a worrying experience was in fact a restful one, with her feet warm on me and her toes kneading my back. The first time she did it, I rolled over after she hopped off, just in time to see her with an evil grin take hold of her cock and spurt hot cum over my face and chest. Little minx.

So when you think about it, a massage from a ladyboy has more possibilities than a massage from a genetic girl. The only drawback is, that one ladyboy would only be able to service a limited number of customers in one night. So, if you are going to visit Tootsie, I would recommend an early start.

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 capacity 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.

Next ladyboy into the room (I often do two shoots back-to-back) also produced a fairly unimpressive specimen. Until she began wanking, when it came up big and hard and the head of it turned a bright red. A lovely sight.

The beauty of the penis is something I have gone on about many times (many times!) before on this blog, and even now after seeing heaven knows how many in all their various shapes, colours, sizes and stages of arousal, I still wait with breathless excitement to see the next one. Yet these are all ladyboy cocks. Not guys. It takes the aura of a girl coupled with a cock to do it for me. Not the male aura.

Something very funny happened during the week. I was with a genetic girl, a very good friend, and we had met up during the early evening to have some food. She arrived looking very indignant. She explained that on her way, she had walked past a bus stop where there was a solitary male, a company messenger, who was sitting on the bench giving himself a hand-job. Completely alone, cock out, oblivious to the rest of the world, and obviously enjoying himself, as my friend dryly put it.

I asked if he looked a bit simple-minded. You do find a number of disturbed individuals wandering around Bangkok, sleeping in bus shelters, under footbridges and in doorways, and occasionally doing some distinctly unsavoury things.

No, she said, he was dressed in a smart messenger uniform with the company logo on the back. She had been so indignant she had walked over to a nearby motorcycle taxi rank and told one of the drivers, who had gone to sort out the happy wanker at the bus stop.

As she was telling me the story, I was checking out my own reactions. I found the story genuinely funny, my friend’s own purse-lipped reactions being part of the comic effect. Then there was the word she had used for masturbation when she spoke to the motorcycle taxi driver: “chuk wow”, Thai slang for wank, and which actually means “fly a kite.” She said she didn’t think the driver would understand anything else.

But, even though I came close to tears of laughter, my own underlying feeling was one of repugnance. No, I would not have been in the slightest bit interested in catching a glimpse of the messenger’s cock, or of watching him come to a satisfactory conclusion and spurting all over his nice uniform trousers. No, I would not have felt the slightest inclination to go and give him a hand. The very thought gave me a queasy feeling.

How very different when I go into a bar like Casanova or Pinocchio, where there is decent seating, and admire the cock that one of the more obliging ladyboys will produce while I sit there. How very different when a ladyboy lays on my bed or sofa and gives herself a hand job. How very different when I myself take hold of her dick. Is it just the makeup that does it for me? The female clothing? No, it’s more than that. It’s putting a cock onto a girl. One of the ultimate fantasies.

It’s a phrase I hear fairly often on my travels amongst the ladyboy community. The fact is, I didn’t. The girl standing in front of me was mid-twenties, and clearly had an awful lot of silicon in her face. Her eyes glittered deep down amongst plastic cheeks and forehead, and her nose could have opened a bottle of beer.

Yes, I replied politely. But I haven’t seen you for a long time…

“Two year,” she replied. “You photo me two year ago!”

Two years is a long time in ladyboyland. For me, it means a lot of people being photographed, and a lot of personal encounters. For the ladyboy in question, a lot of adventures I would rather not know about, and several changes in appearance so that she will bear little resemblance to the girl I photographed all that time ago.

To be honest, I did not remember her at all. There is a certain ladyboy “look” that so many acquire through going to the same clinics and undergoing the same operations. I remember seeing recently a picture of Hugh Hefner with three of his current bunny loves, and the girls all looked exactly the same. Like clones, or blow-up dolls. Sometimes, with ladyboys, it is just the same.

So we started the shoot. Plastic boobs, no, they didn’t seem familiar, and quite frankly I find plastic boobs as exciting as party balloons. But then down came her pants. Her cock, despite all the hormones, stood out straight, with a bit of encouragement. As her foreskin slid back, I remembered. There was a small freckle on her glans. Nothing odd, nothing freakish: just a tiny brown patch. And yes, I remembered that from the previous shoot, because it was unusual, and I’m always fascinated by the shape, size and colouring of cocks.

Whatever you do to your face, you cannot change your cock. Unless you opt for a circumcision, or you have the thing cut off entirely.

I even remembered that she was able to cum. I simply remembered that freckle jigging about, and then a nice covering of sticky white semen. I do like to watch ladyboy cocks in all their glorious forms, and as so many are standard-issue, those that are a little different, even in having a small freckle, do tend to stay in my mind.

So this time I watched, and after much tugging, gasping and grimacing, she came. It was pretty good: despite the hormones, she still managed a neat little spurt and a sticky puddle in the palm of her hand.

Later, I went back and found that original set. My memories of her cock and its freckle were pretty accurate. In fact, there were some good shots there. But as to her face, I could see very little resemblance.

I watched as she sat there gasping. She had splattered up under her chin, all the way down her front and into her tummy button, there was a long trail over her left hip, her pubic hair was glistening, and the sheet had little wet patches extending outwards for a couple of feet.

Well, that was pretty impressive, I said. But you don’t normally do that well. What have you been up to?

“I not take hormones long time,” she said. “Before, cock not strong. Only cum little bit. Very difficult too, sometimes not cum at all. Customer at bar not interested me. Friend tell me stop take hormones. So I stop and about one month after I feel very strong again. Now have many customer, many come back take me again.”

Clearly her friend had given wise counsel. I have known my ladyboy friend for a long time, ever since she was a shy 18-year-old, creeping into my bed and laying with her dick in the air, putting her hands across her face in sheer embarrassment. It had not been a big one in those days, and I took it now in my hand, feeling the strength in it, the weight, the fast response of a cock in its prime.

It was never this big before, I said. You must have done something to make it bigger.

She giggled. “I exercise! Chuk wow every day!”

Chuk wow is slang for wank and it translates as “fly a kite”. Thai slang can be very colourful.

I really don’t know if repeated masturbation when you are in your teens causes your dick to grow bigger. If it did I would need to have special trousers with three legs. But the size of my friend here had certainly increased noticeably.

I was very pleased she was off the hormones. They do not suit all ladyboys. It had been about six months since I saw her last, and I had straight away seen that she had a glow about her, a little more confidence in the way she carried herself. That, I think, was down to the resumption of normal bodily functions. No matter how feminine a ladyboy may feel, there is the undeniable fact that she is biologically male and that having a fully working cock is part of the male package.

I have seen what hormones can do over the years. They can produce a very feminine ladyboy, able to pass anywhere as female, and good luck to those lucky ones. But on others, the effect, even taking out the dick factor, is not so good. Sometimes you find a kind of over-egged effect, in which too much fat builds up in the face and body, resulting in a lack of tone. Sometimes you find mental instability, as the hormones and nature clash. It seems to be a kind of lottery.

There is the undeniable fact, however, that for a man going with a ladyboy, the ideal is a feminine person with a strong cock. To my mind, femininity (in ladyboy terms) comes down to good makeup and grooming, polite manners, soft speaking voice, and decent clothing. Once you have these qualities, and add in the final alchemy of making the male aura disappear, then you have your ladyboy.

I am of course speaking in entirely selfish terms, because generally speaking, this only holds good for the young ones. Someone intent on entering the female mainstream might consider selling herself to be only a short-term way of earning enough money to become independent and to open up a small business; the dream of many ladyboys. She might think hormones are essential for her objective, and hope that by the time the hormones have done their deadly work on her dick, she will be home and dry in terms of savings.