the third sex

My current little sweetie is incredibly shy, and nervous about doing anything too adventurous. I really do like her, so I’m being cautious. But she really is, I’m sure, a virgin. I think at some point it will be time for a particularly large dollop of KY, but I do like a neat, tight, tiny little hole to play with. I was unwise enough to mention this to Sargent Shameless the other day, and as a response he sent me the following.

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

Early 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 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.

She sat on the end of the bed, cock in hand, and within a couple of minutes the room was filled with the pungent aroma of hot cum, that odd mixture of fresh coconut juice and household cleaner.

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.

“What you think?” asked my ladyboy friend, hand on hip and turning her profile towards me. She had had a chin augmentation job done. Actually, it wasn’t bad. She looked fine. But many ladyboys who opt for cosmetic surgery make a sad mess of themselves. And some of the older ones look grotesque, because they fill their faces full of plastic when they are younger, and they don’t know when to stop. As they get older, parts of their face change: other parts don’t. Bangkok is renowned as one of the world centres for cosmetic surgery, and there are some fine surgeons here who will do a good job at a rate far below those charged in the West. But there are also a lot of slash-for-cash merchants about, and their rates are even lower, thus attracting the kind of clientele that has high hopes but not too much in the way of money.

Not that long ago a young ladyboy friend of mine who had a sweet and perfectly symmetrical face went for a chin job. Heaven knows why she did it: it wasn’t needed. She came out looking like Desperate Dan. It did nothing for her at all. Even worse was the ladyboy I knew some while back who had a chin job done that left her with a square chin that jutted down from her face in the shape of a short beard. And the one who wanted to make her face heart-shaped, and had a pointed chin added that was so badly done you could see where it joined up with her face.

Everyone wants a nose job, whether they need one or not. The people of Issan, who probably produce the greatest number of ladyboys, are rather self-concious about the ethnic characteristic of the squidgy little nose. There is very little bone or cartilage in the Issan nose, which tends to be flat. Women and ladyboys alike have nose jobs done, and it forms one of the staples of the cosmetic business. The routine surgery involves squeezing an off-the-shelf pre-formed plastic bridge up a nostril, with the result that a lot of Issan people are walking around with the same nose, so to speak.

So I see a lot of ladyboys who have had this operation done. Others who want a custom-built job will pay more money, of course, but some of the results I have seen have been frankly a disaster. Yo, who appears a few times on the main site, had the sweetest little feminine face. Then she had a nose job and a chin job that, in profile, made her look like Mr Punch.

Some ladyboys are simply never happy with their appearance. Anny, an early model, went through six noses. Somewhat alarmingly, she had one of them damaged in a minor accident just before she and I were about to leave for Pattaya. It had simply been a slight knock when she was larking about with a friend, but the transplant was dislodged and over the next 24 hours became very painful. We cut our visit short, and hurried back to Bangkok so that she could visit the clinic. I think that had been nose number five.

Another ladyboy friend, whose big eyes and clearly defined eyebrows gave her real beauty, managed to make a mess of herself by having cheekbone augmentation, which distorted the shape of her eyes. Just to finish the job off, she plucked her eyebrows. She just did not understand that she could have enhanced what she had, rather than change everything.

I won’t even get onto the subject of boobs, except to say that I have seen (and felt) some that are so hard that they stand out like water melons, and others where the sacs have been inserted so badly that the nipples point in different directions. I am still haunted by the memory of a ladyboy friend who turned up one day with only one breast. The other had started leaking, and the doctor had whipped it out. This was a ladyboy for whom I really had the hots, but on that afternoon I was struck impotent.

I could go on…the craze a few years back for vampire teeth…the startlingly blue contact lenses that occasionally confront me…lip collagen jobs that create a trout-like effect…adam’s apple reductions that leave the voice a hoarse whisper…it is all very unsexy.

My old friend Jodahunta was recounting some of his experiences in the bordellos of South America, where he says the number of those specialising in transsexuals is increasing. I asked him if he would be kind enough to pen a few words for the blog, and this he has done, with relish. Here is his account.

One “burdel”, many “burdeles” (Spanish) = bordel (French), or in English: brothel, whorehouse, cathouse, knocking-shop and endless other terms. They’ve been around for a long time, as you would expect for an essential aspect of the world’s oldest profession. Wikipedia says that they were recorded in Sumeria (wherever that was) 4000 years BC! Most countries have them in one form or another, legal or illegal. In Europe they are legal and regulated in Holland and Germany. Paris had some internationally famous ones. They were called “maisons de tolérance” or “maisons closes” (because the shutters were always closed) but France banned them just after the war for collaborating with the Germans (and getting rich in the process!)

Spain tolerates them. In the UK they are known as massage parlours. They are also legal and regulated in Australia where in Perth a certain Mrs Kenworthy, a distant relative of my late Scottish stepfather, operates one of the largest. Nothing dour about tha wee lassie …

In the US they are illegal except in Nevada, but only in towns with a small population. So none operate legally in Las Vegas…but I still found one! But NOWHERE in the world do they proliferate like in Latin America!!

From towns along the US-Mexican border like Tijuana, Juarez and Nuevo Laredo all the way down to Ushuaia at the tip of Tierra del Fuego there are burdeles in every city, town and even a good many villages!

In Central and South America it is just commonly accepted that a guy can drop into a burdel either alone or with his buddies, at lunchtime, after work or in the evening, have a drink and a fuck or a blowjob, and then go back to work or go home to dinner with wifey and kids, or whatever.

Back in 1993 I met an Argentine Assistant Attorney General in a burdel in Buenos Aires. At the time I was only just starting to learn Spanish but he spoke perfect English. We had drinks, discussed and resolved the world’s problems, partied with some girls and exchanged business cards. We stayed in touch for several years until he retired and I lost track of him.

Burdeles take many forms. The classic version is a saloon or bar where you can sit and have a drink, meet and chat with the girls, and then head off to a room in the back or upstairs and do your thing. Often these are very easy to find in designated areas of cities (ie nightclub/entertainment areas) or on the outskirts of town where at night you just look for the house with all the red lights.

In business and residential areas of cities and in suburbs they tend to be much more discreet, usually operating in apartments or suburban houses. You find them via print ads such as the classified section of newspapers or on the internet. They vary greatly in terms of quality, prices and services. At the high end you are invited into the salon area, offered a drink, meet and chat with the ladies, and can choose from a variety of theme rooms with amenities such as Jacuzzis. Once you have decided what you want to do where and with whom you have a discreet chat with the person in charge, pay your money and off you go. At the low end you are ushered straight into a small bedroom, the ladies are paraded in one by one, you choose the one you want and the time, usually 30 minutes or an hour, then you pay, play and leave.

But what is really special about Latin America is that you can now find “burdeles con traviesas”, or TS bordels. In some you will find both ggirls and tgirls, whereas others are 100 percent transsexual. They are by no means everywhere but you will find them in most major cities like Buenos Aires, Sao Paulo, Rio, Caracas, and Bogota. Also in the towns along the US-Mexican border.

Buenos Aires has been one of my favourite playgrounds for nearly 20 years and I found my first TS burdel there in 2002 through the classifieds section in one of Argentina’s leading national dailies. It is still operating and I am now a VIP customer and have my preferred room with a whirlpool bath. I was there just 10 days ago and spent a very pleasant couple of hours with a slim young blonde TS for the princely sum of US$50 + a US$10 tip to the girl.

But there are at least a dozen others I know about, some I have already visited and some still to be tested. And from time to time one will close down and another will open in some other place. Some are open 24/7 with girls working eight-hour shifts. Others open late morning and close around midnight. Usually these places have anywhere from two to six tgirls working at any time and quality and prices vary greatly.

Once you locate the burdel you want to visit from the print ads or the internet you call up and let them know you are coming over and give them your first name. If you have seen someone on a webpage who gets your dick twitching you can find out when she will be there and sometimes make an appointment to meet her at a specific time. Then when you get to the building entrance you call on the interphone and let them know you are there. Normally someone will come down and let you in once they have verified that you don’t look like something out of a Frankenstein movie.

You will then be taken to a room, sometimes offered a drink, then introduced to the ladies present and told about services, times, prices etc. There is no real “obligation to buy”. Not that often, but on one or two occasions, I have just politely said no thanks and left. If you reserved a particular girl you will usually be taken straight to the room where she is waiting for you.

In nearly all cases I have found these places are friendly and with a relaxed atmosphere. If you reserved a girl from her photo on the net but in reality it was somewhat over-Photoshopped and your libido suddenly takes a dive they will try their best to accommodate you with one of the others. And in those places I frequent more regularly I have never felt uncomfortable about having things stolen. But then again I have been to one or two where I had doubts about how often the sheets go the laundry but that’s the same the whole world over.
I have been to places where you get offered a 15-20 minute blowjob for US$10 but might hesitate putting your dick in the mouths of some of the ladies present, and others where you can spend US$75 + a tip for an hour of pleasure in a room with a Jacuzzi with a real stunner who has her own webpage. OK, that’s a lot more than you will pay in Thailand but still a fraction of what you would have to shell out in Europe or in the US for a visit to a tgirl who will probably try to hustle you out in less than half the time!

The average age of the tgirls I have encountered in these burdeles ranges from around 20 to 30. Thankfully I have never been offered anyone obviously under-age. Although there are some streets in Bs As where young tgirls of around 17-18 can sometimes be seen, I imagine the burdeles don’t want to take any risks in this respect. Most of the tgirls themselves come from the northern (and poorer) areas of Argentina or from Brazil or Uruguay and are ethnically usually of either European or mixed European-Indian (as in South American Indian) origin. Sometimes beautiful “mulatas” from Brazil, Colombia or the Dominican Republic can be found too.

And in case you wondered, all the oral stuff is usually “without” but safe-sex is the norm where anal is concerned, with lube and condoms always provided.