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Like a virgin

ladyboy pattaya
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.ladyboy

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. ladyboyBut, 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

Top to bottom

Ladyboys Talisha and Jessica

There is a model named Bang whose photoset I posted on the main site a couple of weeks ago. She is no beauty, if I may be ungentlemanly enough to say so, but she radiates an animal sexuality that stirs up troubling thoughts if you happen to be a natural top.

Bang is big, about six foot tall, and she has an enormous cock. When she first took off her pants it swung out and then stood out stiff and straight without the need for any encouragement at all. She is undeniably masculine in appearance, yet she has a femininity that sends out confusing signals.

The feelings she arouses are therefore conflicting ones. I suspect (I have no carnal knowledge of her) that a session in the sack might end up with a naturally top person being ravished: ravished by a six-foot ladyboy with the build of a wrestler, a cock like a full hosepipe, and a face like a tigress.

Sometimes you can’t control these situations, and Bang seems to be the kind of lady who doesn’t take no for an answer. If she happens to be bigger and stronger than you, you could without it having been planned that way end up bottom.

Where does that put our top person in terms of sexuality?

Reading the demented ramblings of Sargeant Shameless a little earlier on this blog gives some clue. He had spent a night with two spectacularly endowed ladyboys, during which he had been subjected to a close-up view of his pillow for much of the time, and had survived the ordeal with most of his pride attached. I’m not so sure about the rest of him. I know the Sargeant personally, and he is a very masculine kind of man. Yet he had no shame (well, he wouldn’t really, would he) about playing the bottom role.

The same goes for an Australian building contractor of my acquaintance, a rough diamond if ever there was one, but who is not too embarrassed to admit, after a couple of stubbies, that his ultimate excitement is to take it from a big-cocked ladyboy. “It’s only sex, mate,” he says. “Mind you, I can’t talk about this at home.”

This I think is partly the reason that so many guys feel guilty about going bottom: they can’t talk about it. They turn the possibility over in their minds, decide that it’s going just a bit too far in the wrong direction, and cry off. Yet if you can talk about these things, even anonymously, it helps to sort things out in your mind.

So if you do happen to find yourself prone under a large ladyboy, then I would suggest that far from being guilty about it, you should try it again as soon as you can. And also send your experience in to me, and I’ll be happy to post it here.

May we be excused?

Ladyboy toilets
Separate toilet
facilities for ladyboys have long been provided in many Thai colleges and universities, but seldom do you hear of secondary schools having transgender toilets for the pupils. This item has just appeared on the BBC website.

The comment from the headmaster as to the high proportion of transgender pupils bears out what I have been saying for some time now: youngsters are making the decision to become ladyboys at a very young age.

“With its spacious, tree-lined grounds and slightly threadbare classrooms, there is nothing obviously unusual about the Kampang Secondary School. It is situated in Thailand’s impoverished northeast, and most of the pupils are the children of farmers.

Every morning at 0800 they all gather outside to sing the national anthem and watch the flag being raised. Then they have a chance to use the toilets, before heading off the first classes of the day.

Kampang is proud of its toilets. Spotless, and surrounded by flowering tropical plants, they have won national awards for cleanliness. But there is something else about them too. Between the girls’ toilet and the boys’, there is one signposted with a half-man, half-woman figure in blue and red. This is the transsexual toilet, and outside, in front of the mirrors, some decidedly girly-looking teenage boys preen their hair and apply face cream.

The headteacher, Sitisak Sumontha, estimates that in any year between 10 percent and 20 percent of his boys consider themselves to be transgender – boys who would rather be girls.

“They used to be teased every time they used the boys’ toilets,” he said, “so they started using the girls’ toilets instead. But that made the girls feel uncomfortable. It made these boys unhappy, and started to affect their work.”

So the school offered to build the transgender boys their own facility, and they welcomed it. Triwate Phamanee is a slightly built 13-year-old who is adamant that he will one day change his gender.

“We’re not boys,” he told me, “so we don’t want to use the boys’ toilet – we want them to know we are transsexuals.”

Vichai Saengsakul, 15, agrees. “People need to know that being a transsexual is not a joke,” he says, “it’s the way we want to live our lives. That’s why we’re grateful for what the school has done.”

The transgender boys in Kampang tend to stick together as a group, practising their somewhat exaggerated feminine mannerisms together and generally camping it up. They still have to wear male uniforms, make-up is not allowed (although some manage to sneak in a touch of lipstick and mascara), and of course sex-change surgery is out of the question at this age – the youngest self-declared transsexual is 12.

But they appear to be treated perfectly normally by other pupils and teachers alike. I asked the headmaster whether they were not too young to be making decisions about their gender. He said that, in his 35 years of working in the Thai education system, he had come across many boys like this, and they never changed. Many go on as adults to have sex-change surgery, while others will live as gay men, he said.

Thailand is well known for its tolerance of transgender men, and they are very visible in everyday life. Sex-change surgery has become a speciality of the Thai health industry, and it is relatively inexpensive; patients come here from all over the world for the operation.

The Kampang school’s initiative, far from stirring up controversy, has instead prompted a discussion in other schools over whether they should be providing the same facilities. A ratio of 10 percent to 20 percent of boys calling themselves transsexual in a provincial high school does seem very high, but Mr Sitisak assured me that in his experience it was not unusual.

Which brought up a question that has been rattling around my head ever since I first lived in Thailand seven years ago: Why do so many Thai men want to become women?

I asked Suttirat Simsiriwong, who became a campaigner for transgender rights after she was barred entry to a nightclub at an international hotel in Bangkok last year. Poised, articulate and very feminine, it is hard to tell that she was not born a woman.

“Maybe the numbers of gays, of people with sexual identity issues, might be the same as in other countries,” said Suttirat, “but because Thai society and culture tend to be very sweet, very soft, and the men can be really feminine, if we tend to be gay, many of us tend to be transgender.”

So does building a special toilet in school advance the cause of winning wider acceptance for transsexuals?

“At that age it’s good for them to have a specific place,” she said. “But when they graduate from school or university, they will know how to have medical treatment. They won’t want to go into a transgender toilet because they will want to be accepted as a woman – so they will go to the women’s toilet.”

Tolerance, said Suttirat, is not the same thing as acceptance. Despite their high profile in Thailand, transsexuals complain that they are still stereotyped – they can find work easily enough as entertainers, in the beauty industry, the media, or as prostitutes, but it is much harder to become a transgender lawyer or investment banker.

And their biggest complaint is that they cannot change their legal status. Despite a proposal during the drafting of a new constitution last year, to allow them to change the gender on their identity cards, this has not yet been approved.”

Hunting for Ae


“Cock me up too!” She said


Anyone who reads this blog on a regular basis will know that I have a number of thoroughly disreputable friends. The fact that they are such good friends probably says much about myself, come to think about it. A particularly rampant pal, who goes by the name of Jodahunta, was in town a few weeks back, and regailing me with some of his more lurid stories. How would you like to write that down and send it to me, I asked. I didn’t think he would. But he did. So here is the first of Jodahunta’s adventures. He has threatened to send more, and they will appear in due course.

I have such a clear recollection of my adventure with Ae that it seems like just a few months ago, even though it was back in 2005. I will never forget how she came out of her sister’s bar to meet me on Soi 22 because I couldn’t find the place by myself. All legs and bare midriff, a skimpy blouse tied at the bust and the shortest shorts you ever saw!!

We went back into the bar and had some drinks and chatted and got to know each other. We played pool with a couple of the GGs in the bar. I was horny and letting her know it and she was loving it. At one point I leaned against her and let her feel the rock-hard tool in my pants. She laughed and whispered in my ear: “Cock me up too!”… Up ??? Mine was ready to explode! We decided to go to the movies with her gay brother and one of the GGs but I sent her home to change first…I have little shame (perhaps none at all!) but somehow couldn’t see myself walking with her through The Emporium in those shorts. As it was, even with her dressed in more “modest” attire, we turned every head in the mall. I remember the restaurant falling almost silent as we sashayed through!

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In the line of fire

asian ladyboys

Photographing ladyboys can be a dangerous job, you know. Oh yes it can.

The other day I decided to take some pictures of a ladyboy jerking off while I lay on the floor, so that I could try and get some shots of a spurt of cum heading for the camera lens. I made myself comfortable by placing a pillow on the floor, and then I lay at full length underneath her.

Ready when you are, I called out.

This is a ladyboy who can really deliver a load, so I waited in anticipation. I saw that she was about to cum, and I watched eagerly to try and capture the exact moment. She shot straight into my left eye.

Now, this might have been amusing, but if you have ever had cum in your eye you will know it is very painful. The stuff smarts like blazes. I got my pictures, yes, but at the expense of a bloodshot eye.

It could have been worse. A couple of days after, I took some pictures of a ladyboy with a dildo pushed up her bottom. It looked really good. But a dildo (or a dick, of course) can have an unfortunate effect when pushed up the bum. What’s that? I cried, somewhat unnecessarily, as a brown goo emerged hot on the heels of the dildo.

At least she was laying on the bed, and not standing over me, I mused, as an embarrassed ladyboy headed for the bathroom.

A few weeks ago I was on my knees, getting some closeups of a particularly impressive cock. I got really close. Then I felt a firm hand pushing at the back of my head, and when I opened my mouth to protest I felt something really hot and hard pushed halfway down my throat. She thought it was hilarious.

I could go on. The time I received Talisha’s dick in my eye, as I was shooting a closeup. With a dick the size of Talisha’s, I was lucky to have an eye left. The time I inadvertently swallowed a load, when I was just giving a little oral stimulation to a model to make her dick look hard and shiny. And the time I got a load up my left nostril when I was using the macro lens.

Yep, it’s a tough job. Sorry, no vacancies.