the third sex

A friend the other day warned me about a ladyboy I was about to meet who, he had discovered, had robbed him of some money when she was left briefly alone in his room. Have you ever had that happen, he asked me.

I replied that in all my years of having been involved with ladyboys I have suffered only three thefts, and two of those were by the same ladyboy. She had stolen a camera from me, but it was a cheap film camera that I didn’t use, and it was several weeks before I realised that it was missing. The other item was a dildo.

“That pink one?” asked my friend with interest. He knows the site very well. I complimented him on his memory, because this was several years back. I had bought the thing from the Ann Summers shop in Oxford Street and had been quite fond of it as a prop, as it was a nice colour. It was a long one, but nonetheless I had had several models who managed to get it right up their rear ends, with the help of a large dollop of KY, and the photographs had been pretty good.

The dildo was the vibrating type, and I had used it in a couple of videos: you can hear it buzzing away like an electric razor, although you cannot see it vibrating because (tee hee!) it is largely hidden.

I was always careful when using it during a shoot because it would have been easy enough to cause damage to the poor model. And that brings me onto the subject of haemorrhoids.

I was taking photographs of a gorgeous young ladyboy only a few days ago, and getting quite worked up about her. Then she pulled down her pants so that I could get some up-the-bottom shots and I saw that she had a bad case of the dreaded piles. This of course can happen all too easily when something hard is rammed up the bottom (despite what a lot of people think, it isn’t designed for that). And of course, that is partly what ladyboys are all about (bless them).

But it made me go cold. It does indeed turn me right off, especially if I have to sit in front of the screen and photoshop the nasty little swellings and contusions out. You get to see them in clinical detail when you do that, and they are not pretty. And I see so many cases. After all, if you are poking a camera lens up someone’s bum, and as many bums as I do, you are asking for trouble.

Some years ago now (look away at this point if you are of a queasy disposition) I knew a ladyboy who was very well known on the circuit, which was much smaller than it now is, and who in those early internet days had become a star of most of the LB sites. She had a cute face and body, and the sweetest little cock, but she also had, as the doctors would describe it, a prolapsed anus. The lining literally hung out of her bottom by about half an inch, and she had to tuck it back in by hand. It was a real nuisance when taking photographs. Obviously she had been banged too hard too often, and the lining had become detached.

(You can look back now.)

There was also the case (uh-oh, I think you had better look away again) of a really lovely ladyboy who I photographed very soon after she had been fucked by someone with a really thick dick, for the skin on both sides of her hole had been worn right away, leaving two very sore looking abrasions. Again, this caused me a lot of grief in front of my screen, although not nearly as much as it must have caused the ladyboy.

(Right, I’ve finished.)

So, I have always been very careful when doing that kind of thing myself with ladyboys. Some of them have a natural talent for taking it up them, and do not suffer any ill effect. But others are surprisingly tight. I have examined closely well over a thousand arseholes and probably have more expertise than the average doctor. I have also probed an impressive number. Believe me, a tube of KY Jelly is an important part of any gentleman’s wardrobe. You wouldn’t want to spoil any of my pictures, would you?

How many men, I wonder, lead secret lives? This thought occurred to me recently when I met up with an old friend, together with his wife. They made a delightful couple, clearly devoted to each other. Yet I know that as he roams the world on business, he indulges in his deep addiction to ladyboys. “I can’t do without them,” he explains. “I don’t bother with girls anymore. It’s the ladyboys.”

There are plenty of other examples. The friend who on a recent visit to Bangkok managed to leave his girlfriend enjoying the hotel spa while he went for a quickie with a ladyboy. The married man I knew who on a visit to Bangkok went full-blast at the ladyboy scene, explaining to me afterwards that he was perfectly happy with his married life and that he loved his wife, but that ladyboys excited a different part of his personality: “It’s almost like I’m two people,” he said.

I remember the young IT specialist who had contacted me before his first visit to Bangkok, saying he was desperate to meet up with ladyboys but was too shy to do it on his own. “I don’t think I could handle the bar scene,” he said. So I took him to KC3, where in his urgent need to get started before he lost his bottle, he took up with the first ladyboy who spoke to him, bar-fined her, and as he told me later, almost came in his pants when they got into the hotel room. “It was all over in 20 minutes,” he said. I tactfully refrained pointing out that the girl he was with was one of the most ordinary girls in the bar. In his rush, he hadn’t noticed. He told me that I was the first person he had ever confided in. “If they ever heard about this in the pub, I would have to move out of the area,” he explained.

Then there was the university lecturer who asked for a discrete introduction to one of the models on the site so that he could spend time with her when he was out here on an exchange visit. He told me that a couple of his students were also spending their holidays in Bangkok, and that the possibility of meeting them when he was cruising for ladyboys was a mortifying one. “Back at home I’m regarded by my students as a pretty boring bloke, married for 22 years, two kids, no interests apart from my subject, art history,” he said. “But every day I fantasise about ladyboys. I’m not a closet gay, I have a satisfying sex life at home. Ladyboys stir up emotions I never knew I had.”

I myself like to believe that I pass as an ordinary person (albeit a devilishly handsome one), and that going about my daily business no one would possibly guess that the evening before, I had been eagerly exploring the cock and bottom of a young ladyboy eager to help me in every way she could.

In some ways, having a secret life is itself exciting. But while it is fine for me, living here, and able to indulge and then cover my tracks easily enough, it is a lot less easy for those who only visit Thailand or other countries with a sizeable ladyboy population.

When I first started out with ladyboys, it was long before the days of the internet. I didn’t even know what ladyboys were. I had never heard of them. These days, with so much ladyboy porn on the net, it is very easy to become addicted to the images. For most people, they are something entirely new. Something completely exotic that excites because it has never been seen or experienced, and because so many of the ladyboys who are posted on the net are under any criteria, extremely beautiful. In my experience, a lot of men visit Thailand because of the ladyboys.

For those men who are married, or in long-term relationships, does going with a ladyboy constitute being unfaithful? This is something of a conundrum. Having sex with a genetic girl certainly is. Having sex with a member of the third sex is problematical, in ethical terms. Enjoy the moment, is my advice. And, of course, keep quiet about it.

I have seen a lot of arseholes in my time (not you, mate, sit down!) and I can tell you one thing with confidence – they are not all the same.

The default setting for this part of the body is a neat little crack with a surrounding of slightly puckered skin that looks, at least to those of a poetic turn of mind, rather like a sunburst. Sometimes the crack is a little more pronounced, due to larger internal plumbing, and then it looks more like the tied end of a balloon. But, as I say, there is a world of difference, and when you get to see as many as I do, in close-up, you become very much aware of this.

Of course, although the rectum is not designed for sexual intercourse (despite what many people seem to think), if you use it in this way then you are possibly going to change the shape of the thing. I was photographing a cute ladyboy during the week and found, when she lay on her back with her knees raised, that she had a greatly enlarged bottom hole that was almost certainly not the shape she was born with. She was only 18, and already had clearly seen a lot of rear action.

Then again, there is a regular ladyboy visitor to my place who I have known for years, ever since she was 18, and despite the most intense activity in this department, she has retained the sweet and innocent looking little crack she had at that age: it does however open up to accommodate whatever is offered, as long as a considerable amount of KY Jelly is applied, and afterwards, after the storm is over, it returns to its former innocence.

Yet others I have known have succumbed to the kind of damage one might expect to happen when something hard is pushed up the bottom without too much in the way of caution by the pusher. I have seen some nasty cases of piles, and have spent more hours than I care to recall hunched in front of Photoshop to make the pictures a little more inviting. This is something I would rather not do.

A surprising number of ladyboys have smooth, completely hairless little bottoms. Some have just the faintest amount of hair around the entry point, scarcely visible to the eye and showing up only under the studio flash. Some have a thick covering of hair, which can be exciting, depending of course on the ladyboy herself. The three models I have used to illustrate this piece each have very different rear ends, and each to my mind is outstandingly beautiful. But then I like just about anything.

Those who love ladyboys and who are intrigued by this little-appreciated feature of the human anatomy are probably best placed to indulge in their interests. If you stay with GGs, then you might get yourself a reputation for being a little, well, obsessive. Gays are another matter entirely, and I don’t know what goes on over there, but the very thought makes me impotent. So…ladyboys it is.

The ladyboy who had just arrived for a photoshoot looked fine to me, except for what she was wearing. She was dressed as the Sugar Plum Fairy. And it was only lunchtime.

I looked at the totally unselfconscious figure standing in front of me. Butterfly-style hairband, sparkly blouse, and a filmy white ballerina skirt. She had travelled on the bus dressed like this, all the way from one of the suburbs to my place.

This was far from being an isolated incident. I had one model turn up at lunchtime dressed in a gold lame dress and fishnet stockings. Another with a short dress made from gauze and with her bra-less tits hanging out. Another in hot pants so small that her bottom cheeks were visible. One in a pink pyjama suit. One in a cocktail dress with sequins and wearing six-inch heels. I could go on.

Why is it that ladyboys spend so much time and effort into making their faces and bodies look so beautiful, and then trash it all by dressing like something out of a pantomime? And aren’t they aware that, while at nighttime maybe this doesn’t look too grotesque, early on a hot Bangkok afternoon, in the merciless glare of the sun, they absolutely do not look sexy.

Ladyboys don’t seem to have an off-switch when it comes to going over the top. Some of them deliberately want to shock, some are pushing the limits of their own creative impulses, some are using it as a kind of body-shield and hiding their own insecurities in plain sight. Others, however, simply don’t have the faintest idea about female fashion or decorum.

This, I would think, is what happens when a young ladyboy from the provinces arrives in Bangkok and suddenly finds an endless supply of inexpensive clothing available at markets, boutiques and department stores. You would look hard to find anywhere else in Asia that is quite so productive, and quite so cheap, in terms of the local garments industry.

Thailand is in fact famous for its fashion and garments shopping – go to Pratunam, which is the centre of the rag trade, and wander around its huge market and its malls, and you will be overwhelmed by the sheer quantity. The same applies to smaller markets such as Klong San and Huay Kwang. The output, and the demand, are phenomenal. Place a ladyboy amongst all this, and perhaps it is not surprising that impulse purchases are made that maybe are regretted later: but with the budget blown, the clothes are worn regardless.

Anyway, I unpeeled my Sugar Plum Fairy. She had a neat little wand. In the end I was quite taken by her. But I did let her find her own way out of the building, without the polite accompaniment I usually offer my models.

I once had a ladyboy friend who was excessively fond of wanking off (if that can be considered unusual). By which I mean that although she was always up for a session at any time, when I was busy working on the computer, say during a warm afternoon, she would creep away quietly and a while later I would hear a cry: “Come see this!” And she would be sprawled on the floor next to the sliding doors and the balcony, the warm sun on her body, and a huge puddle of sticky white semen over her tummy.

“You might have called me earlier,” I would say, reproachfully, because I’m never too occupied to stop for five minutes to watch a ladyboy having a wank. “You too busy,” she would reply, watching her cock subsiding, an expression of satisfaction on her face.

She would wank off in the bath, and under the shower. She would sit out on the balcony, in full view of the street (I’m a dozen floors above street-level), and wank off there. She wanked off in the kitchen once, ejaculating into a glass, holding it up to the light to admire the milky white colour and taking a tiny sip, although wrinkling up her lovely little nose in disgust.

We went upcountry, to a waterfall, and she wanked off in the bushes. She wanked off behind a tree in a banana plantation. She kept a small motorcycle at her upcountry family home, and she sat bare-bummed on the saddle, saying that the warmth of the material turned her on, and she wanked off there.

She also had a habit of laying flat on her tummy on the bed, reading, and suddenly getting an idea in her mind. She normally wore a little pair of shorts about the house, and down these would come, revealing her bare brown bum. Then she would bring herself off by massaging and thrusting her cock against the mattress, letting out with a groan and then leaping up eagerly to examine the big wet patch on the sheet.

“Oh, yes, very good,” she would say approvingly, because this was at a time she had stopped taking hormones and she was enjoying the life that was coming back to her dick.

She liked to lay face down on top of my thigh and bring herself off in the same way, generously allowing me to massage her bottom as she thrust against me, until I felt a great warmth spreading over my leg. And of course she enjoyed kneeling over my face, allowing me to lick her balls as she wanked off frantically above me.

None of this affected her ability to cum at any time I felt in need of a taste of protein, spurting fulsomely within a minute of tongue touching cock.

When I’m taking photographs I look at the model’s cock as soon as her pants come down, wondering if she is going to be an easy or a slow cummer. Very few ladyboys have an instant erection, despite the attractiveness and sexual desirability of the photographer. It needs a little gentle massage to bring a cock to life, which I am quite happy to supply, and as soon as I touch the thing I can get a pretty good idea of how effective it is going to be.

There are cocks that spring into life straight away, and which have a good deal of muscle to them. These are almost certainly going to be spectacular. But also I often find that the smaller, more limp ones can do a pretty impressive job.

I suppose it all comes down to the fact that most of the models are young, and are as fit for it as the rest of us. Those taking hormones might take a long time to get there, but they usually do. No matter how feminine they appear, they still have the instinct to ejaculate, as quickly and as often as possible, which is one of the reasons that sex with a ladyboy is usually such an explosive affair.