the third sex

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A member who has had experience of ladyboys in Bangkok says that to his surprise, one of the most compelling attractions for him was their vulnerability. He said he wasn’t talking about the big tall ones, or the over-the-top kind that you so frequently find freelancing along Sukhumvit Road. It was the quieter, more feminine kind.

This is the type of ladyboy that can often pass for a genetic girl; the kind you can take home to Mum. The kind you can easily fall head over heels for.

I also find this vulnerability attractive. I am drawn towards vulnerable people anyway, and have all too often paid the price for being a big softie. But the feminine ladyboy, in her teens, unsure of herself, her sexuality, and her place in the world is something with which I can sympathise.

As you may imagine, I meet and photograph ladyboys of every kind. I have long been able to look at someone who arrives for a shoot, and to sum up pretty accurately how she will behave when it is just me, her and the camera.

All too frequently, the brassy, confident kind who fusses unduly with her hair and makeup tends to be insecure. In front of her friends she is the extravert, but faced with me, the confidence fast subsides. So I do my best to put her at ease. I never talk too much during a shoot, as I prefer in a way for the model to forget I am there. But I do make the occasional encouraging remark, I show them the LCD screen so they can see their best close-ups, and I joke along with them to keep them smiling.

That is one kind of ladyboy with vulnerability. The other type that I feel particularly protective towards is the young, boyish kind: the Suzis, Honeys, Nickies and Nans of this world. In their late teens, they still have a child-like quality and represent perhaps more than any other members of the third sex a blending of the boy and girl. In some instances, they could probably switch back to the masculine without too much dislocation. But in others, you wonder quite what will have become of them within five years’ time.

As the ladyboy population of Thailand becomes younger and younger, this category has been increasing. Youngsters make the decision to become ladyboys, often under peer pressure, as they are entering puberty. No one knows themselves at that stage of life. By the time they reach their mid teens, they may well be wondering what they have let themselves in for. Yet in terms of their friends and their sexual experiences, they now find it difficult to break out.

I try and talk to ladyboys like this, asking about their general aims and their ideas for the future, but I have never yet received a convincing reply.

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I very much regret to say that Sargent Shameless has sent me another story, which I reproduce here. If you are of a sensitive disposition, may I suggest that you look away now.

‘Is there anything better than one big, juicy ladyboy cock?

The answer is: two big, juicy ladyboy cocks.

This time I would like to share how yours shamelessly entertained two of Bangkok’s most spectacular cocks in one single night.

Once upon a time, Casanova was the only bar in Bangkok with all non-operated ladyboys. The Sargeant was a regular and gradually became acquainted with the sphincters of many of Casanova’s accomodating staff. However, with only a couple of exceptions, such encounters were of the short-time variety despite upfront promises of passionate lovemaking until dawn and reinvigorating sleep in each others’ arms into mid-afternoon.

Being an incurable romantic, your Sargent here just started hanging out at the bar, buying a few lady drinks and then moving on to more longtime-friendly pastures. In those days, the Casanova ladyboys would dare you to play with their meat in hope of enticing you to close the deal (such live action would take place on the couches at the end of the bar distant but by no means out of sight from the other patrons). As I was often the only customer in the bar, I had my pick of all the cocks in all shapes and sizes being flashed at me. Thus I often found myself with a cock or two in my hands and/or mouth.

This was how I became acquainted with the two Casanova ladyboys who had two of the most magnificent endowments I have ever tried to swallow. As a matter of principle, I don’t use the real names of former fucks, so let’s just call them Tassica and Jelisha, who, I must add, are also old friends of our good Captain, who has featured them separately and together in his earlier pictorials.

On that memorable night, as on other previous occasions, I was practising stickshift gear with Jelisha’s cock when she asked me for the thousandth time that I barfine her. And for the thousandth time, I made up some phony excuse of why I could not do it. But this time Jelisha went hysteric on me, yelling and threatening (as only scorned ladyboys can) that I had been lying to her for five years (true), that she had offered to come with me for free (true also) and that she did not want to ever see me back in the bar (she meant it). At that point, faces had to be saved (hers and mine) so I said OK, I would barfine her if she agreed to longtime. She did and it was a date.

At that point, the equally well-endowed Tassica reminded me that I had also been promising to barfine her and asked to come along. She even said I could fuck her without a condom. As flattered as I was by such an unlikely offer (which I would not accept unless I could verify a blood test), I again excused myself and promised I would call her later in the trip…Tassica is a more calm type and accepted a lady drink instead. Soon after, all was forgotten and I was playing with their rock hard cocks and briefly had both of them in my mouth for a picture.

When the time came, my interlude with Jelisha was as I had expected. Kinky as hell but no chemistry. Her cock was indeed spectacular and was rock hard the whole time. Long, heavy, hairy, pointing forward with a slight bent. She complimented me on the size of my own tool (bigger than hers, but I am farang), and on my oral skills, which coming from her meant a lot to me (she is not the complimenting kind). She took my shaft with apparent eagerness and slapped her own meat to orgasm. My attempts at kissing her while fucking missionary were met with closed lips, so I turned her over, grabbed her cock and balls from behind and let her have it full throttle. After I emptied my balls, she got up, took a shower and left. She had not asked for money, but I doubt that she would have left without a fuss if I had not given her some. As expected, she did not follow through with longtime and that was it for Jelisha and the Sargeant…

This encounter took place at the Nana where I was staying, and afterwards it must have been around 1:30 am so I decided I might as well go down for a beer and watch the NEP closing time festivities.

As usual, truckloads of ladyboys were standing around in front of the NEP in last, desperate attempts to make some cash for the night. One of them was Tassica. Our eyes met. I waved the room key. She nodded. 15 minutes and a couple showers later, I was polishing her shaft with my already cock-blasted, but still eager mouth. Tassica’s cock in full glory is rock hard, perfectly vertical, with a bulbous pink head. Yes, if I had to describe Tassica in one word that would be it: “bulbous”! Jaw-breaking, ass-ripping bulbous.

But back to the action, Tassica was surprisingly diligent to the point of sweetness, positioned for a 69, and patiently sucked my shameless shaft back into readiness. Then she duly bent over to take it as promised (after some hesitation, I did use the damn condom). Throughout the long pounding she took in order for me to come a second time in barely one hour, her cock remained rock hard as she played with it. After I came, she begged to fuck me (unlike Jelisha) and I realised there and then that Tassica’s true nature was to be a top and that I was about to have my comeuppance for all the hemorrhoids I have caused the sons and daughters of Siam. It was not so much the huge girth of her cock, but the steel-pipe hardness and the strength with which she pounded. She did stay the night, but I kinda wish she hadn’t, because in the morning she started over tearing my battered asshole with her morning glory more bulbous than ever.

To sum up, it was a memorable night in that I finally enjoyed two of Bangkok’s legendary super-endowed ladyboys. I had both their cocks in my mouth at the same time, and then did them at length separately.’