the third sex

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I had a stack of emails following my posting of Sergeant Shameless’s story last week, not a few of them asking me if I was myself the shameless sergeant. I am not. I have known the gentleman (sic) for a few years and whenever he has travelled to this part of the world he has sent me a series of lurid emails detailing his adventures.

The last time I saw him I suggested he write for a wider audience, because I always found them so entertaining. This he will be doing. In the meantime, I’m adding below a message from the Sergeant, in which he is far too kind about me, but which does I think establish that he is a separate entity to myself…

“Our good Captain O has invited me to write sporadically about my ladyboy adventures in this here blog. I have already contributed the first, Spiritual Awakening, but before I continue with my hedonistic accounts I would like to share with you why I think captain-outrageous.com is such an exceptional website as far as internet eroticism is concerned, and such a unique venue for the ladyboy experience. In my view, four characteristics set it above the rest.

1 Unique models While you will find many of the Captain’s models in other websites, some you won’t. These latter models are mostly younger, dreamy ladyboys (some in transition still) who have not yet become mini-sex businesses. For many of them, Capt O was their first shoot and some will never do another one because they are too shy and they are simply not in the ladyboy sex-industry mainstream.

2 Superior photography The Captain’s crisp, natural Bangkok-light photos are the closest it gets to seeing a ladyboy with your own eyes. There are no yellowish skins with flashlight glares, no out-of-focus pictures due to automatic light exposure, and no obvious airbrushing. The close-ups are unmatched: you can see the cuts and lumps of a boob job, every entangled pubic hair, the wetness of a penis tip, the density of an ejaculation, or tell if a butthole was puckered or relaxed when the photo was taken.

3 Capturing the complexity of ladyboy beauty You can show ladyboys as girl-whores with cocks, or you can show them as the vulnerable seductresses at the peak of their ephemerous beauty that they are. The Captain achieves the latter by bringing out the unique femininity of each ladyboy in well-staged photo sequences that show both the bashful and slutty sides of his models from a lover-in-the-room point of view. The use of lingerie is masterful in this regard, such as bridal negligees that can look awkward as much as sexy, and delicate lace panties painfully cramping throbbing cocks or lovingly lowered to expose nubile bottoms.

4 Showcasing the ladyboy dream But what I like the most about the Captain’s photos is that they give me a glimpse of what life would be like if I could live in Bangkok and befriend ladyboys on a day-to-day basis. Having my own apartment where ladyboy acquaintances come by, hang out on the balcony or the couch, take a bath, try on girlie clothes, take pics, and as easily go together with me for a walk in the park as for a hop in the sack. Just like the Captain makes me dream about in his shoots.”

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There is a pink vibrator that I use sometimes for photoshoots. It has seen the inside of many a beautiful ladyboy bottom, and consequently I am very attached to it. The other day I had used it when I was taking some pictures, then I washed it in the bathroom and left it on the living room table. My maid, who has been with me for many years knows everything I do, and I left it along with a bundle of flimsy nighties and other gear for her to pack away the next day.

That evening, a couple of ladyboys came round. I did a shoot of one while I left the other to watch TV. The following morning, I realised that my trusty dildo was missing. The only possible explanation was that it had departed with the two ladyboys the previous evening.

I told my maid when she arrived, and she almost cried with laughter. She is a country girl at heart, and in very colourful Thai told me what she thought the light-fingered ladyboy would be doing with it.

I saw the funny side of things, resolved not to leave anything expensive laying about next time they came round, and made a mental note to buy a couple more vibrators when I next went to London. I had been photographing that one too much, anyway. It was made of soft plastic, and I had been using it out of consideration for my models. The others I have are all hard plastic, and because I like to see the models put a dildo all the way up, I seldom use them. Hard plastic must be painful, and I don’t want to see anyone being hurt.

A peculiarity of Thailand is that sex toys are not available here. Not legally, anyway. Thailand bans pornography, and it also bans sex toys. There was a case a year back when a Thai woman was busted for selling vibrators and other sex toys, and although I imagine she was simply fined and had the goods confiscated, it did reveal the ambiguity that lays at the heart of the Thai attitude towards the sex industry.

Prostitution is illegal too. But of course you can go almost anywhere in the country and find yourself a girl, a boy or a ladyboy, and no one will think it odd. There is, in short, no real need for dildos. I expect my light-fingered ladyboy friend took my favourite prop because of the sheer novelty of the thing, and that it now forms an interesting conversation piece in her apartment.

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When I did Pim’s photoshoot, she told me she had a lot of very beautiful ladyboy friends. I want to meet them! I said. All of them. So a few days later she brought Anna, her roommate, to the Nana Hotel. Anna was super-cute: tiny, with the kind of dirty-sexy expression that does evil things to me. For such a small girl, I couldn’t believe the size of what she had. I was surprised she didn’t fall over. Shaved pubes too, which makes it look even bigger. Gorgeous.

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One of the pleasures of running this site is the lively and often provocative correspondence I get. A regular writer is someone calling himself Sergeant Shameless. Often he is indeed shameless. That is what you get for allowing the non-commissioned ranks to run amok. But the other day he sent me the following highly interesting item, and I asked him if I could reproduce it here. He gladly agreed, even though I declined to pay him, and I have a suspicion we might be hearing more from him later.

Many Thais are mystic and superstitious, and the ladyboys we love, being young and with limited education, are even more so. I would like to share an interesting experience I had, and stress how important it is not to laugh off their beliefs even if they seem crazy to our rational and sceptical Western minds.

On a recent trip to Bangkok I was joined by a ladyboy sweetheart of mine, who says I am the one for her, even though we have different lives continents apart (and no! I don’t send her any money!). We actually met in the context of a threesome, when a ladyboy I dated (and now a big-cock internet superstar) brought her along.

You may not believe it if I say that we got feelings for each other as we made love with me being the ham in a ladyboy sandwich. Well it happened! And the truth is that I care for her enough to give her advance warning of my comings to Thailand and set time to enjoy with her alone. This last trip, I chose to stay with her for four days and nights, in what was another marathon of round-the-clock sex as only a ladyboy-in-love can give you.

Read more »

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As an Englishman, writing on the subject of ladyboys I sometimes have a problem when I consider that half of the members of this site are American.

Writing in praise of a beautiful bottom, I would naturally use the English word “bum”, which has been in currency since the middle of the 14th century as a slang term for the buttocks. Americans however would consider that I have added a sexual interest in hobos to my list of perversions, and in vain I would protest that they have been using the word “bum” to describe a tramp or loafer only since the middle of the 19th century.

In fact even the British have taken to using the American meaning, at least when using phrases such as “bumming a lift” and “bumming around.” We even say “what a bummer” when something goes wrong, although to persons of a certain age a bummer is a homosexual. This however belongs to the days before a homosexual became a gay, and quite likely no longer raises a snigger amongst English schoolboys.

(”Gay” however does raise a snigger even amongst those old enough to know better when it is spotted in its original innocent meaning, which lasted up until the 1960s.)

I am not able to use the word “ass”, because for the English an ass is a donkey. I am on shifting sands here, I do admit, because “ass” has also been used in England as a variation on the word “arse” for many hundreds of years. In fact, the word “donkey” was coined at some time in the late 18th century to remove the potential for embarrassment when talking about a beast of burden. But to modern-day Brits, an ass is still either a small horse or a stupid fellow, and has little or no sexual connotation.

I am not able to use the American term “buns” as this is the product of a bakery and has no sexual meaning, while a “butt” is to us a barrel in which we hold rainwater. If I use the French word “derriere”, which I think is really rather sexy, bringing to mind saucy French maids and frilly knickers, I might completely mystify a lot of people, and cause many more to think I am being precocious.

Why do I suddenly raise all these questions of language? Well, I have just spent a highly enjoyable but chaste four-week holiday in London where, kept indoors for much of the time by freezing cold weather I wallowed in a biography of William Shakespeare and also a large tome on the history of London and its various dialects, both purchased with book tokens gratefully received as Christmas presents.

So, to sign off I will defiantly reproduce this piece of doggerel spotted recently in a British newspaper and purporting to be the translation of an old Middle Eastern poem:

There is a shepherd boy over the river
With a bum like a peach
And he’s waiting for me
But I cannot swim.