the third sex

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.Here is another story from Sergeant Shameless in which, I am sad to say, he fully lives up to his name.

“Ladyboys are like beer. The first time you have one, it tastes weird. So, you have a few more and you get hooked on the stuff.

I earned my “shameless” badge because of my wild antics with ladyboys (and ladies!). But it was not always like that. Today, I would like to tell you about my first ladyboy experience, which was not exactly fireworks but opened the door into a new experience realm (and not just sexual experience).

Like many a farang, I had been going to Bangkok to indulge in two-girl body massages, beer counter blowjobs, Thermae longtimes, and, for a while, even had a proper Thai real lady girlfriend (who made more money than me). Like many a straight farang, I openly dismissed ladyboys as gayish freaks-of-nature and cringed at the thought of inadvertently hooking up with one of the totally passable post-ops.

Yet, at the same time I could not help but be intrigued by the ladyboys. In my forays into Nana Plaza, I used to stare across from the now-closed Woodstock at the Casanova ladyboys, and eventually was enticed into their bar. In those days, they would openly play with their cocks and mine and shove their plastic tits on my face to lick. But, in the end, I would pay for a couple of lady drinks and leave alone.

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. . . . . . . …Dee: A bit bashful

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.Ladyboys are not into other ladyboys. I have only ever known of a couple of genuine ladyboy “lesbian” relationships, because ladyboys consider themselves female and they are into guys, not other ladyboys or for that matter, girls.

Fixing up a ladyboy lesbian shoot is therefore not always that easy. Some will do it simply because you ask, and that’s okay by me. But getting any real combustion going when you are taking the shots is something else entirely.

A while back I set up a shoot with Bea. I wanted to take some pictures of her with Toffee, but Toffee and she are roommates and therefore friends, and both nearly died of embarrassment when it came to the action.

Then I asked Bea if she would do it again with another friend, and she said she couldn’t do it with people she knew. A stranger would be okay. So I brought along Dee, and the two sat in my apartment and eyed each other up rather warily, then I took them off somewhere else and the shoot went okay. But it was pure sex – the kissing and hugging I also wanted to capture just didn’t happen.

A similar thing happened when I got Talisha and Jessica together. Again, these were roommates. They also happened to be the two of the most spectacularly endowed ladyboys on the Bangkok scene. They were happy to pose for the camera, and there was a little sex play, but play was all it was. Nonetheless, I was really happy with the set. With those two ladies, it would have been difficult to go wrong.

This shyness extends to ladyboys seeing each other naked. When I took Pat’s photos recently, she was terrified that her two friends Cherie and Ann, who had come with her, would catch a glimpse of her undressed. The door had to be firmly shut all the time.

However, I next did a shoot of Cherie, who is one of my favourite models. She isn’t so shy. Halfway through she went prancing out into the room totally nude, much to the amusement of the other two. She had a red feather boa, and danced around the room and out onto the balcony with the thing wrapped around her gorgeous little body. I found the whole episode very erotic, and Cherie clearly enjoyed herself.

But then the other day I did a video shoot of Dee, another girl who has a spectacular cock. On this occasion I brought along my maid’s son Ek, a fledgling ladyboy, to handle the video lights. I dressed Dee in a college girl’s uniform, and got busy with the video camera.

As the shoot progressed, I got more and more annoyed by the fact that Dee was covering up her dick with her hand. Then I turned round, and realised that Ek was standing behind me, admiring Dee’s erection. I couldn’t bundle him out of the room, because he was there to shift the lights around.

In the end, I lost my patience with Dee. Look, I said, this is a movie. I am trying to film your cock. How do you expect me to do it if you keep covering the f*@!&*g thing up?

“Sorry,” she said “I very shy.”

I got the video done in the end, but I had to throw away an awful lot of footage when I was editing the thing.

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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.

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I knew that I had met Gow before, and I was sure I had taken her picture. But I couldn’t remember when or where, and I couldn’t find her when I flipped back quickly through the site. Oh well. I really liked her, with her cheeky little smile. Gow is a student but works in a store part-time.

There are two hundred pictures of Gow on the main site. Click here to visit

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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.”