the third sex

Sometimes Sargent Shameless surprises me by revealing he really does have a soft and sentimental side. Not often, I have to admit. Here he relates how, during his recent debauchery in Pattaya, he was convinced he had rediscovered his high-school crush. She did however prove to have something he would never have guessed at during his misbegotten schooldays.

I never thought I would be writing about my high-school crush for no venue called third-sex.org.  The fact is that Shana (not her real name, but close) was in every way a girlie girl and, although I never actually saw, I am sure  there was nothing but sweet, pinky, soft-hairy teenie pussy where a ladyboy dick need not be.  Like all high-school queens, she had that perky-sassy beauty that pubescent boys cannot resist: deliciously petite, and she dyed her brown hair blonde, which in those days made her a sophisticated teenage vixen. Her best attribute was her bubbly and tightly packed butt, which inspired many a jerk-off session from me and my testosterone-rushed schoolmates.
 
Let’s jump the clock to a few decades later when your Sargent Shameless was out on the sois of Pattaya for another night of ladyboy buggering.  For this particular night, the plan was to take home this newly arrived hung beauty that I had been groping and fondling in her bar, and knew it was time to either barfine or forget her.  So what I did was I went to her bar around 20:30, had my kick-off Chang beer, played for 10 minutes with her oversize dick to make sure everything was functioning (it was!) and then bar-fined her but told her to wait for me until later. You see, it was kinda early in the night and I wanted to do some bar-hopping by myself and get the kind of attention that you can’t if you bring your own lady into other ladies’ bars.
 
And then it happened! I was walking past a row of outdoor lady bars and, waving at me from one of them, I saw Shana! Like she looked like when she was 16.  With her dyed long blond blow-dried hair hanging down her back over that bubbly butt to die for. Her dark eyes, pale skin and mischievous smile were just as I remembered her.  But the Sargent’s ladyboy radar never shuts down and immediately I knew that the Thai version of my high school Shana came with a hard little dick as standard equipment!

As I looked mesmerised at Thai-Shana, she grabbed my arm and dragged me into her bar (which had seven or eight ladies and one other ladyboy). We hit it off really well, but I had to tell her that I was busy for the night and would come back for her the next day. She was understandably disappointed and I, uncharacteristically, felt that I would regret it dearly if for any reason I did not get to be with her.
 
So I went back to the previously bar-fined ladyboy, took her to my hotel room, got my money’s worth with one hour of 69ing and taking turns at unclogging each other’s dirt pipes (the Captain says:  that’s the Sargent Shameless we know!) and even though we had agreed to a longtime sleep-over, I sent her off early and got on a motorbike myself and rushed back to Thai-Shana.
 
The rest is history! After the first lady drink, I knew I would be spending the remainder of my stay in Pattaya in the loving company of Thai-Shana. Even though she looked like my high school Shana at 16 years old, she was 22, she was from Bangkok, and, contrary to my initial impression, she was 100 percent Thai blooded, with no farang in her.  But soon she had THIS farang 7 inches deep in her sweet orifices as I had so often wished I had done to Shana (or any other girl for that matter) in high school.

For my remaining four days and nights in Pattaya we lived as high school sweethearts, going together to the beach, to movies, bowling, shopping, and, after taking HIV-tests together, having wild, passionate, unprotected sex three or four times a day.  At night, she would hold me in her arms as I fell asleep gently clutching her ever-erect little cock.  She was kinda emotional when the time came for me to leave, and I knew that Thai-Shana is one of those rare ladyboys that I will be looking up again.
 
Because, for a guy, can there ever be a fantasy more enticing than his high school crush?…Only his high school crush with a penis!
 

Here as promised are the latest adventures of Sargent Shameless, emailed to me from some semen-soaked hotel room in Pattaya. I post this two-part account as a warning about the depths of depravity to which it is possible to sink.

Could it be that my ladyboy indiscretions are possibly wrecking the marriages of people I have never met and who don’t even know who I am?

Your Sargent Shameless was asking himself this question as he laid on a beach chair in Koh Larn, a small island with sandy beaches a few miles offshore from Pattaya, while his ladyboy companion sensuously rubbed sun cream all over the Sargent’s wicked body.
 
Since I never use real names, let’s call this serviceable ladyboy “Fire” because she is hot as hell. You see, Fire is the kind of knock-out babe who can stop a beach every time she moves. In her tiny thong bikini, 5 foot 10 inches tall with stick-out, but not exaggerated, breast implants, she is not shy about showcasing all that gorgeousness and walks and giggles and gesticulates in exaggerated girly ways for all to see and gawk. Add this to the Sargent’s own penchant for showing off and you have a sinful spectacle that ordinary beachgoers will never forget.
 
To go to Koh Larn, one takes a boat from the pier in South Pattaya and it is an hour’s ride, which means that something of a shared experience happens between all the boat’s passengers. Everybody notices everybody else: the young couples on honeymoon or with small children, the elderly couples seeking to rekindle the fire, the European spinsters, the aging farangs with their considerably younger Thai GG girlfriends, the Japs, the Koreans, the Arabs, the accidental Thais, etc…. But there is only one wild tall guy holding hands with an equally wild tall ladyboy, taking pictures of her long hair flowing in the sea breeze, and even making out on the deck with long sloppy kisses for all to see… That guy would SHAMELESSly be me!

I can’t help it but relish how when I am with one or more ladyboys, other Western men in Thailand look at me with baffled curiosity, disgust, or admiration (I can never tell which) but they look!..and their aging wives look also but with scared contempt as they know that there-but-for-the-grace-of-God could go their husbands.
 
When the Pattaya boat arrives at Koh Larn it stops off the beach and everyone gets into a smaller flat boat and stays at this small secluded beach, which means the group dynamics with the fellow passengers continue until the boat takes everyone back a few hours later. In our group that day there was this young Russian couple, and I swear the lady looked just like Anna Kournikova the hottie former tennis player. Blue eyes, beautiful straight blonde hair, pouting rose lips, long perfectly toned legs, perky breasts, a tight butt to die for, every inch of her body impeccably groomed. In brief, the kind of girl that I would have cut an arm off to be with when I was in my 20s.

Yet my ladyboy Fire was stealing all the attention that normally the Anna Kournikova look-a-like would have come to expect semi-naked on a beach, including from her young Russian husband who could not keep his eyes off Fire. He even followed us into the water and possibly witnessed as I floated with arms and legs clutching a huge inflatable tyre and Fire dove in and came out between my legs and discreetly sucked on my cock for a minute or two. (The Captain says: Shame on you Shameless! I hope you were far enough out at sea for the innocent onshore not to see you!)

Later, back on the sand, the Russian guy kept looking at Fire and I noticed that at some point he was adjusting an erection in his speedos. His newlywed wife must have noticed something also, because on the boat back to Pattaya they were clearly having a lovers’ tiff. I could not help but get the feeling that I might have indirectly undermined their marriage by planting the seed of ladyboy lusting in an otherwise straight-shooting young lad. And also that I probably do such marital undermining everyday that I party for-all-to-see with ladyboys and some of the men watching me from afar wish they had the guts or a chance to experiment or start to wonder about it.
 
Because, at that moment on that boat, I knew for sure that the next time the Russian guy would make love to that gorgeous wife of his he would be fantasising he was fucking my ladyboy Fire. .. and that in no more than 10 years time he would be back in Pattaya to fulfill his fantasy with a ladyboy of his own.

I had the following missive from Sargent Shameless a couple of days ago, the precursor to a series of others detailing his most recent adventures which I am afraid I’m going to inflict upon you shortly. I think you begin to see how he acquired his soubriquet.

I am in Soi 6 in Pattaya right now having bolted out of Hanoi for a ladyboy refresher course. I am a bit tipsy and on a ladyboy high…something really funny just happened that I  think you would like to hear about so I came to the internet shop to write it right away while I give my tonsils and dick a rest. 

Something like four years ago I was in Pattaya for a couple of weeks of the usual debauchery, even though I was supposed to be in Bangkok on company business.  Since I was on a hotel expenses paid gig, I was in a bit of a conundrum as I was expected to present hotel receipts to be refunded, but if I turned in a Pattaya hotel receipt everybody at work would know exactly what business had brought me to Thailand.
 
This did not stop me from getting on with the main event, and on my first night in Pattaya I hooked up with a wonderfully hung ladyboy and on the next day her more modestly endowed but perfect little rosebud of a butthole ladyboy roommate was joining in for the horizontal Muay Thai.

The following morning, after I indulged with my sleep buddies in an invigorating farang sandwich, I began to worry what I was going to do about the hotel receipts.  I asked the ladyboys if they knew of a Bangkok hotel that might pass me a receipt for a fee, but understandably they did not.  So I decided to fabricate a receipt right there and then in Pattaya. Again, I asked my ladyboy companions if they knew of a store where I could buy blank printed receipts on which I could write a made-up Bangkok hotel name and charges.  This time they said they could help me and we all got on motorbikes and went to some kind of general store that had a very well stocked stationery section.  I bought a good quality book of receipts printed in Thai and also two commercial ink-stamps, one of which said “PAID” in English, and the other said “THANK YOU” in Thai.  I thought the stamps would lend more credibility to the receipts.
 
Back at the hotel, one thing led to another and before long I was using the stamps on the ladyboys’ nubile naked bodies. I especially enjoyed stamping “PAID” on their soft butt cheeks and “THANK YOU” on the foreskins of their sweet cocks.  But I also stamped them on more visible parts of their bodies like their foreheads and arms, so when we went back out for a night on the town other ladyboys saw and admired, and some asked if they could be stamped also (it was of course a clever way to offer to come to the Sargent’s room and play with the artillery pieces…).
 
For the rest of my stay in Pattaya, I used the stamps on all the ladyboys I had the pleasure of having pleasure with and it became sort of a running joke but at the same time a badge of honour for those ladyboys complimented with your Sargent’s affection and/or cash.  When I got back to work, not only did I present and got refunded for the made-up receipts but I also inflated the made-up hotel charges so that my employer actually paid for most of my ladyboy companion fees (Captain’s note: It doesn’t get more Shameless than that!).

Fast forward the clock to four years later (now!) when I am back in Pattaya, and after a night of wild passionate lovemaking I was saying my morning goodbyes to a newly met ladyboy cutie, but I could sense that something was bothering her.  I knew I had rewarded her appropriately, so I asked her what was wrong and told her to speak up. With puppy eyes, she mustered the courage to ask me: “But are you not going to stamp me?”
 
At first I had no clue what she was talking about.  But after she started making the gestures of stamping her buttocks and forehead it all came back to me.  I could not help but feel like a god.  I smiled, slipped her an extra 100 baht and promised to stamp her all over next time. It really made my day to know that a ladyboy who I had never met (and who was still in high school in northeast Thailand four years earlier) would have heard, presumably from another ladyboy who had recognised me, about the Sargent Shameless stamping spree. There is nothing for a man like knowing he has left his mark for the future generations…in my case, for the future generations of ladyboys!

Sargent Shameless has recently unleashed himself upon Pattaya, and left a trail of sore ladyboy bottoms in his wake. Pausing for breath on his return, he penned me his thoughts on the scene there.

A couple of months ago I wrote about the changing go-go bar scene in Bangkok and my main point was that while the numbers and quality of women in the girlie bars are visibly declining from 10 years ago, the opposite holds truth for ladyboys, who are more plentiful and beautiful than ever and may well be the future of the Thai sex industry.

I would now like to share also my updated view on the Pattaya scene. I was there end-2010 and, like in Bangkok, there are more ladyboys than ever. I counted at least 12 all-ladyboy bars (Soi 6 alone has five!) while 10 years ago I knew of only two: Hi! Boss, which I considered Thailand’s top ladyboy bar in terms of raw talent, is now all but defunct with three sorry looking ladyboys hanging around the premises…and Limmatquai–Pattaya’s original all-ladyboy bar off Walking street–which has closed down!

Speaking of Walking Street, it could now aptly be renamed “Ladyboy Street.” Late one night, I counted over 50 ladyboys of all shapes and sizes, including a skinny Russian one that I detected amidst his lady-for-sale compatriots, and scores of cruising freelancing ladyboys can also be seen on Beach Road (the Captain says: The Sargent may be an old hand but you can’t be too careful with street pickups who may rob you in your sleep or worse…).

Also, so many of the beer bars now have several ladyboys mixed in with their lady staff. These ladyboys tend to be the sweeter type, who are afraid to be around rough ladyboys in all-ladyboy environments even if it means far less revenue for them. I have had great luck with such ladyboys.

I also saw a few ladyboys amidst the female staff plying their trade outside Pattaya’s ubiquitous massage parlours. Which means that you no longer have to be in the know (like me!) to know where to get a professional massage (with optional sex) performed by a ladyboy.

Even in nearby Jomtien, better known for the gay action, I spotted far more ladyboys, not to mention feminised boys, than I remembered from previous visits.

In line with this expanding ladyboy trend, Pattaya also has more boy go-go bars, and other sorts of venues for gay activity, than ever. While 10 years ago Boyz Town was a self-contained gay enclave, the action now has spread to the two nearby Pattayaland sois, displacing all but a couple of the girlie bars in the process. In fact, the infamous Penthouse Hotel is now completely surrounded by gay action and it has opened its own ladyboy go-go bar; it should not be long before the in-house kittens are all of the three-legged variety. There is even a new gay go-go bar on Walking Street with the boys hanging outside in their white underwear for the Russian tourists to gawk…

What about the girl scene? Good question! There are still more girlie bars and beer joints than anyone could even begin to count. I noticed however that some of the girl bars that I patronised 10 years ago because of the choice and quality of their staff have gone downhill, or even closed. On the other hand, I visited new bars with gorgeous girls dancing, although not all were available for private sessions (a new for Thailand!). New, huge outdoor beer plazas have opened all over town, which makes me wonder if others have closed and the ladies moved or if they represent a net addition to Pattaya’s pussy count. Motorbiking around Pattaya I also spot many well staffed bars and go-gos in the inner, residential sois that used not to offer such sinful commerce.

In sum: Pattaya, unlike Bangkok, does not show signs of worsening prospects for action with girls, and, like Bangkok, it has more and sexier ladyboys than ever.

For those of you who still think that  Sargent  Shameless is an alter ego I created, today I offer some evidence to the contrary.   You see, out of nowhere, the Sargent confronted me with this highly personal questionnaire knowing  very well that although I am a private sort of chap it would be awkward for me to refuse his request.  So I pour my heart and soul into answering the questions as best as I can, and what do I get in return from the Sargent?  Snappy one liners mocking my thoughtful answers. Would I put myself through this if I was in control of the Sargent’s persona?  Definitely not.  I am thinking I should have ignored him and his  questions, but I do get him to tell the world about his entertaining personal life, so it’s only fair that I tell something about my own.  So , here I am more raw and vulnerable than ever before (and never again Shameless!).

I was very impressed by the Captain´s follow-up piece to my reflections on Thailand´s ladyboy boom.  His own reflections are underpinned by years of experience and expertly drafted showing his fans why he is the CAPTAIN and I a mere Sargent. Well, at least the Captain admitted that I am not just a big hairy dick on legs seeking at all times to lodge inside sweet girlie-boys butt cheeks.  I would like to further establish my credentials as a visionary on ladyboy buggering by challenging the Captain as follows:
 
10 Straightforward questions the world is dying to know about the Captain:
 (followed by your Sargent´s TAKE on the unexpectedly (for me!) candid responses by our sweet and sensitive Captain.)

1.At what age did you have your first ladyboy experience? 

I was very young! Young enough never to have heard of ladyboys. But this was pre-internet. Unless you travelled to the Far East you were unaware of their existence. I saw my first ladyboys in Singapore, in the old Bugis Street. I did not know what they were. But what I did know was, that they looked gorgeous and they came on really strong at you. For a young English guy, on his first Far East trip, recently married as I was at the time but deeply unhappy because the relationship wasn’t working, it was all heady stuff. Were these girls really girls? What was under those dresses? It really wasn’t difficult to find out.

The Sargent´s TAKE: It sounds like the 1974 classic movie “Emmanuelle” but starring a confused Brit instead of the sexy Sylvia Kristel.
 
2.Had you previously had sex with anyone with a penis?  If not, did you think about it?

No, I hadn’t. I hadn’t even seen anyone else’s penis, except under changing-room conditions or during the wanking-off sessions that nasty, stinky little English schoolboys get up to. I hadn’t even thought about it, except to idly wonder from time to time, as we all do I suppose, what it would be like to be in the girl position. But I never fantasised about it. Never thought about performing fellatio on anyone. My thoughts were entirely about girls, and I was obsessed by them like any other normal youngster. I quite simply did not, and do not, like men. I find men to be physically repulsive. I knew very few people of my own age who were gay, and those I did know didn’t talk about their preferences. People didn’t in those days.
The word “gay” wasn’t even in general use then. There were a few middle-aged homosexuals around, but they kept themselves to themselves. In my very early days as a foreign correspondent I remember fending off the advances of a Saudi taxi driver, and of a Swedish man in a Stockholm bathhouse. Incidents like these were so rare that they made good stories for later. That shows you how sheltered a life I must have led. The only indicator that I can fish up out of my memory as to the future course of my preferences was an absolute obsession about girls’ bottoms. I could fall in love with a girl because of the shape of her fully-clad bum. And I certainly fantasised about having anal intercourse with girls. But this was a far more straitlaced era and it was difficult enough to find a girl who would have ordinary sex with me, never mind about taking it up her rear end. Suddenly, from a rather stuffy and buttoned-down English background, in Singapore I was in an extraordinarily erotic environment. The exoticism overwhelmed me. I’ve always, throughout my entire life, been up and ready for adventure. Thus it all started…The funny thing is, that although I had never given much thought to penises, they have become another obsession. The cock is an extraordinarily beautiful and exciting thing. A ladyboy with a lively cock – it doesn’t even have to be very big – is breathlessly exciting for me.

The Sargent´s TAKE: In brief: the Captain went for ladyboys because the women in his life were not surrendering their poop chutes to him; in the process, he discovered he liked Sai Krok (big, juicy Thai sausage).

3.Your photoshoots are unique in that they show models more raw and boyish than any of the other websites. Does this denote your own preference or those of your members?  Are you personally more into passable ladyboys or feminised boys?

I have to say that it is the young ladyboys, still boyish yet with a feminine aura, that I find the most attractive. It is the natural blending of the sexes that I find alluring. I don’t really go for the heavily made-up ladyboys, or the over-the-top types. I don’t find young boys per se attractive. If they are very pretty and demure and slightly feminine, sometimes. But boyish boys, no. It comes back to my distaste for masculinity. The litmus test for how you feel about boys and girls is who you find yourself looking at when you are out in the streets: boys or girls. For me, it is and always has been girls. But when a teenage boy dresses as a girl, puts on a little makeup and sheds his masculine aura, then my interest switches. And this really can only happen at a young age. Once the feminised boy crests the age of 20 or so, the time is gone. She can go on and become a devastatingly sexy ladyboy, of course. But not a femboy.

The Sargent´s TAKE: The Captain likes young girlie-boys and is happy to share his interest with you.

4.Having got to know so many outstanding ladyboys, how have you managed to remain unattached?

I think it is the sheer number. And the fact that ladyboys are always available. A ladyboy will never decline sex unless she really has a valid reason. When there are so many, it becomes difficult to manage time, never mind about managing a relationship. If that sounds a little presumptuous, so be it. I have fallen for a few over the years, but the current has always been flowing so strongly that my feelings have been overwhelmed. It is only when I look back at the photographs I took at the time that I can bring back the emotions I felt then. But ladyboys change physically, and quickly. That gorgeous, seductive 18-year-old will become almost unrecognisable within a handful of years. Typically, she will by her mid twenties be thinking about her future, about entering the mainstream as a woman, about opening a small business in her home town. She certainly won’t be the person you fell for a few years previously. Anyone entering into a relationship needs to think ahead.

The Sargent´s TAKE: The Captain is wallowing like a pig in shit.

5.If you had to choose between having sex only with genetic women or with ladyboys for the rest of your life, which one would you choose? Please give a brief rationale for your choice.


It has been a while now, a couple of years, since I had sex with a genetic girl. I can’t say I’ve missed it that much. On the other hand I travel overseas regularly, and whenever I get to my destination I immediately start to miss ladyboys so much that I begin counting the days to my return. When I do get back, in the taxi in from the airport I’m on the phone making arrangements for the evening. I think that says my mind and body is telling me something. So, as long as I get to look at genetic girls, I could live very happily with only ladyboys.

The Sargent´s TAKE: The Captain is long past the point of no return!
 
6.  Do you relish ladyboys more for the sex or the access they allow you into their fascinating world?

Their world is fascinating, certainly. I like to find out all I can. But it has to be said that many ladyboys just don’t want to talk about it. They have made a decision and they have accepted it, and it no longer seems so strange to them. Much of my information and insight comes from regular sources, ladyboys who are real friends and who I have known for a long time. So I have to say that most encounters are for that explosion of sex, and once it is over I am happy for my friend to be on her way.

The Sargent´s TAKE: For the Captain access into a ladyboy´s world is pretty much the same as access into a ladyboy´s ass.
 
7.  Roughly, what percent of the models you photograph for the Captain Outrageous website do you have sex with? We know you don´t have time and have to remain professional, blah blah blah…but surely you must help the poor models clean up the little groin mess you make them do…please spill the beans.

The percentage is actually small but the number I photograph is very large! Many of them I do not feel attracted to. And then there is the fact that while she is being provocative, the model would certainly be up for sex if I was to put the camera aside. But once she has shot a load, then she has lost interest. As one does. She wants to get off home, or to work, or see her friends. Whatever. I do help them clean up. I do like to gently squeeze a slippery cock and run my fingers through pubic hair that is dripping with cum.
I do follow them into the shower, if they don’t show any signs of objecting. I do like to watch their little bottoms twinkling as they scurry into the bathroom. If I like her I will ask her back. Then I have the very pleasant anticipation, knowing what she can do, having seen it all up very close, and knowing that shortly it will all be mine. But I do have to admit that sometimes the shoot has been so highly charged that I can’t stop myself, and off come the clothes and the model has a little extra work to do. It seldom takes up much of her time! I think the point I have made before about not having sex with the models has referred to the fact that I never stop a photoshoot simply to gratify myself. I’m actually quite a self-disciplined person, believe it or not. Whatever does happen, happens after.

The Sargent´s TAKE: The Captain DOES fuck his models during the shoots (but not nearly as often as I would!).
 
8.Is there any sex act you would do to a ladyboy that you would not let her do to you and vice-versa?

No. I have always maintained that if you like someone enough to take off your clothes and get into bed with them, then acting prim and proper and saying “I’m not doing THAT” is not really acceptable. I used to make the same case to the genetic girls I went to bed with, the English girls mainly. I might just as well have been talking to myself. Sex is as much about pleasing your partner as it is pleasing yourself. I have done pretty well everything. Do unto others as you would have them do unto you, and so on. I would hate to think there is an experience I have missed.

The Sargent´s TAKE: Over the years, the Captain has taken the equivalent of one case of beer in ladyboy semen and the length of a horse racetrack in ladyboy cock.

 9.  Although you must have been with, I can only guess, several hundreds of ladyboys you never mention any really wild stuff (group sex, girl and ladyboy sex, fucking the maid and/or her ladyboy son, crazy BKK nights, drugs, booze, fights).  Are you really a quiet type or is there a wilder part of your life you choose not to share?

I went through some wild stuff with genetic girls a long time ago, with crazy nights in Bangkok and Manila and Jakarta and Hong Kong. Group sex and foursomes and twosomes and sessions with lesbians…and there was the time in Manila when a furious girlfriend set fire to my hotel room…but I digress. Somehow I don’t feel the need to do that with ladyboys. The intensity of having sex with one ladyboy is something to be savoured. Often two together. But if I was going crazy, then I would miss the intensely erotic experience. A beautiful ladyboy or femboy is for me an incredible high. No drugs, I’ve never touched them, never even learned how to smoke ordinary tobacco. Booze, no, I’ve done my bit in the past to support the breweries, distillers and vineyards, but my system rebelled at some point and nowadays the stuff just sends me to sleep. As for my maid, you have never seen my maid!

The Sargent´s TAKE: The Captain didn´t deny he fucked the maid´s ladyboy son… I KNEW he had done it!…

10.On a deeper existential level is the ladyboy addiction a blessing or a curse?


I would say it is a curse. It means that I am shackled to Thailand. I could go elsewhere, to the Philippines or Indonesia or South America, but I think that Thai ladyboys are simply the most beautiful. Also, as I speak something of the language and have a little understanding of the culture, their world is open to me to a degree that it wouldn’t be if I was somewhere else. In another ladyboy country, I would be just another john.

The Sargent´s TAKE: The Captain´s curse would be a blessing to most of us! Thanks for the candid answers! Long live the Captain!