On my latest incursion into Patpong I stopped at KC3, Patpong’s only ladyboy-only bar to catch up on old friends and try to make new ones. KC3’s house rules are that as soon as a customer sits down, a bunch of ladyboys line themselves up in front of him and pester him until he agrees to pick at least one of them to buy a ladydrink or possibly more. But since the Sargeant plays by his own rules, he shooed all the nagging ladyboys away while scanning the bar for the prospect most to his liking.

Before I go any further with the story, I would like to make a small interlude here to clarify that the reason I was in Patpong that night was that I was on a date with a European woman, who was looking to buy a knock-off designer purse in Patpong’s night market. Spotting an opportunity, I suggested she look for the purse at her unhurried and exhaustive female shopping pace, while I looked myself for a supposedly hard-to-find pair of men’s designer jeans. After we went our different shopping ways, I bought the first pair of jeans I saw and made a beeline for KC3. But the reality was that I had barely one hour before I had to meet my girlfriend again and thus was not even thinking of attempting any shameless endeavours.

Back to KC3. I did see a new ladyboy very much to my liking and invited her over for a drink. She started the usual small talk in hopes of bagging a paying customer. “What your name?” “Where you come from?” “How long you stay Thailand?” “You been to bar before?” The Sargeant just usually wings these questions as his mood strikes: sometimes telling the truth, sometimes not. So when the ladyboy asked, “Where you stay Bangkok?” I made up an answer by picking a number street out of my head: “Sukhumvit Soi 2″.

And then the most incredible thing happened: The ladyboy’s face lit up, she looked at me deeply and hugged me closely saying “I remember you now.” And she apologised with kisses for not having “recognized” me right away. Then she added ” I smoke yaba your apartment. You very good farang.”

Apparently, she had mistaken me for a Bangkok punter with an apartment on Soi 2 who had barfined her and provided her with all-you-can-smoke yaba (a crack-like drug favoured by Thai bartypes). Seeing the beautiful smile on her face, I did not want to disappoint her and just made a sheepish face as if saying, “I was afraid you would never recognise me.” Well, whoever the Soi 2 guy was, he sure made an impression on the ladyboy, as she took such a fancy to him that turned to me and said “You not fuck me that time, you can fuck me now, no money OK.”

My eyes popped out, my pulse started racing, and the shameless knob started throbbing against my zipper. I had about half an hour before the agreed time to meet with my girlfriend so I had to decide fast. This being the kind of situation the Sargeant lives for, I knew I had to go for it, and just hope the other guy did not have a small dick or some other feature that might give me away. So I pulled out the money for the barfine, told her to get dressed and hurry up to one of Patpong’s short time lounges. We made our way there separately, just in case my girlfriend was within visual range (thank heavens she wasn’t!). The encounter was much shorter than the Sargeant would have liked, but I made the point of penetrating her as soon as I got hard and of doing it from behind to minimise chances of her looking at me and realising her confusion.

In the end, I offered to give her 300 baht (less than 10 US$), which she accepted without bitterness at how small it was and even gave me one more big, heartfelt hug. I would have given her more money, but that would have spoiled the experience of me getting a freebie, which was the whole point.

I did make it back to my girlfriend at the agreed spot on time as she happily waved a fake Dolce&Gabana purse at me and I reciprocated by pulling out of a bag a pair of studded fake Armani jeans. Turns out they were not even my size so I had to go back to Patpong the next day to exchange them. But that’s another story.

‘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.’

The Top 10 signs you are hopelessly hooked on ladyboys

10 You start going to Thailand alone rather than with your girl-loving buddies you used to go there with
9 You start fantasising about Nicole Kidman having a penis

8 You find yourself eating bananas in one single bite
7 You start salivating at the mention of the words “pina colada”
6 You learn all there is to learn about enemas and their application
5 Your friends start saying you remind them of John Wayne when you walk
4 You walk past the girlie bars of Bangkok or Pattaya and the door girls no longer bother to entice you into the bar
3 Your girlfriend demands that you fuck her pussy at least once for every two times that you fuck her ass
2 Your girlfriend demands that you fuck her pussy at least once for every 10 times that she fucks your ass
1 You religiously renew your Captain-Outrageous membership

One of my favorite farang indulgences is carting off the mamasan of a go-go bar and giving her the old Shameless shafting. Before I go any further, let me clarify for those that have not yet been to Asia, that the “mamasan” is the lady in charge of the bar dancers and waitresses and who monitors their attendance and who they leave with. A mamasan is in someways similar to a “madame” but without the financial claim on the girl’s earnings. From what I have observed, the mamasan is a big-sister figure to most of the girls who generally look up to her with fondness and respect.

Now, I know what you are thinking… Aren’t mamasans older, fatter, worn-out former bargirls? Yep, most of them are. But not all. And that’s where the ol’ Sarge comes in. Some of the mamasans are actually chosen for the position because of their grace and skill. They may not be 18, but they can be in their mid-20s, early 30s and the Sargeant, being an equal-opportunity fornicator, can fully relish the charm of a more refined, higher status love interest.

Perhaps the other farangs in the bar will be impressed if you leave with the top knock-out dancer teeny-bopper… But chances are the rest of the bargirls will be looking at the two of you knowing that you are her third bar fine that night and you are in for a short time so short, the elevator will still be at your floor when she is back in her skimpy outfit, leaving your room, clutching the overpriced fare you agreed to.

If you want to make an impression, pick a bar with a hot mamasan and barfine her. It is easier than you think. They get paid more than the dancers but end up making less than the girls, because they don’t go with customers that often. Many are just plain bored and, like all women, enjoy a guy’s attention. The only thing is that you cannot treat them on the same level as the girls. For example, I never touch them indiscretely or discuss prices for their company.

The next morning (yes, the Sergeant likes longtime) they all feign surprise at my attempt to give them some money, but I insist and they acquiesce. One time, my mamasan left before I got up and had a chance to pay her, but I made sure to return to the bar that night and gave her a small piece of jewellery. In fact, I always return to the bar, because that’s when all the girls look up to me as the guy who fucked the mamasan. No ordinary farang.

You are probably wondering, “What does all this babbling have to do with ladyboys?” Well, some of them happen to be mamasans. A couple of days ago in this here blog, our good Captain wrote a very insightful piece on Patpong and mentioned that a former ladyboy squeeze of his is now the mamasan of one of the bars. Again, some of the ladyboy mamasans are past their prime, and some are hot as hell. The Sergeant here never misses an opportunity to get (literally) into the latter.

In Pattaya, the new craze is for bars to have ladyboy mamasans (gay bars especially). I like to chat them up and if the chemistry is there, invite them bowling, dancing, to X-cite (the kind of live showplace young Thais love), and then for intense, passionate sex the rest of the night.

One word of caution, however. After taking the mamasan, you have to be careful not to take another lady from the same bar the very next time you go there. If you don’t plan on taking the mamasan again, go back a few times and leave alone. Otherwise it will be extremely awkward for both the mamasan and the girl you take and your stock will fall from conqueror-of-the-mamasan to a low-life-one-notch-below-a-bug. (Having said that, I have actually SHAMELESSLY done it!).

To end this piece, let me just share that I dated for a while a gorgeous ladyboy mamasan in Pattaya, who had a just-as-gorgeous deputy mamasan, who used to hang out with us. I had not seen either of them for a while, but last time I was in Pattaya the deputy mamasan had been promoted to mamasan of a new bar. I had always had the hots for her, and one hour after I learned she was working in a new bar, I was leaving that same bar holding hands with the mamasan to the general applause of the girls. One hour later, I was stuck deep to the hilt in the mamasan’s lower intestine.

Shameless and oh! so proud of it.

The Sergeant

.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.

In those days also, ladyboys were allowed into the Nana disco (not any longer). One night I was staying at the Nana Hotel and a longtime lady barfine turned into a short time mistake, so after she left I went down to the disco by myself to forget about it. Some four or five of the Casanova ladyboys were there and were all over me the moment I came in.

I enjoyed the attention of being surrounded by the supermodel-tall, provocatively dressed ladyboys and bought them drinks and boisterously danced with all of them like we owned the dance floor. I could not resist showing off my dirty dancing moves and squeezing their boobs and spanking their asses for everyone in the disco to see that I was the man.

The ladyboys were clearly enjoying my attention and kept offering to stay with me for the night. Individually or in a group. Up to me. No charge, they said. Such an offer I could not refuse, and agreed to stay with one of them that I particularly fancied. I lowered expectations by telling her I was not sure what would happen once we got in the sack. No problem she said, very happy at being chosen over the other ladyboys, and deep-tongue-kissed me right there in the middle of the dance floor.

The farangs and Thai ladies opened a circle around us and applauded as we danced. I was somewhat uncomfortable, and put on a macho act by getting behind the ladyboy, bending her, and dance-pumping my pelvis against her ass. What I did not expect was that one of the other ladyboys sneaked up behind me and did the same to me. The crowd went wild…I let go and, for the first time in my life ladyboys made me feel exhilaratingly…shameless.

Once in the room, I did not really know how to go about it. So, I told her to take the customary pre-sex shower. She went in, but unlike the regular Thai ladies that come out afterwards wrapped in a towel, my ladyboy fling called me in to join her. I did as asked, and will never forget the sight of her dick hanging from a forest of dark, silky wet hair. She began to soap me and in less than 10 seconds (I swear) her dick was rock-hard and vertical. I hesitantly touched it, but could not overcome a feeling of revulsion at the contact (it was the first dick I had touched in my life, other than my own).

When we got to bed, I was still half-limp. She sucked me, but to no avail. I had hoped to fuck her in the ass, but began to accept that I was not going to get condom-hard (remember that I had short-timed a lady just a couple of hours earlier). Being fond of tit fucking, I positioned myself in her big plastic tits and pumped away. The ladyboy was begging me to fuck her in the proper place, but I still was not hard enough. She was very horny, and started sucking me again, while positioning herself for a 69, which I could not bring myself to engage on.

Eventually, I lay on my back and asked her to finish me with a handjob, while I fantasised about having sex with a farang lady acquaintance of mine. This way, I managed to orgasm and the ladyboy lovingly placed my cock in her mouth for a few minutes after. She remained stiff as can be, as she fingered her own asshole. She looked at me with begging eyes, and again I touched her cock, but it still felt weird. I was not ready to suck it, and even less to be fucked. The best I could do was get the towel and then stroked her cock through the towel until she came (which did not take long).

When it was all over, we both felt awkward at my reluctance and she politely left. She refused the 1,000 baht I tried to give her (but asked for it over one year later when I took another ladyboy from Casanova, but that’s another kinky story). I did not know what to think of that wild night of bungled sex first with a lady and then with a ladyboy and just went to sleep.

As you can see, my first ladyboy experience was not that great at the time, but now when I think about it I get very excited. In fact, some months later I would finally manage to fuck the farang lady I was fantasising about when the ladyboy was giving me the handjob and guess what? While I was fucking her, I was thinking of the ladyboy!

Like the proverbial first beer, a ladyboy is a taste to be acquired, and I would try again a few months later. Stay tuned for that account… In the meantime, it would be interesting to learn whether other readers’ own first experiences were great or not.”