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.

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.”