the third sex

Sargent Shameless must be getting old and sentimental.  Apparently my last posting, about the ladyboys who hoped for a relationship with me, has inspired the Sargent to share his own views.  It seems he can have post-ravaging feelings for his ladyboy conquests.   Who would have thought?  But it also seems he is even worse than we thought: not only he breaks their asses, he also breaks their hearts…
 
 
Anyone who thinks the Captain and I first met in a ladyboy orgy or anything wild like that is dead wrong.  The way it happened was that after coming across the bar scene in the Captain Outrageous site, I was so impressed with the Captain’s insights that I felt compelled to ask him for advice on how to deal with a  ladyboy who had fallen madly in love with me and I could not bring myself to let down. This particular ladyboy was arguably the most beautiful ladyboy in all of Thailand at the time and her pics are still all over the internet (although incredibly not on Captain O!).  When she told me that she loved me like she had never loved any other man, I could not but accept to be her boyfriend (or something like that).  To delay the inevitable breakup, I stopped playing around in Bangkok (where she was based) and would go to Pattaya, Phuket, etc without her knowing.
 
While often ladyboys (and ladies) have faked such passion for me with a view to material reward, a few times it happened for real as they, for whatever reasons, put all their hopes of redemption and womanly acceptance in me.  Although I don’t seek to trick them into loving me, it feels rewarding for my ego and greatly intensifies the ladyboy experience I seek both in and out of the sack.
 
Unlike the Captain I don’t live in Thailand so usually the separation takes care of the infatuation. I have gotten used to lovestruck ladyboys crying while making love to me on our last night together, but then they go back to their realities and I to mine.  But a few ladyboys do wait for me to come back, which makes separating again even harder.  This is what happened with that internet superstar who claimed she had all kinds of suitors ready to take her as a wife and could not accept that I would not.  She did wait for me for about two years of sporadic visits, but eventually she realised I was not the prince charming she wanted me to be and let go. By then she was no longer the same sweetie who fell for me and started doing all kinds of hardcore shoots for the most tasteless ladyboy sites, perhaps to get back at me.
 
I had another case with a really special Phuket ladyboy who I was crazy about, but who initially did not particularly care about me.  We hooked up again three years later and spent a week together and afterward she decided to quit the bar life and called me and, in what was one of the most heartbreaking conversations I ever had, said I was the nicest man she ever met in her life and that she loved me.  She said she was contemplating suicide and wanted me to know that.  I tried to cheer her up and said I would visit her again in a few months (which I did!).  Eventually she came to accept her life and is now back in Issan helping with the farm.
 
I also hooked up for a while with a ladyboy who was very passionate and so understanding of my need for sexual variety that she would help me set up threesomes with other ladyboys as long as I only slept alone with her  (The Captain says: That’s the Sargent we know!).  I never realised she really loved me until the day she caught me alone having breakfast with another ladyboy.  That night she asked for some glamour photos back, told me I had broken her heart and left my life. I never felt like such a lowlife.
 
There was also this ladyboy who when she first came on the Cascade scene at 18 was the toast of Bangkok.  But she had one of those exotic looks that does not age well and at 22 when I finally hooked up with her she was no longer top choice.  She turned out to be a very considerate and energetic lover and I definitely felt good with her.  Although she did not fall in love with me, she told me that nothing came of all the love promises from the other men she was ready to give her heart to.  She said many told her they loved her but never even called once afterwards. She said this in a sad, accepting way that was disconcerting to hear.
More recently, I met this quite special ladyboy in Pattaya who (at 22) is madly in love with me, wants to talk to me everyday and says that, because of me, she left Pattaya and is now working as a clerk at a bank in BKK. I have decided that on my next trip to Thailand I will seek her and stay with her the whole time. The end result will likely be the same, but at least I will have given her a little more time to grow up.
 
I could go on and on with so many of the ladyboys I have met, especially the Filipinas who have a Latin passion to them and have even less social acceptance and income opportunities than the Thais and thus are prone to fall big and fast for the first decent guy they meet. I guess, like everybody, ladyboys want to be loved for who they are and the fact that they are a cross-gender makes finding such accepting love even harder than for the rest of us.
 
So what did the Captain advise me to do when I wrote to him to ask about having my cake and eating it too?  “Keep spreading yourself” he said “like you have been doing.”  I remember thinking of the guy in Casablanca saying “I think this is the beginning of a beautiful friendship…”