A conversation with two ladyboys

Hi Janie, I saw your profile on iDateLadyboys. I have to say you look amazing, so beautiful. I especially I like the photo of you sitting on the rock at the beach and wearing a pink crop top. Sensational! By the way is that Cebu in The Philippines?

I’ve always been interested in getting to know a Ladyboy but, until recently, I was living in a fairly small city in the US which limited my opportunities. That was, until I found iDateLadyboys with all of the wonderful T-girls as members.

Hope you have the time to write back and wait to hear from you, Ken.


H Ken, thanks for your mail nice to hear from you. Thanks also for your compliment, it’s always nice for a woman, whether a Ladyboy, Trans-pinay or genetic, to hear a man say something good about them! Can you tell me a little more about yourself? I’ll be happy to answer any (reasonable) questions if you have them.

May I ask, are you looking for friendship or a long-term relationship?


Janie, thanks for replying so quickly. Sorry, I should have included some more information about me in my last message. I’m a 50-year-old divorcee with no children. I work in the technology industry and am hoping to retire in about five years.

It might sound like a cliché but I’ve always wanted to get to know a Ladyboy, hopefully, date her and enjoy a long-term relationship. I can’t really explain why other than that I find Transgender women to be more feminine and generally take better care of themselves than genetic women. To be honest, one of my online friends joined the website about three months ago and he recommends it to me. He is currently dating a T-girl from Manila.

I’ve done some “homework” and know about the differences in different Ladyboys in terms of their transition status, outlook on gender and, indeed, sexuality. But don’t get me wrong, I am looking first and foremost for a Trans woman I am attracted to and can get along with. Her actual gender status or sexuality is of secondary importance to me.

Find your date or true love on iDate Ladyboy – The not so ordinary dating site

Reading this back again I see I have not really said much about me. Well I am a vegetarian, fit and healthy and love most sports and hiking. I like to go to the cinema and read as well as trying to improve my cooking!

Hope this all helps and await your further reply.

Best, Ken


Thanks, Ken, for your information. There are a couple of coincidences in there. I am a vegetarian too and also enjoy cooking. Sports also appeal to me, albeit that I am more of a spectator than a participant. But I do love jogging/running and hiking.

Glad to hear that you have a reasonably good understanding of Ladyboys and know that we are not all the same. I don’t mind to tell you that I am post-op. I had my final surgery just over a year ago. However, I have waited until such time as all was healed and I felt confident enough to look for a man to date.

I have known since I was really very young that I was female and am proud that I have achieved my dream of becoming a woman. It has not been easy but I live and work and present as a female full time. I have even changed all of the necessary supporting documentation—and there is a lot of this!

The other coincidence is that I too work in the technology industry. I am video games designer having graduated with a very good science-based degree from a major University in The Philippines.

Hope to hear more. By the way, you do not look your age!


Janie, thanks, I was eagerly waiting for your reply. I kept looking at my inbox every few minutes. It seems that we have quite a lot in common! I sort of always knew that I’d meet the right Transgender woman on a dating site like this. Going to bars and nightclubs is not my scene. Plus, the chance of finding a nice Trans woman, or any other woman for that matter, is very difficult nowadays, especially in the city where I live. I actually enjoy being able to connect via a dating site, it’s so quick and easy. We can talk all night on line if we wanted to!

I run a software design company which I co-founded about ten years ago. It’s interesting that you are in tech too, especially in the video game design business which is a very big growth industry in Asia. I realize I didn’t tell you which city I am currently living it, it’s actually Singapore and I have an ex-pat there. Do you get up to this part of the world at all?

I don’t wish to be forward but it would be lovely to meet you and talk some more, get to know each other better. If you have any more photos, I’d really appreciate them. As I said in my first message, you really are very attractive. I think we have enough in common to have the basis for something more than just chatting on iDateLadyboys and hope you feel the same.

I am happy to answer any more question you may have or even send you some more photos of me if you want them!

Await your next reply.


Ken, I travel to Singapore every eight weeks or so on business! Next time will be around November 15th. Will you be in town then? Take care, Janie…