Before I made a final decision some years back just before Valentine’s Day to join MyLadyboyCupid, I did my homework. After all, if I was wanting to date a Ladyboy, I felt the best thing to do was understand more about what it means to be Transgender. Many Trans attracted men just see the beauty, charm, and feminine grace of Ladyboys, but I wanted to know as much as I could about their mindset and the life challenges they face. Plus, maybe have someone special in my life for the special day of love, Valentine’s Day.

I like to know people well before committing to any relationship. You see, my basic plan was to find a Ladyboy who was compatible with me for the long term so that we could enjoy quality time together. Just like one would with a prospective fiancé or wife.

Ladyboys love the romance of Valentine’s Day

I read as much as I could about pre-puberty blockers, the different types of hormones Trans women take, and the effects thereof. I’d heard that many Ladyboys are susceptible to mood swings, although not as bad as genetic women. I also heard that they have a higher sex drive than natural women, but I’ll come back to that later. So, all in all, I researched quite a lot about Trans matters.

By the time I met Orr, a Ladyboy from Khon Kaen in the northeast of Thailand, on the dating site, I was becoming quite an expert on all matters to do with Ladyboys. I found that many are hopeless romantics. Hence their love of special days such as Valentine’s Day. Many dreams of finding a long-term partner on this special day of romance and love.

Yet, it wasn’t until I went to some of the clubs in my home city where I knew Ladyboys congregate that my knowledge was more complete. I had no intention of dating any of the Ladyboys I met around town, I just wanted to meet some Trans women in person. This gave me a much better perspective on the trial and tribulations they face in everyday life.

Being a member of MyLadyboyCupid helped and, over months, I chatted on and off to numerous Ladyboys. Some were clearly never going to turn into lovers or long-term companions but they were fun to talk with. And very helpful when I asked questions. I did, however, steer clear about matters to do with sex as learned early on that there is no one type of Ladyboy. Yes, they may all be Transgender, but their sexuality can vary dramatically.

I know many Trans attracted men have high hopes of meeting a special Ladyboy on Valentine’s Day for some romance and love. For all those men planning to do so, I’d suggest it’s best to understand some more about the physical changes some Ladyboys go through—and also some of those they don’t. Then you’ll know the right thing to do when matters turn to the bedroom.

Ladyboys exist in a myriad of variations

I’ll keep it short. You need to know that some Ladyboys only take hormones to feminize themselves and don’t have any major surgeries. Well, that is except for some facial cosmetic surgery which a high proportion of Ladyboys has. Hormones will, typically, stimulate some natural breast growth and help redistribute fat to the bottom and hips of Trans-Pinay, giving them a womanlier shape.

Then there are Ladyboys who have breast implants or breast augmentation but keep their penis. They may keep their penis for use in sexual activity or for other reasons. These may be financial (ie can’t afford the operation) or social or religious as they don’t believe one should remove any body parts.

The end result: we have Ladyboys who look just like beautiful, even stunning, women. Longhair, very feminine shape and is wonderfully made-up. Until they are naked that is! But just because they still have a penis doesn’t mean they can or want to use it. nor does it mean they are gay. Some Ladyboys only like men as they see themselves as nothing more than women. Some like men or women as sex partners. Others like and are in relationships with only women.

But let’s go back to Orr, my girlfriend. I see her as just another woman, albeit a very beautiful charming, and feminine one. You really wouldn’t know by just looking at her that she is Transgender. Over time, as we dated more regularly and I gradually got to know her better, we began to get more intimate. At first, it was just holding hands and then kissing. The kissing became more passionate.

The sexuality of Ladyboys is varied

However, I deliberately tried not to push the sex angle too quickly, even though I wanted to. I wanted to be sure that she was the right Ladyboy for me, especially as it was my first experience with a Trans woman. But, I also, wanted Or to know that I genuinely cared for her and it was not just all about sex.

Finally, Valentine’s Day arrived and Orr agreed to stay overnight at my apartment. Our passions were running high and I found it hard to control myself. After rolling around on the floor for a while, Orr whispered to me, “Neil…, I still have a penis you know.”

I’d sort of guessed but took this final revelation in my stride. “Yes Orr, I know, that’s fine by me,” I whispered back. “I love you for being you, not for what’s between your legs.”

Our sex life is very varied and it depends on what both of us feel like at the time we make love. All I’m grateful for is that Orr is still the same person as when I first met her through MyLadyboyCupid almost three years ago on Valentine’s Day!


Just an average guy and admin of MyLadyboyCupid.