Ladyboys talk about intimacy

One night recently I had dinner in Phuket, Thailand with two of my close friends, Mony and Cat, both of whom belong to MyLadyboyCupid. None of us drink alcohol but we were all in a good mood and have some fun. Somehow, somewhere along the way the “girl-talk” conversation turned to sex. Personal and private I know it should be. But, hey, Trans girls share some of their “best kept” sex secrets with other Ladyboys. Just like genetic women do.

Not that we shared anything revealing about the men we’ve enjoyed sexual relations with in the past. No, the conversation was more to do with the fact that there are so many variations even amongstLadyboys about what we like to get up to in bed. We puzzled on this for a while but kept coming back to the fact that gender is a spectrum. As is a sexual preference. So, just because a girl happens to be a Ladyboy you can’t automatically say she likes men. And you can’t conclusively say her “tastes” won’t change as she spends a long time on female hormones. Both gender and sexuality are really a rainbow with the edges of the colors blurring into each other. Just like the likes and dislikes of Transgender women when it comes to things that happen in the bedroom!  

Different Ladyboys have different sexual needs

The conversation went something like this. I’ve cut out some of the more graphic things we talked about but you can use your imagination as you wish!

Me (Lek): Well, I’m the youngest T-girl here, so I think Mony should start first. She must have more experience than me and Cat!

Mony: Hey, that’s not fair! All Ladyboys have the same sort of sexual experiences, right? You go first, Lek….

Me: No, I’m shy!

When I was in my teens, I’d had been cross-dressing for a while, you know wearing women’s clothes.


Cat: I’ll start as there isn’t that much to tell. And, in fact, Mony, I think you’ll find that we all have different ideas of what we like in bed! Anyway, to be honest, I think I was a little unusual. When I was in my teens, I’d had been cross-dressing for a while, you know wearing women’s clothes. I’d present like a woman whenever I could. But I had no idea I was a fully-fledged Ladyboy.

In fact, in reality, I was very confused. Many genetic girls seemed to find me attractive and I had no shortage of girlfriends when I was between about 14-17. I have to admit I regular had sex with many of them. Some of it was just fondling their breasts or touching and stroking their vagina and making them orgasm. But there were quite a few occasions when I had penetrative sex with girls. Whilst wearing a condom I would add!

Ladyboys come in all shapes and sizes

Mony (interrupting): Wow, Cat you do surprise me. Didn’t you know you were a Trans woman by the time you were 17 or so? I knew from the time I was about 8 or 9. Well, I knew I wasn’t a “straight” man at least.

Cat: Hmmph…, as I said I was confused. I didn’t really know if I liked girls because of sex or because I wanted to be like them. I always loved their clothes, accessories, make-up and perfume. But I guess I just sort of thought dressing and presenting as a female might be just a phase. I never had sex with a boy or man during this time. In fact, I definitely would have said “no” had the opportunity arisen.

Me: But now is different right?

Cat: Yes, totally. But I did wait until I’d had my breast implants and gender confirmation surgery with my own vagina before I slept with any man. And now, I’m just like any other woman. I like being penetrated but not anally. I’ve tried it and it hurts. And it’s not something I need to do a I am a complete woman who can orgasm if the situation is right!

Mony: Well you are completely different to me (laughs). Completely. I’d had 2 or 3 boyfriends when I was still at school. I must have been 13 or 14 and we used to sneak off into the woods or go to someone’s house if we knew no adults were home. We’d either masturbate each other or sometimes have anal sex. Even then I liked to dress up as a girl and once or twice I had sex with boys with me wearing a bra and panties or a nightdress. Once I even managed to find some stockings and suspenders and a negligee to wear and my “boyfriend” was so turned on he had an orgasm twice in a few minutes!

Me: Well, things have never really changed for you Mony, have they? You told me you still have your penis, right?

Mony: Oh yes. It’s a very important part of sex for many of the men I have met on MyLadyboyCupid. Oh…, but please don’t think I sleep with anyone. I have had two long-term relationships with men I met on the dating site. Both times they only ended as the men had to go back overseas and I couldn’t get a visa to follow them. Pity.

In fact, my current boyfriend says that he will not let me cut my penis off even if I wanted to. He says that what make Trans women so interesting. We look like women, feel like a woman, but can offer the option of sex like a man! Ha, ha, I like that saying! 

Cat: What about you Lek, tell us about some of your experiences.

Me: Oh…., is that time. I promised to message my new boyfriend from MyLadyboyCupid at 8.00pm. I’ll tell you next time!

My Ladyboy Cupid

Just an average guy and admin of MyLadyboyCupid.