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Sexual roles in Ladyboy dating

Maki Gingoyon
This post was last updated on .

If you’re new to this type of dating, your thoughts are still probably unhinged when it comes to having sex with ladyboys. Today’s topic is a little NSFW so I highly recommend for you to read it in utmost privacy.

Which role to play when having sex with ladyboys ?

If you’re planning to have sex with a ladyboy, it’s vital for you to understand the different sexual roles first. There are a LOT of sexual roles in the world of ladyboy dating and this is why it’s truly exciting to date women like us. Just like what Hannah Montana said in her song’s lyrics,

“You get the best of both worlds!”.

Frequently Ask Questions about Sex with Ladyboys

If you’re still in the premise of having your first-time sex with a ladyboy, you’re going to come across terms such as:

  • vers-bottom
  • top
  • bottom
  • vers
  • vers-top
  • and more.

It will be quite confusing but we will get to it in an easy-to-digest breakdown.

ladyboy on bed

There are a lot of things that first-timers want to demystify. I don’t blame you. If I were a guy who’s just starting to have an affinity towards ladyboys, I’d have a lot of questions too. For now, let’s answer the most frequently asked questions when it comes to having sex with ladyboys.

What is a Vers Bottom?

Vers-bottom means a person who is mostly on the receiving end when it comes to penetration, yet is amenable to doing the penetrating as well.

Vers was used as an adjective because the main subject that best describe’s this person’s preference when it comes to sex, is being a “bottom”.

couple in bed

Albeit being okay with topping from time to time, this type of ladyboy will highly-likely be more satisfied if she’s the one who’s bending over. But from time to time, she will also relish the moment of entering your anus.

The perfect match for a ladyboy like this is somebody who’s vers-top.

Does having sex with ladyboys make you gay ?

First of all, let’s get into the nitty-gritty of what the definition of what gay men are.

A gay man is a cisgender male who prefers to have sexual engagements with MEN.

Do you think that ladyboys are men ? If you’ve answered no, then you’re not gay.

straight guy

However, if you’ve answered the other option, you’re still not gay. You know why? Because vers men who are straight exist. Moreover, what you think of yourself does not define and validate a ladyboy’s womanhood.

By thinking that you’re gay because you’re planning to have sex with a ladyboy, you’re not only further confusing yourself. You’re also putting ladyboys’ gender identities in a state of reduction.

You see, when you have sex with ladyboys, you’re going to operate a penis and a butthole. You’re not going to operate a vagina. If the latter makes you feel more of a man and is the only way to validate that you’re indeed a man, you’re better off playing with a pussy.

Three Sexual roles in Ladyboy Dating

It is quite funny to talk about this but admit it, it is interesting and also exciting. I would like to get more intimate and tackle sex or making love (as what I prefer to call it) which is one of the most essential parts of a relationship.

men sex with ladyboy

Sexually Compatibility is IMPORTANT

Being sexually compatible is one factor that would help you build a happier relationship. It also opens up a world of more diverse sexual positions. Few online ladyboy dating sites include sexual roles as part of one’s profile information. So what is this sexual role all about?

This sexual role would somehow, determine if you are sexually compatible with the ladyboy that you are dating. So take a deep breath and let’s dive into these various sexual roles.

 1) Top

This role is very common to the gentlemen. Being top means, you are the one in charge of penetrating your partner.

If you choose top as a sexual role, this means that you are sexually aroused and pleased every time that you penetrate your partner.

couple during top sex

The penetration that I am talking about is when a male genitalia enters the anus. This sexual role is not only limited to your male partner; for there are ladyboys who are mostly non-op transsexuals that prefer to be top.

 2) Bottom

Basically, this is the opposite of the top. If you are bottom, then it is you who’s on the receiving end.

When you find receiving your partner’s penis through your anus pleasurable, then that means you are bottom. Regardless of position, if you are the one being penetrated by your partner, then you are bottom.

bottom sexual relation

This sexual role is very common to ladyboys, although there are a few men who are sexually aroused and pleased being bottoms, but they are very few. Having a boyfriend who is bottom is not bad after all as long as you are top. That’s one great example of a sexually-compatible couple.

 3) Versatile

This is a combination of being top and bottom.

You are versatile when your sexual behavior finds pleasure whether you top or bottom.

You are the type of person who is very flexible and don’t mind whether you are penetrating, or being penetrated.

versatile sexual relation

So those are the three sexual roles that usually apply in dating a ladyboy. I believe that by understanding what these sexual roles are all about, your search will be a lot easier.

Sexual roles are not determining factors on why you fall for someone, but rather, one of the few important elements that makes a relationship satisfying.

How can I please my Ladyboy Partner?

There are many ways in making a ladyboy explode. This is going to get quite graphic so if you’re not alone, again, stop reading.

Oral Fixation

Yes, this is a fool-proof way of pleasing a ladyboy (unless she doesn’t like her penis). When you suck a girltoy, don’t just put 1 foot forward, give it your all. There’s really no secret to a great blowjob. I’m going to share with you a step-by-step guide on how to give a good blowjob.

oral sexual practices

No teeth

This is quite important if you’re sucking a girltoy. You can do this by folding your teeth inwards to cover your pearly whites. Nothing is more annoying than a half-hearted blowjob. While you’re at it, suck it like your mouth is a vacuum cleaner as well.

Tongue Twister

You can take this to the next level if you use your tongue as well while in the process of pleasing your ladyboy partner. There’s no greater tactile sensation than something wet and warm. While you bob up and down, swirl your tongue ever so gently and trust me, she’s going to think that your mouth is a sucking machine.


If you want her to say “I do” after just 1 night of getting her into bed, you HAVE to master your gag reflex. You see, if you’re able to take all of her girltoy from the head down to the base of the shaft, you will truly score a lot of pleasure points from her.

You have a penis and I’m pretty sure that you know what I’m talking about. Deep-throating is a skill and it needs practice. My advice would be for you to keep your throat lubricated and don’t eat 3 hours before doing the deed. If you eat just before you suck a penis, you will be vulnerable to regurgitation and we all know that a pile of puke is so not sexy.

Let’s Play Ball

Some people have very sensitive balls. Some men like getting “ball-jobs” so in order to do this flawlessly, just apply the same principles that are listed above this one.

Breast Friend

Most ladyboys are undergoing hormone replacement therapy which may cause most of them to have very sensitive nipples. You have to capitalize on this knowledge and I’m going to share with you some of the ways on how to unlock the treasures from her chest.

Breast under shower


Soft bites are very hot. Nipple play is one of the best ways to awaken her senses. This will depend on what your partner likes so doing both would be the best method to know what she likes.

Sometimes, people don’t know what they like until you do it to them. In the bedroom, remember the sage words “Spray It, Don’t Say It”. Sex is one of the very few activities in life wherein silence is truly appreciated.

Nothing is more off-putting than a man who keeps probing what he’s going to do or is clueless about what he’s doing. Just do it ! However, don’t go all out into biting it like you’re going to decapitate her. You can also apply this nibble technique for her balls and the shaft of her penis.

Squeeze it like Lemons

Yes, you should do this when you’re cupping her breasts. Don’t just hold it without passion. Mold it like it’s clay or play-doh. Pinch the nipples while you’re at it as well. Sky’s the limit when you’re squeezing the tits.

Eat it Like Groceries

You’re hungry and this is all that you have to remember when you’re pleasuring your ladyboy partner’s breasts. Make sure that your mouth is always wide-open for such an undertaking. Don’t hold back, just EAT it.


Ahh… the magnificent buns. The place where all of the magic happens. This is the Disneyland of sex with ladyboys. If you want to successfully navigate into the world of ladyboy dating, you have to be equipped with great ass-play skills.

ass close up


Yes, This is very important when it comes to anal sex. There’s no anal sex if there’s no proper rhythm. If you’re on the giving end, you have to know what rhythm your partner’s most compatible with. Not everyone enjoys getting fucked by a Jack Rabbit. Some ladyboys prefer it nice and slow.

Squeeze em Buns

Just like what was mentioned in the breast section, you have to squeeze the buns. If you figure out how to multitask and apply all of the tips in oral sex that I’ve shared with you while squeezing her buns, she will EXPLODE.

Lick it like a Lollipop

Lick her hole. Don’t have 2nd thoughts about it. Lick it like you’re performing cunnilingus. Bite the cheeks while you’re at it as well.


Before you enter your partner’s womanhood, you have to relax it first. Treat it with utmost respect. However, don’t just perform this one like it’s menial labor. Lubricate your fingers and reach through the depths of her anus until she moans of satisfaction once you hit her g-spot.

There’s still a lot of tips that I want to share with you to achieve the best sexual encounter. However, this is going to be a novella if I did that.

Posted in Love & dating

About the author

Maki Gingoyon
Mabuhay! I am a Filipino transgender woman who believes that making friends with, or dating and loving a transgender woman should not be ashamed of.

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4 thoughts on “Sexual roles in Ladyboy dating

  1. I can’t believe no one is discussing this subject because if it isn’t somewhere on you mind you probably aren’t human. I am pretty new to this site but not new to the World of the Ladyboy. When I see the line that says “Sexual Role” I immediately wonder about different degrees of Sexual Role. The clearest and most easy to understand is “Bottom.” i believe this means the LB wants always to be treated like a woman and have love made to her. When I see “Top” I wonder if this LB is aggressive, just likes to take a dominant role,,or does not enjoy penetration herself. Lots of questions arise here as to just how “Top” is this person. The third is “Versatile.” This is my personal favorite and the vaguest of the three ares. When a LB says she is Versatile does this mean she likes to give and receive, does it mean she will give but would rather receive, or that she truly loves all the pleasures that mutual sex can deliver. It is not the initial impact of the “Sexual Role” category that I would question, but the vagueries of each are that sets my mind to wonder. What do you think? I wouldn’t mind know what the facts and perceptions are fro either men who love Ladyboys or especially from the Ladies themselves

  2. I have found that tgirls use versatile in two different ways. One means they can be both dominant or submissive but are otherwise traditional bottoms in that they will only be penetrated. Others use it to mean the enjoy both penetrating (top) and being penetrated (bottom). The only way to know is to ask. Personally, I think most transoriented men are also versatile to some degree. I generally prefer the role of a top, I am a hetero male, after all. But with the right partner, I find the bottom role to be very pleasing. I want my partner to be happy too, and if she wants to top me on occasion, it can be very intimate and rewarding. I am mainly a top. A versatile top I guess.

  3. Actually I prefer my dates to be versatile, I get great pleasure from giving oral and being bottom. i’m lucky that the ladboys I date are happy to oblige, one is only into topping and receiving oral, she likes ass play but not being penetrated. Having a ladyboy who is bottom only gets a bit boring, but plenty of guys like that..

  4. I not long ago started relationship with Filipino Ladyboy. I like her personality. Hopefully relationship goes well. She is versatile sexualy. Also she much younger than myself. She seems to get easily aroused sexualy. I am not complaining. Though she is very pretty in looks, I just finding it sometimes difficult to please her sexualy every day. As she usually wants me to bottom and most days several times. Don’t get me wrong, though I am feeling the age barrier can be a problem, especially when it involves sex.

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