“Shemale Dating” – The Best Sites to meet Trannies, TS Girls and Ladyboys

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  • Top-tier casual trans dating services
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Disclaimer: We are well aware of the difference between trans people, transsexual women, ladyboys and the rather problematic term “shemale”. Datingroo distances itself in every form from discriminatory language and ideology. In this text, however, we would like to address all those who want to have a casual relationship with a trans person and who are looking for a suitable partner on so-called “shemale dating sites”.

If you’re looking for LGBTQ+-friendly dating apps for serious relationships, then check out our trans*-dating sites category.

Have you ever dreamed of spending a night with someone who unites the best features of both sexes? Then you may be one of many who wish to date a trans lady.

However, it can take a lot of courage to put yourself out there. In addition, knowing which is the best UK based transgender dating site for you can take a lot of research.

Fortunately, we’ve done it for you. 

What can you expect from Shemale Dating Sites?

  1. Acceptance

    While attitudes towards trans* men and women are slowly changing, men who fancy their uniqueness are still frowned upon.

    The rising numbers of users signing up on ts dating websites are the best evidence for that. On an adult service like MyTranssexualDate – which has an average of 25 million page views a month – you’re going to find millions of likeminded users looking for the same as you – a good time with a woman that ticks all your boxes.
    Within the online community, no one is going to judge you.
  1. Discretion

    Although there is no reason to be ashamed, you may want to keep your TS dating experience private.

    Most services will make sure, that your data is protected at all times, whether it is through private messaging or an anonymous profile page.

    Especially if you decide to subscribe to a premium membership, there’s plenty of possibilities to be in charge of who will find you and who won’t.
  1. Variety of Potential Matches

    Are you looking for a date with a ts girl of a certain ethnicity? Do you want to start off your casual adventure with Thai ladyboys (Kathoey), Filipina transsexuals or a someone from Brazil ?

    Use the filter function. Many dating websites allow you to specify your search with the help of filters to help you find the exotic shemale of your dreams.

    You can find legitimate tranny hookups from all over the world. But keep in mind that there are also local ladies eagerly waiting to meet up.
asian trans woman wearing elegant coat
  1. Safety

    Online dating services will have helpful tips on how to protect yourself from a potential scam. They will have verified the identity of their users to make sure you don’t end up with a fraud.

    While you can be assured that most members of the website are genuinely looking for dates and hook-ups, there are definitely some red flags you might look out for.

    For example, if your match keeps coming up with excuses why you should not meet up in person or talk on the phone, you should hear your alarm bells go off.

    If they suggest continuing to chat on another site, be suspicious and remember: As long as you remain on your dating site of choice, you’re in a safe place.

    And last but not least, if their profile disappears out of no reason and then messages you with a different profile, you should be careful. Your match might not be real.

    In case of doubt, there’s always the opportunity to report a user and let the people who run the site do the rest.

Click here for more Tips and guides on Transgender Dating.

How to choose the right TS dating site

The short answer is the one where you feel most welcome, least judged, and free to be who you are, whether you’re part of the LGBTQ+ community or not.

On most dating sites like MyLadyboyDate or MyTransgenderCupid, there are plenty of t-girls who are looking for hookups and dates with cisgender men.

However, there are a few things to keep an eye out for.

  • See if the sites that interest you offer free membership. While certain services, such as messaging, might not be included, it’s a great way to get a ‘feel’ for a site and see if you like what’s on offer.
  • Some sites offer chatrooms to non-paying members as part of their free services. These are a great way to get to know other users, without the pressure of dating. Investigate the sort of people who use the site and you’ll get a good idea whether it’s for you.
  • Check out the site’s etiquette policies. A good site will give you clear instructions on how to block or report users whose behaviour you find offensive or inappropriate.
  • Ensure that payments are encoded and encrypted. When taking out a subscription, you want to be sure that your financial details are safe and secure.

Want to get to know the trans celebrity activists paving the way for other trans people? Read our article here to find out!

young transgender woman with neon hair

Tips for dating a trans woman

The first thing to realise is that dating a trans person is just the same as dating anyone else. However, there are a few things that are common among the community, and it pays to familiarise yourself with some of the basics.

  • Educate yourself. The person you are connecting with wants to go on a date with you and doesn’t want to host a talk on transsexuality. Do your homework, before you meet. The best services offer sound information about all necessary questions you might have, and it’s worth reading thoroughly before you go any further in order to avoid microaggressions.
  • Check which pronouns they prefer, such as ‘him’ or ‘her’. You can do this through sites that offer private messaging. It’s also worth asking how comfortable they are with physical contact, in case things level up.
  • In fact, terms like “shemale” or “ladyboy” are pretty frowned upon by most members of the community and we only use them here with a bitter taste on our tongue. Respect them not wanting to be called names like that and be understanding if your date reacts dismissively to these labels. You should make sure that you are not offending anyone.
  • Be prepared for others to have opinions. If you end up in a relationship, other people are going to have opinions and some of them might be surprising or even offensive.
  • Dating a transgender person is no longer taboo and there’s no reason you should feel anything other than good about it.
  • If you are dating someone who has yet to undergo surgery or just beginning a course of hormone treatment, be aware that their bodies may change.
  • Treat your “shemale” like a lady & with respect. These ladies have chosen to live as a woman, but they may be confronted with rejection and discrimination in public. Which is why you should go out of your way to treat her right. Shower her with compliments, show her how attractive you find her; and you will certainly get rewarded for that.

Who’s waiting for you on Shemale Dating Sites?

A who’s who

If you’re one of the growing number of people for whom a potential partner’s sexual identity isn’t an issue, then finding the best TS dating sites or apps in the UK is a great way to meet new people.

Before you sign up, you have to be clear about what you’re looking for and who you want to meet on these platforms.

Are you determined to just live out your sexual fantasies with a shemale or go on actual rendezvous with a tranny? Or maybe a ladyboy escort service is the right one for you. Chose the site that appeals most to your desires.

To help you ease yourself into this world, we’ve compiled a handy guide.

Sensual Blonde Woman Posing Wearing Sexy Lingerie.

Transgender or transsexual?

These two terms are often confused and used incorrectly. Transgenders are those who feel that they were born into the wrong bodies. You might see someone who appears, physically to be a man, but identifies as a woman.

Similarly, you may meet someone who, outwardly, ticks all the female boxes but on the inside identifies as being a man. People who are transgender are those who don’t identify with their birth-gender but haven’t felt the need to physically change it.

Transsexual men and women are those who feel the need to change their sex on a physical level. This can mean taking hormones, dressing as the sex they identify as and, ultimately, male-to-female or female-to-male surgery.

It’s not uncommon to encounter trans* who have begun the transition but haven’t undergone gender-reassignment surgery. While you might hear the terms ‘pre-op-male-to-female’ or ‘pre-op-female-to-male’, these are generally not used in LGBTQ+ circles.

Similarly, you may hear the terms ‘post-op-male-to-female’ or ‘post-op-female-to-male’, they are just as outdated. Those who have undergone gender reassignment surgery may refer to themselves as ‘trans’ but may also refer to themselves using the nouns that fit their new sex.


Again, this another commonly-misused term, often confused with the trans community. Transvestites are cross-dressing men and women. The majority are male, but the term can be used to describe either sex.

Another piece of misinformation is that crossdressers are all gay. The truth is that they are just as likely to be straight, bi, queer, or lesbian as they are to be gay. Transvestitism is not a reflection on a person’s sexuality.

They like to wear clothing that’s conventionally regarded as being for the opposite gender. They do this for a variety of reasons. It can be that they feel more comfortable in that clothing or that they feel a release of stress from the pressure of their traditional roles.

Whatever the reasons, transvestitism is not a mental illness, but a normal part of human behaviour.


Last but not least, ladyboys are trans* women, mostly from the Southeast Asian area, ready to enjoy a fun time with you for just a little extra top.

Ladyboys appear like full-fleshed women while they often keep their birth-sex. The term is often used alongside “shemales”.

They are not to be confused with Femboys – men who aspire to look overtly feminine by, for instance, wearing make-up or androgynous clothing.

Staying safe online

No matter which dating sites you use, there are always scammers and fakes lurking in the shadows. Here are a few tips to help you maintain your online safety.

  • When creating a username, never incorporate any personal information, such as your phone number, date of birth or address.
  • Never feel pressured into giving out personal or banking details by another user.
  • If the site you’re using offers to create a password for you, accept this and store it in your browser. These are designed to be harder to crack than the passwords most of us come up with.

FAQ: Transgender Dating

Get answers to your burning transgender dating questions here. Feel better prepared when chatting up a potential transgender partner with the answers below.

Where can I find a shemale dating site?

You can find shemale dating site recommendations right at the start of this page. You can also find reviews of trans dating sites or apps below this FAQ in addition to more information on free TS dating site options.

How do I start talking to a transgender person online?

You can start talking to a trans person by telling them what caught your eye in their profile. It could be anything from saying something nice about their photo to asking about interests they’ve listed on their page. 

The bottom line is that you’re starting a conversation with someone you find attractive. You want to show that you are positively interested in them as a unique person.

What is it like dating a shemale?

There is no single answer to what dating a shemale is like for everyone. The best way of thinking about dating a transgender partner is to take gender out of the equation – along with the word “shemale”, while you’re at it.

Think about what dating is like for you. What are the things you value in a relationship? What does a wonderful date entail in your mind? Once you’ve answered those questions for yourself, you will have the answer to what dating a trans person can be like.

If you are thinking about what TS dating is like in terms of those around you, then have a look at the answers below.

What is my sexual orientation if I’m dating transgender people?

What your sexual orientation is or isn’t if you’re dating transgender people is something only you decide. You also don’t need to have an answer right away. It is completely normal not to know or to be unsure. You are under no obligation to define your sexual orientation for other people. 

If you are wondering about your sexual orientation, it’s worth finding reliable LGBTQ resources, such as GLAAD UK and the LGBT Foundation. You can also speak to supportive people you trust to help you find your very own answer.

How do I introduce my transgender date to friends and family?

You introduce your transgender date to friends and family like you would anyone else you’ve introduced before. You give your date’s name and maybe some brief details about how you met. The fact that your date is trans does not change social norms or expectations of politeness. 

If for some reason you cannot expect basic decency from your friends and family, this is something you must discuss with your date to figure out what to do.

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