Dating sites and match searches for men and women
Dating sites and match searches for men and women

Finding the Best Crossdresser Dating Sites to Join

Crossdressing is one of the most exciting ways of spicing up the bedroom. Whether it’s putting on a piece of women’s clothing or enjoying someone who does, it can transform even the simplest, vanilla love-making into something more passionate, risqué, and sexy. But mainstream dating sites and apps aren’t equipped with helping you find someone who appreciates this niche form of dating. In truth, cross-dressing often has a negative reputation in dating, where people assume it makes a man gay. But as we know, there are many layers to cross-dressing, all of which can help turn the dial-up in your love life. For that reason, we’ve hand-picked 5 of the best crossdresser dating sites for you to try. Each one is free to join and has a thriving community of crossdressers waiting to be messaged!

logo Lesbiedates


With an inviting community and user-friendly design, it’s easy to understand why LesbieDates is the go-to destination for lesbians, bicurious women, and crossdressers. And with matchmaking features aplenty, you’ll be able to make connections almost immediately.
logo Buddygays


As the premier free-LGBT dating site, BuddyGays does it all! Perfect for gay, bisexual, and curious singles, this site is mobile-optimized and offers several advanced chat features that make talking to crossdressers simple, fun, and rewarding.
logo Together2Night


With instant messaging features and fun, flirty matchmaking, Together2Night is one of the premiere crossdresser dating sites you can join. Signup is quick, easy, and free, and you can make exciting new connections in a matter of minutes.
logo IWantBlacks


Specially designed for the black community, IWantBlacks is a sleek, chic dating site where like-minded singles can match, message, and meet. The site has a thriving cross-dressing community too, which is perfect for any ebony-curious dater to explore.
logo GaysTryst


Another great LGBT dating service, GaysTryst, aims to match you with hot singles in your area – all for free! With a user-friendly design, it’s great for both gay and bisexual singles, as well as curious men interested in dating crossdressers.

What is Crossdresser Dating?

Crossdresser dating is when you start a romantic or sexual relationship with a man who enjoys wearing women’s clothing. Crossdressing is often confused and mislabelled in mainstream media, and many people have unfair opinions of how cross-dressing relationships operate. But quite often, crossdresser dating follows the same format and milestones of traditional dating. So why do men enjoy cross-dressing? Some men choose to wear women’s clothing to heighten sexual fantasies, including roleplaying and BDSM, and enjoy the ‘taboo’ nature of it all, where wearing something they shouldn’t help get them off.

Others may simply enjoy the idea and feel of women’s clothing. It’s important to remember that cross-dressing is not directly linked to sexuality – meaning that men who cross-dress can be straight, as well as gay, bisexual, or transgender. Many heterosexual couples enjoy cross-dressing because of how fun, easy and imaginative it can be to their sex lives.

Are Crossdresser Dating Sites Safe?

Crossdresser Dating Sites

In many countries and society in general, cross-dressing is frowned upon and often regarded as an embarrassing kink – which we all know to be false! But for this reason, joining popular mainstream dating sites can be difficult for crossdressers and those who want to date them. Specialized crossdresser dating sites are key to safeguarding you and making finding a suitable date easy. While dating sites make every effort to protect their users, as with any minority dating, it’s important to keep yourself protected and safe.

As always, ensure you read each site’s privacy policy and familiarize yourself with their protection features, including how to block/report a profile and protect your private information. On the plus side, there are very few time-wasters who join cross-dressing sites. Profiles are genuine, detailed, and active, with many of the sites recommended having very supportive, trustworthy communities of cross-dressing daters.

How Does Registration Work for Crossdresser Sites?

Registration for crossdresser dating sites is quite often very straightforward. Firstly, many sites are open to both men and women of any sexuality and cater to couples and group fun. Many trans people also join these sites too. Signing up should take only a few minutes, where you’ll only need to provide a valid email address to begin, along with some basic profile information such as your age, location, and gender.

During signup, it’s strongly advised to upload clear profile pictures to rank higher in member searches. Pictures can even include cross-dressing to attract maximum interest and the right kind of attention. Some sites offer identity verification on signup, which is a great way to prove you are genuine and authentic. Almost all sites either have an app or are mobile-optimized, allowing you to create your account conveniently and securely.

Our Advice When Using Crossdresser Dating Sites

Crossdresser Dating Sites Benefits

While crossdresser dating sites are similar in many ways to traditional dating, there are some caveats to be aware of. Consider the following:

  • Be respectful in your messages – some people may only be new to cross-dressing and are still familiarizing themselves with it/trying new things.
  • Know what you want – are you interested in a long-term relationship? Casual sex? Or friendship?
  • Always tailor your messages to individual profiles, and never assume anything. Spend time reading a crossdresser’s interests and likes.
  • Trust your instincts – if you’re feeling uneasy or suspicious talking to somebody, consider using the site’s many safety features. Your comfort and protection should always be a priority.
  • Some cross-dressing is directly linked to roleplaying – if you have a specific fantasy, consider investing in costuming/props to heighten the experiences.
  • If you enjoy a particular site, consider upgrading your account to enjoy a premium chat and search features, including more matchmaking visibility.

The Benefits to Using Crossdresser Dating Sites

There are several benefits to using crossdresser sites. Mainstream apps and dating sites make it impossible to find fellow crossdressers, and many people are not comfortable admitting they enjoy cross-dressing on public platforms. Crossdresser sites are tailor-made to match you with like-minded people in a safe, secure environment. Many users state their intentions clearly on profiles, allowing you to find someone who shares your interests and goals.

Particularly if you are new to cross-dressing and are looking for new friends, mentors, and ideas, these dating sites allow you to join communities and communicate openly. And because these sites use your location in matchmaking, you’ll be able to make local matches and meet in person very easily. Perhaps one of the biggest benefits is that many crossdresser dating sites are free to join, meaning you can engage with the community and make new friends without it ever costing you a thing.

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