Updated on November 14, 2022

10 Best Crossdressing Dating Sites For 2022

Cross-dressing was once considered an extreme deviation from traditional gender norms, but nowadays this practice is more socially acceptable than ever.

Many men and women all around the world find personal gratification – both erotic and platonic – in dressing and presenting as the opposite sex.

If you’re one of them, you should know there are plenty of crossdressing dating sites out there to help you find a partner who supports this lifestyle!

Check out our suggestions below.

Top 10 Cross Dressing Websites


best-cross-dresser-dating-sites-adult-friend-finder

Adult Friend Finder has long been considered the mainstay among men and women discreetly looking for love – and more! – online.


With over 20 years in the business and a community totaling over a whopping 77 million users, it’s easy to see why Adult Friend Finder is the #1 place for men and women to seek adult fun on the web.

BEST FEATURES

  • Adult Friend Finder isn’t explicitly a fetish site, but it does welcome all kinds of fetishes and kinks. Swinging, BDSM, and group sex are all popular, as is cross-dressing and other forms of gender-subversive play.
  • Both women and men seeking men will have their pick of partners on this site as its users skew strongly male.
  • With over 25.5 million monthly visits, Adult Friend Finder’s popularity alone is testament to its reputation

At first glance, it’s easy to think FriendFinder-X is a typical hookup site, but in reality it’s much more than that.


This site has carved out a well-earned reputation for being one of the most welcoming dating sites on the web.


Whether you’re seeking casual sex, a long-term play partner, or something deeper, this community will embrace you without judgment!

BEST FEATURES

  • Though the site does come with some paid features, it’s free to browse, so you can explore the community and discover just how many folks share your passion for cross-dressing and other kinks before you commit.
  • Like Adult Friend Finder, FriendFinder-X skews more heavily male, making it ideal for women and men seeking men.
  • Site forums make it possible for members to offer advice to one another about safer sex practices and more. You’ll love what a supportive community this is!

#3: Match


best-cross-dresser-dating-sites-match

Match.com is a more traditional dating site than some of the others on this list, but the sheer size of its community makes it an essential addition.


In addition to being the oldest dating site on the web, Match has a huge user base and sees almost 40 million visits each month.

BEST FEATURES

  • New users can get three days free, so you can explore the site and see all it has to offer before committing to a paid subscription.
  • The site skews slightly more female than male, so men and women seeking women will be at a modest advantage here.
  • Your profiles allows you to specify what sort of relationship you’re looking for – hookup, date, long-term partner, or other – and search functions let you narrow down the range of possibilities to include only those who share your interest in cross-dressing.

best-cross-dresser-dating-sites-crossdresser-dating-site

If you want to “date a sexy crossdresser tonight,” Crossdresser Dating Site is here for you!


This site makes it free to sign up, and upgrades allow you to unlock more in-depth features including private chat and webcam communication.

BEST FEATURES

  • Crossdresser Dating Site is part of the Infinite Connections network, which operates a number of niche dating sites. Membership grants you access to this network of other sites, enlarging your pool of possible options.
  • The site’s community includes singles who enjoy cross-dressing as well as couples and groups. Whether you’re a man seeking a woman, a couple seeking a new play partner, or something else entirely, you’re bound to find someone eager to join in on the fun!
  • Because this site explicitly targets cross-dressers, you’ll never have to worry that your lifestyle will be questioned or rejected. Everyone on this site either enjoys cross-dressing themselves, or they prefer partners who like to cross-dress!

best-cross-dresser-dating-sites-xDressr

xDressr allows you to join by signing up through its homepage or through your Facebook account, depending on your privacy preferences.


And this site isn’t just cross-dressing-friendly – it was made specifically with cross-dressing men and women in mind!

BEST FEATURES

  • Paid membership allows you to send and receive messages from other users interested in cross-dressing.
  • The site is available for desktop as well as in app form for Apple and android, allowing you to meet fellow singles anytime, anywhere.
  • A “swipe”-style design makes it possible for you to like or pass on suggested singles, streamlining the process of meeting compatible men and women.

best-cross-dresser-dating-sites-date-a-crossdresser

According to its homepage, Date a Crossdresser is “the #1 crossdresser dating community” on the worldwide web.


It has a standard dating site template that allows you to build a profile and use the search bar to browse available men and women with only a few keystrokes. Best of all, it’s totally free!

BEST FEATURES

  • Fun features like virtual flirts let you start a dialogue with anyone you’re interested in without the pressure of needing to craft the perfect icebreaker.
  • You can save your favorite profiles in your digital “Little Black Book”,  making it easy for you to keep track of whom you’ve talked to and whom you like best.
  • Search functions make it possible for you to locate cross-dressing men and women in your immediate zip code, so you can meet locals who share your kinks without sacrificing discretion.

best-cross-dresser-dating-sites-crossdresser-hookup

Crossdresser Hookup is another cross-dressing-oriented site, but this one is specifically for folks looking for more casual encounters.


Finding a relationship isn’t out of the question, of course, but it’s not the endgame here. This site is about finding fast, NSA fun!

BEST FEATURES

  • A huge community of users means you have plenty of play partners to choose from. If you’re unable to meet in person, it’s still possible for you to enjoy some virtual flirtation and more intimate fun with other members.
  • Because the site is part of the Infinite Connections network, membership grants you access to numerous sister sites, all of which help enlarge your pool of prospects.
  • Subscriptions are totally free! You’ll never have to pay to use any of Crossdresser Hookup’s many valuable features.

best-cross-dresser-dating-sites-meet-a-crossdresser

Perhaps you live in an environment where cross-dressing isn’t accepted, or perhaps secrecy is part of the fun for you.


In either case, Meet a Crossdresser offers the sense of discretion you’re looking for. Since 2011, this site has staked a claim as one of the most exciting cross-dressing niche dating sites on the web.

BEST FEATURES

  • Free registration makes it fast, easy, and fun to sign up and start meeting fellow cross-dressing singles, couples, and more!
  • The community is welcoming of people of all ages and levels of experience in the cross-dressing niche. Whether you’re a total beginner looking for some guidance, or a seasoned cross-dresser looking for someone you can take under your wing, you’ll find what you’re looking for.
  • Profile customization and advanced search features make it possible for you to find exactly the kind of partner you’re looking for – including other kinks!

best-cross-dresser-dating-sites-senior-crossdress

Being a certain age doesn’t mean you stop having a sex life, and it doesn’t mean you have to give up your kinks.


If you’re a senior cross-dresser, you can find plenty of partners who share your zest for life at Senior Crossdress.

BEST FEATURES

  • In addition to cross-dressers, this site also serves transsexual men and women looking for love, sex, and more!
  • Chat rooms make it easy for you to connect with other people in a fun, safe, supportive environment.
  • Experts are on-call to offer dating tips and advice on protecting your privacy and personal safety when meeting new people online.

best-cross-dresser-dating-sites-club-crossdressing

“Join in under 30 seconds free!” is splashed across the homepage of Club Crossdressing, and who could turn down an offer like that?


In less than a minute, you can soon be part of a site devoted to social networking and dating between cross-dressers, and all for free!

BEST FEATURES

  • In addition to helping site users find relationships and casual sex, Club Crossdressing also welcomes platonic social networking, because sometimes what you really need is a friend who gets you.
  • The site is entirely free to use, and you’ll never be prompted to subscribe to paid features.
  • Sharing your lifestyle, interests, and ideal match make it possible for other community members with similar goals to find you.

Conclusion


For some, cross-dressing is a 24/7 part of life. For others, it’s a fun but secret way of keeping their bedroom activity fresh and fun.


No matter what purpose cross-dressing fulfills in your life, these sites will make it possible for you to find compatible partners with similar goals. So what are you waiting for?


Many men that like crossdressers are also into transgender dating as well. Either way, we are sure to help you find a suitable partner with our picks for the best crossdresser dating sites.

Frequently Asked Questions

What city has the most crossdressers?

There is no definitive answer to the question of which city has the most crossdressers. However, there are some cities that are known for being more tolerant and accepting of gender-nonconforming people.

San Francisco, for example, has long been a haven for the LGBTQ community, and its vibrant nightlife attracts people from all over the world. Similarly, New York City is home to a large number of performers and artists who often push the boundaries of traditional gender roles.

As a result, these cities are likely to have a higher concentration of crossdressers than other places. Of course, it's important to remember that crossdressers can be found in every corner of the globe. Whether in small towns or major metropolises, there is no one type of place that is more "crossdressing-friendly" than another.

What is a transvestite person?

A transvestite person is someone who dresses in clothes typically associated with the opposite gender. For example, a man who dresses in women's clothing is a transvestite.

Transvestites may dress for a variety of reasons, including to express their personal identity, to relieve stress, or simply for fun. Some transvestites are also transgender, meaning they identify as the opposite gender from the one they were assigned at birth.

However, not all transvestites are transgender, and not all transgender people are transvestites. In many cases, transvestism is simply a form of self-expression, and it does not necessarily indicate a desire to change one's sex.

What is the point of cross-dressing?

For many people, cross-dressing is simply a way to have fun and express themselves. It can be a way to temporarily escape the restrictions of their everyday lives, or to experiment with a different gender role.

For some people, cross-dressing is part of a sexual fetish or kink. And for others, it may be a way to explore their gender identity.

Is there a dating app for cross-dressers?

While there are many online dating sites and dating apps on the market, there are few that cater specifically to cross-dressers. This may be due in part to the fact that cross-dressing is still widely considered taboo. However, there are a handful of apps that provide a safe and welcoming space for cross-dressers to connect with one another.

These apps include CrossDating, CDate, and Transtastic. CrossDating is a fairly new app that is designed specifically for cross-dressers and their admirers. It offers a safe and secure space for users to connect with one another and explore their shared interests.

CDate is another option that caters specifically to cross-dressers and trans people. It has a large user base and offers a variety of features, including private messaging and profile filtering. Transtastic is less focused on dating and more geared towards social networking, but it provides a welcoming environment for cross-dressers of all ages.

Do cross-dressers have gender dysphoria?

Cross-dressing is the act of wearing clothing that is typically associated with the opposite gender. For example, a man might wear a dress or skirt, while a woman might wear pants or a shirt traditionally intended for men.

While the motivations for cross-dressing can vary, some people do it as part of a transgender identity. That is, they identify as a gender other than the one they were assigned at birth, and cross-dressing is one way of expressing that identity.

However, not all cross-dressers have gender dysphoria, which is the distress that comes from feeling like you are trapped in a body that does not match your gender identity. In other words, not all cross-dressers want to transition to the opposite gender; some just enjoy wearing clothing that is typically associated with the other gender. Therefore, while there is overlap between the two groups, not all cross-dressers have gender dysphoria.

Are cross-dressing men gay or straight?

The answer to this question is not as simple as it may appear. While there are certainly gay men who enjoy cross-dressing, there are also straight men who do it for a variety of reasons.

Some men cross-dress because they are comfortable expressing themselves in a more feminine way. Others do it as part of a sexual fetish or fantasy. And still, others find that cross-dressing helps them to connect with their feminine side.

So, while there is no definitive answer to the question, it is clear that cross-dressing is not necessarily an indicator of sexuality. Rather, it is simply a way for some men to express themselves in a way that feels right for them.

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