10 Best Free “Crossdresser” Dating Sites (2020)

Online Dating

10 Best Free “Crossdresser” Dating Sites (2020)

Amber Brooks
Amber Brooks Updated:

Crossdressing has been around for centuries — seen in Greek, Norse, and Hindu mythology (Achilles), history (Charles D’Eon), TV shows (RuPaul), and movies (Dr. Frank N. Furter). But crossdresser dating sites are still relatively new.

Online dating has empowered singles to find people who share similar interests, fetishes, and lifestyles, and that’s been empowering for the crossdressing community.

Crossdressing singles may feel uncomfortable or judged on mainstream dating sites, but they are welcomes with open arms in certain niche communities. We’ve scoured the web to bring you the top 10 crossdresser dating websites. On these platforms, you don’t have to hide who you are or how you like to dress.




AdultFriendFinder has 77.4 million members, 4.7 million connections, 20+ years of experience — these are the kind of impressive numbers you’re looking at when you’re part of the  community. In addition, you can be yourself and express your desires freely — from crossdressing and swinging, to threesomes and friends with benefits. Browse profiles by appearance, interest, and gender, among other things, and when someone catches your eye, take things to the next level by going into a private chat.




FriendFinder-X has one of the most welcoming dating forums of any site, not just hookup sites. It doesn’t matter what your lifestyle is — the millions of folks on FriendFinder-X won’t judge you. In fact, the sex site even allows members to offer advice to each other. Sign up for a basic account, and you won’t have to provide any payment information — you’ll just head straight to profile creation and browsing.




Match.com is for daters of all ages, ethnicities, religions, sexual orientations, backgrounds, and lifestyles, including crossdressers. Once you share some information about yourself on your profile, specify what you’re looking for in a hookup, date, or partner. This is the criteria Match will use to connect you with that special someone. You won’t have to spend any money to do so. You also won’t have to spend any money to search and send and receive likes and virtual winks.

Crossdresser Dating Site wants to help you “date a sexy crossdresser tonight,” and the platform does that by offering free signup, browsing, and flirting. Upgrade and you can send private messages and check out the site’s webcams and chat rooms. Crossdresser Dating Site is part of the Infinite Connections dating network, which means create a profile on one site, and it will appear on all of its sister sites — at no additional cost. Whether you’re a man, woman, crossdresser, or couple looking for men, women, crossdressers, or couples, you’ll feel welcome here.

URL: https://www.crossdresserdatingsite.com/




Embrace your passion for the crossdresser lifestyle on xDressr — where it’s free to join (either via the homepage or Facebook), find matches (either click Like or Pass), and send messages. If you want to receive messages, you’ll have to register for a paid membership. In addition to the desktop version, xDresser, which was founded around 2016, also comes in app form for all iOS and Android phones and tablets. So you can date no matter where you are.

URL: https://www.xdressr.com/

The self-proclaimed “#1 crossdresser dating community on the net,” Date a Crossdresser has thousands of members whom you can filter by things like location, age, username, and who’s online. This website is 100% free and has features that allow you to create a profile, upload photos, send virtual flirts, add favorites to your Little Black Book, and receive instant messages. To get started, input your email, username, password, birthday, gender, headline, city, description, and the type of people you’re interested in.

URL: http://www.dateacrossdresser.com/

If you’re a crossdresser who’s got hookups on your mind and your mind on hookups, Crossdresser Hookup has your back. You’ll find no-strings-attached relationships in no time — thanks to the site’s vast user base, easy-to-use process, and free subscription. Like Crossdresser Dating Site, Crossdresser Hookup belongs to the Infinite Connections family, so you’re getting a two for one (or more like a two for a dozen) here.

URL: https://www.crossdresserhookup.com/

“A discrete dating club where crossdressers and admirers come to play,” Meet A Crossdresser came onto the scene in 2011 and has made a name for itself as one of the most fun sites in this niche. No matter if you’re a vet or a noob, the site provides all the resources you need to find that special someone. These resources include free registration, profile creation and modification, as well as search and certain types of communication.

URL: https://www.meetacrossdresser.com/

Seniors looking for friends, dates, or relationships can meet those goals and more on SeniorCrossdress.com. The site offers all the necessary tools for signing up, uploading your info and photos, browsing, and getting to know matches — plus things like TV/TS personals (transvestite and transsexual, respectively), a transgender chat room with thousands of users, and a safety guide with tons of expert advice for navigating this lifestyle and avoiding sketchy people.

URL: https://seniorcrossdress.com/

Club Crossdressing boasts that it only takes 30 seconds to join, and that seems to be the case. Give the site your email, password, username, gender, age, location, appearance, lifestyle habits, interests, characteristics and those of your ideal match, and a reason for joining (e.g., romance or crossdresser pen pals). Even more good news is you won’t need your credit card for this.

URL: https://www.clubcrossdressing.com/

Wear What You Want & Love Who You Want!

Whether it’s a French diplomat trying to reestablish relations between two countries or a single man expressing his desires — crossdressing isn’t new to this world, and there are many reasons why people do it. For single crossdressers, there’s hardly a better way to connect with each other than dating websites, and we’ve just given you the best of the best!

Photo source: woodtheater.org