Crossdresser Dating Sites

Online Dating

11 Best Free Crossdresser Dating Sites (Feb. 2024)

Amber Brooks

Written by: Amber Brooks

Amber Brooks

Amber Brooks is the Editor-in-Chief at When she was growing up, her family teased her for being "boy crazy," but she preferred to think of herself as a budding dating and relationship expert. As an English major at the University of Florida, Amber honed her communication skills to write clearly, knowledgeably, and passionately about a variety of subjects. Now with over 1,800 lifestyle articles to her name, Amber brings her tireless wit and relatable experiences to

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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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 and apps are still a relatively new phenomenon.

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

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

AdultFriendFinder has over 100 million members, 4.7 million connections, 20+ years of experience — these are the kind of impressive numbers for a crossdresser hookup community. Singles and couples of every sexual preference can be themselves and express their desires freely — from crossdressing and swinging with local femboys to threesomes with friends with benefits. Browse member profiles by appearance, interest, and gender, and when someone catches your eye, take things to the next level by going into a private chat.


Ashley Madison is a discreet dating site and app that takes user privacy very seriously. Because most of its 80 million members are seeking extramarital affairs or side relationships, the dating network has a lot of systems in place for assuming a sexy persona that has nothing to do with who the person is every day in real life. A crossdresser can use Ashley Madison as a safe dating ground for exploration and making new acquaintances. There is no judgment here, so you’re free to chase your desires and fetishes on your terms.


Embrace your passion for the crossdresser lifestyle on — a hookup site where it’s free to create a dating profile, search for potential matches, and chat up anyone you fancy. has a diverse dating network that reaches 40 countries, with the biggest chunk being in the U.S., the U.K., and Canada. Over the last few decades, more than 70 million singles have given a try, and it has led to many a romantic date and sexual encounter.


You may be surprised to see it on this list, but Match is for daters of all ages, ethnicities, religions, sexual orientations, backgrounds, and lifestyles, including crossdressers. Once you share some information about yourself on your dating profile, specify what you’re looking for in a casual hookup, date, or partner. This is the criteria Match will use to connect you with new people, and Top Picks with high match ratings can chat with you for free. You never know who you’ll meet on Match, but you can rest assured that fake profiles and harassment will not be a hazard on this relationship-focused internet site and app.


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 post X-rated content and state their kinks and fetishes upfront. 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 members.

Crossdresser Dating Site wants to help you “date a sexy crossdresser tonight,” and the dating platform does that by offering free signup, browsing, and flirting. Upgrade and you can send private messages and check out the online dating site’s webcams and chat room. Crossdresser Dating Site is part of the Infinite Connections dating network, which means if you create a personals ad on one site, and it will appear on all of its sister sites — at no additional cost. Whether you’re a man, woman, cross dresser, or couple, you’ll receive a warm welcome in the Infinite Connections Network and can start searching for crossdresser dating opportunities.


The self-proclaimed “#1 crossdresser dating community on the net,” Date a Crossdresser has thousands of members filtered by things like location, age, username, and who’s online. This dating 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 find a local crossdresser, input your email, username, password, birthday, gender, headline, city, description, and the type of people you’re interested in. The matchmaking algorithm with drum up some search results specific to your sexual preference, and you can reach out to a potential dating partner.


If you’re a crossdresser who’s got sex on your mind, Crossdresser Hookup has your back. You can find no-strings-attached relationships thanks to the hookup site’s vast user base, easy-to-use process, and free subscription. Crossdresser Hookup belongs to the Infinite Connections family, so you’re getting access to a vast network of people of every sexual preference. Unlike on vanilla dating sites, everyone on Crossdresser Hookup is into the same kinky lifestyle, and they’re looking for a kinky partner to take to bed. Our experts rank this site among the best hookup sites for meeting a fellow crossdresser who is down for casual sex.


“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 and active sites in this dating niche. No matter if you’re a vet or a newbie, the online dating site provides all the resources you need to find a potential date or a potential partner. Its free dating resources include online registration, dating profile creation and modification, local search functions, and certain types of communication. You can take the Meet a Crossdresser platform for a spin and browse members without paying for a membership plan, but private chatting will cost a little extra.


Senior crossdress singles looking for friends, dates, or relationships can find lovely singles on The dating website 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, and a safety guide with tons of expert advice for navigating the crossdress lifestyle and avoiding sketchy people and fake profiles. If you have experience on your side and want to engage with a fellow crossdresser over the age of 50, may be your best chance.


Club Crossdressing boasts that it only takes 30 seconds to join and start meeting some lovely singles. Give the dating website 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 to get a free membership in this crossdressing club. Club Crossdressing welcomes singles from all walks of life — from local femboys to transvestite dating. The dating profile includes every sexual orientation and gender identity, so you don’t have to hold anything back to meet a person who fits your lifestyle.


FAQs: Where Can I Find Crossdresser Personals?

The popular dating sites on this list have tons of profiles and personal ads for your perusal, but if you’re looking for an anonymous browsing experience — meaning you don’t have to sign up to look at crossdresser personals — then Adult Friend Finder could fit the bill.

This adult dating site features many personals organized by category (casual sex, swingers, threesomes, transsexual sex, etc.), and free members can explore the database of sexy singles without having to sign up and hand over their personal information or credit card numbers.


Relationships: Hookups Only

Match System: Search by location, interest, more

Our Experts Say: “Make no mistake: this site isn't about making friends, it's about finding hookups and casual encounters. No adult site has a larger or more active user base of those seeking discreet fun...”

Browse Free: View Photos Now

Adult Friend Finder is a natural ally to transgender, transsexual, and transvestite singles, and also anyone who’s curious about that kinky lifestyle. This zero-judgment and LGBTQ-friendly website promises to titillate and excite with its sexy photos, videos, blogs, and chat rooms.

You must be a member to send messages to AFF users, but you don’t have to sign up to take a look around this local hookup site and see if any personal ads strike your fancy.

Are There Any Crossdresser Dating Apps?

There are a lot of different apps that cater to the LGBTQ+ community and have filters that are helpful to crossdresser singles. Taimi is one of the more well-known and reputable trans-friendly dating apps, and it promises not to discriminate against people because of their sexuality or gender identity. This inclusive space is a welcome safe haven for those who tend to think outside the typical heteronormative box.

As far as protecting privacy, one of the best dating apps for staying anonymous in the dating scene is Ashley Madison. This affair dating app provides photo blurring and masking features to ensure users can keep their real life separate from their online dating life.


Relationships: Hookups, Casual Dates, Affairs

Match System: Search by age, location, appearance, and more

Our Experts Say: “With its massive user base and advanced privacy features, Ashley Madison is the #1 site for discreet hookups, dates, or relationships...” Full Review »

Browse Free: View Photos Now

Feeld is a good dating app if you’re sexually adventurous and up for polyamorous relationships and kinky sexual encounters. This open-minded network can give users the freedom to express themselves and find sexy singles, couples, and groups who have few inhibitions and wild imaginations.

What’s the Safest Adult Dating Site?

Safety is an important concern for crossdresser singles because they encounter more hate speech, harassment, homophobia, and abuse than almost any other group in the dating scene. Cyberbullies can feel empowered by the anonymity and lack of consequences online and mock, threaten, stalk, or otherwise victimize crossdressers just for being who they are — and that’s not right and it’s not something a legitimate dating site or app should ever tolerate.

If you’re a crossdresser and want a safe space to find a casual date or local hookup, then our online dating experts would recommend checking out Not only does Flirt offer unlimited free chatting, but it also has ironclad security features and verification tools to keep users from misbehaving as they flirt and pick up local dates.


Relationships: Hookups, Casual Dating, Chats

Match System: Search by age, location, gender, orientation, and other factors

Our Experts Say: “ frees singles to chat with attractive locals and pick up dates on the spot. This hookup site is always open to horny and sexy people seeking one-night stands, casual dating, threesomes, and other sexual encounters...”

Browse Free: View Photos Now swiftly removes fake profiles, cyberbullies, and anyone behaving inappropriately online. If a bad egg somehow manages to slip past the website’s defenses and bother you, all you have to do is click the Block or Report button, and they’re gone from your sight for good.

Flirt users must provide a reason as to why they have blocked a person, and they can choose to report the behavior if they think the transgression is serious enough to warrant the dating profile being deleted and the account suspended. Flirt gives singles the power to fight back against online bullies and remove any toxic people from their feed, and that’s what makes it one of the safest places to meet sexy singles online.

Which Dating Site is the Most Kink-Friendly?

Everyone has their kink, and a person who identifies as a crossdresser or transvestite is usually pretty open about what theirs is. Crossdressing men who like to wear women’s clothing can get a lot of attention for the salacious pics and flirty attitudes. Certain online dating spaces welcome these unique individuals and celebrate their kinky qualities.

Local crossdressers can swipe, match, and chat without judgment on BeNaughty. This crossdresser hookup site is open to singles of every sexual orientation and gender identity.


Relationships: Hookups, Chats

Match System: Search by encounter, location, and more

Our Experts Say: “BeNaughty is a premier hookup app where you can feel comfortable expressing your desires. Plus, it's free to join, browse, and flirt...” Full Review »

Browse Free: View Photos Now

When it comes to crossdresser dating sites, BeNaughty ranks near the top of our list because it’s safe, free, fun, and totally kinky. This chat room is positively teeming with local crossdressers, and it only takes a simple search and mass text to get in touch with them.

Singles can choose to view personal ads one at a time in the Like Gallery, or they can set matchmaking filters by age, location, gender, appearance, and other attributes to find the perfect match on this adult dating website.

Is There a Dating Site for a Crossdresser Admirer?

Yes, the Crossdresser Dating Site exists to help users find crossdressing men and women in their area, and its search tools make it pretty easy to navigate. You’ll start by identifying yourself as a man, woman, or couple seeking a crossdresser, and then you can browse the cross dressing dating database by interest, location, or kink.

If you want to date crossdressers, you should check out Crossdresser Dating Site and other related crossdresser dating sites featured on this list.

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 isn’t any shame in shaking up your wardrobe, bucking heteronormative trends, and letting your freak flag fly.

As you can see from these crossdresser dating sites, lots of people are looking for dates who don’t fall into stereotypes and like to have fun in drag or playing butch, sissy, or ladyboy now and then.

For single crossdressers, there’s hardly a better way to connect with each other than dating websites and apps, and we’ve just listed the best of the best!

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