Sissy And Femboy Dating Sites

Gay Dating

6 Best Sissy & Femboy Dating Sites (May 2024)

Amber Brooks

Written by: Amber Brooks

Amber Brooks

Amber Brooks is the Editor-in-Chief at DatingAdvice.com. 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 DatingAdvice.com. She has been quoted by the Washington Times, Cosmopolitan, The New York Post, and AskMen.

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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.

Reviewed by: Jon McCallister

Jon McCallister

Jon came to DatingAdvice in 2016 with more than 15 years of editorial experience behind him. He has experience editing, writing, and designing at numerous publications, including the Gainesville Sun. Jon enjoys researching emerging trends and seeking out the companies, organizations, and individuals making an impact in the modern world of dating. He excels at working closely with writers and editors to improve the quality of online content.

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Advertiser Disclosure

Although terms like “sissy dating sites” and “femboy dating sites” are popular Google searches, a lot of gender non-conforming and transgender people find them derogatory.

Looking for love in the trans community can get complicated, especially when it comes to safety, so finding the safest dating sites and apps makes a huge difference — both for trans singles and for the cisgender people seeking them out.

Kink-friendly sites and apps make it easy for people with femme presentations to connect with appreciative potential partners while avoiding harassment and stalking which is still, unfortunately, a problem on many mainstream dating platforms. Step out of the inflammatory porn-based terms and find what you’re looking for!

Fluid | Anonymous | Transgender | FAQs

Best Overall Site for Fluid Dating

Whether you identify as trans, nonbinary, or fluid, you probably would prefer a dating platform that kept its options, and its gender labels, open for you. The following casual dating sites provide more options for gender identity and sexual orientation than the mainstream apps, and all kinky people are welcome to explore!

★★★★
AFF.com 4.2/5.0

Our expert ratings are based on factors such as popularity, usability, value, and success rate of each site.

4.2/5.0

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 provides a safe and judgment-free space for kinksters, swingers, polyamorous people, and the queer community at large, so it should come as no surprise that the hookup site provides a warm welcome to trans people and their admirers.

From the signup process onward, Adult Friend Finder offers an open, welcoming atmosphere to explore the sexier side of life, allowing people to sign up as singles and couples alike. The site also lets you put your kinky foot forward, encouraging openness about fetishes and kinks right on your profile.

Although Adult Friend Finder doesn’t censor adult content on the platform, from videos to forum posts and erotic content in chat rooms, it creates a safe space by moderating harassment. You can stick with the public areas of the site for free, but if you want to talk one on one or video chat individually, you’ll need a premium membership.

2. Butterfly

A lot of dating platforms that cater to the trans community struggle with the line between making an inclusive space and avoiding harassment, but Butterfly strikes the balance by starting from respect and dignity. Rather than using terms like “sissy,” which cater to fetishists, Butterfly focuses on helping trans daters find compatible dates instead of “chasers.”

The app launched in 2020, and membership is fairly evenly split: 34% of members are transgender, 43% are cisgender male, and the remaining 23% of Butterfly members are cisgender female. From registration onward, identities and sexual orientation are a core tenet of respect.

Screenshot of Butterfly
Butterfly provides a safe and inclusive space for queer dating.

Butterfly lets users self-identify using any of 21 gender identity tags and 10 different sexuality tags, so inclusion is baked in. If you want to keep your gender and sexuality private, you can choose that option as well.

The team behind Butterfly also understands that privacy, safety, and security are major issues for the trans community and allies who have a romantic interest in trans people. That’s why the app includes specific features and tools to keep users secure and safe. Personal information is at a minimum, and the app uses approximate locations rather than specific geolocation data. All in all, Butterfly helps members of the trans community and trans-attracted cisgender daters connect and communicate safely, without harassment.

Best Dating Apps for Anonymous Meetups

Privacy is the number one concern among some closeted individuals in the online dating scene. These two dating apps put anonymous meetups first and allow daters to mix and mingle without outing themselves.

★★★★
AshleyMadison.com 4/5.0

Our expert ratings are based on factors such as popularity, usability, value, and success rate of each site.

4.0/5.0

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 »

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Given that Ashley Madison is all about discreet dating, it should come as no surprise that the affair dating platform also provides an outlet for closeted trans women and gender non-conforming men. Ashley Madison’s anonymity features include photo blurring, the option to use false names, browser history clearing, and the panic button, among others.

With features like these, it’s easy to see why trans women who aren’t yet ready to be out, men who prefer a more femme presentation, and cisgender men seeking a discreet platform to explore their interest in trans women see Ashley Madison as a valuable resource. 

Women on Ashley Madison have access to all of the features of the site and app for free, but men must pay for credits to gain access to tools like messaging, video chat, and sending virtual gifts. Fortunately, the discretion extends to payment options as well, so even in paying for the service, you can keep your desires as private as you want.

4. Pure

If staying anonymous while satisfying your needs is your goal, the Pure app has all the tools to help. The dating app works a bit differently from mainstream platforms, and operates more like old school classified ads, with a digital touch. You don’t have to provide any personal information to get started, keeping you anonymous on the platform.

Pure dating app
Pure is a hookup app that connects kinksters on the DL.

Once you’re set up, all you have to do is post an ad to get started. Pure encourages users to be honest and open, and to get as explicit as they want in their ads, so feel free to really put yourself out there. Your ad stays up for 24 hours and is open to users in your area. After 24 hours, your ad and all the messages attached to it disappear.

Although Pure encourages users to let their imaginations run wild, every member must adhere to the code of conduct, so vulnerable members don’t have to fear harassment or degrading comments. 

Best Dating Apps for Trans Safety

Unfortunately, harassment and bullying is very much a reality for LGBTQ+ singles looking for dates online. The typical safety standards may not be protection enough for certain vulnerable populations, and that’s why we recommend trustworthy dating sites that have proven to be safe over the decades.

5. Match

★★★★★
Match.com 4.9/5.0

Our expert ratings are based on factors such as popularity, usability, value, and success rate of each site.

4.9/5.0

Relationships: Friends, Dates, and Relationships

Match System: Browse by zip, age, appearance, more

Our Experts Say: “Match has a massive and extremely active gay user base, as over 1 million gay, bisexual, and curious men use the site to find dates and partners…” Full Review »

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Although Match is a mainstream dating site, the platform puts the safety and security of its members as a high priority, making it a good option for trans daters and singles seeking out trans women to date. The dating site and app both use active content moderators to make sure that harassment doesn’t persist, and eject any trolls that may come up on the platform.

Match is a little hit or miss when it comes to LGBTQ+ dating because while the platform does allow for trans daters to appropriately self-identify, it continues to struggle with providing adequate features for bisexual and pansexual members. 

Match does, however, take a zero tolerance approach to harassment on the platform, and user safety is a major concern for the development team. Users also have tools to help steer them to the right profiles on the platform, including filters for age, body type, gender, and other factors. Premium subscribers get access to even more filters, tools, and perks, including unlimited communication.

★★★★★
eharmony 4.8/5.0

Our expert ratings are based on factors such as popularity, usability, value, and success rate of each site.

4.8/5.0

Relationships: Casual Dates, Deep Relationships

Match System: Personality test suggests matches

Our Experts Say: “eharmony has opened its registration to same-sex couples, including gay men, so everyone can benefit from its psychology matching system…” Full Review »

Browse Free: View Photos Now

Although eharmony may be far from the first platform that comes to mind for transgender dating, the dating site and app accommodated trans women (and the singles that seek them) even before it accommodated Gay and Lesbian daters. The dating site also offers a safe atmosphere thanks to strong content moderation policies and strict enforcement.

For trans women looking for long-term love, eharmony can be a surprising ally because the site matches users based on compatibility as well as the features that each member states they’re looking for.

The eharmony platform updated in 2024 to correct its longstanding issues when it comes to gender and sexual orientation. The team has taken the right steps to include fluid dating identities so you can find true love whether you’re heterosexual, homosexual, bisexual, or pansexual.

FAQs: Is Grindr Safe for Trans Women?

Although Grindr is technically for man-loving men, a lot of trans women use the platform to seek out adventurous men who are interested in hooking up. Things can get a bit complicated in terms of identification, however, since Grindr continues to work out its approach to nonbinary and transgender inclusion. 

Although Grindr’s goal is inclusion and respect, trans women do occasionally experience harassment on the platform. This has been a particular issue in light of more recent attacks on trans rights across the U.S., including many gay and bisexual men taking an anti-trans stance. But Grindr remains a safe and fairly proven platform for trans women as well as trans men.

What is a Good Inclusive Social App for Trans People?

If you’re looking more for social connection and community than a hookup or relationship, there are a few trans-friendly apps that provide the right atmosphere.

The Taimi logo
The Taimi app is a dating and social network for LGBTQ+ singles.

Taimi is a dating app geared toward the LGBTQ+ community, but the approach is much more social than mainstream dating platforms. Taimi fosters inclusion across sexual orientation and gender identity, and users interact via groups and their newsfeeds, rather than curated matches or specific searches. 

Plura, formerly known as Bloom Community, is another inclusive space, helping members of the LGBTQ+ community connect both online and offline. Plura extends that inclusiveness to kink and polyamory communities as well as to gender and sex minorities, and encourages members to organize and attend in-person events as well as chatting online.

Is Online Dating Safe for Trans Women?

It’s no secret that dating for trans women is dangerous, and online dating can be precarious for trans women on a level that just isn’t the case for cisgender women. But niche dating sites also make it possible for trans women to connect with each other as well as with admirers, without running the risk of harassment or other problems.

Trans women should take the same precautions that we recommend for online daters in general, with a special attention to safety when it comes to first-time meetings with someone you connect with online. 

Trans Dating Online is Much More Than Just a Femboy Kink

Gone are the days when trans women and gender non-conforming men had no options beyond platforms labeled “sissy dating sites” to find the right partners for casual sex or long-term love. A growing number of niche dating sites cater to the transgender community and allies seeking relationships with trans and nonbinary partners, so there are plenty of options at your disposal.

Find the right match and stay safe while satisfying your needs!

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