Does it work? The feedback is mixed, but I found some seemingly honest perspectives from trans people on this question about Okcupid at Quora, and in this Huff Post story on the topic. Do note that OkCupid does offer a paid upgrade, but you can do quite a bit without paying.
If we're going to talk dating sites, we might as well consider transgender dating apps as well
I looked into the biggie: Tinder! This is a tough one for me to assess. If I were trans myself, I would give it a whirl and tell you all the juicy details. Alas, I can only do my best to suss out what honest people have to say about their experience. You can get a taste from online articles like this one on Wussy, and if you want to know more about what these sites are like for trans people, read this tell-all at Flare.
The problem regarding Tinder that keeps coming up in my research, is that Tinder has a penchant for banning trans members! Apparently this happens after a bunch of angry straight dudes report such profiles, and Tinder just throws the trans women off the app. So it seems like another case where a company's actions don't reflect their words.
My final thought on Tinder is to just give it a try if you haven't already, and delete it if you find it's not working for you. That's the beauty of free apps.
Is there really a transgender Tinder?
Speaking of apps, you might get a bit excited when you read about one called Transdr. Although this app claims to be the transgender Tinder, they unfortunately fall into the Too Good To Be True category, and certainly aren't free. Initially I found a bunch of news stories touting how Transdr aims to create a safe space for transgender women to find dates, but I see that they later ran into some trouble for some marketing pages that used no-no words that can be hurtful to trans members, as reported by the NY Post and others.
Beyond the marketing flub, Transdr faces a catch-22 in a way, because they are trying to bring two groups of people on board: transwomen and tranny chasers. While one may initially think these two groups are a perfect match, the disparity between the real-life wants of transwomen, and the often fetishistic and unrealistic expectations of men who specifically seek out TS dates can create a bit of a conundrum. As this relates to Transdr is summed up nicely in this article at GayStarNews.
All this aside, you don't have to take my word for it because the reviews on the app download pages will tell you everything. A ton of 5-star reviews from users that don't have real names or leave any type of meaningful comment, and then a whole bunch of poor reviews from real users who claim the app is often crashing and has a ton of fake profiles and active bots. The legitimate feedback was honestly so bad that I can't link to the app, but you can find it easily enough.
Don't want to waste your time any further? If you really just want to join a community where trans people are welcome and easy to identify, you might want to consider a paid site after all. Because at this point you are probably wondering, “Paid or not, is there even a real transgender dating site in the first place?!”
Now if you're going to pay, there are some sites that have http://www.datingranking.net/soldier-dating/ lots of members, welcome trans people, and are thriving. However, it seems many of the sites may work out better for the guys looking to meet trans women, than for the trans people themselves. It depends on the what kind of relationship is desired. And that's because the best trans sites are still the overtly sexual ones.