If he asks you out at the end of a day or a night, maybe you are their last option after they failed to ask other girl to go out with him, or he just wants to have sex with you. This is very simple. If he really likes you, he would want to spend more times with you. Why would he ask you out at the end of a day? Face it, you are just his last choice when there is not any.
If he never invites you to his place or never introduce you to his friends and family, then he may be just playing with you. He may never want a serious relationship with you. Even worse, you may be the third person in his other relationship. If not, what are they hiding? Are they embarrassed for being with you? Are they afraid to be misunderstood as a gay for dating a transgender woman? Taking you out and introduce you to him friends should be something spontaneously want to do if they really like you and dare about you.
They have no friends. If they have no friends, it says a lot about their personalities and qualities. Normally, a healthy relationship would include time with you and time with him friends. You should have separate space and time for yourselves. If he doesn’t have any friend, you should know that he may not be a good partner also.
If they have aggressive behavior, you should be very careful. There are lots of examples about transgender violence. Plenty of haters outside are looking for opportunities to give vent to their twisted mind. Hundreds and millions of transgender people are killed every year. The number is quite terrifying. You should know that safety always comes first.
If he send you erotic pictures and ask you on a tranny date, it is obviously a one night-stand. He is just looking for a hookup, but never a serious relationship. As a transgender person, you should be more careful about it.
If they are rude and judgmental of others, it will come on you one day eventually. Transgender people are the most judged group of people in the world. The last thing they want is being judged by their partner. You have to understand that they will to you if they are to others. It is just the matter of time.
The last red flag is that if he does not have a good relationship with his family, maybe he will have some issues with you as well. Family relationship and romantic relationship have something in common. Communication is the key in a relationship. If he can’t do a good job with communicating with his family, maybe the problem will remain with you.