I have found three types of people who are attracted to trannies: Those that are too shy, those that are too bold, and those that are just right. So if I can play Goldilocks here, let me give a few suggestions about what works well with me (and probably many of my friends).
The key thing about trannies is to remember that we have both male and female attitudes towards dating and romance. Generally it means that, like men, we enjoy our sexuality, and like women, we enjoy the romantic process of courting. The best suitors keep both concepts in mind.
I always like to begin with an intelligent conversation. Fortunately a conversation is easy to start with a tranny, as they always like to talk about themselves. Compliment her on her outfit and presentation, ask her about her transgender life, ask her about other places trannies congregate. Find out about her hobby interests, favorite films, books, and music. Weave in facts about yourself as you go, but let her have the floor. If the conversation is really working, suggest repairing to a quiet part of the venue to make it easier.
Trannie girls are often very intelligent and appreciate forthright honesty. They have an extraordinary sense of humor and are full of surprises. Trannies (and admirers) tend to be more sensitive and sometimes misunderstand the tone of a comment and overreact. Criticism should be indirect and given sparingly.
If it is me, ask me to dance with you! I just adore dancing, and I don't care if you are not as much of a dancer as I am. Many of the other gals love to dance too.
Another important suggestion is to think beyond the evening. You will want to become part of the social network and that does not happen immediately. Try to talk to all the girls. Work on making a group of friends and the love affairs will happen by magic.
You will also find that some girls take a little longer than one night to feel comfortable with you, and will respond much more warmly to a regular than a newcomer. Some of us have had some bad experiences with people hitting on us blatantly, and you can avoid being rejected by going slower.
There are a few things to avoid. Most everyone already has a clue here, but for the benefit of those who are still learning social skills, here is a short list: Don't ask us if we are "real". Don't immediately ask if we are pre-op or post-op; don't lie. Don't apologize for being who you are. (It is ok to let us know you are attracted to us and inexperienced or nervous). Don't ask us for sex right away and don't touch until we know each other well enough. Avoid pressing your case if you are more intoxicated then they are.
So what do you do when you find a tranny you really like?
It is simple, ask her out! Most of us absolutely adore going out with a gentleman to dinner or a show. Follow the same pacing as is recommended for going out with a genetic girl and you will do well. Usually that means 3-5 times out before intimacy, the first time in a public place like a coffee shop, the second time to dinner, and to activities of common interest thereafter. If after 5 times out, nothing happens, it is not likely anything ever will.
Most tranny girls love it if you overdo the gentleman thing. Open the door for us; bring us flowers. Make us feel like ladies and you will win our hearts.
Some admirers are too shy. Perhaps they feel ashamed of being attracted to trannies. They should not be - I feel that trannies are among the most interesting and kind people around. (When I was dating as a man, I was very shy around women and often waited for them to ask me out.) Confidence does not come quickly and one should not take a "no" as a defeat. Rather your interactions are a learning situation and you should always reflect on what you did and how it came off.
When the time comes for intimacy, here is how I like to proceed:
First, try and start with a new lover relatively early in the evening. You won't be tired and if someone comes too quickly you can rest for a bit and try again.
Follow the classic baseball sequence: Hold hands, kiss gently at first, when the passion grows hot, feel me up my dress slowly, and when neither of you can stand to wait any longer, make love. The longer we hold off an orgasm, the better it is. In my case, I don't always have orgasms and I enjoy sex with or without.
Realize that the first time, while it can be very passionate, will be a little awkward too. Always start gentle and work your way up the intensity scale. We need to talk as we go, so we can learn stimulation levels and the signals we will use. If things go wrong in some way, try and be calm and work things out. If you are not as experienced as I am, don't worry, I am glad to help you learn.
Generally our first experiences will involve oral sex and mutual masturbation. Anal sex requires more skill, trust, and preparation to do well, so it is best to put that off for a little while. Some of us find it hard to come from oral sex and some are uncomfortable with anal sex. Always use lubricants for hand jobs and vary the speed and intensity of stimulation.
After you become comfortable with basic love-making, then we can try experiments! Love is very much about learning and is fortunately a vast subject.