There are at least some dominant girls who are into relationships that involve feminizing a male partner. There are many more professional dommes who will do paid feminization sessions. So if what you're looking for is a sexual experience that involves being feminized, which will be what you are looking for.
If you don't care so much about the experience of being feminized by a girl especially, some crossdressers enjoy getting together with others for sex or just for dressing up, so may work for you.
If you'd rather start learning on your own before meeting others, the web is your friend. If you want to learn about makeup, there are a million tutorials on YouTube. If you want to learn about women's clothing, there is a general recommendation out there for ladies or specific recommendations for trans women who are trying to figure out how to fit clothing to a body that went through testosterone-driven puberty. But these are for how to look like a normal person going to school or a job or something, and they probably aren't what you're looking for. Most clothing women actually wear isn't going to be very exciting, and when most women wear makeup at all, it's just a little bit of eyeliner and lipstick or something. Even women who are interested in more elaborate looks may not be going for the same kind of look you are trying to achieve. I recommend that you look for sites and tutorials and videos specifically for and by crossdressers and sissies as a way of getting started.
How to crossdress and be a sissy At schools!
Two schools of thought is one sissy training and two finding a woman. Which do you want and in what order?
A woman will help you with all that but will want to know you are into her too. It's like asking a girl who likes you to help you find another woman? She will feel rejected.
Now women are awesome sissy trainers I would have you know simply because their femininity comes natural and they don't have to act.
I have had many situations where women help sissy train me. Some long term live in too.
I think the point of focus should be all around being feminine.
Gay men do not like girls and you may be surprised that they don't like anything feminine either. I learned that the hard way being rejected by gay men looking for no fems.
So a woman is a good choice and I think you are asking the right questions.
The girls I liked best and were the most open were the ones who say they like anal and it's fine for you to like it too. It's good to hear a woman approve and validate your feelings.
Some history is always good about your sexual history. Show you are open. Here is a great place to open up about any experiences you have had before and be honest with them.
If you had sex with older boys in the neighborhood tell her. You may find the help you need from her here if you open up.
Always keep in mind this is a fetish and you have good sense and great taste too. Always show confidence you have about crossdressing that you feel it is positive on you.
Once you found a girl who likes and accepts you then talk about being exclusive with her. Most women like the fact you want to be serious with them and see her as an investment.
Steer away from implying you only want sex. This will attract the wrong type. Friendship is the healthy goal to build a relationship on.
Once you and her are an item she will feel more comfortably exploring fetishes with you. Hope this helps.
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