What am I?
I am a cross-dresser. I have believed all my life that what "Dear Abby" and other so-called experts about transvestitism have to say—i.e., I'm not gay, I'm not transsexual, this is just a sexual fetish glued on to a man with an otherwise normal life. Well, as I become older, something is changing. I no longer feel aroused by putting on women's clothes. When I dress, I don't want to masturbate. I want to go out and do the normal things that women do, like window shop and have lunch. I used to dress in the company of other TVs, but now I prefer to be alone, since this makes it harder for others to detect my biological sex. More and more, I fantasize about being a woman, having female rather than male genitals, having breasts, being able to wear what I like all the time, going to work as a woman, etc. I went through a rough divorce with a wife who initially said she accepted me, but over time put unreasonable restrictions on my cross-dressing. That was about a year ago. Am I just going through some depression?
I've always been suspicious about the firm distinction that sexologists usually make between transvestites and transsexuals. Transvestites supposedly enjoy cross-dressing only because it's a sexual fetish. They may wear just one item of women's clothing, like a bra or panties, or put together complete outfits. But they do not want to change into women or live full-time as women. That would make them transsexuals. And transsexuals supposedly have no erotic response to dressing in women's clothing (even though genetic women certainly turn themselves on by getting dolled up).
In my clinical practice as a therapist, I've worked with more than one so-called cross-dresser who decided to transition from male to female. This is especially common when people get older than 20 and feel that the clock is ticking, costing them valuable time. This doesn't happen to every cross-dresser, of course—but when it does, the person should be taken seriously and given the same access to medical assistance as anybody else who comes in describing gender dysphoria.
Unless you can find a very enlightened therapist and doctor to work with, however, I suggest that you do not tell them you once identified as a cross-dresser. Don't tell them that you ever used an item of female clothing as a masturbation aide. Leave the sexual part of your life out of this. But do everything you can to meet others, on-line and in person, who can hopefully validate your experience. The next step for you would be to begin hormone treatment. Do you feel ready for that?
I doubt that you are simply going through depression, although many people who want to change their sex are depressed, just because they know how hard that process is going to be. It's certainly important to see someone who can talk to you about the divorce and the other stresses in your life, and see if you need therapy or medication or both. I do recommend that people who transition get a therapist they can trust, not because I think differently-gendered people are crazy, but because so-called normal people have such crazy reactions to us. I think the divorce created a space in your life where you realized that you could think about making this change.
A gender transition takes years to accomplish. So settle down and prepare to be patient. You can take baby steps, and if there's anything that feels wrong about the changes, you can stop. Sometimes the only way to know if this is right for you is to take the plunge. I wish you a lot of luck and kindness, What am I, because this is a rough old world for gender-queer people.