ME: Thank you for doing this interview, I think a lot of people may have similar issues. Now is Melissa Pindick your real name?
HIM: No, my real name is Tony and I’m an accountant.
ME: Alright Sir. You’ve told that me you’ve been crossdressing for most of your life, you must have a fantastic collection of lingerie, dresses, blouses, skirts, and heels.
HIM: No, I don’t. Actually I haven’t dressed up in over 10 years.
ME: Oh, and why is that Tony?
HIM: Well, I used to drink and I think a large part of the reason is the anxiety and guilt I have about this. I mean, I loved dressing up but it caused me so much stress that I eventually stopped. I used to buy things and throw them out, then do the same thing a couple of weeks later.
ME: That’s a shame, you know you could have packed them up and dropped them into a Red Cross box or something.
HIM: I guess so, but I was so nervous just bringing them to the dumpster that I was a complete wreck. I never would have thought of donating them.
ME: I understand, I really do. So do you still have crossdressing fantasies?
HIM: Oh yes, I think about it all the time. For example, yesterday I saw a picture of Carey Mulligan in the New York Post wearing a gorgeous white cotton bra. I thought about that all day long.
ME: I saw that too! Is this the picture?

HIM: Oh that’s it alright. As soon as I saw that I made up a complete fantasy scene in my head. The girls are dressing me up, and they hand me this bra. Then they say: “Isn’t this a pretty bra Melissa? You don’t have breasts yet but you will soon. Here, let me help you put it on.” Oh my God I’m getting excited all over again just thinking about it. This is a little embarrassing Teresa.
ME: Its OK, I’m sure a lot of people got excited by that bra. I even read the article to see if I could find out who makes it. The thing is though that a push up bra might not be the best choice for you, if you were to buy a bra which I guess you won’t.
HIM: I’d like to but it just feels so wrong. When I used to dress up it felt amazing, unlike almost anything I’ve ever felt, but afterwards I felt like a fool. I was ashamed, I felt guilty, and I kind of hated myself.
ME: I see. How often do you masturbate about these fantasies?
HIM: I guess every day, sometimes twice a day. I live alone so I have a lot of privacy. Its pretty much my whole sex life.
ME: So let me get this straight, you constantly fantasize about crossdressing, masturbate about it frequently, but don’t want to actually dress up anymore because it makes you nervous. Is that right?
HIM: Yes, that’s exactly right.
ME: Well I guess the interview is over.
HIM: But wait a minute, don’t you have any advice or magic words that will make it alright?
ME: No I don’t. You told me you’re 44 years old, I guess if you haven’t found a way to deal with this by now you’re never going to.
HIM: I kind of lied about that, I’m 61. I want to feel OK about it but I’m afraid of what other people might think, I always have been.
ME: Alright, you want some advice? You may have 20 years left, maybe more maybe less. So far this fear of what people might think hasn’t worked out too well has it? You might want to consider a different plan.
HIM: Can I call you once in a while and talk about it, kind of get reassurance?
ME: No. You’re a big boy or girl, whichever you choose to be. I’m not trying to be mean but life is about making choices, and sometimes the choices are very hard. (no pun intended)
HIM: I know, and thank you. Lets just say I did want a bra, what kind would you recommend?
ME: Now you’re talkin Melissa! I would suggest a Whispy Bra. Its all satin and lace and it has adorable little bows. You could even get it in white like the push up bra in the picture, but this will fit you better since you don’t have breasts.
HIM: Tell me a story Teresa, tell me how you’d slip my arms through and adjust the straps. Tell me what you’d do to me next.
ME: Listen Miss Pindick, you’ll put your bra on and like it. Sit there like a good girl while we do your hair and makeup. How was that?
HIM: Fantastic! But I don’t think I have enough hair left to do much with. What kind of wig do you think would look good on me? I like curls, always have.
ME: Good girl Melissa, such a good girl.
