Female Attraction: Q&A with Daniel Harris, author of Diary of a Drag Queen 

In his 40s, Daniel Harris hit a midlife crisis. His career as a writer had stalled and his sex life wasn’t going much better. Virile charismatic men he had once attracted, and now longed for, barely glanced his way. He was lonely. Then he discovered drag.

Harris’s 2005 book Diary of a Drag Queen is a humorous account of his experiences as a man, as a woman, and as an aging intellectual sidelined from the youth-obsessed gay world. (Click here to listen to Harris read an excerpt from his book.)

American Sexuality: Early on in your book you wrote about the fantasy of having sex with heterosexual men as being one reason for trying this experiment of dressing in drag. Can you talk a bit about that? How common is that fantasy in the gay community?

Daniel Harris: It’s very, very common. It’s also one of these things that gay men don’t like to talk about. It’s the sort of thing like—of course one never knows the truth—Asians like Caucasians and Black men like White women. It’s very much that sort of fantasy. … It is one of those secret longings that I think the majority of gay men suffer from…

One is looking for some kind of authentic masculinity and one is convinced that somehow straight men have the monopoly on authenticity, that gay men are only, at best, feigning their butchness. If you were taught your entire life that gay men are pansies and reprehensible, you’re going to look for your sex partners in another group of people.

AS: You wrote about your obsession with makeup and dress, and your complete dissatisfaction with your appearance. Can you describe that dynamic? Why continue your quest?

DH: At the beginning of this, you really don’t know how far you can push it; you don’t know how good you’re going to get, so these consumer potions out there are all the more appealing. You really think that you might stumble upon one that revolutionizes your appearance. Certainly, until I wasted quite a lot of money, that is what I believed, that I had just not found —what women refer to on cosmetic chat lines as the HG—the Holy Grail. For many, many months I was searching for my Holy Grail, thinking that it was a matter of putting on the right plaster. After a while though, after enough experimentation, I simply realized that I had come up against anatomy. There’s nothing I could do to disguise it. But at first it did offer this teasing promise.

AS: What would have made you satisfied? Did you aspire to look a certain way or were you seeking approval from the men you met?

DH: A little bit of both. I certainly had a look that I was aiming for, which goes to the heart of what I was willing to relinquish as a man. I wanted to look like a grand intellectual woman. So I aspired to be more handsome than pretty. Then, I was constantly disappointed by, really, the grotesque feedback I was getting from my mirror.

Of course prettiness is simply practical—it’s the way of luring men on the Internet. I didn’t have much problem because the lower part of my body is in very good shape. I look great in women’s clothing. My body is very passable as a very well developed woman. But my face is not. So there was always this tension between men who were excited by one thing but repelled by the other.

AS: You wrote about one man who requested you put a bag over your head.

DH: Yes, there was one guy who suggested he spare me the effort of my makeup and that I put a paper bag over my head.

AS: You laugh now, but how did that feel at the time?

DH: It was a painful thing. But once I was over the initial trauma of the blow, it started to tickle me. It’s the way I’ve dealt with trauma all my life. It was also very funny because he sent me an apology note that was, of course, written in cryptic Internet lingo, but it was very sweet and touching. He was a guy in his early 20s; I suspect he was foreign. He certainly did mean it; it wasn’t a joke he was playing. He really thought I’d go through with it, putting a bag over my head. … I’ve picked up drag again after a year and I’ve learned to really minimize my face with bushy wigs.

AS: Talk a little about your obsession with photographing yourself in drag.

DH: When I began the book I really thought of drag as a kind of prosthesis, something I could put on and take off, simple as that. It was just a utensil for sex. Then, as time went on, I discovered my prosthesis was actually firing sensations, like humiliation and shame and delight by the same token when I found something that actually made me look prettier or when a man was particularly excited by the sex we had and wanted to come back. So I became increasingly wrapped up in the importance of appearance. I went through a period of obsessive self-documentation, which displaced sex entirely in the routine. In fact, it began to edge out sex all together because I would come home and, when I would usually be cruising, I would take a hundred photographs of myself. By that time I was really too warn out to have sex. My prosthesis developed a real self-consciousness in the course of the project.

AS: What kind of men did you have sex with as a woman?

DH: I think a gay man, when he looks at another man, is attracted to the entire body, genitalia and all. When a straight man who may be interested in TGs or TVs looks at the body, he is exclusively interested in the genitalia. There seems to be two separate aesthetics for them, one that pertains to the man and one that pertains to their genitalia. With gay men there is one aesthetic; there is the body and the genitalia and they go together. I don’t know how people can separate the two, but it does seem a lot of my partners did that and were utterly repelled by the male body at the same time they were completely fascinated by dicks and balls. I guess this is such a phallic-central culture and that the dick expresses so much power to people that they can fetishize it alone. It’s very difficult for me, as a gay man, to understand how you can fetishize the dick without fetishizing the body. But this is what my tricks seem to be able to do.

AS: You also talked about some of your partners pretending to be surprised that they were with a biological male.

DH: I didn’t have anyone like that because I was very clear about what I was, but they would often recount to me their first experiences—what led to their careers as admirers of transvestites. It would be one of these Crying Game moments of revelation, that they had been deceived into the experience. ... I felt that was completely disingenuous but I thought it was a way that they could explain this to themselves. It’s like when you can’t control what happens to you when you’re bound if you’re doing S&M, so that you aren’t responsible for your sexual reactions. It was this sort of thing—they were so dismayed by the experience that they couldn’t be held accountable for their actions.

AS: Throughout the book you don’t seem interested in a long-term relationship. But did you ever fall in love with any of the men you slept with?

DH: I’ve been completely charmed by several of the men I’ve met. I have never seriously considered the possibility of getting involved with them since I don’t go outside of my apartment in drag; it’s hard to imagine that there would be any romantic future for me and them. I do continue to see one guy, for instance, with whom I’ve probably had more sex than with any other man. And I don’t even know his last name. I think he’s very sweet and very adorable but we simply can’t have any significant relationship. So I would say no. It’s crossed my mind that I should try something like this but…I basically find drag to be an incredible nuisance at this point and the thought of seeing someone regularly and dressing up three times a week is just a little overwhelming for me.

AS: Do you have any sexual partners with whom you interact as a man?

DH: I have had some flings here and there, but I don’t enjoy having sex as a man anymore. It’s dismaying to me. It’s also partly because all I do is put on a lamé thong and the median age of my sex partners plummets twenty, thirty years. The men I get as myself are not nearly as desirable as those I get when I’m in drag.

AS: What did you learn from this experience? Did you grow or change?

DH: I would not say I have grown so much. In many ways I digressed or devolved. I don’t think this book was the best thing to happen to me. I don’t think it’s good for me at this point of my life to become even more lost in my house. Internet cruising does that. It contributes to agoraphobia. I guess that goes against prevailing wisdom that every book must take you to a higher place. Well, I think this one’s taken me to a slightly lower one.