The Secrets of My Life

Prologue

I am at the Marriott Hotel in Orlando giving The Speech to the sales force at Merck.

Six in a row one after the other, the same words and the same message and the same title and the same feigned enthusiasm just like the hundreds of other times I have given it forward and backward across the country. It is the 1990s. But it could be the 1980s or the early 2000s. They have all merged together.

I know why people are here in the audience. They are coming to listen to the Bruce Jenner who won the decathlon at the 1976 Olympics in Montreal and became dubbed, as is the tradition, "the world's greatest athlete." They are coming to listen to the Bruce Jenner who saved the United States Olympic Team from terrible disappointment at the hands of the Soviet Union and East Germany during our nation's bicentennial year. The Bruce Jenner who literally overnight became an American hero. The Bruce Jenner who is the essence of virility and is the ultimate conquistador of women. The Bruce Jenner who gets anything he wants. The Bruce Jenner who looks at himself in the mirror and sees a stud among studs.

They don't know that when I look into the mirror I see something entirely different, a body that I fundamentally loathe: a beard that is always noticeable no matter how close the shave, a penis that is useless except for pissing in the woods, a chest that should have breasts, a face with a jawline too sharp and a forehead too high. They don't know that contrary to what they imagine, I have slept with roughly five women in my life, and I was married to three of them.

They only know what they see, which is the image I have carefully cultivated over those decades, which in turn is the image the media has bought into because it's the irresistible story they want to tell: the Olympian who rose out of nowhere and was the son of a tree surgeon and went to a tiny college in the middle of nowhere and married his college sweetheart and spent almost half his life to win the gold medal. In doing so I have also come to represent, perhaps more than any other athlete of modern times, the America of hard work and realizing your dreams in which we all believe. The America I believe in no matter how unbelievable I have become to myself.

They know what they want to hear, a life defined by those two days at the Olympic stadium in Montreal, July 29 and 30, 1976, when I broke the world record and ran around the oval of the track afterward waving a small American flag handed to me by an adoring fan.

I was happy then, incredibly happy, proud of my country and myself. And it took less than twenty-four hours for me to realize that the greatest diversion in my life, the Grand Diversion, the day-in-and-day-out training of the previous twelve years, was finished. Which raised the terrifying question any day and every day: what the hell am I going to do? What the hell am I going to do with my life? How much longer can I keep this up? How much longer can I hide and lie to those who still admire me and those I love?

I go to bed with frustration and shame. I wake up with frustration and shame.

They don't know that underneath the dark blue business suit I am wearing panties and a bra and pantyhose. They don't know that I am not Bruce Jenner but a woman I will come to call Caitlyn, who still has to be Bruce except for stolen moments here and there, twenty minutes or an hour or maybe two where I can feel what it is like to be my authentic self.

Imagine denying your core and soul. Then add to it the almost impossible expectations that people have for you because you are the personification of the American male athlete. You can't imagine it.

I am glad you can't. Because it is unimaginable. Except to me. Because I am living it. Or trying to live it. Because you don't really live. You just try to get by, pray that the conflict inside will, well, not go away completely, because you tried that already and it won't, but maybe take a breather, move to the background of your mind instead of the foreground.

Those in the audience don't know that despite my outgoing nature and a natural gift for small talk—because I do like people—I am always uncomfortable.

All they know is what they want to know. And all I know is to tell them what they want to know.

The speech I give to the Merck sales force is called "Finding the Champion Within." I have no need for notes. I know it by heart:

There was a time I believed those words, particularly in the aftermath of the Olympics, when I was preoccupied with the bounty of success. But now a certain word comes to mind:

Bullshit.

All bullshit.

Ladies and gentlemen, please give a warm welcome to Bruce Jenner!

I am acting here because that's how it has been almost my entire life. I am playing Bruce because that's what the people listening to me want. That's what society wants. I get paid a lot of money for it. So I keep my mouth shut about who I am.

I finish up The Speech. I do the usual meet and greet afterward. I fake my way through by talking sports with the guys and making small talk with the women because I cannot relate what is in my heart. All I really want to do is get out of there and go up to my hotel room. The truth is I no longer give a rat's ass about The Speech. I do it so I can make a living, but I really do it so I can get out on the road. Because it is only on the road that I can feel any self-fulfillment; my wife, Kris, will not permit any of this behavior at home, just like my two wives, Chrystie and Linda, before her. She doesn't want to see it or deal with it, so we never talk about it. Why would she? She fell for Bruce Jenner, not some porcelain doll knockoff. They all did.

I wasn't totally honest with any of them. I was too ashamed. Too scared. But it was more than just that. Just like my ex-wives, I couldn't conceive of it either. Bruce Jenner?

Be serious.

Of all the people in the world, could anyone be more unlikely?

Bruce Jenner?

I lock the door to my suite at the Marriott and put out the DO NOT DISTURB sign. I order room service, a tuna sandwich and a Diet Coke, and tell the waiter to just leave the tray outside the door. I turn on the television to sports that interest me, car racing and golf. There are several mirrors in the suite, which I like. The bathroom also has a makeup mirror, which I also like.

I'm in business.

The ritual actually begins before I even get to the Marriott. It starts at Los Angeles International Airport, where I have taken every possible precaution I can think of to get through security without incident.

Nobody enjoys packing. But try packing for a man and a woman. I have a female friend who buys clothing for me since I am too scared to do it myself. I tell her what I need and she looks for it. But given that I am six feet two inches tall and can't try anything on in person, it's hit or oftentimes miss. Shoes are particularly tricky because of my big feet, good for the events in the decathlon but not so good when you are trying to dress up without detection. The selection is further limited because I am assiduously avoiding heels that are too high: the last thing I need is to be taller. So it actually makes packing easier since I don't have many options, either for this trip or the dozens of trips I have already taken.

I layer the outfits I am going to wear at the bottom, then I stuff a wig inside the sleeve of one of the garments and fold it over as extra precaution. I put my dark blue business suit on top along with assorted socks and shirts and underwear. This is before 9/11, so security isn't nearly as stringent as it is today. If I am stopped and my luggage is searched for some reason, I can always say that I packed for both wife and husband. I have an excuse ready for any situation. Always think on your feet. Deny, deny, deny. But I still want to avoid questions, and a woman's wig on the top layer is far more likely to cause snickers and speculation that Bruce Jenner is at a minimum an Olympian-sized kinkster. I always bring a box of clear plastic wrap, which in my own homegrown method of feminization I cinch tightly around my waist to heighten my hips and buttocks. And let's not forget the little tube of Krazy Glue I use to do a makeshift facelift. After extensive trial and error and many different types of adhesives, I have learned that it adheres remarkably well, but it's a bitch to get off if you use too much, removing a tiny patch of skin and leaving a visible red blotch.

Fortunately I have gone to the bathroom before security to remove the breast prosthesis I am wearing. I actually forgot once, and the alarm went off as I went through the metal detector. As the officer positioned his wand on my upper chest, I was convinced the detector had picked up something on the bra. I braced myself for being marched to a private room to remove my shirt, and I am pretty sure saying the prosthesis was for my wife would not have worked. The fear was palpable, until it turned out that the wand had picked up a zipper on the rain jacket I was wearing. I was a lot more careful after that.

In this particular line of work it is always better safe than sorry.

I unpack and lay the clothing I will wear on the bed. Because I'm not one to experiment in a situation such as this, two items are almost always the same. One is a black dress with spaghetti straps at a length just above the knee, because if I know anything about myself, it's that the legs work. They have always been thin, much to the amazement of many, given my athletic success. I told them then that "my legs are made to go, not show." Now it's the opposite when I get the chance: my legs are there to show, not go. I can't say the same thing about my arms—definite no show—so the other item is a black jacket to hide them.

I stole the clothing from Kris's closet because it is quite sizeable and I do not think she will notice them missing. (By the time she discovered I had been "borrowing" them for several years, they had been stretched all to hell and she did not want them back anyway.)

It is my go-to outfit, cute but not too formal, complemented with black shoes because as we all know black makes you thinner. I have stolen makeup over the years not only from Kris but the rest of K-troop, Kourtney and Kim and Khloé and eventually Kendall and Kylie, because—trust me on this—there is more makeup per household user in our home than any in history. If you have watched Keeping Up with the Kardashians on the E! network, you probably know this.

Applying makeup is always the most intense, and I sometimes think I work harder on that than I did to win the decathlon. Although I have gotten better, it is still not a given as to how exactly I will look. In the past, I secretly bought how-to books since there was no one to help me. I keep the books, along with my meager collection of clothing, in a small closet with a lock and key in back of my own closet. Kris and I have negotiated this, since she is terrified, as I am, of the kids finding something.

It almost happened once with Kendall and Kylie. One suspected the other of stealing clothing—I don't remember who was the detective and who was the alleged perpetrator. I do remember that one of them secretly activated the security camera on their computer. With everyone out of the house I dressed up. I went into Kylie's room to check myself out because it had a full-length mirror. I thought nothing of it until later that night when I heard them running to their mother yelling, Oh my God, what's on the computer screen?!

They were mercifully too young to understand. It sounds funny now. It is funny. But not then. The embarrassment I felt was profound. I didn't want any of the kids to know. I didn't want to confuse them or scar them or hurt them. How could they possibly come to grips with this when not even I could? The episode was symptomatic of the tissue of lies I had built, never at peace with myself, total confusion.

Fortunately the episode was forgotten. But I learned a valuable lesson:

whenever the woman inside you wants to check herself out in the mirror in your kid's bedroom, make sure the computer is turned off.

The eyes are the most important, because eyes of course are a window into the soul; you get the eyes right and everything else follows. They come out fine; I am definitely improving. But sometimes I get overconfident, and here I am, the world's greatest athlete, sitting there with my hands shaking trying to put false eyelashes on, which only results in black glue all over my eyelids.

I look at myself in the full-length mirror of the hotel room. I walk back and forth several times to make sure I am passable enough as a woman. I carry a purse—Kris's, of course, which is a little bit harder to "borrow" since she started keeping better track.

I leave the room. I usually take the stairs to the lobby to avoid getting stuck on the elevator with other guests. But I am on a high floor and don't want to exit looking a mess. So I use the elevator. I don't say a word because my voice, singsong and a little bit high-pitched, a combination of Midwest solid and Massachusetts twang, will give me away instantly after so many years in the public spotlight. I turn my back as if I am a disinterested, stuck-up broad, and I bend my knees a little bit to not look so tall.

I leave the elevator and walk around the lobby for twenty minutes, not a very good return on investment, since it took at least an hour to get dressed. It's exciting to me, and I sometimes wonder if that is the driving force, finding excitement in a life that no longer has any excitement unless you call playing golf by yourself exciting, and believe me it's not. Living with the Kardashian women and Kendall and Kylie is incredibly rewarding—don't get me wrong. They are dazzling, and in several years' time, Keeping Up with the Kardashians will draw millions of viewers worldwide. I come across in the reality show as a well-meaning but slightly doddering patriarch who has no life of his own and is subsumed by the women who surround him and only does what his wife tells him.

In other words: a totally true depiction.

I walk to the end of the Marriott lobby and then turn around and go back up to the hotel room. I never linger. I never stop. I never go to the restaurant. I look for remote crevices and corners. I try to avoid eye contact as much as possible although I am acutely aware that I am being checked out. As Bruce Jenner I have already been checked out thousands of times.

The reason for the looks is different now. I am not too worried about being recognized, because even if someone thinks they see Bruce Jenner in a dress (which they did), nobody is still going to believe they just saw Bruce Jenner in a dress because Bruce Jenner is the last person you would ever expect to be wearing a dress if you have the slightest memory of the Olympics. The reaction that concerns me is whether or not I am presentable. The length of the glance is the key determinant: a quick one means no big deal, it's just another woman. A longer one worries me, the implication being what the hell is that? Sometimes I think I look pretty darn good. Other times I feel like a thinner version of Big Bird, standing out for the world to see and snicker at after I pass. There are very few good things about getting old. Except that you shrink. So if I live to be one hundred, I will be five foot ten and maybe not feel so self-conscious.

I think about these things.

I remember once in another hotel how a man came up to me in the lobby. I was convinced this was it—busted. Instead he smiled and handed me a rose. I returned the smile and got away from him as quickly as I could. The last thing I wanted was a conversation. In the dozens of outings I have made to hotel lobbies over the years, I have never had a conversation with anyone. But I was flattered.

I leave the Marriott and get into my rental car and drive around for an hour or so. This is something I also would do, depending on mood and how much time I have. I see a strip mall and park the car on the outskirts of the lot, as far away as possible from any security lights. I walk around for a little bit, holding the car keys in my hand in case of an unexpected encounter that requires a quick dash back to the car. Thank God I am in sensible shoes. I do not stay out very long, but even the freedom of walking around in the farthest corner of a mall parking lot is still momentarily liberating. It is incredibly exciting—the pulse quickens, the heart rate rises, a combination of giddiness and confidence and daring the world and happiness, sublime happiness.

Going back so many years to the age of ten, I am still trying to figure out why. Am I truly gender dysphoric, clinically defined by the American Psychiatric Association as "a marked incongruence between one's experienced/expressed gender and assigned gender"? Am I maybe just a cross-dresser deriving some sexual high? Sometimes I wonder if dressing up like this is the equivalent of having sex with myself, male and female at the same time. I have no concrete answers.

Occasionally I venture out even beyond the parking lot. Like the time I was staying at the Opryland Hotel in Nashville. The Opry Mills mall is across the street. There was a multiplex cinema and I thought, What the hell, why not go to the movies by yourself?

I went over earlier in the day and had Bruce buy the ticket. That afternoon I gave the "Finding the Champion Within" speech. I went back to the hotel room and got fully dressed as the woman inside me. Then I walked to the multiplex and went right inside the darkened theater since I already had my ticket. I wanted popcorn—you have to eat popcorn when you are watching a movie, otherwise there is little point. But I was too scared to go to the concession stand. Fortunately the movie was good and I got into it, and for two hours everything else stopped.

I left the theater afterward and had to go to the bathroom. I doubt that for anyone else there it was a complex decision—you have to go, so you go. For me it was Oh my God, now what am I going to do? I had actually used the women's room before during previous outings. Like everything else I had a particular routine: I would wait outside to make sure no one else was entering. That way I could go in by myself and use the stall farthest away from the door. If somebody came in I would wait until she left. Then I would get the hell out of there.

The line for the women's room was lengthy that day. There was no way I was going to wait. So I scuttled back to the hotel as quickly as I could and made it up to my room.

I am still feeling good about myself when I get back. Nobody suspected anything. But I have an early flight tomorrow, which means Bruce will be back, rise and shine. Everything has to come off, unless I have a late departure. Then I sleep with the makeup on all night and it smears all over the pillow (sorry, housekeeping). Outwardly my life is good: terrific children, a strong marriage (at least before Keeping Up with the Kardashians takes off), steady work, a public that likes me. I continue to have a positive image.

It is not enough. It will never be enough. At this point in my life in the 1990s, in my forties, I honestly don't think I will ever get that peace in my soul. Concerns over family and the strictures of society are just too great.

I seriously think about putting a stipulation into my will that I be buried as was always my gender. Maybe that's the best and only answer to be the woman I always was, wearing what I always wanted for more than twenty minutes in a hotel lobby or going to a movie in the dark or driving around aimlessly.

That's the way I want to go to heaven. That's the way I want God to see me so I can finally ask him:

Did I blow it? Was there more I should have done?

I yearn for the answer here on Earth. But until I find it I do what I do best. I play Bruce.