CO VER STORY

Cait­lyn Jen­ner speaks can­didly about her dou­ble life as Olympic ath­lete Bruce, and the joy of fi­nally be­ing the woman she al­ways knew she was

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Iam at the Mar­riott ho­tel in Or­lando giv­ing The Speech. The same words, the same mes­sage, the same ti­tle, and the same feigned en­thu­si­asm – just like the hun­dreds of other times I have given it all across the coun­try.

I know why peo­ple are here in the au­di­ence. They have come to lis­ten to the Bruce Jen­ner who won gold in the de­cathlon at the 1976 Olympics in Mon­treal and was dubbed ‘the world’s great­est ath­lete’. The Bruce Jen­ner who be­came, overnight, an Amer­i­can hero. The Bruce Jen­ner who is the essence of viril­ity and 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 in 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 been 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 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 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, who mar­ried his col­lege sweet­heart, who spent al­most half his life work­ing to win that 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 re­al­is­ing your dreams.

They know what they want to hear: a life de­fined by those two days at the Olympic sta­dium when I broke the world record and ran around the track wav­ing a small Amer­i­can flag handed to me by an ador­ing fan. They don’t know that un­der­neath the dark blue busi­ness suit I am wear­ing panties, a bra and tights. They don’t know that I am not Bruce Jen­ner, but a woman I will come to call Cait­lyn; a woman who still has to be Bruce, ex­cept for stolen mo­ments here and there, 20 min­utes or an hour where I can feel what it is like to be my au­then­tic self.

Imag­ine deny­ing your core and soul. I am glad that you prob­a­bly can’t, be­cause you don’t re­ally live. You just try to get by, pray that the con­flict in­side – it won’t go away com­pletely; you tried that al­ready and it won’t – will maybe take a breather, move to the back­ground of your mind in­stead of the fore­ground.

Those in the au­di­ence don’t know that I am al­ways un­com­fort­able. I am act­ing here be­cause that’s how it has been al­most all my life. I am play­ing Bruce be­cause that’s what peo­ple lis­ten­ing want. That’s what so­ci­ety wants. I get paid a lot of money for it.

I fin­ish The Speech. I do the usual meet and greet af­ter­wards. 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 go up to my ho­tel room be­cause it is only on the road that I can feel any self-ful­fil­ment: my wife Kris will not per­mit any of this be­hav­iour at home, just like my two ex-wives, Chrystie and Linda. 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 knock- off. They all did. I wasn’t to­tally hon­est with any of them. I was too ashamed, too scared. But it was more than that. Just like my ex-wives, I couldn’t con­ceive of it ei­ther.

I lock the door to my suite at the ho­tel and put on 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. There are sev­eral mir­rors in the suite and a make-up mir­ror in the bath­room, which I like. I’m in busi­ness.

The rit­ual ac­tu­ally be­gins be­fore I even get to the ho­tel. It starts at the 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. Given that I am six feet two inches tall, it’s hit and of­ten miss. Shoes are par­tic­u­larly tricky be­cause of my big feet. The se­lec­tion is fur­ther ➤

Peo­ple want Bruce: the world’s great­est ath­lete, the Amer­i­can hero, the essence of viril­ity

➤ lim­ited be­cause I as­sid­u­ously avoid high heels: the last thing I need is to be taller.

I layer the out­fits I am go­ing to wear at the bot­tom of the case, then I stuff a wig in­side the sleeve of one of the gar­ments and fold it over for ex­tra pre­cau­tion. I put my dark blue busi­ness suit on top, along with as­sorted shirts and un­der­wear. If I am stopped and my lug­gage is searched I can al­ways say that I packed for both my wife and me. I have an ex­cuse ready for any sit­u­a­tion. Al­ways think on your feet.

I al­ways bring a box of clear plas­tic wrap, which, in my own home­grown method of fem­i­ni­sa­tion, I cinch tightly around my waist to heighten my hips and but­tocks. And let’s not for­get the lit­tle tube of glue that I use to do a makeshift facelift.

For­tu­nately I have gone to the bath­room be­fore air­port se­cu­rity to re­move the breast pros­the­sis I am wear­ing. I 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 would pick up some­thing on the bra. I braced my­self for be­ing marched to a pri­vate room to re­move my shirt. The fear was pal­pa­ble un­til it turned out the wand had picked up a zip­per on the rain jacket I was wear­ing. I was more care­ful af­ter that.

At the ho­tel, I un­pack and lay the cloth­ing I will wear on the bed. Be­cause I am not one to ex­per­i­ment in this sit­u­a­tion, two items are al­most al­ways the same. One is a black dress with spaghetti straps that falls just above the knee, be­cause if I know any­thing about my­self, it’s that the legs work. They have al­ways been thin. I can’t say the same about my arms – def­i­nite no show – so the other item is a black jacket to hide them.

I stole these clothes from Kris’s wardrobe be­cause they are quite big and I did not think she would no­tice them miss­ing. (By the time she dis­cov­ered I had been ‘bor­row­ing’ them for sev­eral years, they had been stretched so much she did not want them back any­way.) It is my go-to out­fit – cute but not too for­mal, black be­cause, as we all know, black makes you look thin­ner. I have stolen make-up over the years not only from Kris, but also from the rest of the K-troop: Kourt­ney, Kim and Khloé, and even­tu­ally Ken­dall and Kylie, be­cause – trust me on this – there is more make-up per user in our home

I have been act­ing al­most all my life. Imag­ine deny­ing your core and soul

than any in his­tory. Ap­ply­ing make-up is al­ways in­tense and I some­times think I work harder on it than I did to win the de­cathlon. I se­cretly bought how-to books since there was no­body to help me. I keep the books, along with my mea­gre col­lec­tion of cloth­ing, in a small locked closet in the back of my wardrobe. Kris and I have ne­go­ti­ated this, since she is ter­ri­fied, as I am, of the kids find­ing some­thing.

The eyes are the most im­por­tant, be­cause they are, of course, a win­dow into the soul: 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’, with my hands shak­ing, try­ing to put false eye­lashes on, which only re­sults in my get­ting black glue all over my eye­lids.

I look at my­self in the full-length mir­ror. I walk back and forth sev­eral times to make sure I am pass­able enough as a woman. I carry a hand­bag – Kris’s, of course, which is a lit­tle harder to bor­row since she started keep­ing bet­ter track of her things. I leave the room. I usu­ally take the stairs to the lobby to avoid get­ting stuck in the lift with other guests. But I am on a high floor and don’t want to leave look­ing like a mess, so I use the lift. I don’t say a word be­cause my voice, singsong and a lit­tle high-pitched, will give me away in­stantly af­ter so many years in the pub­lic spot­light. I turn my back as if I am dis­in­ter­ested, a stuck-up broad, and bend my knees a lit­tle to not look too tall.

I leave the lift and walk around the lobby for 20 min­utes, not a very good re­turn on in­vest­ment, since it took at least an hour to get dressed. It’s ex­cit­ing, and I some­times won­der if that is my driv­ing force. (Liv­ing with the Kar­dashian women 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 ➤

➤– a to­tally true de­pic­tion.) I walk to the end of the lobby and then turn around and go back 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.

I am not too wor­ried about be­ing recog­nised, be­cause even if some­one thinks they see Bruce Jen­ner in a dress (which they did), no­body would be­lieve it be­cause Bruce Jen­ner is the last per­son you would ever ex­pect to be wear­ing a dress. What con­cerns me is whether or not I am pre­sentable. The length of the glance is the key de­ter­mi­nant: a quick look 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.

I re­mem­ber how once in another ho­tel 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 ho­tel, get into my rental car and drive around for an hour or so. I park the car on the out­skirts of a shop­ping mall, as far away as pos­si­ble from any se­cu­rity lights. I walk around for a lit­tle bit, hold­ing the keys in my hand in case of an un­ex­pected en­counter that re­quires a quick dash back to the car. Thank God I am wear­ing sen­si­ble shoes. I do not stay out for very long, but the free­dom of walk­ing around in a car park is mo­men­tar­ily lib­er­at­ing. It is in­cred­i­bly ex­cit­ing: the pulse quick­ens, the heart rate rises, a com­bi­na­tion of gid­di­ness, con­fi­dence and dar­ing the world – and hap­pi­ness, sub­lime hap­pi­ness.

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. I sleep with the make-up on and it smears all over the pil­low.

Out­wardly, my life is good: I have ter­rific chil­dren, a strong mar­riage (at least be­fore Keep­ing Up With the Kar­dashi­ans took off), steady work and a pub­lic that likes me. But it is not enough. It will never be enough. At this point in my life – the 1990s, I’m in my 40s – 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 a woman. Maybe that’s the best and only an­swer: to die the woman I al­ways was, wear­ing what I had al­ways wanted to wear (for more than 20 min­utes in a ho­tel lobby or driv­ing around aim­lessly).

That’s the way I want to go to heaven. I yearn for the an­swer here on earth. But un­til I find it, I do what I do best. I play Bruce.

***** I watch the TV in­ter­view at the home in Hid­den Hills, Los An­ge­les, where Kris and I once lived to­gether. All the Kar­dashian kids are here, with the ex­cep­tion of Rob. Ken­dall and Kylie are on a sofa in the liv­ing room. Kris is sit­ting be­hind us on a chair. How shocked or not she is by my tran­si­tion is im­ma­te­rial at the mo­ment: it has to be very, very weird to see your for­mer hus­band of 23 years, with whom you have two chil­dren, go on tele­vi­sion in front of an es­ti­mated 17.1 mil­lion peo­ple and say: ‘For all in­tents and pur­poses, I am a woman.’

Wow. I can’t be­lieve I just said that. I am a woman.

Do you know how in­cred­i­ble that sounds, how I never thought those words would come ex­cept in mo­ments of beau­ti­ful pri­vacy with a hand­ful of oth­ers?

The se­cret is out af­ter 65 years. Say it again to the heav­ens so God can hear it and smile. I am a woman!

Ken­dall and Kylie, who be­tween them have more than 200 mil­lion fol­low­ers on In­sta­gram and Twit­ter, start hit­ting so­cial me­dia al­most im­me­di­ately af­ter the in­ter­view has be­gun. Their sis­ters join in.

Ken­dall gives the ini­tial re­sults: ‘Dad, you should see the re­ac­tion you are al­ready get­ting, it’s in­cred­i­ble.’ It’s a great mo­ment. I go over to my daugh­ter Casey’s [with first ➤

I wasn’t to­tally hon­est with any of my wives. I was too scared, too ashamed

➤ wife Chrystie Scott] house in Santa Mon­ica and make it in time to watch it again at 9pm. All the Jen­ner kids are there with their spouses and sig­nif­i­cant oth­ers, as well as my ex-wives Chrystie and Linda. They, too, are elated with how the TV show went. Every­body in the three fam­i­lies is happy. At least for a day.

Sev­eral of the Jen­ner chil­dren were in­ter­viewed dur­ing the show, as were my mother and sis­ter. The Kar­dashian side feels slighted by their no­tice­able ab­sence. They are right to feel this way. They were slighted on pur­pose be­cause of the re­search show­ing that any time a Kar­dashian is on tele­vi­sion, many peo­ple think it is a pub­lic­ity stunt to make money.

I love my kids and the last thing on earth I want is for them to some­how think I am re­ject­ing them. But I needed to build a wall and dis­tance my­self for this in­ter­view. It was too im­por­tant. Af­ter all the time it has taken to get me to this point, I needed to make it clear that this was real, my life, and not some pub­lic­ity stunt. I couldn’t af­ford to add fuel to the ru­mour that I was do­ing it for the money. I had just one chance. This had to be about me and only me. If I screwed up then at least it would be on my own terms.

Much to my re­lief, the pub­lic re­ac­tion is phe­nom­e­nal. My hon­esty and sin­cer­ity have come through, no doubt be­cause I only have one ad­van­tage: I know how to be can­did, re­gard­less of the reper­cus­sions. The level of in­ter­est was amaz­ing, too: it gar­nered ABC show 20/20 its high­est rat­ings for more than 15 years.

I have made it through whole. I am still in one piece. But I’m not quite done yet. Wait un­til they see Cait­lyn for the first time.

Every­body has ad­vice about what I should wear for the Van­ity Fair photo shoot. The older Jen­ner chil­dren want me to tone it down – el­e­gant but not too flashy or re­veal­ing. Their in­ten­tions are good: they want me to set the right tone of wom­an­hood as they de­fine it. They are also sin­cerely wor­ried that the more glam I try to be, the more I will feed ac­cu­sa­tions of ex­ploita­tion. They are try­ing to pro­tect me. But their vi­sion of wom­an­hood is not my vi­sion of wom­an­hood.

The most res­o­nant ad­vice comes from Kim, who, as she points out, doesn’t sim­ply know fash­ion but is fash­ion: ‘You gotta rock it.’

Sev­eral weeks be­fore the shoot, the pho­tog­ra­pher An­nie Lei­bovitz comes to my house to scout the site and get to know me a lit­tle bet­ter. Van­ity Fair’s fash­ion and style di­rec­tor Jes­sica Diehl flies out from New York to meet me as well and find out what I like and what I don’t – or, more ac­cu­rately, what I shouldn’t wear, tact­fully steer­ing me away from big fash­ion

The re­ac­tion to my in­ter­view is phe­nom­e­nal. But I am not done yet. Wait un­til they see Cait­lyn

state­ments in favour of a mix of what she de­scribes as Rene Russo in The Thomas Crown Af­fair meets An­gelina Jolie, el­e­gant with a dash of tough.

The day be­fore the shoot, she and fash­ion edi­tor Ryan Young visit for a fit­ting. I had al­ways fan­ta­sised about hav­ing beau­ti­ful clothes that fit. As many times as I had stood in front of ho­tel mir­rors and thought I looked good, I al­ways knew it could be bet­ter, but I had con­vinced my­self I would never get the op­por­tu­nity. So now…

Some things have been shipped pre­vi­ously, oth­ers were brought by Jes­sica and Ryan. There are well over 100 dif­fer­ent pieces: gowns, blouses, sweaters, belts, cock­tail dresses, lin­gerie, jewellery, high heels. So many items that a tent is put up on my deck.

What is per­haps most amaz­ing of all is that none of the haute cou­ture shops where Jes­sica and Ryan searched for cloth­ing in New York asked who ex­actly these items were for, given that the per­son was six foot two.

Jes­sica thinks I have the look of a 1980s Ama­zo­nian model – which is what I may want carved on my tomb­stone, along with a quote from her say­ing I look per­fect in Tom Ford.

I ini­tially have trou­ble be­liev­ing that this is all for me to try on, the only goal be­ing to make me look my best. Ninety per cent of the cloth­ing fits. It is the first time I have ever openly tried on women’s cloth­ing in front of a group of strangers. It is so easy, so nat­u­ral, so ef­fort­less, so much fun; the way my life was al­ways sup­posed to be.

The shoot lasts for two days: An­nie Lei­bovitz is An­nie Lei­bovitz, af­ter all. She has a clear vi­sion of how she wants me to look: a lit­tle bit 1940s Hepburn, a lit­tle bit Var­gas girl; glam­orous and beau­ti­ful with a touch of sexy. The photo of me that is cho­sen for the cover, pos­ing in a cream bustier with per­fect make-up and hair and a head­line that sim­ply says ‘Call Me Cait­lyn’, will be­come in­stantly iconic. It is the pho­to­graph that ev­ery­one will re­mem­ber me by.

But the photo I re­mem­ber the most takes place in my garage, which has been con­verted into a stu­dio. I am wear­ing an off-the-shoul­der black gown by Zac Posen. It is a killer, if I do say so my­self. All the lights in the garage have been turned off, leav­ing only the ones set up for the shoot. There is dark­ness ev­ery­where ex­cept for on me, a spot­light ef­fect. There is a large mir­ror. An­nie tells one of her as­sis­tants to move it be­hind the cam­era so I can see my­self.

Not ev­ery day of my life will be spent with hair and make-up done, wear­ing beau­ti­ful cloth­ing hand­picked by a stylist, with An­nie Lei­bovitz tak­ing my pho­to­graph. In fact, it is safe to say that no day of my life will ever be spent this way again. But in that mo­ment when I look in the mir­ror, I truly see my­self for the first time. So many other times I have looked in the mir­ror with a fa­mil­iar loathing and dis­gust.

But now – now the view from the look­ing glass is dif­fer­ent. I see who I am. I am who I know. I know who I am. I am Cait­lyn. Cait­lyn Marie Jen­ner. For­ever for­ward.

It is so easy, so nat­u­ral, so ef­fort­less; the way life was sup­posed to be

Clock­wise from above left: as Bruce on the podium at the Out­door Track & Field Cham­pi­onship, 1971; cross­ing the fin­ish line to win gold in the de­cathlon at the Olympics, 1976; mar­ry­ing Kris Jen­ner in 1991, with (from left) Rob, Kourt­ney, Kim and (far right) Khloé Kar­dashian as chil­dren; aged two

Clock­wise from right: Cait­lyn with David Fur­nish, Boy Ge­orge and El­ton John; dis­cussing her tran­si­tion with Kim on Keep­ing Up With the Kar­dashi­ans; with Kourt­ney, Kim and Ken­dall

Clock­wise from above: Cait­lyn’s dad Bill in the army, 1944; as Bruce, aged 15, with Bill’s Austin-Healey Sprite; Cait­lyn to­day with her re­stored Sprite, a trib­ute to her dad

Above: Cait­lyn with Kris on I Am Cait. Right: Cait­lyn’s fa­mous Van­ity Fair cover

Read Cait­lyn’s full story… This is an edited ex­tract from The Se­crets of My Life by Cait­lyn Jen­ner, pub­lished by Trapeze and avail­able now, price €26.59.

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