Helena, 63, Chicago, IL

I feel very isolated. I don’t feel whole. There’s still that hole in my middle, the stomach is not filled, I’m not fed completely. And I wonder whether or not I will ever have that feeling of being embraced. When I pretended to be a gay male I could pretend to be a part of the gay community. And it looked good on paper and the surface. Sometimes it worked. But as trans it doesn’t work. You have to find a collection of trans friends that you can depend on.

My roommate warned me. She said, “Let me get this straight. You want to be a middle aged, black woman. Oh yeah? Really?” And I said, “Yeah.  Look out world.  Here I come.” You have to have a sense of humor. And choose your battles very carefully, because they do have emotional ramifications that produce stress. I try to cut down on stress. It’s not productive. One of the reasons I switched over to the Afro-centric clothing and the hair and all of that is I don’t like where the mainstream puts women, visually. And it’s all visual. It’s like we don’t have any insides. So I thought, well, okay. I’m already isolated. The advantage to being isolated, it gives you permission to really be who you are, because you think nobody really cares. And I’m tired of trying to prove something. So I’m just gonna be.

Every day I try to do one something for someone else, that I don’t necessarily know. That helps me not feel isolated. They say you’re not really giving until you can feel it. So if you’ve got five dollars and you give four of them away you feel it. I heard some kids saying, “Ma, can we have some fruit? We haven’t had fruit in a long time. We haven’t had fruit since you got that check from the IRS.” I thought, “My God, it’s June.” When did she get that check? And they really wanted this fruit. I could see the pain on her face, a mother having to say no. And there were four of them. So, I went up to the register, cause they know me in Joe’s on 95th Street. And I said, “When they come up, all this fruit that I brought to you is for them. And I’m gonna pay for it. And you better not tell them. Just put it in their cart. And if they say anything, say, ‘Somebody wanted the kids to have the fruit.’ That’s it.” One nice thing a day. 

Chris, 52, Boston, MA

I feel like I was always punished for my masculinity when I was female-designated by both straight people and lesbians. I was not the kind of woman that either women or men wanted to be around. I was way too scary, and people didn't know what to do with me. I was always a fish out of water in terms of my gender presentation. In a huge way, my transition has been like nirvana for it to get all aligned with me, and then have the world treat me well while I'm aligned has been amazing. I mean just really amazing for me. So I lived in that lesbian world even as it was difficult to do.

I actually gave birth to both of our children, which was never inconsistent with my sense of still being a man and being pregnant, and I know that many people can't understand that, or they might have some understanding. But it was not inconsistent for me to be with my male identity and want to have children.

Integrating all of our identities as a family has been a journey. So my spouse and former spouse identify as lesbians, my kids identified as part of a lesbian family, so applying to colleges, how do you explain on the FAFSA forms for the federal government that somebody's a biological mother and at the same time they're legally a man and what's their legal relationship, and how do you explain that I am legally a man that was never married to my former spouse who is legally their mother because we were a lesbian couple? 

So there's layer upon layer upon layer of complication when interfacing in the world, even as it was not very much of a blip in terms of my family's experience of me and didn't change a whole lot the way our family life ran, was not really that big of a deal. And yet, this interface out in the world became a pretty big deal.  

Grace, 56, Boston, MA

I always felt more like girls, like women. Even when I was watching movies or television shows or reading books, the female characters were the ones that I identified with just sort of instinctively. So I knew I was born male, but I certainly was a feminine boy growing up, a gender queer boy, and was harassed and bullied and got a lot of negative attention because of that. I was assumed to be gay from the earliest get go as well, even though it wasn't talked about then in the ‘60s. So – I was called all the names associated with that: sissy, faggot, fairy, all of that.

I didn't feel like I was transsexual. I didn't have that profound sense of body dysphoria that lots of transsexuals report, even though there were things that I wanted to change – so the way I understood that and was able to express that in the '80s was maybe what we would now call gender queer. That term wasn't used then, but I lived in another gender space. I just was living in this third gender space. I didn't see it as on my way to anything. I've been lucky to have people in my life who have been supportive of me and my journey, wherever that would lead me. So it was less about giving me guidance on a specific path and more about people who have said, "Your identity's evolving, and that's a wonderful thing, and we encourage you to explore that and go with that." 

I still see myself as on a journey. When I received an award a few years ago at a conference I said, "In the '60s they called me a sissy. In the '70s they called me a faggot. In the '80s I was a queen. In the '90s I was transgender. In the 2000s I was a woman, and now I'm just Grace." 

Michelle-Marie, 62, Williamsburg, VA

I had an older sister, a younger sister and a younger brother. And I just identified more with my sisters than I did my brother. I just wasn’t a boy. And growing up, I really knew nothing. The only person I knew was when I took my mother’s Life magazine of Christine Jorgenson and hid it. Later on, I found Renee Richards’ book, Second Serve, and kept it. Those are the only people I knew about. 

My mother always told me when I got beat up, “if you weren’t that way, it wouldn’t happen.” I left home two weeks after high school graduation. I was scared of getting drafted into the Army, so I joined the Navy. But I had some bad experiences in the Navy, so I managed to get out early. Then I did everything you’re supposed to do. At 22 years old, I got married. I had three kids. I had a career. I was a program administrator. And I just never learned – I never took on male socialization skills. And in 1990, I had a massive breakdown. I didn’t know who I was. I hated myself.

So then the next 12 years, I was in and out of psychiatric hospitals. I attempted suicide 14 times. I was in a basement apartment and I was ready to do it again. Nobody was going to find me that time. But that time, I sat and thought about things. I drove home, drove to California, talked to my sister, and my sister said, “it’s about time.” 

Then, my father passed away in ’98 and he had told me before he passed away, he said I had to make some decisions in my life and only when I made them was I going to be happy. You know, it was the first time in my life he was proud of me, said he was proud of me. I just thought he meant I had to get over my depression. But my sister told me that he knew all those years what was the problem. So I came home and I literally left Mike in every trash can along Interstate 40. And I came back and started my transition.

Later on, I remember my therapist asking me, “what kind of a woman do you want to be after you transition?” And she made me go home and think about it, and I went back and I said, “I don’t have to think about that. I’ve always been that woman.” It’s only now the outside matches.

Charley, 53, Charlottesille, VA

I've lived in Charlottesville, Virginia all my life. I identify as male, and I've been on hormones now for almost three years. I lived as a male before the hormones for a year. I've struggled all my life with my identity, and was working with a therapist, and finally realized what was going on, and decided that the only way that I was going to be truly happy was to be able to transition. I've also been in recovery from drugs and alcohol. I'll pick up an eight-year medallion on May 22nd. So that's a major accomplishment in my life. 

I think the hardest part was – and still is – trying to get my family to accept. They still use the female pronouns. And I don't think I'll ever get them to that point. A few years ago, that would have really bothered me, that they have not accepted it. But I've got to realize that they're on their own path, whatever path they're on. And I'm on mine. 

In the beginning, when I started transitioning, when my features started changing, when it got to the point where I was totally male, I wondered why people were treating me differently. Other races were treating me differently. And I realized, I'm a black male now, and so when I step on the elevator, the woman's going to clutch her pocketbook, or she's going to move to the other side of the elevator, or I get doors slammed in my face. You know? 

But I will say that being a male – not so much just because I'm a black male, but being a male – I believe I have gotten better jobs because of being a male. Because I don't have to sit across that table with somebody interviewing me as a butch lesbian, and they're trying to figure out: "Okay. Is this a male? Is this a female? Do we want this person with this large question working for us?"  But I have gotten more jobs, and as time goes on, better jobs because of being a male. I really believe that. 

Going to therapy was probably one of the most freeing things that ever happened in my life. And transitioning at 50 probably saved my life. Because at the rate I was going, I was going to start drinking again – and if I started drinking again, I was probably going to hurt myself. That was the way I drank, I was so miserable being inside this body. I had not been able to hold down a relationship, because I was such an angry person. I had a lot of anger issues. I had a lot of self-esteem issues. My confidence level was very low. I had some intense therapy to really get to know who I was, before I started into any of the transition. I am such a whole person now, for going through this. I'm more happy with life. I'm not dating anyone right now, but I know the next relationship that I go into – that person's going to be damn lucky. Because I've got my shit together. I've got my game on. 

Bobbi, 83, Detroit, MI

I have traveled extensively, it started out when I was in the Air Force. I was the “grandfather,” or whatever you'd call it – of the drone program. I mean, I played golf with presidents, with Jerry Ford and whatnot, and I certainly have met the older Bush and younger Bush and Reagan a couple of times. I've been in the White House. I've been up and down the Pentagon, all levels. And I've also worked extensively with the CIA.

Eleven years ago was my surgery, to this date almost. Eleven years ago, so I started hormones 12-plus years ago. And I really have been in the cross-dressing business or the transgender business since I was probably 4 or 5 years old. I mean, I've got that history. But I didn't know some of that history until I tracked back later in life, when I saw this more obviously in front of me. I said, "Oh, my god, this is what I was doing when I was 4 years old and 5 years old and 6," and of course, it all fits into a channel. But in that day- I'm talking about being born in 1930- that was the Great Depression. There were no words for any of this. Except that I think my mother knew, because when I asked her to teach me to knit, she did, and she'd teach me some other things that I asked if I could do, like cross-stitch and whatnot. So all the basic clues were there all the way along.

I think people talk in either/or terms, right? Before transition and after. But to me it’s really development.  I'm proud of both lives. I'm proud of both me’s, if you see what I'm saying.  And I feel it's been a remarkable thing to have happened to a person. I’m grateful. You can't just become a woman with a knife or a pill or anything like that. It takes a whole combination in a sequence, in a formation. You've got this time span, it's a learning experience, it's a little bit of everything. It's what I call going through the internship phase, stumbling through the adolescent phase, then going through the maturity phase. 

I have gone through the dating routine. That was my internship. I had to get through the Internet, go out and stumble on with it and flirt, and I got pretty good at it. I kinda worked at it. I'm not bad with words.  And I could play peek-a-boo on Skype. Then I finally picked up Frank. I kidnapped him from the local bar up here one afternoon, an ex-Marine. And we dated for a long time. Finally one day, it was so nice that Sunday morning with our head on the pillows, I said, "oh, I got something to tell you..." And after I told him he says, "you're better than any woman I've ever met. Now, come on, Bobbi, we can drop that." Didn't care a damn.  Where I live now, I think some people know for sure who I am and don't really care. But I also don't have it written on my forehead. So there are those that don't. They just take me as another old lady, a nice old lady.

Mickey, 60, Chicago, IL

I have an older sister, who's four years older than I am, and my dad raised me as his son. I was his son, except for those times when I had to present as a little girl. I mean, you knew – I knew when those were. No one told me, "That's bad. You can't be a boy." They didn't say that. There was just this given "You will dress like this for this occasion." It was really uncomfortable for me to be in a dress, but I would do that, if my family went to the relatives’. But I mostly dressed then like I do now. “I like to wear T-shirts and jeans." And that's what I wore when I was kid. I identified as a boy. But there came a time when I went to school and kindergarten, where I had to wear a dress. I mean, this was a long time ago, and little girls had to wear dresses, and so that's what I did. I didn't resist. That's what I was supposed to do.

I remember the times when I realized I was different from the neighbor boys – I think I was about 10 or 11, and I was boxing. My dad was a boxer in high school, and we were boxing, play boxing or real boxing, or whatever we were doing, and the boys in the neighborhood told me I had to take my shirt off, because that's how you box. And it was that moment when I realized, "No, I'm not supposed to do that." They could, but I couldn't. And it was really disheartening. It made me angry that I couldn't do what I wanted to do and be who I was. Suddenly puberty was setting in, and that changed everything. 
As an adult I did drag with the Chicago Kings for several years, and it was really exciting for me because it gave me permission to wear really nice men’s clothing. I would find these vintage jackets that I always wanted to wear, but unlike some of my friends, I hadn’t felt comfortable doing it. I have friends who had been wearing suits and ties forever, and some have transitioned and some have not, but it's the suit and tie that made them feel comfortable. So, it was great to perform with the Kings because it was this community that allowed me to explore so many things around gender, and allowed my colleagues at school to see me perform and to wear this male attire. That was the beginning of me being really okay with my gender nonconforming, my gender variance.  

I think that this is a wonderful time to be trans. It's not perfect, for sure. There is a lot of work that needs to be done. But I'm doing it, and lots of people are doing it. I love that Laverne Cox is on the cover of Time magazine. I have to go buy one today. I feel lucky to be living in this time. 

Renee, 68, Chicago, IL

I think first of all that I'm more bi-gender than purely transgender.  I enjoy both genders, and I miss the one I'm not.  And it's been like that for as long as I've been able to peel away the layers and get to it.  So most of my life, I denied it.  I just kept it buried.  One of the things that's been frustrating for my wife is it's come out by one struggling inch after another.  I, like many of my generation, buried it so deep and wrapped it in subterfuge. 

My wife’s been very supportive, and that helps immensely.  I mean there are not very many wives that stay with male-to-female transgender people who come out, and yet she's encouraged me to investigate who I am and what I am.  And even going back years when I first came out to her, neither of us really knew where I was, what I was.  It could have been the end of our marriage. 

The other thing, as I've thought about transitioning over all the years, is I've come to realize that really what I want isn't – it's not female plumbing.  It's not even necessarily a female body.  It is an opportunity to just express who I am at any given time.  After I came out to my wife, I did a lot more exploration, and truthfully, it's still going on…I have a pretty good idea that I am never gonna transition.  That was when I also realized that I didn't hate being masculine.  The only sense of deprivation I felt was that I couldn't also be feminine.  And it was around that time I started going to functions in Chicago that involved younger trans people, and they were using "genderqueer" as an expression.  I'm probably more genderqueer than I am one or the other.

Looking toward the future, I think about our grandchildren, and I wonder where they'll be in four or five years, and I hope that I can be here to be a part of that.  And I hope that we can stay healthy, and I hope that when my time comes, it's like – I remember seeing a 60 Minutes profile many years ago of this aging baseball team in Florida where the guy playing first base was like 90 years old, and they interview him, and he was talking about the guy he replaced who was in his 90s when he reached out to grab a throw and before the ball got there he died.  I said, "Boy, what a great way to go."

Tasha, 65, Birmingham, AL

I was born in Childersburg, Alabama. When I was growing up, I knew that something about me was different. I knew that I liked the guys. I pretty much today live as a gay man that lives just like a woman, because I see from Day One, from that day to this day, I've always felt like a woman born in a man's body. And that's the way I live. I live as a woman today. I didn't get to the place of where I'm so all right with this until later in life – at a young age I would’ve had a sex change. But today, I'm so all right with me it doesn't even cross my mind.

I have never been a case of being in the closet. I've always been wide open. And back in that time of the civil rights movement, I still didn't have any problem. I was still wide open. I participated in the marches and stuff. I was arrested, wet up with the hoses, all that stuff. 

Whether you say, "Yes, ma'am," or "Yes, sir," I'm all right. I don't let nothing like that bother me. At times it was kinda rough growing up when you had to hear guys call you all kinda names, such as freaking fag and all this kinda stuff.  It used to hurt me and make me angry. But as I got into the church and started letting the verse of John 3:16 register in me, a whole lot of stuff changed. 

It said, "For God so loved the world that whosoever will, let them come." And after that, I felt like I was one of the "whosoevers." And knowing that I was gay and knowing what people were saying, I stopped getting mad. I stopped fighting and just be who I am– and just be me. Now, I am real respected in my neighborhood as Tasha because a lot of people don't even know my real name. I'm Tasha to everybody. And most of the children say, "Miss Tasha." But when I come upon situations where children are curious and ask, "Are you a man or a lady?" I don't lie to them. I just tell them I'm a man that lives as a woman. And then I have no problems with them. If you don't say anything to me, I'm not going to say anything to you, although I have some eyes that can talk to you where I won't have to say anything. But, all in all, I feel that I done had a good life. I'm just happy with me today, real happy.