ANNA SALE: Where did the name Sissy come from? 

SISSY GOODWIN: Oh, the name Sissy. Well, I was, uh, I was in Laramie one day and this lady called me a sissy and, and I was really offended. Uh -

AS: She just walked by you and spat that out at you?

SG: Yeah. Yeah. She just, she says, "You look like a sissy." And I thought, I guess I am. And if I took the name myself, it took some of the sting off when people called me that. I owned it. I said, here I am, this is what I am and deal with it. 

This is Death, Sex & Money.

The show from WNYC about the things we think about a lot… 

...and need to talk about more.

I’m Anna Sale.

Sissy Goodwin lives with his wife, Vickie, in Douglas, Wyoming. It’s a city of about 6,000 people that’s also home to the Wyoming State Fair and the world’s largest jackalope. Vicky and Sissy have called Douglas home for most of their lives. 

VICKIE GOODWIN: I always kind of feel like there's a, uh, kind of a long rubber band that pulls us back to Douglas. 

AS: What’s it like here? 

SG: Kind of clique-ish. 

AS: Clique-ish, what do you mean? 

SG: Oh, if you weren’t born and raised here and had three generations you’re an outsider.

AS: So would you say in this community are you all outsiders or insiders, because you’re from here? 

SG: Well, I think, uh, I think we’re considered insiders although in some respects I still don’t feel part of the community. Even though I was born here and my grandparents homesteaded north of Douglas, I still really feel like an outsider.

I visited Sissy and Vickie at their home in Douglas. They live alone. Their two kids are grown. Their house is spacious, with high wood-beamed ceilings. And there are still a few 50th wedding anniversary decorations scattered around from their anniversary party there last year. 

SG: It just reminds us of a very fun and uh eventful day.

There’s a picture in their living room from that day. In it, Vickie and Sissy are beaming. They stand with their arms around each other next to a decorated cake. Vickie wearing a black silky embroidered blouse, and Sissy is wearing a silver ruched top with a short black skirt. 

VG: The outfit that he wore for our 50th anniversary was really pretty… 

It’s because of the way Sissy dresses—in very frilly feminine clothing—that he’s been made to feel like an outsider. Not just in Douglas, but in a lot of other places too. 

SG: I'm a male in every sense of the word, except the way I dress. I don't try to pass as a woman so I don't do makeup or fix my hair or anything.

AS: What words do you use to describe your gender identity?  

SG: I heard the term GEM. Uh, it’s an acronym for "gender enhanced male." And I like that term. The term transvestite has gotten some negative connotation, kind of a nasty negative stereotype. So I prefer gender enhanced male. I like uh to do typical male activities. I like to work with my hands, uh like to work outside. And so I'm, I think I'm typically male in every aspect except my mode of dress.

Sissy says he started dressing in girls’ clothing as a young kid. He remembers being left alone at home a lot, along with his younger sister. When his parents were gone, he’d put on his sister’s clothes. 

SG: it was pleasurable  for me, not in a sexual way, because I started dressing this way I can remember as early as four or five years old. I felt happy. Uh, when I started crossdressing, it was the early '50s and the styles that day were, uh, the girls always wore dresses, puffy sleeve dresses and I - dresses are pretty, you can twirl in them, the skirts will fly out, and petticoats, and just very pretty. And I, I, I felt pretty when I was dressed that way and it just gave me a diversion from a hostile environment. 

AS: Can you tell me more about that? What was your, what was your home like when you were a kid?

SG: Well, my stepdad was uh, he worked, he was kind of a vagabond, and he was violent. We moved around a lot because he, uh, would beat up on his bosses and that's not good for career development. 

AS: Like physically he would get in fights?

SG: Physically, he’d get in fights. And I remember one year my - in second grade we moved nine times, and I failed second grade.

AS: Uh huh.

SG: Uh, both Mom and Stepdad were alcoholics. There's a lot of violence in the family, uh lot of turmoil, a lot of moving. 

AS: And when you were dressing in your sister's clothes, was it something you did together or is it something you did in secret?

SG: Oh no, it was something I, we did together. My sister knew about it. 

AS: How old were you when you realized this was something that people might shame you for? 

SG: I guess in some respect I knew it was something that I would be shamed for because I kept it a secret. I tried to keep it secret from Mom and Dad and from my friends. I know in high school, even though I was very close to the few friends I had, I knew if they knew, uh, discovered the way I dressed in in private when I was at home, that they wouldn't be my friends anymore. I compensated by doing the typical masculine things that might be expected in Wyoming. I was in Future Farmers of America. I was on the high school rodeo team. So - 

AS: What what was your event on the rodeo team?

SG: Uh, bareback riding. And I - 

AS: Uh huh. So you, you rode bareback horses that were bucking and you're like trying to hold on?

SG: Right. I did ride bulls twice. My first time and my last time. It was the same ride. [Laughs] I was trying to cover and scared to death somebody would find out about me. So I was just, I think I went overboard trying to prove my masculinity to others and probably to myself. There's this saying in Wyoming called "cowboy up," which is, tough it out. Don't show your emotions, be a man. Hold it in. And I think that's the worst thing you can tell a young man because it's healthy to have emotions to experience those emotions, not to hold them in. 

But as a young man, Sissy did hold everything in. He joined the Air Force after high school and served in Vietnam. He says he was honorably discharged after a sergeant found him wearing a women’s nightgown in bed. Soon after he came home to Wyoming, he met Vickie. 

SG: I was working at the Casper airport and I'd stopped in at this little restaurant called uh Pink Kitchen Restaurant to have a supper about every night and Vickie was a waitress there and I just, she just was attractive to me, uh and I asked her out and I didn't even get a good night kiss that first date. She slammed the screen door in my face. I thought, you know, I'm not looking for a relationship. [Laughs] So much for this. 

AS: And what do you remember? 

VG: Well, I, I remember Sissy from high school, you know, and he ran with the, with kind of a lot of good looking, nice looking guys that I thought were pretty neat. And when he asked me out, I was just, wow, you know, this is really cool. But you know, I was the, uh kinda girl that didn't kiss on the first date. I mean, you know. 

SG: And I wouldn't of ask her out again except I uh seen her at college, and I thought, well, I give her one more chance. I’d ask her out out one one more time. 

They started dating steadily, and got engaged in 1968. It was right around then that Sissy told Vickie how he liked to dress in private. 

VG: He told me he liked to wear nighties to bed and women's underwear and, you know, and I, well, okay. You know, that's not a big deal. Um, the struggle for me came when Sissy began to be more open, you know, when, when he really felt the need to be who he was and that was a, that was really hard for me. 

SG: I started dressing openly and publicly just a couple of years after we were married. 

AS: So like the early '70s?

SG: Earl, early seventies. I came out gradually really. I started wearing peasant blouses and, and ladies' slacks in public. And then I graduated towards skirts and dresses. And the reason I decided to come out publicly was because I was having some pretty serious emotional and psychological issues. I would come home and, uh, put on a dress or a skirt and blouse and was just afraid somebody would find out about it and that sent a message to myself that you're a horrible, awful person. Why are you ashamed of who you are? And I knew that I had to, had to come out and and be myself. I couldn't live with that kind of psychological stress and torment anymore.

AS: The first time you were dressed in women's clothing and you went out in public, do you remember where you went? 

SG: Yeah. The first time I went out in public I put on a dress and I went to the movie theater and I was so nervous I came home and and uh, got sick.

AS: Oh you got physically ill? 

SG: I got physically ill because uh, that's how much stress it caused me to, you know, come out in public and wondering what would, would I be arrested, would I be beat up? 

AS: And Vickie, when you, did you feel like when Sissy was deciding to, to change the way he dressed when he left the house, that it was a choice that was harming you?

VG: Yes. I mean, at at, to begin with, I, I felt like it was a choice. And I, you know, people did shame him then and I was with him and you know, some people were making assumptions about me and my sexuality, and, um. On the other hand, I had been spending years because Sissy had had—and still sometimes has, but does much better—had very low self esteem. He didn't think of himself as a very good person. That's back in the day of, you know, positive thinking. So I'm putting signs around on his mirror saying, "I'm a good person," and I'd make him get up every morning and say, "I'm a good person."

AS: Would you say it? 

SG: Yes. I would. It would bring tears to my eyes because I didn't believe it. It was was one of the most difficult things I ever had to do.

VG: And while I'm doing all this stuff, then I'm contradicting what, because you know, I'm saying, I'm ashamed of you. Dress differently. 

AS: So this was happening at the same time? You were

VG: Right.

AS: encouraging him to say I'm a good person in the mirror

VG: Right and - 

AS: And then you were saying I don't really want to go out with you if you're dressed like that.

VG: Right. And so I, you know, I had a really challenging time. I, it was hard, very difficult.

SG: That was probably the roughest time in our marriage when I came out publicly. Vickie was embarrassed to be seen with me. Uh, I would go for walks and our daughter, our youngest daughter would uh go for walks with me, but I felt isolated.

VG: I - I didn't, I didn't really understand it and I didn't understand why he couldn't, you know, just, act normal. 

Coming up, Sissy and Vickie talk about how they got through that rough time in their marriage, and the ways that the public perception of Sissy has… and hasn’t... changed over the years. 

SG: I'm always situationally aware. I used to like to go out and have a beer and read a book. Uh I don't anymore because uh alcohol and a guy in a skirt and a blouse just doesn't mix very well. 

—

We’ve been thinking about money stress here at the show.

My 3-year-old daughter just started preschool. My younger kid is 8 months old, and we are entering our first school year of paying double child care. 

And it’s causing me major money anxiety.

Another person feeling some anxiety around money in an entirely different way is a listener named Brandi. She’s 28 and lives in Chicago, and this past week she sent us a voice memo about getting laid off a few months ago from Uber.

BRANDI: And with that has come a lot of change and quite a lot of weird feelings around money.

Because, the thing is, even though Brandi lost her job, she’s got more money than she had when she was working. She’s getting severance and has Uber stock vesting in November. Plus:

BRANDI: My husband’s getting an inheritance from his grandmother and that’s so bittersweet because we loved her to death. But then you get this chunk of money that’s really helpful and is going to help us pay for this wedding we just had that we probably had no business planning. So for the first time in our life we are on the receiving end of these financial windfalls, and there’s this sense of like guilt that comes with that, and a lot of awkwardness? 

I know Brandi and I aren’t the only ones trying to sort through this—the dollars and cents of money, along with all the emotions wrapped up in it. So we want to hear from you if you’re in a moment of money transition. Maybe something is changing in your life and you’ve got a big financial decision coming up, or maybe, like Brandi, something just...happened. Tell us what’s going on. Send a voice memo to deathsexmoney@wnyc.org.

On the next episode: E. Jean Carroll. Two months ago, she published her account of being sexually assaulted in the 1990s by the now-President of the United States. We talk about why for so many years she didn’t want to talk about that, or other instances of abuse.

E. JEAN CARROLL: My philosophy is—Anna you're gonna run me out of this booth, I swear to God—I think many times that talking makes things sadder because you start to uh tell things which makes you sadder, which makes you suffer and I like my way, which is I don't think about it, therefore I'm happy.

— 

This is Death, Sex & Money, from WNYC. I’m Anna Sale. 

While Sissy Goodwin was coming out and beginning to cross-dress publicly, he started a new job at a power plant in Wyoming. 

SG: I progressed from a helper shoveling coal my first day and when I retired, I was a corporate trainer.

AS: And - and so, so it's the early '70s. What were you wearing to work at that time? 

SG: Well, because of the environment at work, I couldn't wear skirts to work because of the moving equipment. But I wore lady slacks and peasant blouses.

AS: Was that an issue with your coworkers or your boss? 

SG: It depended on the boss. The plant manager tried to fire me but the human resources manager says no, I had such a good work record that they couldn't fire me. 

AS: And was that surprising to you that, that you had advocates? 

SG: It was surprising, but I knew I was a good employee and I knew I was uh uh, a excellent operator. I had to be because I was under a microscope. 

AS: When have you felt like your physical safety has been at risk?

SG: Whenever my nose hits somebody else's fist. Ah.

AS: That's a joke? Has that, has that happened a lot? 

SG: It has. Uh, I've been physically assaulted a number of times. These teeth, you see they're nice teeth, I have, those are are implants and bridges because I've had my teeth kicked in. I've been assaulted numerous times. I was sucker punched at the Kansas City airport waiting for my baggage at a carousel. Somebody just roundhoused me and split my ear open. Uh -

VG: He was beat up in Salt Lake, um, one of the people that were beating on him stopped everybody or he may have been killed. 

SG: Yeah, there were six people that jumped me in Salt Lake City. 

Anna: Six men?

SG: Yes.

AS: And what were the circumstances of that? 

SG: Well, I was down there on uh a meeting with PacifiCorp and these young men came out of a pizza parlor, and uh, they called me a name and I just said just leave me alone. And this one fellow says, I'll leave you alone alright. And they started punching me and they grabbed my hair, threw me to the ground and started kicking me. Kicked me in the eye here. I had a detached retina for awhile. 

AS: How long ago was that? 

SG: That was, 15, 16 years ago. Uh, last time I was assaulted was probably six or seven years ago right over here, I used to run the water system out here. I was a water operator and a fellow lived across the street from the water system. He assaulted me and, uh, it just came out of nowhere.

AS: And this is a neighbor? This is somebody who lives not far from you?

SG: Right. Yeah. 

AS: And you were about 65 years old when this happened?

SG: Uh, probably. Mmhm.

AS: When people have attacked you, when other people have decided that they need to hurt you, what do you think is going on? 

SG: I think what's going on there, the dynamics of the people who choose to assault me is that they lack self esteem in their life. And maybe I'm a threat to ‘em in some way, because if you're really secure in your masculinity, a man in a skirt or or a dress wouldn't be a threat to you. It's only if you're insecure in your masculinity that somebody like myself would be deemed a threat.

Sissy has also been arrested several times for the way he dresses.

SG: The charges were disturbing the peace, but in actuality it was because I was wearing a skirt and a blouse. 

Through it all—the job turmoil, the violence, the stares and insults—Vickie stayed with Sissy. 

VG: It took me a while to get past the, what do I care what they think? They aren’t important people to me, but it it took awhile to get there. 

AS: Was there a a time when you decided, uh, I'm in it, I'm in this marriage. I'm not, I'm not going to have one foot out the door, or was it a a process?

VG: Um, you know, one of the things I guess, I always knew I could leave. I mean, I've got a degree, I got marketable skills. I'm, I always knew, and maybe this is what made it possible for me to stay. I always knew that I could make it on my own. I also knew that this is where I wanted to be, with this person. I mean at one point we considered splitting up, you know uh and I don't know, that went on for about a week. [Laughs]

AS: It didn't last very long?

VG: It didn't last very long 'cause you know we couldn't decide who got the water bed. No. [Laughs]

AS: The water bed saved the marriage. [Laughs]

VG: The water bad saved the marriage. No, I mean we, it was just that we're sitting there trying to figure all this out and realizing that that's not what we want to do. And at that point I, you know, did some serious thinking and, and I did some counseling with, I actually went to talk to the kids’ counselor at school.

AS: Hm.

VG: And one of the things that I think really helped me was when he said, Vickie, you know, one of the things that you should feel really good about is that this is out in the open. Your kids are dealing with this in the open. I'm working with children who are dealing with things at home that are, they can, you know, are private, you know, abuse and alcoholism and the kinds of things that are tearing these kids up because they can't talk about it, you know, and our kids, I was encouraging them to go in and talk to the counselors and, and so we worked through it. Because there was nobody for me who had any kind of, you know, it was just, I guess Sissy and I were kind of out here in the Wyoming wilderness figuring this out together and I'm really glad we did. 

SG: Well, I'm glad we figured it out too. It was at that time when I was coming out and we were going through all this turmoil, I didn't know what I was. I didn't know if I was gay. I didn't know if I was transsexual, didn't know if I was a bi-sexual. Matter of fact, I didn't even know what those terms were at the time. Uh so there was a lot of questions for me and for us that we had to work through together. 

AS: Did it change the way you all relate to each other physically in your physical intimacy, your physical comfort with one another? 

SG: I don't know if it's affected our intimate relationship or not. Uh, in that regard we’re uh probably a typical heterosexual couple and we always have been and that hasn't changed, do - do you think so?

VG: I don't think it's, I don't think that's changed any of that. 

AS: Mmhm. And Vickie, when the counselor said to you, at least your kids are dealing with this out in the open, on the one hand I understand that, on the other hand it's a lot for little kids to try to understand. Like they're they’re they're they’re learning about the world and they're understanding this, the public reaction to their family and their father and um, did you as a mother sometimes feel like, I'm not sure this is good for my kids?

VG: Yes, yes. I think, I think there were times when I really worried about them. But at some point, and I can't exactly tell you when, but at some point it becomes clear that there is no normal. And I figured that my kids were going to have to learn to deal with that and I think for the most part, um, they did well. 

SG: Yeah. I carry tremendous guilt with me even to this day of the impact it had on our children here in Douglas uh to have a father who dressed the way I do and the peer pressure on the kids must've been tremendous. Uh, one thing Vickie told me uh when I was voicing my concerns about the children and the peer pressures and what they were dealing with in school was uh, she told me she says honey, uh, kids are pretty resilient and they can survive almost anything if they’re loved. And our children were loved.

Both their kids now live out of state, and after Sissy retired four years ago, he and Vickie decided to leave Douglas too. They moved to Washington State, not far from Portland, Oregon. 

SG: But I found out rural Washington was as conservative or more conservative than rural Wyoming is.

AS: Mmhm.

SG: And I miscalculated what I really had here. I have a small group of friends but they’re loyal friends, and so after we moved up there, I terribly missed the friends I had in Douglas. 

AS: And Vickie, how did you feel about coming home? 

VG: I felt really good about it. It's that rubber band I told you about. We have to come back because this is where we belong. And I guess that's it.  

AS: Do you have any friends, whether locally or wherever, who identify as along the spectrum of gender nonconforming or having a different gender identity than what's considered the mainstream in in Douglas, Wyoming? 

SG: I've had acquaintances come up to me in Douglas and say, you know, I, secretly crossdress. Please don't tell anybody. Uh, so I've had a number of people like that come out and confide in me. But no, I don't have any friends that would be - transcend any traditional gender stereotypes here in Douglas. Although, our oldest son is transgender, uh, male to female. So I - I should say our oldest daughter is transgender. 

AS: How did your child tell you that they were trans? 

SG: Gosh, I don't remember when he, or she first told me. See, I still have trouble with the pronouns. 

AS: Uh huh.

VG: Um, it it's been, it's been a number of years, but I ask her when she actually knew or felt that she was transgender and she, as I recall, she told me it was around the time that she was 28 or so. Um, however, I know that she crossdressed prior to that, you know, um, the way she told me, which then I told Sissy, was she was drunk on the phone calling me and telling me that, you know, that she had this big secret that she had to share. So -

AS: Was it in anguish or in sort of celebration? 

VG: It was in, well, I think she was - even - she was afraid. I - I mean, uh, that's why she had to get drunk to tell me. And I, that kind of breaks my heart 'cause you know, I was sad that, that she was, had fear, you know, because I always thought we were more, or that she knew that we were accepting and that we would love her no matter what. 

AS: And she told you before she told Sissy?

VG: Yes. Yes.

AS: Do you all find that surprising?

VG: No.

SG: No. I, uh, it's been a little difficult for me that she is transgender and it shouldn't be with my lifestyle and what I've been through. But you have this baby boy and uh grows up and uh, in high school he’s three varsity letters. He was very popular in high school. Kind of kid I hated when I was in high school, uh, and then to discover she's transgender, it's it's been a little difficult for me, but I love her and I accept her and wish her the best of course. 

VG: She’s gonna have some - I mean, it's a rough road, but it's always a rough road. So, um, but she's uh, she's our daughter and I love her the way she is.

That’s Vickie and Sissy Goodwin. You can see a picture of them together in their home on our website at deathsexmoney.org, and there’s a picture of the world’s largest jackalope there too. 

Death, Sex & Money is a listener-supported production of WNYC Studios in New York. I’m based at the studios of the investigative podcast Reveal in Emeryville, California. Our team includes Katie Bishop, Anabel Bacon, Xandra Ellin, Emily Botein, and Andrew Dunn.

The Reverend John Delore and Steve Lewis wrote our theme music. Thanks to Carol Bell for her help on this episode. 

I’m on Twitter @annasale, the show is @deathsexmoney on Twitter, Instagram and Facebook. 

On the day we met, Sissy was wearing a floral top with a short striped skirt. In other words, his outfit really did not match. 

SG: You can see I'm pretty tacky. My elderly neighbor next door, she used to make me clothes. And she was always critical of me because I didn't match, so she’d make me a skirt and a blouse set, and she says, Sissy when you wear this skirt, you have to wear this blouse. And uh she’d actually get angry with me if I didn’t - didn't match.

I’m Anna Sale, and this is Death, Sex & Money from WNYC. 

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