Curi – YAAS Convo with Madi Q&A!

Episodes 112 and 113 featured Madi, a crossdresser from Portland who came on the podcast to share her story. Here’s our Q&A with her.

How old are you and where are you from?

I’m 40. I grew up in Santa Cruz, California and moved to Portland, Oregon at the end of 2015.

What brings you to the podcast?


Through another member of the community and guest on the show, Hope. We’ve known each other for several years, and she said some *very* kind words about me in her interview episode. That got me interested in checking out the Discord group, and one thing led to another.

Are you a crossdresser?

Yes.

How do you feel about the term crossdresser?

I don’t love it. I increasingly feel that it just describes an activity and not an identity. It doesn’t communicate anything about your relationship to gender or your motivations. That and it just doesn’t have any positive associations—it’s not a word people associate with craft or personal enrichment.

How would you identify with your gender identity? Do you identify as transgender? Why or why not?

I identify as genderqueer, which does put me under the transgender umbrella. The way I see it and feel it is that my whole self can’t be contained by one gender expression. I don’t feel a lot of need to claim transgender personally, though. It’s replaced “transexual” so thoroughly that I feel like using it to describe myself would probably cause more confusion than it would resolve.

How would you classify your sexuality? How did you discover that?


It depends on who I’m talking to and how much time we have to talk about it. I’ve generally rounded off to “straight” in the past, for the sake of simplicity, but I think straightness has more wiggle room than the popular discourse usually gives it credit for. 

There was a great opinion piece on the NYT recently urging bisexuals to come out, and it made the argument that it does *not* mean equal attraction to everyone at all times. It can lean more toward one sex than another, and it can be situational, and it can vary over time. I’m not sure I’m ready to claim bisexual yet, but given that argument, I’m warming to it.

All that said, “femmesexual” is the best term I’ve found to describe my orientation. I’m attracted to femininity.


In your Curi – YAAS conversation with Giselle, you talk about wanting to come out at work? Have you done that yet? What was the work reaction like?

Yes, I came out the next week, and it was a phenomenal experience. My team was incredibly supportive, and I felt a huge weight lifted from my shoulders that I’d grown so used to that I barely realized it was there. When you’re closeted, there’s a kind of paranoia that sets in around whether you’re doing anything that will out you. Was that gesture too femme? Was that drag race reference suspicious? Is my birthday tiara visible in the background of this zoom call? (it was, and for months, and no one ever noticed). I’ve been able to let go of all of those worries, and it’s been such a liberating feeling. If it’s safe for you to come out, I encourage it.

You also discussed with Giselle, about your affinity towards Drag? What is your fascination with it? 

Fundamentally it’s the same fascination with transformation I have for any kind of gender nonconformance. But I like the hugeness of it. I love camp. I love the way it queers femininity, turning into a loud, commanding, powerful force. Drag queens are gonna save the world.

Why should I watch RuPaul’s Drag Race? Is it really that good of a show?

It can be. Honestly my enthusiasm for it has been cooling off lately, but I do think it’s a great show overall. I’ve learned a lot about confidence and authenticity from it.

You talk about avoiding the spotlight when you talked with Giselle. How important is passing to you? In what ways do you try or not try to pass?

I’d probably be lying if I said I didn’t do my best to pass, but I don’t *expect* to pass. I want to create the best illusion that I can. I pay a lot of attention things to proportions, what kinds of clothes best fit my body, how I move and walk. I don’t bother trying to change my voice though—maybe it’s from watching so much drag race, but doing a voice just seems unnecessary, for me.

What would you say your style is? How did you develop it?

I have a few. Last Fall I was getting into this quasi-1950’s retro look, but I’m not feeling that as much lately. More recently I’ve been into this sort of *Real Housewives* MILF rich bitch vibe.


I’m not sure how to answer the question of how I develop any looks though. I mostly fly on intuition, I guess. I do a lot of online window shopping and play around with outfit composition in my head while I do that.

What’s your favorite thing to wear?


Lately, sequins. I love the sparkle, it makes me feel gorgeous and confident. I have these faux leather leggings I can’t get enough of, too. Oh and heels—they’re an important part of the transformation for me, in the way they change how I move.

What do you wish you did differently in your life? Do you have any regrets?

It probably goes without saying I wish I’d dressed more when I was in my 20’s and early 30’s. I try not to get too caught up in that though. 

What advice would you give to other crossdressers/transgender individuals?


If it’s safe for you to come out, start coming out. You need the support. This part of you is fundamental to who you are, and keeping that a secret will wreck you.

Would you recommend others to come onto the podcast? Why or why not?

Yeah if listening to the show makes you think, “hey, that seems like it would be fun,” then definitely reach out to Giselle and come tell us your story!

Curi – YAAS Convo with Hope Q&A!

In episodes 103 and 104, Hope from Tennessee comes on the podcast to tell her story. Here’s our Q&A with her.

How old are you and where are you from?

I am 53 years old and I am originally from Tennessee.

What brings you to the podcast?

Giselle and I met years ago when she started the podcast, and I’ve followed along the entire way. I figured it was time I was on as a guest.

Are you a crossdresser?

Technically yes, but I do not use that term to describe myself often.

Are you open about your crossdressing/sexuality/gender? What was that coming out process like? Do you wish you could tell more people?

I am open to anyone who can understand and stay positive about it. I do not flaunt it, but I don’t hide from it either. 

Were you surprised about the reactions you got in coming out to people?

It’s been a mixed bag for me. For a long time I had no problem telling anyone. I found out in some cases it’s just easier and/or better not to bring it up.

Do you identify as transgender? Why or why not? 

I do personally identify that way. I know that the way I feel about gender and myself and how I present, that it falls under the definition of being transgender.

Have you ever thought of transitioning? Either medically transitioning or socially transitioning?

Yes. I actually consider myself in transition. Because, as we know, everyone’s journey is different. I will likely never take HRT, so the things I do now with diet, exercise and grooming all contribute to the way I present in both male and female roles. 

How would you classify your sexuality?

I consider myself straight.

How important is passing to you?

Passing is important to me as far as blending in when in public. I prefer to go out and not be noticed. So, that is the focus of my transformation.

What have you done to enhance your female persona?

As stated before, I’ve done a lot of training in attempt to build my body to be more femme in shape. It’s not the same as HRT, but it has served me well over the years and I’m proud of what I have accomplished in that way.

What would you say your style is? How did you develop it?

What I prefer is BoHo or vintage style clothing. I could do a better job of developing that look. It something I always work towards. 

What’s your favorite thing to wear?

I have to say jeans and boots with a flowing top.

What do you wish you did differently in your life? Do you have any regrets?

I do not live with regrets, I have none.

What advice would you give to other crossdressers/transgender people?

Find your community! There are many outlets for support, but it does take work to find the one that fits you best. Many of us share the same feeling and fears, but you have to look hard to find those with a common ground.

Would you recommend others to come on the podcast? Why or why not?

I have recommended at least one guest already! And I know several others that would be a good show!

Curi – YAAS Convo with Kelly Mason Q&A!

In episode 89 and 91, Kelly Mason, a crossdresser from Michigan shares her crossdressing story with the podcast. Here’s a little Q&A we did with her.

How old are you and where you from?

35 turning 36 in a few weeks. I’m from Grand Rapids, Michigan

What brings you to the podcast?

I love what are you doing with the podcast and the space you’ve created. And I love to talk, especially about myself! Lol

Are you a crossdresser?

I am!

Do you identify as transgender? Why or why not?

I do see myself as transgender. It is an umbrella term in my eyes. Getting more specific, I usually say bi-gender as I feel that describes my experiencing life as both male and female.

Did you ever have thoughts on transitioning? What made you decide to transition or not transition?

I certainly do. The primary factor in me not transitioning up to this point is that I would miss my male existence. I’ve never been unhappy with who I am, just desired to make more of myself known to the world. It’s not something I’ve ruled out, the future is unknown and that’s okay. Being raised in such a socially gendered society, it’s easy to think I must be male or female and not give acknowledgment to the possibility of both. 

How would you classify your sexuality?

Bisexual. I am primarily attracted to females and trans females. But I do find the random guy here and there turning me on.

Have you explored your sexuality? Was that challenging?

I have a little bit. I’ve been with a guy a couple times. It was hard to push myself into the water if you will. It’s even helped me get a better understanding of what I like in my hetero experiences.

Are you open about your crossdressing/sexuality/gender?

I am open to two people in my life, my ex-wife and current girlfriend. I’ve started to socially connect with some others in my area through Bumble BFF as a woman. Outside of that, my entire world knows my male existence.

Do you wish you were more open about your crossdressing to others?

I do wish it was easier to be open about it. Ultimately, I respect the relationships I’ve developed with people and understand the impact it could have. Just as my experience as Kelly is important, so are those relationships. So it may happen someday, but it will be a very well thought out decision.

Do you wish you came out sooner as Kelly?

Even though I haven’t as of yet, I do wish I came out younger. Just because I realize now that the book of me is constantly getting longer, and the longer it gets, the more of a “surprise” it will or would be.

Are you in a relationship? Does your partner know? 

I am. And she does.

You talk about taking girl staycations in your interview with Giselle, why did you decide to do that?

So my stay-cation/girl-cations have been super important to me. In both cases it allowed me to essentially have a barrier free experience as Kelly. Like from wake up to bed time, which was a huge step from getting a “couple hours” in the bedroom.

How important is passing to you?

Too important lol. It is though. If I like how I look…male or female… I am happier. 

What would you say your style is? How did you develop it?

Oh gosh… I’m all about cuteness. So I’m not so much into short dresses and crop tops (everyone should be thankful for the latter), I love a jeans and cute top look, leggings for days, I have so many pairs of flats.

What’s your favorite thing to wear?

My absolute favorite is rocking a cute dress with a cardigan, I can go heels or flats with it…but ugghhhh I also love black leggings and a Jean jacket with some white canvas shoes…I can never decide.

What do you wish you did differently in your life?

Taken this head on sooner. I have been curious forever and only in the last 7-8 years allowed myself to truly discover this.

What advice would you give to other crossdressers?

Be honest. To yourself and those close to you. When I first confronted this and was married, I tried to play it off so many times. And the most pain I inflicted was just not being as honest as I could’ve been. 

Would you recommend others to come on the podcast? Why or why not?

Absolutely! It was such a fun chat and experience. And we need more exposure to normalize this. I want to hear all of your stories!

Curi-YAAS Convo with Barbara Kay Q&A!

Episode 77 features Barbara Kay, a crossdresser who lives with her family in Arizona. Here’s our little Q&A with her.

How old are you and where you from?

I am 47, from Phoenix, AZ

How long have you crossdressed?

I have been dressing most of my life, earliest memories were around 4 or 5, and I have been dressing in some form or another every since…

Are you heterosexual? Bisexual? Unsure?

Earlier on, I identified as Bi, but I am married and considered myself as flexible and openly attracted to a more feminine form…

How important is passing to you?

I’ve never cared about passing as I am more about being presentable. I like to make sure I am well kept and well dressed when I present as Barbara

What would you like to do with your crossdressing moving forward?

I just want to connect with others, be there for any form of support…

Are you public about your crossdressing?

Yes, in that I am comfortable going out anywhere when dressed as Barbara

What’s your favorite thing to wear? What would you say your style is?

I like to dress for the occasion so, if it calls for dressing up for an event/outing, i like to wear things trendy/stylish for my age….my style is more age appropriate, I like to look like women who I admire such as Janet Mock, Wendy Williams, Vanessa Williams

What do you wish you did differently in your life?

Wish I had the understanding I have now, when I was much younger, and be able to just be just as carefree with being Barbara as I am today

What advice would you give to other crossdressers or those questioning their gender or sex?

Truly understand who you are with your dressing/gender/sex, and be comfortable being you…

Why did you come on the podcast? [Would you recommend others to come on the podcast?]

Just wanted the opportunity to connect with you as I have heard how great you are and how fun your podcast was to do….absolutely I would tell others to come and share their stories with you, its a great forum/outlet for others to see others are out here just like me!

Curi-YAAS Convo with Veronica Q&A!

Episode 72 and 74 featured Veronica, a crossdresser living in Seattle

How old are you and where you from?

 48 going on 28, I was born in Helsinki, brought up in Vancouver, BC, spent 10 years on the east coast and then I’ve lived in Seattle since then

How long have you crossdressed?

Since I was about 8, I think

Are you heterosexual? Bisexual? Unsure?

I could be labeled as on the straight side.  I am sexually attracted to the female form.

Are you currently in a relationship?

Yes, married with two kids, 7 & 9

How important is passing to you?

I like to be perceived as a woman rather than a man dressed as a woman.  I won’t change my voice because it is just too much work to do that but if I fool somebody to the point of thinking that I’m a woman until I speak, I’ve done well!

What would you like to do with your crossdressing moving forward?

I would like to keep getting more open about it by baby steps. My extended family might end up finding out and that might be a relief for me… and maybe even them.

Are you public about your crossdressing?

Yes, except for my extended family.  Not so public that I would post my VeronicaLove5000 to my own facebook.

What’s your favorite thing to wear? What would you say your style is?

I love legwear like pantyhose and tights.  I would say classic and pretty.  I love fit and flare dresses and 1950s style.

What do you wish you did differently in your life?

Possibly starting public crossdressing much earlier in life.  It would have been great to have styled my natural blonde hair rather than wearing wigs.  Too late for that now… haha!

What advice would you give to other crossdressers or those questioning 
their gender or sex?

First thing is that repressing it will end up being as successful in your mind as prohibition was in USA.  Second is that coming out, generally, is much worse in your mind than it is in real life.  Lastly, talk to people in the community that you identify with.

Why did you come on the podcast? [Would you recommend others to come 
on the podcast?]

I heard the podcast and immediately it felt like a breath of fresh air for crossdressers.  I wanted to talk to Giselle pretty immediately and, true to her word, she responded immediately and got me on the podcast at lightning speed. I friend of mine already wants to come on the podcast.