Tag: crossdressingpodcast

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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!

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Curi – YAAS Convo with Candice C. Q&A!

In Episode 110, Candice C, a 39-year-old crossdresser comes onto the podcast to tell her story. Here’s our Q&A with her.

How old are you and where are you from?

I am 39 and from Canada.  Yes it’s a big country, but I have lived all over the place, so let’s just leave it at Canada 🙂

What brings you to the podcast?

I found the podcast through my own desire for consuming resources in the search of defining my self identity.  Most of the resources out there are outdated.  I love the fresh approach that this podcast is taking!  I decided to contribute in order to share my story and add to the growing number of voices out there.  Hearing other voices is helping me, and I hope that I can help others!

For newcomers to the podcast, is the CrossYAAS podcast worth listening to? Why or why not?

The podcast is definitely worth listening to.  Giselle weaves interesting current affairs with topics of sexuality and gender.  And the interviews serve as a glimpse into the lives of other people that also cross dress or otherwise explore gender.

Are you yourself a crossdresser?

Yes!

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

I don’t like to slot myself into one identity.  I find that somewhat constricting when it comes to sexuality and gender.  But I can relate to non-binary and genderfluid.  And I like to consider those under the trans umbrella.

How would you classify your sexuality?

I would classify myself as having a submissive feminine sexual identity, and attracted to dominant feminine energy.  

Are you open about your crossdressing/sexuality/gender?What was that coming out process like?

I am only out to my wife IRL.  That process, as you can or will hear in the podcast, was not ideal.  It came out with her discovering pictures on my computer.  That started off the conversation in a really negative way as it damaged a lot of trust between us.  If I had told her earlier on in our relationship, things would have worked out a lot better.  She is very open minded and accepting of LGBTQ and various sexual kinks.  

In your Curi – YAAS conversation with Giselle, you talk about not being open about your crossdressing to your workmates because they’re older and they wouldn’t understand. Where do you think your perception of them not understanding stems from? Would it change the work dynamic if they knew about Candice?

I work in a small company of about 20 people.  Many of whom I have known for about 10-15 years, and the others are quite a bit younger.  Therefore I think they would get over it and accept me because they have known me for so long.  However, I work as a consultant for various companies.  And I have worked with probably over 200 by now, so I have to deal with new people all of the time.  My industry tends to be an older and more conservative-leaning crowd.  Much of my work involves working in and around small remote communities.  So I feel as though if I were open about this, it would expose me to the judgement (or perceived judgement) of a lot of different people.  And the risk to my career as I transition into a leadership role is a big concern.  Not to mention that my boss of 15 years has shown himself to be a bigoted individual towards people that are LGBTQ.

You also discussed with Giselle the sexual component of crossdressing…would you care to elaborate on that? What about crossdressing gets you turned on?

There are many parts to it that are sexually charged.  For one, its the anticipation of having the chance to dress up.  When it’s something that can’t always be done, it adds a certain element of built-up energy.  It’s like a seed that just starts to grow.  I might be inspired by an outfit I see on the street, and I think about how that would look on me.  I look for that outfit online.. thinking about the day that I might actually order it and try it on.  Then when the day comes, and I get dressed up.  I look in the mirror and feel good about what I see.  Not like, “hey I’m hot”, it’s more like, damn I look fine.  As a dude, I rarely every feel sexy.  But when I dress up, I actually FEEL sexy.  It’s an exhilarating feeling to embody the sexual energy, instead of as a man just seeking out the feminine sexual energy.  Then there is the tactile nature of all of the different clothes and how they are tight and often form fitting.

You talk about your children with Giselle and breaking gender binaries down with them. How did you come about that conclusion and what is the significance of that moving forward in your children’s upbringing?

It was an approach that my wife and I had early on when we had our first. (in retrospect this sounds like it would have been a great segue to share about my personal gender identity). We didn’t want to go as far as waiting to gender them until they are old enough to do it themselves.  I think that can be too confusing for people around them.  We have always referred to our son as a boy and our daughter as a girl.  We didn’t find out their gender when my wife was pregnant, so right from the get-go, we set the stage for baby gifts from family and friends needing to be gender-neutral.  We have tried to encourage hobbies, toys and activities that boys or girls like to both of our kids.  And we let them choose what they want to do.  Presently, our boy like most typical boy things, and our girl likes mostly typical girl things.  But they are free to chose what they genuinely like.  We have tried to remove as many gender barriers as possible for them, as I think they will appreciate that gender-norms and practices in the school and workplace can be limitations to their potential.  

Does passing play an importance when you are Candice? In what ways do you try or not try to pass?

I always aim to pass when I dress.  I don’t feel comfortable blending gender presentations. I try to pass with the best makeup as possible, and shaving my face very close.  Luckily I don’t have much body hair to deal with, and I generally don’t shave my legs or arms.  Wigs end up being an essential piece for me.  I don’t use wigs or hip/but enhancements.  I am athletic, so I have a lean body shape and my shoulders aren’t very broad either, so I think that helps.

If you had a style when you’re dressed as Candice, what would you say that is? How did you develop it?

I tend to gravitate towards more glamorous evening wear.  I say yes to sparkles and sequins!  I don’t think I really have a style.  I tend to be fairly eclectic.  Which is to say, I don’t really have very many clothes yet.

Do you have a favorite place to shop?

I used to love ordering from Charlotte Russe.  I loved almost everything from there.  I have filled my cart a few times, but never ordered, from Shein and Boohoo.

What’s your favorite thing to wear and why?

I have always had a thing for pantyhose.  So it’s a must for just about every outfit!  It’s hard to say why, but they just feel amazing to wear.

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

I wish I had explored my gender expression and sexuality more when I was in my early 20’s.  When I was single and still defining myself.  Once you are on a career path with a wife and kids, it becomes a lot harder to do that.  Life gets busy and there is a lot less time for ones self.  I think that is why a lot of crossdressing men come out in their 60’s.  They have retired and their kids have grown up, and they find themselves with the time to look inward and explore those parts about themselves they they tucked away for so long. 

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

Read and listen to as many resources as possible.  There is so much out there now, there is no excuse.  The sooner that you start exploring your identity the better.  If you hide it, you risk damaging a relationship that you may be in like I did.

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

Yes, absolutely.  It is somewhat of a therapeutic experience.  Giselle also asks the tough questions in order to challenge some listeners in some things that may be holding them back.  I may, in the future, refer people to my episode if it makes sense.

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Curi – YAAS Convo with Ryanne aka Trekkie Q&A!

Episode 108, Ryanne also known as Trekkie, comes on the podcast to tell her crossdressing story. Here’s our short little Q&A with her.

How old are you and where are you from?

I am 40 years old. I was born in the United Kingdom, raised in Canada, and have lived in the US since the early 90’s.

What brings you to the podcast?

I was looking for a community of people who are questioning and exploring gender, but not necessarily focused on permanently changing their bodies or identities.

Are you a crossdresser?

Yes!

What makes you different from other types of crossdressers?

I also enjoy wearing diapers occasionally. Sometimes I just like the feeling of the padding. Sometimes wearing one turns me on. Sometimes wetting and wearing a wet diaper feels good.

How has living in the midwest affected your lifestyle as a crossdresser?

I had remained closer to the friends and family who knew me and accepted me when I was younger, I may have felt more comfortable openly experimenting with gender earlier in life. The midwest is obviously a conservative place, and challenging gender norms is intimidating. It’s a lot easier to keep my head down and go with the status-quo out here.

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

I had not considered myself transgender, until I was challenged by my therapist and the CrossYaas podcast last spring. I suppose the term that fits me best is genderqueer, which is under the transgender umbrella. I don’t feel comfortable using the general term trangender, because it requires so much explaining to land at how I actually feel. I feel somewhere in-between a man and a woman, and it fluctuates!

How would you classify your sexuality?

I am sexually attracted to most, if not all things feminine. I am attracted to women, but it is a confusing attraction. I often want to feel what it’s like to be a woman, and be with a woman at the same time. When I was in high school, I did joke to my girlfriend that sometimes I felt like a lesbian. I felt so much shame just admitting that, that I pushed it aside for a long time.

Are you open about your crossdressing/sexuality/gender? What was that coming out process like?

I am open to a small number of friends and family. The experience of coming out to each person has been vastly different. With my wife, the conversations are ongoing. With people like my aunt and brother, the conversations were quite easy.

In your Curi – YAAS conversation with Giselle, you talk about going out in public crossdressed with your wife. How was that experience for you? How did you get your wife to agree to that? Where’d you gain that confidence from?

It was so much fun! I think the part I enjoyed the most was letting go of all my stress and anxieties. When I’m crossdressing, I don’t feel like myself. I feel like I’ve shed all of the pressures and responsibilities of being the “Man” of the house, and I get to truly have fun! When I was out with my wife I felt vulnerable. I felt cute. I felt loved. And I loved seeing how protective she got. When someone gave us the stink-eye for holding hands, she nearly charged at him!

I didn’t get my wife to agree to go out with me. She agreed all on her own. I just said it was something I would like to try. I asked her to think about it and get back to me. I also suggested I split our time between girl mode and boy mode, so she could still fall asleep next to the husband she knows. I think that compromise was key to our first experience together.

You also discussed with Giselle going to CapCon with your wife, an ageplay convention in Chicago. Can you elaborate more on that? The CrossYAAS listener would love more details.  Would you go back?

I absolutely would go back! It was the most loving and accepting place I have ever been. The people were so friendly and having so much fun. And their clothes were so cute! Lots of people play with gender when they ageplay, so it was really the first time I had been exposed to a real-life group of crossdressers. And I’d be happy to share more details in the future!

You talk about your children with Giselle. How have you approached the crossdressing aspect of your life with them, and if you haven’t, what would be an ideal way for you to do that?

I have been making incremental changes to my wardrobe for almost two years. I started growing out my hair. When it got long enough to get in my eyes, I started borrowing my daughter’s sparkly cat ear headbands. The kids loved it and encouraged it. I think the next thing I did was wear a midriff long-sleeve T-shirt with a neon drawing of the space shuttle on it. They stared long and hard at my exposed belly button, before shrugging it off. When I asked my daughter how she felt, she said she was confused at first, but then wondered why she was confused. She said she realized she likes my shirt and it didn’t matter that it was shorter than my other shirts. She thought it was cute. 

I’m not quite ready to strap on my fake titties and pull up a mini-skirt around them, but I do dress more feminine in daily life. They are now used to seeing me in “girl clothes” and wearing my hair in expressive ways. I have had my nails done, and I’ve worn mascara around them. My eldest daughter also knows my locked office closet is full of dress-up clothes, but I’m not opening it up for her any time soon! My middle child has asked if we could play dress-up together, but we haven’t made it happen yet. I’m excited to see what develops!

How important is passing to you? In what ways do you try or not try to pass?

I have two crossdressing modes, more or less. In the first mode, I am not trying to pass at all. I may or may not have a beard, and I’m wearing a mixture of things found in the men’s and women’s section. I feel this is me at my purest level, just having fun with who I am and what I can wear to make myself feel good. This is how I currently dress around my family. It probably doesn’t count as crossdressing, but it feels good!

In the second mode, I want a divorce from myself to become something else. In this case I am trying to pass, but it’s still mostly for me. I want to feel the makeup on my face, to remind me not to touch it. I want to feel the eyelash extensions tickle my cheek. I want my shoes to change the way I walk. I want to feel the shaper compressing me into an hourglass and the silicone boobies jiggle when I move. In those moments I want to be completely lost in femininity. If I pass, great! It only helps me get lost even more.

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

My style is quite juvenile, and I doubt that will change. My least favorite phrase in the English language is “That’s inappropriate”! I like bold colors in simple combinations. I like silhouettes that are shapely and feminine. I like fabrics that feel soft and light against my skin. I like ribbons and bows in my curly hair. Some may call me a Sissy, and in some ways that’s a decent fit. But I never feel humiliated by my feminine side. I want to feel empowered by it.

What’s your favorite thing to wear?

I start with a soft, thick diaper. Not a crappy drug-store brand geriatric bladder control device. A purpose-made adult sized baby diaper from a boutique manufacturer like Adult Baby Universe or Rearz. A tennis or skater skirt with wedge Chuck-Taylor style shoes. A pink midriff top. A choker and dangly earrings (I want to get my ears pierced this summer!!!) And my hair in pigtails.

What do you wish you did differently in your life?

I wish I hadn’t dismissed my questions so many times. I wish I had continued to look inside to embrace what was important to me, rather than looking to others to give me fulfillment.

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

Keep asking the questions, and find people who are asking the same questions. If you know there are others out there, hopefully you’ll know you are valued.

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

Yes! But wait until you are ready. For me, I needed ice-breaker first. I was very nervous to record, and didn’t feel prepared. Giselle was great at calming my nerves, but I still felt like I was babbling incoherently!

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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!

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Curi – YAAS Convo with Amanda Q&A!

In Episode 95, Amanda comes on the podcast to tell her unique crossdressing story. Here’s our Q&A with her.

How old are you and where are you from?

39 years old Richmond, Va

What brings you to the podcast?

To better understand myself and to help others to know that they are not alone.

Are you a crossdresser?

I’d say Gender Fluid

When did you first realize you enjoyed crossdressing?

Started crossdressing around 11 years old.

What makes your crossdressing different from the average crossdresser?

My male side is 39 years old, However, my female side is an elderly, disabled, and morbidly obese southern great grandmother. My crossdressing is as a mature elderly lady.  I am different as that I want to be much much older when I crossdress.

Where do you think your love for dressing like Amanda comes from?

I don’t know why I want to be an elderly lady other than it feels right and normal. It is me.

What are some of the biggest misconceptions you want to clarify regarding what it is you do as Amanda?  

While I am not disabled in real life, Amanda is. She is very fat and she uses a walker and wheelchair to get around. I don’t take from others. I can only be myself.

Do you identify as transgender? Why or why not?

If gender fluid is trans(gender), then yes. I am gender fluid and some days I feel male and other days I feel female.

How would you classify your sexuality?

I would say when I am Amanda, I am Straight, but when I am in my male side, I would classify myself as gay. 

Has it been difficult being open about Amanda to potential partners? Why do you think that is?

Yes, it has been difficult. While I will NOT hide who I am, I have told potential partners upfront and that has caused some to run away. Others are okay for a little while and others just want something other than a long term relationship.

How important is passing to you?

It is important but at 6’3 I know that is not really going to happen.

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

I would say my style is 1940’s great grandma. I was drawn to it as I figured out who actually is Amanda. I don’t understand exactly why, but it is what I am most comfortable with.

What’s your favorite thing to wear?

I love a flower print dress

What do you wish you did differently in your life?

I wish I came out as gay and gender fluid earlier.

What advice would you give to other crossdressers?

Be yourself, find your style and embrace it. Be you.  

Advice for other mature crossdressers?

Regardless if you are 29 or 59, if you want to dress as an elderly lady, go for it! Embrace it and make it your own. 

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

YAAS! – To tell your story you are helping others and yourself. We need to share our stories with each other to let one another know we are not alone.  

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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!

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Curi – YAAS Convo with Emma Scarlet Q&A!

In episode 87, Emma Scarlet shares stories of her life and what it’s like living a secret crossdressing life living in Indiana. Here is a quick Q & A we have with her.

How old are you and where are you from?

I’m 45 and from Indiana.

What brings you to the podcast?

A common acquaintance told me about it.

Are you a crossdresser?

Yes I am.

Do you identify as transgender?

I don’t identify as trans, although I have trans elements in my life.

How would you classify your sexuality?

Not sure. Androgynous/non- binary perhaps

Are you open about your crossdressing/sexuality/gender?

I am NOT open or out publicly.  A handful of friends know.

Are you in a relationship? Does your partner know?

I’m married and yes, she knows I crossdress

In the conversation you had with Giselle, you talk about cheating on your wife. What made you do that?

I cheated because I wanted to experience people and sex in different ways.  I did it because I could and yearned to be appreciated and objectified.

How much do you love your wife?

I love her very much

Seriously, why is your wife so amazing?

She doesn’t believe in quitting and her Dad quit on her and her sister and she didn’t want that for our kids.

What would you say is a key to a long lasting healthy marriage?

COMMUNICATION

How important is passing to you?

Passing is very important to me, I am not passable and probably another reason I don’t go out much.

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

My style is still developing.  I love cute skirts and camisole’s.  I love a little black dress.

What’s your favorite thing to wear?

My favorite thing to wear is a black cami, an oversized shirt that hangs off my shoulder and a black satin slip.  Pretty much my pj’s.

What do you wish you did differently in your life?

I wish I transitioned at a young age or come out completely and honestly upfront with my now wife early in our relationship.

What advice would you give to other crossdressers?

Be yourself and love yourself, it’s who you are and you are loved.

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

I would highly recommend others come on the podcast.  It’s cathartic to hear your own story and deal with what you’ve done or not done. 

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Curi – YAAS Convo with Jessie G Q&A!

Jessie G, a Canadian crossdresser comes on the podcast to tell her story. Here’s some questions we asked her.

How old are you and where you from?

39, Regina Saskatchewan Canada

In terms of Gender, how do you identify?

Bigender or flexible

In terms of Sexuality, how do you identify?

Straight

With regards to your gender and sexuality, is it difficult living as that where you are?

It can be, depending on the day but pretty good on the whole

Do you consider yourself a crossdresser? Why or why not? 

Yes, well mostly, well it all gets confusing.  I guess it all depends on ones definition of crossdresser. I’m male and wear women’s clothing, for some I am a crossdresser for others I am beyond.

Do you consider a crossdresser transgender? Why or why not?

Crossdressers in some ways may be considered transgendered. For me I can view transgender as fairly wide spectrum so crossdressers may be a 2 or 3 out of 10 on such a scale. 

How do you present in public? Are you open about your crossdressing?

Sometimes at work and out with friends as I have been much more open about it for just over a year.

Are you in a relationship? Does your partner know about your crossdressing? How was that process for you?

In a 14 year relationship, told her in the first month as it is always better to as later on the likely issue is less about crossdressing and more about the violation of trust. So I gauged some reposes and then just but the bullet which is the best option as she has been very supportive

How important is passing to you?

Since I’m 6’3, and I weigh 220 lbs, passing is out the window so I just try to look nice

Do you have a distinct sense of style? How did you develop it?

Less a distinct style as more knowing exactly what definitely isn’t. Developing it was basically experimentation

What’s your favorite thing to wear?

Strangely enough, business casual. Who would have thought? Though I am sure it is something about having so many more options than men’s clothing.

Are you in the stage of transitioning? Are you on hormones? If so, can you tell us a little on what made you do that? Was that a difficult decision?

I did start hormones about 6 months ago or so just to see how I liked it and perhaps to get a bit more curves.  I finally decided to do it after a bit of a melt down and re-centering of myself.  And I also realized that I can always stop anytime I want to.

What do you wish you did differently in your life?

Accepted myself earlier, though it wasn’t always a good option. Luckily society is changing faster than I was.

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

Explore. It’s easier to be you than someone else.

What brought you to the podcast?  Would you recommend others to come on the podcast, why or why not? 

Honest truth, lack of any other content for crossdressers. Now what kept me around is the real question, I found it 3 or 4 episodes in and the roughness has definitely been smoothed out as you found your stride. It’s also interesting to find out how many different variations there are in crossdressing.

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Curi – YAAS Convo with Abby, an ABDL Q&A!

Abby, a crossdresser living in Missouri comes on to the podcast to talk about her crossdressing and her fetish for Diaper wearing

How old are you and where you from?

28, I’m from Missouri

How long have you crossdressed?

I’ve been Crossdressing since I was probably five but only recently I’ve started doing public outings.

Are you heterosexual? Bisexual? Unsure?

I consider my Asexual. I am currently dating my Girlfriend(Mommy). We have dated for a year

How important is passing to you?

Passing is somewhat important, but I don’t feel that passing is in the cards for me.

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

Moving foreword I would like to become more confident in my Crossdressing and public outings.

Are you public about your crossdressing?

I am not public about my Crossdressing

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

My favorite thing to wear is cute short dresses or “little” clothes. Think Melanie Martinez style.

What do you wish you did differently in your life?

I wish I was more confident in my different oddities sooner in life and accepted myself sooner

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

The advice I would give about Crossdressing is you have to practice to become better and build confidence. If you are questioning your gender or sex I think you have to research and learn all you can about different genders and sexualities to discover who you are

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

I’m coming on the podcast to share my experiences and knowledge on asexuality and the ABDL kink. And yes, I highly recommend for others to come on the podcast to tell their story.

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Curi – YAAS Convo with Chris D’ Orso Q&A!

Episode 79 features Chris D’ Orso, a crossdresser from New York who comes on the podcast to tell his story and how he’s using his crossdressing to benefit the world!

https://dressember2020.funraise.org/fundraiser/chris-dorso

How old are you and where you from?

I’m 44, and I’m from Rochester, New York.

Are you public about your crossdressing?

I guess wearing a dress every day for a month and posting pictures on Instagram is just about as public as it gets. =)

How important is passing to you?

It’s not. I’m just a guy who’s wearing a dress, because they’re comfortable and fun. (And to raise money for charity.) And if there’s a young person out there who sees me, either in person or on social media, and says “if that guy can do it, then I can be myself too,” then that’s a huge win even if I never raised a single dollar. But at the same time, I’m taking this seriously. I’m wearing appropriate shoes, and tights every day for warmth. I felt like clomping around with hairy legs and sneakers would be making fun of this movement and what it stands for.

How do you identify in terms of gender?

I’m a cisgender hetero male.

Do you consider yourself transgender? Why or why not?

No. I have friends and family members who are transgender; I have enormous love and respect for those who have to deal with the emotions and pressures and stresses, both internal and societal, every day that come with not identifying in the gender you were assigned at birth. At the end of the day, I take this dress off and I can walk through the grocery store in jeans and a concert t-shirt and be completely invisible. Not everyone has that luxury. It goes back to what I said above, though. I’m wearing dresses in the manner they’re intended – with “women’s” shoes and tights every day – because ultimately, they’re just fabric so we’re not walking around Target naked. I will not make light of it by being “a guy in a dress,” even if I’m just a guy in a dress.

What’s the worst thing about being a crossdresser?

Nothing seems to fit quite right! Everything’s either super loose in the chest or super tight on my arms. I find myself WAY more self-conscious about that than I thought I would be.

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

Two weeks in, I think I can actually answer this! I’ve been most comfortable in knee-length dresses that have sleeves. Sweater dresses have been fantastic, because they’re super comfy and you can absolutely wear them all day.

What is Dressember?

I was inspired by a few friends who did Movember, growing mustaches to raise money for cancer last month. I did a little googling to see if there was anything fun like that for December, and stumbled across the Dressember Foundation. The challenge each year is to wear a dress (or a tie, but ties are boring) every day for a month while bringing awareness and raising money for victims of trafficking. I had a few dresses in the closet from previous outings, so I ran the idea past my wife, who was completely supportive. Then I talked with some local friends, who generously gave me nearly two dozen dresses that they were going to donate anyway. I’m going to wash them all and bring them to donate at the end of the month, continuing to pay it forward.

Besides Dressember, what would you like to do with your crossdressing moving forward?

Folks have told me that I’m going to have a hard time going back to pants — but I’ll tell you, it gets cold in Rochester in January. I’m going to be quite happy to wear pants for a while! But I’ve crossdressed for Halloween a few times, and I’d love to do stage drag again because that was quite a rush.

If there’s one thing in your life you could change, what would that be?

I need to get serious about losing some weight. I’m really surprised at how self-conscious I’ve been this month about what I’m eating, actually, because of what I’m wearing. As a result, I’ve lost six pounds.

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

Be as honest with yourself as you can possibly be. I know it’s hard, but please know that there are people out there in the world who can help.

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

When I first did this, I set my fundraising goal for $500. I figured if I could get friends and family to donate a few dollars each, I’d be thrilled. Once I blew past that goal, then $1,000, and then $2,000, I realized that I could actually do much more with a bigger audience. I did a little more googling and found quite a vibrant crossdressing community online that I knew would be supportive of what I’m doing. [And yes, absolutely!]