Monday, October 27, 2025

Father and Son, Both Secret Crossdressers?

 Hello There,

    Today I just had to share one of the most thrilling true life crossdressing stories I've ever read. Father and Son, both secret crossdressers! I am of course referring to Father/Son, or should I say Mother/Daughter duo Jean Rich and Kristin Rivers. Older members of the crossdressing community will undoubtably remember them from their appearance in the LadyLike magazine, or their many appearances at crossdressing conventions. For us younger members of the gender non-conformist community, we may not be aware of them, which is why I just had to highlight their story today!

    The desire to crossdress is extremely unique, and can feel like quite an isolating experience for people. But could you imagine your surprise at finding out a family member is also a crossdresser, let alone your own father?! Well crossdresser Kristin Rivers went through this very discovery and talked all about it, in her self written article in issue 33 of LadyLike Magazine. The article is transcribed below, enjoy reading all about Kristen and Jean's experience discovering that they were both secretly crossdressers!

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There is nothing more complex nor so endearing than the special bond between a father and a son. Indeed, we see these relationships forged in our literature and through modern theatrical productions. Some stories end tragically, others end triumphantly, but all emphasize the unspoken and sometimes mysterious relationship which nobody can deny. So, as it happened one summer day while I was home from college, my life and my father's life would be inextricably bonded in a way which nobody could have ever imagined. 

I grew up in South Florida. My parents were divorced when I was 10. I lived with my mother and my sister while my father was allotted the legal right to see us on weekends. I suppose it was because of this, I had an extra special yearning to want to please him and make him proud of me. I wanted to be like him in so many ways. He was smart, good looking, athletic, a respected professional in our community, very funny, charming with the ladies and a terrific dancer. Growing up in his image was difficult for me. Deep in my heart, I knew I was different than other boys. I had known about my other self as far back as I could remember. I had wanted to be a girl and dress like a girl from the earliest stages of my memory. How could I ever describe these feelings to my father. I knew this would be unacceptable to him. Unacceptable even to a man who proclaimed over and over again how I could tell him anything and be anything and he would love me nonetheless. These are grand words, but clearly some things should be left unsaid. Let's face it, telling your father that you secretly went through your mother's closet and put on her clothes was not what he meant by being able to tell him, "anything." 

Like many transgendered individuals, I had to wrestle with my inner most feelings versus my outer most reality. Running away from home or skipping town after high school to "become a woman" was not an option I saw as possible. My other self would take second place and be buried deep in the recesses of my mind as I embarked on my college career. As it was, I had returned home after my freshman year of college for the summer. For me, this was an opportunity to do something I had only dreamed of while growing up. I would be able to live with my father. Ironically, at the same time I had decided to return home for the summer, my father was hoping to do something he had only dreamed of while he was growing up.

This was to be his summer to experiment. He had an opportunity to find his second self because he and his second wife decided to take time off from each other since they were experiencing difficulties in their marriage. Gaining this freedom, he intended to use the time to shave his body and "dress up" after getting home from work. Clearly, my living with him was going to make this very difficult, if not impossible. 

I was oblivious to the fact that in his joy of having me live with him for the summer, he secretly held contempt in this decision for reasons I would have never imagined. This was to be his summer to be free. To unshackle the bonds of his masculine self and to experience the woman within. Now I was living with him, and the freedom which he had so much desired was stifled once again for fear that I, his son, would never understand. Without me really noticing, he walked around in clothes which covered his shaved legs and his shaved chest. He was unable to set himself free and once again, he became closeted in his own home. It was then, he had made the decision to tell me about himself.

And so it happened, he asked me to come home after work one day and spend some time with him. Time to talk, time to reflect on life and what it was like for him all these years to live with an unspeakable secret. Time to share with his son his deepest and darkest thoughts. Time to lay everything on the line and be prepared to pay the price for freedom. With fear, trepidation and a slight trembling in his voice, he began to tell his tale. He began by speaking in circles but never really getting to the point. Indeed, it took about twenty minutes before he had gathered enough personal strength before finally revealed his secret.

"My first experience that I can remember was to paint my nails when I was 4, but I was ridiculed by the other kids in my building and I knew immediately that this was not the type of thing a little boy does." 

He told me how he always tried to compensate for his feminine feelings during his teenage years. At the age of 1 7, he lifted weights and became the number 2 gymnast in New York City on the parallel bars. He always liked girls and in order to impress them at parties, he learned how to dance. However, despite all of this, he was unable to shed his thoughts of wanting to go to bed at night and, "wake up in the body of Sophia Loren."

Following high school, there was college, then marriage, then graduate school, then one day, an announcement from his wife that she was pregnant. This was when I came into the world. Now the circle was complete. The boy who had so much wanted to be a girl found himself to be a 25 year old married man having to raise a family. Despite his wife "knowing" about his inner most desires to dress as a woman and "feel" like a woman, he held everything inside, trapped and alone. It was just three years later my sister was born.

"Married with two children I did try to handle the feelings deep inside of me and kept myself hidden from my children so that they could think of me as a normal dad."

But this marriage failed, not because of the dressing, but simply because it was not meant to be. It was not too much longer after that my father met the woman who was to become his second wife. Just like my mother, this woman knew of my father's "other self." They had several good years together but in the end, things began to fall apart. The desire to dress had become much to strong for her to deal with despite the fact she said she, "enjoyed" and could accept this side of him. 

I sat and listened to everything he told me. I sat not saying a word. He told me about his fears of being caught while growing up and how on a few occasions he did get caught but always came up with some crazy excuse to justify why he was dressing up. I showed very little emotion while he was telling me his tale. All I did was smile. Later, 1 would find out my non-emotional response and my grin was beginning to anger him. Despite this, he wanted me understand that he was still my father, that these feelings had always been within him but he loved me dearly and this would never change the fact that he was my father and I was his son. 

"We were on the dock in the back of my house. I told my son I was a crossdresser. He smiled at me and I became angry because I was describing to him how difficult my life had been. I did not think this was very funny. This was very hard for me and so I continued to talk about crossdressing and he continued to smile."  

Yes I was smiling. Here I was, sitting, watching, listening to my own father tell me about his life as a crossdresser. At first I thought, "Wait a minute, does he know about me? Is this some crazy way for him to get on my level and talk to me about myself?" Of course this is the normal paranoia common among many transgendered individuals. I thought there was no way this could really be happening, but what if this was true!1 What if my father was just like me, what if I was just like my father and as we all know, the truth is sometimes stranger than fiction.

"Finally," as my father tells the story, "I said to my son I expected him to be more mature about my revelation and asked what he thought was so funny. He looked at me and said everything is okay, he was a crossdresser too! Well, I almost fell off the dock!" We talked for well over 5 hours that night. Later, he would tell me how awful he felt that I would have to go through many of the same difficulties he had experienced or that society would keep me from finding true joy and happiness in my life. In a sense, he felt as if this was his fault in some strange way. I said to him, "Dad, you have given me life. I have my health, I have a good head on my shoulders, I have everything to be thankful for. This is part of my life, it always has been there and it always will be."

Our relationship has never been better. We are father and son, "mother and daughter," and we are best friends. We laugh about stories such as the time my mother had blamed him tor taking a pair of her underwear and he swore over and over again he didn't do it, it must have been the maid. She never believed him and now he knows it was I who got him in trouble. Over the years, my father has participated in many conferences supporting the transgendered community. He has told our story at many colleges, universities and medical schools. We go out together, we both love to dance, and we even have performed on stage together. I am far more open about myself to my friends and my family than my father ever was at my age.

I am thankful he and others like him have led the way for a better world. Understanding the terrible fear he grew up with, I have begun to take on causes I feel passionate about. I am doing everything I can to educate and promote what being transgendered means. I want people to know how we as a community, as individuals and as people can contribute to society and not live in fear of being who and what we are.

Telling a child about your other self is a difficult thing to do. In our case, it was one of the best things that ever happened to us. Some years later, my father took it upon himself to tell my sister. Unfortunately, this did not go over well at all. So what's the lesson to be learned here? 

Take heart and expect the unexpected. Consult professional counselors or therapists to evaluate your personal situation. But most of all, no matter what you do, be happy, be strong, be free and be yourself. In my father's words, "I wish all of you who read this can experience all the joy and good times you can have by being who you are and stop hiding from yourself."  

-Kristen

Check out the photo gallery below to see more picture of both Jean and Kristin:

Kristin Rivers (Son/ Daughter)

Jean Rich (Father/Mother)

Mother and Daughter Together

    Wow, what an unbelievable circumstance for the two of them! I truly can not fathom the joy the two of them got to share as a Mother/Daughter pair, both exploring the world of crossdressing together. I'm sure the support network the two of them built with each other was invaluable, especially given the years of dysphoria the two suffered. I know we all long for a positive relationship like this, so I hope you all enjoyed reading their story as much as I did.

-Carly

Monday, September 29, 2025

The Most Fabulous Airport Crossdresser I've Seen

 Hello There,

    Crossdressing in public is a daunting experience to many, the fear of being outed as a crossdresser is just too much of a risk. However to some crossdressers the absolute joys of being able to present as a woman in public override the fear of being outed. In fact it doesn't even matter to them, the desire to have a feminine experience overrides any fears of being outed, simply getting to be themselves is enough motivation. 

    One such brave crossdresser interested in being free to express herself in public, without fear of public perception is reddit user u/deeevuh (great username), also known as Goddess Lulu. She recently took a plane ride while fully crossdressed, and looked fabulous doing so! Wearing a frilly pink dress with matching pink handbag and suitcase she was sure to be noticed, but she didn't care! Saying in a reddit comment "I used to be so inside myself and robbed myself of really living my best life once upon a time.. these days I try to make up for all the lost time with a massive idgaf attitude, you have one life with free will so make it count". 

    After going through deeevuh's reddit comment's about her experience on the plane, I've done my best to piece together her thoughts: 

"Dressing up at home was fun and all but one day I had an epiphany , knowing I had to take my crossdressing a step HIGHER, 1,000km above the clouds higher. I traveled to Greece in October, and was dressed femme for the whole trip. Nobody questioned me at all. It really surprised me. I got a lot of compliments on my dress, shoes, hair, bag. I think they all knew, especially passport control. Passing through TSA  was terrifying! I was expecting to take off my wig and prove I was a man, hahaha but they let me slip on by. They double looked at me because I look so different as a man, I guess they could see certain features in my face or just assumed I was trans but hadn’t updated my gender on my passport."

    In addition to sharing her thoughts on her air travel experience on reddit, Lulu shared a series of images on her TikTok, where she chronicled her journey while crossdressed in the airport. See those images below:

    I audibly gasped when I saw Lulu used the men's restroom when the line for the women's was too long. That's when I knew she was one brave badass bitch! Not only is she taking an international flight while crossdressed without any fear but on a whim she's using the men's restroom! Damn she's cool! I wish I had even a portion of the gusto she does! Check out some pictures of her full dress below, as well as some triumphant selfies Lulu took once she finally arrived on the plane.

    Isn't her dress just amazing?! I can't get enough of it! Lulu looks so glamourous wearing it too! After arriving at her destination, Lulu went out for a night out on the town. To commemorate the moment of her getting to walk around a new country while fully crossdressed she took a video of herself:

    Of course sadly all vacations must come to an end and it would eventually come time for Lulu to fly home. However she wasn't going to waste another opportunity to crossdress on a plane! This time she wore a black top and white furred vest. Lulu never disappoints and yet again looks totally glamourous on her plane ride!

    Speaking of Lulu looking glamorous while traveling, this isn't the first time she's got all dolled up for traveling. Prior to her experience at the airport she also dressed up for a ride on a train, and the subway. Check out images and some videos from that travel experience below!


    Well, I think I can comfortably say Lulu is one of the most amazing glamourous and BRAVE crossdressers I've ever seen. The fact that she is brave enough to 1. Go out in public dressed, 2. put herself in very publicly visible situations such as public transit, and 3. do it all while look fabulous is nothing short of amazing! I know I'll certainly be watching Lulu's socials for more amazing adventures to come!

-Carly

Tuesday, July 29, 2025

Ash Ketchum, Crossdresser?!

 Hello There,

    There is certainly no shortage of crossdressing themed fan art online, but perhaps one of the most frequently featured characters is none other than Pokémon's own Ash Ketchum! Ash was the Pokémon franchise's main character in the anime television series for almost two decades. With his go to catch phrase of "gotta catch 'em all" you'd think he'd be talking about Pokémon, not women's clothing! This post is the start of a new series I will be working on covering crossdressing fan art based around classic cartoons and media. So zip up those dresses and strap on some Poké balls because Ash Ketchum is gonna be doing some crossdressing, or should I say "Ashley Ketchum".

    Let's start out by establishing that there is actually precedent for Ash crossdressing in the original anime. Over his twenty year span as Pokémon's protagonist Ash did actually crossdress several times for one reason or another. Be it to avoid the clutches of the evil team rocket, or to compete in a girls only Pokémon league, almost every new Pokémon generation saw Ash dressing as a girl for one reason or another.

    Although often used for comedic effect, for those of us who were struggling with gender identity at a young age, it still left a lasting impression on us. Ash's crossdressing hijinks seemed to have had a lasting impression on many people it seems because there is a massive library of fan art depicting him crossdressed. He has even been dubbed "Ashley" by his fans, who see him as one of the most commonly associated cartoon characters with crossdressing. I know I certainly developed quite the love for "Ashley Ketchum" when I was young, because I was at a similar age, loved Pokémon, and could identify with a young boy trying crossdressing for the first time. So it's no surprise that many others have the same fondness for Ashley as I do.


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    Interestingly perhaps the most commonly featured dress in Ashley Ketchum fan art is one he never wore. While exploring the Sinnoh region he traveled with fellow Pokémon trainer Dawn. Dawn competed in Pokémon contests which were essentially shows designed to show off a Pokémon's beauty rather than using them to fight in trainer battles. When participating in contests, competitors would wear elegant outfits to compliment their Pokémon. Dawn would typically wear a pink dress with a white collar accented by little pink bows. This is the dress that Ash is probably most commonly depicted wearing interestingly enough. Perhaps it is the popularity of this dress that drives artists to depict Ash as wearing it, or perhaps it speaks to how popular Dawn was as a character. Maybe it's just an amazing dress. What ever the reason Ash has been depicted as being no stranger to wearing Dawn's iconic contest dress!

    In addition to Ash frequently wearing Dawn's dress, Dawn is frequently depicted as being the one to either encourage Ash's crossdressing, or help him along in the process. Again this is probably due to Dawn's popularity as a character, or perhaps its just because in the end most young crossdressers just long for a friend to dress with. But Dawn's role in the "Ashley" crossdressing saga is well represented.


    In addition to Dawn, Ash has had several female companions who have accompanied him across his journeys through the different Pokémon regions. To fan artists, it sure seems like there is no shortage of Poké-girls willing to indulge Ash in his crossdressing. His own mother Delia Ketchum even gets in on the crossdressing fun sometimes!


    It's not just Ash's female companions that want to get in on the fun however, many of Ash's fellow male Pokémon trainers have shown an "interest" in his Ashley persona. Granted unlike the Poké-girls, these boys seem to enjoy Ashley more for her appearance than the act of getting her all dressed up. Ash must make quite the convincing girl, because all the boys seem to swoon over Ashley!






    Ash certainly seems to have a lot of fun with his Ashley persona, and what could be more fun than dressing as Disney Princesses (ya'll know I'm a big fan LOL). Ashely just couldn't help herself and had to partake in some princess fun as well!


    Interestingly enough a modern trend of Ashley fan art is to pair her with the Jessie from the villainous Team Rocket! Jessie has gone so far with Ash's crossdressing that she is even beginning to call him her daughter!

        In addition to dressing up as Jessie's daughter, Ash has gone so far as to dress as his "mom" Jessie. Although Ash often seems to use dressing as his mother as an excuse to dress sexily, maybe some Oedipus Complex going on here?



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    Well there you have it friends, I've covered almost all the aspects Ash Ketchum's crossdressing fan art, or should I say Ashley Ketchum? He certainly seems to enjoy indulging in the joys of femininity, doesn't he! Given that throughout his tenure as Pokémon's anime protagonist he would periodically crossdress every few years, meant that generations of young viewers got to connect with a male character who wore women's clothes. For many, Ash may have been their first exposure to crossdressing, and with such a massive backlog of fan art online, the influence Ashley Ketchum has on many young crossdressers can not be overstated.