Monday, November 24, 2025

My Summer With Aunt Sarah Chapter 10

The Finale

Tyler’s dull life marched onward. His senior year of high school was uneventful and provided little excitement to look forward to. Tyler’s parents had obviously fallen out of love, and now held their marriage together out of spite. Everyday blurred together as he confined himself to his room, reading, playing video games, and his time with Sarah ever on his mind.

He texted with Sarah quite frequently when they first separated at the start of the school year. But now they only texted once every few weeks at the most, sending pictures of cute outfits or funny memes to each other. They were nowhere near as close as they’d once been. As the year went on Tyler realized his relationship with his beloved aunt was unfortunately slipping away.

As his senior year of high school was coming to an end, Tyler was facing a crossroads in his life. He was already enrolled in an online college for video game design next year, but now he’d have far more free time to spend his life as he pleases. All the plans he was beginning to make for his life were halted shortly after his 18th birthday however; his parents were getting a divorce. They waited until after Tyler turned 18 to avoid a legal battle over custody and child support. 

Tyler’s parents were also going to be selling their home, and moving into separate apartments after Tyler graduated High School. Since neither of his parents had particularly strong parental instincts, they left it up to Tyler if he wanted to move in with either of them, or strike off on his own. He’d initially planned to live with his father since he was footing the bill for Tyler’s college. However one morning when he reached for the pair of panties his aunt had given him it all clicked. This was his chance to return to Sarah!

Both of his parents at separate times floated the idea of Tyler getting his own apartment during college, so he knew that they’d be ok with him not living with either of them. All he needed to do was reach out to Sarah and ask the big question. But how to ask, they had become so distant, it seemed like an impossible request to fully move in with Sarah after so long apart.

Well after fixating on the idea for weeks, he finally bucked up the courage to ask. He spent hours drafting the text asking to move in with her, and after a while longer of nervous anticipation he sent it. He eagerly awaited a response and could hardly focus on anything until at last his phone vibrated with a text from his aunt. It said only a single word, but it made Tyler’s heart skip a beat.

Yes.

His heart was racing, his dreams coming true! After a year of agony he was going to return to Sarah and the magic of her house of feminine dreams. Neither of his parents seemed to mind the idea when he told them he would be living with Sarah, probably he'd finally be off their plate. But his parent’s indifference didn’t matter any more, he was going to a home where he felt love.

After graduation day the time had finally come. He packed his bags, swiftly said his goodbyes and left for the train station. He couldn’t sit still on his journey; he was so excited! After a long taxi ride he finally arrived at Sarah’s beautiful home. Tyler swiftly collected his things and practically ran to the front door. After a ring to the door bell, there she was, his beautiful Aunt Sarah. She flung her arms open and hugged him tighter than ever before. 

At last she kissed him on both cheeks and held him at arms length, saying “welcome home Taylor”.

Sarah then sent Taylor up to her room to see a “little surprise” Sarah had set up for her. When Taylor opened the door to her room, her jaw dropped. The whole room had been redone! The walls were painted light pink, there was a canopy over the bed, a huge lighted vanity with a massive makeup collection, and sparkling string lights creating magical mood lighting. As if the shock of the room wasn’t bad enough when she opened the closet her mind was blown once again. It was almost completely full of clothes, some of Taylor’s favorites from Sarah’s closet but also new things as well! Dresses, jackets, blouses, skirts, swimsuits, nightgowns, robes, so many wonderful goodies! As she filed through the hangers and reached the end there were still more surprises still! Taylor’s prom dress from the prom night she and Sarah shared, but a variety of new costumes as well. Princess dresses, Wonder Woman, Sailor Moon, a lolita dress, a french maid uniform, and at the back an extravagant wedding dress. Every drawer in the room’s dresser was filled too! Bras and panties of every color and style, pantyhose, slips, shapewear, pajamas, and an entire drawer dedicated to various shapes and sizes of breastforms.  In the bathroom there were pink towels and all manner of feminine self care and hygiene products such as a dozen or so different skin care creams and sprays, deodorants, maxi pads and pantyliners of several sizes, and even some always discretes. 

It was an overwhelming spectacle; every possible aspect of replicating femininity was now at Taylor’s full disposal. She knew her life was to be forever changed from here on out. After spending the next hour fully shaving, doing some skin care, and applying makeup, she threw on a nightgown and robe and headed down to Sarah.

“There she is, my beautiful girl!" Sarah said with outstretched arms.

Taylor flung herself into Sarah’s arms and at last the world was right again. She was here, in this magical home, where she could be herself and enjoy all the joys of womanhood. She was with her Aunt who she loved more than anyone in the world, and who so desperately loved Taylor as well. Her summer with Aunt Sarah left Tyler forever changed, and now Taylor looked forward to the rest of her life with her new Mother, Sarah.

The End...

Chapter 9<--------

My Summer With Aunt Sarah Chapter 9

Bitter Goodbyes 

As the weeks passed by, Taylor delved deeper and deeper into her feminine persona. She wore makeup and a wig every day, she started using a more feminine voice, and did her best to emulate the behavioral cues of a teenage girl. Sarah even encouraged Taylor to wear panty liners every few weeks to emulate the true feminine experience of a flowering teenage girl, which Taylor gladly did.

But as time went on, the unspoken truth became louder and louder. Eventually the summer was going to end, and Taylor was going to have to return to his parent’s home. They were far more conservative than fun loving Aunt Sarah, and there was no way they’d ever allow Taylor’s new lifestyle to continue. Which meant every ounce of time Taylor and Sarah had remaining together was precious. At last Sarah asked the dreaded question that was on both their minds.

“So, what are you going to do when you go back home?” Sarah asked grimly.

“I don’t really know. Probably not this”. Taylor said, gesturing to herself.

“Are you going to tell them about any of this? About how you feel about yourself?” Sarah asked with a sullen curiosity.

“No, they’d never accept me like this, they barely have time for me as it is, when they’re not busy fighting with each other. I think they’d blow a gasket if I showed up like this. It would just be easier to dress as a boy again”. Taylor said with an exhausted breath.

“Oh baby, I’m sorry. I know life isn’t easy living with them; hell it’s the whole reason they sent you here for the summer. But they’ve been trying to work on their relationship while you were away, maybe things will be better!” Sarah said with an obviously fake enthusiasm.

Sarah’s words of encouragement did nothing to soothe Taylor’s worries. But unfortunately there was nothing the two of them could do. They spent their last few weeks together doing as much as they could to make the most of Taylor’s crossdressing. Photoshoots and fashion shows, slumber parties, mini spa days, all helped to keep their minds off the dreaded deadline which was approaching. 

The week before Taylor was scheduled to return home, Sarah brought a box down from her room, and set it on the table in front of Taylor. 

“What’s this?” Taylor asked excitedly.

Sarah let out a sigh and said “Well….I know you were planning on going back to dressing as a guy when you returned to your parents…. So I figured it was time to replace the clothes you ruined all that time ago.”

When Taylor opened the box there was a week's worth of boys clothes, replacing the set Tyler had ruined several months ago. Taylor let out a sigh as it finally sank in that she’d be returning to her old life soon. She’d live in a home hot with conflict, and in a body she was no longer comfortable in. At last a tear fell down her face, and as she went to dry it, she was suddenly enveloped in Sarah’s warm embrace. In that embrace she felt safe, and loved; and all at once the tears started flowing.

The trip to the train station was bitter. Tyler came downstairs dressed as a boy, all packed up and ready for the return journey home. Their car ride to the train station was quiet, the air filled with a somber tone. When they pulled up to the drop off curb, both said nothing.

After a brief moment Tyler finally said “Well….thanks for everything", and opened the door to leave. 

As he got out, Sarah suddenly got out and rushed around the car to give him the tightest hug! Tears streamed from both as their goodbye was finally here. 

“You’ll always have a home with me” Sarah whispered into Tyler’s ear as they hugged. “Taylor will always have a home with me”. 

At last Sarah kissed him goodbye and returned to her car, waving one last time and pulling away. The emptiness Tyler now felt was palpable. He knew his life would never be the same.

While on the train ride back Tyler went into his backpack to pull out a book and found a pink envelope. He opened it and found three things inside, a letter, one of Taylor’s favorite pairs of pink panties, and a photo of Taylor and Sarah from their prom night. 

The letter said:

My dearest Taylor, 

I can not express how much fun I’ve had spending these past few months with your new feminine self. I will always cherish the times we spent together, as the best moments of my life. I’ve always wanted a daughter, and you gave me the ability to finally play mother for a little while, as you learned all there was to know about womanhood. You blossomed into a beautiful young woman while you were here, and it truly broke my heart to see you have to return to the melancholy of boyhood. If you want to return to womanhood, my home will always be a safe space for you. Enjoy your senior year of high school, I’ll have you in my thoughts.

Love you always, Sarah

*****

While it was true his parents had seemed to improve their relationship a little, his life at home was a far cry from the luxury comfort of Aunt Sarah’s. They still would on occasion sling an insult or angered glance. The air was tense, and Tyler was walking on eggshells. If all that wasn’t bad enough he longed for his time in a more feminine role.

He wore the panties Sarah gave him often, but it wasn’t much to recapture the magic of his summer with Sarah. On occasion when he was home alone he’d sneak into his mother’s room and try on her clothes. She had nowhere near the huge assortment of clothing that Sarah had, but it helped to fill his feminine itch. But given the intense fear of being discovered by his parents, Tyler kept these moments brief.

His life was dull, school provided little excitement, and when he returned home, he had to confine himself in his room to avoid the tension between his parents. He longed for his fun loving feminine days at Sarah’s. Finally Tyler committed to himself that if ever he had the opportunity to escape these doldrums he would!

My Summer With Aunt Sarah Chapter 8

Prom Night

“Oh my gosh, you did such a good job!” Sarah screamed excitedly at the sight of Taylor’s makeup, and immediately running over to hug her.

“Thanks!” Taylor said while blushing. “It doesn’t look quite as good as when you did it.”

“That’s totally fine, it was your first time! You still did a great job!” Sarah said getting a better look at Taylor’s makeup.

“Yeah…..the eyeliner was really hard” said Taylor.

“Eyeliner is hard for everyone, don’t cut yourself up about it” Sarah said releasing Taylor.

“You certainly ordered a lot of packages” Taylor said, gesturing towards the mountain of boxes that had been delivered earlier in the day.

“I know, isn’t it exciting! Thanks for bringing them in for me!” Sarah said while surveying the boxes.

Taylor was about to tell her funny anecdote with the knock at the door, but Sarah interrupted her, clapping her hands together and saying “OK, let’s begin!”

The next two days were filled with unending feminine bliss. They painted each other’s nails, did facials, had a slumber party, performed fashion shows and photoshoots, tried on costumes and did just about every activity that Sarah could think of that Taylor had yet to do as a girl. Taylor was in heaven, everything Sarah had planned was so much fun; and Sarah always made Taylor feel so uplifted. 

The grand finale of their weekend was to be a mock prom (Since Tyler didn’t get to attend her junior prom as a girl). Sarah had bought Taylor a pink satin prom dress with rhinestones around the bodice. As Sarah put decorations up downstairs, Taylor stared at the dress, lying delicately on her bed. As she lightly brushed her fingers over the soft satin fabric, alll she could do was smile, she had no idea how quickly her life would change, but she had found such joy in what it had become.

She slipped her arms into the thin straps, the fabric sliding coolly against his skin. As she guided the dress up over her shoulders, there was a brief shiver, part nerves, part thrill. Looking in the mirror, she thought to herself that she looked exactly like the kind of girl she would have liked to take to prom. Now she had become that girl. 

When she came down stairs Sarah was waiting for her, wearing the blue prom dress she had worn to her original prom. There were streamers, a red carpet, a punch bowl, everything they might have needed for their at home prom.

“You looking ravishing darling!” Sarah said as Taylor came down the stairs.

“Thanks, I love this dress!” Taylor running her fingers down the sides of her dress.

“I knew you would! I have impeccable taste after all!” Sarah said gesturing to her surroundings.

“It all looks so amazing!” Taylor said awestruck at the obvious work Sarah put into decorating.

“I know right it came out super well, and don’t worry I only spiked the punch bowl a little bit” Sarah said with a coy smile.

They then proceeded to take lots of fun photos, eat some snacks, and dance like crazy to modern pop hits. The night could not be any more fun for Taylor and Sarah, the spiked punch certainly helped their glee as well. Their electric energy came to a standstill however when a slow song came up on Sarah’s playlist. The pair stopped dancing and stared at each other. 

Sarah chuckled and said “Come here”. She grabbed Taylor’s hands and put them on her waist saying “here, like this.”

The two swayed back and fourth, slow dancing together, eyes still locked together like a hypnotic trance. The moment seemed to carry on forever, the air between the two heavy with spellbinding affection. At last Taylor broke her gaze to put her head on Sarah’s chest as they continued to slow dance. Sarah held on just a little bit tighter and kissed Taylor’s head. When at last the song came to an end, their swaying stopped but Tayler didn’t let go of Sarah, in fact she seemed to hold her more tightly. 

At last Taylor looked at Sarah and said “Thank you for everything”

“Of course darling” Sarah replied. “Anything for my little girl”. 

After some more stops at the punch bowl and some more crazed dancing their night finally came to an end. Their night of frivolity had left the pair exhausted. After helping each other up the stairs, Taylor led Sarah to her room when Sarah went to drop herself on the bed she accidentally took Taylor down with her.

“Oops” Sarah said. “Well I guess this just turned into another slumber party”. She then chuckled. 

It was only mere moments later that the two of them had fallen asleep, still wearing their prom gowns and all. They drifted off to sleep in a literal feminine embrace. Their night among the most fun, and affirming either had ever had in their entire lives. 

My Summer With Aunt Sarah Chapter 7

A Knock At The Door

After his heart to heart with Sarah, the night before, Tyler, or “Taylor” as she was now known, was feeling feminine euphoria the next day. Like she had earlier in the week, she spent her day doing a little fashion show with all of Sarah’s clothing. Only this time she had her new breast forms that she got to try out. There seemed to be no end to Sarah’s collection of clothing, so many different items and outfits to try. Taylor was so excited for whatever new feminine education Sarah was going to whip up with her, that she just had to spend her time doing girly things in the meantime!

At long last, after a day of anticipation, Sarah returned home. Once again she walked through the door with a box in her arms. She also seemed to be glowing with excitement and anticipation for the time ahead.

“Taylor, your new mother is home!” Sarah excitedly called out not long after coming inside.

“Hey Mom! Another package?! Taylor asked with curious excitement. 

“Well of course, I promised that I’d teach you more about being a girl, didn’t I? Well there was a few extra goodies I needed”. Sarah said proudly.

“Oh..... that’s exciting” Taylor said with a newly piqued interest.

Sarah chuckled and said, “Yup, but let’s get dinner out of the way, and then our education session will begin!”

Taylor could barely contain herself during dinner, the anticipation was killing her. What could be next in her “feminine education”. Whatever it was, ultimately she was just excited to spend time with Sarah. Although the whole mother/daughter roleplay was still very new, and a little weird, Taylor could not deny how much she enjoyed spending time with Sarah. Certainly, she enjoyed spending time with Sarah far more than her own parents, so maybe the roleplay made sense.

When dinner was over Sarah took Taylor by the hand and once again made the trek up the stairs and into Sarah’s bedroom. She sat Taylor down on the bed and made room for the box of new goodies on her vanity. She opened the top of the box, composed herself and turned to Taylor.

“Ok, you dress like a girl, time to look like one. Every woman wears makeup just about every day; and it’s time for you to learn too.” Sarah said poignantly as she took each piece of makeup out of the box.

“Ohhhh…….” Taylor responded, feeling a little overwhelmed at the prospect of having to do her own makeup.

“Don’t worry we’re gonna keep things simple, a little bit of makeup goes a long way” Sarah said reassuringly. “That being said, this is what will finish the look!” She then said as she pulled a wig out of the box.

“Wow, no way!” Taylor said in disbelief.

“Yes way! You ready to look totally different?” Sarah asked, putting her hands on Taylor’s shoulders.

Taylor nodded, and they were off on their makeup journey. Sarah explained and applied the basics of foundation and concealer, the annoyances of eyeliners, putting on mascaras, touching up eyebrows, a bit of blush, and finally some lipstick to top things off. When all was said and done, Taylor was shocked; she looked totally different. And then came the wig, it was dirty blonde and sat just below the shoulders. After it was on, she looked unrecognizable.

“Well, what do you think?” Sarah asked

“I….I look so different, I look like a real girl” Taylor said in shock.

“You look like you” Sarah said, giving Taylor a kiss on the cheek. “And doing makeup really wasn't that hard was it?” She followed up with.

“No not really” Taylor said, shaking her head and looking up at Sarah.

“Good, do you want to try it yourself tomorrow” Sarah asked.

“Uhm, sure I can try!” said Taylor, still enthralled by her reflection in the mirror

“That’s my girl! I bought all this makeup just for you, so you can keep it in your room.” Sarah said motioning towards Taylor’s room.

“Thanks Mom!” Taylor said as she packaged things up.

Taylor packaged up all her new makeup, and relocated it to her room. The pair then relocated downstairs for their nightly ritual of watching TV together. Taylor was feeling feminine euphoria, she truly felt like a new girl. During one of the commercials, Sarah struck up a new conversation.

"So.... still liking being a girl?" Sarah asked.

"OMG Yes! Look at me!" Taylor said excitedly while gesturing to herself.

"Well you think you can handle doing your own makeup tomorrow morning?" Sarah asked inquisitively.

"If it means looking like this again, I can certainly try" Taylor said excitedly.

"That's my girl!" Sarah  proudly proclaimed. 

As the night came to an end, they said their goodnights and headed upstairs to their rooms. As Taylor cleaned the makeup off of her face, she could not help but stare at her reflection and marvel at the new woman she had become. She was starting to love her new life

The next morning the first thing Taylor did after waking up was skip over to her makeup vanity. Although for Taylor, putting on makeup wasn't quite as easy as Sarah made it seem the night before. But after an hour or so of trial and error, Taylor was feeling satisfied. She then slipped her wig on and paraded around the house, feeling fulfilled. After awhile she found her way to Sarah’s room to pick her outfit for the day. What better outfit than a pink sundress; it certainly went with her new full feminine appearance. 

Later in the day while reading a book on the couch there was a loud knock on the door. Taylor’s eyes shot over to the door in a sudden panic. Who could be there, what do they want, what will they think of the boy dressed as a girl who opens the door? All sorts of thoughts were rushing through Taylor’s mind. She was feeling nervous, none of what was happening to Taylor was normal, but until now she was safe in the bubble of Sarah’s home. 

She needed to determine who was at the door; so she ran upstairs to get a view of what car may have been out front. To her surprise there was no car out front. But then who was knocking on the door? Taylor ran downstairs and slunk her way to the front door. When she took a look out of the peephole there was no one there. Taylor was getting frustrated, did she imagine the sound which made her so nervous?

Finally she opened the door and it all became clear. There were several Amazon packages all lying by the front door; it must have been a delivery driver who knocked. Feeling relieved Taylor started bringing the packages in. Sarah must’ve had quite the shopping spree the night before. Whatever further feminine education Sarah had planned for Taylor, it must’ve been quite elaborate.

Chapter 6<--------> Chapter 8

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!

______________________________________________________________________

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.