The allure of materials, clothing texture and cut, makeup and jewellery is just irresistible to us… but why?
Do you recall yours?
I was twelve or thirteen and it was the start of the summer holidays. And this specific summer break would be the time when I got to fully explore my feminine, sensual and erotic self.
I don’t recall if I was dressed for my first orgasm, but I do know that I dressed as much as I could that summer, and always managed to play with myself and bring myself to earth shattering orgasms.
My first item of clothing that was not stolen from a sister or my mother, so in essence was my first choice for me, was a pair of fishnet stockings. Honestly, I thought I was going to come just taking them out of he polyethene bag.
That summer I also got to play a lot with the girls, all my age. Doctors and nurses. Sometimes I was the nurse too. It was all pretty innocent, I was too young to really know what was going on. All I knew was I loved feminine energy, pretty girly looks and clothes, and it made me cum so hard I needed to it right again right away. I recall fourteen orgasms in one day being my record.
I KNOW! What a little slut. And I loved it.
Of course being discovered by my mother was a fear that loomed large. And it did finally happen. And the repercussions were severe and kicked my feminine self into a deep abyss of shame. But that story is for my book.
Other notable moments include the first time I wore heels. That was maybe ten years into my journey, in a pre-internet world where larger sized high heels were impossible to find. But when I did, oh my. I was shaking for hours before, duting and after.
Then the was the first time I shared my girly self, fully dressed, with another girl, who encouraged me to let myself go and perform for her. That is the subject of the next post. Phew! (needs to lie down in a dark room!)
Now gurls, what do did you tell me in the survey? About your first orgasm in your knickers, heels and stockings?
'Forbidden but exhilarating. I felt guilty but so alive.'
Hailey, Boomer, Occasional Crossdresser
“Aged 13 it was the best feeling my body had experienced.”
Amanda, Post Boomer, Occasional Crossdresser
“Amazing.”
Lilly, Gen Z, Sissy
“Amazing. My wife made me up with makeup. I dressed in a skirt, top, stockings and masturbated in front of her.”
Phoebe, GenX, Occasional Crossdresser
“As a teen, I took ballet. One day after class, I began to rub myself with my tights on. It felt just so right when I had my orgasm. I knew that I needed to wear some form of hosiery daily.”
Jasmine, GenX, Sissy
“At first, I would remove the clothing right away because after an orgasm I wouldn’t be in the mood anymore, but now that doesn’t always happen. It depends, but most of the time I continue to stay dressed.”
Michelle Cox, Millennial, Occasional Crossdresser
“Awesome! Just the feel of wearing lingerie.”
Marsha, Boomer, Regular Crossdresser
“Better than I thought.”
Roxi, Millennial, Sissy
“Bliss.”
Samantha, Gen Z, Sissy
“Caged and pegged to an exploding orgasm.”
Jessica, Millennial, Regular Crossdresser
“Climaxing in a maid’s outfit, looking at myself in the mirror, made me feel more feminine than ever before.”
Veronica, GenX, Occasional Crossdresser
“Completely euphoric. I finally felt whole.”
Sophie, Gen Z, Sissy
“Dressed in a satin slip, I touched myself and melted into pleasure. It was so different from anything I’d felt before.”
Charlotte, Boomer, Occasional Crossdresser
“Dressed in a tight dress and heels, I realized I didn’t want to go back to my old self.”
Rebecca, Millennial, Regular Crossdresser
“Ecstasy beyond words. I never wanted to stop.”
Stephanie, GenX, Occasional Crossdresser
“Euphoric. The soft panties against me, the stockings on my legs—it was perfect.”
Kimberly, Millennial, Regular Crossdresser
“First time I ever felt like a woman.”
Tina, Gen Z, Sissy
“First time I knew I was more than just a man in women’s clothes.”
Olivia, GenX, Regular Crossdresser
“Fully dressed, including makeup. I couldn’t believe how good it felt to orgasm while feeling so feminine.”
Emily, GenX, Occasional Crossdresser
“Had never felt more right in my life.”
Bianca, Millennial, Sissy
“Heavenly. I couldn’t believe I had waited so long to try it.”
Rachel, Gen Z, Regular Crossdresser
“Helplessly overcome by pleasure. I knew I had to do it again.”
Isabelle, Boomer, Regular Crossdresser
“I felt feminine in a way I never had before.”
Madison, GenX, Regular Crossdresser
“I was wearing a lace bodysuit, and when I climaxed, I felt more connected to myself than ever before.”
Sophia, Millennial, Regular Crossdresser
“I wore a wig and full makeup, and when I finished, I realized I had truly found myself.”
Vanessa, Gen Z, Sissy
“In a satin nightgown, feeling utterly lost in pleasure.”
Natalie, GenX, Occasional Crossdresser
“Indescribable joy. Like something that had been missing was finally there.”
Chloe, Millennial, Regular Crossdresser
“It was an awakening. I had never felt so comfortable in my own skin.”
Evelyn, GenX, Regular Crossdresser
“It was like I had unlocked something deep inside me that had been hidden for years.”
Alyssa, Gen Z, Sissy
“Life-changing. I knew I’d never stop dressing after that moment.”
Lucy, Boomer, Regular Crossdresser
“Like floating on air, wrapped in silk and warmth.”
Amber, GenX, Occasional Crossdresser
“Mind-blowing. I finally understood who I was.”
Victoria, Millennial, Regular Crossdresser
“My body tingled in ways I had never felt before.”
Brianna, Gen Z, Sissy
“Nothing had ever felt so right before that moment.”
Dani, GenX, Regular Crossdresser
“Orgasm while looking at myself in a dress was a whole new level of pleasure.”
Fiona, Millennial, Regular Crossdresser
“Overwhelming in the best way. I couldn’t stop shaking.”
Jessie, Boomer, Regular Crossdresser
“Pure ecstasy. Like I was in the body I was always meant to be in.”
Mia, GenX, Occasional Crossdresser
“Satin, lace, and a deep, satisfying release—perfection.”
Kayla, Millennial, Regular Crossdresser
“Sensational, powerful, and incredibly addictive.”
Jade, Gen Z, Sissy
“Sheer bliss. The feel of lingerie heightened everything.”
Lana, GenX, Occasional Crossdresser
“So feminine, so perfect, so right.”
Elena, Millennial, Regular Crossdresser
“The best orgasm of my life.”
Bella, Boomer, Occasional Crossdresser
“The clothes made everything more intense.”
Claire, GenX, Regular Crossdresser
“The first time I felt truly alive.”
Lauren, Millennial, Regular Crossdresser
“Transcendent. I wanted to stay in that moment forever.”
Scarlett, Gen Z, Sissy
“Unbelievably intense. I never wanted to go back to my old self.”
Alice, GenX, Regular Crossdresser
“Utterly intoxicating. Like I was someone new.”
Faith, Millennial, Regular Crossdresser
“Wearing a full outfit and seeing myself in the mirror made the experience unforgettable.”
Holly, Gen Z, Sissy
Analysis
The First Time: A Sensory Awakening
For many of us, that first time slipping into panties, a silky slip or nylons, well that that speaks to the soul, and it is more than just a moment—it is an awakening. It is the rush of discovery, the sensual intake of breath as fabric glides eroticaly against skin, the thrill of the forbidden femminine, and the validation of long-buried yearnings.
Euphoria & Awakening
Some describe their first experience as nothing short of euphoric. “It was as if I had been asleep my whole life and finally woken up,” shared Olivia, GenX, Regular Crossdresser. “When I first saw myself in the mirror, dressed head to toe in lace and satin, I knew—this was me.The sensation was electric, an unshackling from years of uncertainty, a first step toward authenticity. It was not just about pleasure—it was about becoming.”
Guilt & Forbidden Thrill
But with awakening can come conflict. “I knew it was ‘wrong,’ but that only made it more exhilarating,” admitted Hailey, Boomer, Occasional Crossdresser. The contrast between pleasure and shame created a heady mixture of emotions—guilt laced with excitement, fear intertwined with desire. It was the delicious pull of something that felt too good to resist, the heart pounding with anticipation as lace met skin. “I felt like I was crossing into a world I wasn’t supposed to enter… but oh, how I wanted to stay.”
Sensory Pleasure (Fabric, Texture)
Beyond the emotional impact, the experience is intensely physical. The glide of silk against bare skin, the delicate embrace of lace, the firm yet yielding give of stockings—every texture speaks in a language of its own. “The first time I wore satin, I couldn’t stop touching it,” confessed Rachel, Gen Z, Regular Crossdresser. “I was completely lost in the sensation. It felt like a secret caress, whispering against my body, making my skin tingle.” Every swish of a skirt, every brush of fabric, is a love letter to the senses.
Validation & Identity Discovery
For some, the experience was not just about the clothing—it was about seeing their true self reflected in the mirror for the first time. “I finally felt like me,” said Sophie, Gen Z, Sissy. The external shift unlocked an internal truth, a realization that had been waiting to surface for years. “For the first time in my life, I felt whole. It wasn’t just about how I looked—it was about how I felt inside. Like everything had clicked into place.”
Partner Involvement & Encouragement
And then, there are the moments of acceptance. Some found not just self-validation but encouragement from loved ones. “My wife smiled and handed me a pair of her heels. ‘Try these too,’ she said,” recalled Emily, GenX, Occasional Crossdresser. “She kissed me and told me I looked beautiful. I nearly cried—because for the first time, someone else saw me the way I saw myself.” I know I am not alone in wishing we all had a partner like this.
The first time is a doorway into something deeper—a world that has always been there, waiting to be embraced. And when that moment comes, there is no turning back—only the intoxicating promise of what lies ahead.
What is clear is just how important getting our gurl on can really be to us.
In the next post...
Let’s look at, if we are lucky enough, our first time dressed and sharing intimate time with another person…
Please do feel free to leave your own comments about these stats below and I will be sure to answer you.
JennyX
Read the real intimate stories behind these survey results in the 2025 Survey, including Aanya’s story of her first hands-free orgasm.
Explore The 2025 Whole Survey...
Part 1: Hello, Darlings, Here We Are For Our Second Date… The Results Of The 2025 Crossdressing All Gurl Survey
Welcome back gurls. This time, I wanted to ask a few specific questions (more on that in the analysis) and also to lean way more into fantasy. I wanted to lift up your skirt and have a peek inside your panties, you naughty little minx. And I can tell you, some people welcomed that rather delicious voyeuristic probing as they shared with me all their wicked dreams, desires, sometimes even needs. OK gurls, let’s get in bed together and explore each other. Intimately.
Part 2: Shall We Spend A Fantasy Gurl Night Together?
Welcome back gurls. This time, I wanted to ask a few specific questions (more on that in the analysis) and also to lean way more into fantasy. I wanted to lift up your skirt and have a peek inside your panties, you naughty little minx. And I can tell you, some people welcomed that rather delicious voyeuristic probing as they shared with me all their wicked dreams, desires, sometimes even needs. OK gurls, let’s get in bed together and explore each other. Intimately.
Part 3: Colours, Textures, Materials and Clothing… Oh my!
Nothing gets me hotter than black nylons on freshly shaved legs, or satin being caressed along my legs in nylons, or black patent heels, red calf length boots, lace trims, and fabrics that stretch and cling to my body sensually, erotically and femininely. For me, it’s all about the material, the colors, the textures, and the femminine clothing.
Part 4: Who Would You Love To Spend Intimate Time With?
Let me be clear, I firmly believe that we are all on a sexual spectrum. And that we can move along that spectrum. Sometimes slightly. Sometimes dramatically.
Part 5: Why, When And Is It Enough?
We do seem split kind of down the middle. Most of us finding sexual pleasure from dressing up, the rest because if makes us feel more feminine. It’s important to remember that the survey is skewed to an older demographic too. I suspect this indicates that for Millennials and older, dressing up was socially steered into being a kink in decades past, where now I suspect it would be explored more as an identity.
Part 6: My First Orgasm En Femme
I was twelve or thirteen and it was the start of the summer holidays. And this specific summer break would be the time when I got to fully explore my feminine, sensual and erotic self. I don’t recall if I was dressed for my first orgasm, but I do know that I dressed as much as I could that summer, and always managed to play with myself and bring myself to earth shattering orgasms.
Part 7: My First Experience With Someone While Dressed En Femme
“The first time I got fucked while in full girl mode, I couldn’t believe how natural it felt. I finally felt like myself.” Chloe, Millennial, Sissy
Part 8: Fantasy time, when wishes DO come true!
I don’t mind admitting it. I was very young when I first had fantasies about having a fairy godmother show up and turn me into a gorgeous girl. If that happened, I could wear pretty frilly dresses, stockings, high heels, make-up, and jewelry every day, feeling confident that I would be accepted everywhere I went.
Part 9: What Advice Would We Offer Our Younger Self?
This final question is perhaps the most important. If we could trun back time, what would we do differently? There we some wildcards, like ‘Buy bitcoin’, but almost all responses were saying the same thing as Daisy, ‘Follow your femme dreams and don’t push your feminine energy away. Find your community and you will be more free than you can imagine.’
Part 10: Conclusions
And in conclusion…I saved one question for the end as it may be important, or maybe irrelevant. In my industry (creative industries), I noticed many of us have ADHD, which seems to put me, and others, at some odds with neurotypical people.I then wondered if that had any bearing on my inner femme, my kink, my girlie self? So I asked in the survey…
I live for all things feminine—stockings, heels, scarlet nails, and above all, the intoxicating touch of another woman. A translesbian muse and unapologetic hedonist, I share my most divine and wicked misadventures in words and now as a podcaster too. All gurls welcome. You are gorgeous. Just like me. xxx
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