My recent updates... Do read alone...
How My Husband Became My Wife… And A Whole New Chapter Opened
I got to online texting with the rather amazing Jane, who runs a page on Instagram called sissy__wives696 and I asked if I could share her story here… so here it is! Here’s what she emailed me… I became an ally by accident. My husband Sam and I got married just over five years ago. We
Meet Catherine Noir: A Novelist In Waiting… and Nylons
Catherine Noir, a GenX crossdresser, opens up to Jenny Raven about her awakening, purging, desire when dressed, and her wildest European fantasy.
Episode Seventeen: The Five Stages Of Rachel Spring
Rachel’s wife discovered her cross-dressing years ago – and the hurt and disapproval still shape how Rachel lives today. In this candid conversation, she describes dressing only behind a locked door, the thrill of a past visit to a BDSM dungeon, and the fear that time is running out to experience more.
My Podcast Returns! Who Will Be My Next Guest?
I am thrilled to share that I am back podcasting after a forced hiatus due to, you know, adulting! Who will be my first guest? I am choosing to interview more of the people in our glorious community, to hear their stories, their truths and of course, their take on my books.
I have a wild, imaginative, very specific and deliciously erotic sense of sexual fantasy.
Jenny on the thrill and nerves of living out feminine fantasies, why the details matter, and how a simple cheat sheet helps partners say yes.
Gurl Talk With Jenny Raven Podcast Re-Heeled: Who Do YOU Want To Hear From?
Gurl Talk is coming back, and I am looking for guests. Experts, people working in the adjacent trades, and crossdressers with a story to tell.
Meet Author: Dyvia Etymon
Mind control and feminization author Mistress Dyvia on 20 years of writing, from her first story in 2002 to Patreon, and the kinks and craft behind her fiction.
Meet the Author: Isabella Marks
Literotica favourite Isabella Marks on kink, confidence and writing trans and crossdressing erotica, in this Meet the Author interview with Jenny Raven.
Rocky Horror, A Personal Memoir And Tribute To The Original Frank’n’furter, Tim Curry
With the very sad news of the passing of the icon, legend and king, or queen rather, of six inch platform heels, Tim Curry, I thought I would share as tribute, an as yet unpublished chapter (and unedited!) from a new book. About my own Rocky Horror adventures as a teen, then the seismic impact it had on me. Tim, we will never forget you.
Why I Write Erotica by Phoebe Pearl
Sissy hypnosis is a sub-genre of erotic hypnosis built around the fantasy of sissification, the deliberate progressive shift from a masculine identity into a more feminine, often hyper-feminine one.
I was so turned on, I immediately wanted to dress as her and… what happens when gurls take the survey
One question I asked at the end of the survey, a free-form question, was this. How did you feel answering these questions? The results are startling and drawn from just under 1,000 entries (and growing daily).
Hard Won: Top Ten Erotic Author Pitfalls and Mistakes to Avoid, by DK Masters and Jenny Raven
A few days ago I posted an interview as pat of my authors series, with author DK Masters. Such a brilliant read. She shared the mistakes she made in her career and what to do about them in the original interview, but I broke them out here. Here are her top five, and mine to make it ten!
Meet The Author: DK Masters
From magical transformations to deliciously wicked fantasies, D.K. Masters takes us inside a world where gender, desire and imagination collide. Our interview is bold, sexy, surprisingly heartfelt – and guaranteed to leave you a little hot under the collar.
Every So Often, Jenny Goes Away… And It’s A Mystery To Me
Right now Jenny is asleep. More like sleeping beauty in a coma to be fair. This happens every so often. I don’t know why and I do miss her. What do I mean?
Have your Tried Sissy Hypno? Meet One Of The Top Creators, Sissy Cloud
Sissy hypnosis is a sub-genre of erotic hypnosis built around the fantasy of sissification, the deliberate progressive shift from a masculine identity into a more feminine, often hyper-feminine one.
Meet Melissa Jones: A Millennial Australian Crossdresser on Nylon and Lycra and Mistress Worship
Melissa is a Millennial crossdresser from Australia. Read her honest Q&A on Nylon and Lycra and Mistress Worship from Jenny Raven’s 2025 Crossdresser Survey.
Meet Heather: Crossdresser Survey 2025 on Lace & Public Play
Heather is a Millennial trans crossdresser from the US. Read her honest Q&A on Lace and Public Play from Jenny Raven’s 2025 Crossdresser Survey.
Meet Andi: A Gen Z US Sissy on Leather and Lace, Chastity, and Neurodivergence
Andi is a Gen Z sissy from the US. Read her honest Q&A on Leather and Lace and Chastity from Jenny Raven’s 2025 Crossdresser Survey.
How Do You Feel Sharing Your Most Intimate…?
One of the last questions in my new Crossdresser Survey for 2027 is, how did it feel taking the survey. The results were almost unanimous, and here’s just a few… I just had the best time completing your survey. I love that i have a space to delve into my inner self and explore what
Part 3: Girly Colours, Textures, Feelings, Playtime and Revelations
The Hedonism Of Feminine Fabrics, How They Look and How They Feel Destroys Me.
Part 2: Why Do We Do It, How Often and Do We Go Out Into The World In Heels Enough?
It’s the big question. Why? Why am I the way that I am? And why have I felt so locked in for so long? The stats tell us everything.
Meet Agony Aunt Jenny… How Can I Help?
Do you have a burning question? Do you need advice? I am not a doctor, but I have lived a life. So life lessons in high heels is what you will get.
Announcing the 2027 All Gurl Crossdresser Survey
I want you to share your soul, to pull down your metaphorical panties so that I can get a good peek inside, and to open wide, invitingly. Let me explore you. Every inch of you darling.
Interim Live Results from the 2027 Crossdresser Survey
You can swing back and see the live results here (minus the written word results which needs deeper human analysis). So what do you think? Do you enjoy it? What do you make of the charts below? Please do leave a comment.
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 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 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 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.
Ladies, Meet the Gorgeous Daisy Jenna from the UK, Answers from the 2025 Crossdresser Survey
I was 6 years old, it was my sister’s underwear and I enjoyed the comfort of the cotton panties. I would secretly wear them on days out. I also used to playfully wear my mother’s heels and loved the sound of them tapping on the wooden floor.
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 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 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 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.
Oh The Trend On Socials For Girlies Dressing Up Is Divine!
Nothing makes me feel more amazing, confident, and feminine than wearing black nylons, especially ten denier ones.
Pair them with a cute miniskirt and black calf-length high-heeled boots, and I’m in heaven.
I love relaxing, crossing my legs, and enjoying the wonderful feeling of being Jenny Raven. It’s my absolute favorite thing in the world. I don’t know about you, but if I could dress like this all the time, I’d die happy.
Finding Megan: An Intimate Journey of All Gurl Self-Discovery and Desires
My recurring fantasy is being with another crossdresser and his wife or girlfriend. I’d love another gurl that dresses classy, with sexy lingerie underneath. I want to have slow, lingering foreplay, with lots of kissing and caressing. Slowly undressing to our lingerie and then becoming more intimate from there. I would love it if the wife/GF watched and encouraged us, or suggested what we do to each other. I’d be okay if she just watched, or wanted to get involved as well.
Desires, Dreams & Discoveries: Michelle’s Journey in Feminine Expression
An Intimate Conversation About Fantasy, Reality, and Self-Discovery
In our latest deep dive into the world of crossdressing taken from my survey, I meet Michelle, a GenX regular crossdresser who shares her intimate journey with remarkable honesty. From childhood discoveries to mature realizations, Michelle opens up about her experiences, desires, and the delicate balance between fantasy and reality.