Woman in a black dress sits on a chair beside a wooden desk in a room with patterned wallpaper.

Part 4: Who Would You Love To Spend Intimate Time With?

So this one is an intersting one...

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.

As such, I find some labels rather unhelpful. They feel, well binary. Too specific.

By means of example, I am very much heterosexual with a very, and I mean VERY strong sexual trigger around feminine clothes. I adore playing ‘the girl’ in the bedroom. 

But I only want to be with Genetic Girls. As such I adore the term Trans Lesbian. Thats who I want to be. To look like a girl. To dress like a girl. A slutty one at that. To be a lesbain with other girls. Genetic girls. That is my desire. A specific an unwavering fantasy.

Or is it?

I recently did some pretty deep soul searching and came to realise that my firm Genetic Girl boundary, was in fact, flexible. And in fact very flexible. This came to me after I did my podcast with Jennifer Lunden and realised that yes, I would enjoy making a film with her. And she is trans and outside of my (what I thought were) rigid boundaries. 

Eeeeek! I mean I am happy about this. Secretly excited. But yes. Eeeeek!

I do think much of my personal thinking is generational, being a GenXer. Younger folk seem way less stuck inside systems built by the elders who passed before them. But similtanesouly, and perhaps paradoxically, they are also more concerned with labels and expression of identity in a very specific way. Perhaps we were all more this when younger. Probably.

May take? Do you. You are perfect as you are. Just do you. Fully.

OK. So this question goes to the very heart of WHO would we spend intimate girl time with, if we had no barriers.

Who Would We Love To Spend Time Dressing Up With Most?

A genetic girl
43.60%
I don't mind, any and all
24.70%
A trans girl
23.78%
A man
7.01%
I would stay on my own
0.61%
A trans man
0.30%

It’s clear, we adore feminine energy, appearance, company and playtime. I am very much at the far end of that with my deepest desires being shared with genetic girls. Though I have concluded I would also enjoy time with femminine trans women too.How about you? Please do leave comments.

Two women with makeup pose closely. One has blonde hair with a red bow; the other has long brown hair with a shaved side.

Those who chose to spend time with Genetic Girls

‘I Just want time with someone who finds crossdressing fun and erotic.’

Laura (GenX, Occasional Crossdresser)

‘My girlfriend, she has been so supportive since I told her and she chooses my lingerie every day, holds the keys to my cage, and wants me to go further.’
Ellie (Millennial, Sissy)

‘I just want a girl that is into crossdressers.’
Jenn (Boomer, Regular Crossdresser)

‘I want a dominant genetic girl to serve and become her cuckold.’
Kelly (GenX, Trans, but choosing not to fully transition)

‘I have some girlfriends who I wouldn’t mind dressing up and hanging out with.’
Brooklyn Paige (Gen Z, Regular Crossdresser)

‘I think it goes back to wearing my girlfriend’s panties, but we didn’t get to play around except her hand on my lap.’
Lacey (GenX, Occasional Crossdresser)

‘There are so many beautiful women. I would love Lily Collins. She’s so pretty and fashionable.’
Holly (GenX, Occasional Crossdresser)

‘I feel like I’d be better off with someone with experience.’
Eska (Gen Z, Sissy)

‘She’s a porn star ahnd we could do girl-on-girl. Dressing up and chatting would be a fun evening.’
Amber (GenX, Regular Crossdresser)

‘I would love a woman who enjoys taking the lead in the bedroom. Complete with a strap-on.’
Jennifer (Boomer, Regular Crossdresser)

‘I would love to be coached by a woman. My dressing has been self-taught in the closet. I’d love to get some pro advice and guidance.’
Amanda Harriman (GenX, Occasional Crossdresser)

‘My wife—she indulges me a couple times per year… I wish it were at least once per month.’
Melissa (GenX, Occasional Crossdresser)

‘An attractive young woman who wears short skirts and is sensuous.’
Katie (Boomer, Regular Crossdresser)

‘Girl energy, MORE GIRL ENERGY please! I am most connected to my actual girlfriends who I know most intimately. As we have all grown up, we have got more sensible, so to go back and revisit those times with them would be amazing.’
Jenny Raven (GenX, Regular Crossdresser – and yes that’s me!)

Three women pose against a dark background, with the woman in the center in focus and the other two blurred in the background.

Those who selected 'I don't mind, any and all'

I don’t care about gender. I just would love a supportive friend that will push me to go after this thing that I want even though I get nervous or scared or second-guess myself.
Cami (Gen Z, Occasional Crossdresser)

Some women are very attracted to me when I’m dressed in femme and that’s a big turn-on. Wife won’t allow that, but it would be fantastic. Of course, my sex role would be a top in that case. With a man or trans woman that is too functional, I would be allowed to be the submissive role.’
nan (Boomer, Regular Crossdresser)

‘I would be with friends who I can rely on to style me up and to dress up together. It doesn’t matter about their gender.’
Haley (Gen Z, Sissy)

‘I’m very open, it would be so fun to dress up with anyone who was interested in playing. I’d love to wear a beautiful woman’s clothes and serve her any way she wishes.’
76starships (GenX, Occasional Crossdresser)

‘Just a random person outside to have some sexual fun with.’
Helene (Boomer, Sissy)

‘Anyone who accepts me would do, probably.’
Leonieblnbi (Gen Z, Regular Crossdresser)

‘I have no one yet.’
Lexi (GenX, Trans and wanting to transition)

‘My first thought was a genetic girl, but then dressing up for a man might be lots of fun.’
Brandi (Boomer, Regular Crossdresser)

‘Literally happy to spend the evening with anyone.’
Beth (Gen Z, Trans and wanting to transition)

‘It doesn’t matter who it’s with. I enjoy playing dress-up with anyone.’
MommaSamantha (Millennial, Occasional Crossdresser)

‘I just like being girly, and if the other person is up for it, then I will be happy with all of them.’
Janet (Gen Z, Sissy)

‘I don’t have any preference, I just want friends.’
JAMY LYNN (GenX, Regular Crossdresser)

‘I want to dress up and have people tell me how pretty I am.’
Rebecca (GenX, Occasional Crossdresser)

‘If they liked me dressed and would help me and we could have fun, I wouldn’t care who it was.’
Britney (Gen Z, Occasional Crossdresser)

‘I dress up every day and every night. When I get new items, my housemates (including my boyfriend and girlfriends) are very honest about how things look on me and how things go together (or not).’
Ash (Millennial, Regular Crossdresser)

‘I’m down for whatever and enjoy all types.’
Julia (Millennial, Occasional Crossdresser)

‘Being bisexual/pansexual, I enjoy all the genders and in between. The only things I need are mental and physical attraction.’
Bree Zee (GenX, Sissy)

‘I’m not selective per se. I’m attracted to personalities first. Of course, there has to be proper hygiene involved.’
Lola (GenX, Trans, but choosing not to fully transition)

‘I am technically genderfluid but have considered whether or not I’m trans at some point. I would want to dress with both genetic and trans women, but trans women might have a bit more in common with me.’
Gail (Millennial, Other)

Two women in elegant robes and lingerie, seated with glasses of champagne in a dimly lit, smoky atmosphere.

Those who selected 'A trans girl'

‘I’d like to have some fun with Natilie Mars as she is someone with lots of experience and could give me pointers on how to be more girly and sexy.’
Melissa (GenX, Occasional Crossdresser)

‘I’d love to share an evening with a trans girl.’
Gail (Boomer, Admirer)

‘I would love to spend the day (evening) dressing up with a trans woman who I follow on social media and have the biggest crush on. I would love to play dress-up with her and try on different outfits and footwear and then afterwards have some intimate fun.’
Emily A. (GenX, Occasional Crossdresser)

‘I’m only sexually attracted to people presenting as female… genitals are irrelevant.’
Michelle (GenX, Sissy)

‘A trans girl because I love serving women and would love them dressed like me but also able to relate to me with a bulge in pants.’
Jessica (Gen Z, Sissy)

‘Probably because she has more experience in looking passable. But I would love to just dress up with any woman.’
Jennifer (Gen Z, Occasional Crossdresser)

‘A trans girl has the knowledge and experience of dressing and becoming a woman.’
Donna (Millennial, Occasional Crossdresser)

‘I love a girl with breasts and a penis.’
Katie (GenX, Regular Crossdresser)

‘Femininity is everything to me, and a trans girl appreciates every morsel of it since she’s had to choose it and work to get it.’
Heather (Millennial, Sissy)

‘Ideally with a genetic & trans girl, for a three-way. But also to fully experience being a girl myself.’
Natalie (Millennial, Regular Crossdresser)

‘I think the perspective would be interesting.’
Ariel (GenX, Regular Crossdresser)

‘I find trans girls and crossdressing men to be FAR more feminine and sexy than CIS women today. T girls and CDs are more open, receptive, and less judgmental of men. And they are not in competition against men nor do they hate men as much.’
Samantha (Boomer, Admirer)

‘Just something so sexy about a trans girl. Just got a lot to play with.’
Ariah (Boomer, Occasional Crossdresser)

‘Sharing similar interests and coming from the same background. No particular person in mind though.’
Naomi (GenX, Occasional Crossdresser)

‘I would definitely want to dress up with either a genetic girl or a trans girl. I am not attracted to men, so dressing up with another girl is just sexier. Dressing up with a trans girl is just a little more exotic, and if things turn toward having sex, it is something that I have never experienced. I know all of this makes it sound like I am fetishizing trans girls, and maybe on some level I am. I just like to please my partner during any sexual activity, and if she has a penis, it just seems easier to do if I am bottoming.’
Stella (Millennial, Occasional Crossdresser)

‘I would love to be with a trans female, the best of both worlds—breasts and a penis. There is nothing better than that.’
Jasmine (GenX, Sissy)

‘Want to make pretty and at the same time serve. So make the perfect beautiful girl who would tell me what to do and kneel.’
Ariana (GenX, Sissy)

‘I just love girls with dicks.’
Sarah (Gen Z, Sissy)

‘No one specific again, but I’d feel more comfortable with a trans girl or CD.’
Michelle Cox (Millennial, Occasional Crossdresser)

‘Just any of the sexy gurls I have met. I just find crossdressers fascinating. I’m assuming a CD is classified as trans.’
Dianne (Boomer, Occasional Crossdresser)

A man reclines on a bed, shirtless, in the background. In the foreground, a close-up of a woman wearing white lace underwear is visible.

Those who selected 'A man'

'I have been flirting with a guy on FetLife, Christopher. I have grown to trust him. I would love to dress up for him.'
Misty (GenX, Occasional Crossdresser)

‘No one in particular, just a normal nice man.’
Chloe (Post Boomer, Regular Crossdresser)

‘A daddy.’
Gina (Gen Z, Sissy)

‘I prefer to put on a fashion show for men.’
Brinah (GenX, Regular Crossdresser)

‘My partner. He supports my femininity and loves who I am.’
Brittany (GenX, Sissy)

‘A crossdress friend I met online in a contact website. He’s in his twenties, so less than half my age, and lives at the other end of the country. We’ve both sent each other detailed fantasies of what we’d do if we ever got together. We would treat each other to every conceivable method of pleasure, including handjobs, blowjobs, swallowing cum, sharing a double-ended dildo, and fucking each other.’
Katya (Boomer, Occasional Crossdresser)

‘Any good-looking, well-hung man.’
Jackie (Boomer, Regular Crossdresser)

‘It’s a chat friend. He understands me as a woman and treats me appropriately. He has always been respectful and only knows and thinks of me as a woman. He doesn’t want to know my male side. Our chat has always been plain vanilla, but recently, he has been getting more provocative. Not crude, but a bit naughty and suggestive. Quite frankly, it’s so psychologically stimulating—he really understands the gurl me. Dare I say, he turns me on as a woman.’
Sheryl (Boomer, Regular Crossdresser)

‘No specific person… just a gentleman that would look at me as a female.’
Flora (Boomer, Trans, but choosing not to fully transition)

‘No one in particular, a hung dominant to thrill me.’
Paula (Boomer, Occasional Crossdresser)

‘I picked a man because this is something I haven’t really done, but I do spend many nights with a genetic girl. But, to be honest, I would probably spend time with anybody in your list, if the vibe was right, attraction was in the air, and we all wanted similar things.’
Vanessa Nines (GenX, Regular Crossdresser)

I want to feel like a real obedient girl to a strong and sexy man, loving me and enjoying me.’
Lady C (Boomer, Occasional Crossdresser)

Person in lingerie and lace mask reclining on an ornate sofa in a dimly lit room.

My Analysis Of The Comments...

Who’s Your Dream Date? A Crossdresser’s Guide to Desire Across Generations

Who is that special someone? Is it a soft, sensual genetic girl? A fierce and fabulous trans goddess? A strong, commanding man? Or are we open to any and all who adore us in our feminine glory? Let’s slip behind the velvet curtain and see what our sisters are whispering about in the dressing room…

And gurls, remember these are trends. Leanings. Not absolutes. And there is 1% of who who favour trans men or being alone. Not a massive percentage BUT a whole heap of lovely people nontheless. So let’s remember, this is 1990’s girlie mags analysis, and NOT scientific.

Generations & Their Desires: Who Are the Girls Chasing?


💋 Boomer Bombshells: These seasoned vixens tend to favor the strong, masculine energy of a man. There’s something about surrendering to a confident gentleman who sees them as the divine feminine they aspire to be. But they also have a deep appreciation for genetic women—especially those who can guide them into softer, more sensual femininity. However, don’t be fooled—some Boomers are adventurous, openly expressing their fascination with trans women, craving both shared experience and a touch of the exotic.

💋 GenX Glamour Dolls: Oh, my love, GenX gurlies are all over the map—and we adore that about them! These girls are the ultimate mix of traditional and exploratory. While many adore the timeless romance of a genetic girl, others fantasize about the forbidden thrill of an intoxicating trans beauty. They also have a particular penchant for “a man who sees me as a real woman,” longing for that deep validation that makes them feel like the ultimate vixen. GenX girls are also among the most playful, with many embracing “any and all” possibilities, as long as they can revel in their femininity.

💋 Millennial Minxes: Now, these kittens are curious and experimental! While Millennials love a fellow crossdressing bestie to twirl with in the mirror, they also have a huge soft spot for trans women. Maybe it’s because they see them as kindred spirits? They’re also highly drawn to men who treat them like ladies—but only if he knows how to worship a crossdressing goddess properly. Many Millennials are pansexual in their fantasies, open to any gorgeous soul who makes them feel radiant and desired.

💋 Gen Z Sweethearts: The youngest girls on the scene are fearlessly fluid. They are the least likely to lock themselves into just one preference. Many simply crave a connection—someone who makes them feel pretty, special, and adored. While they still appreciate a genetic girl’s nurturing energy, they are also deeply intrigued by the idea of a trans girl or a dashing man sweeping them off their perfectly nylon stockinged feet. They’re adventurous but also soft and romantic—the best of both worlds, really!

Crossdressing Frequency: How Often You Dress Affects Your Fantasy


💄 Occasional Crossdressers: These flirty dolls are dreamers, often fantasizing about the experience more than living it. They tend to romanticize genetic women as their ideal partners—someone to teach them, guide them, and embrace their delicate femininity. But oh, gurls, they also harbor hidden fantasies about being swept away by a dominant man or a sultry trans girl who knows exactly what she’s doing. Being desired and having someone take the lead is important.

💄 Regular Crossdressers: These confident queens have a more grounded approach to their desires. Many have already experienced dressing with a girlfriend, a trans mentor, or even a partner. They know what they like and often lean toward intense connections—whether it’s with a strong, assertive man, an equally feminine trans woman, or a playful mix of both. They crave experience over fantasy and are more likely to chase what excites them in real life.

💄 Sissies & Submissive Souls: Oh, these girls know exactly what they want—a man to take charge! While some adore the idea of dressing up with another crossdresser, most sissies dream of being pampered, dominated, and ravished by a strong, alpha male who calls them his princess or slutty slave. That being said, some of our sweet sissies also lust after trans girls—perhaps because they see them as ultimate role models of femininity with an added thrill.

Final Thoughts: What Does It All Mean?


If there’s one thing our little survey has revealed, it’s this—we are diverse, deliciously complex creatures—with desires that span across genders, orientations, and experiences. Some of us dream of a tender, girly sleepover with a genetic woman, swapping secrets and lip gloss under fairy lights. Others want to be owned by a strong, dominant man who whispers, “good girl” as we tremble in our lace ahdn heels, or taking a strap-on from a mistress. And then there are the fabulous divas who just want it all—the men, the women, the crossdressers, the trans beauties—because why should we ever have to choose?

At the end of the day, the most important thing is this—whatever turns you on, whatever makes you feel beautiful, and whatever lets you live your most divine, feminine fantasygo for it, and always in six inch heels and black lace top stokcings!

Now tell me, darlings—who’s your dream date? Comments below💋✨

In the next post...

Get ready for another deep dive into our naughty femminine sides.

Please do feel free to leave your own comments about these stats below and I will be sure to answer you.

JennyX

Meet real members of the 2025 crossdresser community: Vinny Anna who had her first intimate encounter with a trans lover. Explore the full 2025 Survey.

Explore The 2025 Whole Survey...

Two women smiling in a vibrant, neon-lit club setting at night. They have long dark hair and are wearing stylish outfits and hoop earrings.

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.

Read More »
Women’s lingerie and high-heeled shoes scattered on a blue wooden floor, including bras, panties, stockings, and heeled sandals.

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.

Read More »
Person in a grey suit sitting in a leather chair, with one hand on their head, looking to the side.

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.

Read More »
Two women wearing sunglasses and holding shopping bags smile at each other while standing outdoors in a brightly lit area.

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.

Read More »
Person in a black dress and white heels is lying on a couch, holding a bottle of opened champagne with a cork in mid-air.

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.

Read More »
A woman in a flowing pink gown, adorned with a crown, dances gracefully with a wand amid swirling pink petals against a mystical, cloudy background.

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.

Read More »
A person in a ruffled dress sits on a ledge with their hands on their lap. They are wearing sparkly high heels.

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.’

Read More »
A woman in a black dress and high heels lounges on an ornate, beige tufted sofa, set against a dark background.

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…

Read More »

8 thoughts on “Part 4: Who Would You Love To Spend Intimate Time With?”

  1. Jenny; I like as you are without bias, and I prefer all models the same respect. I prefer conversation over intimacy as a practice upon any and all women alike as a best practice of respect. The inter emotions of expressing HSP and ESP upon contact is to high. I say this to you, because I feel you to know the same.

    Best expression

    I see you; William

  2. Dear Jenny,
    Thank you for including me and sharing your survey. It gives me chance to look beyond my small world and see so much more. Your survey is a wonderful chance to share things I never share with any one. Thank you again. Take care and be safe.

    Mary

    1. Thank you Mary, I really appreciate your words. One big part of the joy of this survey has been connecting with so many amazing gurls, reminding me that not only am I not alone, but also I am not, like you, remotely unusual. We are all part of wider community on a many intersecting spectrums and I am loving exploring them all.

  3. Dearest Miss Raven,

    Thank you so much for including me in your posts. I don’t get to open up about my gurlie self very often and sometimes I don’t always fully share what I like/want etc. However, I am glad I found your site and audio books which I love the journey of those I’ve listened to. Looking forward to the rest of the results. Be safe and take care babe. And once again thank you, Miss Raven

    Regards
    Daisy Jenna

    1. Now Daisy, you and me, we are gurlfriends, so none of this Miss Raven, it’s Jenny to you. And I am honoroured that you shared yoruself with us all. It was a delight to get to know you through your words, and the world is that much brighter for your sharing of yourself. You are brave and sexy. And of course, look fabulous in heels!
      Kisses, your gurlfriend, JennyX

      1. Aww bless you always Jenny! And yes, you are right that we are gurlfriends! It was an honour to share myself with you, Jenny, and hope to share more of ourselves in the future. Hope you have a lovely valentine’s, that’s if you have anything planned gurlfriend ;)

        Kisses to you in heels and thongs babe
        Daisy Jenna
        X

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