Sophia’s Story
Tell me about yourself.
My name is Sophia, I am a GenXer and a monthly crossdresser. Growing up in Australia I was closest to my mother and as Sophia, I am still, at heart, attracted to women.
If we could share sexual experiences and fantasy, what would that look like?
I am curious about exploring my sexuality more. This extends to being in intimate surroundings with a woman, dressed as Sophia, and just enjoying that experience and to see how we both feel. I also am interested in enjoying situations with a woman, myself as Sophia and a man and to see what transpires and how we all feel. It is for me almost enjoying my sexuality as Sophia, whatever that might be. I love being a woman and being out with a woman, engaging conversation and sisterhood.
What is your favourite colour and textures to wear?
Black, satin and lace. I have mostly black clothes as I have been focused on going out dressed, in the evenings and in a more sensual scenario. But now I wish to widen the colour pallet I use to dress. The materials is about feeling feminine but sensual at the same time. Softness of feel is important to me. I nearly chose nylon as stockings and suspenders are a must wear item for me and epitomise being a woman of elegance and sensuality.
Do you recall your first orgasm while dressed as a girl?
I think so. It was as a teenager. I enjoyed it and it was whilst dressed and masturbating to a Girlie magazine centrefold. It was exciting.
Do you recall the first time you had any sexual contact with someone, while dressed as a girl?
Yes. It was with an escort. It started with just wearing stockings, suspenders & stilettos in the bedroom with her. But over about 6 months, it evolved into me dressing up fully, having an evening out together and then being back in the bedroom for sexual fun. Again it was with an escort. They were very embracing of the experience as they are open minded. It was so enjoyable for me. I felt a woman, giving pleasure to a woman, as only a woman knows how.
Why do you think you crossdress?
I want to feel more like a woman and I do crossdress in public often, though I wish it could be more. It allows me to fully embrace my feminine energy. There is an element of wanting to surprise/shock people with it too. I feel better about how I look as a woman than I do as a man. There is a sexual enjoyment element to it also. The idea of shopping for clothes with a girlfriend is exciting.
What is your favourite fantasy clothing to wear and how does it make you feel?
Classic, stylish but sensual. Suits with pencil skirts, blazers with lingerie underneath. An absolute must have is sensual lingerie underneath with stockings (no hold ups) and suspenders with stiletto heels. Satin and silk blouses. Peplum skirts and dresses/jackets. Corsets & basques. I love the excitement of the sexy lingerie & stockings underneath my outfit and passers by having their heads turned and wondering what I am wearing under my outfit.
Can you describe your most vivid or exciting crossdressing fantasy?
To keep dressing up and going out in public.
In a non-sexual setting it would be going to a Black Tie Ball as Sophia. Walking down the runway as a model in a trans / crossdressing fashion show.
In a sexual setting, going to a high class swingers party with all the women dressed in a similar way to me, men dressed in black tie and this leading to a wild night.
What has been your most intense sexual encounter while dressed as a girl?
Going out with another sexy woman to a party and then back to the hotel with her. It was intense as the whole evening was about everyone being who they really were which opened up my mind to stop thinking in terms of genders and man and woman. But instead seeing everyone as a person, as them.
If a fairy godmother waved her wand and you could body-swap with ANY person in the world for 24 hours, who would it be and what would you do?
Dita von Teese. I would perform as Dita at Crazy Horse Paris & then have a high class drinks and an adult party at the Crazy Horse theatre back stage rooms. I would strut around all night in lingerie, stockings, stilettos and lace gowns.
What gender would you choose for your partner for an evening of fun?
A genetic girl. Though I would also enjoy with a trans woman too, though if I am honest. I am still not yet comfortable enough on my trans journey to be alone with a transwoman. Yet.
I am interested in other human conditions, like dyslexia or ADHD to see if there is a correlation with crossdressing?
I am prone to anxiety and have had depression. I certainly have thought about ADHD, even bipolar disorder (my Mum was bipolar). Chatting with my psychologist who knows me well, she is convinced I am not one of those. But I do show some of the signs of ADHD so would share your views about incidence in cross dressers – personally I think the link is a person wanting to be themselves, let their creativity break free and they have focus to try to achieve that and are restless unless they do.
What has stopped you going to the next stage of transition of your cross-dressing journey?
I enjoy at times, being both a man and a woman. If I fully transitioned I am fearful that being a woman every day would become monotonous and the excitement would go away. Interestingly when I have spoken with a few others in this space, I have never said to myself “I am in the wrong body”. That says to me I enjoy cross dressing and it is a real part of the true me. But I don’t see myself transitioning to a woman.
If you could go back in time and offer your younger femme self some advice, what would it be?
If you enjoy it, do it and be you. It is not binary, you may not be just a man or a woman. It totally depends on the context you are asking, at different times of your life, and you can fluctuate.
You can follow Sophia on Instagram and at her website at www.sophiaanderson.com.au/
Read more crossdresser stories: Vinny Anna (UK), Aanya (India) and more in the 2025 Crossdresser 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
Goodreads // Amazon Author Page
Other posts you may like...
Meet Tixxa, a Gurl After My Own Kinky Heart
Episode Ten: Sophia Anderson, Delightfully Delicious Lady From Down Under
Meet Layla, A Very Norty Gurl
Meet Veronica Vile: A Gen X Crossdresser on PVC, Public Play and Brutal Honesty
Meet Stella: A Canadian Crossdresser, Sissy and Switch on Marriage, Chastity and Connection