Vinny Anna is a Gen X regular crossdresser from the UK who dresses daily. Her answers are warm, specific and beautifully written, with a story about a first time with a transwoman that’s both tender and properly hot. Here’s her story, lightly edited from her 2025 Crossdresser Survey responses into a Q and A.
Q – Vinny Anna, give us a quick introduction.
Vinny Anna – I’m a UK, Gen X, a regular crossdresser, and I dress daily. Satin and lycra are my favourites as satin feels exhilarating against the skin and so ultra feminine, and lycra clings to every curve and leaves little to the imagination.
Q – If we went out for the night, what would you want from it?
Vinny Anna – Just girly time, chat, friendship fun. If it’s our first meeting it would be lovely for it to be informal. If we get on or decide to be more intimate, we can go from there. Or we may decide to go hunting together for others to join us.
Crossdressing Origins: Early Memories and First Experiences
Q – Do you remember your first orgasm while dressed?
Vinny Anna – I started wearing tights at a very young age, probably about nine. I really enjoyed the feeling on my legs and constantly stroked them and rubbed them against each other.
The first orgasm came a few years later. A girl at school was wearing red ribbed tights. I went shopping on the way home for the same style, ran up to my room, put them on, and made a complete mess pretending to be my classmate. As a youngster you can imagine how it felt looking down and seeing the copious cum all over the red tights. This naughty crossdresser then licked up her dirty mess and nearly orgasmed again.
First Sexual Encounter While Dressed: A Night with a Transwoman
Q – And the first sexual contact while dressed?
Vinny Anna – I met a transwoman online who lived locally. We got to know each other, then she invited me round to hers. I was wearing a pair of Wolford tights beneath my trousers, as I always did, and a pair of knickers. One thing led to another and we ended up in her bedroom.
I knew she was going to find out what I was wearing, so I explored her body first. Her cock was the first I’d played with that wasn’t my own. I stroked her erection and sucked her lovely long cock, then she wanted to return the favour. She seemed a little surprised to find me wearing tights, but she was open-minded about it. I’d like to think it got her a bit harder.
She played with my erection and we kissed and cuddled until she got on all fours and offered me her rosebud. How could I resist? After a little lubrication, I entered her and made love to her while playing with her little boobs and her not so little erection. The feeling of my nylon-covered legs against hers was as erotic and exciting as I’d always hoped it would be.
After a few minutes I withdrew and rolled her on to her back so I could see her pretty face as we made love. I re-entered her and she held me tight. I’d love to say I lasted for hours before filling her with my cum. In reality it was probably only a few minutes before my cock was shooting its load into my new lover. How did it feel? Amazing. How did she react? I think she enjoyed herself too.
Why Vinny Anna Crossdresses: Femininity, Freedom and Fabulous Legs
Q – Why do you crossdress?
Vinny Anna – Honestly, it relaxes me. The clothes are more interesting and varied. I like seeing attractive women in sexy clothes, and if I say so myself, I have a great pair of legs. I enjoy seeing a cute body with sexy legs looking back at me in the mirror.
I don’t go out in public because my facial features are very masculine. Not many women have a full beard. So I don’t present as a woman, but why can’t men wear a nice fitted skirt, a pair of expensive tights and knee-high boots in public? Why should only women get to enjoy a cool breeze blowing up their flowing skirt? In a parallel universe I hope there are places where men and women can wear whatever they like.
Q – Talk to me about your favourite fantasy clothing.
Vinny Anna – Although I don’t often wear latex or PVC, the first time I walked into a specialist shop it was so exciting. The staff were incredibly polite and helpful. They let me browse before asking if I was shopping for myself or someone else. Answering “for me” was very liberating. They offered to help me try things on. I felt brave for not running out, though I declined the offer for help in the changing room. I walked out with a green semi-transparent latex catsuit in my bag.
Q – Tell me about your most vivid fantasies.
Vinny Anna – My fantasies fall into two categories.
The first is fooling around with another crossdresser, transvestite or transwoman. Wide ranging, always consenting, always among friends. We start anywhere, work, a bar, a wedding, a holiday, and end up filling each other up in all available holes with cum before falling asleep together in bed.
The second is going to a bar with a friend of any gender while presenting as a woman, and picking up men for our pleasure. Drinks, dinner, intimate dances feeling their hardening bulges against my belly or between my cheeks. My hand wandering between their thighs as they come in for a kiss. Letting the hunks carry me to bed and make a woman of me. Walking home without my knickers, their cum dribbling out of my hole, over my stocking tops and down my thighs.
I also have a one-off fantasy of two transsexual sisters seducing me and one of them marrying me. Once married, I wake up with huge breasts and live life as the wife of one of the sisters, until they eventually decide one of the three of us no longer needs a cock and should have a vagina. They vote that I should have the sex change.
A Night Out at Pink Punters: UK Crossdressing in Public
Q – Most intense encounter?
Vinny Anna – The transwoman I mentioned earlier persuaded me to go to my local trans-friendly club, Pink Punters, dressed in a short dress, fishnet tights and knee-length boots. She helped me look presentable, and in we went.
We’d been a couple of times before, so I knew I wouldn’t be the most obvious transvestite, but I was still nervous as hell. We danced, had drinks, spoke to a few of the girls in the ladies’ toilets, a first for me, and had a great evening. The taxi home was exciting too. The obligatory kissing and cuddling, the driver watching us in his rear-view mirror.
I’d love to say we made love for hours when we got home, but I’d been so horny for hours that I didn’t last long. It was also the first time she made love to me, so a couple of firsts that night.
Q – Body swap with anyone for 24 hours?
Vinny Anna – It would have to be a trans pornstar with a curvy body and a fully functioning, large cock. I’d spend the day making porn films with other transwomen, with men, with women.
But most importantly, I’d like one of my co-stars to be the real-world me. I’d take that shy young man, seduce him, fuck his tight virgin arse, then get him to dress up as an attractive woman and show him off to the world. After capturing it all on film, we’d pick up a married couple and have a night of passion. No holes barred.
Q – And the object of someone’s desire for 24 hours?
Vinny Anna – Not a specific person, but I’d love to become the plaything of a transwoman who wants to take an innocent pretty boy and turn him into her perfect fantasy figure. Just dressing me up would be fine. As a French maid, good. As a rubber sissy maid, great. If she wanted to turn me into a big-breasted slut that would be amazing. And if my pathetic little cock was replaced with my own vagina, that would be the best ever.
Q – Evening dressing up with anyone, who?
Vinny Anna – Probably Nikki Nicole. We have an online friendship so I know what she likes. It would be an interesting evening just to sit and chat about our interests with no pressure of anything sexual. But if it happened, icing on the cake.
Vinny took part in my 2025 Crossdresser Survey. If you haven’t shared your story yet, I’d love to hear from you. You might also enjoy reading Veronica Vile’s story, another wonderfully honest UK-based crossdresser interview.
Q – Advice to your younger femme self?
Vinny Anna – Go for it, girl. And keep exercising.
Q – What’s your biggest regret, or what do you wish you’d done early in life that you didn’t do?
Vinny Anna – When my girlfriend found out I liked to dress up, I should have actually dressed for her. It could have ended the relationship earlier, or perhaps brought us closer together.
Vinny, thank you x. The Wolford detail, Pink Punters, the whole tone of your answers, pure UK crossdresser royalty.
You can find her on Flickr at the handle she gave me, @92544799 on the NSFW account.
Gurls, drop your thoughts in the comments. And if you haven’t done the survey yet, get on it.
Jenny xx
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 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
Meet Victoria: A Regular Crossdresser on Black PVC, Dominatrix Energy and a Fiancée Who Loves It
Meet Aanya: An Indian Crossdresser on Sarees, Sissy Femininity and the Housewife Fantasy
Meet the gorgeous Sophia from Australia