Meet Victoria: A Regular Crossdresser on Black PVC, Dominatrix Energy and a Fiancée Who Loves It

Why Victoria Crossdresses: Identity, Femininity and a Supportive Fiancée

Victoria – Overknee high-heeled boots, a push-up bustier, a ruffled bolero and panties that do amazing things to my ass, all in shiny black PVC. Sometimes I wear a long, elegant Morticia Addams style ballgown and corset over it. The whole thing makes me feel unbelievably sexy and powerful. After a few moments in the mirror I’m ready to either strut down the street or fuck someone’s brains out.

Q – Why do you crossdress?

Victoria – It sexually arouses me, but the reasons run deeper depending on my mood. I have an incredibly active mind, and crossdressing lets me step out of my own head for a while. It’s relaxing, centring. When I’m under stress or can’t get out of my head, I’ll just dress up and go about my day at home as a way to decompress.

I also enjoy the technical side. I put a lot of effort into creating a voluptuous, feminine figure. I’ve experimented with corsets, shaping tights, foam pads and silicone boob plates to get the best results. Makeup is a particular interest. I practise often.

But the biggest reason is simply that it turns me on. I always crossdress in front of my large mirrored wardrobe so I can see myself. Seeing myself as a gorgeous, sensual, sexy woman just does something to me that nothing else does. It also sends my confidence through the roof.

Q – Do you remember your first orgasm while dressed?

Victoria – It wasn’t unusual. My then-girlfriend, now fiancée, and I had got a bit tipsy and dressed me up on a lark. We both got turned on and we fucked. It was only afterwards, once I really started exploring crossdressing properly, that I unlocked a unique kind of passion that only comes when dressed, and noticed a different orgasmic experience.

Victoria’s First Sexual Encounters in Lingerie and PVC

Q – And the first sexual contact while dressed?

Victoria – Halloween during lockdown. We’d had a few cocktails and were tipsy, and she asked if she could dress me up. What the hell, I said. She did my hair and makeup, slipped me into one of her dresses, a corset, and a bra stuffed with socks. A real amateur job compared to my game today, but there was something magical about seeing myself as a girl for the first time. I got so turned on just looking at myself in the mirror and posing. My partner is more than a bit bisexual and she found girl-me very hot. We didn’t plan for it to go further than dressing up, but we couldn’t keep our hands off each other and ended up fucking. That night awakened the passion for crossdressing in both of us, and we both remember it fondly.

Victoria’s Most Intense Crossdressing Encounter

Q – Tell me about your most intense encounter.

Victoria – All of my sexual encounters while crossdressed have been with my fiancée. The most intense was a stay at a wellness hotel. I’d brought my crossdressing supplies as a surprise. One afternoon I emerged from the bathroom fully made up in a sexy maid costume. Her eyes went wide. I picked up a feather duster and started dusting the room, flashing my panties and shaking my ass and bulge in her face.

It wasn’t long before I felt her hands on my ass. I acted outraged and told her there was no groping the help in this hotel. Then I spun her around, ground my hard cock into her ass and said the help would be groping her instead. I kept grinding into her, fondled her tits, got her clothes off and fingered her until she was hot and needy. I pushed her down on the bed, took my cock out of my panties and mounted her from behind. I kept spanking her for trying to grope the help and she kept begging the maid to fuck her harder. When we both came it was the most intense we’d ever had. We both lay on the bed gasping. Too exhausted to do anything more than cuddle for nearly half an hour. We still reminisce about it years later.

Q – You have a whole library of fantasies. Hit me with the highlights.

Victoria – I do, across a whole spectrum.

In one I’m in full domme outfit and I dom the hell out of my girlfriend. Collar around her neck, remote-controlled vibrator in her pussy. She kneels and begs to take my hard cock out of my panties. She sucks me off until I cum in her mouth, all while I tease her with the remote. Then she’s on all fours and I fuck her from behind facing the mirror so we can both watch.

In another I play her little sissy bitch. Frilly pink lingerie, matching collar, blonde wig. She brings out her big pink strap-on. She bends me over and puts a remote-controlled vibrating buttplug in my ass, then I kneel and give her a sensual blowjob while she controls the buzzing and I moan like a little bitch. Finally she pegs me while stroking my cock.

Another is a wedding-night roleplay. I’m in a beautiful white wedding gown, she’s in a pants suit. Sweet and innocent as she takes off my dress to reveal white bridal lingerie. But when she gets to my panties and feels my big hard bulge, I get dominant. I send her to her knees, sucking off her bride.

Other fantasies include a sexy photoshoot that turns x-rated, my girlfriend dressing me up and bringing in one of her girlfriends with strap-ons so we cycle through who gets double-teamed, and a high school roleplay where I’m the gothic queen bee and she’s the new girl looking to get in with my clique.

The wildest one is purely imaginative. A foursome with crossdressed-me, guy-me, and two versions of my girlfriend, one with a strap-on. The hot scene is crossdressed-me and strap-on-her fucking sub-her and guy-me doggy. The bottoms make out, the tops show off their fucking for each other. So very hot.

Q – Body swap with anyone for 24 hours, who and what?

Victoria – A trans pornstar like Jessy Dubai, Mia Isabella or Aubrey Kate. I’ve always fantasised about having a true woman’s body, but those fantasies have always involved keeping my male genitalia. I’d invite a bunch of girls over, both trans and cis, and spend the day alternating between dressing up in pretty outfits and fucking everyone’s brains out. I’d top most of the time, but I’d also take the chance to bottom to a transgirl, something I’ve always wondered about but never tried.

Q – And the object of someone’s desire for 24 hours?

Victoria – A pair of blonde bombshell genetic girl twins. Identical, big tits, hourglass figures. I’ve always had a thing for twins. I’d fill the day alternating between girly activities (doing each others’ nails and hair), having them serve me as sexy maids (bringing snacks and blowing me while I play video games) and fucking both into oblivion. Plus a sexy photoshoot that turns x-rated. All in full girl mode.

Victoria’s story is part of my 2025 Crossdresser Survey. You might also enjoy Stella’s story of a Canadian crossdresser with an equally supportive wife.

Q – You have ADHD. Do you think there’s a connection with crossdressing?

Victoria – I was diagnosed at 10 and medicated through high school and college. I’ve learned to accept and enjoy my different way of thinking over the years.

Crossdressing definitely helps me get out of my head during periods of overactive thought, and it’s one of my go-to dopamine sources. I also find it a fun and convenient target for my hyperfixations. Just working at making my game as good as possible.

Q – Advice to your younger femme self?

Victoria – Don’t be afraid to tell your girlfriend you want to fuck while crossdressed or dress up around the house. She’s totally into it. Splurge on the good stuff. It’s better than buying cheap stuff you’ll replace before long. And please, please remember to take pictures. I get so transfixed and turned on by myself in the mirror that I often forget until I’m exhausted and ready to take everything off.

Victoria, thank you. So much detail and sensuality in your answers. A real treat to read.

Gurls, drop your thoughts in the comments. And if you haven’t done the survey yet, get on it.

Jenny xx