Stella is a millennial occasional crossdresser from Canada whose answers blew me away. She’s married, monogamous, and exploring her sissy side with a supportive wife who sometimes initiates “Stella time.” Her responses are loving, articulate, sexually candid and beautifully self-aware. Here’s her story, lightly edited from her 2025 Crossdresser Survey responses into a Q and A.
Stella’s Crossdressing Life: Sissy Identity, Chastity and a Supportive Wife
Q – Stella, give us a quick introduction.
Stella – I’m a millennial, an occasional crossdresser, and I dress about once a month. I’m based in Canada. Growing up I was closer to my father and I’m married, very happily, and my wife knows about this side of me and is doing what she can to understand, accept and support it.
Q – If we went out for the night and you dressed up for me, what would you want from the experience?
Stella – I’d love a girly night with someone I could fully trust and connect with. I’m pretty amateur at crossdressing, so getting ready I’d need a lot of help, but I think that would be part of the fun. A night out, which I haven’t done yet, would be exhilarating. Returning to a hotel room together to keep sharing the night sounds like the cherry on top. What exactly would we do? I don’t really know, but I’d be open to just about anything as long as we kept that sensual connection. Stockings would have to stay on for sure. The feeling of them sliding together is just too amazing.
Q – You mentioned red, but you wear a lot of black. Talk to me about colours and fabrics.
Stella – Red is probably my favourite to wear, but I do end up in more black. Purple and pink make it into the wardrobe a lot too. For materials, glossy nylons are too amazing, with lace, lycra and satin close behind. The feeling of anything soft and tight on the skin is so sensual. It hugs your body and makes any touch feel more intense rather than more dulled.
Why Stella Crossdresses: Marriage, Identity and “Stella Time”
Q – Why do you crossdress?
Stella – I want to feel more like a woman. There are a few reasons I love it. One, it’s a way to feel closer to what a woman feels like every day. Two, I just love the look and feel of the clothes, and there’s a part of me that wishes it was just OK for a man to wear a skirt, pantyhose and heels when he wants to. Imagine if at formal events and in the business world it was normal to see guys in that with a suit instead of pants. Look at Mark Bryan or Ray Deforest. Three, there’s a sexual thrill. I find women very sexy, so seeing myself dressed similarly is satisfying in that way. And four, it’s escapism. A chance to be someone without all the same responsibilities for a little while.
Q – Do you remember your first orgasm while dressed?
Stella – I only really started fully dressing up recently and started exploring my sexuality. I had a night with the house to myself. Got fully shaved, dressed, and prepped for some anal play. After enjoying being dressed and taking some pictures, I put on some videos and played along. I’m not into being with guys at all, but the idea of being with a sexy, sensual trans girl captivates me, so what I watch tends to be trans on trans or trans on cis girl. I imagine myself as the bottom in this fantasy.
I mounted my dildo and rode it doggy style, then changed position and rode it like cowgirl. Between the two I was right at the brink but couldn’t push over. It was so mind-blowing I could have stopped and felt satisfied. Eventually while still riding I started to play with my penis too, and had probably the most explosive orgasm of my life. The only one that rivals it was a similar night when I was wearing a chastity cage and used a wand on the cage while watching a video of a woman using a wand on her clit. I mimicked what she did until I went over the edge and collapsed convulsing.
Stella’s First Sexual Experience While Dressed
Q – And the first time with another person while dressed?
Stella – That was my wife. She and I are fully monogamous. Our relationship is great and I wouldn’t jeopardise it for anything fleeting. There was a long time when I was suppressing this side of myself, but in just the last couple of years we started talking about it openly. She made it clear she was supportive and even interested in exploring with me.
We had a night to ourselves. She suggested some “Stella time” (such a creative secret code, I know). We both put on lingerie, similar styles to each other but not quite matching, complete with stockings and heels. I added press-on nails, some light makeup, and was wearing a chastity cage that she had the key to. I told her I wasn’t to be unlocked until I’d matched the most orgasms I’d ever given her in a single day, or until she was at least satisfied.
I focused on her with my fingers and tongue first, then a strap-on. I never quite matched my old personal best, but she was happy. She decided she wanted to peg me, which was fine by me. We swapped the strap-on over and she fucked me doggy, then I rode her cowgirl, and the stimulation was almost enough to bring her another small one. She had enough and decided to unlock me. Once we started having “normal” sex it didn’t take long for me to go over, and thankfully so did she. We were both puddles, completely spent. It was awesome, we both want to do it again, and she was very surprised that long nails on her back were much more of a turn-on than she’d ever thought possible.
Crossdressing in Public: Stella’s Experiences Outside the Home
Q – You say you crossdress in public sometimes. Tell me about that.
Stella – I should clarify, I’ve only partially dressed and left the house to walk the dogs. Skinny jeans or a skirt with a normal top and block-heeled boots. Usually early morning before work, on the back trail behind my house where there isn’t really anyone around, so it’s a bit of a cop-out to call it dressing in public. I’d love to find an event one day where I felt comfortable going out fully dressed, probably as part of a date night or weekend with my wife.
Q – What’s your favourite fantasy clothing?
Stella – I’m torn. The mature side of me is in love with the look of a woman in a skirt suit. The combination of power and sexiness it exudes is incredible. The immature side of me longs for the whole clubbing aesthetic. Short skirts, ultra high heels, low-cut revealing tops. The kind of look that makes most people assume you’re out to hook up. Sometimes I just want to look downright slutty, which probably reflects how I’m feeling inside at the time.
Q – Tell me about your most vivid fantasies.
Stella – If you haven’t guessed by now, I lean a little into the sissy kink. I fantasise about being locked and controlled by a partner, maybe more than one. I’m not into degradation, but the idea of being kept solely for someone else’s pleasure is where I find mine. I want to be “mommy’s good little slut,” and I don’t think being a slut for someone you care about and connect with is degrading at all.
I’d be happy to be “forced” into fulfilling their fantasies. Only unlocked when they wanted sex that way. The sexual frustration used to push me to become more feminine, whether through working out, surgeries, tattoos and piercings. A tramp stamp would be an ultimate fantasy, though I already have my nipples pierced and recently got a PA piercing for chastity. Even being “forced” to have sex with another locked sissy, both of us using strap-ons. And not letting any cum go to waste, with cum kissing being a regular part of it.
Another fantasy is dressing up with other girls for a night out. Provocative outfits, a mix of trans and cis girls, locked in chastity with someone else holding my key. The night ends with an orgy where anything goes.
A third, very specifically centred on trans girls, is being dressed in lingerie and gangbanged by a group of them. The only rule is they all have to cum inside me.
The last is more identity. Part of me doesn’t want to fully transition, but would love to get vaginoplasty and continue living as male. I’d shift to presenting more non-binary, with feminine clothes as part of my regular wardrobe. Wearing panties exclusively, sometimes a skirt and heels, even thong bikini bottoms instead of board shorts to swim. I’d probably try my luck starting an OnlyFans if this ever became reality, lol.
Q – You’d swap bodies with your wife for 24 hours? Or someone else?
Stella – So many options. The safe answer, and one I’d still thoroughly enjoy, is swapping with my wife. I’d see what sex as a girl actually feels like while still being faithful to her. I’d also use it to show her some of the things I’d like her to do.
If I got a fantasy free pass, I’d swap with Robin Coffins, since she’s married to Sarina Havoc and they often film with other trans girls where she gets fucked by all of them. Pretty much my ultimate fantasy. Or Nicky Zeal, who’s in a relationship with Zariah Aura.
Q – And the object of someone’s desire for 24 hours?
Stella – A trans porn star. Top contenders would be Oriana Frost, Variety Itsol, Daisy Taylor, Mariana Cordoba, Lena Moon, Aubrey Kate, Khloe Kay. I could go on. Ultimately I think I’d go with Jade Venus.
Q – You suspect you have ADHD. Do you think there’s a link between ADHD and crossdressing?
Stella – I’ve never been diagnosed but I present a lot of the markers and people around me see them. I don’t know if there’s a correlation, but considering the sensory side and the higher rates of depression in high-functioning ADHD, it wouldn’t surprise me if dressing was a common form of escapism for people like that. A way to get out of your headspace and be someone else for a bit. The tighter clothes might also act like a comfort blanket and help calm the mind. Pure speculation, but it tracks.
Stella’s story is from my 2025 Crossdresser Survey. You might also love reading about Victoria, a German crossdresser with an equally supportive fiancée.
Q – One piece of advice for your younger femme self?
Stella – You’re OK as you are. People will love you no matter what. Just be you.
Stella, thank you. This is exactly the kind of honest, generous answer I hoped the survey would draw out. You can find her on Instagram @stella_xdress and on Reddit as u/Playful_Trade7671.
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
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