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Interview with Fabulous Crossdresser JESS KELLY

Interview with Fabulous Crossdresser JESS KELLYJess Kelly is a fabulous crossdresser from Bristol, UK. We had a lovely opportunity to take her interview and talk about her crossdressing journey.

Q. Tell us a bit about yourself, your hobbies/interests & where you are from?
Jess: “I’m Jess, a 32 year old genderfluid crossdresser, living in Bristol, UK. I’ve been dressing up on and off since my late teens, though would say I’m very much “on” these days! In my spare time, I play bass guitar in a hard rock (possibly “soft metal”) originals band called Dead Rubber Dolls (check us out on Spotify *wink wink*​), I’m learning to speak Japanese, I play D&D (more specifically, I run a homebrew game as Dungeon Master), and I occasionally perform improv comedy on stage/at festivals. It’s actually a wonder that I get any time for dressing up as a pretty girl…”



Q. How did you get started with crossdressing?
Jess: “I imagine very similarly to how most folks got started – only wearing a few very basic items at first when I was a teenager, thinking it’d just be a phase that I’d somehow puberty my way out of! It wasn’t until I went off to University that I started realizing it was a little bigger than that and taking it seriously.”

Crossdresser in pink dress

“I bought my first wig, dresses and makeup, and it just kinda snowballed from there. I had a few friends at Uni who I let in on it, and they were all super lovely in letting me explore my feminine side around them, though that sadly all went firmly back in the closet when leaving Uni and moving back in with the parents. Once I’d moved out, though, I was able to have as much Jess time as I needed.”



Q. What are the challenges that you have faced as a crossdresser?
Jess: “I suppose initially feeling like I was the only person in the world who actually did this! Back in the day, the only social media platform I was on was MySpace (RIP) and there was hardly any positive representation on TV (it’s like, “hey, you can either be the butt of a joke in a lame sitcom/sketch show, or a serial killer”).

“Things are much better now (though we still have a long way to go with acceptance), so then after that my mind wandered to the natural “am I transgender?” question. “I don’t think I’ll ever fully 100% align with identifying as male, but I’ve also never outright hated my male side or felt so desperate that I need to consider transitioning or I’ll be forever suffering, as almost all transwoman seem to feel, so I’ve just learned to love having the bigender experience of both sides.”

Crossdressing in red dress and wig

“And yeah, if being upfront with women about this whenever I’m in the dating game means that they’re gonna be put off (I’m basically just resigned to being perpetually single these days), then that’s their loss, not mine!”



Q. What are the things that you really enjoy about being a crossdresser?
Jess: “I mean, what’s not to love?! When the outfit finally all comes together, usually as the wig goes on last, there’s no other feeling like it. You know it’s you in there, but you’re looking in the mirror at a beautiful woman, and you just immediately inhabit this entirely new persona and mindset. Like changing the kind of lens on a camera, or watching a different cut of your favorite movie!”

man transformed into woman

“I also love the almost limitless variety of different looks to try – while there’s comfort in finding a signature style, I’m also very much a “dip my toe into every kind of outfit” girl. That can mean something as simple as mixing up the hair, all the way to changing up the aesthetic or even doing full-on cosplay! More recently, since joining Instagram, I’d also say finding this community has been hugely rewarding and makes me feel a lot better about myself every single day, with all nice comments and messages I’ve been getting.”



Q. How often do you dress up now and tell us about your transformation/makeover process?
Jess: “Contrary to what my Instagram may have people believe, I only really dress up 2 or 3 times per month. That amount has fluctuated over the years (longest break was about 18 months), but I think it’ll hold pretty steady for now I’m in a comfy living situation. As for the routine, shaving tends to take anywhere between 1 and 2 hours, depending on how much I’ve let grow, so that’s the biggest time sink to account for.”

“After that, I’ll chill for a bit (most likely with food), whilst deciding on exactly what I’ll wear by laying it out on my bed, including what kind of breast forms/plate, jewelry, shoes, everything. Makeup after that takes between 30 minutes and an hour, depending on how complicated I want to go (or how much time I have left before a plan kicks in).”

crossdresser makeover

“I’ve got a transformation montage video on my Instagram, which I’m planning on sticking on YouTube soon for anyone interested. As for going for professional makeovers, I’ll generally do 2/3 a year, and that’s just a case of sitting back in the chair and enjoying being pampered!”



Q. Where do you buy your clothes & makeup from?
Jess: “Part of my quest to try every possible different look under the Sun means that I’m not particularly beholden to brand loyalty. If there’s a very specific kind of item that I’m after, I’ll generally go online – ASOS, Pretty Little Thing or Shein haven’t steered me wrong yet. The rest of the time, I’m down to just wander out to the shops (perks of living in the city centre) and pick up stuff that catches my eye.”

Crossdresser Jessica Kelly in black bodycon dress

“One thing I haven’t done yet, which is something of a bucket list/2023 resolution, is to actually shop while dressed up – part of me thinks I’ll just end up spending way more money that way, but it definitely could be a fun experience! There’s a few independent clothes stores near me that are the perfect balance of (1) not too busy, (2) not too expensive, (3) having a good range of styles, and (4) providing the smug satisfaction of supporting local business!”



Q. What type of activities do you prefer to do after getting dressed?
Jess: “For the longest time, it was literally just taking pictures to document the whole experience, so I’d have something to look at in my normal day-to-day life and remember that I’ve got what it takes to be beautiful! These days, I still take a lot of photos and videos, but where I can, I’ll try and do some other stuff too.”

“I’ve recently gotten into livestreaming on Instagram (shoutout to @nikki._.mirage for being my gateway girl), because it’s a great chance to hang out with other crossdressers (and admirers) like mates down the pub, talking about literally anything and everything. It’s definitely the sort of thing that I WISH we had back when I was a confused teenager. There’s some other stuff I’ll do when dressing up, but maybe I’ll save that for the next question…”



Q. Have you ever gone out in public in your femme self? If yes, can you share your experience about going out in public and being dressed feminine in front of other people?
Jess: “Oh, wow, funny you should ask! Yes, I’ve been out a bunch of times while dressed up. Done a fair few club nights with friends and other dressers (though not in the last few years, getting kinda desperate for a night on the town, invite me to stuff)! I’ve also been out during the daytime during Bristol Pride, and I’ve actually performed in girl mode, both in the band at some of our gigs and as part of an immersive theatre act at Boomtown Festival last year.”

crossdresser in red dress and heels

“I guess in each of those contexts, being dressed in a feminine manner in front of others can feel very different. Weirdly, it’s actually way less nerve-wracking when you’re performing, because there’s a natural “barrier” between you and the public.”

“For a night out or just being a girl on the town, though, there’s usually a little hesitation at first, but that generally melts away pretty quickly when you remember the fundamental truth – people either don’t notice or they don’t care! I count myself as pretty lucky that I haven’t ran into any trouble while out, and it always feels super liberating.”



Q. Any particular story or experience you would like to share about yourself and your crossdressing journey?
Jess: “It would be easy for me to suggest that my dressing up has been an entirely incident-free lifestyle, and that I’ve just somehow lucked my way into a smooth ride from the closet to fully out, but that would be disingenuous. As most have probably experienced, there were a few close calls with getting discovered early on (like the family coming home early, and hiding in the bathroom pretending to be having a “long bath”).”

Crossdresser Makeup Transformation

“Years later, once I started getting into the swing of meeting people in Uni, one other crossdresser, who I had chatted to online and invited over to hang out, stole a bunch of my stuff out from under my nose before dropping off the face of the Earth. I suppose my point is, despite incidents like these, I’ve still managed to end up in the happy place where I am today, and yeah, I may have a healthy amount of trust issues to work through, but things can always get better!”



Q. Have you come out to your friends and family as a crossdresser? If yes, how hard was it for you?
Jess: “I am fully out to everyone, or at least, everyone who pays attention to me! The process started a little over 10 years ago, telling a few close friends at University. As time went by, it became clear that it’s far easier to share with folks who you haven’t known as long. Telling my sister and my best friends from high school was the next biggest step, but they were all fantastic and supportive about it.”

man dressed as woman

“Next came the final big step, telling my parents – the plan was to tell them both, with my sister alongside for support, at the start of 2020. I managed to come out to my Mum but before I could talk to my Dad about it, a little thing called COVID-19 happened, and I was faced with the unappealing prospect of having the conversation whilst locked down over Zoom.” Still, I had patience, and waited until Summer 2021, where we were finally able to have the talk in person. After that, I just did a mass coming out post on my social media, and since then the cat’s been fully out of the bag!”



Q. What are some of your favorite outfits/styles?
Jess: “As a bit of a connoisseur of the full buffet that is “women’s clothing”, it’s so hard to choose any particular favorites! I enjoy wearing bodycon minidresses like all the cute girls would wear on Uni nights on the town, but recently I’m also finding myself more taken with styles that would work for a cocktail bar, a fancy gala or as a wedding guest. Classy and glamorous (most of the time)! And ideally showing off some amount of cleavage!”

Beautiful crossdresser

“I’ve dabbled in other styles, sometimes at professional makeovers, such as office wear, grungy./gothic and casual everyday wear, but I think it’s probably the bodycon dresses that I’ll keep gravitating back to. Outside of the outfits, I’m a sucker for full fringe haircuts, big chunky women’s watches and unnecessarily large hoop earrings – I’d be very easy to buy birthday gifts for!”

“If you want to see more of my favorite outfits, I actually went through a few of my looks a couple of years ago for this site:
My-5-favorite-outfits-style-with-jessica-kelly/” 




Q. Lastly, any tips or advice you would like to give to crossdressers who are just starting out?
Jess: “My main advice would be to just focus on your own enjoyment of dressing up! Don’t worry about comparing yourself to others you may see online, or think that by being a crossdresser, you are stuck on an inevitable path to become X, Y or Z.”

“Figure out what it is that you enjoy about it and then slowly build up your skills and wardrobe from there. There aren’t really any shortcuts to getting good at this sort of thing – you have to put in the time to hone your abilities, but you also need to be in a comfortable place to be able to relax and let your feminine side come through naturally.”

man to woman transformation

“Invest in quality products too, as cheap does not always mean cheerful (on that shameless segue, use code “JESS” to get 10% off at The Breast Form Store – https://thebreastformstore.com/ref/19. Finally, only you can know what crossdressing means to you, but that doesn’t mean that talking to others is a waste of time. Close friends and family will want what’s best for you, and that should always mean putting your happiness first!”

“Thanks very much again for the opportunity to share!”Jess Kelly

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4 Comments

  1. Great pics Jess ! You make a truly beautiful girl and you are an inspiration to all us other girls ! I am 57 and have been crossdressing all my adult life as Jennifer Anne. I am based in Birmingham uk.
    For any girls out there looking for support here in Birmingham check out the Trans Tea Room wich is held every Wednesday afternoon at Carrs Lane Church on Carrs Lane in Birmingham City Centre from 1.30 pm till 3pm . Its lovely there for Crossdressers and Trans Girls. You can chat and have tea and cake there and there are changing rooms there.

  2. Trans Tearoom takes place at Carrs Lane Church Centre wich used to be a Christian Bookshop at Carrs Lane Church in Birmingham.
    Lots of space there and you can buy Quality second hand Ladies Clothing there for just a small donation. Check it out !

  3. And for all you girls struggling with their make up I recommend a make up session at ‘Mac’ cosmetics in Birmingham wich are Trans Friendly or use the ‘Gender mode on ‘Faceapp ‘ app on the net.
    I use it to make me look like a convincing beautiful girl on my photos. It’s Brilliant !

  4. Jess,
    One of the things that make you look so incredibly beautiful is your cute smile, and feminine features. You rock it girl!💋💋💋

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