Jacksonville Transgender Classifieds

Browse Jacksonville transgender classifieds to meet local transexuals, crossdressers and shemales for sex, dating or friendship. Contact any of these trans advertisers to swap pics and contact info. Chat online or text and arrange real-time sex hookups if you feel a connection. It's free to search all trans classifieds, or post your own adult ad!

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February 20th, 2026
Tainted Love - Beyond Compare! Kinky Trans Woman in Jacksonville Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Jacksonville. What kind of kink? You'll have to contact me to find out. I'm open to all sorts of fetish play if you are. I need a hookup with an open minded man. The sort of man who appreci...
Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Jacksonville Look no further honey, I'm Franny an Ebony trans woman here in Jacksonville to fulfill your wildest fantasies. Dreams really do come true when you are with Fabulous Franny. I'm all about the frills and the thrills baby! We can freak it and they don'...
I Need a Sexy Man to Tame Wild Willy! Hung Jacksonville Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Jacksonville with a big wild willy that always seems act out in inappropriate ways at the worst times. For instance I'll be relaxed, minding my own business at my favorite Starbucks ...
TS Sugar Baby💎 Your Perfect Trans Fantasy – Let’s Make It a Reality 💋  📍 Location: Jacksonville 💖 Seeking: Fun, Exciting, &  Discreet Connections Some about me.. Trans SugarBaby: Hey there! I belive I'm a stunning, sweet, and playful trans beauty who loves good  vibes, great chemistry, and unforgettable nights.. I'm in my early 20's an...
Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 I'm in Jacksonville and ready to meeup and hookup in LA tonight.. Let's hang out and have some super sexy fun!! I really need to get out and have some fun. Come check out MY PROFILE, browse my pix, videos and send me a message now...
February 19th, 2026
Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Jacksonville boos out there. I'm a sexy trans woman currently living in large and lovin' every second of it. Hit me up cause I Wanna ROCK too! I'll show you what a real woman can do and everything you don't know now. I'...
Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Jacksonville Hey! Thanks for looking at my ad. This is the first time I've done this so bear with me plz. I am Jared, FtM trans man. I transitioned at age 25 and I just turned 30. Come and meet me!  Check my personal profile @FtMJared29 and say h...
Jacksonville💋 TS Tina – Your Naughty Escape, Anytime, Anywhere 🌎🔥 Hey sexy… Your sweet seductive fully loaded TS dream girl Tina is here to fulfill your deepest desires from anywhere in the world 😘 I possess the right amount of softness while maintaining the perfect playful demeanor and I always welcome men who understand how to treat a genuine wild wom...
Crystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Jacksonville area and want to make some new friends! I am a masseuse, hot body, in great shape, and well hung. If you want to get together, Send me a private message Crystal27trans <3  Username: @Crystal27transLocation: Jacksonville, Flor...
SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Jacksonville Secret Crossdressing Hookups in Jacksonville Hey there. I'm Sam (Samantha when dressed up). If you're reading this ad you may be a crossdresser who needs to let your feminine side out to play. Me too! If you're in the closet or married, it's no problem. I live alone, have a nice, home with a privat...
Selena Trans girl cute looking for love Hello boys. I am looking for love. You want meet me? I want meet you too! See my pictures @SelenaIsTrans and send me a message to set up a date. I like going out for food or drinks, having a great time and I especially like great sex! I am preop and can do top or bottom though I kind of prefer top ...
Hot trans chick with nice boobs Hot trans chick in Jacksonville. Sheila wants to meet you. Hey guys, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, well endowed and functional, top or bottom. I love oral sex giving, receiving or 69. Want to explore kinks? Me too!! Wa...
🔥 TS Yessica – Verified & Ready in Jacksonville 🔥 TS Yessica shows her confident and playful personality when she meets new people because she shows them her authentic self. 😘 You have discovered your perfect trans escort who will create unforgettable experiences while providing an outstanding encounter. I dedicate my free time to people who gen...
Superb Shemale in Jacksonville... T-Girl for NSA Encounters in Jacksonville When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Jacksonville. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle,...
Having fun and Staying Young Young-ish trans fem looking for nice date with lady. I am kind and thoughtful and you will have a very good evening if I take you out. Let me know what you want to do or where you want to go. View profile @SherryTransFem33 and message me. Send your pics for mine. I'm hoping to find real chemistry an...
Penny for your thoughts? Penny TS in Jacksonville Hey, I am Penny! I am recently new here and I am non op switch with a pretty nice pair, both top and bottom! Send me a message online @PennyTSswitch!! I'm a mixed race sweetheart, looking for a nice man who will enjoy being with me. Let's enjoy having some fun, hot dates a...
Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Jacksonville and I got a BIG love gun to whip and pound you with until you scream! I'm def top and alpha and don't take no shit! Imma make you suck me first just for foreplay then I'll throw you back for some hard inser...
Well Endowed Shemale is beautiful Jacksonville 32 Well Endowed Shemale in Jacksonville I am Blanca. I am ready to eat your manhood now. Top or bottom. Bareback if you're clean. Come say hello. I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me @BlancaShemale32 with your recent pic or selfie for my latest pictures a...
Flawlessly gorgeous trans bombshell in Jacksonville Trans MtF for Man in Jacksonville I transitioned 6 years ago at the age of 18. I'm still fully functional but live 24/7 as a female. I pass flawlessly so let's go out on the town! I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am short and cute and I have bedr...
Email Jacksonville Shemales Now! 💌 Want to Hookup and Find Jacksonville Shemales? RADE PIX - MESSAGE - BROWSE PROFILES This Website Helps you find local shemales and TGirls meet local men. It's the perfect place to find what you're interested in 😉.. Do you want to meet local shemales who want to fuck and have some sexy fun? ...
Don't Worry I Bite! Feisty redhead trans in Jacksonville full of fun and loves it rough on the bottom. I'm 5'9, 170 pounds, 32 years old, well endowed, fully functional, passible and hot to trot. You can take me anywhere, but I can't promise to always behave. I have a dirty mind and when the urge hits it's hard to cont...
Trans Sugar Baby Energy in Jacksonville - I'm ready for a night out! Hey there… I’m a sweet, confident, and playful trans beauty in my early 20s who loves good vibes, strong chemistry, and nights that turn into stories you replay later 😘 I enjoy being admired, feeling cared for, and bringing a little sparkle wherever I go. Yes, I can be your “ba...
Email Jacksonville Shemales❤️‍🔥 I'm a well hung TGIRL and Want to have some sexy fun tonight.. Let's Fuck Want to meet the Shemale and Transsexual of your dreams? Look no further, this website gives you instant access to real TGIRLS, SHEMALES and TRANSSEXUALS!! The best part is they are online and you get connected...
Partners in crime, or? Sexy, Slytherin, Aries, ISTP and more, if that gives you a hint about my personality traits. So, I’m a sexy, sensual, tender, animal loving, bookworm. I am a bit of a flirty whore, who loves mystical magical movies and stories, so let’s get that out in the open. If you live in the J...
Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Jacksonville AREA Hi baby! I am waiting to meet you. I can host or travel to you. Down to earth preop transexual woman seeking an understanding man who can appreciate my uniqueness. I am a great cook and great fun! Let your hair down and allow me to pamper you and show you...
I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Jacksonville I'm queen Delilah a trans woman here in Jacksonville searching for her king. You'll get the royal treatment when you're with me honey! Just grab hold of my magic scepter and his majesty can have anything he desires. Imagine the intrigue and scandalou...
Transgender Goddess for Late-Night Escapes & Filthy Fun 🌙💋  It’s late. You’re restless. And you’re craving something… different 😏 - View My Transsexual Dating Profile - As  your TS fantasy girl I offer sultry and smooth vibes while delivering experiences beyond what your ex could have  imagined. My secret between...
Do you know the difference between a dick and a bucket of popcorn? You don't know? Well then take me to the movies baby! Mmmm think of all that creamy, buttery, salty goodness! Talk about a double feature. lol Hope you have the munchies for this hot Jacksonville tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer...
💎 Confident TS Sugar Baby in Jacksonville 💎 I enter any space with my confident trans woman presence which immediately makes me the center of attention. I find great happiness when people express their admiration and appreciation for me while they actively provide me with care. I find complete happiness when someone else handles everything be...
Tiffany Shelle - Your Jacksonville Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Jacksonville It’s Tiffany Shelle your perfect tranny girlfriend 🥰 💕 SAFE💕 💯 LEGIT ✨💞 SKILLED, Exotic and Erotic 💦 🥰 I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% funct...
February 18th, 2026
SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now! HOT!  SHEMALE HOOKUPS  "The girl with a naughty little secret in her panties!" SIGNUP FREE: INSTANT ACCESS! Shemale Profiles Uncensored Photos Swap Your Pics Live Web Cams Private Messages Sext & Hook Up! Join free for Instant Access to the Trans Profiles  &...
Dr Freakin'furter - Mine's Bigger Than Yours! White T-girl here and I'd bet mine is bigger than yours. We'll just let it be our little intimate surprise when the time comes. No one needs to know our business, Let's just keep it discreet. If you live in the Jacksonville area come see if you measure up! Click here for explicit photos. L...
Low-Key TS Sugar Baby 🌙 Soft Vibes, Selective Energy in Jacksonville I’m a TS sugar baby who keeps things calm, classy, and intentional. Evenings without noise, talks that flow naturally - these mean something to me. Confidence shows in stillness, not noise. Soft in manner, sharp in choices. Comfortable standing out, never trying too hard. 😌💄Let's Link Up...
I'm the Girl Your Mum Never Warned You About!... But then, how could your mother have known? I'm Dirty Diana corrupting good decent honest men like yourself here in Jacksonville for many moons. I got a big secret and it's show and tell time baby! It's easier to show you than to tell you. I'm fully functional and passible. I need a sexy man who liv...
Black/Ebony Transsexual - Your New Addiction – One Taste and You’ll Beg for More 🍑💋  Warning: I’m addictive 😘 View My Ebony TS Profile here - I possess more than attractive features. I am a complete  TS woman who enjoys teasing and pleasing while taking control of your dreams. My body features long legs and  thick thighs and soft lips and a hidden secret th...
Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Jacksonville? Hey, I am Jasmin, with a great body and busty. Hit me up @SweetJasminT. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for a fun date and see where it goes! I'm preop and functional, very sex positive and love all s...
Ebony Crossdresser With BBC I'm a Black Crossdresserwith a Big Black Cock 😉💋  Learn more about me. - Visit My Profile I'm living in Jacksonville Florida and I'm a crossdressing ebony lover. I have a nice bigass and a big cock to go along with it.. I just know you would love to play wi...
If you got it flaunt it baby! I'm Shelly-show-me a trans woman here in Jacksonville looking for a man to show me what he's got. If yours is bigger than mine the night's on me. Anything you want to do, or anywhere you want to go baby. That's a tall order to beat tho cause I got 8.5 uncut inches ready for you. Click right here to ...
Trans Playmate Sex Kitten... Ebony trans woman in Jacksonville wants to be your sex kitten and playmate so let's make a playdate! I love all men so any race or body type or political side is fine with me. I can get along with anyone and we're gonna have a great time. I do all men, gay, bisexual, bicurious, swingers and groups. ...
Ebony TS Playmate for Men Who Know What They Want 🖤🍆  If you are the type of person who does not want to waste time with games or small  talk… we are already off to a good start 😘 I am a sexy, curvy TS  babe who loves attention, loves giving pleasure, and lives to be desired. I will come looking like  a dream and be read...
Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Jacksonville Area Hi, my fem name is Gloria. I'm a married crossdresser in the Jacksonville area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but my wife doesn't approve. I REALLY need to let my fem side out to play! I'm seeking cros...
TS Sugar Baby 💎 Femme, Flirty & Looking for the Right Man in Jacksonville I’m a transgender sugar baby who loves femininity, attention, and being appreciated by a confident man who knows exactly what he wants.. Confidence speaks louder than words. Gentle touches matter more than grand gestures ever could. Let's Link Up Babe - Fond of the sugar dynamic. Getting pamp...
I Need a STEAM ROLLER Baby!!! I want you to inject my soul with that sweet lover's pole till there ain't much of me left behind. I'm your whore so just F my brains out tonight. I'm a naughty trans looking for a top big boy to have his way with me. So it's heels and ass up and earth moving sex the hard way. That's the way I like ...
Erotic exotic Asian queen in Jacksonville now (25) Asian Transexual in Jacksonville Stunning TS - Talia 25. Asian mixed race, non op, loves sex. Nice build with long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information. Classy in public but trashy in the bedroom. Versatile and attentive to your needs. L...
Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Jacksonville who doesn't smoke, but has a thing for sexy men smoking cigarettes. Call it a fetish or a kink if you will, but I love it. If done right it is soo sexy and inviting to my senses and gets my motor running every time. Truth is that it's erotic all in...
Hot sexy shemale doll visiting Jacksonville now Shemale Visiting Jacksonville Very hot sevy and curvy shemale chick with big delicious lady stick, fully functions for top or bottom. Message me on my profile page @TaylaShemale1. Seeking a kind gentleman for romance and fun. I adore introducing men who are new to shemale sex. HMU! Possible l...
Road Head Sally Drivin' Hard in Jacksonville Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Jacksonville. Hey, what's the best time for road head? When there's gas in the tank baby! Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or...
I want to be a whore I am a transexual very hot. Good with my mouth and my ass. Comment on my photos. I would appreciate it if you downloaded my photos and share me with other men in the Jacksonville area. Click here and come see me anytime!...
TS Tina – Your Seductive Fantasy in Jacksonville 🔥 Your dream TS girl Tina has arrived to create a hot experience while she will help you discover your most intense sexual fantasies. I create a perfect combination of wild and warm sensations through my soft touch and my playful nature. I find men who understand how to handle a woman with confidence ...
🔥 Sexy Trans Beauty in Jacksonville – Let’s Play 😘 🔥 I’m a confident, flirty trans woman looking for a naughty, open-minded man who knows how to have a good time. I require someone who lives near me to establish genuine emotional bonds through playful games while they disclose their sexual interests to me 😈. waiting for your message babe!! I...

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