Jacksonville Trans and Crossdressers Classifieds

Jacksonville trans and crossdressers classifieds - meet local trans women for dating, sex hookups or friendship. Browse transgender and crossdresser classifieds or post your own ad. Meet local TS/CD hotties to live your wildest fantasies!

Home / Shemale Dating / Trans And Crossdressers

Show Ads In: Florida Keys | Ft Myers / SW Florida | Palm Beach | Broward | Daytona Beach | Gainesville | Jacksonville | Lakeland | Miami | Ocala | Orlando | Panama City | Pensacola / Panhandle | Sarasota / Bradenton | Space Coast | St Augustine | Tallahassee | Tampa Bay Area | Treasure Coast

  • June 30th, 2026
  • FtM seeking Princess Bride in JacksonvilleFtM seeking Princess Bride in Jacksonville FtM seeking Woman in Jacksonville Hi, I'm Andy, age 33, FtM transgender man living in Jacksonville. Also, you must love that movie! If you don't get the reference you can still message me anyway! I love that movie and I will watch it with you over and again. View my pics and send me a message ...
  • Partners in crime, or?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...
  • Tiffany Shelle - Your Jacksonville Tranny Girlfriend! πŸ’žTiffany Shelle - Your Jacksonville Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Jacksonville It’s Tiffany Shelle your perfect tranny girlfriend πŸ₯° πŸ’• SAFEπŸ’• πŸ’― LEGIT βœ¨πŸ’ž SKILLED, Exotic and Erotic πŸ’¦ πŸ₯° I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% funct...
  • Beautiful Krystale 25 Jacksonville visiting nowBeautiful Krystale 25 Jacksonville visiting now Beautiful Shemale Visiting Jacksonville Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me.  Krystale25shemale Age: 25 Location: Jacksonville Sex: Shemale Seeking: Man ...
  • Letha Aims to Fill YOU With Her Love Gun!!!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...
  • I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Jacksonville )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Jacksonville ) Sexy Crossdresser Elissa Looking for Hot Fun in JacksonvilleπŸ’‹    Do you like knowing I'm a man in womens clothes.. do I look sexy??    - VEW MY CD PICTURES Are you wanting to satisfy your innermost desires with a sexy shemale such  as myself? My name is Elissa and I a...
  • Smoke me out baby!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...
  • Twisted Sister - Loves to Ride.... and be Ridden!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'...
  • Transgender🟒TINA TSπŸ˜‰πŸ’‹ Transgender🟒TINA TSπŸ˜‰πŸ’‹ Ready to play with a TGirl Tonight? Hi babe, I'm Tina πŸ’‹ 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...
  • Penny for your thoughts?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!! I'm looking for a nice man who will enjoy being with me. Let's enjoy hot dates and explore sexuality together. If that sounds interesting...
  • JacksonvilleJacksonville's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Jacksonville Hi you sexy man! I'm Toni a trans woman from here in Jacksonville. Looking forward to a fun, sexy evening with you tonight. Let's make some memories that we'll never forget! I'm a 28 year old redhead tgirl who's passionate, warm, funny, hung, functional...
  • II'm a Horny Shemale πŸ˜ˆπŸ’‹ Looking For Sex Tonight!! Sexy ShemaleπŸ’Ž Ready to Rock Your World! Local Transsexual - TGIRL Sext App πŸ“² I'm a Transgender and I'm looking for a naughty man with a nice cock here in near me.. Who is wanting to share some sexy fun with me. I've been really horny and hard!! I love taking cock and giving it, what are...
  • Hi Guys!! I am looking for someone fun!Hi Guys!! I am looking for someone fun! This is Lara and I am 41 and transitioned when I was 24. I pass exceptionally well and you will be surprised at my hidden skills. Call me! ...
  • Flirty & Feminine CD Ready for Some Fun πŸ’•πŸ˜ˆFlirty & Feminine CD Ready for Some Fun πŸ’•πŸ˜ˆ  I’m a sexy, smooth, and playful crossdresser who enjoys the attention, desiring  to be treated like a lady. Seeking for a man who can appreciate a well dressed CD for a  casual fun night or even something ongoing. I am a pleaser and I want to be pleased.  πŸ’‹ πŸ’Ž Bath g...
  • DonDon'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...
  • Well Endowed Shemale is beautiful Jacksonville 32Well 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 at BlancaShemale32 for my latest pictures and proof of my size...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Jacksonville Tammy, 39, 38DD, 9" and so cute!! What more could you want in a gurl?!! How about you message me @Tammy38DD and we can talk and meet! Send your recent pic for mine....
  • INTERACTIVE MAP: Transexual Tracker in the Jacksonville Area!INTERACTIVE MAP: Transexual Tracker in the Jacksonville Area! Local Transexual Hookups Meet local transexuals in the Jacksonville area. View our interactive map below to meet local trans hookup members who are seeking dating or sex hook ups. Click any thumbnail below to begin your search. Interactive Jacksonville Trans Hookups Map ...
  • Brandi 27 tall slim hot trans chick 8.5 inchBrandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Jacksonville Beautiful Brandi. If you're attracted to the female form then you will want to message me @ BrandiTS27.  I'm pre-op, tall, slim and beautiful with 8.5 inches for top or bottom. I love oral sex!! Kink friendly, have toys to explore all your ...
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Jacksonville? Hey, I am Jasmin, 8" with a great body and busty. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for hot dates and see where it goes!  Hit me up @SweetJasminT...
  • TS m/f switch 28 new hereTS m/f switch 28 new here TS m/f Switch in Jacksonville Sandi wants to meet hot guy for fun and hot sex. Age 28, nice build, 7.5". Non op functional. Love oral sex, anal sex and kinks of all sorts. View my profile and message me here @SandiSwitchTS...
  • Hot trans chick with nice boobsHot trans chick with nice boobs Hot trans chick in Jacksonville. Sheila wants to meet you. Hey all, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, top or bottom, love oral sex. Want to explore kinks? Me too!! Want to meet me? Send me a message @HotTransChick...
  • Crystal, 27 New to the areaCrystal, 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 masseur, hot body and hung. If you want to get together, Send me a private message Crystal27trans <3 ...
  • Trans Playmate Sex Kitten...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. ...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Jacksonville My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and other times I let i...
  • New Body New MeNew Body New Me M2F post-op in Jacksonville Hi, I'm Natasha, newly transitioned and ready to date. Gorgeous red head with slender legs and curvy body. Want to come and join me for a drink? I love sex in my new gender!!! Seeking a local area man who will enjoy sex and passion with me. Message me online Na...
  • Flawlessly gorgeous trans bombshell in JacksonvilleFlawlessly gorgeous trans bombshell in Jacksonville Trans MtF for Man in Jacksonville I transitioned 6 years ago at the age of 18. I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am 5 feet 7 and have deep blue eyes and luscious lips. Check my profile pics @TransFaye24 pics and prepare to be stunned! Send y...
  • Sassy CD Looking for a Real Man 😘πŸ”₯Sassy CD Looking for a Real Man 😘πŸ”₯  A sweet, sexy and a little naughty crossdresser here, I like to play and  flirt, and I need a strong man who knows what he wants. I enjoy the process of dressing  up, teasing and bringing fantasies to life. If you are into sensual encounters and passionate fun then let me  and y...
  • I Need a Sexy Man to Tame Wild Willy!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 ...
  • Superb Shemale in Jacksonville...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,...
  • British T-girl Seeking Classy Gentleman in Jacksonville...British T-girl Seeking Classy Gentleman in Jacksonville... I am Lacy, a white, blonde haired, trans woman, 30 years old, 5'9, 160 pounds, from Manchester, England and need a man who is educated, refined and handsome. I have just relocated to Jacksonville and am financially independent and looking for a gentleman who is like-minded, equally solvent and has e...
  • DonDon'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'...
  • If you got it flaunt it baby!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 ...
  • I Need a STEAM ROLLER Baby!!!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)Erotic exotic Asian queen in Jacksonville now (25) Asian Transexual in Jacksonville Stunning TS - Talia 25. 5' 8" 140lbs, non op, loves sex. Long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information....
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in JacksonvilleSECRET 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...
  • I want to be a whoreI 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!...
  • Elisabeth waiting to be your QueenElisabeth 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! Private Mes...
  • Local Crossdresser πŸ˜‰πŸ˜‡  LET ME PLAY DRESSUP FOR YOULocal Crossdresser πŸ˜‰πŸ˜‡ LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Jacksonville View My Personal Pix - 🀫  A sexy Crossdresser from Jacksonville, here, and her name is  KaralynnCD. I am pre-op but that has not stopped me from enjoying all the benefits that come with being  a Crossdressing Trans woman. If you like dir...
  • A monster in the sheets, but a lady in the streets...A monster in the sheets, but a lady in the streets... Hello men, I'm Lilith a 27 year old sexy femme, fully functional, passible, sexy and hot to trot trans. I can be a bit racy and dirty when it's appropriate, but always maintain my poise in public. If you live in the Jacksonville area and are interested then drop me a line and introduce yourself. You...
  • Email Local Shemales Now! πŸ’ŒEmail Local Shemales Now! πŸ’Œ Want to Hookup and Find Local 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'reinterested in πŸ˜‰.. Do you want to meet local shemales who want to fuck and have some sex...
  • Spicy and Hot T-Girl from ColombiaSpicy and Hot T-Girl from Colombia Latina T-Girl in Jacksonville Hey guys, I am Colleen and I am looking for a long term relationship. I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery. Nice surpise waiting for you! Send me a private message! ColleenLatinaT...
  • Tantalizing Tina with a HUGE W33NAH!Tantalizing Tina with a HUGE W33NAH! Jacksonville Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Jacksonville men and wnat to show you a time you'll never forget! Do you like them thick, long and uncut? Then I'm the girl for you. Look no further for a passible and functional t girl - HERE I AM!  A...
  • SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now!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 Shemale Profiles  ...
  • Tainted Love - Beyond Compare!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...
  • June 29th, 2026
  • II'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...
  • Trans Man waiting for right date with hot beautyTrans 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...
  • She-male looking for hot date to please. She-male looking for hot date to please. Asian Shemale in the Jacksonville Area Hot Asian shemale wants to date and please you in the art of erotic passion. I'm non op, fully functional, lovely and funny. Please to contact me @CarmelShemaleXXX. My name is Carmel. I'm 33 years old. I like to explore your sexual fantasies! Let's make them ...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Jacksonville Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Jacksonville to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enjoy 24/7 Onli...
  • II'm the Girl Mother 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...