Ocala Trans and Crossdressers Classifieds

Ocala 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

  • September 24th, 2026
  • Tantalizing Tina with a HUGE W33NAH!Tantalizing Tina with a HUGE W33NAH! Ocala Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Ocala 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!  About me: 29 ye...
  • 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 O...
  • Dr FreakinDr 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 Ocala area come see if you measure up! Click here for explicit photos. Look for...
  • British T-girl Seeking Classy Gentleman in Ocala...British T-girl Seeking Classy Gentleman in Ocala... 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 Ocala and am financially independent and looking for a gentleman who is like-minded, equally solvent and has exceptio...
  • DonDon't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Ocala Look no further honey, I'm Franny an Ebony trans woman here in Ocala 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't have to know...
  • 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 Ocala 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'm sexy,...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Ocala Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Ocala 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 Online Chat Make ...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Ocala 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 it grow....
  • Transgender🟒TINA TSπŸ˜‰πŸ’‹ Transgender🟒TINA TSπŸ˜‰πŸ’‹ Ready to play with a TGirl Tonight? Hi babe, I'm Tina πŸ’‹ I'm in Ocala 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.. Let'...
  • Erotic exotic Asian queen in Ocala now (25)Erotic exotic Asian queen in Ocala now (25) Asian Transexual in Ocala 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....
  • DonDon't Worry I Bite! Feisty redhead trans in Ocala 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 control mys...
  • Tiffany Shelle - Your Ocala Tranny Girlfriend! πŸ’žTiffany Shelle - Your Ocala Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Ocala 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% functioning ...
  • Penny for your thoughts?Penny for your thoughts? Penny TS in Ocala 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 hit me...
  • 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 Ocala 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 insertion, p...
  • 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...
  • Superb Shemale in Ocala...Superb Shemale in Ocala... T-Girl for NSA Encounters in Ocala When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Ocala. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle, f#ck and do a...
  • 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...
  • INTERACTIVE MAP: Transexual Tracker in the Ocala Area!INTERACTIVE MAP: Transexual Tracker in the Ocala Area! Local Transexual Hookups Meet local transexuals in the Ocala 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 Ocala Trans Hookups Map ...
  • OcalaOcala's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Ocala Hi you sexy man! I'm Toni a trans woman from here in Ocala. 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 and loves men...
  • 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  ...
  • Free Florida Transexuals GuideFree Florida Transexuals Guide Florida Transexuals Guide The Florida Transexuals Guide was prepared by our trans experts at AmericanTransexuals.com. We bring trans women and admirers together for friendship, dating and sex hookups. View our free Florida Transexuals Guide online.  Where to Meet Transexuals in Florida...
  • 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 Ocala 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 lives near...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Ocala 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....
  • 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...
  • Crystal, 27 New to the areaCrystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Ocala 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 ...
  • I Need a Sexy Man to Tame Wild Willy!I Need a Sexy Man to Tame Wild Willy! Hung Ocala Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Ocala 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 and see a beau...
  • Email Ocala Shemales❀️‍πŸ”₯Email Ocala Shemales❀️‍πŸ”₯ 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...
  • II'll Make You Feel Like a King Baby! Trans Queen Seeks King in Ocala I'm queen Delilah a trans woman here in Ocala 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 scandalous positions we...
  • Hot sexy shemale doll visiting Ocala now Hot sexy shemale doll visiting Ocala now Shemale Visiting Ocala Very hot sevy and curvy shemale chick with 8 inch lady stick. Message me on my profile page @TaylaShemale1. Seeking kind gentleman for romance and fun. Possible long term with the right man. ...
  • Do you know the difference between a dick and a bucket of popcorn?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 Ocala tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer than a...
  • 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! ...
  • Flawlessly gorgeous trans bombshell in OcalaFlawlessly gorgeous trans bombshell in Ocala Trans MtF for Man in Ocala 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 your rec...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in OcalaSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Ocala Secret Crossdressing Hookups in Ocala 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 private garag...
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Woman in Ocala Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Ocala. 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 appreciates what I br...
  • She-male looking for hot date to please. She-male looking for hot date to please. Asian Shemale in the Ocala 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 come tr...
  • 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 ...
  • Trans Playmate Sex Kitten...Trans Playmate Sex Kitten... Ebony trans woman in Ocala 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. I am al...
  • I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Ocala )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Ocala ) Sexy Crossdresser Elissa Looking for Hot Fun in OcalaπŸ’‹    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 am a pre...
  • Well Endowed Shemale is beautiful Ocala 32Well Endowed Shemale is beautiful Ocala 32 Well Endowed Shemale in Ocala 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! ...
  • September 23rd, 2026
  • Beautiful Krystale 25 Ocala visiting nowBeautiful Krystale 25 Ocala visiting now Beautiful Shemale Visiting Ocala 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: Ocala Sex: Shemale Seeking: Man ...
  • I’m a Sexy and Naughty T-Girl Here in Ocala.I’m a Sexy and Naughty T-Girl Here in Ocala. Ocala T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Ocala area. Sweet, sexy, friendly and outgoing. I will definitely make you feel happy/sexy vibes and relaxed. I have an amazing body boys. I'm a pretty t-girl with a big present! So forget all your  worries and stress...
  • New Body New MeNew Body New Me M2F post-op in Ocala 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 NatashaM2...
  • Your Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ OcalaYour Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ Ocala I am a  hot, cool and confident crossdresser who enjoys the feeling of being wanted, loved and taken care  of like a lady. Whether you are looking for some hot action, a nice relationship or even a  friend with benefits, I am here to make it unforgettable. πŸ’‹ πŸ‘  Feminine, fun and ...
  • Superior Massage by gorgeous T-GirlSuperior Massage by gorgeous T-Girl T-Girl for Dating in Ocala I will help you unwind and create a cozy environment for you! I am 36DD, 7" and can give you so much pleasure. View my Transgender World profile and message me for my pics! @GayleTGirl Gayle <3    Transgender World Profile Username: GayleTGirl...
  • 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 Ocala area. Click here and come see me anytime!...
  • Selena Trans girl cute looking for loveSelena 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 and send message for date....
  • 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 Ocala 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 naughty...
  • Local Crossdresser πŸ˜‰πŸ˜‡  LET ME PLAY DRESSUP FOR YOULocal Crossdresser πŸ˜‰πŸ˜‡ LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Ocala View My Personal Pix - 🀫  A sexy Crossdresser from Ocala, 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 dirty games and l...
  • 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 Ocala area and are interested then drop me a line and introduce yourself. You can me...
  • Spicy and Hot T-Girl from ColombiaSpicy and Hot T-Girl from Colombia Latina T-Girl in Ocala 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...