Tallahassee Transgender Classifieds

Browse Tallahassee 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!

Home / Dating / Transgender

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

  • January 23rd, 2026
  • British T-girl Seeking Classy Gentleman in Tallahassee... 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 Tallahassee and am financially independent and looking for a gentleman who is like-minded, equally solvent and has ex...
  • Sexy hung and big busted Hung and Busty Shemale in Tallahassee Tammy, 39, big tits!! Well hung, everything works, clean and so cute!! What more could you want in a gurl?!! How about you message me @Tammy39T and we can talk and meet! Send your recent pic for mine. Username: @Tammy39TLocation: Tallahassee, Florida...
  • Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Tallahassee for Man Hello, thanks for looking at my ad! I'm Lara. I am 32 years old and transitioned when I was 24 but no surgery other than breast augmentation and some minor body touchups. I pass exceptionally well, fully functional. I'm feminine and classy so you will b...
  • Hot sexy shemale doll visiting Tallahassee now Shemale Visiting Tallahassee 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 lo...
  • Penny for your thoughts? Penny TS in Tallahassee 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 an...
  • TS Sugar Baby💎 Your Perfect Trans Fantasy – Let’s Make It a Reality 💋  📍 Location: Tallahassee 💖 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 and...
  • I Need a Sexy Man to Tame Wild Willy! Hung Tallahassee Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Tallahassee 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 an...
  • Hot trans chick with nice boobs Hot trans chick in Tallahassee. 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!! Wan...
  • !!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Tallahassee Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Tallahassee 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...
  • January 22nd, 2026
  • Paula is on prowl tonight... Ever Meet a Ladyboy in Tallahassee? I a hot Asian she-male from Thailand now living in the Tallahassee Area and want sex with big strong American men who can give it hard on the top. Must be strong, but kind and very very horny for this tgirl. I only 125 pounds, 30 years old, and 5'4, and black hai...
  • Don't Worry I Bite! Feisty redhead trans in Tallahassee 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 contr...
  • 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 T...
  • Tiffany Shelle - Your Tallahassee Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Tallahassee 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% functi...