Orlando Trans and Crossdressers Classifieds

Orlando 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 23rd, 2026
  • 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 Orlando area and are interested then drop me a line and introduce yourself. You can ...
  • Spicy and Hot T-Girl from ColombiaSpicy and Hot T-Girl from Colombia Latina T-Girl in Orlando 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...
  • Marina TS πŸ† Visiting and ReadyMarina TS πŸ† Visiting and Ready Visitng Houston, Texas - Your TGirl Escort Hi guys Marina TS visiting your city …. We can start a sexy friendship, but if you are generous, it would not be bad. Please call me and text me when you are ready....MESSAGE ME HERE. Sexy, latina, femenine and beatiful TS woman here. English/e...
  • Smoke me out baby!Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Orlando 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 it's...
  • TS m/f switch 28 new hereTS m/f switch 28 new here TS m/f Switch in Orlando 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...
  • Elisabeth waiting to be your QueenElisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Orlando 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 Message ...
  • Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates.Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Orlando Area Hi, my fem name is Gloria. I'm a married crossdresser in the Orlando area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but wife doesn't approve. I really need to let my fem side out to play! I'm seeking cross dressing fr...
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy \ Orlando!HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Orlando! LET'S TAKE CARE OF THAT TRANNY FANTASY! "Experience your secret tranny desires in real life!"  Hot shemale Gia wants to hook up with you in Orlando!  No strings - just great times, so join my page free for instant access! Shemale Gia's Orlando Sexbook @ShemaleGia27 Photos: 42 V...
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Orlando Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Orlando Looking for someone a little different from the average guy? Hey, I'm Barry, age 31, fit and healthy. I have a square jaw, sparkling eyes and short dark hair. I like to dress sharp. I am currently looking for a fun lady to spend time with. Possible longterm relationship.&n...
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Orlando 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 hi!&nb...
  • Having fun and Staying YoungHaving fun and Staying Young Young 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 and message me xoxo, Sherry....
  • September 22nd, 2026
  • 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...
  • FtM seeking Princess Bride in OrlandoFtM seeking Princess Bride in Orlando FtM seeking Woman in Orlando Hi, I'm Andy, age 33, FtM transgender man living in Orlando. 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 @AndyFtM4P...
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Orlando? 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...
  • Hot trans chick with nice boobsHot trans chick with nice boobs Hot trans chick in Orlando. 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...
  • M-F trans woman wants a dateM-F trans woman wants a date I want someone understanding and kind. Please check out my profile and rate me. I am 36, 5 feet 6 and elegant! My name is Lyssa....