Florida Keys Transgender Classifieds

Browse Florida Keys 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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  • November 8th, 2026
  • Superb Shemale in Florida Keys... T-Girl for NSA Encounters in Florida Keys When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Florida Keys. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle,...
  • Beautiful Krystale 25 Florida Keys visiting now Beautiful Preop Shemale Visiting Florida Keys Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me @Krystale25shemale.  Krystale25shemale Username: @Krystale25shemale Age: 25 Location: Florida Keys, Florida Sex: MtF Trans Seeking:...
  • Transgender Goddess for Late-Night Escapes & Filthy Fun πŸŒ™πŸ’‹  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...
  • Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Florida Keys 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...
  • November 7th, 2026
  • I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Florida Keys I'm queen Delilah a trans woman here in Florida Keys 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...
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Florida Keys! 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 Florida Keys!  No strings - just great times, so join my page free for instant access! Shemale Gia's Florida Keys Sexbook @ShemaleGia27 Pho...
  • TS Sugar BabyπŸ’Ž Your Perfect Trans Fantasy – Let’s Make It a Reality πŸ’‹  πŸ“ Location: Florida Keys πŸ’– 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...
  • Sexy hung and big busted Hung and Busty Shemale in Florida Keys 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: Florida Keys, Flori...
  • Luxury Ebony TS Sugar Baby With Style πŸ‘ πŸ’Ž Hello handsome… I am a ebony trans sugar baby, a beautiful, classy and elegant young lady. I look for confident men that are also very kind to women and who like to spoil a gorgeous lady. Fashion, food and especially great chemistry are my top priorities. let's plan our play date. I love peo...
  • Cute TS Sugar Baby With a Sweet Personality πŸŒΈπŸ’• Hi I’m a trans girl, looking for a nice and confident guy. I like to look pretty and be the centre of attention, so you would need to be confident and also respect women. I love going out with friends and love to be social and have fun and laugh. I also love to be romantic and to be hugged, ki...
  • Paula is on prowl tonight... Ever Meet a Ladyboy in Florida Keys? I a hot Asian she-male from Thailand now living in the Florida Keys 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 h...
  • 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 Florida Keys area come see if you measure up! Click here for explicit photos. L...
  • πŸ’Ž Confident TS Sugar Baby in Florida Keys πŸ’Ž 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...
  • TS Temptress Ready to Ruin You (In the Best Way) πŸ˜ˆπŸ’¦ Florida Keys  Hey lover 😘 I’m a high-femme TS bombshell — curves for days, lips  made for kissing (and more), and a hunger that doesn’t quit. After dinner I appear sweet  but I transform into a woman who crawls to the bed naked while wearing only a mischievous  expression...
  • Cute TS Sugar Baby Seeking MaleπŸ’ŽAria Username: @AriaSweet Trans Friendly: Yes Private Meetups: Yes Phone Chat: Yes Pics Available: 18 Message me if you like feminine Transsexual πŸ’¬ Hello, I am AriaTS here in Florida Keys. A very sweet and very feminine trans-girl that loves to be your sugary little sugar-baby, accompanied by a ...
  • British T-girl Seeking Classy Gentleman in Florida Keys... 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 Florida Keys and am financially independent and looking for a gentleman who is like-minded, equally solvent and has e...
  • Tantalizing Tina with a HUGE W33NAH! Florida Keys Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Florida Keys 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...
  • Hot sexy shemale doll visiting Florida Keys now Shemale Visiting Florida Keys 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...
  • Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Florida Keys 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 ...
  • TS Sugar Baby πŸ’Ž Femme, Flirty & Looking for the Right Man in Florida Keys 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...
  • Flawlessly gorgeous trans bombshell in Florida Keys Trans MtF for Man in Florida Keys 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...
  • Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Florida Keys 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...
  • Petite TS Doll Looking for a Fun Sugar Daddy πŸ¬πŸ’‹ Hi babe... I'm a tiny trans girl, very sexy and feminine. I love to have fun and I'm a very loving girl, I have a lovely sweet smile. I love to be worshiped and pampered by a dominant confident man, who always takes care of his girl, and knows how to please her. HMU HERE BABE!! I am pretty affectio...
  • I Need a Sexy Man to Tame Wild Willy! Hung Florida Keys Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Florida Keys 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 ...
  • Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Florida Keys Look no further honey, I'm Franny an Ebony trans woman here in Florida Keys 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'...
  • Ebony TS Playmate for Men Who Know What They Want πŸ–€πŸ†  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...
  • πŸ’œ Cute TS Girl Looking for the Right Guy 😘 Just moved to Florida Keys😊 Gorgeous, very sweet and easy to get to know. I am a trans girl seeking to meet men that are confident and know what they are looking for, yet are also looking for some friendship with a new person. I enjoy going out for cocktails and having a good time, flirting with ...
  • Email Florida Keys 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...
  • Florida Keys's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Florida Keys Hi you sexy man! I'm Toni a trans woman from here in Florida Keys. 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...
  • Hot trans chick with nice boobs Hot trans chick in Florida Keys. 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...
  • πŸ”₯ Sexy Trans Beauty in Florida Keys – Let’s Play 😘 πŸ”₯ 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...
  • I’m a Sexy and Naughty T-Girl Here in Florida Keys. Florida Keys T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Florida Keys 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  worr...
  • November 6th, 2026
  • Don't Worry I Bite! Feisty redhead trans in Florida Keys 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...
  • Erotic exotic Asian queen in Florida Keys now (25) Asian Transexual in Florida Keys 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...
  • Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Florida Keys? 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...
  • Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Florida Keys 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...
  • πŸ”₯ TS Yessica – Verified & Ready in Florida Keys πŸ”₯ 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...
  • Trans Playmate Sex Kitten... Ebony trans woman in Florida Keys 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. ...
  • Low-Key TS Sugar Baby πŸŒ™ Soft Vibes, Selective Energy in Florida Keys 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. πŸ˜ŒπŸ’„Let's Link Up...
  • Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Florida Keys Area Hi, my fem name is Gloria. I'm a married crossdresser in the Florida Keys 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...
  • πŸπŸ’¦πŸŒΊTRANSGENDER LOVER GIRL - Amanda TS πŸπŸ’¦πŸŒΊ ❀️TS, Transsexual Lover, Wanting to Meet Tonight!!❀️ My name is Amanda, I live in the Florida Keys and I'm willing to travel for some sexy fun tonight! Would you be down for some sexy fun tonight babe?? I need to get naughty and have some sex!! I want to know what you're into as well 😘�...
  • Tiffany Shelle - Your Florida Keys Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Florida Keys 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...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Florida Keys Secret Crossdressing Hookups in Florida Keys 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...
  • 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 Florida Keys area and are interested then drop me a line and introduce yourself. You...
  • 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 ...
  • Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Florida Keys 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'...
  • Strict Shemale Dominatrix in Florida Keys - @DesireeTransDomme Powerful African-Queen Dominatrix in Florida Keys I am full-time professional Domme Desiree. My Florida Keys area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you wil...
  • Penny for your thoughts? Penny TS in Florida Keys 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...
  • TS Tina – Your Seductive Fantasy in Florida Keys πŸ”₯ 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 ...
  • Trans Sugar Baby Energy in Florida Keys - 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...