Sarasota / Bradenton, Florida Shemale Dating Classifieds

Sarasota / Bradenton, Florida shemale dating classifieds. Meet local crossdressers, transexuals and shemales for romance, sex or just make new transgender friends. escorts, body rubs & sex service listings. Select your location below to find shemales near you. It's free to search or post your own ad!

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  • May 6th, 2026
  • 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....
  • I Need a Sexy Man to Tame Wild Willy!I Need a Sexy Man to Tame Wild Willy! Hung Sarasota / Bradenton Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Sarasota / Bradenton 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 fav...
  • Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Sarasota / Bradenton Seeking!!Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Sarasota / Bradenton Seeking!! Seduction Starts with One Look…Once I have your attention, baby, I don’t let go. 😏 I’m the trans woman you’ve been dreaming about—sexy, confident, and oh-so-willing to turn up the heat. Let’s start slow… a few drinks, a little teasing, some whispers abo...
  • 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 Sarasota / Bradenton 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...
  • I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Sarasota / Bradenton )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Sarasota / Bradenton ) Sexy Crossdresser Elissa Looking for Hot Fun in Sarasota / BradentonπŸ’‹    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...
  • Seeking All TS Beauties in Sarasota / BradentonSeeking All TS Beauties in Sarasota / Bradenton  I am a masculine, dominant, and very passionate man, and I am looking for a sensual  and seductive TS woman to explore our deepest desires together. No matter whether you like to be the  boss or to be taken care of, I am all about creating electric chemistry and unforgettable moments...
  • INTERACTIVE MAP: Transexual Tracker in the Sarasota / Bradenton Area!INTERACTIVE MAP: Transexual Tracker in the Sarasota / Bradenton Area! Local Transexual Hookups Meet local transexuals in the Sarasota / Bradenton 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 Sarasota / Bradenton Trans Hookups Map ...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Sarasota / Bradenton Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Sarasota / Bradenton to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos ...
  • Looking for My TS Queen πŸ‘‘πŸ’‹Looking for My TS Queen πŸ‘‘πŸ’‹ I’m a confident, successful, and open-minded man looking to connect with a beautiful TS woman for fun, passion, and maybe something more. πŸ’• I appreciate a woman who knows her worth and loves to be treated right. Whether it’s a romantic dinner, steamy nights, or spontaneous adventures,...
  • 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! ...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Sarasota / Bradenton 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....
  • Local Crossdresser πŸ˜‰πŸ˜‡  LET ME PLAY DRESSUP FOR YOULocal Crossdresser πŸ˜‰πŸ˜‡ LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Sarasota / Bradenton View My Personal Pix - 🀫  A sexy Crossdresser from Sarasota / Bradenton, 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....
  • TS Beautiesβ€”Let’s Have Some REAL Fun! 😏πŸ”₯TS Beautiesβ€”Let’s Have Some REAL Fun! 😏πŸ”₯  I am a tall, fit, and successful man and I have a taste for gorgeous TS women  who love to be adored, desired and pleasured. Whether you are looking for a wild  night, a passionate escape or something ongoing, I know how to treat a woman right. πŸ’‹ Must  have confidence, charm...
  • New Body New MeNew Body New Me M2F post-op in Sarasota / Bradenton 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...
  • Sarasota / BradentonSarasota / Bradenton's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Sarasota / Bradenton Hi you sexy man! I'm Toni a trans woman from here in Sarasota / Bradenton. 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, ...
  • I’m a Sexy and Naughty T-Girl Here in Sarasota / Bradenton.I’m a Sexy and Naughty T-Girl Here in Sarasota / Bradenton. Sarasota / Bradenton T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Sarasota / Bradenton 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...
  • 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 Sarasota / Bradenton 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...
  • Shemale 4 Men πŸ†πŸ’¦  Sarasota / Bradenton Ready Now!! Shemale 4 Men πŸ†πŸ’¦ Sarasota / Bradenton Ready Now!!  Come Closer, I Don’t Bite, Unless You Do Enjoy ItπŸ˜‰   View My Private Pictures -  If you’re looking  to mess around… I don’t know, maybe in a way that’s a bit spicy for the  two of us? I’m a trans beauty with a dirty mind and I love...
  • 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...
  • DonDon't Worry I Bite! Feisty redhead trans in Sarasota / Bradenton 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...
  • Superior Massage by gorgeous T-GirlSuperior Massage by gorgeous T-Girl T-Girl for Dating in Sarasota / Bradenton 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 Usern...
  • Trans Playmate Sex Kitten...Trans Playmate Sex Kitten... Ebony trans woman in Sarasota / Bradenton 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 ...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Sarasota / Bradenton 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 re...
  • Seeking a Stunning TS for Passion & Pleasure 😘πŸ”₯Seeking a Stunning TS for Passion & Pleasure 😘πŸ”₯  I am a confident, strong and open minded man, who knows what I want from a woman  – a sexy, elegant and fun loving TS woman to share unforgettable moments with. I am here to  explore and enjoy every second of it, whether it is a casual hookup, a fun date or a  deep connect...
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Sarasota / Bradenton 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 a...
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  • 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 S...
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  • 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...
  • Sarasota / Bradenton πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Sarasota / Bradenton πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Real Latina TS Seeking πŸ”₯Ready to Fulfill Your Wildest Fantasies  My Spicy Latina Shemale Pix! -Are you looking for a sexy shemale to play with? I'm a bit of a drama queen. I love dressing pretty and getting my nails done. I will also dress sexy in lingerie for you. Do you want to have a hoo...
  • 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 Sarasota / Bradenton area come see if you measure up! Click here for explicit photos...
  • Ebony Shemale in Sarasota / Bradenton ❀️😘 Seeking Male for Naughty Fun!Ebony Shemale in Sarasota / Bradenton ❀️😘 Seeking Male for Naughty Fun! Ebony Shemale Stefanie Ready to Fulfill Your Wildest Fantasies πŸ’‹ Are you looking for a hot and kinky black shemale in Sarasota / Bradenton? Look no further because I am here to satisfy all your desires. My name is StefanieBBC and I'm an Ebony Shemale..  I am a stunning transgender woman who...
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  • 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 Sarasota / Bradenton tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut an...
  • Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹  You want flavor? Spice? A woman who can dance for you, then ride you like she  owns you? That’s me, papi 😘 I’m a curvy, high-femme  TS Latina with a pretty face, wild hips, and a very naughty surprise underneath. View My Latina TS Pictures - I love to  tease, fl...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Sarasota / Bradenton 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...
  • πŸ‘‘ TS Ebony Goddess Looking for Her King Tonight πŸ”₯πŸ‘‘ TS Ebony Goddess Looking for Her King Tonight πŸ”₯  πŸ« Juicy, thick, and so addictive! I am a stunning ebony trans  vixen with the perfect hourglass figure, long legs, and a playful personality. I have a  thing for men who know what they want and are not afraid to go after it. Whether you are  a professional or a newbie to the ...
  • May 5th, 2026
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy \ Sarasota / Bradenton!HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Sarasota / Bradenton! 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 Sarasota / Bradenton!  No strings - just great times, so join my page free for instant access! Shemale Gia's Sarasota / Bradenton Sexbook @S...
  • THE RIGHT GUY FOR THE JOB!!!THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! πŸ˜‰ My name is Frank and I'm here to see if I can find any transgender ladies who wants a real man to treat them right.. I'm living in xxxx but I'm willing to travel. I have a great house we can have some fun in as well. I have a HOTTUB, arcade, th...
  • I love a confident, seductive TS womanβ€”could you be the one? πŸ’‹I love a confident, seductive TS womanβ€”could you be the one? πŸ’‹  A handsome, intelligent and adventurous man, here looking to meet a gorgeous TS woman to have  excitement, chemistry and wild nights. I just love confident women who know what they want and I’m more  than ready to spoil, explore and indulge in pleasure together.  Handsome,...
  • πŸ‘„ Dark-Skinned TS Beauty Looking for Fun, Passion & PleasureπŸ‘„ Dark-Skinned TS Beauty Looking for Fun, Passion & Pleasure  πŸ‘‘ I am the Queen of Your Fantasies – Come Worship Me! I am  a gorgeous, confident, ebony TS, with a body built for pleasure and a mind full of naughty  ideas. If you are looking for high class experience, filled with deep pleasure, seductive touches and  sensual moments...
  • Flawlessly gorgeous trans bombshell in Sarasota / BradentonFlawlessly gorgeous trans bombshell in Sarasota / Bradenton Trans MtF for Man in Sarasota / Bradenton 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!...
  • Spicy 🌢  Latina Shemale in Sarasota / Bradenton Ready to Fill You πŸ˜‰πŸ˜‰ Spicy 🌢 Latina Shemale in Sarasota / Bradenton Ready to Fill You πŸ˜‰πŸ˜‰ LATINA SHEMALE SEEKING πŸ”₯🌢  Are you looking for a spicy/hot HISPANIC TS.. absolutely KINKY and ready to do anything?? I'm from Sarasota / Bradenton.  Don't look any further, because I'm here to make all your wet dreams come true. My name is MARIA TS and I am a pre-op transgender woma...
  • Hot Shemale in Sarasota / Bradenton Ready to Fulfill Your Wildest Fantasies πŸ‘„πŸ’¦πŸ†Hot Shemale in Sarasota / Bradenton Ready to Fulfill Your Wildest Fantasies πŸ‘„πŸ’¦πŸ† I'm TS and Looking to Date in Sarasota / Bradenton My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Sarasota / Bradenton who knows how to have a good time? Look no further, because I'm here to make all your dreams come true. I'm really excited about possibly meeting some li...
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  • TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘  Papi… I’ve been thinking about you 😘 View More Sexy TS PIX - My curvy figure and thick TS  Latina body has caramel skin while my filthy mind and mouth were made for you 😈. I become  submissive only when you want me to submit while I transform into a dominant forc...
  • YOUR EBONY SHEMALE - big boobs and a BIG COCK! Sarasota / BradentonYOUR EBONY SHEMALE - big boobs and a BIG COCK! Sarasota / Bradenton Hot Hot Hot! Sinead, a black shemale in Sarasota / Bradenton ready to make all of your  wildest fantasies come true! πŸ’‹πŸ”₯ My Pictures and Profile! -- You want to find a sexy ebony shemale in  Sarasota / Bradentonto fulfill all your dreams? Then stop searching because I am ready to ma...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Sarasota / BradentonSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Sarasota / Bradenton Secret Crossdressing Hookups in Sarasota / Bradenton 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 ...
  • Crystal, 27 New to the areaCrystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Sarasota / Bradenton 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 ...