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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February 2nd, 2026

Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Sarasota / Bradenton Area Hi, my fem name is Gloria. I'm a married crossdresser in the Sarasota / Bradenton 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...

Penny for your thoughts? Penny TS in Sarasota / Bradenton 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 int...

Debonair 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...

Trans 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...

Flirty & Feminine CD Ready for Some Fun 💕😈 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. 💋 💎 Bath g...

Looking for a TS Woman Who Loves to Be Desired 💦🔥 Sarasota / Bradenton Male Seeking Transsexual for fun and whatever else!! I am a charming, confident and masculine guy and I have a special interest in beautiful TS women. I would be happy to meet anyone who wants to have fun, enjoy and indulge in the process. 💋 I would love to meet a shemale or tra...

February 1st, 2026

Your Shemale Addiction 😈🥵 Starts Now Shemale Seeking Male.. Your Fantasy Starts Here 24yr old Transsexual/Shemale in Sarasota / Bradenton seeking some fun and campanionship. I would like hookups and I'm also wanting love. I think we should play some plans and see what we can come up with.. I'm open minded and ready!! Take a min t...

I love a confident, seductive TS woman—could you be the one? 💋 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,...

Sarasota / Bradenton Addicted to shemales... Male Seeking TS A handsome, fit and confident man, seeking a stunning TS girl to spend exciting nights and incredible moments with. I have a thing for flirty conversations, passionate chemistry and playful antics- if you are looking for a casual meet or if we can make this a more regular thing, I ...

👑 TS Ebony Goddess Looking for Her King Tonight 🔥 🍫 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 ...

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