Madison, Wisconsin Shemale Dating Classifieds

Madison, Wisconsin 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!

Home / Shemale Dating /

Show Ads In: Appleton / Oshkosh | Duluth / Superior | Eau Claire | Green Bay | Janesville | Kenosha-Racine | La Crosse | Madison | Milwaukee | Sheboygan | Wausau

  • August 3rd, 2026
  • TS Latina Goddess – For Men Who Crave Passion, Fire & Pleasure 🔥💋TS Latina Goddess – For Men Who Crave Passion, Fire & Pleasure 🔥💋  Hello sweetheart 😘 The TS Latina bombshell body type defines me through my soft lips and thick  thighs and my hidden surprise under red lace. Your pleasure stands as my life purpose because I want to  satisfy your desires and make your body experience intense pleasure through my s...
  • FtM seeking Princess Bride in MadisonFtM seeking Princess Bride in Madison FtM seeking Woman in Madison Hi, I'm Andy, age 33, FtM transgender man living in Madison. 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...
  • Mad Town T-Girl 4 Hot Hookup!...Mad Town T-Girl 4 Hot Hookup!... Hi I'm Mattie a trans woman originally from here in Madison. I'm looking to seduce a local man with my feminine wiles and take advantage of him. I have a big surprise bonus to seal the deal and rock your world honey! I just need one guy for an ongoing intimate relationship. If that don't work out th...
  • 👑 Chocolate Queen with Soft Curves & Naughty Desires 🔥👑 Chocolate Queen with Soft Curves & Naughty Desires 🔥  🔥| Do you feel that you want something new and exciting and that you want to  remember for a long time? I am a hot, all natural ebony TS with all the right amount  of curves and a naughty and adventurous spirit. I don’t just know how to tease, please and  make you want ...
  • 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 Madison Area Hi, my fem name is Gloria. I'm a married crossdresser in the Madison 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...
  • August 2nd, 2026
  • Hot TS Latina with Curves, Sass, and a Thirst for You 😘🍷Hot TS Latina with Curves, Sass, and a Thirst for You 😘🍷  You are not the typical girl who lives in the next house… You are the woman who occupies  your thoughts when you are with the woman who lives next door.  Message me here!! I’m a TS Latina goddess —  I have the shape of a coke bottle, the lips of sin, and a t...
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Madison? 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...
  • Spicy and Hot T-Girl from ColombiaSpicy and Hot T-Girl from Colombia Latina T-Girl in Madison 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...
  • Looking for a TS Woman Who Loves to Be Desired 💦🔥 MadisonLooking for a TS Woman Who Loves to Be Desired 💦🔥 Madison  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...
  • Hot trans chick with nice boobsHot trans chick with nice boobs Hot trans chick in Madison. 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...
  • Your Shemale Addiction 😈🥵 Starts NowYour Shemale Addiction 😈🥵 Starts Now Shemale Seeking Male.. Your Fantasy Starts Here 24yr old Transsexual/Shemale in Madison 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 to View my Pix...
  • August 1st, 2026
  • 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....