Wisconsin Transgender Sex Ads

Browse Wisconsin transgender sex ads to meet local transexuals, crossdressers and shemales for sex, dating or friendship. It's free to search the trans sex classifieds, or post your own adult ad!

Home / Alternative Sex Ads / Transgender Sex Ads

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

  • April 20th, 2026
  • Sexy Shemale Ready to Play in Kenosha-RacineSexy Shemale Ready to Play in Kenosha-Racine Looking for a hot man who can handle all that I have to offer? Well, look no further because I am here and ready to rock your world. My name is Raye and I am a shemale seeking a local man for some mind-blowing fun. I love it all - from being a top or bottom, giving blowjobs, getting my ass played...
  • Raunchy Shemale Seeking Local Man for Hot EncountersRaunchy Shemale Seeking Local Man for Hot Encounters Are you looking for a wild time with a sexy shemale in La Crosse, Wisconsin? Look no further because I'm here to fulfill all your dirty fantasies. My name is Adi and I'm a naughty shemale who loves to play rough and dirty with a man who can handle me. I enjoy being both a top and a bottom, giving...
  • Hot Shemale Looking for Local Man to Fulfill All Your FantasiesHot Shemale Looking for Local Man to Fulfill All Your Fantasies Are you ready to have the time of your life with a sexy shemale? Well, look no further because I'm here to make all your wildest dreams come true. My name is Josee and I'm a naughty shemale from Janesville, Wisconsin looking for a man who can handle all that I have to offer. I love getting down a...
  • Eclectic Transgender Beauty Looking for Love in MadisonEclectic Transgender Beauty Looking for Love in Madison Hey there, I'm Yevette from Madison, Wisconsin. I'm a curvy Latina beauty who loves exploring my LGBTQ identity. I embrace my uniqueness and am looking for someone who appreciates it too. I enjoy long walks by Lake Monona, trying out new dishes at Graze, and catching live music at the High Noon ...
  • April 19th, 2026
  • Looking for Love and Adventure in Sheboygan!Looking for Love and Adventure in Sheboygan! Hey there! I'm Daisey, a fun-loving transgender gal from Sheboygan, Wisconsin. 🌈 I wanted to put myself out there and see if love is waiting just around the corner. So here I am, writing this ad in hopes of finding someone special. Now, let me tell you a bit about myself. I have a bubbly perso...
  • Seeking Local Man for Wild Shemale FunSeeking Local Man for Wild Shemale Fun Are you looking for a hot shemale to fulfill all your wildest fantasies? Look no further, because I'm Camilla from Duluth / Superior, Wisconsin, and I'm ready to play! I'm a kinky shemale who loves to get down and dirty with a man who knows how to handle me. I enjoy everything from giving sloppy...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Wisconsin 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....
  • Raunchy Shemale Dyana Seeking Local Man for Wild FunRaunchy Shemale Dyana Seeking Local Man for Wild Fun Looking for a hot guy in Madison who can handle a naughty shemale like me? I'm Dyana, and I'm ready to show you a good time. Let's get down and dirty together for some mind-blowing action. I love being both top and bottom, so we can switch things up and explore all our desires. From deepthroati...
  • Spark Up Some Chemistry with Billie!Spark Up Some Chemistry with Billie! Hey there, I'm Billie from Eau Claire, Wisconsin! 🌈 Are you looking for someone who is proud to be transgender and loves being part of the LGBTQ community? Well, look no further because that's me! 💖 I may not be a supermodel, but I have a heart of gold and a great sense of humor. I enjoy go...
  • Local Shemale Looking for Hot Fun and Great SexLocal Shemale Looking for Hot Fun and Great Sex I'm Juliane, a sexy shemale from Wausau, Wisconsin, seeking a local man for some steamy encounters. I love getting down and dirty, exploring all kinds of naughty pleasures with my partner. If you're into wild and kinky fun, then I'm the perfect match for you! I enjoy being both top and bottom, gi...
  • Eclectic Transgender Beauty Seeking ConnectionEclectic Transgender Beauty Seeking Connection Hey there! I'm Sophia, a transgender woman from Wausau, Wisconsin. I may not fit society's norms, but that's what makes me unique and beautiful. I love exploring my identity and connecting with others in the LGBTQ community. I enjoy long walks in Rib Mountain State Park, grabbing a coffee at Bre...
  • Sexy Shemale in Eau Claire Ready to Fulfill Your Wildest Fantasies 💋🍆💦Sexy Shemale in Eau Claire Ready to Fulfill Your Wildest Fantasies 💋🍆💦 Are you looking for a hot and horny shemale to play with? Look no further, because I'm here to make all your dreams come true. My name is Michel and I am a pre-op transgender woman who loves to have fun in the bedroom. 🌈✨ I enjoy being both a top and a bottom, so we can switch things up and ...
  • Looking for Love and Adventure!Looking for Love and Adventure! Hey there, lovely people of Janesville! My name is Allyce, and I'm a transgender gal who's ready to dive into the dating world. 🌈✨ I may not have a "typical" body type, but trust me when I say that my heart is overflowing with kindness and compassion. As for my ethnicity and nationality, let...
  • EvelinaEvelina's Enchanting Transgender Tale Hey there, I'm Evelina from Milwaukee, Wisconsin. I may not fit society's idea of "normal," but that's what makes me uniquely me! Being transgender has opened up a whole new world of possibilities and experiences for me. I love connecting with others in the LGBTQ community and sharing our stories....
  • Raunchy Shemale Looking for Hot Encounters in Eau ClaireRaunchy Shemale Looking for Hot Encounters in Eau Claire Are you a man who's into wild, kinky fun with a sexy shemale? Well, look no further because I'm Carolina and I'm here to fulfill all your dirty desires. I'm a top shemale seeking a local man who can handle my huge throbbing cock and tight ass. I love giving sloppy blowjobs, getting my ass pound...
  • Seeking Local Man for Shemale Fun in Green BaySeeking Local Man for Shemale Fun in Green Bay Are you looking for a wild time with a sexy shemale in Green Bay, Wisconsin? Look no further because I am here to fulfill all your naughty fantasies. My name is Katharyn and I am ready to show you a good time like no other. I love getting down and dirty with a man who knows how to handle a shemal...
  • Local Shemale Looking for Hot Fun in WausauLocal Shemale Looking for Hot Fun in Wausau I'm a sexy shemale named Jacki who's on the hunt for a local man to have some steamy encounters with. I love getting down and dirty, so if you're into wild and kinky sex, I'm your girl... err, shemale! 😈 When it comes to bedroom activities, I'm open to just about anything. I enjoy giving and r...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Are you ready to get down and dirty with a sexy shemale in Duluth / Superior, Wisconsin? Well, look no further because I am Marti, your ultimate fantasy come true! I am a hot and horny shemale looking for a man who can handle all of my wildest desires. When it comes to sex, I love it all. From b...
  • Sexy Shemale in Milwaukee Looking for Hot Fun!Sexy Shemale in Milwaukee Looking for Hot Fun! Are you ready to have the time of your life with a naughty shemale like me? My name is Lucia and I am seeking a local man who can handle all my dirty desires. I love being both top and bottom, giving blowjobs, getting my tight ass played with, sucking dick until it's throbbing, and riding cock unt...
  • Hot Shemale in Janesville Ready to Play and FuckHot Shemale in Janesville Ready to Play and Fuck I love getting down and dirty with a man who knows how to handle a shemale like me. My name is Allyn and I'm looking for a local guy who can keep up with my insatiable appetite for sex and fun. You can find me in the FreeSexAds.com Shemale Profiles at allynj86036. I enjoy everything from top to b...
  • A Sensual Journey of Self-DiscoveryA Sensual Journey of Self-Discovery Hey there! I'm Tabbatha, a transgender woman from Green Bay, Wisconsin. I love embracing my true self and being part of the LGBTQ community. It's all about love and acceptance, right? 💖 I'm looking for someone who appreciates authenticity and is up for a fun time exploring local spots like Tit...
  • Raunchy Shemale Tami in Duluth/Superior Ready to PlayRaunchy Shemale Tami in Duluth/Superior Ready to Play I'm a hot and horny shemale looking for a local man who can handle all of me. I love getting down and dirty, so if you're into wild and kinky fun, I'm your girl. My name is Tami, and I'm ready to show you a good time. I enjoy being both a top and a bottom, so we can switch things up and see where...
  • A Date with DestinyA Date with Destiny Hey there, I'm Trula from Madison, Wisconsin. I'm a curvy transgender woman of Hispanic descent, and I love embracing my unique identity within the LGBTQ community. If you're looking for someone who's confident, fun-loving, and always up for new adventures, then look no further! I enjoy exploring l...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Are you a man in Green Bay looking for a wild time with a sexy shemale? Well, look no further because I'm Hope and I'm here to fulfill all your dirty fantasies. I love being both top and bottom, so we can switch it up and have the best of both worlds. I enjoy giving sloppy blowjobs, getting my tig...
  • Spark Up Some Magic with Lita!Spark Up Some Magic with Lita! Hey there! I'm Lita, a transgender cutie from Madison, Wisconsin. I may have a curvy body, but my personality shines brighter than the sun! 🌟 I love exploring new places in Madison like the Olbrich Botanical Gardens or grabbing a cup of coffee at Colectivo Coffee. Being part of the LGBTQ comm...
  • Looking for Love and Adventure!Looking for Love and Adventure! Hey there! My name is Jenelle, and I'm a proud transgender woman living in the beautiful city of Wausau, Wisconsin. 💖 I may not have the typical body type you'd expect, but that's what makes me unique! Diversity is what makes life exciting, don't you think? 🌈 I come from a mix of ethnic bac...
  • Sexy Shemale Seeking Local Man for Hot FunSexy Shemale Seeking Local Man for Hot Fun Looking for a man who can handle this tight, throbbing shemale ass? Look no further! I'm Cora, a sexy shemale from Appleton / Oshkosh, Wisconsin, ready to show you a good time. I love to play both top and bottom, giving and receiving blowjobs that will leave you begging for more. I enjoy getting m...
  • Local Shemale Seeking Hot Man for Wild Fun and OrgasmsLocal Shemale Seeking Hot Man for Wild Fun and Orgasms Are you looking for a sexy shemale in Green Bay who knows how to have a good time? Look no further, because I'm here to fulfill all your wildest fantasies. My name is Karyl and I'm a horny shemale looking for a local man who can handle my insatiable appetite for pleasure. When it comes to sex, I ...
  • Hot Shemale in Madison Ready to PlayHot Shemale in Madison Ready to Play Are you looking for a wild time with a sexy shemale? Look no further, because I'm here to fulfill all your naughty desires. My name is Lauryn and I'm seeking a local man for some hot and steamy fun. I love getting down and dirty with a guy who knows how to please me. I enjoy being both top and b...
  • Sexy Shemale Looking for Hot Fun in Kenosha-Racine!Sexy Shemale Looking for Hot Fun in Kenosha-Racine! Are you ready to have a wild time with a sexy shemale named Elvira? I'm looking for a local man who can handle all the naughty things I have in store. From being your dominant top to giving you mind-blowing blowjobs, I'm up for anything that will make us both scream with pleasure. I love playing w...
  • Euphoric Trans Beauty Seeking Connection 🌈Euphoric Trans Beauty Seeking Connection 🌈 Hey there! I'm Diane, a proud transgender woman from Kenosha-Racine, Wisconsin. I may not fit society's narrow definition of beauty, but my unique body type and ethnicity make me who I am. You can check out my pics at my personal profile page @dianek12412. I love being part of the LGBTQ community...
  • Sensual Transgender Beauty Looking for Love in MadisonSensual Transgender Beauty Looking for Love in Madison Hey there! I'm Nance, a transgender woman from Madison, Wisconsin. I may not fit society's idea of "normal," but that's what makes me unique and special. I love embracing my true self and being part of the LGBTQ community. I'm looking for someone who can appreciate me for who I am, inside and out...
  • Looking for Love and Adventure! <br>Looking for Love and Adventure!
    Hey there, lovely people of Kenosha-Racine, Wisconsin! I'm Juliana, a transgender woman who is ready to explore the world of dating and find that special someone. 💖 I may not fit into society's typical mold, but that's what makes me unique and fabulous! My body type is as diverse as the colors...
  • Elegantly Transcendent Seeking ConnectionElegantly Transcendent Seeking Connection Hey there, I'm Kelley from Duluth / Superior, Wisconsin. I'm a curvy and confident transgender woman of mixed heritage. I love exploring my identity and embracing the LGBTQ community. Being trans has brought so much beauty and depth to my life, and I wouldn't have it any other way. I'm looking f...
  • Hot Shemale in Kenosha-Racine Ready to PlayHot Shemale in Kenosha-Racine Ready to Play Looking for a man who can handle a shemale like me? Look no further, because Sylvie is here to fulfill all your wildest fantasies. I'm a naughty tranny seeking a local guy for some steamy fun and unforgettable sex sessions. If you're into exploring new things and pushing boundaries, then I'm the p...
  • Local Shemale Looking for Hot and Steamy EncountersLocal Shemale Looking for Hot and Steamy Encounters Hey there, I'm a sexy shemale named Britani from Eau Claire, Wisconsin. I'm looking for a local man who can handle all my naughty desires. When it comes to sex, I love being on top and taking control. I enjoy giving mind-blowing blowjobs, getting my tight ass pounded, and feeling a huge throbbing co...
  • FtM seeking Princess Bride in WisconsinFtM seeking Princess Bride in Wisconsin FtM seeking Woman in Wisconsin Hi, I'm Andy, age 33, FtM transgender man living in Wisconsin. 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 @AndyF...
  • Looking for Love and Adventure in Appleton/Oshkosh!Looking for Love and Adventure in Appleton/Oshkosh! Hey there, lovely people of Appleton and Oshkosh! My name is Ali, and I'm a fun-loving transgender individual who's ready to dive into the dating scene. 💖 So, let me tell you a bit about myself. I have a curvy body that I embrace with confidence, reflecting my love for self-expression. 🌈 Be...
  • Sexy Shemale Seeking Local Man for Wild FunSexy Shemale Seeking Local Man for Wild Fun Hey boys, I'm Melisse and I am a horny shemale looking for a man who can handle all of me. I love to be on top, bottom, or anywhere in between. Let's get down and dirty with some intense fucking, blowjobs, ass play, and more. My tight hole is ready for your throbbing cock to slide right in. I want t...
  • Raunchy Shemale Seeking Local Man for Wild Fun and Hot SexRaunchy Shemale Seeking Local Man for Wild Fun and Hot Sex Are you ready for a wild time with a sexy shemale in Janesville? I'm Micki and I'm looking for a man who can handle all of me. I love to get down and dirty, exploring each other's bodies in the most intimate ways. I'm a top who loves to take control, but I also enjoy being your submissive bottom i...
  • LetLet's Spark Some Magic ✨ Hey there! I'm Kacy, a fun-loving transgender gal from Wausau, Wisconsin. I may not fit society's traditional mold, but that's what makes me unique and special. Being part of the LGBTQ community has brought so much joy and acceptance into my life. I'm looking for someone who is open-minded, kind-...
  • Raunchy Shemale Seeking Hot Man for Wild Fun in MilwaukeeRaunchy Shemale Seeking Hot Man for Wild Fun in Milwaukee I love getting down and dirty with a man who can handle all that I have to offer. My name is Sarajane, and I am a shemale looking for a local guy who wants to explore all of his wildest fantasies with me. From top to bottom, I'm ready to play and make you cum like never before. I enjoy giving sl...
  • Looking for Love and Adventure in Janesville! Hey there, lovely people of Janesville! My name is Marcela, and I'm here to find someone special who appreciates me for who I am. 💕 So, let me tell you a little bit about myself. I have a curvy body that loves to dance and have fun. My ethnicity is a beautiful mix of cultures, making me feel l...
  • Seeking Local Man for Raunchy Shemale FunSeeking Local Man for Raunchy Shemale Fun Are you ready to have the time of your life with a sexy shemale in Eau Claire, Wisconsin? My name is Gabriela and I am looking for a man who can handle all of my wildest desires. I love being both a top and a bottom, giving blowjobs, getting my ass played with, sucking cock, riding tight dicks, an...
  • Naughty Shemale Looking for Hot Fun in WausauNaughty Shemale Looking for Hot Fun in Wausau Are you ready to get down and dirty with a sexy shemale like me, Lyssa? I'm on the hunt for a local man who can handle all of my kinky desires. I love to suck dick, ride cock, and gag on throbbing members. If you're into ass play, sloppy blowjobs, and intense orgasms, then we're a perfect match! ...
  • Elegantly Transcendent Iris Seeks Connection in MilwaukeeElegantly Transcendent Iris Seeks Connection in Milwaukee Hey there! I'm Iris, a proud transgender woman from Milwaukee, Wisconsin. I may not fit society's mold of what a woman should look like, but that's what makes me unique and beautiful. Being part of the LGBTQ community has allowed me to embrace my true self and live authentically. I love explorin...
  • Sparkle with Lizabeth: Seeking Connection in MadisonSparkle with Lizabeth: Seeking Connection in Madison Hey there, I'm Lizabeth from Madison, Wisconsin. I'm a curvy, Latina transgender woman who loves exploring the LGBTQ community and embracing my true self. I find joy in connecting with others who appreciate authenticity and diversity. I enjoy spending time at local spots like the Chazen Museum of...
  • Sexy Shemale in Green Bay Looking for Hot FunSexy Shemale in Green Bay Looking for Hot Fun I'm a naughty shemale named Golda who loves to play with men in all kinds of dirty ways. I'm seeking a local guy who can handle my insatiable appetite for sex and fun. If you're into wild encounters with a tranny who knows how to please, then I'm the one for you. I enjoy getting down and dirty wi...
  • Looking for Love in Appleton / Oshkosh, WisconsinLooking for Love in Appleton / Oshkosh, Wisconsin Hey there! My name is Margarita, and I'm a proud transgender woman living in the beautiful cities of Appleton and Oshkosh, Wisconsin. 🌈 I believe that love knows no boundaries, and I'm excited to meet someone special who sees beyond labels and embraces their own uniqueness. Being part of the L...
  • Seeking Connection and AdventureSeeking Connection and Adventure Hey there, I'm Angel from Green Bay, Wisconsin. I love meeting new people and exploring the world around me. As a transgender individual, I embrace my identity and enjoy being part of the LGBTQ community. If you're looking for someone who is open-minded and adventurous, then I might just be the on...