Home > Madison, Wisconsin > Adult Service Providers > Transgender Escorts


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

  • February 28th, 2026
  • Explore New Heights Of Ecstasy With A Kinky Transgender Experience.Explore New Heights Of Ecstasy With A Kinky Transgender Experience. Hey sexy, I'm a transgender escort who's ready to get fucked like never before. Whether you're into a naughty in call session or a wild outcall adventure, I'm here to fulfill all your desires. My juicy ? is always eager for action and I know just how to use it to make you scream with pleasure. Let's...
  • Hard Cocked Trans Ready For Anonymous Pounding, Satisfaction Guaranteed. LetHard Cocked Trans Ready For Anonymous Pounding, Satisfaction Guaranteed. Let's Play! I'm a trans escort with a hard cock ready to anonymously fuck. Whether you want me to come over for an outcall or you prefer to visit me for an in call, I'm down for some good pounding. Let's explore our wildest fantasies together and make each other moan with pleasure. I'm open-minded and non-judgm...
  • Kinky Trans Ready To Get Plowed - In Calls/outcalls Available!Kinky Trans Ready To Get Plowed - In Calls/outcalls Available! I'm a trans escort who's ready to get plowed. I offer both in calls and outcalls for those who are looking for a good time. Whether you're into a sexy trans, transgender, transexual, shemale, ladyboy, crossdresser, or transvestite like me, I'm here to fulfill your wildest fantasies. Let's skip the s...
  • Sexy Trans Ready To Plow Ass, Offering In/out Calls. LetSexy Trans Ready To Plow Ass, Offering In/out Calls. Let's Play! I'm a trans escort who's ready to plow some ass! I offer both in calls and outcalls for those who are looking to have a good time. Whether you're into a kinky session or just want to relax and unwind, I'm here to fulfill your desires. Let's get together and have some fun ?. Don't hesitate to reach o...
  • February 27th, 2026
  • Sexy Transgender Babe Ready To Fulfill Your Wildest Fantasies Tonight.Sexy Transgender Babe Ready To Fulfill Your Wildest Fantasies Tonight. Hey, I'm a transgender escort who's up for a good time. I'm down to get my dick sucked and give you a night to remember. Whether you want to meet at your place or mine, I'm game for some fun. Let's explore your wildest fantasies together and make each other feel amazing. Don't be shy about what you ...
  • LetLet's Explore Our Wildest Fantasies Together - I'm Ready! Hey, I'm a trans escort and I'm down to fuck your ass real good. Whether you're into trans, transgender, transsexual, transexual, shemale, ladyboy, crossdresser or transvestite like me, I'm ready to pound you hard. I offer both in calls and outcalls for your convenience. Let's have some fun together...
  • πŸ’‹ Glam TS Goddess Ready for a Private, Unforgettable EveningπŸ’‹ Glam TS Goddess Ready for a Private, Unforgettable Evening I'm a TS beauty living in Madison or somewhere near by... I was born a male, however I always known I am a pretty girl. I love meeting guys for sex and having fun. View My Trans Madison Dating Profile!!πŸ’‹ Sex in Madison TONIGHT!!  HOT Transgender Lady Wanting πŸ’‹ Want TransSex? Transgende...
  • Kinky Trans Ready To Pound Your Ass All Night Long.Kinky Trans Ready To Pound Your Ass All Night Long. Hey sexy, I'm a trans escort ready to fulfill your deepest desires. I'm down to pound your ass like there's no tomorrow. Whether you're into transgender, shemale, ladyboy, or crossdresser action, I've got you covered. I offer both in calls and outcalls for your convenience. Let's get together and h...
  • Trans First Timer, or Simply Curious, YouTrans First Timer, or Simply Curious, You'll Feel Comfortable With Me. I'm Gorgeous & Discrete! 😘 Fully-functional 25 y/o Trans girl at your service! 😘 Let's get the physical stuff out the way first, so nobody is uncomfortable. I'm completely passable trans girl so feel free to take me out dancing or to a business dinner party. I have an amazingly sensuous model's body - toned and smooth. I'...
  • Throbbing Trans Cock Ready To Anonymously Fuck You Good, In/outcalls Available.Throbbing Trans Cock Ready To Anonymously Fuck You Good, In/outcalls Available. I'm a trans escort with a throbbing cock, ready to anonymously fuck you good. I offer both in calls and outcalls for those craving a wild time. Let's fuck, no strings attached. I'll make sure you leave satisfied and coming back for more. Whether you're into trans, shemale, ladyboy, crossdresser, or ...
  • 24 y/o Crossdresser Ashley 🍭 seeks Madison Man for Dates24 y/o Crossdresser Ashley 🍭 seeks Madison Man for Dates Crossdressing Companion in Madison I'm Ashley, a girly crossdresser here for to service a man completely. I do know what you like! I'm fun and flirty, sexy, clean and feminine. No drama or rudeness ever. Contact me for a same day appointment. I have a clean, safe place or I can come to your locatio...
  • Kinky Trans Ready To Give Head In Private Gloryhole All Night.Kinky Trans Ready To Give Head In Private Gloryhole All Night. Hey sexy, I'm a kinky trans escort who loves to give head in my private gloryhole. If you're looking for a good time, I'm your girl ? I offer both in calls and outcalls, so we can fuck wherever you feel most comfortable. Let's skip the small talk and get straight to the fun - I'm ready to fuck, dril...
  • πŸ’Ž Classy, Confident & Irresistible – Elite TS Companion AwaitsπŸ’Ž Classy, Confident & Irresistible – Elite TS Companion Awaits  πŸ“Œ Location: MadisonπŸ’Ž Want I'm Seeking: a male or Trans who want's to play naughty!!πŸ”₯ About Me: Hey, I am a stunning, sweet and playful trans beauty who loves to have a good time.. sometimes the naughtier the better. Maybe a drink a some fun after? What kind of things are you into? I'm...
  • Explore Your Wildest Fantasies With A Throbbing Trans Surprise Tonight!Explore Your Wildest Fantasies With A Throbbing Trans Surprise Tonight! Hey sexy, I'm a trans escort with a throbbing surprise between my legs. I'm all about drilling a man's ass and making him beg for more. Whether you prefer in calls or outcalls, I'll make sure you leave satisfied and craving for another round. Let's explore your wildest fantasies together and have a ...
  • πŸ’‹ Madison trans companion. Come find the secret in my panties!! πŸ­πŸ’‹ Madison trans companion. Come find the secret in my panties!! 🍭 NO BLOCKED NUMBERS PLZ - message me @GloriaTransXual. I'm Gloria and I have a big secret hiding in my panties and it's only for you and me to know about. I'm fully passable (voice and appearance) so you can take me out to a business get-together or a nice restaurant. Only you and I will know the sec...
  • Craving To Get My Ass Destroyed - LetCraving To Get My Ass Destroyed - Let's Explore Together! I'm a trans escort with a craving for getting my ass destroyed. Whether you're into a wild in call session or prefer the thrill of an outcall adventure, I'm ready to make your fantasies a reality. I love to fuck and be fucked, so let's explore our deepest desires together. As a [transgender/transsex...
  • Independent Shemale Escort MayaGrace in MadisonIndependent Shemale Escort MayaGrace in Madison MayaGrace here... I am a sexy and naughty shemale companion available in the Madison area. Travel possible upon agreement. I'm a total flirt and a tease. I will make you feel proud to be out with me and will leave you happy & relaxed every time! I always take my time and am never rushed! Forget...
  • Sensual Trans Ready For Anonymous Head - In/out Calls Available!Sensual Trans Ready For Anonymous Head - In/out Calls Available! I'm a trans escort who's up for some anonymous head. I offer both in calls and outcalls for those looking to have a good time. Whether you're into a kinky session or just want to unwind, I'm here to fulfill your desires. Let's get together and have some fun ?. I'm open-minded and ready to explore ne...
  • Trans Escort Offering NSA In Calls And Outcalls For Kinky Fun.Trans Escort Offering NSA In Calls And Outcalls For Kinky Fun. I'm a trans escort ready to NSA fuck. I offer both in calls and outcalls for a good time. Let's fuck, no strings attached. I'll make sure you leave satisfied and coming back for more. Whether you're into a kinky fantasy or just looking to release some stress, I'm here to fulfill your desires. Don't ...
  • Kinky Trans Babe Ready To Give Anonymous Head - Satisfaction Guaranteed!Kinky Trans Babe Ready To Give Anonymous Head - Satisfaction Guaranteed! I'm a trans escort who's down for some anonymous head. Whether you're into a quick in call or prefer an outcall adventure, I'm ready to please. Let's get straight to the point and have some fun together. I'm open-minded and love exploring new fantasies. ?? Don't be shy about your desires - I'm here ...
  • Ready To Plow Some Ass And Have A Good Time?Ready To Plow Some Ass And Have A Good Time? I'm a no-nonsense trans escort who's ready to plow some ass and have a good time. I offer both in calls and outcalls, so you can choose what works best for you. Whether you're looking for a wild night or just some casual fun, I'm here to make it happen. Let's get together and have a great time ?. My...
  • Trans Beauty Ready For Anonymous Head - Satisfaction Guaranteed!Trans Beauty Ready For Anonymous Head - Satisfaction Guaranteed! Hey, I'm a trans escort who's down for some anonymous head. Whether you're looking for a quick release or a long, satisfying session, I've got you covered. I offer both in calls and outcalls, so we can meet wherever you feel most comfortable. Let's get straight to the point - I'm here to fuck and h...
  • Mind-blowing Trans Escort Ready To Fulfill Your Wildest Fantasies!Mind-blowing Trans Escort Ready To Fulfill Your Wildest Fantasies! Hey, I'm a trans escort who loves giving mind-blowing blowjobs. Whether you want to relax at my place or have some fun at yours, I'm down for it all. With me, you can explore your wildest fantasies and experience pure pleasure like never before. Let's get together and have a good time - satisfaction...
  • Hung Black Shemale 🌟 Top or Bottom 🌟 visiting MadisonHung Black Shemale 🌟 Top or Bottom 🌟 visiting Madison My name is Lady Velvet. I am here to explore all your wildest shemale fantasies.✨🍭 Guaranteed, you will want more! πŸ’‹ Repeat customers are always welcome. I am an attractive and fit shemale well endowed with a full, thick 100% operationalπŸ† who can service you top or bottom. I'm into oral, ...
  • Throbbing Trans Cock Ready To Drill Your Tight Ass, In/out Calls.Throbbing Trans Cock Ready To Drill Your Tight Ass, In/out Calls. I'm a trans escort with a throbbing cock ready to drill your tight ass. I offer both in calls and outcalls for your convenience. Let's fuck together, exploring all your wildest fantasies. Whether you're a curious first-timer or experienced in the art of pleasure, I'll make sure you leave satisfied a...
  • Ebony TSπŸŒ™ Late Night Fantasy with a Stunning πŸ†Ebony TSπŸŒ™ Late Night Fantasy with a Stunning πŸ† TS ESCORT WITH NICE HUGE, HARD COCK 🍭 I WANT TO DRESS UP SUPER CUTE AND SEXY THEN I WANT US TO EXPLORE OUR WILDEST AND NAUGHTIEST FANTASIES - WHAT ARE YOUR BIGGEST TURN ONs AND FANTASIES?? 😈😈 MESSAGE ME HERE AND LET'S PLAN SOMETHING. EBONY/BLACK SHEMALE❀️BLACK CROSSDRESSER❀️WILLING...
  • πŸ’‹ Soft Lips, Sharp Style – Sophisticated TS Escort ExperienceπŸ’‹ Soft Lips, Sharp Style – Sophisticated TS Escort Experience FULLY FUNCTIONAL TRANSSEXUAL and guaranteed to satisfy, I'm a BIG BOOBIE TS ESCORT in Madison Call me up for the Best Experience Ever.. I promise you that babe... Let me make your fantasy a reality Full Clean, 420 Friendly β˜˜β˜˜πŸ’ŠπŸ’ŠπŸ’‰ WE CAN BOTH SUCK ON EACH OTHER.  πŸ‘€View ...
  • Sexy Trans Ready To Please - Mind-blowing Blowjob Guaranteed ?Sexy Trans Ready To Please - Mind-blowing Blowjob Guaranteed ? Ready for a mind-blowing experience? I'm a sexy trans escort who loves to please. I'm down for giving you an amazing blowjob that will leave you begging for more. Whether you're into in calls or outcalls, I'm here to fulfill your wildest fantasies. Let's get together and have some fun ? I can't wai...
  • Sensual Trans With Throbbing Cock For In/out Calls, Pure Pleasure.Sensual Trans With Throbbing Cock For In/out Calls, Pure Pleasure. I'm a trans escort with a throbbing cock ready to get fucked. I offer both in calls and outcalls for those who want to experience pure pleasure. Whether you're looking for a wild night of passion or just some intimate company, I'm here to fulfill your desires. Let's explore each other's fantasies an...
  • Kinky Trans Lover Ready For Bondage Play In Calls Or Outcalls.Kinky Trans Lover Ready For Bondage Play In Calls Or Outcalls. I'm a kinky trans escort who loves bondage play. Whether you want to be tied up or do the tying, I'm down for some wild fun. I offer both in calls and outcalls, so we can get naughty wherever you feel most comfortable. Let's explore our deepest fantasies together and make all your desires come true....
  • Explore Your Deepest Desires With A Rock Hard Trans Escort.Explore Your Deepest Desires With A Rock Hard Trans Escort. I'm a trans escort with a rock hard cock ready to destroy your ass. I offer both in calls and outcalls for those craving a good pounding. Whether you're curious or experienced, I'll make sure you leave satisfied. Let's explore your wildest fantasies together and have a mind-blowing time. Don't be sh...
  • Kinky Trans Ready To Plow, In Calls And Outcalls Available.Kinky Trans Ready To Plow, In Calls And Outcalls Available. I'm a trans escort who's ready to plow some ass. I offer both in calls and outcalls for those who are looking for a good time. Whether you're curious or experienced, I'll make sure to satisfy your needs. Let's fuck together ?. My main goal is to make sure you leave with a smile on your face and a sk...
  • Explore Your Deepest Desires With A Kinky Trans Companion Tonight.Explore Your Deepest Desires With A Kinky Trans Companion Tonight. I'm a trans escort who's down to anonymously fuck. Whether you're into a quickie or a long, hard session, I'm here for it. I do both in calls and outcalls, so we can get down wherever you're most comfortable. Let's explore our wildest fantasies together and make some unforgettable memories. No judgm...
  • February 26th, 2026
  • Sexy Trans Babe Ready To Fulfill Your Wildest Anonymous Fantasies.Sexy Trans Babe Ready To Fulfill Your Wildest Anonymous Fantasies. I'm a trans escort who's down to get fucked anonymously. Whether you want to pound me in your place or mine, I'm game for a good time. I love feeling every inch of you deep inside me, making us both moan with pleasure. Let's explore our wildest fantasies together and make each other cum like never b...
  • πŸ”₯ High-Heel Heat – Sensual TGirl Bringing the SparkπŸ”₯ High-Heel Heat – Sensual TGirl Bringing the Spark The Best TS Escort♥️  Some About Me: βœ”οΈ9” off hormones βœ”οΈ100% real and recents pictures βœ”οΈFIRST TIMER ARE WELCOME! βœ”οΈfitness body βœ”οΈFantasy's - fetish's. 🌟🌟VISITING 🌟🌟 -INCALL REGULAR SESSION -FULL SERVICE VIP GFE -INCALL🌟 TS MISSY 100% REAL βœ...
  • ✨ Petite but Powerful – Trans Princess Seeking a Special Gentleman✨ Petite but Powerful – Trans Princess Seeking a Special Gentleman I’m a very confident TRANS sugar baby who loves being admired - a trans woman who feels good just walking into a room... Life feels lighter when someone else handles the details now and then. Comfortable doesn’t mean quiet - it shows in how I move through moments like they’re ...
  • πŸ’„ Alluring TS Bombshell – Beauty, Brains & After-Dark FunπŸ’„ Alluring TS Bombshell – Beauty, Brains & After-Dark Fun I Live in Madison,I tend to be a bit shy over the phone (so be discrete!) , but very easy to connect with in person :)Real/Verified pics,  Great reviews. P411 Verified βœ… & OF=TsPrincessLoveBunny -My Pics are authentic, and I am verified on multiple platforms.If you want to learn...
  • 🌹 Exotic Trans Diva Offering VIP Treatment & Sweet Temptation🌹 Exotic Trans Diva Offering VIP Treatment & Sweet Temptation Madison TGIRL and Want to have some sexy fun tonightWell Hung... 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 with local T...
  • 😈 Sultry TGirl with a Wild Side – Are You Ready to Play?😈 Sultry TGirl with a Wild Side – Are You Ready to Play? You Will Obey and Be Owned – I'm a very Dominant and secure Sexy TS... I'm a bit kinky passionate discreet fun loving hot tranny wants to have some fun today so if you're looking for a hottie let this tranny have some fun with you and fulfill your fantasies I'm Ashley Merree call or text...
  • πŸ”₯ Jessica.. Trans Beauty in Town – Let’s Make Tonight LegendaryπŸ”₯ Jessica.. Trans Beauty in Town – Let’s Make Tonight Legendary TS Jessica ( Real Shemale Escort )  come have some fun 😍 I'm ready for watever ! Best BJ of your life!!! πŸ‘… foreal baby looking to have a good time and i will please my daddy so if your looking for a good time call me plz be serious when contacting me dont call playing with me Text or Mess...
  • LetLet's Make Your Wildest Fantasies Come True - Satisfaction Guaranteed! Ready to get fucked? I'm a trans escort who loves to get pounded hard. Whether you want me for in calls or outcalls, I'll make sure you have a good time. Let's explore your wildest fantasies together and make some unforgettable memories. I'm open-minded, discreet, and always ready to please. Don't b...
  • February 25th, 2026
  • Hot Shemale Ready To Destroy Your Ass - Book Me Now!Hot Shemale Ready To Destroy Your Ass - Book Me Now! I'm a sexy trans escort with a rock hard cock ready to destroy your ass. I offer both in calls and outcalls for those who want to get pounded by a hot shemale like me. Whether you're curious or experienced, I'll make sure you leave satisfied and begging for more. Let's explore your wildest fantasies...
  • Seeking Anonymous Head? Trans Escort Ready To Please Your Desires.Seeking Anonymous Head? Trans Escort Ready To Please Your Desires. Hey, I'm a trans escort and I'm down to get some anonymous head. Whether you're into getting your dick sucked or giving head, I'm ready to please. I do both in calls and outcalls, so we can meet wherever you feel comfortable. Let's have a good time together and explore our wildest fantasies. I love ...
  • Ready To Get Plowed? Trans Escort Offers In/out Calls, Kinky Fun!Ready To Get Plowed? Trans Escort Offers In/out Calls, Kinky Fun! I'm a trans escort who's ready to get plowed. I offer both in calls and outcalls for those looking to have a good time. Whether you're into a kinky session or just some good old-fashioned fun, I'm here to make your fantasies come true. ? Let's explore our wildest desires together and make some unfor...
  • TRANNY PORNSTAR - Fun & Freaky in MadisonTRANNY PORNSTAR - Fun & Freaky in Madison Tranny Pornstar, A Very ELITE, Fun & Freaky transsexual hottie. I've been seen all over the web and known for always pleasing. I'm completely versatile Top or Bottom, Aggressive or Submissive, naughty or nice (naughty is especially nice)! I am a trans woman who loves to be pampered....but above...
  • Kinky Shemale Ready To Make Your Wildest Fantasies Come True!Kinky Shemale Ready To Make Your Wildest Fantasies Come True! I'm a trans escort ready to plow some ass and make your wildest fantasies come true. I offer both in calls and outcalls, so we can fuck wherever you feel most comfortable. Whether you're looking for a kinky shemale experience or just want to have a good time with a sexy ladyboy, I'm here to satisfy ...
  • LetLet's Skip The Small Talk And Get Straight To The Fun. I'm a trans escort who's down to give you some anonymous head. Whether you want me to come to you for an outcall or you prefer swinging by my place for an in call, I'm ready to satisfy your needs. Let's skip the small talk and get straight to the fun. I'm open-minded and always up for a good time. S...
  • Explore My Kinky World At My Private Gloryhole, LetExplore My Kinky World At My Private Gloryhole, Let's Play! Hey babe, I'm a transgender escort with a throbbing surprise waiting for you at my private gloryhole. I love giving head and getting down and dirty in all kinds of ways. Whether you want to come over for an in call or have me visit you for an outcall, I'm ready to fulfill your wildest fantasies. Let...
  • Come Get Your Mind Blown At My Private Gloryhole Playground.Come Get Your Mind Blown At My Private Gloryhole Playground. I'm a trans escort who loves to give head in my private gloryhole. Whether you're looking for some discreet fun, I offer both in calls and outcalls. I'm down for a good time and always ready to please. Let's get together and have a wild time together. ?? Don't be shy, let's explore our deepest desir...
  • The Best HUNG versatile top TS in Wisconsin πŸ†πŸ’¦The Best HUNG versatile top TS in Wisconsin πŸ†πŸ’¦ Fully functional trans companion, available for booking. Who’s gonna try all this hung WONDER & REAL! Sugar Daddy, VIP. UPSCALE Professional Gentlemen. Contact: Chat and contact @HungTransGrrlXXX I’m a high-maintenance trans woman, smell good, look good, and FUCK GREAT!! πŸ†πŸ...

  • Home > Madison, Wisconsin > Adult Service Providers > Transgender Escorts