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!

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  • September 20th, 2026
  • MALE SEEKING SHEMALE πŸ†Madison Ready to Play and Fuck πŸ’¦MALE SEEKING SHEMALE πŸ†Madison Ready to Play and Fuck πŸ’¦ I have a secret.. 🀫 I've always want to see what it's like to play with a shemale!!  Hi I'm John, I'm in Madison  and I love to be free and have fun.. Are you looking for a man who really knows how to treat you?? I really want to show you what I got sweetie. I have a good heart an...
  • I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Madison )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Madison ) Sexy Crossdresser Elissa Looking for Hot Fun in MadisonπŸ’‹    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 and I am a p...
  • 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‘‘ Chocolate Queen with Soft Curves & Naughty Desires πŸ”₯πŸ‘‘ Chocolate Queen with Soft Curves & Naughty Desires πŸ”₯  πŸ”₯| 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 ...
  • Madison, Wisconsin Area πŸ† Shemale Seeking MaleMadison, Wisconsin Area πŸ† Shemale Seeking Male  Hot and kinky shemales available in Wisconsin; I am Alane and  I am here to fulfill all your desires. If you are in Madison, Wisconsin and  looking for a hot and kinky shemale to fulfill all your desires, then look no further for me. πŸ™‚ More about me...  All kinds of sexual a...
  • Flawlessly gorgeous trans bombshell in MadisonFlawlessly gorgeous trans bombshell in Madison Trans MtF for Man in Madison 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! Send your r...
  • Trans Playmate Sex Kitten...Trans Playmate Sex Kitten... Ebony trans woman in Madison 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 groups. I am ...
  • A monster in the sheets, but a lady in the streets...A monster in the sheets, but a lady in the streets... Hello men, I'm Lilith a 27 year old sexy femme, fully functional, passible, sexy and hot to trot trans. I can be a bit racy and dirty when it's appropriate, but always maintain my poise in public. If you live in the Madison area and are interested then drop me a line and introduce yourself. You can ...
  • Sexy Shemale Madison I know You Want to Play Sexy Shemale Madison I know You Want to Play FEMININE AND SECURE SHEMALE  Hot and kinky shemale seeking a hot and fun guy who isn't scared of a beautiful and secure Trans Woman.. I'm located in Madison; I am AlaneTS and  I am here to fulfill all your desires. If you are in the area or planning to be. and  looking for a hot and ...
  • 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 Madison 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 who lives ne...
  • Madison πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Madison 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...
  • 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 Madison 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 now. I'm sex...
  • Erotic exotic Asian queen in Madison now (25)Erotic exotic Asian queen in Madison now (25) Asian Transexual in Madison Stunning TS - Talia 25. 5' 8" 140lbs, non op, loves sex. Long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information....
  • SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now!SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now! HOT!  SHEMALE HOOKUPS  "The girl with a naughty little secret in her panties!" SIGNUP FREE: INSTANT ACCESS! Shemale Profiles Uncensored Photos Swap Your Pics Live Web Cams Private Messages Sext & Hook Up! Join free for Instant Access to the Shemale Profiles  ...
  • II'll Make You Feel Like a King Baby! Trans Queen Seeks King in Madison I'm queen Delilah a trans woman here in Madison searching for her king. You'll get the royal treatment when you're with me honey! Just grab hold of my magic scepter and his majesty can have anything he desires. Imagine the intrigue and scandalous position...
  • I Need a Sexy Man to Tame Wild Willy!I Need a Sexy Man to Tame Wild Willy! Hung Madison Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Madison 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 favorite Starbucks and see a ...
  • Madison Addicted to shemales... Male Seeking TSMadison 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 m/f switch 28 new hereTS m/f switch 28 new here TS m/f Switch in Madison Sandi wants to meet hot guy for fun and hot sex. Age 28, nice build, 7.5". Non op functional. Love oral sex, anal sex and kinks of all sorts. View my profile and message me here @SandiSwitchTS...
  • 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...
  • British T-girl Seeking Classy Gentleman in Madison...British T-girl Seeking Classy Gentleman in Madison... I am Lacy, a white, blonde haired, trans woman, 30 years old, 5'9, 160 pounds, from Manchester, England and need a man who is educated, refined and handsome. I have just relocated to Madison and am financially independent and looking for a gentleman who is like-minded, equally solvent and has except...
  • 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 M...
  • πŸ–€ Ebony TS Playmate with a Curvy Body & a Wild Side 😘 MadisonπŸ–€ Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Madison πŸ‘ Thick thighs, soft lips, and a wild side—what more could you want? I’m a sensual, passionate ebony TS beauty who knows how to make a man feel special, desired, and completely satisfied. Whether we take it slow and intimate or dive into a steamy, no-strings-attached night of passion,...
  • Brandi 27 tall slim hot trans chick 8.5 inchBrandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Madison Beautiful Brandi. If you're attracted to the female form then you will want to message me @ BrandiTS27.  I'm pre-op, tall, slim and beautiful with 8.5 inches for top or bottom. I love oral sex!! Kink friendly, have toys to explore all your naugh...
  • Seeking All TS Beauties in MadisonSeeking All TS Beauties in Madison  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...
  • MadisonMadison's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Madison Hi you sexy man! I'm Toni a trans woman from here in Madison. 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, hung, functional and loves...
  • Your Shemale Addiction 😈πŸ₯΅ Starts NowYour Shemale Addiction 😈πŸ₯΅ 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...
  • 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...
  • YOUR EBONY SHEMALE - big boobs and a BIG COCK! MadisonYOUR EBONY SHEMALE - big boobs and a BIG COCK! Madison Hot Hot Hot! Sinead, a black shemale in Madison 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  Madisonto fulfill all your dreams? Then stop searching because I am ready to make  all of your dream...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Madison 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....
  • 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...
  • TS Beautiesβ€”Let’s Make Some Memories πŸ’–βœ¨TS Beautiesβ€”Let’s Make Some Memories πŸ’–βœ¨  I am a dominant, attractive, and confident man looking for a beautiful transgender woman who enjoys being  admired, spoiled, and pleasured.  I am down for mutual attraction, passionate flames and unforgettable  moments. Whether it is a one time or if it is something on going I a...
  • She-male looking for hot date to please. She-male looking for hot date to please. Asian Shemale in the Madison Area Hot Asian shemale wants to date and please you in the art of erotic passion. I'm non op, fully functional, lovely and funny. Please to contact me @CarmelShemaleXXX. My name is Carmel. I'm 33 years old. I like to explore your sexual fantasies! Let's make them come ...
  • DonDon't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Madison Look no further honey, I'm Franny an Ebony trans woman here in Madison to fulfill your wildest fantasies. Dreams really do come true when you are with Fabulous Franny. I'm all about the frills and the thrills baby! We can freak it and they don't have to ...
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  • Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Madison Seeking!!Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Madison 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...
  • Smoke me out baby!Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Madison who doesn't smoke, but has a thing for sexy men smoking cigarettes. Call it a fetish or a kink if you will, but I love it. If done right it is soo sexy and inviting to my senses and gets my motor running every time. Truth is that it's erotic all in it's...
  • Flirty & Feminine CD Ready for Some Fun πŸ’•πŸ˜ˆFlirty & Feminine CD Ready for Some Fun πŸ’•πŸ˜ˆ  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.  πŸ’‹ πŸ’Ž Bath g...
  • Selena Trans girl cute looking for loveSelena Trans girl cute looking for love Hello boys. I am looking for love. You want meet me? I want meet you too. See my pictures and send message for date....
  • Let’s Get a Drink… and See Where It Leads 😘Let’s Get a Drink… and See Where It Leads 😘  One Night, No Limits...  MadisonShemale Seeking Man for sexπŸ’¦ View More of My Pix - βœ… Some nights are for breaking rules, for letting go, and  for indulging in pure pleasure.  I am a trans goddess with a wild side, and I  am looking for a man who wants to play. We sho...
  • Letha Aims to Fill YOU With Her Love Gun!!!Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Madison and I got a BIG love gun to whip and pound you with until you scream! I'm def top and alpha and don't take no shit! Imma make you suck me first just for foreplay then I'll throw you back for some hard insertion,...
  • Superb Shemale in Madison...Superb Shemale in Madison... T-Girl for NSA Encounters in Madison When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Madison. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle, f#ck and ...
  • Tantalizing Tina with a HUGE W33NAH!Tantalizing Tina with a HUGE W33NAH! Madison Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Madison men and wnat to show you a time you'll never forget! Do you like them thick, long and uncut? Then I'm the girl for you. Look no further for a passible and functional t girl - HERE I AM!  About me: 2...
  • September 19th, 2026
  • Flirty, Dirty, and Ready for Some Fun ❀️ Madison Shemale Seeking Male Flirty, Dirty, and Ready for Some Fun ❀️ Madison Shemale Seeking Male Local Shemale Seeks Man For Adventure!  TS Vixen, are you ready to play? Sweet, sultry and a little bit  wild, I am a trans goddess and I do enjoy my men to be as much as a wild  as I am. 😘I don’t want to talk – I want to try something a bit  more exciting. How ab...
  • INTERACTIVE MAP: Transexual Tracker in the Madison Area!INTERACTIVE MAP: Transexual Tracker in the Madison Area! Local Transexual Hookups Meet local transexuals in the Madison 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 Madison Trans Hookups Map ...
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Woman in Madison Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Madison. What kind of kink? You'll have to contact me to find out. I'm open to all sorts of fetish play if you are. I need a hookup with an open minded man. The sort of man who appreciates what ...
  • Local Crossdresser πŸ˜‰πŸ˜‡  LET ME PLAY DRESSUP FOR YOULocal Crossdresser πŸ˜‰πŸ˜‡ LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Madison View My Personal Pix - 🀫  A sexy Crossdresser from Madison, 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. If you like dirty games a...
  • Shemale 4 Men πŸ†πŸ’¦  Madison Ready Now!! Shemale 4 Men πŸ†πŸ’¦ Madison 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...
  • 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...
  • 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 Madison area come see if you measure up! Click here for explicit photos. Look f...
  • TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession πŸ˜ˆπŸ‘TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession πŸ˜ˆπŸ‘  Hola, mi amor 😘 The fiery, curvaceous TS Latina body I possess was  made for lust while my soul demands intense passionate nights. Your dream woman has arrived because I possess caramel  skin and thick thighs and long hair and soft lips and a throbbing surprise between my legs th...