Madison Transgender Classifieds

Browse Madison transgender classifieds to meet local transexuals, crossdressers and shemales for sex, dating or friendship. Contact any of these trans advertisers to swap pics and contact info. Chat online or text and arrange real-time sex hookups if you feel a connection. It's free to search all trans classifieds, or post your own adult ad!

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  • May 25th, 2025
  • Strict Shemale Dominatrix in Madison - @DesireeTransDommeStrict Shemale Dominatrix in Madison - @DesireeTransDomme Powerful African-Queen Dominatrix in Madison I am full-time professional Domme Desiree. My Madison area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you will learn to...
  • Elisabeth waiting to be your QueenElisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Madison AREA Hi baby! I am waiting to meet you. I can host or travel to you. Down to earth preop transexual woman seeking an understanding man who can appreciate my uniqueness. I am a great cook and great fun! Let your hair down and allow me to pamper you and show you what...
  • Hot sexy shemale doll visiting Madison now Hot sexy shemale doll visiting Madison now Shemale Visiting Madison Very hot sevy and curvy shemale chick with big delicious lady stick, fully functions for top or bottom. Message me on my profile page @TaylaShemale1. Seeking a kind gentleman for romance and fun. I adore introducing men who are new to shemale sex. HMU! Possible long t...
  • πŸ†πŸ’¦Wisconsin Shemale Needing SexπŸ†πŸ’¦πŸ†πŸ’¦Wisconsin Shemale Needing SexπŸ†πŸ’¦ Sexy Shemale  πŸ‘„πŸ‘„Needing sex  in Wisconsin Wisconsin πŸ“²  Dating App  I'm new to Wisconsin but I know how to use my nice cock and make you cum with it. I'm a transsexual or sometimes reffered to as a Shemale and I still have my nice cock and nice big boobies. Would y...
  • Penny for your thoughts?Penny for your thoughts? Penny TS in Madison 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 @PennyTSswitch!! I'm a mixed race sweetheart, looking for a nice man who will enjoy being with me. Let's enjoy having some fun, hot dates and ex...
  • 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...
  • II'm a Horny Shemale πŸ˜ˆπŸ’‹ Looking For Sex Tonight!! Sexy ShemaleπŸ’Ž Ready to Rock Your World! Local Transsexual - TGIRL Sext App πŸ“² I'm a Transgender and I'm looking for a naughty man with a nice cock here in near me.. Who is wanting to share some sexy fun with me. I've been really horny and hard!! I love taking cock and giving it, what are...
  • 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...
  • I’m a Sexy and Naughty T-Girl Here in Madison.I’m a Sexy and Naughty T-Girl Here in Madison. Madison T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Madison area. Sweet, sexy, friendly and outgoing. I will definitely make you feel happy/sexy vibes and relaxed. I have an amazing body boys. I'm a pretty t-girl with a big present! So forget all your  worries and st...
  • Do you know the difference between a dick and a bucket of popcorn?Do you know the difference between a dick and a bucket of popcorn? You don't know? Well then take me to the movies baby! Mmmm think of all that creamy, buttery, salty goodness! Talk about a double feature. lol Hope you have the munchies for this hot Madison tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer than...
  • 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...
  • New Body New MeNew Body New Me M2F in Madison Hi, I'm Natasha, newly transitioned, exploring this beautiful new chapter in my life, and ready to date. Gorgeous non-op with slender legs and curvy body. Want to come and join me for a drink? I love sex in my new gender!!! Seeking a local area man who will enjoy sex and passion with...
  • 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...
  • Ebony TS Playmate for Men Who Know What They Want πŸ–€πŸ†Ebony TS Playmate for Men Who Know What They Want πŸ–€πŸ†  If you are the type of person who does not want to waste time with games or small  talk… we are already off to a good start 😘 I am a sexy, curvy TS  babe who loves attention, loves giving pleasure, and lives to be desired. I will come looking like  a dream and be read...
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Madison 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 and say hi!&nb...
  • TS Sugar BabyπŸ’Ž Your Perfect Trans Fantasy – Let’s Make It a Reality πŸ’‹TS Sugar BabyπŸ’Ž Your Perfect Trans Fantasy – Let’s Make It a Reality πŸ’‹  πŸ“ Location: Madison πŸ’– Seeking: Fun, Exciting, &  Discreet Connections Some about me.. Trans SugarBaby: Hey there! I belive I'm a stunning, sweet, and playful trans beauty who loves good  vibes, great chemistry, and unforgettable nights.. I'm in my early 20's and I'm...
  • 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,...
  • 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 ...
  • May 24th, 2025
  • Beautiful Krystale 25 Madison visiting nowBeautiful Krystale 25 Madison visiting now Beautiful Preop Shemale Visiting Madison Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me @Krystale25shemale.  Krystale25shemale Username: @Krystale25shemale Age: 25 Location: Madison, Wisconsin Sex: MtF Trans Seeking: Man ...
  • 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...
  • 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 ...
  • DonDon't Worry I Bite! Feisty redhead trans in Madison full of fun and loves it rough on the bottom. I'm 5'9, 170 pounds, 32 years old, well endowed, fully functional, passible and hot to trot. You can take me anywhere, but I can't promise to always behave. I have a dirty mind and when the urge hits it's hard to control m...
  • 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 Trans Profiles  &...
  • Latina TS Dirty Girl Looking for a GentlemanLatina TS Dirty Girl Looking for a Gentleman's Dark Side πŸ”₯πŸ‘   Sweet on the surface. Filthy underneath. View My Trassexual Dating Profile Here - As a TS darling I present like a dream while  playing like a fantasy. Stockings. Heels. A tight dress. Soft skin. And a  throbbing surprise you’ll love exploring 😘 I need you to undress me gr...
  • 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, with a great body and busty. Hit me up @SweetJasminT. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for a fun date and see where it goes! I'm preop and functional, very sex positive and love all sorts ...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Madison Tammy, 39, big tits!! Well hung, everything works, clean and so cute!! What more could you want in a gurl?!! How about you message me @Tammy39T and we can talk and meet! Send your recent pic for mine. Username: @Tammy39TLocation: Madison, WisconsinAge: 3...
  • Well Endowed Shemale is beautiful Madison 32Well Endowed Shemale is beautiful Madison 32 Well Endowed Shemale in Madison I am Blanca. I am ready to eat your manhood now. Top or bottom. Bareback if you're clean. Come say hello. I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me @BlancaShemale32 with your recent pic or selfie for my latest pictures and pr...
  • Hi Guys!! 32 y/o Trans looking for someone fun!Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Madison for Man Hello, thanks for looking at my ad! I'm Lara. I am 32 years old and transitioned when I was 24 but no surgery other than breast augmentation and some minor body touchups. I pass exceptionally well, fully functional. I'm feminine and classy so you will be pr...
  • 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 ...
  • Black/Ebony Transsexual - Your New  Addiction – One Taste and You’ll Beg for More πŸ‘πŸ’‹Black/Ebony Transsexual - Your New Addiction – One Taste and You’ll Beg for More πŸ‘πŸ’‹  Warning: I’m addictive 😘 View My Ebony TS Profile here - I possess more than attractive features. I am a complete  TS woman who enjoys teasing and pleasing while taking control of your dreams. My body features long legs and  thick thighs and soft lips and a hidden secret th...
  • 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 ...
  • May 23rd, 2025
  • 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 ...
  • TS Temptress Ready to Ruin You (In the Best Way) πŸ˜ˆπŸ’¦ MadisonTS Temptress Ready to Ruin You (In the Best Way) πŸ˜ˆπŸ’¦ Madison  Hey lover 😘 I’m a high-femme TS bombshell — curves for days, lips  made for kissing (and more), and a hunger that doesn’t quit. After dinner I appear sweet  but I transform into a woman who crawls to the bed naked while wearing only a mischievous  expression...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in MadisonSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Madison Secret Crossdressing Hookups in Madison Hey there. I'm Sam (Samantha when dressed up). If you're reading this ad you may be a crossdresser who needs to let your feminine side out to play. Me too! If you're in the closet or married, it's no problem. I live alone, have a nice, home with a private gar...
  • The Trevor Project Saves Young LGBTQ+ LivesThe Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project Proudly sponsored by Madison Lesbian, Gay, Bisexual & Trans Dating Community The Trevor Project Donations, by Megan Morrison BonePage.com proudly supports The Trevor Project, an organization dedicated to suicide prevention among lesbian, gay, bisexual...
  • Transgender Goddess for Late-Night Escapes & Filthy Fun πŸŒ™πŸ’‹Transgender Goddess for Late-Night Escapes & Filthy Fun πŸŒ™πŸ’‹  It’s late. You’re restless. And you’re craving something… different 😏 - View My Transsexual Dating Profile - As  your TS fantasy girl I offer sultry and smooth vibes while delivering experiences beyond what your ex could have  imagined. My secret between...
  • Crystal, 27 New to the areaCrystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Madison area and want to make some new friends! I am a masseuse, hot body, in great shape, and well hung. If you want to get together, Send me a private message Crystal27trans <3  Username: @Crystal27transLocation: Madison, WisconsinAge: ...
  • I Need a STEAM ROLLER Baby!!!I Need a STEAM ROLLER Baby!!! I want you to inject my soul with that sweet lover's pole till there ain't much of me left behind. I'm your whore so just F my brains out tonight. I'm a naughty trans looking for a top big boy to have his way with me. So it's heels and ass up and earth moving sex the hard way. That's the way I like ...
  • Email Madison Shemales Now! πŸ’ŒEmail Madison Shemales Now! πŸ’Œ Want to Hookup and Find Madison Shemales? RADE PIX - MESSAGE - BROWSE PROFILES This Website Helps you find local shemales and TGirls meet local men. It's the perfect place to find what you're interested in πŸ˜‰.. Do you want to meet local shemales who want to fuck and have some sexy fun? I dar...
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy  Madison!HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Madison! LET'S TAKE CARE OF THAT TRANNY FANTASY! "Experience your secret tranny desires in real life!"  Hot shemale Gia wants to hook up with you in Madison!  No strings - just great times, so join my page free for instant access! Shemale Gia's Madison Sexbook @ShemaleGia27 Photos: 42 V...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Madison Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Madison to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enjoy 24/7 Online Chat M...
  • Free Wisconsin Transexuals GuideFree Wisconsin Transexuals Guide Wisconsin Transexuals Guide The Wisconsin Transexuals Guide was prepared by our trans experts at AmericanTransexuals.com. We bring trans women and admirers together for friendship, dating and sex hookups. View our free Wisconsin Transexuals Guide online.  Where to Meet Transexuals in W...
  • 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 my wife doesn't approve. I REALLY need to let my fem side out to play! I'm seeking cross dressing...
  • May 22nd, 2025
  • 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...
  • Tiffany Shelle - Your Madison Tranny Girlfriend! πŸ’žTiffany Shelle - Your Madison Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Madison It’s Tiffany Shelle your perfect tranny girlfriend πŸ₯° πŸ’• SAFEπŸ’• πŸ’― LEGIT βœ¨πŸ’ž SKILLED, Exotic and Erotic πŸ’¦ πŸ₯° I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% functionin...
  • 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...
  • Erotic exotic Asian queen in Madison now (25)Erotic exotic Asian queen in Madison now (25) Asian Transexual in Madison Stunning TS - Talia 25. Asian mixed race, non op, loves sex. Nice build with long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information. Classy in public but trashy in the bedroom. Versatile and attentive to your needs. Longte...
  • Email Madison Shemales❀️‍πŸ”₯Email Madison Shemales❀️‍πŸ”₯ I'm a well hung TGIRL and Want to have some sexy fun tonight.. 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...
  • 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...
  • Road Head Sally DrivinRoad Head Sally Drivin' Hard in Madison Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Madison. Hey, what's the best time for road head? When there's gas in the tank baby! Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or park...