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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April 20th, 2025

TS Temptress Ready to Ruin You (In the Best Way) 😈💦 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...

🍆💦Wisconsin Shemale Needing Sex🍆💦 Sexy Shemale  👄👄Needing sex  in Wisconsin Wisconsin 📲  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...

I'm a Horny Shemale 😈💋 Looking For Sex Tonight!! Sexy Shemale💎 Ready to Rock Your World! Local Transsexual - TGIRL Sext App 📲 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...

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 ...

Brandi 27 tall slim hot trans chick fully functional 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 big functioning ladyclit for top or bottom. I love oral sex!! Kink friendly, have toys to explore all yo...

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...

FtM 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...

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 ...

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...

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...

Road 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...

Free 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...

April 19th, 2025

Email Madison Shemales❤️‍🔥 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...

Hot sexy shemale doll visiting Madison now Shemale Visiting Madison Very hot sevy and curvy shemale chick with big delicious lady stick. Message me on my profile page @TaylaShemale1. Seeking kind gentleman for romance and fun. Possible long term with the right man. ...

I'm the Girl Your Mum 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...

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...

Flawlessly 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 short and cute and I have bedroom eyes and luscious lips. Check my profile pics @TransFaye24 pics and prepare to be stunned! Send ...

Latina TS Dirty Girl Looking for a Gentleman's Dark Side 🔥👠  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...

Don'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...

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...

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 ...

Spicy 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...

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 ...

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...

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 ...

M-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....

F/M seeking love and fun Female to Male Trans Man in Madison My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and other times I let it gro...

Tiffany Shelle - Your Madison Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Madison It’s Tiffany Shelle your perfect tranny girlfriend 🥰 💕 SAFE💕 💯 LEGIT ✨💞 SKILLED, Exotic and Erotic 💦 🥰 I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% functionin...

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 ...

New Body New Me M2F post-op in Madison Hi, I'm Natasha, newly transitioned and ready to date. Gorgeous red head 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 me. Message me online Natasha...

SECRET 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...

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!! I'm looking for a nice man who will enjoy being with me. Let's enjoy hot dates and explore sexuality together. If that sounds interesting hit ...

Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Madison? Hey, I am Jasmin, 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...

April 18th, 2025

Well 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 at BlancaShemale32 for my latest pictures and proof of my size!&nbs...

Trans 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...

Don'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 🍑💋  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...

Strict 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...

Dr 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...

Having fun and Staying Young Young trans fem looking for nice date with lady. I am kind and thoughtful and you will have a very good evening if I take you out. Let me know what you want to do or where you want to go. View profile and message me xoxo, Sherry....

!!!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...

Beautiful Krystale 25 Madison visiting now Beautiful 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 Age: 25 Location: Madison Sex: Shemale Seeking: Man ...

I want to be a whore I am a transexual very hot. Good with my mouth and my ass. Comment on my photos. I would appreciate it if you downloaded my photos and share me with other men in the Madison area. Click here and come see me anytime!...

Sexy 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....

Crystal, 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 masseur, hot body and hung. If you want to get together, Send me a private message Crystal27trans <3 ...

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,...

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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...

Debonair Trans dude, looks like Bond F2M Trans Dude in Madison 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.&n...

Ebony TS Playmate for Men Who Know What They Want 🖤🍆  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...