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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January 17th, 2026
Selena 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 @SelenaIsTrans and send me a message to set up a date. I like going out for food or drinks, having a great time and I especially like great sex! I am preop and can do top or bottom though I kind of prefer top ...
January 16th, 2026
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...
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...
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...
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...
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...
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 ...
January 15th, 2026
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 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: ...
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 ...
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...

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