Illinois Trans and Crossdressers Classifieds

Illinois trans and crossdressers classifieds - meet local trans women for dating, sex hookups or friendship. Browse transgender and crossdresser classifieds or post your own ad. Meet local TS/CD hotties to live your wildest fantasies!

Home / Shemale Dating / Trans And Crossdressers

Show Ads In: Bloomington-Normal | Carbondale | Champaign-Urbana | Chicago | Decatur | Peoria | Quad Cities, IA/IL | Rockford | Springfield, IL

  • August 13th, 2026
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Woman in Illinois Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Illinois. 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 wha...
  • Email Local Shemales Now! πŸ’ŒEmail Local Shemales Now! πŸ’Œ Want to Hookup and Find Local 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'reinterested in πŸ˜‰.. Do you want to meet local shemales who want to fuck and have some sex...
  • 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 Illinois area and are interested then drop me a line and introduce yourself. You can...
  • 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 Illinois 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 se...
  • M-F trans woman wants a dateM-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....
  • Tranny CockπŸ†ChicagoTranny CockπŸ†Chicago Transgender HOOKUPSin Chicago, Illinois πŸ†β€οΈπŸ˜‰  Check My Profile and and Dm MeI'm in the Chicago, Illinois.. area. I'm willing to travel. As longas you love TGirls and Shemales..I want to have some sexy hookups..I have some fun things in mind. I would loveto connect and see w...
  • 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 Illinois area come see if you measure up! Click here for explicit photos. Look ...
  • T-Girl Wants No Strings Fun in Chicagoland!T-Girl Wants No Strings Fun in Chicagoland! Hi I'm Mavin, and verybody says I look like Marlo Thomas an actress from the 1960's and 70's. I'm passible, functional, Ive been described as easy to talk to, comfortable to be around, and sweet in demeanor. I'm a good girl with needs though and want some NSA action in Chicago tonight. You...
  • 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 Illinois Area Hi, my fem name is Gloria. I'm a married crossdresser in the Illinois area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but wife doesn't approve. I really need to let my fem side out to play! I'm seeking cross dressing ...
  • Beautiful Krystale 25 Illinois visiting nowBeautiful Krystale 25 Illinois visiting now Beautiful Shemale Visiting Illinois 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: Illinois Sex: Shemale Seeking: Man ...
  • 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...
  • 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...
  • Super Barbie T-Girl Wants Hot Men in Chicago...Super Barbie T-Girl Wants Hot Men in Chicago... Hey sexy boys, I'm a trans woman looking for a man, forget about my intelligence, talent and great personality, I have something better to spring on you when the time is right. I aim to show you the time of your life and ride the weenie all night! Honestly I'm so horny I could do hand, oral, top or ...
  • FtM seeking Princess Bride in IllinoisFtM seeking Princess Bride in Illinois FtM seeking Woman in Illinois Hi, I'm Andy, age 33, FtM transgender man living in Illinois. 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 @AndyFtM...
  • Penny for your thoughts?Penny for your thoughts? Penny TS in Illinois 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...
  • Send Me Sext Messages...Send Me Sext Messages... I'll show you mine if you show me yours! If you like the show maybe we can get together for some real adult fun. I'm Nina, a trans lady looking for a man for NSA, 28 years old, Italian, bottom, functional and always extra horny. Please be in Chicago, clean, polite, fun and ready for some action. If ...
  • August 12th, 2026
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Illinois Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • Hot sexy shemale doll visiting Illinois now Hot sexy shemale doll visiting Illinois now Shemale Visiting Illinois Very hot sevy and curvy shemale chick with 8 inch lady stick. Message me on my profile page @TaylaShemale1. Seeking kind gentleman for romance and fun. Possible long term with the right man. ...
  • Tiffany Shelle - Your Illinois Tranny Girlfriend! πŸ’žTiffany Shelle - Your Illinois Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Illinois 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% functioni...
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy \ Illinois!HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Illinois! 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 Illinois!  No strings - just great times, so join my page free for instant access! Shemale Gia's Illinois Sexbook @ShemaleGia27 Photos: 42 ...
  • Single White Trans Woman Wants FWB in the Windy City..Single White Trans Woman Wants FWB in the Windy City.. I'm Hora looking for love in all the wrong places and lovin' every second of it! So here I am single and on this site looking for a sexy man to take me to loveland on a regular basis. (NSA) I expect you to be: not afraid to party, not afraid to go top, not afraid to go bottom, not afraid to take me ...
  • T-Girl-Tastic Tina With a Big...T-Girl-Tastic Tina With a Big... Hi honey, I'm Trans Tina here in Champaign-Urbana looking for some discreet action with a hot man who knows how to treat a lady right. I'll give you a taste of Tina's forbidden fruit and leave you wanting more. I'm 30 years old from here in Illinois, 5'9, well endowed, blonde, functional, singl...
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Illinois 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!&n...
  • Email Illinois Shemales❀️‍πŸ”₯Email Illinois 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...
  • Having fun and Staying YoungHaving 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....
  • August 11th, 2026
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Illinois? Hey, I am Jasmin, 8" 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...
  • Spicy and Hot T-Girl from ColombiaSpicy and Hot T-Girl from Colombia Latina T-Girl in Illinois 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...

  • Deprecated: preg_match_all(): Passing null to parameter #2 ($subject) of type string is deprecated in /home/shemalebackpage/public_html/classifieds/wp-content/plugins/cleantalk-spam-protect/lib/Cleantalk/ApbctWP/ContactsEncoder/Shortcodes/ExcludedEncodeContentSC.php on line 525

    Deprecated: preg_replace_callback(): Passing null to parameter #3 ($subject) of type array|string is deprecated in /home/shemalebackpage/public_html/classifieds/wp-content/plugins/cleantalk-spam-protect/lib/Cleantalk/ApbctWP/ContactsEncoder/Shortcodes/ExcludedEncodeContentSC.php on line 85