Chicago, Illinois Shemale Sex Service Providers

Chicago, Illinois shemale sex service providers. Find local crossdressers, transexuals and shemale sex providers including shemale escorts, body rubs, strippers, dom & fetish and more. Select your location below to find shemale sex providers near you. It's free to search or post your own ad!

Home / Shemale Sex Services /

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

  • February 2nd, 2026
  • Your Naughty Little Secret Awaitsโ€ฆChicagoYour Naughty Little Secret Awaitsโ€ฆChicago Want a dance with a shemale stripper??  Some secrets are too good to keep… I’m one of them baby, and I’m  trans. ๐Ÿ˜˜ I’m the trans bombshell you’ve been dreaming about, they said, sexy,  confident, and always ready to play. Escape with me to a world of...
  • I want to be your whore tonight!...I want to be your whore tonight!... I am Paula, an ebony transexual escort in Chicago, 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 Chicago area. To book a naught night out just Click here and come see me anytime! - Paula69...
  • Chicago Transsexual ๐Ÿ’ฆ Wet Goddess ExperienceChicago Transsexual ๐Ÿ’ฆ Wet Goddess Experience  My name? Doesn’t matter. You will never forget what I do to you ๐Ÿ˜˜ View My Profile and Message Me -  I provide sensual and erotic massage services where bodies intertwine and time stands still. The nuru slides I  provide cover your entire body while being sensual and soake...
  • Upscale Asian Trans Escort New in Chicago...Upscale Asian Trans Escort New in Chicago... I am Jang-Mi your trans escort from Seoul, Korea new in Chicago. I love American men and the way they treat a lady. I am classy, exotic and am for men of taste. You will find me warm, a little shy, submissive, sexy and a hot lover behind closed doors. I do incall, outcall, travel, parties, conventio...
  • Chicago - ๐Ÿ”ฅ TS Temptation TouchChicago - ๐Ÿ”ฅ TS Temptation Touch  You will find me different from other body rub babes because I am the trans temptation which has been  on your mind. My expert hands and full lips and soft curves will provide you body massage experiences you  never had before. view my sexy trans profile here - The nuru gel serves ...
  • Online Cam Fun? Then Maybe Hookup? ๐Ÿ‘„๐Ÿ’ปOnline Cam Fun? Then Maybe Hookup? ๐Ÿ‘„๐Ÿ’ป  I am a trans woman living in Chicago and I am open-minded and always ready  to explore. What do you want to know about me? Let’s chat first—cam to  cam—and see if there is a connection. ๐Ÿ”ฅ She/Her, and all about making fantasies come  true. Let’s get wi...
  • Your TS Cam Crush is Ready to Connect โ€“ Come Play ๐Ÿ’ฆ๐Ÿ’‹Your TS Cam Crush is Ready to Connect โ€“ Come Play ๐Ÿ’ฆ๐Ÿ’‹  Seeking a smart trans girl who can turn you on with her smile and voice? Look no  further ๐Ÿ˜˜ I’m a TS woman with soft curves, a curious heart, and a dirty  little secret. I use She/Her pronouns and I love sharing raw, real moments on cam  — the kind that make your...
  • Want to See ๐Ÿ‘€ BBC Shemale Cock?? ๐Ÿ†Want to See ๐Ÿ‘€ BBC Shemale Cock?? ๐Ÿ† You Want Some Black Shemale Cock?? ๐Ÿ’‹ I'm in the Mood for some super sexy and naughty sexโค๏ธI'm available now and ready for you..  I am a sexy black Shemale with a nice big cock for you to play with..Let's take turns making each other cum ๐Ÿ†๐Ÿ† ๐Ÿ’ฆ Get in Touch With Me Now ...
  • February 1st, 2026
  • Letโ€™s Talk Naughty Firstโ€ฆ Then See Where It Goes ๐Ÿ˜‰Letโ€™s Talk Naughty Firstโ€ฆ Then See Where It Goes ๐Ÿ˜‰  Hey there! I am a sexy trans girl in Chicago who is all about real  connections with a fun, naughty twist. ๐Ÿ’‹ I am totally open to a meet up, but  I love to break the ice over cam first. Let’s explore each other, talk, tease,  and let the chemistry build. She/Her, fully ...