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TS Escorts & Shemale Escorts in Chicago, IL

Chicago, IL Activities
Nearby locations:
Rosemont, IL (7) | Elmhurst, IL (2) | Oak Brook, IL (3) | Mt Prospect, IL (1) | Schaumburg, IL (3)

TS Escort Of The Day

oliviarhodes
Manhattan, NY
I’m a pre-op trans woman visiting the area and looking to have some fun with someone special 😉 I’m open-minded, into all kinds of kinks, and always down to explore new experiences—especially if it pleases my man 😉 I’ll be here for the next two weeks and I’m available anytime, day or night. I’m feeling playful and would love to find a regular hookup ASAP! If this sounds like your vibe, hit me up on OF and let’s make it happen!! OF --> https://onlyfans.com/oliviarhodest/c2
View profile
oliviarhodes
Manhattan, NY
Available Now
Age
21 Y/O
I Am
Trans woman
Ethnicity
Caucasian
Baltimore
09 May - 23 May
Jersey City
23 May - 05 Jun
New York City
05 Jun - 19 Jun

ts4rent exclusive

Chicago, IL TS Escorts, Shemale & Trans escorts

  • Platinum Boost
    Sabrina_carter
    Chicago, IL
    Available Now
    Sabrina_carter
    I am Sabrina, ARGENTINA, a trans girl , young, delicate, soft and very hot, 25 years old. With a perfect smile, sweet lips, my clear eyes and my White skin very Erotic and seductive, I like to please and always keep control so that we both enjoy. I love to feel and give pleasure, I am 100% versa...
  • Platinum Boost
    MelXHottie
    Chicago, IL
    Available Now
    MelXHottie
    hi bby, my name is mel and im your versatile ts girl dream 😉 im on here looking for someone thats down to hookup any place, any day, anytime. im always down for fun and im always available to be somebodies fuck buddy 😉 im into all of the kinks, fetishes, fun and whatever your fantasy is.
  • Platinum Boost
    laralovexxx
    Chicago, IL
    Available Now
    laralovexxx
    Going to be completely honest I'm looking for somebody to have fun with. Either a fuck buddy or friends with benefits ;) Open to just about everything, the kinkier the better for me ;) and I will try ANYTHING at least once. Just looking for like minded, freaky and kinky people to have fun with. I...
  • Platinum Boost
    VioletXL
    Chicago, IL
    Available Now
    VioletXL
    I do not ANSWER CALLS(due to timewasters) only SMS/Imessage or on OF!!! ALERT! Trans content with a curved cock https://onlyfans.com/tsvioletxxx/c22 15%OFF MY PRIVATE DM IS OPEN! AND I ALWAYS ANSWER WHEN IM NOT BUSY WITH CLIENTS!! ALL OF MY CONTENT WILL BE UNLIFTRED WITH SO RESTRICTIONS & YOU KN...
  • Platinum Boost
    aribby
    Chicago, IL
    10 hours ago
    aribby
    Hi my name is Ari, standing at 5'10 with blue eyes and long blonde hair that give me an exotic look. Come have fun with me while I'm visiting! Very comforting, always discrete, and never rushed. Fansly fans.ly/AriellaWeiland
  • Platinum Boost
    Lovelyanna
    Chicago, IL
    Today, 06:08
    Lovelyanna
    I have a slim, tall, and toned figure, as I take care of myself. Educated, charismatic, and fun to be with! I’m full of energy and always ready for an exciting time! JOIN MY ONLYFANS : I have hot content, subscribing will make both of us feel safer and more comfortable. https://onlyfans.com/tschi
  • Platinum Boost
    TsArianaangel
    Chicago, IL
    09 May, 17:00
    TsArianaangel
    Hii I’m Ariana welcome to my page 🥰 23 year old, big booty trans girl . I look exactly the same in person or better some would argue 🥰 Let me fulfill your fantasies and take away from your worries. I would love to captivate your mind and tingle your senses, I will make you feel in your body and s
  • Platinum Boost
    TsAngelmoonx
    Chicago, IL
    09 May, 17:00
    TsAngelmoonx
    New girl on the block, and trust me, I’ve been waiting way too long to meet someone just like you 😈. I’m all about those deep, intimate connections that leave us both breathless. I’m playful, passionate, and maybe just a little too naughty for my own good. Let me show you what I’ve been fantasizing
  • dam2116
    LIVE
    dam2116 is now live
  • tssandy
    LIVE
    tssandy is now live
  • Platinum Boost
    Vvictoria
    Chicago, IL
    Available Now
    Vvictoria
    Hey there, Treat yourself to the most pleasurable fantasy that your body and mind could ever imagine. Our time together is never rushed. It will always be comfortable and discreet. I certainly look forward to meeting you,...
  • Platinum Boost
    Exotic_Vissa
    Chicago, IL
    10 May, 22:02
    Exotic_Vissa
    •Text me to set appt — include your photo to meet — ( no pic NO MEETING ) Prepare yourself for the most unforgettable night of indulgence and excitement. This is your invitation to leave all your worries behind and step into a world of boundless pleasure. Don’t be shy—this is a completely judgment-f
  • NoirSwan
    Chicago, IL
    Available Now
    Your intimate, taboo fantasies are celebrated here! My expertise is being a Dominant Kinky Girlfriend Mistress, there is nothing I adore more than being worshipped, pampered, and being around submissive lovers and slaves. I’m proudly a non-hormones using girl because I prioritize my organic sex d
  • Emily_love
    Chicago, IL
    Available Now
    NEW HOT GODDESS IN TOWN * READY WHENEVER YOU ARE —————————ALWAYS NON RUSHED————————— I PROMISE WE WILL HAVE A GREAT TIMETOGETHER DON'T BE SHY DON'T LET THIS MOMENT PASS YOU BY MY PICTURES ARE 1000% ACCURATE COMPARED TO OTHERS (PRINT THEM AND BRING THEM TO COMPARE)
  • TsPiiinkyPromise
    Chicago, IL
    Available Now
    Beautiful Creole Beauty Looking For Upscale Gentleman Only I Can Host Or Travel Sexy Facetime Shows Available Ask About My Smoking Hot 2 Girl Show All My Pics Legit and Updated Im Very Strict When it Comes To Hygiene I Hope You Are The Same
  • baby_grlstella
    Chicago, IL
    Available Now
    Young, fun, and full of… how does it go again? I’m educated, upscale, sweet, and sexy. I take pride in providing the ultimate TS experience. All my photos are real, recent, and always unedited! Discover why they tell me I look even better in person. Whether you’re a first-time client or simply cu
  • Teaforlexi
    Chicago, IL
    34 min ago
    ✨🌹Hi, I’m lexi. I’m outgoing, spontaneous 🌹ready to experience any new sexual desires I am fully functional. ready to squirt my load all over READY to TOP and eat that man hole!, highly intelligent Let’s have a good time. Either my place or my hotel I love a good old-fashioned dirty martini oh and
  • VIOXXL
    Chicago, IL
    39 min ago
    WE CAN MAKE A VIDEOCALLS before you coming to me i am 100% real *** HAPPY END ( 1 5 0 ) the rest it's more $$ I am STDS free 01/15/2025 Also I AM A PROFESSIONAL THERAPIST OF OVER 10 YEARS OF PRACTICING I HAVE A VERY NICE CLEAN STUDIO WITH A PROFESSIONAL *** TABLE IN MIAmi BEACH FREE PARKING ALSO M...
  • margauxx
    Chicago, IL
    Available Now
    An upscale companion. I am very selective when it comes to whom I share my time with. I only cater to a small number of high-quality gentlemen who are respectful, clean and generous. Screening is for my safety and is absolutely non-negotiable. the details that I request are used only to verify yo...
  • GigiRavine
    Chicago, IL
    2 hours ago
    Cultured, smart woman with a body to match. Used to think too hard and care too much, but gave it all up to live a fun, carefree life. 💃👯‍♀️🩰🪩🎊🎉🍾🍷I dance around the country. Chances are, that is why I’m in your town. Are you a betting man? 😈 🎲 🃏 Talk to me about wine. Dine me. Then, if we like
  • TSNikki
    Chicago, IL
    Available Now
    Any Booking Arrangements I do require a “Face Photo” 📌Booking Instructions: "Face Picture" is required (No Exceptions) Name Age City, State, Desired date, time and length of appointment Please provide all the info listed above when contacting me, otherwise I won't respond😉 🎥FaceTime Shows are als
  • GingerAnastasia
    Chicago, IL
    2 hours ago
    Tall Slavic redhead with a fully functional💦 model body ready to make your fantasies come true 😉 While discretion is always a top priority it is appreciated if you can send a picture of yourself. I am nda experienced and open to signing. I look exactly like my pictures and am available for FaceTi
  • Tsrosalia
    Chicago, IL
    Available Now
    Hey there!! I’m a 21 yr old latina transsexual visiting in your area!!! I’m here for a good time and to pleasure you in every way!! Don’t be scared to messaged or call me I don’t bite unless you want me to🙈 let’s have fun and live it up baby❤️ https://onlyfans.com/tsrosalia
  • Tssexysonia
    Chicago, IL
    Available Now
    The waiting is over Sexy SONIA is back the best provider in the Midwest is here The most naughtier and sexier always ready to unload all the stress away !! I’m ready to travel anywhere in the us I! Before contacting me not explicit text is tolerat
  • GFE_TSJENNY
    Chicago, IL
    Available Now
    My name is Jenny and I'm, 26 years-old tranny, 100% feminine, delicate, glamorous and sensual. I am your perfect choice, with an amazing beautiful body and a beautiful face, Both part of a harmonious atmosphere with nice qualities. Im 5'7 tall and 134 llbs.Warm and friendly,great with first timers....
  • Lealove
    Chicago, IL
    3 hours ago
    I love to maintain a toned sexy physique I love romantic dates, unforgettable moments filled Whit passion. I'm have black hair long , beautiful softly skin . My high 5'7 W 135 lbs Black eye Spectacular waist 28 * Call me now !!! Don't wait any longer The best of the rest . 773 - 742-1907 Kiss mu...