Chicago, Illinois Shemale Sex Service Providers

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  • July 12th, 2025
  • TS Girl Seeking Vibes, Cam Fun & Maybe Something Real 💖📲TS Girl Seeking Vibes, Cam Fun & Maybe Something Real 💖📲  Do you find attractive confident curvy trans girls who display a naughty smile and soft voice? You  already have my full attention 😘 The process of transitioning brings me great joy as I experience all  its wonderful aspects. She/Her stands as my preferred pronouns while I seek g...
  • Hot Chocolate Encounters of the Trans Kind Tonight in Chicago Baby!Hot Chocolate Encounters of the Trans Kind Tonight in Chicago Baby! Ebony Tgirl Escort in Chicago Dark chocolate t-girl escort here to rock your world in Chicago. I'll make you feel alright with my big goodbar tonight. I'm an animal baby just doin' what comes natural. I am discreet and welcome incalls and outcalls women, couples, gay men, groups and just about...
  • 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 escort in Chicago. I can be a bit racy and dirty when it's appropriate, but always maintain my poise in public. If you live in the Chicago area and are interested then drop me a line and introduce ...
  • Chicago Come See a Local Ebony Tranny Dance on The PholeChicago Come See a Local Ebony Tranny Dance on The Phole  Ebony TS Goddess Seeks a VIP Date! 💵💰💎  Hey boys, I'm an Ebony Transsexual in Chicago and I'm dancing tonight. Come hang out.. Let's have a few shows and maybe a dance. If you say you found me from this ad, I'll give you a SPECIAL DANCE!!! 👸💦 You like curves, confiden...
  • Local Trans Dancers! 🥵🥰 Local Trans Dancers! 🥵🥰 TS Angel with a Devilish Side…😈Come see me at the club tonight!  By looks of things I am an innocent girl but oh baby don’t let that sweet face fool  you I know how to play dirty. I can never get enough of a man who knows how to  have fun and the only thing I enjoy mo...
  • TS ( TRANS ) 💦 Nuru Dreams Come TrueTS ( TRANS ) 💦 Nuru Dreams Come True  Slide into something slippery, baby 😏 I’m a sensual trans goddess offering nuru massage that feels  like heaven and ends in ecstasy. My body will move across yours in a sensual gliding motion without  any friction as we connect skin to skin and heart to heart. View My Profil...
  • Horny Trans Cutie Online in Chicago – Let’s Chat First 🟢Horny Trans Cutie Online in Chicago – Let’s Chat First 🟢  Looking to meet someone real? I am a flirty, wild trans girl who is ready to  chat and see where things go. I get off on naughty cam convos and love to tease before  we take it further. Let’s heat things up and maybe plan a hot little meetup. Message  me, view my profile, ...
  • Independent Shemale Escort Top or Bottom in ChicagoIndependent Shemale Escort Top or Bottom in Chicago Top or Bottom Shemale Escort in Chicago Hey guys. I'm Maya Grace (@MayaGrace31). I am a sexy and sweet, but also naughty shemale in the Chicago area. I'm friendly and outgoing, a total flirt and a tease. I will definitely make you feel proud to be with me. I will leave you happy & relaxed every...
  • Killer Queen!Killer Queen! Chicago Trans Escort Playful as a Pussycat! Insatiable in appitite. I am Chicago's favorite trans escort, Paris. I am THE Killer Queen, dynamite with a laser beam. And I'm guaranteed to blow your mind - anytime! I am a cosmopolitan trans woman who enjoys the finer things in life, but have found tha...
  • ❤️😍 TS Tease Ready to Please—Meet Me Tonight!😍❤️ ❤️😍 TS Tease Ready to Please—Meet Me Tonight!😍❤️  Sassy & Classy in ChicagoCome Play with Me!  😍  Hey there sexy! 💋 I am your favorite trans bombshell dancing your fantasies of your  dreams. Get a private show for free at the club here in Chicago, I’ll be there turning up the  heat. Of course, drinks and l...
  • Seductive Roselia is excited to make your wildest dreams 💦 true ChicagoSeductive Roselia is excited to make your wildest dreams 💦 true Chicago SHEMALE BODY RUBS AND MASSAGE Located in Chicago - Stop on in! 👄😻    Looking for a Sexy and Sensual Massage from a TS/Shemale, in Chicago? Well search more! I'm Roselia ( SHE/HER ). I'm here to make sure you have a time with me ✨  As a transgender woman I love what I do...
  • Trans Goddess Seeking VIP Companion!💎💎Chicago💎💎 Hispanic Tranny Dancing TonightTrans Goddess Seeking VIP Companion!💎💎Chicago💎💎 Hispanic Tranny Dancing Tonight Spicy, Sultry & Down to Mingle!Hispanic and Spicy Latina TS 👗🔥 I don’t just dance, I seduce. 😏 If you love an exotic, trans beauty who knows how to tease, I’m waiting at the club and I'm bored.. Ughh, please come save me and let's have some fun. I want to take a few shots w...
  • Dr FreakinDr Freakin'Furter - Mine's Bigger Than Yours! White, 32 year old T-girl escort Freakin'Furter here in Chicago, 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 Chicago area come see if you measure ...
  • Naughty boys check me out - Good thing I love naughty boys - Your wildest fantasies will come trueNaughty boys check me out - Good thing I love naughty boys - Your wildest fantasies will come true Tara here, I live to make your fantasies come true in Chicago! I have a bubbly personality, enjoy intimate dinners, shopping, and I love as much as I receive. Fully passable, I dress to impress, STD free, classy, and ready to satisfy your needs and fetishes on short notice. I’m known for my se...
  • 24 y/o Crossdresser 🍭 seeks Man for Dates in Chicago24 y/o Crossdresser 🍭 seeks Man for Dates in Chicago Crossdresser Escort in Chicago Girly crossdresser Ashley here for to service a men and I do know what you like! I'm always fun and flirty and clean and very feminine. No drama or rudeness ever. Incall/outcalls available. Contact me for same day appointment. I have a clean, safe place or you name th...
  • INTERACTIVE MAP: Transexual Tracker in the Chicago Area!INTERACTIVE MAP: Transexual Tracker in the Chicago Area! Local Trans Hookups Meet local transexuals in the Chicago area for friendship or sex hookups. View our interactive map below to meet local trans members who want to meet local transexuals or admirers. Click a thumbnail to get started now! Interactive Chicago Trans Hookups Map ...
  • SHEMALE TOP LOOKING FOR BOTTOMS, VERSATILE WITH 8 INCHESSHEMALE TOP LOOKING FOR BOTTOMS, VERSATILE WITH 8 INCHES Shemale Top for Bottom in Chicago Hello Gentlemen!!!  I'm the girl your momma warned you about.  I am Ginger, mixed race, age 28. I am a stunning temptress w/ lovely personality very friendly confident & discreet... Have your very best experience with me.. TOP & BOTTOM!! Don...
  • Let Cherry Make Your Fantasies Come True Tonight!...Let Cherry Make Your Fantasies Come True Tonight!... Hello I'm Cherry a hot trans escort in Chicago. Thanks for checking out my ad. First of all here is a little more about myself. Im a horny sexy Latina trans girl with a very charming polite lovely personality yet kinky and fun to play with. I'm always trying to make you have a great experience and s...
  • 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 Chicago boos out there. I'm an independent trans escort serving the Chicago area. 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 sexy, hung and fun. You c...
  • Your Trans Fantasy Starts Here – Let’s Cam First 💦Your Trans Fantasy Starts Here – Let’s Cam First 💦  Looking for a sexy, open-minded transgender woman in Chicago? That’s me! I  love connecting on cam—it’s the perfect way to get to know each other before possibly meeting up.  She/Her, sensual, spontaneous, and ready to play. Click the link, view my  profile, an...
  • July 11th, 2025
  • Welcome to the Land of Neons and Nylons Baby!Welcome to the Land of Neons and Nylons Baby! Big City Kitty here to share the glamour that is Chicago with a sexy man tonight. You can take me anywhere, I'm a fully passable t-girl, functional and always in the mood for some hot sexy fun. Incall, outcall, travel, events, parties or anything you have in mind. I like it flashy and trashy! If you...
  • Free Illinois Transexuals GuideFree Illinois Transexuals Guide Illinois Transexuals Guide The Illinois 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 Illinois Transexuals Guide online.  Where to Meet Transexuals in Illi...
  • Chicago🍆Ebony🍆CrossdressChicago🍆Ebony🍆Crossdress EBONY/BLACK CROSSDRESSER WITH NICE THICK COCK 😉😉 -VIEW MY CHICAGO CROSSDRESSER  I WANT TO DRESS UP SUPER SUPER CUTE FORYOU AND MAKE YOUR FANTASIES COME TRUE.THEN I WANT US TO EXPLORE OUR WILDEST AND NAUGHTIEST FANTASIES - WHAT ARE YOURBIGGEST TURN ONs AND F...
  • Illinois Transgender Nightclubs and BarsIllinois Transgender Nightclubs and Bars Illinois Transgender Clubs Directory Browse the Illinois Transgender Clubs Directory online from our webmasters at TGGuide.com. The development team at TGGuide has hand-curated the most complete listing of transgender nightclubs and bars you will find anywhere. Browse the worldwide listings or refi...
  • VIDEO✅VERIFY🍆Big Transgender Cock💦VIDEO✅VERIFY🍆Big Transgender Cock💦 PARTY TRANSSEXUAL GIRL 🎱☘️🎉💨IM VISITING & VERIFIED 💥 SEXY SHEMALE IN Chicago lOOKING FOR SOMEACTION AND PLAY TONIGHT.. are you down? I have a sexy body and an amazing cock for you. 5 STAR⭐️ EXPERIENCE  * NDA’s ACCEPTED  / A+LIST  clients 💫...
  • II'll be your sexy superhero tonight baby!... Yeah baby it's super tranny to the rescue in Chicago. Freaky as hell and I always rise while others fall. If you need a sexual superhero tonight then I'm your girl. I got 9 inches uncut that wants you to have your way. Oral, hand, anal or? Anything you want this ebony trans escort is good with. Goin...
  • EXOTIC LOVELY BEAUTY TRANSEXUAL - HOT SEXY TSEXOTIC LOVELY BEAUTY TRANSEXUAL - HOT SEXY TS Want to Meet a Pre-Op TS in Chicago? I'm fully functional transexual, top or bottom. Kink and fetish friendly. Chat about anything with me. I am a sexy and extremely wild Shemale who will not say 'no' to anything. I have a lot of offer!  SEE MY PICS & CONTACT INFO: @TSMonica27 If you lik...
  • Chicago Transsexual Body Rubs 💋 Kiss & Slide SessionChicago Transsexual Body Rubs 💋 Kiss & Slide Session  Do you crave closeness? I’m the TS goddess who gives more than just a massage—I  give connection, fantasy, and deep release. I will touch you with warm oil and soft skin while  my body is pressed against yours from chest to chest with our mouths together and our hips and...
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  • 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...
  • Asian Trans-Escort into Cosplay at Your Service Tonight!...Asian Trans-Escort into Cosplay at Your Service Tonight!... Need a versatile Japanese trans-escort for dress-up events or a good time in Chicago? I have an extensive collection of costumes for most any occasion. Anything from period, erotic, to sci-fi, to BDSM, to fantasy, to super hero and beyond. I can be what ever you desire. Click here for more. Search f...
  • OnebitchinOnebitchin' Babe in Chicago Im a Funloving Person... You must live in the Chicago area I am a Trans escort and will sex you up hard because I'm ALL the woman you need tonight baby! Tell me how you want it, you must be honest 100% No Bullsh#t. No games. No cops, no minors or lowballers PLEASE!! Sex isn't mandatory but, you must please be clean, respect...
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  • Trans Beauty Craving Connection – Let’s Get Intimate on Cam 🔥Trans Beauty Craving Connection – Let’s Get Intimate on Cam 🔥  Hey you 😘 I’m a transsexual woman who’s sweet, sexy, and ready to  build something exciting — whether it’s playful chatting, hot cam sessions, or something more meaningful. View My Profile and Message Me — I’m  waiting. I  identify as She/...
  • Vietnamese Trans Escort Serving the Chicago Area...Vietnamese Trans Escort Serving the Chicago Area... kawaiiTranX is back on demand in Chicago for all loyal admirers. I a fully passible and functional trans female escort who can take care of you like no body else can. I make you wonder how you ever got along without kawaiiTranX before. Incall, outcall OK, no women, underage or police! Come see ...
  • Black BambiBlack Bambi's Got a BIG Love Gun and it's Loaded Baby! Chicago Trans Escort Black Bambi I shoot to thrill! Hey boys your gonna get more bang for your buck with BlackBambi in Chicago! Don't go off half-cocked with those other trans escorts out there and be left wanting for more. I'm smokin' hot top or bottom incall, outcall, parties, events, discreet, p...
  • SO PASSABLE YOU CAN TAKE ME HOME TO MOM AND DAD😇SO PASSABLE YOU CAN TAKE ME HOME TO MOM AND DAD😇 Shemale Escort in Chicago Elegant and alluring I will bring your desires to life 💖🔥💫    Are you searching for an alluring Shemale Goddess to hookup with in Chicago? That's right!! I'm a sexy escort and I'm here to please you DADDY.  You've come to the place as I'm read...
  • Hung Black Shemale Top or Bottom for Chicago Gentleman 🌟Hung Black Shemale Top or Bottom for Chicago Gentleman 🌟 Hung Black Shemale for Chicago Gentleman Hi there! My name is Lady Velvet. I am the perfect package to explore all your hidden shemale fantasies.✨🍭 I guarantee you’ll come back running for more! 💋 I am a real shemale with a full, thick 100% operational🍆 , can service you top or bot...
  • Come Play with BRITx – a TS Beauty in Chicago 💃Come Play with BRITx – a TS Beauty in Chicago 💃 BackRoom with BRITX – TS Beauty in Chicago 💃 My Stripper Pix - Profile✅  Hello there! I'm Laryssa. I enjoy embracing fun and excitement in life while cherishing the moments of joy and fulfillment with others, around me too. Tonight you can find me at the club having a time dancing ...
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  • Hot Natural Tgirl in ChicagoHot Natural Tgirl in Chicago Hot Natural TGirl Companion I'm a 33 y.o shemale/trans girl looking to provide a great time for a fun, good man. I am versatile, very sensual and full of fun. I like to kiss as well...;) Feel free to inquire on further details. 420 friendly You will like what you see. Clean and safe play Visit me...
  • Hey Chicago - IHey Chicago - I'm Nastina With the BIG Weena!... Chicago Trans Escort 4 Hire Nastina here a fully passable in social situations, fully functional in bed and packin' a BIG surprise for ya! I'm the best trans escort in the Chicago area so don't even mess with the rest big boy. Discreet, top or bottom, incall, outcall, events ok, women ok. No h...
  • 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...
  • TRANNY PORNSTAR, ELITE, Fun & Freaky down to earth transsexual. Im 100% Real (Guaranteed)TRANNY PORNSTAR, ELITE, Fun & Freaky down to earth transsexual. Im 100% Real (Guaranteed) Tranny Pornstar in Chicago   A Very ELITE, Fun & Freaky down to earth transsexual. Im 100% Real (Guaranteed) & I've been seen all over the NET. Im completely versatile Top or Bottom, Aggressive or Submissive! I have beautiful natural 36D breasts.   I am a ts woman of many inter...
  • S Beauty for Cam, Chemistry & Midnight Conversations 🌙📱S Beauty for Cam, Chemistry & Midnight Conversations 🌙📱  Hey handsome 😘 You will find me attractive because I am a trans woman who combines sweetness with  sensuality and playful nature. During my transition I use She/Her pronouns because I seek authentic  connections between two people. View My Profile and Message  Me – I&rs...
  • ON STAGE TONIGHT!!  Shemale Laryssa 💋 Chicago ON STAGE TONIGHT!! Shemale Laryssa 💋 Chicago Sexy Shemale Laryssa Ready to Fulfill Your Wildest Fantasies 💋 Hey there, handsome! I'll be at the club tonight.. I will treat you extra special in the back room, if you know what I mean 💦👄 Are you looking for a sexy shemale in Chicago  who knows how to have a good time? Look no furth...
  • New Trans Ladyboy in Town...New Trans Ladyboy in Town... Hi I'm Leslie your trans escort new here in Chicago. They say the men here in Chicagoland love a ladyboy who can freak it at night. That's good because I'm a superfreak baby! Always horny and ready for action. Incalls and outcalls okay. I also do events, parties, functions and more. Can travel if ne...