Chicago Transgender Escorts Sex Classifieds

Browse Chicago transgender escorts listings for sex provider listings of TS escorts and trans sugar baby arrangements near you. Due to U.S. regulations, prostitution ads are illegal and thus are not allowed. All ads in BonePage trans escort ads are for legal escort services or adult companionship arrangements. Any sex that may occur is strictly by mutual consent between adults, and of their own free will.

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  • March 4th, 2025
  • 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...
  • Trans Hookups in Chicago, Illinois -- FREE PROFILE SEARCH -- Meet Local Trans Online!Trans Hookups in Chicago, Illinois -- FREE PROFILE SEARCH -- Meet Local Trans Online! Trans Hookups in Chicago, Illinois BonePage has a trans hookups partnership to provide a free membership with instant access to all Illinois trans sex profiles. Meeting Chicago transexuals isn’t quite as simple as meeting regular woman. Many transexuals feel uneasy about coming out pu...
  • You Spin Me Right Round!You Spin Me Right Round! Like a record baby, right round, round round! I'm Olivia a trans escort in Chicago and you look like your lots of fun. I want some! Common honey don't be shy just jump my bones and do me hard and fill me. I'm a petite spinner tgirl dirty as it gets, and up for anything you might have in mind. I...
  • all the chocolate youall the chocolate you'll ever need!! 🍆💦 Well Hung Shemale!!! BLACK SHEMALE FOR SEXY FUN - YOUR ESCORT View my Escort Profile & Pix You'll love my big cock and nice sexy boobies.. Brown beauty looking to play with the perfect generous Gentlemen! 🌹🌹 Slim, petite treat with Pretty with nice big boobies and cock💦 Get your cock ready to cum 😘 loc...
  • 💋🍆 always available! what you see is what you get in person! 💦SHEMALE ESCORT👅💋🍆 always available! what you see is what you get in person! 💦SHEMALE ESCORT👅 The Best Transsexual Escort♥️  MISSY TGIRL - YOUR NEW FAVORITE SHEMALE ESCORT!About Me: ✔️9” off hormones ✔️100% real and recents pictures ✔️FIRST TIMER ARE WELCOME! ✔️fitness body ✔️Fantasy's - fetish's. 🌟🌟VISITING 🌟🌟 -INCALL REGULAR SESSION -F...
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  • SHEMALE TOP LOOKING FOR BOTTOMS, VERSATILE, FUNCTIONALSHEMALE TOP LOOKING FOR BOTTOMS, VERSATILE, FUNCTIONAL 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...
  • SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now!SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now! HOT!  SHEMALE HOOKUPS "The girl with a naughty little secret in her panties!"  Meet shemales looking for no strings hookups, sugar daddy arrangements and potential GFE!  SIGNUP FREE: INSTANT ACCESS! Shemale Profiles Uncensored Photos Swap Your Pics Live Web Cams P...
  • ChicagoChicago's Own Trans Escort FABULOUS FRANCIS - I'm a Born Diva Honey!... T-Girl Escort in Chicago I'm Fabulous Francis a trans escort here in Chicago serving all you sexy guys with my sexy womanly wiles. I'm all the F-words baby! Fabulous, fun, fantastic, functional, friendly, flambouyant and very f#ckable! I do top or bottom and am extra large=well equipped. Let's make...
  • March 3rd, 2025
  • VIDEO✅VERIFY🍆Big Transgender Cock💦VIDEO✅VERIFY🍆Big Transgender Cock💦 PARTY TRANSSEXUALVISITING & VERIFIED  SEXY SHEMALE IN Chicago lOOKING FOR SOME ACTION AND PLAY TONIGHT.. are you down? I have a sexy body and an amazing cock for you. View My Trans Chicago Dating Profile!!💋 5 STAR⭐️ EXPERIENCE  * NDA’s ACCEPTED  / A+LIST  c...
  • 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...
  • T-Girl with a big surprise - Your gonna fucking love every inch of it!T-Girl with a big surprise - Your gonna fucking love every inch of it! Chicago's Fabulous Trans Escort Hi boys I'm Mona a trans escort here in the Chicago area with a special treat. I'm fully functional, passible and extra large (10 thick inches uncut) Top or bottom and very kinky for all you sexy pervs out there who want to get the most out of Mona tonight. Tell me y...
  • 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...
  • 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 trans woman of many interests, I love ...
  • Hot Shemale Paula Ready to Fulfill Your Wildest Fantasies 💦ESCORT 🍆Chicago 👅Hot Shemale Paula Ready to Fulfill Your Wildest Fantasies 💦ESCORT 🍆Chicago 👅 Chicago TGIRL and Want to have some sexy fun tonightWell Hung... 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 connect...
  • EBONY🍆TS - incall and outcall💦❤️❤️ VALENTINES DAY SPECIAL❤️❤️ EBONY🍆TS - incall and outcall💦❤️❤️ VALENTINES DAY SPECIAL❤️❤️ Ebony Shemale With BBC🍭do you like pretty black TS? My Personal Profile - View Here Name: PARIS EBONY TS 🍆 Ethnicity: Black - Ebony Age: 23 years old Height: 5'5"  Weight: 134lbs Location: Local, Willing to travel Op: Pre-Op 🐈 ( Still have my Cock) Services: B...
  • 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...
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  • ❤️I❤️I'm Ts Love Bunny🐇Chicago❤️ Hi, I'm Ts Bunny🐇 - Your Favorite Escort in Chicago I Live in Chicago,I tend to be a bit shy over the phone (so be discrete!) , but very easy to connect with in person :)Real/Verified pics,  Great reviews. P411 Verified ✅ & OF=TsPrincessLoveBunny -My Pics are authentic,...
  • 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...
  • 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...
  • 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...
  • LETLET'S MAKE YOUR TRANS ESCORT FANTASY COME TRUE 🍆🍩💦 Chicago 💋 Shemale Halley in Chicago looking for a hot time 💦 Are you ready to explore your wildest fantasies with a sexy shemale in Chicago? Look no further, because I'm here to fulfill all your desires. My name is Halley and I am a pre-op transgender woman who loves to play and have fun with men who...
  • 💋👅🍆Hot Shemale Renell Ready to Fulfill Your Wildest Fantasies💋👅🍆💋👅🍆Hot Shemale Renell Ready to Fulfill Your Wildest Fantasies💋👅🍆 BUSTY RENELL🍆SHEMALE COCK DO YOU WANT TO EXPERIENCE A SHEMALE ESCORT TONIGHT???😉😉 My tight ass is always ready for some intense pounding, and I love nothing more than feeling your cock deep inside of me. Let's play together and experience the ultimate pleasure that only a shemale like me ...
  • Chicago 😍 Yessica TS Escort 🍆 Use meChicago 😍 Yessica TS Escort 🍆 Use me TS Escort Ready and Available - Do Whatever You Want! TS Yessica ( Real Shemale Escort )  come have some fun 😍 I'm ready for watever ! Throat goat 👅 foreal baby looking to have a good time and please you daddy so if your looking for a good time call me plz be serious when contacting me d...
  • DonDon't Worry I Bite! Feisty redhead trans in Chicago full of fun and loves it rough on the bottom. I'm 5'9, 160 pounds, 32 years old, well endowed, fully functional, passible and hot to trot. You can take me anywhere, but I can't promise to always behave. I have a dirty mind and when the urge hits it's hard to control m...
  • Do you know the difference between a dick and a bucket of popcorn?Do you know the difference between a dick and a bucket of popcorn? Chicago T-Girl Escort You don't know the difference? Well then take me to the movies baby! Mmmm think of all that creamy, buttery, salty goodness! Talk about a double feature. lol Hope you have the munchies for this hot Chicago tranny escort tonight. Save your appetite boy! Me: trans, 30yrs, 5...
  • 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...
  • WANT TO TITTY FUCK ME AND STROKE MY COCK?? 🍆🍩 Chicago WANT TO TITTY FUCK ME AND STROKE MY COCK?? 🍆🍩 Chicago WANT A SHEMALE HOOKUPTONIGHT in Chicago? 💄👅🍆 Check My Profile and and Dm MeAre you looking for a hot and horny shemale to play with? Look no further, because I am here to satisfy all your desires. My name is Glory and I am a pre-op trans woman who loves to have a good time 😈I enjoy all ...
  • Chat, Share & Meet Gorgeous Shemales in Chicago! 🍆❤️Chat, Share & Meet Gorgeous Shemales in Chicago! 🍆❤️ Local SHEMALES and TGIRLSTrade Pix - Message - Meetup Meet Shemales, Transsexuals and TGirls for sex 😍 Hookups and fun tonight!! this app connects you locally with sexy SHEMALES who are online and party to play now ☑️ Check out what this site has to offer and have some fun!&nb...
  • Best big surprise you ever had baby!Best big surprise you ever had baby! Chicago Ebony Tgirl Escort! I am a very sensual and sexual black transexual escort here in Chicago. Love both bottom and top. Comment on and like my pics. I want you to share my pics and share me like you mean it with other men. Gay men, straight men, couples welcome, cis women welcome, curious wel...
  • make you dreams come true with a 1000% real beauty. hot ts kinky nasty just for youmake you dreams come true with a 1000% real beauty. hot ts kinky nasty just for you Hot, Kinky, Nasty TS Beauty! Hey guys. Am 25 years old, hot preop ts. My measurements are curvy, hot and big in all the right places!!! My fully functional toy always rises for every occasion. Sugardaddy arrangement, GFE possibilities.  My long natural hair, smooth silky skin and beauty to di...
  • 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 Illinois 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 neede...
  • 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...
  • 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...
  • Kinky Trans Domme Rules the Night...Kinky Trans Domme Rules the Night... QueenDomme here... Me? I’m the sadistic controlling type, and I certainly don't take any BS. Get down on your wretched knees now and worship me. My domain is Chicago and you exist only to please me. Click here to enter my lair and worship the QueenDomme.     Keywords: BDSM, sex,...
  • EMAIL🍆SHEMALE💦ESCORTSEMAIL🍆SHEMALE💦ESCORTS SHEMALE HOOKUPS in Chicago 🍆❤️😉  Check My Profile and and Dm MeI'm in the Chicago..  area. I'm willing to travel. As long as you love TRANSSEXUALS and want to have some fun and sexy sex. I want sex now, let's play! View My Pictures We need to have some fun an...
  • 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...
  • Black Shemale With HUGE COCK FOR YOU🍆 Black Shemale With HUGE COCK FOR YOU🍆  EBONY/BLACK SHEMALE WITH NICE HUGE, HARD COCK 🍭 - VIEW MY EBONY TRANSSEXUAL PROFILE HERE - ❤️BLACK CROSSDRESSER❤️WILLING TO TRAVEL❤️SEX AND BLOWJOB👅 I WANT TO DRESS UP SUPER CUTE AND SEXY THEN I WANT US TO EXPLORE OUR WILDEST AND NAUGHTIE...
  • 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. Party friendly. You will like what you see. Clean and safe play.  ...
  • JOIN US TO DECRIMINALIZE SEX WORKJOIN US TO DECRIMINALIZE SEX WORK Decriminalize Sex Work Decriminalize Sex Work by Sienna Mitchell, BonePage.com Staff ReporterThis article sponsored by BonePage Chicago Trans Sex Profiles BonePage supports the movement to decriminalize sex work around the world. The unfortunate reality is that transgender sex workers (especially ...
  • 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...
  • HI, SEMALE LOVERS❤️😉 WANT TO PLAY WITH A REAL TGIRL???HI, SEMALE LOVERS❤️😉 WANT TO PLAY WITH A REAL TGIRL??? My Name is Liza TS,I will give you the most amazing pleasure. Chicago ✅ View More of My Pix and ProfileCOCK SIZE -7.5INCH AND SILICON BOOBS 38 SIZE *SUPER SOFTAge: 23 years oldName: Liza TS 💋Gender: Transsexual (Pre-op)Location:ChicagoAvailability: Incall & Ou...
  • Hot Shemale Maren in Chicago Ready to Fulfill Your Wildest Fantasies 💋🍆💦Hot Shemale Maren in Chicago Ready to Fulfill Your Wildest Fantasies 💋🍆💦 WANT TO CUM INSIDE A SHEMALE?💦💋 Are you looking for a sexy shemale to fulfill all your deepest desires? Look no further, because I am here to make all your fantasies come true. My name is Maren and I am a pre-op transgender woman who loves to play with men in every way possible. 💃🏻🔥&...
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Escort in Chicago Hi I'm trans escort Trisha here to show you boys a different kind of kinky love in Chicago. 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. This is for a kinky open minded man sort of man who appreciates w...
  • 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...
  • T-girl Escort Chastity at Your Service Tonight...T-girl Escort Chastity at Your Service Tonight... Fully functional top or bottom trans escort serving up some steamy nights for my fabulous Chicago boos. Don't hate me because I'm beautiful. Come get some of this! Chastity has enough to please any man and your gonna stay satisfied after I'm done with you. I'm also fully passible and can do anything...
  • 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...
  • March 2nd, 2025
  • Sexy Shemale in Chicago 👅🍆 Ready to Fulfill Your Wildest Fantasies Sexy Shemale in Chicago 👅🍆 Ready to Fulfill Your Wildest Fantasies Ready to play with a SHEMALE ESCORT Tonight? I love being both a top and a bottom, so whether you want me to ride you or bend over for you, I'm game. My tight ass is always hungry for a hard cock, and I give the best blowjobs that will leave you begging for more. Let's explore each other's bodies a...
  • You Spin Me Right Round!You Spin Me Right Round! Like a record baby, right round, round round! I'm Olivia a trans escort in Chicago and you look like your lots of fun. I want some! Common honey don't be shy just jump my bones and do me hard and fill me. I'm a petite spinner tgirl dirty as it gets, and up for anything you might have in mind. I...