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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November 9th, 2025
💋 TGirl Treat, So Sweet & Discreet 💦 Hey babe… I’m the trans fantasy you’ve been dreaming about and now I’m right here, ready to play 😘 I’m soft in all the right places, with a secret surprise that’ll leave you breathless. I love to tease, please, and take you somewhere you’ve never been b...
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 ...
Naughty 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...
Hey 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...
JACKIE🍩BBW SHEMALE EXPERIENCE SOME EXTRA LOVINGCHICAGO, ILLINOIS - BBW TGIRL😉 Hey Guy’s I’m JACKIE I am an sexy Plus Size TGirlwho will make you cum tonight in Chicago, Il, bbw❤️ ❤Anal Sex...Blow Job🍩🍆❤Body to Body Nuru Massage❤Shower and Bathe together❤Kissing Cuddling & tou...
PRE-OP HOTTIE READY TO PARTY AND PLAY! Pre-Op Trans Hottie for Local Hookup Chicago PreOp Hottie. My name is Angela but you can call me Angie. I am pre-op, versatile, AVAILABLE NOW MESSAGE ME WHEN YOU ARE READY TO MEET PARTY FRIENDLY, NUDE SHOWER, KINKS!!SUGAR DADDY, GFE, LET ME SPOIL YOU!!! xoxo Live Chat and Contact @Angie...
Imma Spread Your Sexy Ass & Eat It Like Grandma's Stuffing 🍘👩‍🍳💅 Username: @Transbbydll1- Location: Chicago- Dating Profile: Yes- Trans Dating Pics: 29TEXT ME DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Trans Dating Pics & Socials I'm a fully functional pre-op trans woman looking for a strong bull who wants to have some fun. I give the best head in th...
Chicago TRANNY, needs❤️🍆 I'm a Transgender lady living in Chicago or somewhere near by... I'm Born male, however I always known I am a pretty girl. I love meeting guys for sex and having fun. View My Trans Chicago Dating Profile!!💋 Sex in Chicago TONIGHT!!  HOT Transgender Lady Wanting 💋 Want TransSex? Tr...
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...
BLACK Trans Super Fetish - Give Me That Hot Cock Right Off The Grill! 💯🥰🍆💦😛 BLACK Trans Super Fetish Freak in Chicago That black girl magic is SO real though! You KNOW that's right! I got all the right things in all the right places to give you everything you've ever wanted all in the same night. So let's get comfy with some drinks and then take this shit to my satin sheet...
Onebitchin' 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...
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...
The One, The Only, The Sexy Sheila Freakin' it Chicago Style Hi fellas, I'm sexy trans escort Sheila freakin' it Chicago style. I'm fully functional and extra large for all you extra naughty boys out there. Blonde, blue eyes, big package, 35 years old, horny and always ready for some hot action. I'm passible and flexible time wise. Dreams really do come true ...
make 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...
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🐐🍆💦 PROFESSIONAL THROAT GOAT Come Here Baby, Mama Needs Her Protein Shake 😉 Username: @TransFantasies4U- Location: Chicago- Dating Profile: Yes- Trans Dating Pics: 13TEXT ME DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Trans Dating Pics & Socials When I tell you that I'm looking for someone who can fulfill my desires like I can fulfil theirs, I mean full on THROA...
Chicago🍆Ebony🍆Crossdress EBONY/BLACK CROSSDRESSER WITH NICE THICK COCK 😉😉 -VIEW MY CHICAGO CROSSDRESSER  I WANT TO DRESS UP SUPER SUPER CUTE FOR YOU AND MAKE YOUR FANTASIES COME TRUE. THEN I WANT US TO EXPLORE OUR WILDEST AND NAUGHTIEST FANTASIES - WHAT ARE YOUR&nbsp...
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...
VIDEO✅VERIFY🍆Big Transgender Cock💦 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  clients - im a VERIFIED ✅ pornStar⭐️ I lov...
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...
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...
Gloria Chicago trans escort has a secret in her panties!! 🍭 Gloria, Trans Escort in Chicago 💋 NO BLOCKED NUMBERS - Please message me @GloriaTransXual. I'm Gloria and I have a big secret hiding in my panties. I'm completely passable so you can take me out to a business dinner or a fancy restaurant. Only you and I will know the secret that awaits you ...
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...
Trashy Tranny Trisha... Trashy Chicago Trans Escort Hey I'm Trisha here in Chicago, and one man's trash is another man's treasure! Sure I'm nasty, I'm dirty minded, I'm horny AF and a little wild but that's a win-win for the both of us baby! I'm 5'8, medium build with a big hard uncut package, 160 pounds, top or bottom an...
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...
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EMAIL🍆SHEMALE💦ESCORTS I'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 and get naughty, you want some of this Shemale cock! SHEMALE HOOKUPS in Chicago ...
Strict Shemale Dominatrix in Chicago - @DesireeTransDomme Powerful African-Queen Dominatrix in Chicago I am full-time professional Domme Desiree. My Chicago area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you will learn to...
Hot Shemale Paula Ready to Fulfill Your Wildest Fantasies 💦ESCORT 🍆Chicago 👅 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 with local Trans right in your area! ❤️&zwj;🔥Browse Chica...
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,...
LET'S MAKE YOUR TRANS ESCORT FANTASY COME TRUE 🍆🍩💦 Chicago 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 know how to please me. MY SEXY TRANSGENDER ESCORT PIX ...
Dr 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 ...
💎 Spoil Me & Let’s Create Something Special Together 😉  📌My Location: Chicago💎 Want I'm Seeking: A generous and discreet Daddy! 🔥 About Me: Hey, I am a stunning, sweet and playful trans beauty who loves  the finer things in life. Now if you are looking for an elegant, charming and affectionate  companion, I would be more tha...
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...
The Trevor Project Saves Trans Lives BonePage Supports The Trevor Project Proudly sponsored by Chicago Lesbian, Gay, Bisexual & Trans Dating Community The Trevor Project Donations, by Megan Morrison BonePage.com is proud to support The Trevor Project, an organization dedicated to suicide prevention efforts among lesbian, gay, bi...
💋🍆 BIG DICK SHEMALE, Chicago💋🍆 Sexy Shemale Joy Looking for Hot Fun in Rockford 🔥🍆💦 Are you ready to explore your wildest fantasies with a sexy shemale in Rockford, Illinois? Look no further, because I'm here to fulfill all your desires. My name is Joy and I am a pre-op trans woman who loves to play and have a good time...
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...
Want to See 👀 BBC Shemale Cock?? 🍆 I'm in the Mood for some super sexy and naughty sex❤️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 🍆🍆 💦 Get in Touch With Me Now and Let's Plan a Hookup I want some naughty sex toni...
Black 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...
November 8th, 2025
Free 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...
HI, SEMALE LOVERS❤️😉 WANT TO PLAY WITH A REAL TGIRL??? View More of My Pix and Profile most amazing pleasure. Chicago ✅COCK SIZE -7.5INCH AND SILICON BOOBS 38 SIZE *SUPER SOFTMy Name is Liza TS,I will give you the  Age: 23 years oldName: Liza TS 💋Gender: Transsexual (Pre-op)Location:ChicagoAvailability: Incall & Outca...
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...
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...
Join Me on a Trans-Tastic Voyage Baby! Upscale Trans Escort in Chicago Hey gents I'm Adriana a trans escort here in Chicago to temp you into going on an adventure, a voyage into my sexual fantasy land. I'm upscale, professional, discreet, functional, fully passible, feminine, fabulous and will seduce you with my sexy flirtacious wa...
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...
I'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...
Tiffany Shelle - Your Chicago Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Chicago It’s Tiffany Shelle your perfect tranny girlfriend 🥰 💕 SAFE💕 💯 LEGIT✨💞 SKILLED, Exotic and Erotic 💦 🥰 I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of! I'm 100% functioning shema...
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 ...
I'm A ✨HOT✨ Trans Sugar Baby - I Need A Sugar Daddy For These Rent Prices 😝👅🍆💦 Are you my Sugar Daddy? I Wanna be your Sugar Baby Here's a little about me:  I'm sweet, cute, and no one will ever be able to tell that I have a sweet surprise waiting, dripping between my legs just for you. We can keep that our little secret.  My voice is feminine and my physique is sm...

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