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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  • July 19th, 2025
  • Join Me on a Trans-Tastic Voyage Baby!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...
  • Trashy Tranny Trisha...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...
  • ๐Ÿ’‹๐Ÿ’ BUSTY SHEMALE WITH HUGE BOOBIES ๐Ÿ’‹๐Ÿ’๐Ÿ’‹๐Ÿ’ BUSTY SHEMALE WITH HUGE BOOBIES ๐Ÿ’‹๐Ÿ’ I'm a BIG BOOBIE TGIRL ESCORT in Chicago Call me up for the Best Experience Ever... Give me the chance to make your fantasy a reality Full Clean,420 Friendly โ˜˜โ˜˜๐Ÿ’Š๐Ÿ’Š๐Ÿ’‰ WE CAN BOTH SUCK ON EACH OTHER.  ๐Ÿ‘€View My Profile BUSTY SHEMALE  - ๐Ÿ†SUCK MINE๐Ÿ†  FULLY FUNCTIONAL ...
  • Want to See ๐Ÿ‘€ BBC Shemale Cock?? ๐Ÿ†Want to See ๐Ÿ‘€ BBC 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 and Let's Plan a Hookup I want some naughty sex toni...
  • 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...
  • 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...
  • Join Me on a Trans-Tastic Voyage in Chicago Baby!Join Me on a Trans-Tastic Voyage in Chicago Baby! Upscale Trans Escort in Chicago Area Hey gents I'm Adriana a trans escort here in Chicago Area to tempt 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 flirtaci...
  • Looking for THE hottest drag queen in Chicago?Looking for THE hottest drag queen in Chicago? Drag Queen Escort Ready to go to the real drag races sexy? Of course you are! Why else would you be scopin' out my Chicago trans escort listing? I'll take you to the races tonight and we'll run a few laps and get you to the finishing line for the BIG WIN BABY!!! The checkered flags are up and ...
  • ๐Ÿ’‹๐Ÿ† BIG DICK SHEMALE, Chicago๐Ÿ’‹๐Ÿ†๐Ÿ’‹๐Ÿ† BIG DICK SHEMALE, Chicago๐Ÿ’‹๐Ÿ† Sexy Shemale Joy Looking for Hot Fun in Rockford ๐Ÿ”ฅ๐Ÿ†๐Ÿ’ฆ 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...
  • EMAIL๐Ÿ†SHEMALE๐Ÿ’ฆESCORTSEMAIL๐Ÿ†SHEMALE๐Ÿ’ฆESCORTS 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 ...
  • I HAVE NICE TITTIES AND A NICE BIG COCK Chicago!๐Ÿ’ƒ๐Ÿ”ฅ๐Ÿ‘ I HAVE NICE TITTIES AND A NICE BIG COCK Chicago!๐Ÿ’ƒ๐Ÿ”ฅ๐Ÿ‘  Are you looking for a sexy shemale to fulfill all your wildest fantasies? Look no further, because I am here to make all your dreams come true. My name is Selena and I am a pre-op transgender woman who loves to play and have a good time with men who know how to treat me right. ๐Ÿ’‹๐Ÿ”ฅSee my pics &a...
  • ๐Ÿ’‹ TGirl Treat, So Sweet & Discreet ๐Ÿ’ฆ๐Ÿ’‹ TGirl Treat, So Sweet & Discreet ๐Ÿ’ฆ Hey babe… I’m the trans fantasy you’ve been dreaming about and now I’m right here, ready to play ๐Ÿ˜˜ 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...
  • July 18th, 2025
  • 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...
  • NASTY. Put Me 2 The Test I CaNT Lie INASTY. Put Me 2 The Test I CaNT Lie I'm The Best HUNG vers top TS Top TS HUNG in & out Contact: Chat with me @HungTransGrrlXXX Available. Who’s gonna try all this hung, functional, WONDER REAL! GFE, Sugar Daddy, VIP. UPSCALE Professional Gentlemen. I’m a High maintenance woman, stylish, smell good, look good, and Fuck great. I Will have U open &a...
  • II'm A โœจHOTโœจ Trans Sugar Baby - I Need A Sugar Daddy For These Rent Prices ๐Ÿ˜๐Ÿ‘…๐Ÿ†๐Ÿ’ฆ 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...
  • 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...
  • 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...
  • 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...
  • 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...
  • Shemale Escort๐ŸŽ€ ๐Ÿญ IShemale Escort๐ŸŽ€ ๐Ÿญ I'll BE A GOOD GIRL๐Ÿ˜‰..just for you ๐ŸŒทCUM PLAY BABE. i will please๐Ÿ’ฆ I do what I'm told. ๐Ÿ˜ i'm local ๐Ÿ˜ˆNO LAW ๐Ÿ˜ˆNO SCAMS ๐Ÿ˜ˆCONTACT ME WHEN UR READY ๐Ÿ˜ Check out my pictures and my profile  - NOW ...Waiting to please you now daddy. Want to have some fun and get naughty with a real SHEMALE/TGIRL tonight? N...
  • 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 ...
  • PRE-OP HOTTIE READY TO PARTY AND PLAY!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...
  • BLACK Trans Super Fetish - Give Me That Hot Cock Right Off The Grill! ๐Ÿ’ฏ๐Ÿฅฐ๐Ÿ†๐Ÿ’ฆ๐Ÿ˜›BLACK Trans Super Fetish - Give Me That Hot Cock Right Off The Grill! ๐Ÿ’ฏ๐Ÿฅฐ๐Ÿ†๐Ÿ’ฆ๐Ÿ˜› 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...
  • 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...
  • JACKIE๐ŸฉBBW SHEMALEJACKIE๐ŸฉBBW SHEMALE EXPERIENCE SOME EXTRA LOVINGCHICAGO, ILLINOIS - BBW TGIRL๐Ÿ˜‰ Hey Guy’s I’m JACKIE I am an sexy Plus Size TGirlwho will make you cum tonight in Chicago, Il, bbwโค๏ธ โคAnal Sex...Blow Job๐Ÿฉ๐Ÿ†โคBody to Body Nuru MassageโคShower and Bathe togetherโคKissing Cuddling & tou...
  • ๐Ÿ’‹๐Ÿ† always available! what you see is what you get in person! ๐Ÿ’ฆSHEMALE ESCORT๐Ÿ‘…๐Ÿ’‹๐Ÿ† always available! what you see is what you get in person! ๐Ÿ’ฆSHEMALE ESCORT๐Ÿ‘… About Me: โœ”๏ธ9” off hormones โœ”๏ธ100% real and recents pictures โœ”๏ธFIRST TIMER ARE WELCOME! โœ”๏ธfitness body โœ”๏ธFantasy's - fetish's. ๐ŸŒŸ๐ŸŒŸVISITING ๐ŸŒŸ๐ŸŒŸ -INCALL REGULAR SESSION -FULL SERVICE VIP GFE -INCALL๐ŸŒŸ TS MISSY 100% REAL โœ… FaceTime verify ๐Ÿ˜‰ Latina 24 year ol...
  • 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 ...
  • Gloria Chicago trans escort has a secret in her panties!! ๐ŸญGloria Chicago trans escort has a secret in her panties!! ๐Ÿญ Gloria, Trans Escort in Chicago ๐Ÿ’‹ 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 ...
  • Road Head Sally DrivinRoad Head Sally Drivin' Hard in Chicago Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Chicago. What's the best time for road head? When there's gas in the tank baby! Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or park at s...
  • 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...
  • 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...
  • Sexy Shemale in Chicago ๐Ÿ‘…๐Ÿ† Ready to Fulfill Your Wildest Fantasies Sexy Shemale in Chicago ๐Ÿ‘…๐Ÿ† Ready to Fulfill Your Wildest Fantasies 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 and reach mind-blowing orgasms together. โœ… Se...
  • 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...
  • WhoWho's Your Tranny!!! Damn right I am! I know how to treat a man and please him, and I also know what I bring to the game. I give more than I recieve so don't be shy and message me if you live in the Chicago area. I do incall, outcall, travel and all events. I'm passible, fully functional, and in the sheets I'm wild as t...
  • Young, Sexy, Funny, friendly and exotic ๐Ÿ’‹๐Ÿ’‹๐Ÿ’‹ โœ…LATINA SHEMALE ESCORTโœ…Young, Sexy, Funny, friendly and exotic ๐Ÿ’‹๐Ÿ’‹๐Ÿ’‹ โœ…LATINA SHEMALE ESCORTโœ… ๐Ÿ’–๐Ÿ’–๐Ÿ’– SEXY SHEMALE COCK!!๐Ÿ’–๐Ÿ’–๐Ÿ’– ๐Ÿ’–๐Ÿ’– You choose Who you Like๐Ÿ’–๐Ÿ’– ๐Ÿ’–๐Ÿ’– 4 Hands Available ๐Ÿ’–๐Ÿ’– ๐Ÿ’–๐Ÿ’– VIEW MY PROFILE AND PIX๐Ÿ’–๐Ÿ’– ๐ŸŒถ๏ธ MANY CHOICES FOR YOU ๐ŸŒถ๏ธ โœ… Sexy Shemale โœ… Adorable TS โœ… Handsome and Beautiful  FRIENDLY PROFESSIONAL T...
  • 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 ...
  • 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...
  • July 17th, 2025
  • 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,...
  • First timer, or simply curious, youFirst timer, or simply curious, you'll feel completely comfortable with me. I'm very discrete I am 25 year old fully-functional TS girl.  Let's get the physical stuff out the way first - I'm completely passable transexual (and then some). I have an amazingly sensuous model's body - toned and smooth, educated and classy. I am curvy in all the right spots, a lusciously large and fully fu...
  • Kinky, Confident, and in Charge ๐Ÿ†โค๏ธ Your TS Fantasy Come to LifeKinky, Confident, and in Charge ๐Ÿ†โค๏ธ Your TS Fantasy Come to Life I'm a very Dominant and secure Shemale/Transsexual... I'm a bit kinky passionate discreet fun loving hot tranny wants to have some fun today so if you're looking for a hottie let this tranny have some fun with you and fulfill your fantasies I'm Ashley Merree call or text me..  View My Tran...
  • 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...
  • Hot Shemale Paula Ready to Fulfill Your Wildest Fantasies ๐Ÿ’ฆESCORT ๐Ÿ†Chicago ๐Ÿ‘…Hot Shemale Paula Ready to Fulfill Your Wildest Fantasies ๐Ÿ’ฆESCORT ๐Ÿ†Chicago ๐Ÿ‘… 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! โค๏ธ‍๐Ÿ”ฅBrowse Chica...
  • Chicago๐Ÿ†Ebony๐Ÿ†CrossdressChicago๐Ÿ†Ebony๐Ÿ†Crossdress EBONY/BLACK CROSSDRESSER WITH NICE THICK COCK ๐Ÿ˜‰๐Ÿ˜‰ -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 ...
  • Hung Black Shemale Top or Bottom for Chicago Gentleman ๐ŸŒŸHung Black Shemale Top or Bottom for Chicago Gentleman ๐ŸŒŸ 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.โœจ๐Ÿญ I guarantee you’ll come back running for more! ๐Ÿ’‹ I am a real shemale with a full, thick 100% operational๐Ÿ† , can service you top or bot...
  • Chicago TRANNY, needsโค๏ธ๐Ÿ†Chicago TRANNY, needsโค๏ธ๐Ÿ† 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!!๐Ÿ’‹ Sex in Chicago TONIGHT!!  HOT Transgender Lady Wanting ๐Ÿ’‹ Want TransSex? Tr...
  • ๐Ÿ๐Ÿ†๐Ÿ’ฆ PROFESSIONAL THROAT GOAT Come Here Baby, Mama Needs Her Protein Shake ๐Ÿ˜‰๐Ÿ๐Ÿ†๐Ÿ’ฆ PROFESSIONAL THROAT GOAT Come Here Baby, Mama Needs Her Protein Shake ๐Ÿ˜‰ 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...
  • 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.  ...
  • Black Shemale With HUGE COCK FOR YOU๐Ÿ† Black Shemale With HUGE COCK FOR YOU๐Ÿ† I WANT TO DRESS UP SUPER CUTE AND SEXY THEN I WANT US TO EXPLORE OUR WILDEST AND NAUGHTIEST FANTASIES - WHAT ARE YOUR BIGGEST TURN ONs AND FANTASIES?? ๐Ÿ˜ˆ๐Ÿ˜ˆ MESSAGE ME HERE AND LET'S PLAN SOMETHING. EBONY/BLACK SHEMALE WITH NICE HUGE, HARD COCK ๐Ÿญ VIEW MY EBONY TRANSSEXUAL PROFILE ...
  • Hot Shemale Maren in Chicago Ready to Fulfill Your Wildest Fantasies ๐Ÿ’‹๐Ÿ†๐Ÿ’ฆHot Shemale Maren in Chicago Ready to Fulfill Your Wildest Fantasies ๐Ÿ’‹๐Ÿ†๐Ÿ’ฆ 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. ๐Ÿ’ƒ๐Ÿป๐Ÿ”ฅ See my pics & contact info WANT TO...
  • 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...