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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January 25th, 2026
Road 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...
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...
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...
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...
Who'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...
💋🍆 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...
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...
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...
Kinky, Confident, and in Charge 🍆❤️ 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...
TS ESCORT in Chicago..😏 Curious? Let me be your first. 😏 If you are looking for a  TS who is a passionate, seductive high class companion then look no further. I am offering you a combination of  elegance, charm and pure excitement that will leave you wanting more.Straight BOY'S or Gay discreet, and First timer Curious Guy Are All Welcome here�...
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...
Shemale Escort🎀 🍭 I'll BE A GOOD GIRL😉..just for you 🌷CUM PLAY BABE. i will please💦 I do what I'm told. 😏 i'm local 😈NO LAW 😈NO SCAMS 😈CONTACT ME WHEN UR READY 😏 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...
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 ...
Young, Sexy, Funny, friendly and exotic 💋💋💋 ✅ SHEMALE ESCORT✅ 💖💖💖 SEXY SHEMALE COCK!!💖💖💖 💖💖 You choose Who you Like💖💖 💖💖 4 Hands Available 💖💖 💖💖 VIEW MY PROFILE AND PIX💖💖 🌶️ MANY CHOICES FOR YOU 🌶️ ✅ Sexy Shemale ✅ Adorable TS ✅ Handsome and Beautiful  FRIENDLY PROFESSIONAL T...
January 24th, 2026
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...
GRAB A DRINK OR GRAB MY COCK?? 🍆🍩💦 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 ...
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...
Independent 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...
Illinois 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...
Chicago'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...
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 ...
💋👅🍆LG PRETTY TS - I'M YOURS DADDY💋👅🍆 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 can provide. Don't be shy about sharing your wildest fantasies with me – I am always op...
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...
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...
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...
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...
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...
💋 TGirl Treat, So Sweet & Discreet 💦 TS 4 M 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...
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...
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 ...
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...
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 DOM🔥 You Were Made to Serve 😈 Now Let’s Make It Official My name is Shelly and I'm Trans.. You will love me like the QUEEN I am! I hope you're into melting away into immense fantasy. I will own your mind forever after we're done!! I'm into feminization ( You'll Be My SISSY BOY ) 🎀 Orgasm Denial, you wait till I tell you to cum💦Worship & fac...
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...
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 ...
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 😍 Yessica TS Escort 🍆 Use me 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 dont call playing with me Text or Message Here.. I'm the...
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...
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...
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...
January 23rd, 2026
💎 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...
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...
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...
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...
all 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...
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 ...
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...
🐐🍆💦 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...
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 ...
EXOTIC 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...

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