Chicago Shemale Escorts Classified Ads
Chicago shemale escorts classified ads - meet local shemales for hot sex encounters. You will find independent sugar baby arrangements in our trans escort listings. It's free to search all Shemale Backpage adult classifieds, or post your own ad!
Home / Shemale Sex Services / Shemale Escorts
Show Ads In: Bloomington-Normal | Carbondale | Champaign-Urbana | Chicago | Decatur | Peoria | Quad Cities, IA/IL | Rockford | Springfield, IL
July 12th, 2025
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... 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 ...
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...
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 ...
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...
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 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!... 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! 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...July 11th, 2025
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 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🍆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 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💦 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 💫...
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...
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 you lik...
Want to See 👀 BBC Shemale Cock?? 🍆 You Want Some Black 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 ...
Chicago TRANNY, needs❤️🍆 HOT Transgender Lady WantingSex in Chicago 💋 TONIGHT!!
Chicago - Transgender Messanger
I'm a Transgender lady living in Chicagoor 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 Ch...
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!... 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...
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...
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 5'9, 36DD, 160 lbs and a 9’ff toy that always raises for every occasion.
My long natural hair, smooth silky skin and beauty to die for that will have you asking for more.
I have included my video...
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 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😇 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 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...
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...
TULA TGIRL - TS Escorts Tula sexy top Ts ready for good time I love love sub bottoms and I love tops!
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.. Vie...
Hot 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 - 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... 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 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...
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...
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...
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...
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...
Trans Hookups in Chicago, Illinois -- FREE PROFILE SEARCH -- Meet Local Trans Online! Trans Hookups in Chicago, Illinois
LocalTransHookups.com has teamed with TSDates to provide a free membership with instant access to all Illinois trans dating profiles.
Meeting Chicago transexuals isn’t quite as simple as meeting regular woman. Many transexuals feel uneasy about coming out...
First 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. My measurements are 36D-29-34. I have a 9.5 inch thick, 100% fully...
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...
TATTOOED TRANSSEXUAL 🔥💥 HERE FOR SEX AND FUN!! LOCAL SHEMALE ESCORT LISTINGI reside in {City} and I'm always ready!
I have photos, with feedback from satisfied customers .. I will always satisfy and make you feel like the AMAZING MAN you are!! I also have been verified through P411 ✅💍 and you can also find me on OF, Want to see more pictur...
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...
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...
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 ...
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 ...
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,...
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...
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...
Black 🍆 Crossdresser EBONY/BLACK CROSSDRESSER WITH NICE HUGE, HARD COCK🍭
- VIEW MY CROSSDRESSER 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 NAUGHTIEST FANTASI...
SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now! HOT! SHEMALE HOOKUPS
"The girl with a naughty little secret in her panties!"
SIGNUP FREE: INSTANT ACCESS! Shemale Profiles
Uncensored Photos
Swap Your Pics
Live Web Cams
Private Messages
Sext & Hook Up!
Join free for Instant Access to the Shemale Profiles
Black Sh...