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  • October 18th, 2025
  • Your Trans Fantasy Starts Here – Let’s Cam First 💦Your Trans Fantasy Starts Here – Let’s Cam First 💦  Looking for a sexy, open-minded transgender woman in Chicago? That’s me! I  love connecting on cam—it’s the perfect way to get to know each other before possibly meeting up.  She/Her, sensual, spontaneous, and ready to play. Click the link, view my  profile, an...
  • 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...
  • 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 ts woman of many inter...
  • 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. 420 friendly You will like what you see. Clean and safe play Visit me...
  • 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...
  • 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,...
  • 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...
  • TS Girl Seeking Vibes, Cam Fun & Maybe Something Real 💖📲TS Girl Seeking Vibes, Cam Fun & Maybe Something Real 💖📲  Do you find attractive confident curvy trans girls who display a naughty smile and soft voice? You  already have my full attention 😘 The process of transitioning brings me great joy as I experience all  its wonderful aspects. She/Her stands as my preferred pronouns while I seek g...
  • HI, SEMALE LOVERS❤️😉HI, SEMALE LOVERS❤️😉 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 & O...
  • 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...
  • 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...
  • 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 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...
  • 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...
  • ON STAGE TONIGHT!!  Shemale Laryssa 💋 Chicago ON STAGE TONIGHT!! Shemale Laryssa 💋 Chicago Sexy Shemale Laryssa Ready to Fulfill Your Wildest Fantasies 💋 Hey there, handsome! I'll be at the club tonight.. I will treat you extra special in the back room, if you know what I mean 💦👄 Are you looking for a sexy shemale in Chicago  who knows how to have a good time? Look no furth...
  • 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...
  • TS ( TRANS ) 💦 Nuru Dreams Come TrueTS ( TRANS ) 💦 Nuru Dreams Come True  Slide into something slippery, baby 😏 I’m a sensual trans goddess offering nuru massage that feels  like heaven and ends in ecstasy. My body will move across yours in a sensual gliding motion without  any friction as we connect skin to skin and heart to heart. View My Profil...
  • 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...
  • 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...
  • Vietnamese Trans Escort Serving the Chicago Area...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 ...
  • ❤️😍 TS Tease Ready to Please—Meet Me Tonight!😍❤️ ❤️😍 TS Tease Ready to Please—Meet Me Tonight!😍❤️  Sassy & Classy in ChicagoCome Play with Me!  😍  Hey there sexy! 💋 I am your favorite trans bombshell dancing your fantasies of your  dreams. Get a private show for free at the club here in Chicago, I’ll be there turning up the  heat. Of course, drinks and l...
  • 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...
  • 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. My measurements are 36D-29-34. I have a 9.5 inch thick, 100% fully...
  • EBONY🍆TS - incall and outcall💦EBONY🍆TS - incall and outcall💦 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...
  • 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...
  • 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 5’8 tall 139 lbs, pre-op, versatile, AVAILABLE NOW MESSAGE ME WHEN YOU ARE READY TO MEET 420, PARTY FRIENDLY, GFE, NUDE SHOWER, KINKS!! xoxo Live Chat and Contact @AngiePre...
  • 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...
  • SO PASSABLE YOU CAN TAKE ME HOME TO MOM AND DAD😇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...
  • Sexy and TS Hottie Ready to Tease You! 😘✨ Join me in the clubSexy and TS Hottie Ready to Tease You! 😘✨ Join me in the club Sassy Shemale Stripper in Chicagocome get a dance babe!! 🔥❤️  I’m tall, tan, and totally tempting… 😍 I’m into giving you a show  and leaving you spellbound by the things I do. My curves are deadly, my smile is  contagious, and my lap dances?! You won&rsqu...
  • 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...
  • October 17th, 2025
  • 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...
  • Tiffany Shelle - Your Chicago Tranny Girlfriend! 💞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...
  • Your TS Cam Crush is Ready to Connect – Come Play 💦💋Your TS Cam Crush is Ready to Connect – Come Play 💦💋  Seeking a smart trans girl who can turn you on with her smile and voice? Look no  further 😘 I’m a TS woman with soft curves, a curious heart, and a dirty  little secret. I use She/Her pronouns and I love sharing raw, real moments on cam  — the kind that make your...
  • Gloria Chicago trans escort has a secret in her panties!! 🍭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 ...
  • Upscale Asian Trans Escort New in Chicago...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...
  • 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 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...
  • 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...
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  • Let’s Get Wild Online First – Trans Beauty in Chicago 👠Let’s Get Wild Online First – Trans Beauty in Chicago 👠  As a trans girl I have a passion for cam sessions which I describe as naughty, raw and  real. I am located in Chicago and I am open to meetups if the vibe  is hot. I identify as She/Her, enjoy exploring and I am willing to try anything that  feels good. I want to flirt, tease an...
  • 👀Transgender Escort Looking👀👀Transgender Escort Looking👀 Straight BOY'S or Gay discreet, and First timer Curious Guy Are All Welcome here💋Any Fantasy on your mind will surely make it into Reality. No any Judgement❤️ And Can Guaranteed..MY SEXY TRANSGENDER ESCORT PIX 📸💦COUPLES💦ACTIVE💦 PASSIVE💦BLOW JOB 💦KISSES Check o...
  • She/Her TS Babe Wants Late Night Chats & Real Chemistry 😘She/Her TS Babe Wants Late Night Chats & Real Chemistry 😘  Do you want to experience genuine conversation together with a trans woman who understands how to maintain playful and  exciting relationships? 😘💋 Check out My Profile then Send Me a Message because I want to  ignite this connection. As a transsexual girl I possess both a larg...
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  • Online Now 🟢 Ready to Play and Possibly Meet IRLOnline Now 🟢 Ready to Play and Possibly Meet IRL  A transsexual woman from Chicago seeks someone to chat and flirt with potentially leading to  relationship formation. Your search for a passionate trans encounter ends here. I am currently transitioning and use  She/Her pronouns while enjoying hot moments especially when I am on came...
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  • Chicago - 🔥 TS Temptation TouchChicago - 🔥 TS Temptation Touch  You will find me different from other body rub babes because I am the trans temptation which has been  on your mind. My expert hands and full lips and soft curves will provide you body massage experiences you  never had before. view my sexy trans profile here - The nuru gel serves ...
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  • Online Cam Fun? Then Maybe Hookup? 👄💻Online Cam Fun? Then Maybe Hookup? 👄💻  I am a trans woman living in Chicago and I am open-minded and always ready  to explore. What do you want to know about me? Let’s chat first—cam to  cam—and see if there is a connection. 🔥 She/Her, and all about making fantasies come  true. Let’s get wi...
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  • 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...
  • Available NOW 🟢 Naughty Trans Girl in ChicagoAvailable NOW 🟢 Naughty Trans Girl in Chicago  I am here and ready for some cam to cam fun. Looking to get naughty with a transitioning  She/Her babe who knows how to please? 😘 Let’s chat and let our imaginations  run wild… maybe we’ll end up meeting for some real fun. Check my link and profile to  conn...