Chicago, Illinois Shemale Sex Service Providers

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  • April 11th, 2025
  • BLACK SHEMALE💋CHICAGOBLACK SHEMALE💋CHICAGO 💎CHICAGO, ILEbony Shemale💎ESCORT SEXY AND HOOKUPS NOW 👀MY EBONY CHICAGO ESCORT PIX Beautiful face & Perfect Ebony Body★ I Offer bareback❤😋 Anal Sex...BDSM🍑🍆 Body to Body Nuru Let's get out and have some fun, meet up fora drink maybe? My favorite bar is The Closeton&nbs...
  • 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...
  • ❤️I❤️I'm Ts Love Bunny🐇Chicago❤️ Your SHEMALE MASSAGE THERAPIST DO YOU WANT A LOCAL SHEMALEMASSAGE/ NURU THERAPIST? 💦💦   Hey babe, I'm here in Chicago and I'm a college student. I'm really good with my hands and body so I'm doing this MASSAGE stuff as a way to make money on the side. Honestly I love it so much, I think I will always want to do this ...
  • SHEMALE TOP LOOKING FOR BOTTOMS, VERSATILE WITH 8 INCHESSHEMALE 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...
  • Trans Beauty Craving Connection – Let’s Get Intimate on Cam 🔥Trans Beauty Craving Connection – Let’s Get Intimate on Cam 🔥  Hey you 😘 I’m a transsexual woman who’s sweet, sexy, and ready to  build something exciting — whether it’s playful chatting, hot cam sessions, or something more meaningful. View My Profile and Message Me — I’m  waiting. I  identify as She/...
  • OnebitchinOnebitchin' 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...
  • JACKIE🍩BBW SHEMALEJACKIE🍩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...
  • 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...
  • 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...
  • 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...
  • 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...
  • II'm online now – Ebony Shemale Cams in Chicago 👠  The sensual trans girl within me enjoys performing wild cam sessions which deliver unfiltered authentic content. Through  the screen I enjoy teasing and flirting with others while creating an intimate space for us to experience every moment  together 😘💋 View My Online Cam  ...
  • 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...
  • ChicagoChicago'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...
  • 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...
  • Flirty, Dirty & Ready to Party! 👗🔥 Meet Me at the ClubFlirty, Dirty & Ready to Party! 👗🔥 Meet Me at the Club Chicago TS DANCER AT THE CLUB!!  ✅ By looks of things I am an innocent girl but oh baby don’t let that sweet face fool   you – there is no way I am innocent. There is nothing much I can’t do when  it comes to  playing the game. It is only a man who can have s...
  • 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...
  • Seductive Roselia is excited to make your wildest dreams 💦 true ChicagoSeductive Roselia is excited to make your wildest dreams 💦 true Chicago SHEMALE BODY RUBS AND MASSAGE Located in Chicago - Stop on in! 👄😻    Looking for a Sexy and Sensual Massage from a TS/Shemale, in Chicago? Well search more! I'm Roselia ( SHE/HER ). I'm here to make sure you have a time with me ✨  As a transgender woman I love what I do...
  • Independent Shemale Escort Top or Bottom in ChicagoIndependent 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...
  • 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...
  • 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...
  • 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...
  • 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...
  • 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...
  • TATTOOED TRANSSEXUAL 🔥💥 HERE FOR SEX AND FUN!!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...
  • TS Temptress Online – Let’s Flirt, Cam & Maybe Fall in Lust 😈💋TS Temptress Online – Let’s Flirt, Cam & Maybe Fall in Lust 😈💋  As a sensual trans woman I seek someone to connect with through flirting to discover potential deep connections.  My pronouns are She/Her and I am currently in the process of transitioning while fully embracing all  the changes my body experiences  💋 Check out My Profile then...
  • April 10th, 2025
  • Black 🍆 CrossdresserBlack 🍆 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...
  • Your TS Dream Girl Is One Click Away – Sweet Talk & Dirty Fun 💦Your TS Dream Girl Is One Click Away – Sweet Talk & Dirty Fun 💦  Are you seeking a casual relationship with an attractive trans woman who might become your long-term partner?  You’ve just found her 😘 I embrace my transformation into a woman by using She/Her  pronouns while I live my life as a transsexual beauty who is currently in the pr...
  • Big Tits - Big Ass - Big CockBig Tits - Big Ass - Big Cock EBONY SHEMALE🍆DIVA🍆BBC let me please you and let's cum I'm a EBONY 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 ☘☘💊💊💉👀View My Profile FULLY FUNCTIONAL and guaranteed...
  • Hung Black Shemale Top or Bottom for Chicago Gentleman 🌟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...
  • Shemale Body Rubs - 👅 Body Worship MassageShemale Body Rubs - 👅 Body Worship Massage  Come to me, sweet thing. I provide full body-to-body trans massage which creates a boundary  between pleasure and passion. My smooth and glowing skin will glide across your entire body while I speak dirty  words into your ear. View My Profile and Pix - I will use my breasts to mass...
  • 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...
  • 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...
  • 👀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...
  • 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...
  • Hot TS Girl Ready to Talk, Tease & Take Things Further 💋📲Hot TS Girl Ready to Talk, Tease & Take Things Further 💋📲  You should consider me as your new obsession 😘 I am a transitioning transsexual woman who brings  both warmth and wit and a wild personality to meet others especially when we connect through flirty messages and  hot webcam sessions. View My Profile and Message Me — let&rsquo...
  • 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 ...
  • 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...
  • Chicago 🥵 Erotic Heat Therapy With a Sexy ShemaleChicago 🥵 Erotic Heat Therapy With a Sexy Shemale  Lay back, baby. I will ride on top of you to relieve your most tense areas  😏 I am a sensual TS masseuse who possesses magical hands and a body that knows how to  move. View My Sexy Profile - Each session provides absolute body contact pleasure during which I remain naked with o...
  • 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 ...
  • Chicago Transsexual 💦 Wet Goddess ExperienceChicago Transsexual 💦 Wet Goddess Experience  My name? Doesn’t matter. You will never forget what I do to you 😘 View My Profile and Message Me -  I provide sensual and erotic massage services where bodies intertwine and time stands still. The nuru slides I  provide cover your entire body while being sensual and soake...
  • 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...
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  • 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...
  • 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...
  • Chicago TRANNY, needs❤️🍆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...
  • 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...
  • Cam-2-Cam Fun w/ a Trans Vixen in Chicago 💕Cam-2-Cam Fun w/ a Trans Vixen in Chicago 💕  I am online and ready to chat, flirt, and maybe even meet someone who knows how to  treat a trans goddess. 😇 I am She/Her, currently transitioning, and love naughty cam  sessions. Want to see where this could go? I’m good for a hookup if the vibe is  right. Come say hi ...
  • 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...