Chicago, Illinois Shemale Sex Service Providers

Chicago, Illinois shemale sex service providers. Find local crossdressers, transexuals and shemale sex providers including shemale escorts, body rubs, strippers, dom & fetish and more. Select your location below to find shemale sex providers near you. It's free to search or post your own ad!

Home / Shemale Sex Services /

Show Ads In: Bloomington-Normal | Carbondale | Champaign-Urbana | Chicago | Decatur | Peoria | Quad Cities, IA/IL | Rockford | Springfield, IL

  • April 12th, 2025
  • 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...
  • Online Cam Fun? Then Maybe Hookup? ๐Ÿ‘„๐Ÿ’ปOnline Cam Fun? Then Maybe Hookup? ๐Ÿ‘„๐Ÿ’ป  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. ๐Ÿ”ฅ She/Her, and all about making fantasies come  true. Let’s get wi...
  • TULA TGIRL - TS EscortsTULA 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...
  • 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...
  • 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...
  • Trans Goddess Seeking VIP Companion!๐Ÿ’Ž๐Ÿ’ŽChicago๐Ÿ’Ž๐Ÿ’Ž Hispanic Tranny Dancing TonightTrans Goddess Seeking VIP Companion!๐Ÿ’Ž๐Ÿ’ŽChicago๐Ÿ’Ž๐Ÿ’Ž Hispanic Tranny Dancing Tonight Spicy, Sultry & Down to Mingle!Hispanic and Spicy Latina TS ๐Ÿ‘—๐Ÿ”ฅ I don’t just dance, I seduce. ๐Ÿ˜ If you love an exotic, trans beauty who knows how to tease, I’m waiting at the club and I'm bored.. Ughh, please come save me and let's have some fun. I want to take a few shots w...
  • 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...
  • 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...
  • Chicago Transsexual ๐Ÿ’ฆ Wet Goddess ExperienceChicago Transsexual ๐Ÿ’ฆ Wet Goddess Experience  My name? Doesn’t matter. You will never forget what I do to you ๐Ÿ˜˜ 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...
  • 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...
  • 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...
  • 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...
  • TS ( TRANS ) ๐Ÿ’ฆ Nuru Dreams Come TrueTS ( TRANS ) ๐Ÿ’ฆ Nuru Dreams Come True  Slide into something slippery, baby ๐Ÿ˜ 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...
  • Available NOW ๐ŸŸข Naughty Trans Girl in ChicagoAvailable NOW ๐ŸŸข 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? ๐Ÿ˜˜ 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...
  • Welcome to the Land of Neons and Nylons Baby!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...
  • ON STAGE TONIGHT!!  Shemale Laryssa ๐Ÿ’‹ Chicago ON STAGE TONIGHT!! Shemale Laryssa ๐Ÿ’‹ Chicago Sexy Shemale Laryssa Ready to Fulfill Your Wildest Fantasies ๐Ÿ’‹ 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 ๐Ÿ’ฆ๐Ÿ‘„ Are you looking for a sexy shemale in Chicago  who knows how to have a good time? Look no furth...
  • โค๏ธIโค๏ธI'm Ts Love Bunny๐Ÿ‡Chicagoโค๏ธ Your SHEMALE MASSAGE THERAPIST DO YOU WANT A LOCAL SHEMALEMASSAGE/ NURU THERAPIST? ๐Ÿ’ฆ๐Ÿ’ฆ   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 ...
  • Trans Temptation Online โ€“ Letโ€™s Cam, Laugh & Get Close ๐Ÿ˜˜๐ŸŽฅTrans Temptation Online โ€“ Letโ€™s Cam, Laugh & Get Close ๐Ÿ˜˜๐ŸŽฅ  Hey you ๐Ÿ’‹ As a TS beauty I have a flirty personality and playful thinking.  I’m transitioning, using She/Her pronouns, and I love making genuine connections that start with laughs  and lead to long, late-night cam sessions ๐Ÿ˜ˆView My Profile and Message Me – I’v...
  • Trans Beauty Craving Connection โ€“ Letโ€™s Get Intimate on Cam ๐Ÿ”ฅTrans Beauty Craving Connection โ€“ Letโ€™s Get Intimate on Cam ๐Ÿ”ฅ  Hey you ๐Ÿ˜˜ 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...
  • Black BambiBlack 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...
  • SHEMALE INTO KINK ๐Ÿ”ฅ I WILL DOMINATE YOUSHEMALE INTO KINK ๐Ÿ”ฅ I WILL DOMINATE YOU Sexy Shemale DOMINATRIX Maryjo let's explore our kinks together!๐Ÿ˜ˆ My Name in Maryjo and I'm located in Chicago.. I'm a very Kinky and horny shemale to play with your body and mind!๐Ÿ’ฆ  I want to own you and make you cry out in pleasure and pain. I will do unspeakable things to you and...
  • TATTOOED TRANSSEXUAL ๐Ÿ”ฅ๐Ÿ’ฅ HERE FOR SEX AND FUN!!TATTOOED TRANSSEXUAL ๐Ÿ”ฅ๐Ÿ’ฅ 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 โœ…๐Ÿ’ and you can also find me on OF, Want to see more pictur...
  • Want to See ๐Ÿ‘€ BBC Shemale Cock?? ๐Ÿ†Want to See ๐Ÿ‘€ BBC Shemale Cock?? ๐Ÿ† You Want Some Black 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 ...
  • 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...
  • 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...
  • 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 ...
  • 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...
  • Tiffany Shelle - Your Chicago Tranny Girlfriend! ๐Ÿ’žTiffany Shelle - Your Chicago Tranny Girlfriend! ๐Ÿ’ž Tranny Escort - Top/Bottom/GFE in Chicago It’s Tiffany Shelle your perfect tranny girlfriend ๐Ÿฅฐ ๐Ÿ’• SAFE๐Ÿ’• ๐Ÿ’ฏ LEGITโœจ๐Ÿ’ž SKILLED, Exotic and Erotic ๐Ÿ’ฆ ๐Ÿฅฐ I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of! I'm 100% functioning shema...
  • Online Now ๐ŸŸข Ready to Play and Possibly Meet IRLOnline Now ๐ŸŸข 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...
  • ๐Ÿ–ค Touch Me, Tease Me, Take Me Chicago Shemale Rubs๐Ÿ–ค Touch Me, Tease Me, Take Me Chicago Shemale Rubs  Are you aching for real connection? Come touch me. Our bodies will merge as I position  myself above you to share my fantasies while our skin dissolves into each other. View My Profile and Pictures - I’m a TS  goddess who loves kissing, sucking, licking, teasing, and intense ...
  • 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...
  • SO PASSABLE YOU CAN TAKE ME HOME TO MOM AND DAD๐Ÿ˜‡SO PASSABLE YOU CAN TAKE ME HOME TO MOM AND DAD๐Ÿ˜‡ Shemale Escort in Chicago Elegant and alluring I will bring your desires to life ๐Ÿ’–๐Ÿ”ฅ๐Ÿ’ซ    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...
  • Chicago TRANNY, needsโค๏ธ๐Ÿ†Chicago TRANNY, needsโค๏ธ๐Ÿ† HOT Transgender Lady WantingSex in Chicago ๐Ÿ’‹ 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...
  • Cam-2-Cam Fun w/ a Trans Vixen in Chicago ๐Ÿ’•Cam-2-Cam Fun w/ a Trans Vixen in Chicago ๐Ÿ’•  I am online and ready to chat, flirt, and maybe even meet someone who knows how to  treat a trans goddess. ๐Ÿ˜‡ 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 ...
  • Letโ€™s Get Wild Online First โ€“ Trans Beauty in Chicago ๐Ÿ‘ Letโ€™s Get Wild Online First โ€“ Trans Beauty in Chicago ๐Ÿ‘   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...
  • The One, The Only, The Sexy Sheila FreakinThe 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 ...
  • 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...
  • 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...
  • VIDEOโœ…VERIFY๐Ÿ†Big Transgender Cock๐Ÿ’ฆVIDEOโœ…VERIFY๐Ÿ†Big Transgender Cock๐Ÿ’ฆ PARTY TRANSSEXUAL GIRL ๐ŸŽฑโ˜˜๏ธ๐ŸŽ‰๐Ÿ’จIM VISITING & VERIFIED ๐Ÿ’ฅ 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 STARโญ๏ธ EXPERIENCE  * NDA’s ACCEPTED  / A+LIST  clients ๐Ÿ’ซ...
  • i want you to come get a dance from me ;)i want you to come get a dance from me ;) Exotic Shemale SheelaWaiting for You Tonight ๐Ÿ’ฆ Looking forward to seeing you tonight! ๐Ÿ’ง  Hey there handsome. Would you like to enjoy an fun dance, from a transgender stripper tonight at the club in Chicago! I'm looking forward to seeing you and having a sexy time together... Perhaps you...
  • Chicago Come See a Local Ebony Tranny Dance on The PholeChicago Come See a Local Ebony Tranny Dance on The Phole  Ebony TS Goddess Seeks a VIP Date! ๐Ÿ’ต๐Ÿ’ฐ๐Ÿ’Ž  Hey boys, I'm an Ebony Transsexual in Chicago and I'm dancing tonight. Come hang out.. Let's have a few shows and maybe a dance. If you say you found me from this ad, I'll give you a SPECIAL DANCE!!! ๐Ÿ‘ธ๐Ÿ’ฆ You like curves, confiden...
  • 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...
  • Come Play with BRITx โ€“ a TS Beauty in Chicago ๐Ÿ’ƒCome Play with BRITx โ€“ a TS Beauty in Chicago ๐Ÿ’ƒ BackRoom with BRITX – TS Beauty in Chicago ๐Ÿ’ƒ My Stripper Pix - Profileโœ…  Hello there! I'm Laryssa. I enjoy embracing fun and excitement in life while cherishing the moments of joy and fulfillment with others, around me too. Tonight you can find me at the club having a time dancing ...
  • Horny Trans Cutie Online in Chicago โ€“ Letโ€™s Chat First ๐ŸŸขHorny Trans Cutie Online in Chicago โ€“ Letโ€™s Chat First ๐ŸŸข  Looking to meet someone real? I am a flirty, wild trans girl who is ready to  chat and see where things go. I get off on naughty cam convos and love to tease before  we take it further. Let’s heat things up and maybe plan a hot little meetup. Message  me, view my profile, ...
  • Cam Now, Hookup Later? Trans Girl in Chicago ๐Ÿ–คCam Now, Hookup Later? Trans Girl in Chicago ๐Ÿ–ค  Let’s have some real fun. I’m a naughty trans girl who’s up for cam play  and possibly more. Let’s chat, get each other going, and see if we vibe enough to  meet. I’m flirty, freaky, and love being watched. Hit me up, view  my page, and let’s ...
  • 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...
  • 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...
  • 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 ...
  • Sexy and TS Hottie Ready to Tease You! ๐Ÿ˜˜โœจ Join me in the clubSexy and TS Hottie Ready to Tease You! ๐Ÿ˜˜โœจ Join me in the club Sassy Shemale Stripper in Chicagocome get a dance babe!! ๐Ÿ”ฅโค๏ธ  I’m tall, tan, and totally tempting… ๐Ÿ˜ 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...