Chicago, Illinois Shemale Sex Service Providers

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  • July 13th, 2025
  • Chicago Transsexual Body Rubs πŸ’‹ Kiss & Slide SessionChicago Transsexual Body Rubs πŸ’‹ Kiss & Slide Session  Do you crave closeness? I’m the TS goddess who gives more than just a massage—I  give connection, fantasy, and deep release. I will touch you with warm oil and soft skin while  my body is pressed against yours from chest to chest with our mouths together and our hips and...
  • 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!! πŸ”₯❀️  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...
  • INTERACTIVE MAP: Transexual Tracker in the Chicago Area!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 ...
  • Chicago - πŸ”₯ TS Temptation TouchChicago - πŸ”₯ 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 ...
  • 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...
  • Shemale Body Rubs - πŸ‘… Body Worship MassageShemale Body Rubs - πŸ‘… 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...
  • Online Cam Fun? Then Maybe Hookup? πŸ‘„πŸ’»Online Cam Fun? Then Maybe Hookup? πŸ‘„πŸ’»  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. πŸ”₯ She/Her, and all about making fantasies come  true. Let’s get wi...
  • 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 ...
  • Seductive Roselia is excited to make your wildest dreams πŸ’¦ true ChicagoSeductive Roselia is excited to make your wildest dreams πŸ’¦ true Chicago SHEMALE BODY RUBS AND MASSAGE Located in Chicago - Stop on in! πŸ‘„πŸ˜»    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...
  • 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 πŸ’‹ 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 ...
  • 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...
  • Let’s Get Wild Online First – Trans Beauty in Chicago πŸ‘ Let’s Get Wild Online First – Trans Beauty in Chicago πŸ‘   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...
  • 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...
  • Trans Goddess Seeking VIP Companion!πŸ’ŽπŸ’ŽChicagoπŸ’ŽπŸ’Ž Hispanic Tranny Dancing TonightTrans Goddess Seeking VIP Companion!πŸ’ŽπŸ’ŽChicagoπŸ’ŽπŸ’Ž Hispanic Tranny Dancing Tonight Spicy, Sultry & Down to Mingle!Hispanic and Spicy Latina TS πŸ‘—πŸ”₯ I don’t just dance, I seduce. 😏 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...
  • NURU MASSAGE WITH SHEMALE - 🌺 Slow, Wet, & IntimateNURU MASSAGE WITH SHEMALE - 🌺 Slow, Wet, & Intimate  You deserve intimacy. You deserve indulgence. You should lie down so I can explore your entire  body with erotic purpose. View My Profile - My nuru body rubs are wet, slow, and wildly erotic. I  will move my body against yours while sharing dirty dreams through whispers and allowing...
  • 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...
  • 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...
  • II'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...
  • 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...
  • 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...
  • 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...
  • Cam-2-Cam Fun w/ a Trans Vixen in Chicago πŸ’•Cam-2-Cam Fun w/ a Trans Vixen in Chicago πŸ’•  I am online and ready to chat, flirt, and maybe even meet someone who knows how to  treat a trans goddess. πŸ˜‡ 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 ...
  • Trashy Tranny Trisha...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...
  • Chicago 😍 Yessica TS Escort πŸ† Use meChicago 😍 Yessica TS Escort πŸ† Use me TS Escort Ready and Available - Do Whatever You Want! TS Yessica ( Real Shemale Escort )  come have some fun 😍 I'm ready for watever ! Throat goat πŸ‘… 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 d...
  • make you dreams come true with a 1000% real beauty. hot ts kinky nasty just for youmake 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...
  • 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! πŸ’žTiffany Shelle - Your Chicago Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Chicago It’s Tiffany Shelle your perfect tranny girlfriend πŸ₯° πŸ’• SAFEπŸ’• πŸ’― LEGITβœ¨πŸ’ž SKILLED, Exotic and Erotic πŸ’¦ πŸ₯° I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of! I'm 100% functioning shema...
  • Dr FreakinDr 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 ...
  • Your TS Dream Girl Is One Click Away – Sweet Talk & Dirty Fun πŸ’¦Your TS Dream Girl Is One Click Away – Sweet Talk & Dirty Fun πŸ’¦  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...
  • 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...
  • 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...
  • Let’s Talk Naughty First… Then See Where It Goes πŸ˜‰Let’s Talk Naughty First… Then See Where It Goes πŸ˜‰  Hey there! I am a sexy trans girl in Chicago who is all about real  connections with a fun, naughty twist. πŸ’‹ I am totally open to a meet up, but  I love to break the ice over cam first. Let’s explore each other, talk, tease,  and let the chemistry build. She/Her, fully ...
  • 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 ...
  • Your Trans Fantasy Starts Here – Let’s Cam First πŸ’¦Your Trans Fantasy Starts Here – Let’s Cam First πŸ’¦  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...
  • EBONYπŸ†TS - incall and outcallπŸ’¦EBONYπŸ†TS - incall and outcallπŸ’¦ Ebony Shemale With BBC🍭do you like pretty black TS? My Personal Profile - View Here Name: PARIS EBONY TS πŸ† Ethnicity: Black - Ebony Age: 23 years old Height: 5'5"  Weight: 134lbs Location: Local, Willing to travel Op: Pre-Op πŸˆ ( Still have my Cock) Services: B...
  • 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...
  • July 12th, 2025
  • LetLet's Meet on Cam Then Meet up ChicagoπŸ“±πŸŽ₯ Let's Chat ONLINE 🟒  and Then Meet Exciting Transsexual, in Chicago  wanting to get to know each other and then possibly meet up.. See what we can make of thingsπŸ˜‡πŸ’«βœ¨ Are you, in search of a transgender woman who can fulfill all your wishes and needs? No need to loo...
  • TS Girl Seeking Vibes, Cam Fun & Maybe Something Real πŸ’–πŸ“²TS Girl Seeking Vibes, Cam Fun & Maybe Something Real πŸ’–πŸ“²  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...
  • 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...
  • ❀️I❀️I'm Ts Love BunnyπŸ‡Chicago❀️ Your SHEMALE MASSAGE THERAPIST DO YOU WANT A LOCAL SHEMALEMASSAGE/ NURU THERAPIST? πŸ’¦πŸ’¦   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 ...
  • 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...
  • EXOTIC LOVELY BEAUTY TRANSEXUAL - HOT SEXY TSEXOTIC 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...
  • 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...
  • 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...
  • S Beauty for Cam, Chemistry & Midnight Conversations πŸŒ™πŸ“±S Beauty for Cam, Chemistry & Midnight Conversations πŸŒ™πŸ“±  Hey handsome 😘 You will find me attractive because I am a trans woman who combines sweetness with  sensuality and playful nature. During my transition I use She/Her pronouns because I seek authentic  connections between two people. View My Profile and Message  Me – I&rs...
  • 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...
  • ON STAGE TONIGHT!!  Shemale Laryssa πŸ’‹ Chicago ON STAGE TONIGHT!! Shemale Laryssa πŸ’‹ Chicago Sexy Shemale Laryssa Ready to Fulfill Your Wildest Fantasies πŸ’‹ 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 πŸ’¦πŸ‘„ Are you looking for a sexy shemale in Chicago  who knows how to have a good time? Look no furth...
  • A monster in the sheets, but a lady in the streets...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 ...
  • 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! πŸ’΅πŸ’°πŸ’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!!! πŸ‘ΈπŸ’¦ 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...