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

December 7th, 2025

Local Trans Dancers! 🥵🥰 TS Angel with a Devilish Side…😈Come see me at the club tonight!  By looks of things I am an innocent girl but oh baby don’t let that sweet face fool  you I know how to play dirty. I can never get enough of a man who knows how to  have fun and the only thing I enjoy mo...

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...

❤️😍 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...

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...

December 6th, 2025

SHEMALE INTO KINK 🔥 I WILL DOMINATE YOU Sexy Shemale DOMINATRIX Maryjo let's explore our kinks together!😈 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!💦  I want to own you and make you cry out in pleasure and pain. I will do unspeakable things to you and...

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,...

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 ...

Come Play with BRITx – a TS Beauty in Chicago 💃 BackRoom with BRITX – TS Beauty in Chicago 💃 My Stripper Pix - Profile✅  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 ...

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...

I'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  ...

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...

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...

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...

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...

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...

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...

Online 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...

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...

Let's Meet on Cam Then Meet up Chicago📱🎥 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 things😇💫✨ Are you, in search of a transgender woman who can fulfill all your wishes and needs? No need to loo...

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...

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 ...

Trans Goddess Seeking VIP Companion!💎💎Chicago💎💎 Hispanic Tranny Dancing Tonight Spicy, Sultry & Down to Mingle!Hispanic and Spicy Latina TS 👗🔥 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...

NASTY. Put Me 2 The Test I CaNT Lie I' m The Best 9inch vers top TS Top TS HUNG 9 inch in & outs Contact: Chat with me now avail Who’s gonna try all this hard 9 inch WONDER REAL! GFE & VIP. UPSCALE Professional Gentlemen. I’m a High maintenance woman, stylish, smell good, look good, and Fuck great. I Will have U open & begging 4 more! My sw...

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 ...

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...

EMAIL🍆SHEMALE💦ESCORTS SHEMALE HOOKUPS in Chicago 🍆❤️😉  Check My Profile and and Dm MeI'm in the Chicago..  area. I'm willing to travel. As long as you love TRANSSEXUALS and want to have some fun and sexy sex. I want sex now, let's play! View My Pictures We need to have some fun an...

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...

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 ...

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...

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...

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 ...

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...

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...

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...

Trans Temptation Online – Let’s Cam, Laugh & Get Close 😘🎥  Hey you 💋 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 😈View My Profile and Message Me – I’v...

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...

S Beauty for Cam, Chemistry & Midnight Conversations 🌙📱  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...

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...

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...

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...

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...

24 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...

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...

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...

👀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...

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...

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...

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...

Big 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...