Chicago, Illinois Shemale Sex Service Providers

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August 29th, 2025

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...

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 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...

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...

Illinois 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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

👀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...

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...

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...

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...

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...

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...

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...

August 28th, 2025

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...

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 ...

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...

Chicago Transsexual Body Rubs 💋 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...

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...

❤️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 ...

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...

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...

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...

Chicago - 🔥 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 ...

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 ...

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...

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...

Chicago 😍 Yessica TS Escort 🍆 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 👅 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...

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...

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...

Chicago 🥵 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...

Flirty, 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...

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...

Let’s Cam, Flirt & Maybe Fall Into Each Other 😈💬  Hi baby 😘 As a trans woman I present myself as sweet and sultry while being open  to the direction of our encounter. My availability includes late-night conversations as well as hot cam interactions and  I will take whatever relationship you seek. View My Profile and  Message...

BLACK 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...

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! 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...

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...

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 ...

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...

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...

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...

Shemale 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...