Illinois Shemale Dating Classifieds

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  • February 7th, 2026
  • Tranny CockπŸ†ChicagoTranny CockπŸ†Chicago Transgender HOOKUPSin Chicago, Illinois πŸ†β€οΈπŸ˜‰  Check My Profile and and Dm MeI'm in the Chicago, Illinois.. area. I'm willing to travel. As longas you love TGirls and Shemales..I want to have some sexy hookups..I have some fun things in mind. I would loveto connect and see w...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in IllinoisSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Illinois Secret Crossdressing Hookups in Illinois Hey there. I'm Sam (Samantha when dressed up). If you're reading this ad you may be a crossdresser who needs to let your feminine side out to play. Me too! If you're in the closet or married, it's no problem. I live alone, have a nice, home with a private ga...
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  • Hot Shemale in Illinois Ready to Fulfill Your Wildest Fantasies πŸ‘„πŸ’¦πŸ†Hot Shemale in Illinois Ready to Fulfill Your Wildest Fantasies πŸ‘„πŸ’¦πŸ† I'm TS and Looking to Date in Illinois My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Illinois who knows how to have a good time? Look no further, because I'm here to make all your dreams come true. I'm really excited about possibly meeting some like minded people and hav...
  • Spicy 🌢  Latina Shemale in Illinois Ready to Fill You πŸ˜‰πŸ˜‰ Spicy 🌢 Latina Shemale in Illinois Ready to Fill You πŸ˜‰πŸ˜‰ LATINA SHEMALE SEEKING πŸ”₯🌢  Are you looking for a spicy/hot HISPANIC TS.. absolutely KINKY and ready to do anything?? I'm from Illinois.  Don't look any further, because I'm here to make all your wet dreams come true. My name is MARIA TS and I am a pre-op transgender woman who loves ...
  • Chicago Trans Flight Attendant Seeks Man for NSA...Chicago Trans Flight Attendant Seeks Man for NSA... Hi I'm Annie, a 32 yr old t-girl, a Chicago trans flight attendant looking for someone who can understand my wild lifestyle and sometimes erratic hours. I work hard and I play hard. I love men, passion and exploring new things sexually. To say that I'm fetish friendly would be putting it mildly. If ...
  • TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession πŸ˜ˆπŸ‘TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession πŸ˜ˆπŸ‘  Hola, mi amor 😘 The fiery, curvaceous TS Latina body I possess was  made for lust while my soul demands intense passionate nights. Your dream woman has arrived because I possess caramel  skin and thick thighs and long hair and soft lips and a throbbing surprise between my legs th...
  • I’m a Sexy and Naughty T-Girl Here in Illinois.I’m a Sexy and Naughty T-Girl Here in Illinois. Illinois T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Illinois area. Sweet, sexy, friendly and outgoing. I will definitely make you feel happy/sexy vibes and relaxed. I have an amazing body boys. I'm a pretty t-girl with a big present! So forget all your  worries and ...
  • Do you know the difference between a dick and a bucket of popcorn?Do you know the difference between a dick and a bucket of popcorn? You don't know? 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 Illinois tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer tha...
  • Tiffany Shelle - Your Illinois Tranny Girlfriend! πŸ’žTiffany Shelle - Your Illinois Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Illinois It’s Tiffany Shelle your perfect tranny girlfriend πŸ₯° πŸ’• SAFEπŸ’• πŸ’― LEGIT βœ¨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% functioni...
  • πŸ‘‘ Chocolate Queen with Soft Curves & Naughty Desires πŸ”₯πŸ‘‘ Chocolate Queen with Soft Curves & Naughty Desires πŸ”₯  πŸ”₯| Do you feel that you want something new and exciting and that you want to  remember for a long time? I am a hot, all natural ebony TS with all the right amount  of curves and a naughty and adventurous spirit. I don’t just know how to tease, please and  make you want ...
  • She-male looking for hot date to please. She-male looking for hot date to please. Asian Shemale in the Illinois Area Hot Asian shemale wants to date and please you in the art of erotic passion. I'm non op, fully functional, lovely and funny. Please to contact me @CarmelShemaleXXX. My name is Carmel. I'm 33 years old. I like to explore your sexual fantasies! Let's make them come...
  • 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 Illinois boos out there. I'm a sexy trans woman currently living in large and lovin' every second of it. 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 se...
  • Having fun and Staying YoungHaving fun and Staying Young Young trans fem looking for nice date with lady. I am kind and thoughtful and you will have a very good evening if I take you out. Let me know what you want to do or where you want to go. View profile and message me xoxo, Sherry....
  • II'm a Good Girl, But When I'm Bad I'm Great! White trans woman wants NSA with suitable sexy man for erotic encounters in the Chicago area. Good girls don't, but I DO! About me: 5'8 160 pounds, 27 yrs old, red hair, blue eyes, big D, bottom and 36C cups. I am clean, dress up well and disease free. Don't be shy, if you live in Chicago then hit m...
  • Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹  You want flavor? Spice? A woman who can dance for you, then ride you like she  owns you? That’s me, papi 😘 I’m a curvy, high-femme  TS Latina with a pretty face, wild hips, and a very naughty surprise underneath. View My Latina TS Pictures - I love to  tease, fl...
  • I love a confident, seductive TS womanβ€”could you be the one? πŸ’‹I love a confident, seductive TS womanβ€”could you be the one? πŸ’‹  A handsome, intelligent and adventurous man, here looking to meet a gorgeous TS woman to have  excitement, chemistry and wild nights. I just love confident women who know what they want and I’m more  than ready to spoil, explore and indulge in pleasure together.  Handsome,...
  • TS Bombshell Looking for a Man Who Can Keep Up! πŸ’‹ IllinoisTS Bombshell Looking for a Man Who Can Keep Up! πŸ’‹ Illinois  Naughty, Nice and Looking for a Thrill!Transsexual Seeking Man for Sexy Fun! View More of My Pictures πŸ“Έ Are you the sort of man who enjoys  just a touch of danger, a touch of excitement, and a lot of passion? I’m the  trans beauty you’ve been dreaming of — sexy...
  • TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘  Papi… I’ve been thinking about you 😘 View More Sexy TS PIX - My curvy figure and thick TS  Latina body has caramel skin while my filthy mind and mouth were made for you 😈. I become  submissive only when you want me to submit while I transform into a dominant forc...
  • II'm the Girl Mother Never Warned You About!... But then, how could your mother have known? I'm Dirty Diana corrupting good decent honest men like yourself here in Illinois for many moons. I got a big secret and it's show and tell time baby! It's easier to show you than to tell you. I'm fully functional and passible. I need a sexy man who lives n...
  • MALE SEEKING SHEMALE πŸ†Illinois Ready to Play and Fuck πŸ’¦MALE SEEKING SHEMALE πŸ†Illinois Ready to Play and Fuck πŸ’¦ I have a secret.. 🀫 I've always want to see what it's like to play with a shemale!!  Hi I'm John, I'm in Illinois  and I love to be free and have fun.. Are you looking for a man who really knows how to treat you?? I really want to show you what I got sweetie. I have a good heart a...
  • Marina TS πŸ† Visiting and ReadyMarina TS πŸ† Visiting and Ready Visitng Houston, Texas - Your TGirl Escort Hi guys Marina TS visiting your city …. We can start a sexy friendship, but if you are generous, it would not be bad. Please call me and text me when you are ready....MESSAGE ME HERE. Sexy, latina, femenine and beatiful TS woman here. English/e...
  • Superb Shemale in Illinois...Superb Shemale in Illinois... T-Girl for NSA Encounters in Illinois When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Illinois. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle, f#ck an...
  • Sexy Shemale Illinois I know You Want to Play Sexy Shemale Illinois I know You Want to Play FEMININE AND SECURE SHEMALE  Hot and kinky shemale seeking a hot and fun guy who isn't scared of a beautiful and secure Trans Woman.. I'm located in Illinois; I am AlaneTS and  I am here to fulfill all your desires. If you are in the area or planning to be. and  looking for a hot and...
  • Partners in crime, or?Partners in crime, or? Sexy, Slytherin, Aries, ISTP and more, if that gives you a hint about my personality traits. So, I’m a sexy, sensual, tender, animal loving, bookworm. I am a bit of a flirty whore, who loves mystical magical movies and stories, so let’s get that out in the open. If you live in the I...
  • 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. I can be a bit racy and dirty when it's appropriate, but always maintain my poise in public. If you live in the Illinois area and are interested then drop me a line and introduce yourself. You can...
  • πŸ‘‘ TS Ebony Goddess Looking for Her King Tonight πŸ”₯πŸ‘‘ TS Ebony Goddess Looking for Her King Tonight πŸ”₯  πŸ« Juicy, thick, and so addictive! I am a stunning ebony trans  vixen with the perfect hourglass figure, long legs, and a playful personality. I have a  thing for men who know what they want and are not afraid to go after it. Whether you are  a professional or a newbie to the ...
  • Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Illinois Seeking!!Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Illinois Seeking!! Seduction Starts with One Look…Once I have your attention, baby, I don’t let go. 😏 I’m the trans woman you’ve been dreaming about—sexy, confident, and oh-so-willing to turn up the heat. Let’s start slow… a few drinks, a little teasing, some whispers abo...
  • Dr FreakinDr Freakin'furter - Mine's Bigger Than Yours! White T-girl here 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 Illinois area come see if you measure up! Click here for explicit photos. Look ...
  • I Need a STEAM ROLLER Baby!!!I Need a STEAM ROLLER Baby!!! I want you to inject my soul with that sweet lover's pole till there ain't much of me left behind. I'm your whore so just F my brains out tonight. I'm a naughty trans looking for a top big boy to have his way with me. So it's heels and ass up and earth moving sex the hard way. That's the way I like ...
  • Brandi 27 tall slim hot trans chick 8.5 inchBrandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Illinois Beautiful Brandi. If you're attracted to the female form then you will want to message me @ BrandiTS27.  I'm pre-op, tall, slim and beautiful with 8.5 inches for top or bottom. I love oral sex!! Kink friendly, have toys to explore all your naug...
  • Your Shemale Addiction 😈πŸ₯΅ Starts NowYour Shemale Addiction 😈πŸ₯΅ Starts Now Shemale Seeking Male.. Your Fantasy Starts Here 24yr old Transsexual/Shemale in Illinois seeking some fun and campanionship. I would like hookups and I'm also wanting love. I think we should play some plans and see what we can come up with.. I'm open minded and ready!! Take a min to View my Pi...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Illinois My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and other times I let it gr...
  • πŸ’– Discreet, Naughty & Waiting for a Man Who Can Handle MeπŸ’– Discreet, Naughty & Waiting for a Man Who Can Handle Me  πŸ”₯ I’m an exotic ebony TS bombshell in Illinois with a love for steamy nights,  deep connections and uninhibited pleasure, keep it hot and wild and unforgettable! Whether you are looking for  an exciting adventure, a sensual night of passion or just something you’ve nev...
  • Latina TS Firestarter – I Don’t Do β€œMild” πŸ”₯πŸ‘ Latina TS Firestarter – I Don’t Do β€œMild” πŸ”₯πŸ‘  I’m your next obsession, papi 😘 View More Pictures of Mine! TS. Latina. Voluptuous. Insatiable. And craving a man who can handle my curves, my tongue, and my need for deep, sweaty pleasure 😈 You’ll taste my perfume before I even touch you… and feel my body long after I lea...
  • Beautiful Krystale 25 Illinois visiting nowBeautiful Krystale 25 Illinois visiting now Beautiful Shemale Visiting Illinois Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me.  Krystale25shemale Age: 25 Location: Illinois Sex: Shemale Seeking: Man ...
  • INTERACTIVE MAP: Transexual Tracker in the Illinois Area!INTERACTIVE MAP: Transexual Tracker in the Illinois Area! Local Transexual Hookups Meet local transexuals in the Illinois area. View our interactive map below to meet local trans hookup members who are seeking dating or sex hook ups. Click any thumbnail below to begin your search. Interactive Illinois Trans Hookups Map ...
  • Letha Aims to Fill YOU With Her Love Gun!!!Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Illinois and I got a BIG love gun to whip and pound you with until you scream! I'm def top and alpha and don't take no shit! Imma make you suck me first just for foreplay then I'll throw you back for some hard insertion...
  • Hi Guys!! I am looking for someone fun!Hi Guys!! I am looking for someone fun! This is Lara and I am 41 and transitioned when I was 24. I pass exceptionally well and you will be surprised at my hidden skills. Call me! ...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Illinois Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Illinois to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enjoy 24/7 Online Chat ...
  • Local Crossdresser πŸ˜‰πŸ˜‡  LET ME PLAY DRESSUP FOR YOULocal Crossdresser πŸ˜‰πŸ˜‡ LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Illinois View My Personal Pix - 🀫  A sexy Crossdresser from Illinois, here, and her name is  KaralynnCD. I am pre-op but that has not stopped me from enjoying all the benefits that come with being  a Crossdressing Trans woman. If you like dirty games...
  • TS Beautiesβ€”Let’s Have Some REAL Fun! 😏πŸ”₯TS Beautiesβ€”Let’s Have Some REAL Fun! 😏πŸ”₯  I am a tall, fit, and successful man and I have a taste for gorgeous TS women  who love to be adored, desired and pleasured. Whether you are looking for a wild  night, a passionate escape or something ongoing, I know how to treat a woman right. πŸ’‹ Must  have confidence, charm...
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  • Illinois πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Illinois πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Real Latina TS Seeking πŸ”₯Ready to Fulfill Your Wildest Fantasies  My Spicy Latina Shemale Pix! -Are you looking for a sexy shemale to play with? I'm a bit of a drama queen. I love dressing pretty and getting my nails done. I will also dress sexy in lingerie for you. Do you want to have a hoo...
  • Chocolate Mocha Trans Lady Needs That Sweet Vanilla Tonight!...Chocolate Mocha Trans Lady Needs That Sweet Vanilla Tonight!... Hey all my sexy Chicago boos I'm Letta a black trans girl seeking a white male in Chicago for some sexy and passionate one on one action. If you are new to the t-girl scene don't be afraid baby. I'll surely take good care of you and rock you nice and gentle for at least the first 5 minutes! I can't ...
  • Elisabeth waiting to be your QueenElisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Illinois AREA Hi baby! I am waiting to meet you. I can host or travel to you. Down to earth preop transexual woman seeking an understanding man who can appreciate my uniqueness. I am a great cook and great fun! Let your hair down and allow me to pamper you! Private Message...
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  • New Body New MeNew Body New Me M2F post-op in Illinois Hi, I'm Natasha, newly transitioned and ready to date. Gorgeous red head with slender legs and curvy body. Want to come and join me for a drink? I love sex in my new gender!!! Seeking a local area man who will enjoy sex and passion with me. Message me online Natash...
  • I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Illinois )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Illinois ) Sexy Crossdresser Elissa Looking for Hot Fun in IllinoisπŸ’‹    Do you like knowing I'm a man in womens clothes.. do I look sexy??    - VEW MY CD PICTURES Are you wanting to satisfy your innermost desires with a sexy shemale such  as myself? My name is Elissa and I am a ...
  • DonDon't Worry I Bite! Feisty redhead trans in Illinois full of fun and loves it rough on the bottom. I'm 5'9, 170 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 ...