Chicago, Illinois Shemale Dating Classifieds

Chicago, Illinois shemale dating classifieds. Meet local crossdressers, transexuals and shemales for romance, sex or just make new transgender friends. escorts, body rubs & sex service listings. Select your location below to find shemales near you. It's free to search or post your own ad!

Home / Shemale Dating /

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

May 5th, 2026

TS Beauties—Let’s Make Some Memories 💖✨  I am a dominant, attractive, and confident man looking for a beautiful transgender woman who enjoys being  admired, spoiled, and pleasured.  I am down for mutual attraction, passionate flames and unforgettable  moments. Whether it is a one time or if it is something on going I a...

🍑 Your Secret Ebony Fantasy Is Just One Message Away 😜  👄 I am going to make your wildest dreams come true. I am a classy  yet freaky ebony trans beauty that loves to explore deep desires and steamy fantasies. If you are  a man that appreciates soft skin, full lips and a body made for pleasure then we need to  talk. If you are loo...

Flirty & Feminine CD Ready for Some Fun 💕😈  I’m a sexy, smooth, and playful crossdresser who enjoys the attention, desiring  to be treated like a lady. Seeking for a man who can appreciate a well dressed CD for a  casual fun night or even something ongoing. I am a pleaser and I want to be pleased.  💋 💎 Bath g...

I'm a Horny Shemale 😈💋 Looking For Sex Tonight!! Sexy Shemale💎 Ready to Rock Your World! Local Transsexual - TGIRL Sext App 📲 I'm a Transgender and I'm looking for a naughty man with a nice cock here in near me.. Who is wanting to share some sexy fun with me. I've been really horny and hard!! I love taking cock and giving it, what are...

👠 Classy on the Streets, Naughty in the Sheets – Let’s Play 💋  💖 Just one taste and you’ll be addicted! I am a beautiful, funny TS,  a queen of color with a nice curvy body, beautiful eyes, and a touch that will drive  you crazy. I know what a man needs and how to make him satisfied and craving for more.  I am looking for a confide...

Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Chicago Look no further honey, I'm Franny an Ebony trans woman here in Chicago to fulfill your wildest fantasies. Dreams really do come true when you are with Fabulous Franny. I'm all about the frills and the thrills baby! We can freak it and they don't have to ...

Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Chicago 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 ...

She-male looking for hot date to please. Asian Shemale in the Chicago 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 ...

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 Chicago area and are interested then drop me a line and introduce yourself. You can ...

M-F trans woman wants a date I want someone understanding and kind. Please check out my profile and rate me. I am 36, 5 feet 6 and elegant! My name is Lyssa....

TS Bombshell Looking for a Man Who Can Keep Up! 💋 Chicago  Naughty, Nice and Looking for a Thrill!Transsexual Seeking Man for Sexy Fun! View More of My Pictures 📸 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...

Tainted Love - Beyond Compare! Kinky Trans Woman in Chicago Hi I'm tgirl Trisha 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. I need a hookup with an open minded man. The sort of man who appreciates what ...

MALE SEEKING SHEMALE 🍆Chicago Ready to Play and Fuck 💦 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 Chicago  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 an...

Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 I'm in Chicago and ready to meeup and hookup in LA tonight.. Let's hang out and have some super sexy fun!! I really need to get out and have some fun. Come check out MY PROFILE, browse my pix, videos and send me a message now.. Le...

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 C...

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 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 sex...

Shemale 4 Men 🍆💦 Chicago Ready Now!!  Come Closer, I Don’t Bite, Unless You Do Enjoy It😉   View My Private Pictures -  If you’re looking  to mess around… I don’t know, maybe in a way that’s a bit spicy for the  two of us? I’m a trans beauty with a dirty mind and I love...

Chicago's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Chicago Hi you sexy man! I'm Toni a trans woman from here in Chicago. Looking forward to a fun, sexy evening with you tonight. Let's make some memories that we'll never forget! I'm a 28 year old redhead tgirl who's passionate, warm, funny, hung, functional and loves...

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 ...

Don't Worry I Bite! Feisty redhead trans in Chicago 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 m...

F/M seeking love and fun Female to Male Trans Man in Chicago 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 gro...

Tranny Cock🍆Chicago Transgender HOOKUPSin Chicago, Illinois 🍆❤️😉  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...

Latina TS Firestarter – I Don’t Do “Mild” 🔥👠 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...

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 ...

👑 Chocolate Queen with Soft Curves & Naughty Desires 🔥  🔥| 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 ...

Sexy hung and big busted Hung and Busty Shemale in Chicago Tammy, 39, 38DD, 9" and so cute!! What more could you want in a gurl?!! How about you message me @Tammy38DD and we can talk and meet! Send your recent pic for mine....

TS Beauties—Let’s Have Some REAL Fun! 😏🔥  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. 💋 Must  have confidence, charm...

Email Local Shemales Now! 💌 Want to Hookup and Find Local Shemales? RADE PIX - MESSAGE - BROWSE PROFILES This Website Helps you find local shemales and TGirls meet local men. It's the perfect place to find what you'reinterested in 😉.. Do you want to meet local shemales who want to fuck and have some sex...

BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK 🍆😉 BBC SHEMALE - BLACK TRANS💎 let's play with each others cocks! Hey there boo thang, I know you're going to like what you see. Shiit, I have something for you baby. I love being feminine and sexy. I do still have my penis and I love to use it. I want to see your mouth on it infact.. Would you...

Chicago 😈🍆💦 Latina Shemale is Seeking a Real Man!! Real Latina TS Seeking 🔥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...

I’m a Sexy and Naughty T-Girl Here in Chicago. Chicago T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Chicago 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 st...

TS Latina Goddess – For Men Who Crave Passion, Fire & Pleasure 🔥💋  Hello sweetheart 😘 The TS Latina bombshell body type defines me through my soft lips and thick  thighs and my hidden surprise under red lace. Your pleasure stands as my life purpose because I want to  satisfy your desires and make your body experience intense pleasure through my s...

Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Chicago Area Hi, my fem name is Gloria. I'm a married crossdresser in the Chicago area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but wife doesn't approve. I really need to let my fem side out to play! I'm seeking cross dressing fr...

Beautiful Krystale 25 Chicago visiting now Beautiful Shemale Visiting Chicago 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: Chicago Sex: Shemale Seeking: Man ...

CHICAGO - black🍆crossdresser  EBONY/BLACK CROSSDRESSER  in Chicago Illinois  👅😉🍆  I've been living in Chicago Il, for 2 years now.I love crossdressing and being treated like a lady.I have a nice big cock and I know how to wear sexyclothes really nice for you. I'm thinking about...

Flirty, Dirty, and Ready for Some Fun ❤️ Chicago Shemale Seeking Male Local Shemale Seeks Man For Adventure!  TS Vixen, are you ready to play? Sweet, sultry and a little bit  wild, I am a trans goddess and I do enjoy my men to be as much as a wild  as I am. 😘I don’t want to talk – I want to try something a bit  more exciting. How ab...

Let’s Play a Game—Winner Gets Me 😉 Chicago 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...

TS Latina Snack – Sweet Like Sugar, Dirty Like Tequila 😘🍹  You can find me at the bar where I serve drinks and flirt with customers while enjoying the  atmosphere. I’m your sexy little TS Latina snack — soft lips, juicy thighs, and a tongue that  doesn’t stop until you beg me to 💋 I’ll start off sweet, flirty, &nbs...

Single White Trans Woman Wants FWB in the Windy City.. I'm Hora looking for love in all the wrong places and lovin' every second of it! So here I am single and on this site looking for a sexy man to take me to loveland on a regular basis. (NSA) I expect you to be: not afraid to party, not afraid to go top, not afraid to go bottom, not afraid to take me ...

INTERACTIVE MAP: Transexual Tracker in the Chicago Area! Local Transexual Hookups Meet local transexuals in the Chicago 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 Chicago Trans Hookups Map ...

Local Crossdresser 😉😇 LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Chicago View My Personal Pix - 🤫  A sexy Crossdresser from Chicago, 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 a...

T-Girl Wants No Strings Fun in Chicagoland! Hi I'm Mavin, and verybody says I look like Marlo Thomas an actress from the 1960's and 70's. I'm passible, functional, Ive been described as easy to talk to, comfortable to be around, and sweet in demeanor. I'm a good girl with needs though and want some NSA action in Chicago tonight. You...

Penny for your thoughts? Penny TS in Chicago Hey, I am Penny! I am recently new here and I am non op switch with a pretty nice pair, both top and bottom! Send me a message online!! I'm looking for a nice man who will enjoy being with me. Let's enjoy hot dates and explore sexuality together. If that sounds interesting hit ...

One Night, No Rules, Just Pleasure… Chicago I'm Having a Night to Myself No Strings, just fun.. TS Seeking...🤫  A man who knows what he wants, but also a man who can be tempted, that’s  what I like.  We should begin with eye contact, a slow touch, and perhaps truth or  dare while drinking cocktails. ...

May 4th, 2026

🍫 Dark Chocolate Delight Ready to Melt in Your Arms 😘 💖 Hey, Handsome! I’m a sultry, curvy ebony TS  here in Chicago... I'm Pre Op, ready to play, with a body made for pleasure and a heart full of passion. Discreet, sensual, and looking for a man who knows how to handle me. Let’s make tonight unforgettable! 😘 I'm writing this to ...

Hungry for Explosive Sex, Fun and Adventure?... Yeah, me too honey! I'm Hope, a black trans woman living in Chicago with all the skills to thrill. Vers top or bottom and love hot sex anyway you can get at it. Im curious, smart, free spirited, and funny. I love to travel, eat good food, watch movies and spend intimate time with my man, and no...

Sassy CD Looking for a Real Man 😘🔥  A sweet, sexy and a little naughty crossdresser here, I like to play and  flirt, and I need a strong man who knows what he wants. I enjoy the process of dressing  up, teasing and bringing fantasies to life. If you are into sensual encounters and passionate fun then let me  and y...

TS Latina Bombshell Craving a Real Man to Handle Her 🍑🔥  Hola, papi 😘 You are my TS Latina fantasy because I carry your weight in all  the right places and your softness in all the other places and my body is made for late nights  and louder moans. My skin is golden, my tongue is bilingual, and my hips don’t  lie... especiall...

TS Latina Dream Girl – Ride Me Like a Telenovela 😈📺  Have you ever imagined a sensual Latina woman with large thighs and a narrow waist and a hidden sexual  secret? That’s me, papi 😘 I’m your spicy TS novela — dramatic,  passionate, and unforgettable in the bedroom. Message me here babe - I want your hands on my h...

Your Flirty CD Sweetheart Awaits 💕😘 Chicago I am a  hot, cool and confident crossdresser who enjoys the feeling of being wanted, loved and taken care  of like a lady. Whether you are looking for some hot action, a nice relationship or even a  friend with benefits, I am here to make it unforgettable. 💋 👠 Feminine, fun and ...