Chicago Transgender Classifieds

Browse Chicago transgender classifieds to meet local transexuals, crossdressers and shemales for sex, dating or friendship. Contact any of these trans advertisers to swap pics and contact info. Chat online or text and arrange real-time sex hookups if you feel a connection. It's free to search all trans classifieds, or post your own adult ad!

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September 7th, 2026
I want to be a whore I am a transexual 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. Click here and come see me anytime!...
Mixed Race Male Seeks Sexy Shemale for FWB in Chicago... Hi there all you hot trans ladies I'm James new to Chicago and I want to meet you. I've been divorced for about a year now. Not really wanting to dive in too deep just yet, but you never know what will happen in the future. I need a sexy more mature woman who can relate to me in terms of life experi...
Chicago BDSM Master Taking on New Trans Slaves... I am single minded strict, controlling discipline oriented Master in the Chicago area seeking a devoted sub/slave to satisfy all of my whims. I will break you in with proper training protocols starting with, corporal punishment, all kinds of Humiliation, hucow, whips, gags, eletro, medical and much ...
September 6th, 2026
Exotic TS Beauty Seeking a Generous Gentleman 🔥💎 Hello lovely, I’m a beautiful trans girl with lots of curves. I’m a confident woman with a beautiful personality. Here I want to meet with the more successful men. Men who can understand that the beauty is also of the feminine kind. Intelligent men, that can realize that we trans girls a...
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 my wife doesn't approve. I REALLY need to let my fem side out to play! I'm seeking cross dressing...
Cute TS Sugar Baby With a Sweet Personality 🌸💕 Hi I’m a trans girl, looking for a nice and confident guy. I like to look pretty and be the centre of attention, so you would need to be confident and also respect women. I love going out with friends and love to be social and have fun and laugh. I also love to be romantic and to be hugged, ki...
🔥 Sexy Trans Beauty in Chicago – Let’s Play 😘 🔥 I’m a confident, flirty trans woman looking for a naughty, open-minded man who knows how to have a good time. I require someone who lives near me to establish genuine emotional bonds through playful games while they disclose their sexual interests to me 😈. waiting for your message babe!! I...
HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Chicago! LET'S TAKE CARE OF THAT TRANNY FANTASY! "Experience your secret tranny desires in real life!"  Hot shemale Gia wants to hook up with you in Chicago!  No strings - just great times, so join my page free for instant access! Shemale Gia's Chicago Sexbook @ShemaleGia27 Photos: 44 V...
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 Black Shemales | Asian Shemales | Crossdressing Friends...
🔥 TS Yessica – Verified & Ready in Chicago 🔥 TS Yessica shows her confident and playful personality when she meets new people because she shows them her authentic self. 😘 You have discovered your perfect trans escort who will create unforgettable experiences while providing an outstanding encounter. I dedicate my free time to people who gen...
Transgender Goddess for Late-Night Escapes & Filthy Fun 🌙💋  It’s late. You’re restless. And you’re craving something… different 😏 - View My Transsexual Dating Profile - As  your TS fantasy girl I offer sultry and smooth vibes while delivering experiences beyond what your ex could have  imagined. My secret between...
TS Sugar Baby💎 Your Perfect Trans Fantasy – Let’s Make It a Reality 💋  📍 Location: Chicago 💖 Seeking: Fun, Exciting, &  Discreet Connections Some about me.. Trans SugarBaby: Hey there! I belive I'm a stunning, sweet, and playful trans beauty who loves good  vibes, great chemistry, and unforgettable nights.. I'm in my early 20's and I'm...
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. Let's wing it tonight baby! I love men, passion and exploring new things sexually. To say that I'm fetish friendly wou...
I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Chicago I'm queen Delilah a trans woman here in Chicago searching for her king. You'll get the royal treatment when you're with me honey! Just grab hold of my magic scepter and his majesty can have anything he desires. Imagine the intrigue and scandalous position...
New Body New Me M2F in Chicago Hi, I'm Natasha, newly transitioned, exploring this beautiful new chapter in my life, and ready to date. Gorgeous non-op 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...
Hot trans chick with nice boobs Hot trans chick in Chicago. Sheila wants to meet you. Hey guys, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, well endowed and functional, top or bottom. I love oral sex giving, receiving or 69. Want to explore kinks? Me too!! Want to...
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 Chicago tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer than...
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...
Having fun and Staying Young Young-ish 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 @SherryTransFem33 and message me. Send your pics for mine. I'm hoping to find real chemistry an...
Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Chicago Hey! Thanks for looking at my ad. This is the first time I've done this so bear with me plz. I am Jared, FtM trans man. I transitioned at age 25 and I just turned 30. Come and meet me!  Check my personal profile @FtMJared29 and say hi!&nb...
I Need a Sexy Man to Tame Wild Willy! Hung Chicago Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Chicago with a big wild willy that always seems act out in inappropriate ways at the worst times. For instance I'll be relaxed, minding my own business at my favorite Starbucks and see a ...
SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Chicago Secret Crossdressing Hookups in Chicago 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 gar...
Trans Sugar Baby Energy in Chicago - I'm ready for a night out! Hey there… I’m a sweet, confident, and playful trans beauty in my early 20s who loves good vibes, strong chemistry, and nights that turn into stories you replay later 😘 I enjoy being admired, feeling cared for, and bringing a little sparkle wherever I go. Yes, I can be your “ba...
Black T-girl Sub Bottom Wants Her Backdoor Man! Come on over baby! I'm Annie, an intense sexual t-girl living in Chicago who loves it doggy style and any way I can get it. I'm 29 years old, 5'9 in heels, tight as hell, horny as hell and pack a big surprise for my unsuspecting man. Let's spend the night together and make it last. If you need some ...
Flawlessly gorgeous trans bombshell in Chicago Trans MtF for Man in Chicago I transitioned 6 years ago at the age of 18. I'm still fully functional but live 24/7 as a female. I pass flawlessly so let's go out on the town! I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am short and cute and I have bedroom e...
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...
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 ...
September 5th, 2026
Beautiful Krystale 25 Chicago visiting now Beautiful Preop 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.  Krystale25shemale Username: @Krystale25shemale Age: 25 Location: Chicago, Illinois Sex: MtF Trans Seeking: Man ...
The Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project Proudly sponsored by Chicago Lesbian, Gay, Bisexual & Trans Dating Community The Trevor Project Donations, by Megan Morrison BonePage.com proudly supports The Trevor Project, an organization dedicated to suicide prevention among lesbian, gay, bisexual...
I'm the Girl Your Mum 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 Chicago 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 ne...
British T-girl Seeking Classy Gentleman in Chicago... I am Lacy, a white, blonde haired, trans woman, 30 years old, 5'9, 160 pounds, from Manchester, England and need a man who is educated, refined and handsome. I have just relocated to Chicago and am financially independent and looking for a gentleman who is like-minded, equally solvent and has except...
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 ...
Latina TS Dirty Girl Looking for a Gentleman's Dark Side 🔥👠  Sweet on the surface. Filthy underneath. View My Trassexual Dating Profile Here - As a TS darling I present like a dream while  playing like a fantasy. Stockings. Heels. A tight dress. Soft skin. And a  throbbing surprise you’ll love exploring 😘 I need you to undress me gr...
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...
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...
Trans Playmate Sex Kitten... Ebony trans woman in Chicago wants to be your sex kitten and playmate so let's make a playdate! I love all men so any race or body type or political side is fine with me. I can get along with anyone and we're gonna have a great time. I do all men, gay, bisexual, bicurious, swingers and groups. I am ...
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...
T-Girl New to Chicago and lonesome! I Christina and am a trans woman, 33 years old, 5'9, highly skilled and new here in Chicago. I would like to meet a handsome gentleman to go to dinner with. Not only am I lonesome, but I'm horny too so buckle up and hold on tight! After dinner just ride me hard and don't hold back big boy! Message m...
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 and show you what...
Erotic exotic Asian queen in Chicago now (25) Asian Transexual in Chicago Stunning TS - Talia 25. Asian mixed race, non op, loves sex. Nice build with long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information. Classy in public but trashy in the bedroom. Versatile and attentive to your needs. Longte...
🌆 Windy City. Wild Nights. TS Tina is Waiting 💋❄️ Hey sexy… I’m Tina, your thick & tempting TS babe right here in Chicago, and I’m ready to turn up the heat on your cold night 😘 Whether you’re looking for soft touches, deep pleasure, or just a naughty escape — I’ve got you covered. ( View My Sexy Profile ...
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...
Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Chicago who doesn't smoke, but has a thing for sexy men smoking cigarettes. Call it a fetish or a kink if you will, but I love it. If done right it is soo sexy and inviting to my senses and gets my motor running every time. Truth is that it's erotic all in it's...
Hot sexy shemale doll visiting Chicago now Shemale Visiting Chicago Very hot sevy and curvy shemale chick with big delicious lady stick, fully functions for top or bottom. Message me on my profile page @TaylaShemale1. Seeking a kind gentleman for romance and fun. I adore introducing men who are new to shemale sex. HMU! Possible long t...
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 @PennyTSswitch!! I'm a mixed race sweetheart, looking for a nice man who will enjoy being with me. Let's enjoy having some fun, hot dates and ex...
Crystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Chicago area and want to make some new friends! I am a masseuse, hot body, in great shape, and well hung. If you want to get together, Send me a private message Crystal27trans <3  Username: @Crystal27transLocation: Chicago, IllinoisAge: 2...
Glamorous TS Sugar Baby Ready to Be Spoiled 💎💋 Hi handsome… I’m a beautiful trans sugar baby that loves the luxuries in life and I’m searching for a confident man who will treat me like the queen I am. I am very soft and feminine with a playful edge and you will always have a smile on your face when we talk. View My TS Sugar B...
TS Tina – Your Seductive Fantasy in Chicago 🔥 Your dream TS girl Tina has arrived to create a hot experience while she will help you discover your most intense sexual fantasies. I create a perfect combination of wild and warm sensations through my soft touch and my playful nature. I find men who understand how to handle a woman with confidence ...
Hookup With Chicago TS Sugar Baby Now! 💌 Want to Hookup and Find Chicago 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're interested in 😉.. Do you want to meet local shemales who want to fuck and have some sexy fun? I dar...
💎 Confident TS Sugar Baby in Chicago 💎 I enter any space with my confident trans woman presence which immediately makes me the center of attention. I find great happiness when people express their admiration and appreciation for me while they actively provide me with care. I find complete happiness when someone else handles everything be...

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