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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May 26th, 2026
Dr 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 Chicago area come see if you measure up! Click here for explicit photos. Look f...
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...
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...
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...
Selena Trans girl cute looking for love Hello boys. I am looking for love. You want meet me? I want meet you too! See my pictures @SelenaIsTrans and send me a message to set up a date. I like going out for food or drinks, having a great time and I especially like great sex! I am preop and can do top or bottom though I kind of prefer top ...
Spicy and Hot T-Girl from Colombia Latina T-Girl in Chicago Hey guys, I am Colleen and I am looking for a long term relationship. I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery. Nice surpise waiting for you! Send me a private message! ColleenLatinaT...
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...
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...
!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Chicago Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Chicago 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 M...
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...
Super Barbie T-Girl Wants Hot Men in Chicago... Hey sexy boys, I'm a trans woman looking for a man, forget about my intelligence, talent and great personality, I have something better to spring on you when the time is right. I aim to show you the time of your life and ride the weenie all night! Honestly I'm so horny I could do hand, oral, top or ...
TS Temptress Ready to Ruin You (In the Best Way) 😈💦 Chicago  Hey lover 😘 I’m a high-femme TS bombshell — curves for days, lips  made for kissing (and more), and a hunger that doesn’t quit. After dinner I appear sweet  but I transform into a woman who crawls to the bed naked while wearing only a mischievous  expression...
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...
May 25th, 2026
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...
Cute TS Sugar Baby Seeking Male💎Aria Username: @AriaSweet Trans Friendly: Yes Private Meetups: Yes Phone Chat: Yes Pics Available: 18 Message me if you like feminine Transsexual 💬 Hello, I am AriaTS here in Chicago. A very sweet and very feminine trans-girl that loves to be your sugary little sugar-baby, accompanied by a man t...
Sexy hung and big busted Hung and Busty Shemale in Chicago Tammy, 39, big tits!! Well hung, everything works, clean and so cute!! What more could you want in a gurl?!! How about you message me @Tammy39T and we can talk and meet! Send your recent pic for mine. Username: @Tammy39TLocation: Chicago, IllinoisAge: 39...
Petite TS Doll Looking for a Fun Sugar Daddy 🍬💋 Hi babe... I'm a tiny trans girl, very sexy and feminine. I love to have fun and I'm a very loving girl, I have a lovely sweet smile. I love to be worshiped and pampered by a dominant confident man, who always takes care of his girl, and knows how to please her. HMU HERE BABE!! I am pretty affectio...
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...
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...
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...
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...
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...
Luxury Ebony TS Sugar Baby With Style 👠💎 Hello handsome… I am a ebony trans sugar baby, a beautiful, classy and elegant young lady. I look for confident men that are also very kind to women and who like to spoil a gorgeous lady. Fashion, food and especially great chemistry are my top priorities. let's plan our play date. I love peo...
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...
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 ...
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...
Email Chicago Shemales❤️‍🔥 I'm a well hung TGIRL and Want to have some sexy fun tonight.. Let's Fuck Want to meet the Shemale and Transsexual of your dreams? Look no further, this website gives you instant access to real TGIRLS, SHEMALES and TRANSSEXUALS!! The best part is they are online and you get connected...
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...
Chicago💋 TS Tina – Your Naughty Escape, Anytime, Anywhere 🌎🔥 Hey sexy… Your sweet seductive fully loaded TS dream girl Tina is here to fulfill your deepest desires from anywhere in the world 😘 I possess the right amount of softness while maintaining the perfect playful demeanor and I always welcome men who understand how to treat a genuine wild wom...
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...
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 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 ...
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...
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...
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 ...
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...
May 24th, 2026
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...
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...
Road Head Sally Drivin' Hard in Chicago Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Chicago. Hey, what's the best time for road head? When there's gas in the tank baby! Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or park...
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 ...
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...
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...
Ebony TS Playmate for Men Who Know What They Want 🖤🍆  If you are the type of person who does not want to waste time with games or small  talk… we are already off to a good start 😘 I am a sexy, curvy TS  babe who loves attention, loves giving pleasure, and lives to be desired. I will come looking like  a dream and be read...
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...
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...
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...
🔥 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...
💎 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...
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 ...
🔥 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...

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