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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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 ...
TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Chicago
Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
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...
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 ...
FtM seeking Princess Bride in Chicago FtM seeking Woman in Chicago
Hi, I'm Andy, age 33, FtM transgender man living in Chicago. Also, you must love that movie! If you don't get the reference you can still message me anyway! I love that movie and I will watch it with you over and again. View my pics and send me a message @AndyFtM4P...
Tiffany Shelle - Your Chicago Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Chicago
It’s Tiffany Shelle your perfect tranny girlfriend 🥰 💕 SAFE💕 💯 LEGIT ✨💞 SKILLED, Exotic and Erotic 💦 🥰 I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!
I'm 100% functionin...
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...
Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Chicago?
Hey, I am Jasmin, with a great body and busty. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for hot dates and see where it goes!
Hit me up @SweetJasminT...
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...
Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Chicago for Man
Hello, thanks for looking at my ad! I'm Lara. I am 32 years old and transitioned when I was 24 but no surgery other than breast augmentation and some minor body touchups. I pass exceptionally well, fully functional. I'm feminine and classy so you will be pr...
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 ...
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...
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...
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...
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...
Superb Shemale in Chicago... T-Girl for NSA Encounters in Chicago
When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Chicago. 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 and ...
Email Chicago Shemales 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...
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...
Well Endowed Shemale is beautiful Chicago 32 Well Endowed Shemale in Chicago
I am Blanca. I am ready to eat your manhood now. Top or bottom. Bareback if you're clean. Come say hello. I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me at BlancaShemale32 for my latest pictures and proof of my size!&nbs...
Strict Shemale Dominatrix in Chicago - @DesireeTransDomme Powerful African-Queen Dominatrix in Chicago
I am full-time professional Domme Desiree. My Chicago area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you will learn to...
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...
Chicago BDSM Master Taking on New Trans Slaves... I am single minded strict, controlling discipline oriented Master in Chicago 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 more...
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 ...
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 ...
I'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...
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...
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!...
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 ...
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...
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 ...
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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...
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...
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...
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...
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 ...
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...
Debonair Trans dude, looks like Bond F2M Trans Dude in Chicago
Looking for someone a little different from the average guy? Hey, I'm Barry, age 31, fit and healthy. I have a square jaw, sparkling eyes and short dark hair. I like to dress sharp. I am currently looking for a fun lady to spend time with. Possible longterm relationship.&n...
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...
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...
Send Me Sext Messages... I'll show you mine if you show me yours! If you like the show maybe we can get together for some real adult fun. I'm Nina, a trans lady looking for a man for NSA, 28 years old, Italian, bottom, functional and always extra horny. Please be in Chicago, clean, polite, fun and ready for some action. If ...
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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....
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
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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
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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...
Free Illinois Transexuals Guide Illinois Transexuals Guide
The Illinois Transexuals Guide was prepared by our trans experts at AmericanTransexuals.com. We bring trans women and admirers together for friendship, dating and sex hookups. View our free Illinois Transexuals Guide online.
Where to Meet Transexuals in Illi...
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 ...
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...
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...