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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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 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...
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...
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...
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...
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...
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 masseur, hot body and hung. If you want to get together, Send me a private message Crystal27trans <3 ...
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...
Superior Massage by gorgeous T-Girl T-Girl for Dating in Chicago
I will help you unwind and create a cozy environment for you! I am hot and sweet and can give you so much pleasure. View my Transgender World profile and message me for my pics! @GayleTGirl
Gayle 😍
Transgender World Profile
Username: GayleTGirl
Locati...
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...
Black/Ebony Transsexual - Your New Addiction – One Taste and You’ll Beg for More 🍑💋 Warning: I’m addictive 😘 View My Ebony TS Profile here -
I possess more than attractive features. I am a complete TS woman who enjoys teasing and pleasing while taking control of your dreams. My body features long legs and thick thighs and soft lips and a hidden secret th...
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...
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...
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 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...
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...
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
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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!...
Having 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....
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...
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 ...
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...
Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice!
Hey boys, my name is LethaWeapon here in Chicago 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,...
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...
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 trans chick with nice boobs Hot trans chick in Chicago. Sheila wants to meet you. Hey all, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, top or bottom, love oral sex. Want to explore kinks? Me too!! Want to meet me? Send me a message @HotTransChick...
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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...
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 ...
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!"
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Shemale Gia's Chicago Sexbook @ShemaleGia27
Photos: 42
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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...