Illinois Trans and Crossdressers Classifieds

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February 7th, 2026

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...

SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Illinois Secret Crossdressing Hookups in Illinois 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 ga...

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...

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 ...

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

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 Illinois tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer tha...

Tiffany Shelle - Your Illinois Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Illinois 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% functioni...

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

Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Illinois 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 se...

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....

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...

I'm the Girl Mother 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 Illinois 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 n...

Marina TS 🍆 Visiting and Ready Visitng Houston, Texas - Your TGirl Escort Hi guys Marina TS visiting your city …. We can start a sexy friendship, but if you are generous, it would not be bad. Please call me and text me when you are ready....MESSAGE ME HERE. Sexy, latina, femenine and beatiful TS woman here. English/e...

Superb Shemale in Illinois... T-Girl for NSA Encounters in Illinois When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Illinois. 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 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 I...

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

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 Illinois area come see if you measure up! Click here for explicit photos. Look ...

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 ...

Brandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Illinois Beautiful Brandi. If you're attracted to the female form then you will want to message me @ BrandiTS27.  I'm pre-op, tall, slim and beautiful with 8.5 inches for top or bottom. I love oral sex!! Kink friendly, have toys to explore all your naug...

F/M seeking love and fun Female to Male Trans Man in Illinois 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 gr...

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

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

Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Illinois 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...

Hi Guys!! I am looking for someone fun! This is Lara and I am 41 and transitioned when I was 24. I pass exceptionally well and you will be surprised at my hidden skills. Call me! ...

!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Illinois Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Illinois 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 ...

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

Your Flirty CD Sweetheart Awaits 💕😘 Illinois 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 ...

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 ...

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

New Body New Me M2F post-op in Illinois Hi, I'm Natasha, newly transitioned and ready to date. Gorgeous red head 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 me. Message me online Natash...

I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Illinois ) Sexy Crossdresser Elissa Looking for Hot Fun in Illinois💋    Do you like knowing I'm a man in womens clothes.. do I look sexy??    - VEW MY CD PICTURES Are you wanting to satisfy your innermost desires with a sexy shemale such  as myself? My name is Elissa and I am a ...

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

I Need a Sexy Man to Tame Wild Willy! Hung Illinois Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Illinois 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 ...

Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Illinois 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'...

Well Endowed Shemale is beautiful Illinois 32 Well Endowed Shemale in Illinois 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!&nb...

Flawlessly gorgeous trans bombshell in Illinois Trans MtF for Man in Illinois I transitioned 6 years ago at the age of 18. I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am 5 feet 7 and have deep blue eyes and luscious lips. Check my profile pics @TransFaye24 pics and prepare to be stunned! Send your ...

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 ...

I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Illinois I'm queen Delilah a trans woman here in Illinois 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 positi...

Trans Playmate Sex Kitten... Ebony trans woman in Illinois 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...

February 6th, 2026

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 ...

TS m/f switch 28 new here TS m/f Switch in Illinois Sandi wants to meet hot guy for fun and hot sex. Age 28, nice build, 7.5". Non op functional. Love oral sex, anal sex and kinks of all sorts. View my profile and message me here @SandiSwitchTS...

Illinois's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Illinois Hi you sexy man! I'm Toni a trans woman from here in Illinois. 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 lov...

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 Illinois area. Click here and come see me anytime!...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Illinois I will help you unwind and create a cozy environment for you! I am 36DD, 7" and can give you so much pleasure. View my Transgender World profile and message me for my pics! @GayleTGirl Gayle <3    Transgender World Profile Username: GayleTG...

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 and send message for date....

Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Illinois Look no further honey, I'm Franny an Ebony trans woman here in Illinois 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 t...

Sexy hung and big busted Hung and Busty Shemale in Illinois 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....

Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 I'm in Illinois 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.. L...

TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Illinois Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...

Tantalizing Tina with a HUGE W33NAH! Illinois Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Illinois men and wnat to show you a time you'll never forget! Do you like them thick, long and uncut? Then I'm the girl for you. Look no further for a passible and functional t girl - HERE I AM!  About me:...