Chicago Transgender Sex Ads
Browse Chicago transgender sex ads to meet local transexuals, crossdressers and shemales for sex, dating or friendship. It's free to search the trans sex classifieds, or post your own adult ad!
Home / Alternative Sex Ads / Transgender Sex Ads
Show Ads In: Bloomington-Normal | Carbondale | Champaign-Urbana | Chicago | Decatur | Peoria | Quad Cities, IA/IL | Rockford | Springfield, IL
Transgender Cutie Seeking Love in the Windy City! 💕
Hey there, lovely people of Chicago! My name is Deeann, and I'm a proud transgender woman looking for that special someone to share my journey with. 🌈
So, let me tell you a bit about myself. I have a curvaceous body that will make you weak in the knees. 😉 With my radiant smile and warm pers...
Sweet and Sensual Transgender Beauty Looking for Love
Hey there, I'm Beverlee from Chicago, Illinois. I may not fit society's typical mold, but that's what makes me unique and special. I love being part of the LGBTQ community because it allows me to express myself authentically and embrace who I truly am.
I enjoy long walks by Lake Michigan, explor...
Sexy Transgender Babe Looking for Love in Chicago
Hey there, I'm Dedra from Chicago, Illinois. I may not fit society's idea of "normal," but that's what makes me unique and special. Being transgender has allowed me to embrace my true self and live authentically. I love being part of the LGBTQ community because it's a place where I feel accepted a...
Raunchy Shemale Seeking Local Man for Wild Fun
Are you looking for a hot shemale to fulfill all your wildest fantasies? Look no further, because I'm Kailey and I'm ready to show you a good time. I'm a sexy shemale from Chicago, Illinois, seeking a local man who can handle my insatiable appetite for pleasure.
When it comes to sex, I love it a...
Exploring Love and Connection as a Transgender Beauty
Hey there, I'm Vicky from Chicago, Illinois. I may not fit into society's typical mold, but that's what makes me unique and beautiful. I embrace my transgender identity and love being part of the LGBTQ community.
I enjoy spending time at local coffee shops like Intelligentsia or exploring the ar...
Looking for Love and Adventure in the Windy City! 🌈
Hey there, lovely people of Chicago! My name is Muriel, and I'm a proud transgender individual ready to embrace life's incredible journey. 💖
Living in this vibrant city has allowed me to fully express my authentic self, and I couldn't be happier. Being part of the LGBTQ community has taught me...
Raunchy Shemale Seeking Local Man for Wild Fun Hey sexy studs, I'm Glory, a hot shemale from Chicago looking for a man who can handle all of me. I love it all - from deepthroat blowjobs to getting my tight ass pounded hard. If you're into kinky play and want to explore your wildest fantasies, then I'm the tranny for you.
I enjoy being both a to...
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 ...
Transgender Beauty Looking for Love in the Windy City
Hey there, lovely people of Chicago! My name is Dory, and I'm a proud transgender woman who's ready to dive into the dating scene. 💃🌈
As a true Chicagoan, I embrace the city's diverse culture and vibrant energy. Whether it's exploring art at the Art Institute or catching a Cubs game at Wrig...
A Sensual Journey of Self-Discovery
Hey there, I'm Karrie from Chicago, Illinois. I may not fit society's idea of "normal," but that's what makes me unique and special. Being transgender has allowed me to embrace my true self and connect with others in the LGBTQ community.
I love exploring the vibrant nightlife in Boystown, grabbin...
Looking for Love and Adventure - Transgender Dating
Hey there! My name is Bridgett, and I'm a proud transgender woman living in the vibrant city of Chicago, Illinois. 💃🏼
When it comes to appearances, picture me as a curvy and confident lady with a contagious smile. I embrace my unique blend of ethnicity and nationality, which adds an excitin...
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...
INTERACTIVE MAP: Transexual Tracker in the Chicago Area! Local Trans Hookups Interactive Mapping
Meet Local transexuals in the Chicago area for friendship or sex hookups. View member thumbnails on the interactive map below to meet local members who want to meet local transexuals or admirers. Click any member photo below to get started. Sign up free for i...
Elegant Trans Beauty Seeks Connection
Hey there! I'm Garnette, a transgender gal from Chicago who's looking to meet someone special. I may not fit society's standards of beauty, but I embrace my unique body type and ethnicity with pride. Being part of the LGBTQ community has allowed me to explore my true self and connect with others w...
Sparkling Transgender Beauty Looking for Love
Hey there! I'm Lindie, a transgender woman from Chicago who loves exploring the city's diverse neighborhoods and trying out new restaurants. I may not fit into society's traditional gender norms, but that's what makes me unique and proud to be part of the LGBTQ community.
I enjoy long walks by L...
Hot Shemale Looking for Local Man to Play With Hey sexy, I'm Merrill and I'm a naughty shemale from Chicago looking for a man who can handle all that I have to offer. I love getting down and dirty, so if you're into some wild fun, then I'm your girl...err, shemale!When it comes to sex, I'm open to just about anything. I love giving and receiving...
Discover the Magic of Love with Rhianon! Hey there, lovely people of Chicago! My name is Rhianon and I'm thrilled to be part of this amazing LGBTQ community. 💖 Being transgender has allowed me to embrace my true self and experience life from a unique perspective. It's been quite a journey, but I wouldn't change it for the world! I'm ...
Shemale Nightclubs Near You in Chicago, Illinois Shemale Nightclubs Near You in Chicago, Illinois
Shemale Clubs Near You in Chicago, Illinois is a directory of trans-friendly nightclubs and bars. LGBTQ+ clubs come and go. We strive to keep this transgender clubs directory complete and rely on your input to help us do so. Please contact us if yo...
Gorgeous, Passable Trans in Chicago 😍 Gorgeous Passable Trans MtF for Man in Chicago 😍
I transitioned 6 years ago at age 18. I am pretty, with long light brown hair, a nice figure and long shapely legs. I have brown puppy dog eyes and kissable lips. Check my profile @TransFaye24 for pics and prepare to be stunned!
I'm ki...
HMU for Sex in Chicago Newly Single and Ready to Mingle in Chicago
Hi guys, my name is Barbie, age 28. My husband cheated for the last time. Now it's my time to have some fun! If you want to hook up for passion and hot sex in the Chicago, Illinois area then message me @BarbieSingle28.
...
Hot Shemale in Chicago Looking for a Wild Time!
Are you ready to have some naughty fun with a sexy shemale named Joell? I'm looking for a local man who can handle all of my desires and fantasies. I love being both a top and bottom, giving blowjobs, getting my ass licked, sucking dick, and riding cock like there's no tomorrow. I want to make you...
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...
Looking for Love and Adventure in the Windy City! 🌈
Hey there, lovely people of Chicago! My name is Opaline, and I'm a proud transgender person who's ready to embrace life, love, and everything in between. 💖
So, let me tell you a bit about myself. I have a unique body type that will make you want to give me endless bear hugs. 🐻 My ethnicity ...
A Sensual Journey with Maddy
Hey there, I'm Maddy, a fun-loving transgender babe from Chicago. I may not fit society's standards of beauty, but my confidence and charm will sweep you off your feet. 🌈
I love exploring the diverse LGBTQ scene in the city, whether it's dancing the night away at Berlin Nightclub or enjoying a...
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...
Meet Illinois Transexuals Online: Live Chat, Member Profiles, Photo Swaps & Local Trans Clubs Meet Illinois Transexuals Online!
Meet Illinois transexuals online at AmericanTransexuals.com. Our web development team includes transexual women and male trans admirers, so we have a unique understanding of transgender attraction. We have created an online community where you can meet Illino...
Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Chicago?
Hey, I am Jasmin, 8" 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...
Naughty Shemale Looking for a Wild Time in Chicago Hey boys, I'm Jerry and I'm a sexy shemale looking for a local man who can handle all my dirty desires. When it comes to fun in the bedroom, I'm not shy about what I like. I love giving sloppy blowjobs, getting my tight ass pounded hard, and riding a huge throbbing cock until we both explode with or...
Brandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Chicago
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 naughty fan...
Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖 Preop Trans in Chicago
Hi! I'm Brandi, new TS in the Chicago area. I'm MtF preop transexual woman. I pass as female very well so we can go to your business function or out for dinner followed by a night of forbidden fun that only we will know about! I am fully functional, 8" thick hiding in my pant...
27 y/o Sexy Hung Crossdresser in Chicago Hung Crossdresser for Male in Chicago
Hey, I go by Selena when I'm cross dressed. I love being feminine and servicing my man!, I'm age 27, well hung and so cute when I'm dressed up!! What more could you want in a gurl?!! View my pics and message me @Selena27femCD so we can talk and meet for a sexy ...
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 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: GayleTGi...
Well Endowed Shemale for Man in Chicago Hung Shemale for Man in Chicago
I am Blanca. I can provide top or bottom service. Bareback if you're clean. Love oral sex both giving and receiving. Say hello cause I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me privately at BlancaShemale32 for my latest uncenso...
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...
Seeking a Local Man for Hot Shemale Fun in Chicago
Are you looking for a wild time with a sexy shemale? Well, look no further because I'm here to fulfill all your naughty desires. My name is Carlynne and I'm a hot tranny ready to play with you.
I love getting down and dirty, so if you're into some kinky fun, I'm your girl. I enjoy giving blowjobs...
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...
Transgender Beauty Looking for Love
Hey there! My name is Mandi and I'm a transgender woman living in Chicago, Illinois. I have a curvy body and I love embracing my Latina heritage. You can check out my pics at my personal profile page @mandic21518.
I'm proud to be part of the LGBTQ community and I enjoy being able to express my tr...
SHEMALE HOOKUPS! Wanna Have a Great Time in Chicago, Illinois? HOT! SHEMALE HOOKUPS
"The girl with a naughty little secret in her panties!"
SIGNUP FREE: INSTANT ACCESS! Shemale Profiles
Browse Uncensored Photos, Swap Your Pics, Join Live Web Cams, Swap Private Messages, Sext & Hook Up!
Join free for Instant Access to the Chic...
Transgender Beauty Looking for Love in Chicago
Hey there! I'm Carolina, a proud transgender woman from the Windy City. I may not fit society's traditional mold, but that's what makes me unique and beautiful. I love being part of the LGBTQ community because it's full of love, acceptance, and diversity.
I'm looking for someone who can apprecia...
Hot Shemale in Chicago Looking for Wild Fun
Are you ready to experience the ultimate pleasure with a sexy shemale? Lucky here, and I'm on the hunt for a local man who can handle all of my dirty desires. I love getting down and dirty, so if you're into some raunchy fun, then I'm your girl.
I'm a top shemale who loves to dominate in the bedr...
Rosanne the Raunchy Shemale Ready to Play in Chicago
I love nothing more than getting down and dirty with a man who knows how to handle a hot shemale like me. My name is Rosanne, and I'm on the hunt for a local guy who can satisfy all my cravings. From deepthroating blowjobs to rough anal play, I'm up for anything that will leave us both moaning in ...
Spark Up Your Love Life with Marta!
Hey there! I'm Marta, a fun-loving transgender gal from Chicago, Illinois. I may not fit society's mold, but that's what makes me unique and fabulous! 🌈
I enjoy being part of the LGBTQ community because it allows me to express myself freely and authentically. It's all about love and acceptance...
Looking for Love and Adventure!
Hey there! My name is Karie, and I'm a transgender woman living in the beautiful city of Chicago, Illinois. 🌆
So, let me tell you a bit about myself. I have a unique body type that will make you feel like you're hugging a fluffy cloud ☁️. I come from a diverse ethnic background, which adds...
Sultry Transgender Beauty Seeks Connection
Hey there! My name is Rayshell and I'm a proud transgender woman from Chicago, Illinois. I may not fit society's typical mold, but that's what makes me unique and special. 💃
I love exploring the vibrant LGBTQ community in Chicago and checking out local spots like Boystown for a fun night out. ...
Elegantly Transcending Boundaries
Hey there! I'm Jennine, a transgender woman from Chicago, Illinois. I love exploring the diverse neighborhoods of the city like Wicker Park, Lakeview, and Pilsen. If you're looking for someone who enjoys being their authentic self and embraces the LGBTQ community, then look no further!
I find bea...
New Body New Me M2F post-op in Chicago
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 Natasha...
TS M2F Top in Chicago TS Top Seeking Man in Chicago
I'm Sandi wants to meet hot guy for fun and hot sex. Age 28 with long blonde hair, smooth skin and a great body. Non op functional, nice big ladystick for your pleasure! 😈 Love oral sex, anal sex and yummy kinks of all sorts. I love to explore kinks and ...
Hot Shemale in Chicago Looking for Some Naughty Fun
Are you ready to have the time of your life with a sexy shemale like me, Bernadette? I'm on the hunt for a local man who can handle all the kinky and wild things I have in store. When it comes to sex, I'm not shy about what I like. From deepthroating your cock to riding you hard and fast, I want ...
Hot Shemale Myrna in Chicago Ready to Play Hey there, I'm a sexy shemale named Myrna looking for a local man in Chicago who can handle all my naughty desires. I love being both a top and bottom, giving and receiving blowjobs, getting my tight ass pounded, and riding a throbbing cock until we both explode with pleasure. I'm into all kinds of ...