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!
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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...
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...
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...
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. ...
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...
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...
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...
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...
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 ...
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...
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 ...
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...
Looking for Love and Adventure! 🌈
Hey there, lovely people of Chicago! My name is Janey, and I'm a proud transgender woman who's ready to embrace life, love, and everything in between. 💖
I believe that being true to ourselves is one of the most beautiful things we can do. As a member of the LGBTQ+ community, I've found so much...
Sultry Transgender Beauty Looking for Love in Chicago
Hey there! I'm Lora, a confident and sassy transgender woman living in the Windy City. I may not fit society's standards of beauty, but I rock my curves with pride. Being transgender has opened my eyes to a whole new world of self-discovery and acceptance, and I wouldn't have it any other way.
I...
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...
SHEMALE HOOKUPS! Wanna Have a Great Time in Chicago, Illinois? HOT! SHEMALE HOOKUPS
"The girl with a naughty little secret in her panties!"
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Spicy Hot 🌶 Tranny Girl from Colombia Latina Tranny Girl in Chicago
Hey guys, I am Gabriella and I am looking for a longterm relationship with a gentleman who love sex as much as I do! I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery except breasts. I am smooth and clean, very feminine...
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...
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...
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...
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...
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...
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...
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...
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...
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 ...
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...
Raunchy Shemale Seeking Local Man for Wild Fun
I'm a naughty shemale looking for a hot man in Chicago who can handle all my dirty desires. My name is Stormie and I want to show you a good time. I love getting down and dirty, so if you're into that, hit me up!
I enjoy being both a top and bottom, giving blowjobs, getting my tight ass fucked ha...
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...
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...
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...
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...
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...
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...
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 ...
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 ...
Hot Shemale Juliann Seeking Local Man for Wild Fun
Looking for a man who can handle a tranny like me? Look no further! I'm Juliann, a sexy shemale from Chicago, Illinois, ready to show you a good time. I love getting down and dirty with a guy who knows how to please me in all the right ways. Whether you're into sucking my throbbing cock or lettin...
Hot Shemale Vivian Looking for Naughty Fun in Chicago
Are you ready for a wild time with a sexy shemale in the Windy City? I'm Vivian, and I'm on the hunt for a local man who can handle all of my filthy desires. I love to get down and dirty, exploring every inch of your body with my throbbing cock and tight ass.
I'm a top who loves to take control, ...
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...
Sexy Transgender in Chicago Looking for Love
Hey there! I'm Kathie, a fun-loving transgender woman living in the Windy City. I may not fit society's norms, but that's what makes me unique and fabulous. I embrace my LGBTQ identity and love being part of such a diverse community.
I enjoy cozy coffee dates at local cafes like Intelligentsia or...
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...
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...
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 ...
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.
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Sexy Transgender in Chicago Looking for Love
Hey there, I'm Jessy, a sassy transgender babe living in the Windy City. I love exploring all the amazing LGBTQ-friendly spots in Chicago, like Boystown and Andersonville. I'm always down for a cozy coffee date at Intelligentsia or a fun night out dancing at Berlin.
Being trans has allowed me to ...
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 ...
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...
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...