Chicago, Illinois Shemale Dating Classifieds
Chicago, Illinois shemale dating classifieds. Meet local crossdressers, transexuals and shemales for romance, sex or just make new transgender friends. escorts, body rubs & sex service listings. Select your location below to find shemales near you. It's free to search or post your own ad!
Home / Shemale Dating /
Show Ads In: Bloomington-Normal | Carbondale | Champaign-Urbana | Chicago | Decatur | Peoria | Quad Cities, IA/IL | Rockford | Springfield, IL
Flirty & Feminine CD Ready for Some Fun ππ I’m a sexy, smooth, and playful crossdresser who enjoys the attention, desiring to be treated like a lady. Seeking for a man who can appreciate a well dressed CD for a casual fun night or even something ongoing. I am a pleaser and I want to be pleased. π
π Bath g...
TS Bombshell Looking for a Man Who Can Keep Up! π Chicago Naughty, Nice and Looking for a Thrill!Transsexual Seeking Man for Sexy Fun!
View More of My Pictures πΈ
Are you the sort of man who enjoys just a touch of danger, a touch of excitement, and a lot of passion? I’m the trans beauty you’ve been dreaming of — sexy...
Sassy CD Looking for a Real Man ππ₯ A sweet, sexy and a little naughty crossdresser here, I like to play and flirt, and I need a strong man who knows what he wants. I enjoy the process of dressing up, teasing and bringing fantasies to life. If you are into sensual encounters and passionate fun then let me and y...
π Dark-Skinned TS Beauty Looking for Fun, Passion & Pleasure π I am the Queen of Your Fantasies – Come Worship Me! I am a gorgeous, confident, ebony TS, with a body built for pleasure and a mind full of naughty ideas. If you are looking for high class experience, filled with deep pleasure, seductive touches and sensual moments...
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...
π« Dark Chocolate Delight Ready to Melt in Your Arms π π Hey, Handsome! I’m a sultry, curvy ebony TS here in Chicago... I'm Pre Op, ready to play, with a body made for pleasure and a heart full of passion. Discreet, sensual, and looking for a man who knows how to handle me. Let’s make tonight unforgettable! π I'm writing this to ...
Ebony Shemale in Chicago β€οΈπ Seeking Male for Naughty Fun! Ebony Shemale Stefanie Ready to Fulfill Your Wildest Fantasies π
Are you looking for a hot and kinky black shemale in Chicago? Look no further because I am here to satisfy all your desires. My name is StefanieBBC and I'm an Ebony Shemale.. I am a stunning transgender woman who loves to pla...
Chicago Addicted to shemales... Male Seeking TS A handsome, fit and confident man, seeking a stunning TS girl to spend exciting nights and incredible moments with. I have a thing for flirty conversations, passionate chemistry and playful antics- if you are looking for a casual meet or if we can make this a more regular thing, I ...
Marina TS π 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...
π€ Ebony TS Playmate with a Curvy Body & a Wild Side π Chicago π Thick thighs, soft lips, and a wild side—what more could you want? I’m a sensual, passionate ebony TS beauty who knows how to make a man feel special, desired, and completely satisfied. Whether we take it slow and intimate or dive into a steamy, no-strings-attached night of passion,...
Hungry for Explosive Sex, Fun and Adventure?... Yeah, me too honey! I'm Hope, a black trans woman living in Chicago with all the skills to thrill. Vers top or bottom and love hot sex anyway you can get at it. Im curious, smart, free spirited, and funny. I love to travel, eat good food, watch movies and spend intimate time with my man, and no...
Email Chicago Shemalesβ€οΈβπ₯ 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...
TS Latina Snack β Sweet Like Sugar, Dirty Like Tequila ππΉ You can find me at the bar where I serve drinks and flirt with customers while enjoying the atmosphere. I’m your sexy little TS Latina snack — soft lips, juicy thighs, and a tongue that doesn’t stop until you beg me to π I’ll start off sweet, flirty, &nbs...
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...
Letβs Get a Drinkβ¦ and See Where It Leads π One Night, No Limits... ChicagoShemale Seeking Man for sexπ¦
View More of My Pix - β
Some nights are for breaking rules, for letting go, and for indulging in pure pleasure. I am a trans goddess with a wild side, and I am looking for a man who wants to play. We sho...
I love a confident, seductive TS womanβcould you be the one? π A handsome, intelligent and adventurous man, here looking to meet a gorgeous TS woman to have excitement, chemistry and wild nights. I just love confident women who know what they want and I’m more than ready to spoil, explore and indulge in pleasure together. Handsome,...
Hot TS Latina with Curves, Sass, and a Thirst for You ππ· You are not the typical girl who lives in the next house… You are the woman who occupies your thoughts when you are with the woman who lives next door. Message me here!!
I’m a TS Latina goddess — I have the shape of a coke bottle, the lips of sin, and a t...
Spicy and Hot T-Girl from Colombia Latina T-Girl in Chicago
Hey guys, I am Colleen and I am looking for a long term relationship. I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery. Nice surpise waiting for you! Send me a private message! ColleenLatinaT...
Hot sexy shemale doll visiting Chicago now Shemale Visiting Chicago
Very hot sevy and curvy shemale chick with 8 inch lady stick. Message me on my profile page @TaylaShemale1.
Seeking kind gentleman for romance and fun. Possible long term with the right man. ...
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...
M-F trans woman wants a date I want someone understanding and kind. Please check out my profile and rate me. I am 36, 5 feet 6 and elegant! My name is Lyssa....