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Chat with shemales, transsexuals and ladyboys from Illinois in our free shemale, ladyboy and transsexual chat rooms. We strive to be totally inclusive. We welcome shemales, ladyboys, MtF, FtM, pre-op, post-op, non-op, transgender, transsexuals, crossdressers, transvestites, intersex, androgynous, gender fluid, gender queer, genetic males, genetic females, significant others and trans community friends. It is easy to start chatting with others in your shemale & ladyboy community members from Illinois. Click the "Enter Chat Rooms" button to create a free shemale chat profile and start chatting now. Not from Illinois? All transgender chat profiles are easily searchable no matter where you are. With 61 chatting in the shemale chat rooms and with 373 ladyboy community members online you are sure to find fun transsexual friends to chat with. Join us in the free shemale Illinois chat rooms and start connecting.

Popular Nearby Cities: Springfield, Peoria, Illinois City, Champaign, Yorkville, Rockford, Chicago

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Shemale Chatters in Illinois

gabaghoul11's Chat & Dating Profile
Chicago, Illinois, US
I’m a gamer. I love Pokémon. Dog person.
JackTransLove's Chat & Dating Profile
Chicago, Illinois, US
Educated professional admirer of cd tv and trans ladies. Love yo chat adore a ltr.
Nora's Chat & Dating Profile
Chicago, Illinois, US
What to say? I'm a guy that likes to dress as a woman on occasion. If you can't smile at the thought, we don't need to chat. I'm an admirer of feminine beauty. So I'm not interested in men (sorry guys). Gender offers many roles: why not revel in them? Norah
SyndeeCD's Chat & Dating Profile
Illinois, US
It all started with my mom's pantyhose. Used to sneak them from the laundry and her drawer whenever I could. Soon as I was home alone I'd be slipping them up my legs getting hard instantly then I was off humping pillows! I thought I was a total freak for having such feelings of lust for pantyhose. Something about cumming in pantyhose and stockings felt so naughty. I pushed my desires down for years, then one time when I was out with my friends I spotted a trans porn magazine in an adult book store and a new lust was awakened. On the cover was a totally hot girl with nice big tits and a cock! Why did I want to suck her cock so bad? Again I thought I was a total freak. This was still years before the Internet and I thought I was completely alone with my lustful feelings about femme clothes and other crossdressers. Now I know I'm not alone and love exploring with others like me.
CentralIL217's Chat & Dating Profile
Mattoon, Illinois, US
I am pretty easy going. Single male looking for friendship or more with the right person. Not looking for cyber sex.
nicoledreams's Chat & Dating Profile
Chicago, Illinois, US
I'm a closet crossdressing sissy gurl looking to explore my femininity
Nonsuchgirl's Chat & Dating Profile
Champaign, Illinois, US
Non-passing CD. For chat. Searching for mature woman or mature CD. Maybe more?
Marianne10's Chat & Dating Profile
Chicago, Illinois, US
I am a woman and looking forward to exploring life as a woman
howie5120's Chat & Dating Profile
Arlington Heights, Illinois, US
64 mwm near Chicago. Like to have fun
brandybea's Chat & Dating Profile
Chicago, Illinois, US
I'm a quiet gurl who has enjoyed dressing since I was 12. Gone through alot of purges over the years, but no longer! I have come to accept who I am and want to enjoy it more . The older I get, the more I love feeling feminine. Have been closeted most of my life, but slowly changing. I love chatting with others almost as much as I love dressing in sexy and pretty clothes. In the last year I have been going out dressed as Brandy and loving it!
stephaniek's Chat & Dating Profile
Sycamore, Illinois, US
Live and travel in the greater Chicago area. Started dressing at age 10 or so with my Mom's silk thigh highs and lace panties - haven't stopped since. Love to talk with similar gurls or understanding males.
Samanthavicky's Chat & Dating Profile
Chicago, Illinois, US
SAMANTHA COCK BITCH Or COCK WHORE THANK YOU. THANK YOU. THANK YOU. !!!!!!!!!!! I am a sissy slut !!!!!!!!!!!! i am a "QUEEN of SPADES" sissy Aunt to my lovely niece Heidi Sissy faggot bisexual Samantha
annabynight88's Chat & Dating Profile
Mount Vernon, Illinois, US
Mainly looking for friends and supporters. Not into 'hard top daddy' types. Men are fine if they're nice but generally enjoy others that understand feminine desires. I like messaging more lately since my chat time doesn't get to happen as much as it used to. Feel free to PM me if you actually message. Seems this isn't the best site to find people that want to converse that way. I do have images with no fake facial applications. Since I'm getting zero traction on this site, I've made them all private for now.
Kendra310's Chat & Dating Profile
West Chicago, Illinois, US
Hi everyone! I have been cross dressing in for as long as I can remember. I just luv being out in the real world. It would be everyday if I could. But my life is quite busy and there seems not to be enough hours in the day, so I make do the best that I can. This aspect of my life is very precious to me and is something I cannot do without. I luv wearing short skirts and heels and being seen. I enjoy meeting people that know how to laugh, have fun and can leave life's problems behind at least for a little while. Someone who can put up with my sarcasm which can be a part of my charm once you get to know me. I'm a very oral girl that just luvs pleasing my guy. Hugs.... Kendra
MichelleIL's Chat & Dating Profile
Oak Lawn, Illinois, US
Hi girls! Been dressing privately for years now and I would like to make friends and go out. I love all things satin. I'm hoping to meet other girls to show me how to dress and to help out with styles and makeup.
Jamalbi4fun's Chat & Dating Profile
Chicago, Illinois, US
In my eyes all you ladies are espicial and hot.
Cynthia's Chat & Dating Profile
Chicago, Illinois, US
Female joining to learn more about crossdressing as someone close to me just recently started crossdressing.
Amanda308's Chat & Dating Profile
Romeoville, Illinois, US
Post op woman, and loving life
DeeAnna50's Chat & Dating Profile
Danville, Illinois, US
I am a tell average built middle age crossdresser wanting to finally come to terms with my inner woman. Hoping to find friends for chat or hang out! Prefer my age or older!!!!!

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