Close Menu

Shemale Illinois Chat Rooms

57 Chatting Right Now!

Enter The Free Shemale Chat Rooms!
57 Chatting - 436 Online

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 57 chatting in the shemale chat rooms and with 436 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, Champaign, Rockford, Chicago

Explore More Of United States: Alabama, Alaska, Arizona, Arkansas, California, Colorado, Connecticut, Delaware, Florida, Georgia, Hawaii, Idaho, Illinois, Indiana, Iowa, Kansas, Kentucky, Louisiana, Maine, Maryland, Massachusetts, Michigan, Minnesota, Mississippi, Missouri, Montana, Nebraska, Nevada, New Hampshire, New Jersey, New Mexico, New York, North Carolina, North Dakota, Ohio, Oklahoma, Oregon, Pennsylvania, Rhode Island, South Carolina, South Dakota, Tennessee, Texas, Utah, Vermont, Virginia, Washington, West Virginia, Wisconsin, Wyoming,

Shemale Chatters in Illinois

ChicagoMichelle's Chat & Dating Profile
Chicago, Illinois, US
If you don't have a full profile with a pic, please don't PM. If you can't spell in your profile or don't know the difference between you're and your, please don't PM. I'm sure that sounds awful, but it's like nails on a chalkboard to me. :) I'm an occasional dresser in the Chicago area. I look pretty young for my age (was blessed with a baby face I guess) and my stats are 5'11" (without heels), 145. I'm a (kinda) tall and (kinda) thin one and that definitely comes in handy for the tighter fitting stuff we all love, but I'd love more curves! Dressing for me started very very young and has stayed with me my whole life. Because of my domestic situation I don't get many opportunities to go out as Michelle for a GNO, but I'm always looking for a way to make that happen if the stars align. I love chatting with everyone on here. To those girls who transition in any form to full time, I have a HUGE amount of admiration for your courage, determination and the level of self-awareness that a decision like that takes. I'll always be a big cheerleader for you. Would love to meet other girls in the area. Come find me! :)
Marianne10's Chat & Dating Profile
Chicago, Illinois, US
I am a woman and looking forward to exploring life as a woman
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.
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.
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
Inexperienced1's Chat & Dating Profile
Sterling, Illinois, US
The best thing about me is that I am 100% honest. I NEVER lie. Sometimes that works against me because many people don't like my preferences or boldness. Anyway, this is me: I am an older man and retired. I am married but have no sex. I sit in front of the computer a lot. I am online trying seduce feminine people into cam sex. I watch a lot of porn and masturbate a lot. I am an exhibitionist and voyeur. And I NEVER, EVER send money or things to ANYONE unless I have met them in person first. Does that appeal to you?
bemaibaby's Chat & Dating Profile
Chicago, Illinois, US
nice asian boy that would like to be a girl for a masculine older man.
evefemme's Chat & Dating Profile
Des Plaines, Illinois, US
Started dressing about 7 ago. Did some in my college days, but getting back into it with some help from my wife. Hoping this site can help me along. I would love chatting with other that have been doing it for a while.
IllinoisGuy1982's Chat & Dating Profile
Mattoon, Illinois, US
I am single and easy going looking to get to know good people.
Pete4Femme's Chat & Dating Profile
Chicago, Illinois, US
Clean cut, exec type, masculine and straight looking
TristaW39's Chat & Dating Profile
Chicago, Illinois, US
Hi everyone. I'm a late 30s crossdresser. I’ve dressed since I was little, but I kept it in the closet for so long, just like so many. I’m recently divorced, and since then, I’ve put my efforts into accepting who I am, and growing Trista. I’m loving the journey I’m taking now that I’m living alone, and it’s a blessing to finally to be able to let my femme self out. I’m new to URNA and just looking for chat, friends, and some flirting from time to time!
Nonsuchgirl's Chat & Dating Profile
Champaign, Illinois, US
Non-passing CD. For chat. Searching for mature woman or mature CD. Maybe more?
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
Noclue22's Chat & Dating Profile
Illinois, US
Single looking to meet trans girls to be friends or relationship
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.
GinaMarie's Chat & Dating Profile
Waukegan, Illinois, US
I am Illinois based girl who loves to meet other girls for a glass of wine and conversation. Also travel to Wisconsin to the Milwaukee area occasionally. Love to favorite stores are Loft, VS and Sephora.
RenaissanceFreak's Chat & Dating Profile
Joliet, Illinois, US
Admirer of beautiful, passable TS Queens
connieCHI's Chat & Dating Profile
Chicago, Illinois, US
Full time, post-op lady just looking for friendships. Enjoy simple talk with others going through similar journeys.
Amanda308's Chat & Dating Profile
Romeoville, Illinois, US
20 months post op and loving life

Find More Shemale Chatters In Illinois

© 2012-2023