Close Menu

Shemale Illinois Chat Rooms

52 Chatting Right Now!

Enter The Free Shemale Chat Rooms!
52 Chatting - 379 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 52 chatting in the shemale chat rooms and with 379 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, 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

Nora's Chat & Dating Profile
Nora
Chicago, Illinois, US
Online
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
tammiebicd's Chat & Dating Profile
tammiebicd
DeKalb, Illinois, US
Online
I'm fun, not so serious, open-minded, easy-going, smart, weird, tantric and likely other things (but not a furry!), I have an absurd sense of humor, but not exclusively so. I also have quite a naughty mouth at times, and I'm never against such chat, but I don't want that all of the time, you know? I am a real person and not simply a muse (though I don't mind being just the latter sometimes). It's fine, e.g., to PM me with "Hi bitch" or "hi slut" if you already know me. I know that I am hardly "everyone's cup of tea". As you can tell by now, I am not very committal. I am bigender, but when I'm online here, you KNOW which one I am! My sexuality is bisexual if I am presenting feminine and heterosexual otherwise. That is not to say, though, that it is not OK to communicate with me as the persona I am not currently presenting as (but keep it on the down-low, in that case, OK?). I need to lose 10-15 lbs, as I am 165 right now and I don't like being so thick in the waist in side view (even with a corset on). I like other tgirls very much and think a tgirl party would be lots of fun. A 3-day-weekend getaway somewhere perhaps? A week? Month? Year?! :) When I signed-up here, I used 'CD' in my nick to not raise expectations too high, but now I regret that decision. I should have used 'TG', as "bigender" is under the transgender umbrella (and 'BG' would be confusing to many people, I think). I am not "transitioning", i.e., not seeking to become a TS (I'm too old and, moreso, I'm not pretty, but hopefully acceptable, if only barely so, with makeup on and my hair styled). My hair is short and my profile pic has me wearing a wig (it is worn out now, and I don't wear it anymore). I am letting my hair grow long, but I have a feeling that some employer is going to demand I cut it at some point. I may cut it on my own accord if gets to be too much to control and I end up looking bad most of the time that I am not presenting feminine (which is not that often, BTW, though I would prefer more often). I read on someone's profile that he thinks that this site is pure fantasy and no one wants to meet. Well, in my case, that is not true, it's just that I have to get my act together, get a job or otherwise generate income, buy all new clothes and see what I can do with my face. (Was that "too much info"?). So, nothing tomorrow, then, and I'm not in a hurry (but you KNOW how I get when I'm horny!) but sometime in the future, for sure, if someone(s) find me worthy for some purpose(s).
Inexperienced1's Chat & Dating Profile
Inexperienced1
Sterling, Illinois, US
Ofline
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?
SyndeeCD's Chat & Dating Profile
SyndeeCD
Illinois, US
Ofline
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.
Amanda308's Chat & Dating Profile
Amanda308
Romeoville, Illinois, US
Online
12 months post op enjoying life
AmberHose's Chat & Dating Profile
AmberHose
Danville, Illinois, US
Chatting
Hi, how are you? I am a 43-year-old male crossdresser here looking for friends and chat. Would love to find a friend. I'm very closeted but ready to try and see where this can go! I love shopping and everything outdoors.
Jenna75's Chat & Dating Profile
Jenna75
Chicago, Illinois, US
Online
I'm a pre op MTF. I don't know what else to say I'm me and that's all I can br
GinaMarie's Chat & Dating Profile
GinaMarie
Waukegan, Illinois, US
Online
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 shop...my favorite stores are Loft, VS and Sephora.
ChicagoMichelle's Chat & Dating Profile
ChicagoMichelle
Chicago, Illinois, US
Ofline
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 tall and 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! :)
stephaniek's Chat & Dating Profile
stephaniek
Sycamore, Illinois, US
Online
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.
3ILguy217's Chat & Dating Profile
3ILguy217
Mattoon, Illinois, US
Ofline
I am single. Looking for friendship or more with the right person. I am non-judgemental and pretty easy going. Live in a rural area so can be hard to meet others. Note - I am not into cybering.
isucktsdick6969's Chat & Dating Profile
isucktsdick6969
Rockford, Illinois, US
Ofline
White loves sucking tranny dicks 6"2 200 29 topbutsucksshecocks is my kik
t160200's Chat & Dating Profile
t160200
Naperville, Illinois, US
Ofline
I am new here but have long dreamt finding a clean safe partner. Primarily looking for m2f or CD but open to any safe play. I am looking for friends with common interests even if platonic.
Samanthavicky's Chat & Dating Profile
Samanthavicky
Chicago, Illinois, US
Ofline
SAMANTHA COCK BITCH Or COCK WHORE THANK YOU. THANK YOU. THANK YOU. !!!!!!!!!!! I am a sissy slut !!!!!!!!!!!! i am a "QUEEN of SPADES" sissy https://ru.xhamster.com/videos/sissy-cock-zombie-hypno-bbc-edition-xhcnF83 https://ru.xhamster.com/videos/tbbc-training-9143337&from=player_related https://xhamster.com/videos/sissystudent-guide-to-bbc-addiction-13346562&from=player_related https://xhamster.com/videos/sissystudent-bbc-study-session-13346557 https://xhamster.com/videos/sissystudent-bbc-research-13346554 https://xhamster.com/videos/sissystudent-bbc-addiction-13346565 https://xhamster.com/videos/sissystudent-bbc-brain-warp-13346560 https://xhamster.com/videos/white-bois-extinction-ariana-g-xhy3TAchttps://ru.xhamster.com/videos/sissy-joi-xhV6yvj Aunt to my lovely niece Heidi https://ru.xhamster.com/videos/love-xh8eamZ Sissy faggot bisexual https://ru.xhamster.com/videos/your-faggoty-truth-is-beautiful-12930831 Samantha
MichelleIL's Chat & Dating Profile
MichelleIL
Oak Lawn, Illinois, US
Ofline
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.
KissableKim's Chat & Dating Profile
KissableKim
Naperville, Illinois, US
Ofline
Hello there, I'm Kimmie, a closeted cross-dresser looking for a safe and discreet way to explore my feminine side. I have always wanted to be feminine, but I've kept this part of myself hidden for most of my life. I'm a bit shy and hesitant about putting myself out there, but I hope to find someone who can appreciate me for who I am. And who I dream of becoming.
TristaW39's Chat & Dating Profile
TristaW39
Chicago, Illinois, US
Ofline
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 divorced over a year ago, 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!

Find More Shemale Chatters In Illinois

© 2012-2023 chat.chicagoshemalesex.com.