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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 20 chatting in the shemale chat rooms and with 378 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.

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Shemale Chatters in Illinois

bighoss832's Chat & Dating Profile
Granite City, Illinois, US
Looking to chat and see where it leads.
Cynthia's Chat & Dating Profile
Chicago, Illinois, US
Female joining to learn more about crossdressing as someone close to me just recently started crossdressing.
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.
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
BBCdressedbTm's Chat & Dating Profile
Bloomington, Illinois, US
I have been wearing lingerie and or bra/panties for years. I am now wanting to explore it more. I am a part time Crossdresser. I still live my life as a man but in my spare time I like to dress up and meet with or chat with other who either dress as well or are admires. I'm bi, bottom, and open to almost anything. Clean chats are good, dirty chats are better.
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.
Tarab4u4fun9669's Chat & Dating Profile
Chicago, Illinois, US
I am back and ready to have some fun
Marianne10's Chat & Dating Profile
Chicago, Illinois, US
I am a woman and looking forward to exploring life as a woman
Uglyman's Chat & Dating Profile
Batavia, Illinois, US
I like to read and heard music
tammiebicd's Chat & Dating Profile
DeKalb, Illinois, US
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).
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 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!
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.
Quantum's Chat & Dating Profile
Chicago, Illinois, US
Hi my name is Jon, I live in the NW side of Chicago. I am a youthful, masculine, safe, healthy, energetic, passionate, respectful, 52, 6' 225 male, professional (Business Analyst downtown), non-smoker, light drinker, no drugs, sometimes 420, loves good food, music and movies. I have had relationships, in varying degrees with tg women in the past, something I have enjoyed since HS. Chatty, especially after a couple of espressos. Pic should be updated, I had a haircut yesterday, very short, and trimmed the beard. See ya. I also can be contacted at quantum_rush at y ahoo dot com
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.
DawnP's Chat & Dating Profile
Tinley Park, Illinois, US
I love becoming Dawn and transforming into the woman I want to be. Getting all dressed up is very sensual. Wearing feminine lingerie, nylon stockings, and high heels makes me feel wonderful. Putting on makeup, jewelry, and perfume makes me feel ultra feminine. Spending an evening with a Friend, TG, TV, TS, or GG is so exciting. Just kissing and caressing is wonderful. I would like to meet someone who shares my interests, being romantic, and sensual.
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!
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 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! :)
justinvar's Chat & Dating Profile
Chicago, Illinois, US
from Chicago. i cant think of anything clever.
Dewayne's Chat & Dating Profile
Freeport, Illinois, US
Adventurous outgoing spontaneous testing the waters
Tpnudists's Chat & Dating Profile
Tinley Park, Illinois, US
Fit closet cross dresser interested in chatting
Amanda308's Chat & Dating Profile
Romeoville, Illinois, US
Just a girl, that’s trying to be as feminine as possible

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