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Chat with shemales, transsexuals and ladyboys from Wisconsin 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 Wisconsin. Click the "Enter Chat Rooms" button to create a free shemale chat profile and start chatting now. Not from Wisconsin? All transgender chat profiles are easily searchable no matter where you are. With 34 chatting in the shemale chat rooms and with 420 ladyboy community members online you are sure to find fun transsexual friends to chat with. Join us in the free shemale Wisconsin chat rooms and start connecting.

Popular Nearby Cities: Madison, Green Bay, Milwaukee

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Shemale Chatters in Wisconsin

wisconsinguy49's Chat & Dating Profile
Green Bay, Wisconsin, US
im a single romantic, looking for friends and maybe more, love to find a girl for a nice ltr. am a romantic, big time cuddler, love long walks, giving massages, biking, motorcycles
Nicolej's Chat & Dating Profile
Kenosha, Wisconsin, US
Longtime crossdresser trying to figure out where I go from here.
Gina46's Chat & Dating Profile
Wisconsin Dells, Wisconsin, US
Long time CD girl and love the whole glam thing. For me doing my makeup is very sensual and just absolutely love doing it, taking my time and trying to make it perfect. I am married, wife knows doesn't care, have my own things in my special closet. When she goes away for the weekend, she puts out some things for me to wear while she is gone. When I get home from work, its time to be Gina and let the fashion show begin. Love heels, garters, thigh highs but who doesn't Enjoy role play
eric46's Chat & Dating Profile
Wisconsin, US
Mature, educated, kind, somewhat old fashioned, man with a sense of humor, though I’ve been called dry at times....and a poor sense of timing. Here to chat with interesting people, Like alot of others here, Ive have experimented in my youth with wearing girly things as a teen and enjoyed it at the time. Moved on but always kept a soft spot in my heart for the lifestyle and those in it. I admire your courage and confidence, and of course your choices.
CycleNut938's Chat & Dating Profile
Oconomowoc, Wisconsin, US
Love riding my Harley and playing piano. Also love Role Play. More to follow.
Luciee60's Chat & Dating Profile
Milwaukee, Wisconsin, US
Mature in the closet CD. Love chatting with other like minded cds.
SandyCD's Chat & Dating Profile
Eagle River, Wisconsin, US
Crossdresser that likes to be called names such as bitch, whore, slut or sissy. Don't call me baby, honey or doll. No you can't see my private pics unless you have pics in your profile of YOU. I do private chat if that suits you. No role playing in chat at all!!
BrittneyJessica's Chat & Dating Profile
Milwaukee, Wisconsin, US
Hello I’m BrittneyJessica, Just a Millwaukee girl that enjoys and is intrigued of seduction and romance.
OfficerNasty69's Chat & Dating Profile
Milwaukee, Wisconsin, US
Looking for that sexy girl with big tits, a fat ass, and a rock hard cock! Who wants to give me some?
matztamara's Chat & Dating Profile
Superior, Wisconsin, US
just a farm woman now raise horses and beef cattle now am learning to be a mother
Kaley34's Chat & Dating Profile
Wisconsin, US
I'm new to the whole cd/tv lifestyle looking to meet new people and more. I'm a chef as a career, love sports,board/card games, and also a gamer. I work a lot but i do a lot of relaxing too.
CDDawn75's Chat & Dating Profile
Wausau, Wisconsin, US
Crossdresser, submissive and easy going. I've been crossdressing on and off for the past 15 years. Enjoy exploring all kinds of new kinks. Love to chat.
SpacedSnail7's Chat & Dating Profile
Milwaukee, Wisconsin, US
Hi i am a bit of a shy guy, i love to chat and stuff but sometimes i am just shy at first but i get pretty talky once i am past that. :)
Paddledaddy's Chat & Dating Profile
Milwaukee, Wisconsin, US
69 yo educated business/sports professional. Educated in different BDSM arts.
freddybbwnut's Chat & Dating Profile
Baraboo, Wisconsin, US
bi big boob bbw lover also like she males
MadCityGuy's Chat & Dating Profile
Madison, Wisconsin, US
Gay guy from WI, lived overseas for a while, now I'm here. Always had a close connection with trans folks and I've been on this site for a long time, always looking to meet new people and make new friends.
Stacielynn51's Chat & Dating Profile
Oconto Falls, Wisconsin, US
Hi I been dressing since very young really enjoy dressing up like a woman it feels so good I like skirts wig makeup heels I like to meet new people go to clubs ,events,I am a non smoker I like to drink casually I have no kids I been on a few dates with other CDs like to go out in public
L0verBoy36's Chat & Dating Profile
Sussex, Wisconsin, US
Naughty guy looking Naughty m2f
James1961's Chat & Dating Profile
Milwaukee, Wisconsin, US
Native to Milwaukee, WI An admirer and supporter, I enjoy getting to know others and never tire of hear each woman's story. I enjoy creating new friendships online, but I am realistic as to how quickly they can fall apart. Please don't hesitate to reach out to me if you would like to talk.
Tommy1961's Chat & Dating Profile
Whitewater, Wisconsin, US
Nice single 25 years no dates or sex rusty 4 kids
Diana1k's Chat & Dating Profile
Kenosha, Wisconsin, US
Hi, I'm an author and have midelled for a major store; i like talking over coffee or tea.

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