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Popular Nearby Cities: Wisconsin Dells, 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
Gina46's Chat & Dating Profile
Wisconsin Dells, Wisconsin, US
I have been a CD girl since about age 13. Started out with mothers stuff and that was much to big, but fun. I got caught and she was supportive and got me some of my own things which my father hated. She eventually divorced him and I was able to dress more openly. As I got older I dressed more often, wife knows doesn't care about it. I enjoy doing my makeup and have all my own things in my special closet. I do go out dressed as Gina with no issues. I hardly ever wear skirts or a dress when I go out in public, typically look like a housewife, jeans, peasant top and flats with small amount of makeup. Recently found a bridal gown at a yard sale and it fits, love it, the girl selling it thought I would look good in it kinda goes with my yard sale bridesmailds dress. But Always have to have my lipstick on, never without that. I enjoy role play and will not cam or do phone so don't bother asking.
BrittneyJessica's Chat & Dating Profile
Milwaukee, Wisconsin, US
Hello I’m BrittneyJessica, Just a Millwaukee girl that enjoys chatting and meeting like minded people. Please don’t be bashful and say hello.
Nicolej's Chat & Dating Profile
Kenosha, Wisconsin, US
Longtime crossdresser trying to figure out where I go from here.
CycleNut938's Chat & Dating Profile
Oconomowoc, Wisconsin, US
Love riding my Harley. Love chatting and role play.
SarahAnn317's Chat & Dating Profile
Sturgeon Bay, Wisconsin, US
A lifestyle crossdresser that loves being a gurl. I live the life of a gurl for the most part, 24/7. I consider myself bi-sexual as I enjoy both men and women. I am a bottom only and prefer strong personalities in both men and women. I am 57. Thin build with long blond hair. I am 5'6" and weigh in at about 120 lbs. I consider myself somewhat of an old fashion woman. If you were to look into my closet you find exactly what a woman of my age would wear. I am a retired Mechanical Engineer. I love living in Door County and have no desire to move from the Door as we call it. A few things right from the get-go: I am not interested in an any form of cyber role play. I do not part take in any form of sex chat. After we have built up a rapport, things can change. If you engage in sex chat I will end the chat immediately. So that being said here is my story. I met a woman when I was 14, she was 30. I used to work as a bus boy at an Italian restaurant and we started talking and would hang out. The day after my 16th birthday we had sex for the first time. It was great. She taught me all about how to be with a woman. The day after I graduated high school I moved in with her, much to my parent’s displeasure. While I was living with her I went to the local tech school and took classes in Mechanical Design. Since we were the exact size, I mean right down to height, weight shoe size etc. I had what would be described as a slim female figure. I never had much of a man’s shape, even as a teenager I looked like a girl or more gender neutral. My mother had the hardest time finding clothes that fit me in the boys section. I digress. So since my live in girlfriend loved to make her own clothes, it was the 80's, she would have me model things so she could see how they looked. As time went on one thing lead to another and she would fully dress me up as a girl. Complete with make-up and by this time my hair was longer and she would style it. We even went out as few times with me dressed as a girl. When it was getting time for me to graduate tech school she just up and disappeared. She had a history of doing this, but this time it was much longer. I moved out and took all her stuff and started life on my own. Once on my own and living in downtown Milwaukee I really got into my dressing. Every weekend and when I would come home from work I would go into gurl mode. I made friends as a CD and had a great life. I met a girl and we dated for about 3 years, I was 21 at this time. She enjoyed my dressing but not as a full time thing. Plus she wanted to get married and have kids. This did not interest me at all. So we parted ways and we still stayed in contact but that is about it. We still chat and are good friends but nothing more. When I was 24 or so I met a man at a local gay club. He was a territorial sales rep. He would come up to Milwaukee every 6 weeks or so and I would spend time with him. As stated I was around 24/25 and he was around 45. I would go to his hotel on Friday after work and would stay with him until Saturday when he would head out. He was married but I did not care to much about it. As time went on our relationship got more intense. We started playing around with bondage, mostly hand cuffs, leg cuffs, gags, blindfolds, spankings and some role playing. I started to get deep feelings for this man and he told me he loved me and I as well. This affair went on for about 2 years or so. At one point he stopped calling and I never heard from him again. He dumped me without even a good bye. I was heartbroken. I was 26 or so and was totally crushed! To this day I have no clue what became of him. Since then I have had a few male and female lovers but nothing in the past 20 years or so. I find it hard trying to find someone that I want to be with on that level again. I have a number of friends that fill my void for love and friendship. I live as a gurl most of the time. I have no desire to transition from male to female. I enjoy being a gender bender and love my life. As of last summer, 2022, I have retired to spend more time travelling and doing hobbies. I love to do stained glass work and I also love to make pipe lamps. If you do not know what a pipe lamp is just Goggle it. Still not sure what I am looking for but I always keep my eyes open. Since I have a very active social life I have no desire to move, and since I have been single for so long I have really no desire to have a live in relationship. Just somebody to hang with and have sex with. I am open to both men and women. I am a sub (bottom) and am only interested in people of strong personality. The picture on my profile is old, about 6 years and since then I have dropped all the weight I put on over the years. I am 5'7" tall and weigh about 126s. I am a natural blond and my hair is long. I usually wear it in a pony tail, but on occasion I will style it. I am very fem and love to dress in nice clothes. About the only time I am not in gurl mode is when doing yard work or riding my bike, hard to tuck when riding my bike. For the most part I am pretty friendly so feel free to chat me up. Things that are deal breakers are people that are in any kind of a relationship. I do not care what the circumstances are whether you have an open or are separated etc. You must be totally single! Also you must be fit! I have worked really hard to get back into shape and you must be as well. Also no smokers at all! No recreational drugs either! And your alcohol consumption must be that of a social drinker. You must be intelligent. You must also have some culture about you and not spend all your time watching sports. I enjoy going to plays, musicals and the symphony. I double majored in both Mechanical Engineering and Physics. Also you must have a job or be retired. Thank you for reading about me and hope to chat soon OTHER INFO I consider myself a modern woman more along the lines of a female emulator. I have no desire to transition or take hormones of any kind. I wear everything from shorts, pants skirts and tops, dresses and evening gowns. I have an extensive lingerie collection of bra's, panties and slips. I am looking for a partner not a daddy / mommy or to be owned. For the men folk, I was not put on this planet to give you oral all the time. I do like to have sex as well, often. Also I need a lover that has a good size penis. Simply put. If you are a 6 stroke Stan before you orgasm, that will be a deal breaker. You need to be able to last or have a quick recovery.
Luciee60's Chat & Dating Profile
Milwaukee, Wisconsin, US
Mature in the closet CD. Love chatting with other like minded cds.
donnabicd69's Chat & Dating Profile
Superior, Wisconsin, US
Am married bi love cross dressing admire transgender m to f look so hot sexy drives me wild
meandmywibf's Chat & Dating Profile
Madison, Wisconsin, US
Young curious couple first time don't really know what else to put any questions hit us up.
Fatswifty's Chat & Dating Profile
Owen, Wisconsin, US
I love sucking dick and
toxic112's Chat & Dating Profile
Cudahy, Wisconsin, US
Hi i am 22 year old male single looking for a trangender
KimberlyD's Chat & Dating Profile
Milwaukee, Wisconsin, US
Been cross dressing since I was younger. Fun dressing! Feels freeing although I like being a guy too. Kind of confusing I guess. Hugs!
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.
Jbsucksit's Chat & Dating Profile
Poynette, Wisconsin, US
I'm new to this experience but looking forward to it I'm very excited about this
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!!
matztamara's Chat & Dating Profile
Superior, Wisconsin, US
just a woman rancher now raise horses and beef catttle
Monique0412's Chat & Dating Profile
Lake Hallie, Wisconsin, US
My husband and I a looking to have a good time
69withme's Chat & Dating Profile
Madison, Wisconsin, US
Looking for my fantasy. I'm clean 6'1" 165 want to know anything about me ask
OODicky's Chat & Dating Profile
Kenosha, Wisconsin, US
Just a tattoo artist who loves horror movies, anything written by Chuck Palahniuk, and art. A bit of a dark sense of humor, but it's all in fun. Looking for my PIC.
cawarnke's Chat & Dating Profile
Waukesha, Wisconsin, US
I enjoy all kinds of movies. I am a big Star Wars fan. I love computers and video games. I enjoy watching my favorite tv shows. Every chance that I go out as Cassie Marie shopping is such a great time for me. I just enjoy expressing my female side. I enjoy bondage being tied up and would love to have somebody tie me up. I really want to be hyponitized as a pretty by girl by some hypnotist badly and have a video of the whole thing. I enjoy bondage with me being tied up and helpless. I enjoy wearing my pregnant belly and being a pregnant woman. I like wearing dog collars and attaching a dog leash for someone to pull me along with.
paul52's Chat & Dating Profile
Milwaukee, Wisconsin, US
gray hair blue eyes 5'10" 160 lbs
SnScpl8087's Chat & Dating Profile
Lancaster, Wisconsin, US
Couple looking for fun with women couples and trans, message us
slave4u1960's Chat & Dating Profile
Green Bay, Wisconsin, US
Nice guy with a very submissive side. Chastity? Feminization? Cuckold? Anything is possible!
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.

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