Shemale Wisconsin Chat Rooms

Been cross dressing since I was younger. Fun dressing! Feels freeing although I like being a guy too. Kind of confusing I guess. Hugs!

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.

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

Love riding my Harley and playing piano. Also love Role Play. More to follow.

Mature in the closet CD. Love chatting with other like minded cds.

Longtime crossdresser trying to figure out where I go from here.

Wis daddy looking for hot fun

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!!

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. So that being said her 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.

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.

Hello I’m BrittneyJessica, Just a Millwaukee girl that enjoys chatting and meeting like minded people.

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. I go out as Gina, but try to dress down when I do that, most of the time. 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

I am a pre-opt, M2F, 36B (D w/forms) - 28 - 33, 150 lb, DDF, transitioning, 24/7 woman. I enjoy hiking, backpacking, camping, and motorcycling. I have been living as a woman since 2011. I enjoy NSA relationships, friendship, and companionship, especially when I travel or play in the bedroom. Unclockable's have been a blessing, allowing me to dress in anything including women's tight clothes, thong bodysuits, and 1 or 2 piece swimwear. It is so nice to finally wear a 2 piece, Itsy bikini!!!

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. :)

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.

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.

I'm always horny

Want it all

just a woman rancher now raise horses and beef catttle

Just trying to find my missing piece.

Lifelong crossdresser with a wide variety of interests. Let's chat and see what happens.

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.

just here to chat )

Just looking for some chat and taking it from there