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Chat with shemales, transsexuals and ladyboys from New York 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 New York. Click the "Enter Chat Rooms" button to create a free shemale chat profile and start chatting now. Not from New York? All transgender chat profiles are easily searchable no matter where you are. With 44 chatting in the shemale chat rooms and with 367 ladyboy community members online you are sure to find fun transsexual friends to chat with. Join us in the free shemale New York chat rooms and start connecting.

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Shemale Chatters in New York

Alisoninheels's Chat & Dating Profile
New York, New York, US
I am married but dress as often as I can - wife knows but prefers not to be around when I dress. She doesn’t know that I love men and crave cock. Very submissive
KerryLynn79's Chat & Dating Profile
Fleming, New York, US
TS bi-sexual woman into making friends on here. Attracted to women (and some men) of all kind. Currently in a relationship with a long-time male friend. Very happy about our relationship.
SaraJen's Chat & Dating Profile
Fishkill, New York, US
48 yo post op ts loves chatting with Dominant men. My early years. I have been dressing and known I was a girl since I was 4 or 5. In middle school and high school I would come hone alone everyday and dress in my moms stuff head to toe. By high school I was starting to buy my own shoes and lingerie. By college I had my own complete wardrobe. I knew I would transition one day but absolutely needed to know that I could pass 100%. I was a 19 yo sophomore in college and had a gf of 9 months. I told her my Halloween costume was a secret. I went all out. Shaved every inch of my body not that I had much body hair, got a manicure and pedicure and eyebrows waxed. I wore a skin tight black mini skirt, tan lace top thigh hi’s, black patent heels, tight red sweater with breast forms. When I went to pick her up for the party she was not happy. Her roommates comments where “I think someone is trying to tell us something” I finally talked her into going. I passed 100% till I laughed and got outed. One woman walked up to us and said “honey that is not your first time in heels , you are better in them than most girls. That was the last straw. She left the party and ended up breaking up with me the next day P.S. Always looking for fun roleplay to expand my exotic writing.
sarasobad's Chat & Dating Profile
Watertown, New York, US
I am so confused about who I really am. It seems like I have been acting like a guy all my life but deep down I wish I would have been born a girl. When I was in elementary school there was a girl who was in a dress and tights and I wanted to know why I couldn't wear a dress. I soon tried on my mother's pantyhose and shoes and loved it. One day she caught me and screamed at me and I have been hiding it even since. I have finally come to understand I was born to be a woman and can no longer fight the feelings I have kept bottled up for so long.
Flyguyny1's Chat & Dating Profile
Floral Park, New York, US
Nice guy looking for a nice full time woman
MelissaP's Chat & Dating Profile
Schenectady, New York, US
I am Melissa Elisabeth Powers. I am a cross dresser..... most likely transgender. Some of my friends call me Missy. I spend as much time as possible as Melissa. When i was a teen, it was mostly for sexual gratification. As I have gotten older, this is who I really am. My mind, my heart and my soul are all female. Dressing and presenting as Melissa causes a lot of problems with my spouse. But, it just feels so right. I deal with demons in my head every day..... Therapy a point..... I am a skirt or dress girl mostly. Heels are a must. Some of my favorite songs are: "Melissa" by the Allman Brothers, "Lola" by the Kinks, "Take a Walk on the Wild Side" by Lou Reed, "I Know What Boys Like" by The Waitresses, "Dude Looks Like a Lady" by Aerosmith, "Looking for a Smart Woman in a Real Short Skirt" by Jimmy Buffett, "Touch of Gray" by The Grateful Dead, "Paradise by the Dashboard Light" by Meatloaf, "What a Wonderful World" by Louis Armstrong, "Somewhere Over the Rainbow" by various artists, "Man! I Feel Like a Woman" by Shania Twain, "Short Skirt/Long Jacket" by Cake, "Put My High Heels On" by Robin Meade, "Bubbly" by Colbie Caillat, "The Weight" by The Band, "Something to Talk About" by Bonnie Raitt, "Legs" by ZZ Top, "Suicide is Painless" by Johnny Mandel, "Unwell" by Matchbox 20, "Paint It Black" by the Rolling Stones,
jroddy's Chat & Dating Profile
Canton, New York, US
bigenner drummer long wave hair cleaven heavy metal metal my favorite bands kiss metallica megdeh judas megdeth metallica judas priest tool biggener drummer just learing to play my drums seeking a real true lover for who i am for being me for my heart and soul who likes to cduddle
SheilaWNYC39's Chat & Dating Profile
New York, New York, US
Mature long time crossdresser interested in mature men
mxtiffanyleigh's Chat & Dating Profile
New York, New York, US
I'm genderqueer and live in New York City. UPDATE: on Saturday, October 22, 2022 I am hosting a one-night only GORGEOUS: Triangles Cafe Reunion party in Danbury, CT at the original location of the former Triangles. Based on the RSVP list it's going to be an epic turnout! For more info check out my latest blog entry here for details and the official flyer. Event links can also be found on FB, FetLife, the non-adult URNA forum, and here = I'm a "charter" member of the URNA community. [If you remember Friends Landing in Haverhill, MA then you have a clue as to how long!] URNA was an important influence in my life when I first came out and helped me discover and understand my queerness and trans-self. For 12+ years I hosted and organized 100+ monthly TG parties at Triangles Cafe in Danbury, CT. These legendary events were beloved by our community until Triangles closed its doors in 2015. It was considered "Studio 54 for the URNA community" and I'll always be proud of them. For a few years after that I hosted GORGEOUS at Trevi Lounge (Fairfield, CT). I'm less active on URNA but you can always find me on Twitter, Insta, FB, or FetLife below.
kimginth's Chat & Dating Profile
Buffalo, New York, US
long time crossdresser been doing it for decades just starting to come out of the closet.looking for like minded friends and support .especially ones from western ny.
jvalj's Chat & Dating Profile
New York, New York, US
I am a mature guy who is looking to meet and get to know transgendereds, cds, and tvs. I just find I am drawn to a lovely t-woman and would love to have a very special friend.
JenniferWoods's Chat & Dating Profile
New York, New York, US
I'm a long time member here dating back to the 20th Century lol and have made so many friends over the years but none I love more than my current group (you know who you are). I've been dressing my whole life, it is part of who I am and wouldn't want it any other way. Please say hello in chat or drop me a line sometime. I love normal day to day chat so if you're looking for cyber or sex chat please move on.
jerrie585's Chat & Dating Profile
Elmira, New York, US
I am a mature crossdresser who waited way too long to come out of her closet. the older we get, the more we realize how short, and precious our time on earth really is. so, do the things that make you happy, and do them now! I do have other interests, but one of the things that does make me happy is dressing up, and getting out on the town, and doing fem things with someone else who shares my same interest in being feminine. I recently moved from my home state, and because of distance, I have lost contact with my old circle of girlfriends. I would very much like to establish new relationships and meet new friends in my local area. I am intelligent, easy going, in pretty good shape, and try to be drama free. it would be nice to meet someone local with the same outlook and attributes. my interests include woodworking, and anything in the wild outdoors. ie:) hiking, fly fishing, rowing my raft in whitewater, kayaking, canoe tripping, cross country skiing. you get the idea!
Jessica7471000's Chat & Dating Profile
New York, New York, US
I'm transition ...hrt 1 yr now
TonySyr's Chat & Dating Profile
Syracuse, New York, US
Nice guy in central NY mostly here to chat with friends. Feel free to say Hi.
SherylCD's Chat & Dating Profile
White Plains, New York, US
I'm a mature closeted CD with no real life experience. I luv to dress pretty and explore my femininity as often as I can. I'm embracing the gurl within because I can no longer deny my feminine feelings. They are real and getting stronger all the time. The gurl within seems to be taking control. I enjoy being her. Much more into the mental aspects of this than the physical. The gurl within seems to be taking control and I accept that. I'm a shy passive gurl, a bit of a wallflower. If you like my profile, please feel free to chat me up. I am very much into the psychological aspects of being a gurl. I don't dress to feel feminine, I feel feminine, so I dress appropriately. I recently went shopping as Sheryl at a friendly store. Being fitted for clothes was really quite exhilarating. I love to become Sheryl when I can, transforming myself into the woman I enjoy being. When I am Sheryl, I find myself relaxed and happy. Getting dressed and made-up is a great sensation for me. Just putting on all the feminine lingerie, the stockings and the high heels is so wonderful. Applying my make-up and seeing Sheryl reflected in the mirror is quite exciting. Adding my jewelry to be even more feminine, allows me to express myself and be who I like to be. I'm a work in progress. Thank you for reading my profile.
samdaman's Chat & Dating Profile
Buffalo, New York, US
New to all this and am interested in who is out there to learn more.
Andrea's Chat & Dating Profile
New York, US
Trans woman in NY just checking things out. Usually in the chat when I’m online, so definitely a better option to reach me than sending mail, and if we’ve spoken let me know you’ve sent a friend request. Theres way too many notifications from randoms so I’ve just stopped checking mail and friend requests. And please for the love of god no incels.
MichelleRNYC's Chat & Dating Profile
New York, New York, US
Hi I am a life Long Crossdresser. since the age of 12. I have been out at clubs I have had relations with other CD guy and Transwoman and Trans men. I am easy going with a good sense of humor.
CarinaFrancesca's Chat & Dating Profile
New York, New York, US
Uninhibited FT/TG Lady looking for fun. Maybe more. Sorry not interested in men Proud Owner of MY Collared Dick sucking Ass Plugged Cock Whore Sissygirl :-) Such a Depraved Hopeless Helpless Sissy Slut. Would raise Messalina’s eyebrows :-)
AshleyWiskers's Chat & Dating Profile
New York, US
Love to have pervy chat with like-minded people. Love to share pics and fantasies. Into cock bondage, femdom, forced milking, sissification, etc.
Brian1988's Chat & Dating Profile
New York, New York, US
Ask and you\'ll know a lot about me. Romantic, sweet man looking for a cute T-Girl. I don't have a profile photo because I seriously hate the way I look.
JimNYC's Chat & Dating Profile
Brooklyn, New York, US
Hi I'm Jim from New York I"m 57 5'8 170 brown hair blue eyes, a very nice and sincere intelligent person. I current work for a advertising company in there legal department. I like all kinds of sports, like to read, do bowl a few times a week. Interested in forming a nice friendship/relationship hopefully leading into more with an intelligent person. If that's you if were in chat please send a message or email me, so we can get to know each other better. I hope to hear from you soon!!!

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