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Chat with shemales, transsexuals and ladyboys from Massachusetts 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 Massachusetts. Click the "Enter Chat Rooms" button to create a free shemale chat profile and start chatting now. Not from Massachusetts? All transgender chat profiles are easily searchable no matter where you are. With 12 chatting in the shemale chat rooms and with 362 ladyboy community members online you are sure to find fun transsexual friends to chat with. Join us in the free shemale Massachusetts chat rooms and start connecting.

Popular Nearby Cities: Boston, Worcester

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Shemale Chatters in Massachusetts

JimX's Chat & Dating Profile
Middleboro, Massachusetts, US
Divorced (Finally!!) 50 something guy who enjoys the company of women, trans, crossdressers. And friends. Ive been coming here a long time and met great people. I enjoy going out on dates, dinner, movies, drinks. I like to be outside, beach and sun. I like to keep in shape but not a fitness nut. Old movies and tv and 40s, 50s and 60s music I enjoy as well.
Md1985's Chat & Dating Profile
Boston, Massachusetts, US
36 and very into tg and cds
HandsomeAdmirer's Chat & Dating Profile
Boston, Massachusetts, US
Seeking to make friends and find a nice girl to chat and see what happens
Becalove's Chat & Dating Profile
Auburn, Massachusetts, US
tall and lovin it, i guess there is a place for a 6' 3” girl in flats, as if i'd wear them. thanks for all the support. Just got back into my true self and always looking for new friends to enjoy this passion of us girls
jeffboston's Chat & Dating Profile
Andover, Massachusetts, US
Looking for that connection someone to chat with and maybe more. Love the outdoors and sports...
PaigeD's Chat & Dating Profile
Boston, Massachusetts, US
Hey all my friends! Like all of us I go in and out of dealing with my trans issues. I've always been weird and I've expressed that through my art. My gender expression to me is just an extension of my duel personality. I'm pretty well aware that I would make an attractive woman if I ever went full time. Truthfully that is kind of scary to me. If you like sci fi, comic books, art,... Let's chat/ hang out. I have to say that I am looking for friends WITHOUT benefits.
Brianna123's Chat & Dating Profile
Hingham, Massachusetts, US
Hi! I am a 46 year old working in Boston and living on the South Shore. I am looking to meet nice people for friendship and more. I joined as an admirer a long time ago, but realized this year that I enjoy dressing even more! I have been exploring CDing since and absolutely love it. It would be great to meet similar gurls and even some admirers!
lora's Chat & Dating Profile
Massachusetts, US
Hi everyone! Welcome, and thx for stopping by...I've got some new pix, so I thought it might be good to update the profile too. I've been dropping in to chat much more frequently lately and I gotta say it's been more ways than one...I just want to thank everyone who has been nice enough to chat, and tell you how much it helps... I'm really eager to get out of the house and mix and mingle, as I've never had the guts to get out of the house, but with the help of all the fantastic gurls I've been chatting with, I'm feeling stronger! So if you have some good advice on where a gurl like me might go and feel at home, please feel free to drop me a comment. One more thing, I'm particularly interested in meeting other tall gurls like myself, just so we can comiserate, and swap tips and stories... As far back as I can remember I've had the urge to dress, starting with a dream involving me in a purple ice skating dress. But I don't ice skate....hmm. I am looking for TG and TGfriendly people to hang out with and help me get the courage (and the accessories!) to go out en femme with for the first time. I tend toward fetishy-pinup (stockings, garters, high heels, corsets etc.) clothes, but I'll wear anything that makes me look good! I'm a very tall girl (6'2" but not afraid of 5" heels (6'7"!!). En drabbe, I'm married (SO knows)w/kids and I enjoy a performer (guitarist/singer/songwriter), and as an audience member. Also enjoy....a good glass of wine...or another one, what the hell! and am a lifelong member of the 420 club. I'm not looking for sex partners...just fun, kind friends.
EdwinaBoston's Chat & Dating Profile
Weymouth, Massachusetts, US
I'm a married & sane life long dressing CDer. I'm honest, friendly & have a good sense of humor. I'm 5' 8" and try and keep myself in good shape. Goodness knows it isn't easy keeping fit! I enjoy dancing when I'm able to get out. My wife knows all about my dressing but doesn't participate. I get out to CD/TG/TS events occasionally (First Event, local New England parties) and always enjoy hanging with cool, fun people. Not into cyber at all. Peace and hug! Em
TheAmericanGirl's Chat & Dating Profile
Boston, Massachusetts, US
Hi Everybody Returning member here Thank You Pamela for the invitation
tallbob's Chat & Dating Profile
Boston, Massachusetts, US
just a tall man looking for friends , chat , and all that . Not into men ,
dsavvvvvv's Chat & Dating Profile
Boston, Massachusetts, US
Want to try something new!
Demanda's Chat & Dating Profile
Allston, Massachusetts, US
Hello, I'm a passable part time girl in Boston looking for other girls like me and real girls to make frineds and hang out,nice guys are welcome to say hi, please show respect. thank you
bostoncdmichele's Chat & Dating Profile
Boston, Massachusetts, US
boston area M to F cd luv getting out dressed and meeting other girls
Marli's Chat & Dating Profile
West Boylston, Massachusetts, US
Hi, Looking for friends in New England and beyond!!! Finally getting "out"!!! very exciting! Would love to meet some girls and make some new friends!!! xoxx Marli
BostonGina's Chat & Dating Profile
Natick, Massachusetts, US
I'm a single 45 yo CD from the Boston area. Been dressing about 5 years. Looking to meet fun and friendly people.
PattiAnne's Chat & Dating Profile
Pepperell, Massachusetts, US
Closet Cd from Massachusetts. Looking to meet new friends.
Demi's Chat & Dating Profile
Boston, Massachusetts, US
.Gracefully aging long time CD ...Same story as most here..Starting young etc. Love : music, classic cars, motorcycles, the great outdoors and dressing of course !!!!Enjoy talking with others like myself and would love to get together with other girls this year and explore our gift.Love Dressing, shopping and Pic play !!Any "girl" musicians looking to jam ? Thanks SO much for support, your all wonderful. !!! NOT interested in men !! AGAIN NO MEN !!!NO MEN, NO MEN !!!!Got out more this year. Hope to even more in 2022
JocelynCD's Chat & Dating Profile
West Springfield, Massachusetts, US
I love femininity and try to be stylish and age appropriate. I was about 11 when I slipped on my mom's bra and it's been quite a journey since then! I've done things and been places that only some very random set of people will ever know about, and sometimes even I can't believe where I've been and what being a crossdresser has introduced into my life. Mostly I love it but sometimes I wish I didn't have this part of me...but what's a girl to do? :P
francineSissy's Chat & Dating Profile
Boston, Massachusetts, US
I am a submissive sissy who likes to role play with respectful men, women and tg’s
tanya1's Chat & Dating Profile
Auburn, Massachusetts, US
been dressing now for about 10 years, wife never approved but could never get the urge to stop. looking to chat with other cd's and tg's and men. Don't ask for pictures don't have any yet. If you are at work please do not instant messages me and please if u are under 30 I will not respond to your messages. nothing personal ,just my preference.
Deana's Chat & Dating Profile
Watertown, Massachusetts, US
I have been crossdressing for as long as I can remember ! I love nylons, short skirts, dresses, heels, and lingerie. Sincere & Discrete! ! Love to Crossdress & Admire to KEEP PRETTY & STAY SAFE ! Dee E-Mail Address is
johnny5's Chat & Dating Profile
Dedham, Massachusetts, US
Hello. I'm here to make friends, share conversation, fun and who knows. I'm a bit shy to start but down to earth and pretty easy to talk to. Feel free to say hi, ask away and converse. Not into cyber. Prefer good conversation, fun, flirting. Would like to connect with someone and see what comes of it. Best regards.
RichPrrn's Chat & Dating Profile
Lowell, Massachusetts, US
I am looking for someone who is exciting and different

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