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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 46 chatting in the shemale chat rooms and with 400 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

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
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. I do have a special friend that wears a collar for me. I like to laugh but yet if you need someone to talk to i will be there to lend an ear. I am still trying to discover myself even after this long. Its a constant journey that I would like to share with others and have others share their journey with me.
bostoncdmichele's Chat & Dating Profile
Boston, Massachusetts, US
boston area M to F cd luv getting out dressed and meeting other 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...
DonnaCooper's Chat & Dating Profile
Norwood, Massachusetts, US
I have been a closet crossdresser since my mid teens when I guess I began really noticing the difference between males and females. I felt more comfortable in the company of women, and frequently did chores around the neighborhood to be closer to some of my older female neighbors. My first time completely transformed as a female happened when an impulse struck me to feel closer to the woman who hired me to babysit her very young children once or twice a week on regular basis. Although she was married, her husband was usually not around much of the time. One evening after the kids were settled in, I noticed her bikini hanging on a rack in the laundry room. The more I looked at it, the more I felt the need to see how it would look and feel on me. From that point, I was hooked, and I was quite fortunate in that I could fit into most of her outfits. She also had a few wigs, so I was always able to wear one of them when I transformed into her and saw the reflection in the mirror (at least in my mind, I felt I was more her than myself). My wife and family do not know about this side of me, and for most of my life I have dressed in complete secrecy. It is only the advent of the Web and forums such as this that have allowed me to talk about dressing with people that know how I feel. Unfortunately, I have purged far too many times, and have vowed to never purge again. I love classic styles and enjoy emulating the looks of what might be described as a successful business woman and mom.
JimX's Chat & Dating Profile
Middleboro, Massachusetts, US
59 year old (yikes!) 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.
BethanyinBoston's Chat & Dating Profile
Boston, Massachusetts, US
Hi, 28 y/o girl looking to meet people and see what happens :). Have a brain and hope you do as well :). Bethany
HandsomeAdmirer's Chat & Dating Profile
Boston, Massachusetts, US
Seeking to make friends and find a nice girl to chat and see what happens
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
nezzyapple's Chat & Dating Profile
Stoneham, Massachusetts, US
Hi I'm new to this would like to try I'm a bit shy also into a couple of fetishes if interested
tallbob's Chat & Dating Profile
Boston, Massachusetts, US
just a tall man looking for friends , chat , and all that . Not into men ,
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
BostonGina's Chat & Dating Profile
Auburn, Massachusetts, US
I'm a single 50yo girl from the Boston area. While I worked from home during Covid it gave me new opportunities. I’ve now been dressing full time since late 2021. Enjoying my new found freedom.
Cherylgirl's Chat & Dating Profile
Dartmouth, Massachusetts, US
I'm a life long crossdresser. I've been dressing since my teen years and enjoy all facets of the feminine life-style. Adore sexy dresses. bras, breast forms, garter belts, heels, hose and sexy lingerie. Love to get together with other like minded girls in SouthEast Massachusetts. Enjoy chatting with admires and other friendly girls to discuss fantasies, dressing, make-up, shopping, etc.
Md1985's Chat & Dating Profile
Boston, Massachusetts, US
36 and very into tg and cds
sophialegs0000's Chat & Dating Profile
Watertown, Massachusetts, US
Enjoy the feel of lingerie and high heels. Love the femininity of it all. Hoping to meet like-minded people and share interests.
LizBlissCD's Chat & Dating Profile
Boston, Massachusetts, US
Just enjoying being Liz!!
Deana's Chat & Dating Profile
Boston, Massachusetts, US
Love to Crossdress & Admire to I have been crossdressing for as long as I can remember ! I love nylons, short skirts, dresses, heels, and lingerie. Sincere & Discrete! ! KEEP PRETTY & STAY SAFE ! Dee E-Mail Address is
silktongue's Chat & Dating Profile
Boston, Massachusetts, US
Hmmm Where do I start, well I am a lover of and admirer of Trans gurls and crossdressers. I have been an admirer for many years, it goes back to when Jacques was open till 2am and it was well attended. I have attended parties in Wakefield and also a town in Kentucky. Also attended some dressing parties in hotels near Boston. Those were excellent and the gurls were very accomodating. I loved being amongst the gurls watching and participating in the activities. I especially loved it when the gurls wore silky negligees. I have been a lover of watching videos of dressers and shemales, some are very erotic. I have had a massage from a xdresser and loved it. Finding another that gives massages has been very difficult. For those of you that may read this profile I need you to know that unfortunately I am unable to perform like I once did. Oh I still get turned on and able to cum, but not able to penetrate. It sucks getting old. I would love to hear from anyone interested, especially if you are in the area. I will try and post some pictures soon.
BrendaTGgal's Chat & Dating Profile
Plainville, Massachusetts, US
Hi. I'm Trans, but not transitioned. Been out for years...go out to parties, events...or just socializing and shopping. Always looking yo meet new friends. Do have a submissive side like to explore.
TheAmericanGirl's Chat & Dating Profile
Boston, Massachusetts, US
Hi Everybody Returning member here Thank You Pamela for the invitation
JennMA's Chat & Dating Profile
Marlborough, Massachusetts, US
early 50s, athletic part time crossdresser who doesnt get out as much as id like...working on makeup and being more feminine. hoping to connect with other gals or admirers.
Babygirl's Chat & Dating Profile
Grafton, Massachusetts, US
I am a nice. Guy looking. For. Some. Fun

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