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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 37 chatting in the shemale chat rooms and with 395 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.

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Shemale Chatters in Massachusetts

JimS's Chat & Dating Profile
Middleborough, 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. My flickr. If we are flickr friends more to see.
silktongue's Chat & Dating Profile
Boston, Massachusetts, US
Ok so here I am, I have tried to be as open as possible about myself. But someone always has more questions, so feel free to ask. I enjoy being visually stimulated among other ways. So hopefully you enjoy wearing sexy things and aren't afraid of showing me. I promise, I won't bite, unless of course.................. I enjoy chatting and hopefully you will respond if I say Hello. 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. I would love to hear from anyone interested, especially if you are in the area. I will try and post some pictures soon.
tanya2's Chat & Dating Profile
Auburn, Massachusetts, US
If u are under 30, please do not message me. If you are at work, please do not message me. No men. Please don't send a friend request if i dont know you. It will be declined. I have been dressing on and off for 10yrs. I have been dealing with these feelings for longer. It has been a journey that I am still on. Trying to figure out who I am. I have figured out though where I belong. I have a special daddy helping me with my journey. Thank you daddy.
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.
SaraD's Chat & Dating Profile
Winchester, Massachusetts, US
I just adore all things fem, passion continues to grow as i spend more time as Sara. Luv to shop, especially shoes and fine lingerie and hosiery. My shoes collection is now over 50 pairs!!
TheAmericanGirl's Chat & Dating Profile
Boston, Massachusetts, US
Hi Everybody Returning member here Thank You Pamela for the invitation
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
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 !!Enjoy getting out and enjoyAny "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 2023
tallbob's Chat & Dating Profile
Boston, Massachusetts, US
just a tall man looking for friends , chat , and all that . Not into men ,
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.
nataliesheer1's Chat & Dating Profile
Boston, Massachusetts, US
I am very feminine.Lets chat and I will tell you everything. Looking for friends.
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 pantyhose, short skirts, dresses, heels, and lingerie. Sincere & Discrete! ! KEEP PRETTY ! Dee E-Mail Address is
Boston1's Chat & Dating Profile
Taunton, Massachusetts, US
White m 508 Massachusetts , interested in the exquisite m to female ts, for chat! Location is a plus but not a must! I'm a Leo and a Virgo on the cusp! I'm a lover and a fighter xoxo God speed
AlphaMale617's Chat & Dating Profile
Boston, Massachusetts, US
mwm 67 years old 5'10" 235lbs masculine and muscular buy, do have a belly, not a jelly belly.. lol , Alpha Dom Male for sure, seeking a submissive cd/tv who dresses fully and not afraid to meet. The weaker the better, can never be too fem for me. Yes, I am kinky, well maybe just a touch, but you never know unless you try.
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
DeeAnne's Chat & Dating Profile
Boston, Massachusetts, US
Hello ladies, I am Dee anne, I have been on this site for a while and love it, I have learned a lot about myself. I love dressing in every thing from very glamorous to casual hang out outfits. I like to think I have improved in make up and hair styles but still mess up some times. I can not dress full time (unfortunately), wife knows some and is not supportive. I have discovered that I really enjoy being dressed and femme, almost like I am a different person. I would like to meet others who enjoy dressing, allowing a friendship to grow and I feel curious when dressed to be with another. I love going out shopping and stopping for a drink and meal, the times I have were great. You can contact me Dee_annecd@yahoo Thanks for reading Hope to hear form you! Dee anne
HandsomeAdmirer's Chat & Dating Profile
Boston, Massachusetts, US
Seeking to make friends and find a nice girl to chat and see what happens
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
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
Geeker's Chat & Dating Profile
Framingham, Massachusetts, US
Want to try something new I love metal and video games and cars.
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
bostoncdmichele's Chat & Dating Profile
Boston, Massachusetts, US
boston area M to F cd luv getting out dressed and meeting other girls
Tmgly's Chat & Dating Profile
Wakefield, Massachusetts, US
Always ready for fun safe times
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. Very sissy, very sub, very servile. Let be your sheplacement - let me cook and clean for you and help you unwind after a long day of work.

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