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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 57 chatting in the shemale chat rooms and with 436 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

Deana's Chat & Dating Profile
Boston, Massachusetts, US
My male self still holds doors for women and stands when one walks into the room!! I like putting on women's things, but I never really thought of it as crossdressing because that was "wrong". But I really do like it. I know now that what I like to put on are silky pretty feminine things. Love pantyhose, short skirts, dresses, and lingerie so much ! Sincere & Discrete! ! Love to Admire too ! KEEP PRETTY ! Dee E-Mail Address is
tanya3's Chat & Dating Profile
Boston, Massachusetts, US
after a short time away decided to come back and see old friends. If u are under 30, please do not pvt message me, personal preference, if u are at work please do not as well. i do not care for long gaps of silence while u work and I wait. gf with vixx, if she is in I am busy. I have been cross dressing for about 10 yrs now. still haven't come out but hopefully in time i will. With the suppport of friends in here it has help calm the nerves especially patty who has been there through thick and thin as well
Michaela200's Chat & Dating Profile
Franklin, Massachusetts, US
MWCD looking for friends to help me learn more about CDing Looking for other CDs only - no men please tall and average build Still not out yet.... Looking for friends to email and possibly meet/chat with
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 Flamboyant xoxo God speed ........ if you can't chat and share pictures here then we dont chat ! Lol hahaha wtf ? don't be sendn redirecting emails n websites helloooooo
Patsman's Chat & Dating Profile
Boston, Massachusetts, US
Looking to make new friends, divorced a few years ago. When younger always attracted to crossdressing, flirted with it, but never went all in. I'll admit, I think those of you who take that journey have alot of courage in being true to who you are. I'm not really on this site to find romance, but I will admit that I am attracted to M2F, and hope maybe someday could enjoy a date with the right woman. I enjoy the chatting and PMs on this site. I think I'm a nice guy, but don't ask my ex. We divorced after 25 years. Stayed together for my kids, who I love with all my heart, but I regret those lost years without really loving someone. Reach out, be positive, say Hi. Best
jillians's Chat & Dating Profile
Boston, Massachusetts, US
Start slow. Try and connect. Make love.
stocky88's Chat & Dating Profile
Boston, Massachusetts, US
I’m young attractive chill
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!!
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.
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
Bigpapi99999's Chat & Dating Profile
Peabody, Massachusetts, US
Your AccountBigpapi9889Account ?MailLists ? Bigpapi9889 Online Edit ProfileEdit Settings ProfilePublic Photos 0Private Photos 0Galleries 0Blog 0Friends 1 The Essentials Last Seen: OnlineJoined: Nov 28, 2023Age: 32Gender: MaleLocation: Boston, MA, USRelationship Status: SingleInterested In: T(M2F)HIV Status: NegativeHeight: 6 ft. 2 in. /187.96 cm.Weight: 200 lbs.Race/Ethnicity: White About Me First off I was having an amazing chat with a beautiful trans woman and we were close in age and she is everything I've ever wanted, but I lost my info when I accidentally logged out and made a new profile. Please reach out, you called me papi and you are 28 and love strict dominant guys that take care of you and protect you. Where are you??!!!I have so much respect for trans women, I am masculine, dominant and looking for a submissive bottom with a small cock. I'm 7 in thick cut clean disease free. Looking to meet my future hookup girl or more I want to chat and see where things lead and meet!
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.
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.
nataliesheer2's Chat & Dating Profile
Boston, Massachusetts, US
Very Feminine.Looking for friends
Jwilson's Chat & Dating Profile
Boston, Massachusetts, US
Looking for vid chat fun
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.
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
KassyBoston's Chat & Dating Profile
Boston, Massachusetts, US
Hi I hate talking about myself but I'll try, I'm just a Bi Sub CD that has been dressing off and on since 12yrs old, just got into it out of curiosity and never stopped. I know I'll never give it up. I love the feminine feeling of dressing as a woman and all that comes with it. I especially love other girls like myself.
Bigpapi9899's Chat & Dating Profile
Peabody, Massachusetts, US
I'm a 30 year old male. Clean, drug and disease free. Hygiene is very important to me. I'm 6 foot 2 in, 200 lbs and have a 7 in cut cock. I'm looking to chat and meet a beautiful non op transwoman. I love sucking cock and getting sucked but I sure do love to have sex with a trans woman!
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.
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
Geeker's Chat & Dating Profile
Framingham, Massachusetts, US
Want to try something new I love metal and video games and cars. I love to shredd geetar!
tallbob's Chat & Dating Profile
Boston, Massachusetts, US
just a tall man looking for friends , chat , and all that . Not into men ,

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