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Chat with shemales, transsexuals and ladyboys from Maryland 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 Maryland. Click the "Enter Chat Rooms" button to create a free shemale chat profile and start chatting now. Not from Maryland? All transgender chat profiles are easily searchable no matter where you are. With 31 chatting in the shemale chat rooms and with 364 ladyboy community members online you are sure to find fun transsexual friends to chat with. Join us in the free shemale Maryland chat rooms and start connecting.

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Shemale Chatters in Maryland

Dagonknightx's Chat & Dating Profile
Hagerstown, Maryland, US
So it's long past time that I actually wrote something on here worth looking at. For starters, my name is Tim and it's a pleasure to meet all of you. I'm a bi male whose interests vary. While I went to school for art and learned much there, life has a tendency of sending you in directions you never expected to go. I still do free lance work, both graphic design and fine art, but I work a regular job now. I'm trying to get back to my roots, meet new people and see what the world has to offer. As far as what I'm looking for, I'm looking for friendship, fun and possibly more. I love stores and creating new ones. The world is full of new adventures and I plan on living as many as I possibly can, both in cyber space and the real world. Feel free to pm me and just say hi. I only bite once I know you.
mary20603's Chat & Dating Profile
Maryland, US
I am a mature full figured crossdresser who enjoys role play fun! I love anything from romance to humiliation and embarrassment play. I dress completely as a prim and proper lady but with a hint of sexiness. Pm with a scene and lets play
Robynne's Chat & Dating Profile
Hagerstown, Maryland, US
I am a CD who likes wearing short, provacative skirts and tight nylon underwear. I am bi-curious and love intimate settings. However, while I enjoy dressing I am not passable unfortunately.
JimL's Chat & Dating Profile
Maryland Line, Maryland, US
Admirer from Maryland
Joanne's Chat & Dating Profile
Maryland, US
I like to dress and meet others. Enjoy going out and having fun. Like most kinds of music. Meet nice people. Accept people for who they are. Dont judge anyone. I have met some wonderful people here. Thanks URNOTALONE
Patty50's Chat & Dating Profile
Annapolis, Maryland, US
I love to CD!! Miniskirt, hose, heel are so exciting to wear.
rachelc's Chat & Dating Profile
Ellicott City, Maryland, US
I am a cross dresser that is slowing coming from the closet. This has been a long process but I recognize that Rachel is who I am and that continued denial just creates unhappiness, i.e. I am happy as Rachel. After much soul searching and knowing that individuals like and need labels, I feel the best label and description of me is "submissive sissy". I am seeking a domestic partner willing to accept and embrace me as Rachel. I would prefer a Dominant Gurl or Male. I am submissive and do not wish to be anything that I am not. Please message me if you are open to a Domestic Discipline relationship and will respect that I am truly and only Rachel. This has been quite a journey and I look forward to each of the tomorrows. Being here and chatting and feeling the support has meant the world to me. Thank you all! xoxoxo
NicoleFemme's Chat & Dating Profile
Maryland Line, Maryland, US
i am a tall, sexy tgurl who has been feminizing for four years. I would love to meet other gurls, crossdressers, and men who know how to treat a shemale.
Jennjoe's Chat & Dating Profile
Maryland, US
We are a couple looking for bdsm
DCGuy4Girl's Chat & Dating Profile
Waldorf, Maryland, US
I have never been good at this part. I've been a long time fan of trans girls. I like to think I am friendly, so feel free to say hi. My personal life is complicated, to say the least. I've made my share of mistakes there as well. But I think quite a few of us are in that spot on this site. Say hi to learn more about me.
Bgreen's Chat & Dating Profile
Baltimore, Maryland, US
Kool laid back funny
Girleanna's Chat & Dating Profile
Gaithersburg, Maryland, US
Petite CD seeking romance with a mature, caring man. I’m part-time and only occasionally available. 5’7”, smooth all over, very feminine and comfortable passing in public. I’ve dated lots of men over the years but still looking for that one special guy to sweep me off my feet! Please be a good conversationalist and have a nice smile … that goes a long way with me! I’m an avid hiker and enjoy the outdoors. I love animals (especially my adorable 2-year old pit bull), enjoy all kinds of music, good restaurants, museums, the theater, and I love to read. I’m not super picky or fussy …. but I have high standards when it comes to the people I enjoy spending time with! I value confidence, honesty, and decency. Tall men (I like to look up when being kissed!) who practice good hygiene, can make me laugh, and who are comfortable being in public with a CD will get my attention. I seek a relationship based on comfort, passion and mutual respect, without any pressure or expectations. If you can imagine spending time in the company of a natural T-girl who treats you like a real man, and who cherishes being treated as a real woman, then maybe we can chat and test our chemistry!
Behindenemylines's Chat & Dating Profile
Baltimore, Maryland, US
I joined this site a while ago but recently returned- looking for a special friend.
Jaycum97's Chat & Dating Profile
Marydel, Maryland, US
Looking for something real
Colobuff55's Chat & Dating Profile
Glen Burnie, Maryland, US
Interested on meeting new friends.
Bulld156's Chat & Dating Profile
Baltimore, Maryland, US
Good looking honest person respectful
Hendricks276's Chat & Dating Profile
Baltimore, Maryland, US
Hello I'm John look to chat
crazyhorse's Chat & Dating Profile
Pasadena, Maryland, US
looking for sex , need uncomplicated situation
asiantopmd's Chat & Dating Profile
Looking to have some fun.
sionbase's Chat & Dating Profile
Essex, Maryland, US
55 black fun love male

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