MenuClose Menu

Adult Transgender Ontario, Canada Chat Rooms

31 Chatting Right Now!

Enter The Free Adult Transgender Chat Rooms!
31 Chatting - 350 Online

Chat with transgender women, transsexuals and ladyboys from Ontario, Canada in our free adult trans, ladyboy and transsexual chat rooms. We strive to be totally inclusive. We welcome transgender women, 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 Ontario, Canada. Click the "Enter Chat Rooms" button to create a free chat profile and start chatting now. Not from Ontario, Canada? All transgender chat profiles are easily searchable no matter where you are. With 31 chatting in the chat rooms and with 350 ladyboy community members online you are sure to find fun transsexual friends to chat with. Join us in the free Adult Trans Ontario, Canada chat rooms and start connecting.

Popular Nearby Cities: Barrie, Toronto, Ottawa

Explore More Of Canada: Alberta, British Columbia, Manitoba, New Brunswick, Newfoundland and Labrador, Newfoundland Labrador, Northwest Territories, Nova Scotia, Ontario, Prince Edward Island, Quebec, Saskatchewan, Yukon

Adult Transgender Chatters in Ontario, Canada

Michelle2112's Chat & Dating Profile
Toronto, Ontario, CA
Hey, so I'm a pre-op transwoman living full time since 01/2020 looking to connect with people. I am independent and consider myself to be an ardent feminist. I'm typically a bit reserved out of the gate, but that can change depending on how comfortable I feel around someone. I tend to see myself as: analytical and kind of artsy, love technology, love movies in general (I guess most people would say loving 'film' or 'cinema' is too pretentious!), gritty Netflix and Anime series, music is an integral part of who I am, and I love having conversations about anything from the mundane to politics. I don't eat meat but love all sorts of food. Indian food is my absolute favourite but am always interested in other styles... I'm a huge hockey fan and just love Sid. As I get older I find that I seek connections with people that are more meaningful and interesting, be they friendships or something of a more romantic nature. I find as the world around us seems to become a harsher place that we need to be kinder - to others AND to ourselves. I mostly don't mind if folks PM me and it would be great if you were polite!
cindifemme's Chat & Dating Profile
Toronto, Ontario, CA
I considermyself very feminine.Please ask and I will tell you.
hayleecdgurl's Chat & Dating Profile
Toronto, Ontario, CA
Just a shy cross dresser
sybarite's Chat & Dating Profile
Toronto, Ontario, CA
I enjoy spending an evening with an intelligent and enchanting woman as we share a bottle of vino while the dulcet sounds of bossa nova waft across a dimly lit room.
Curiosity6960's Chat & Dating Profile
Cornwall, Ontario, CA
I want you to do whatever you want to me
mayatoronto's Chat & Dating Profile
Toronto, Ontario, CA
Hi everyone. I am a 45 year old crossdresser living in Toronto. I am 5'7, smooth and slim. I have been crossdressing since an early age, but I am very part-time. I dress maybe once or twice a month or so and am considered passable. My favourite thing is to be out in public fully dressed as a woman and to be called "miss" or "ma'am", having the door held open for me by men. I also love dressing up as a secretary! I'm looking to chat with anyone about this need to dress and act like a woman. Check out my flickr page at
Melissa65's Chat & Dating Profile
Toronto, Ontario, CA
Life long cd looking for new like minded friends
Crisiecd1's Chat & Dating Profile
Toronto, Ontario, CA
Mature CD likes to chat with other mature cds
Quietcityguy23's Chat & Dating Profile
Toronto, Ontario, CA
Just looking to meet open minded people, anything else feel free to ask.
JeniferSands's Chat & Dating Profile
Whitby, Ontario, CA
Hi, my name is Jenifer. I am so glad to be part of this site. Hoping to meet some new friends and then who knows what could happen!! A little about me...........I have been dressing since about the age of 13. No one knows about Jenifer. I am a submissive girl who has a deep fetish for highheels, feet and sexy polished toenails. My email is
Giselle's Chat & Dating Profile
Oshawa, Ontario, CA
soon to be 67 yr old non op ts/ crossdresser with a somewhat tolerant wife
CateRedgrave's Chat & Dating Profile
Ottawa, Ontario, CA
Not much to tell... ask if you are interested?? no men please (sorry guys) I think the above still stands... but I'll tell a bit more... I'm married, yes she knows, and supports up to a point (a very fair point, no complaints at this end)... There is a a duality to lives like ours - cds, non-binary, gender fluid, etc., if you feel like duality applies to you, then so be it - sometimes it's a joy and sometimes it'll tie your knickers right in a knot! lol... The older I get there is more joy, and as much as I'd like to say there's less knots, let's just say that after years of practice, there's not a set of Christmas tree lights, or any kind of undies that can't get unknotted by the kind of experience that comes with the onset of grey hairs and laugh lines... Being in a committed relationship definitely precludes any kind of real life sexy shenanigans, but that doesn't mean that a sweet chat with the right person isn't off the table... BUT! please don't just sidle on up with a "he, he... I'm bored" or dive straight in to gettin' yer sexy on... time is valuable, like to spend it with likeminded people... the thing that turns me on the most, and I truly mean both platonically and on the sexier sides of things, is connection, and relatability... and sweetness, sweet people are the best... And for the gents, if you read this far... 'no men' isn't aimed at all men, you gotta understand that there's an unfortunate number of not-so-sweet dudes that wreck it for the gentlemen... I certainly don't mind chatting with the true gents... A wish for everyone, be well, have fun, smile, laugh... life is too short for anything else...
mikey9's Chat & Dating Profile
Peterborough, Ontario, CA
likes to enjoy everything in life. always open and curious
jocan's Chat & Dating Profile
Kingston, Ontario, CA
Hi back on here after taking some time off still figuring myself
Sissydanieller's Chat & Dating Profile
Toronto, Ontario, CA
I’m a sissy slave dm is open
Dcboi130's Chat & Dating Profile
Toronto, Ontario, CA
I’m 18 and I’m horny af and I’m a sissy trans
Wills's Chat & Dating Profile
Toronto, Ontario, CA
I am About Me An admirer of beautiful people. m an admirer of beautiful people inside and out. 'Try'sexual 50 m Canada top, masculine and fit. Am really here largely to make friends: regardless of gender. Love intelligent conversation and cyber can be fun. I'm definitely a top. I love subs 20 - 40ish, (absolutely no one less than 20 please). Nature has played a bit of a dirty trick on slim young guys they have evolved to perfectly take cock. Not surprisingly I love women, sissies, babes, emo, goth, barbies and yet love natural and fresh, too. Gender is just too arbitrary to concern myself with. In public, I strive to be a gentleman. In private, what happens is up to consenting adults. Been listening to the Syn Thetic podcast lately. Anyone else?
jennyt63's Chat & Dating Profile
Orillia, Ontario, CA
A crossdressing gurl looking to learn more from others as I go down this path. Interested in meeting like gurls, sissies, and into dom men. My journey has led me to meetings with other gurls for dress up days and I have now crossed that line of being with a guy, which I really enjoyed. I am definitely a submissive but will play with other gurls for fun but will be more on the sub side. I do cam with certain people, but my rule is we both need to be on cam or at very least have developed a trusting relationship while chatting. Like to dress as often as possible and looking to the day I go out in public, looking for a friends to enjoy this journey I have been on for a very long time. I am devoted to my wife who knows about my dressing but doesn't participate or support the notion of me dressing, so I keep it very private and away from her. Ideally I would like to find a guy who I can meet up with on a regular basis and be able to be Jenny with him. I would say the same for other sissy gurls as well, being able to meet and just be ourselves would be stimulating.
Dom1996's Chat & Dating Profile
Hamilton, Ontario, CA
Bicurious male looking to explore my sexuality with someone I connect with
Lisahhh's Chat & Dating Profile
Greater Sudbury, Ontario, CA
Im lisa....still pvt n discreet
Chbbylvr24's Chat & Dating Profile
Toronto, Ontario, CA
Love wearing dresses, lingerie, bra and panties. Not passable either. Looking for someone to dress with and see where it goes from there.
Roosterman's Chat & Dating Profile
Barrie, Ontario, CA
I'm looking for fun and more fun

Find More Adult Transgender Chatters In Ontario, Canada

© 2012-2022