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Chat with shemales, transsexuals and ladyboys from Oregon 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 Oregon. Click the "Enter Chat Rooms" button to create a free shemale chat profile and start chatting now. Not from Oregon? All transgender chat profiles are easily searchable no matter where you are. With 37 chatting in the shemale chat rooms and with 392 ladyboy community members online you are sure to find fun transsexual friends to chat with. Join us in the free shemale Oregon chat rooms and start connecting.

Popular Nearby Cities: Eugene, Salem, Portland

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Shemale Chatters in Oregon

Maryanne222's Chat & Dating Profile
Portland, Oregon, US
Crossdresser, submissive bottom. I love strong Daddy types.
JosieFaeChild's Chat & Dating Profile
Dallas, Oregon, US
Trans Girl. Been a sissy since I was 12 but officially started transitioning a few months ago.
Bob97501's Chat & Dating Profile
Medford, Oregon, US
Im a gentleman from the old school--you treat a lady like a lady. Flowers on a date---and enjoy the look of a lady dressed feminine and as ladies used to. And the ladies here are more ladylike than most real ladies I have met.
TaraRenaeCd's Chat & Dating Profile
Medford, Oregon, US
Looking for ltr with older gentlemen NSA.
SirGalahad60's Chat & Dating Profile
Oregon, US
First things first. No picture, no chat. Warning to crossdressers, i really don't care what you're wearing. Long time member. Tired of the normal drama in the rooms. I'm just an old farmer from Oregon and I am looking for a true woman at heart. Tg or gg is really kind of irrelevant. I'm definitely an Alpha man. But not some asshole dom. If you're looking for pain or humiliation. I'm not your man. Their are damn few Trans women. The true ladies are worth protecting.
Indiscretionist's Chat & Dating Profile
Portland, Oregon, US
Closeted occasional crossdresser looking for likeminded friends to chat with, share stories with, and play with.
MarshaLou's Chat & Dating Profile
Pendleton, Oregon, US
I am a long time cder. I like classy clothes sexy lingerie and 4 or 5 inch heels. Love to dress and do so about 80% of the time. I am very fortunate to have a supportive spouse who enjoys Marsha too. I also enjoy fun chats with other girls . Pvt conversations welcome.
abc71090039's Chat & Dating Profile
Portland, Oregon, US
40s male interested in mtf
BigDan's Chat & Dating Profile
Portland, Oregon, US
Fit and endowed stud looking for fun
Smac45's Chat & Dating Profile
Portland, Oregon, US
Great guy who loves to dress up.
Laynah's Chat & Dating Profile
Ontario, Oregon, US
Interested in CD, TG, GG, and maybe others to chat and cam with.
wildroses's Chat & Dating Profile
Salem, Oregon, US
meet someone an explore
9999hotcocks's Chat & Dating Profile
Salem, Oregon, US
Like to wear panties tights girdles bras enjoy being submissive
boricuaman1969's Chat & Dating Profile
Beaverton, Oregon, US
I am a puertorrican male living in Beaverton, OR. I am an admirer looking to meet new people in my area and elsewhere. I have had several transgendered friends in the past when I lived in Florida so I do have a frame of reference to engage in discussions in an intelligent fashion. I enjoy the company of transgendered ladies and I am very open minded. I do not engage in pain, drugs, kids, bodily functions (if you catch my drift - yuck!), or anything else that may be illegal. I hope to make many new friends here. Hope to hear from you soon. TonyG P.S. I am married and very discreet. I just want to be up-front about that. Honesty is always best.
Buggy's Chat & Dating Profile
Vale, Oregon, US
Just starting this journey, its taken far too long. 35, divorced, 5 kids,
Kskmansnm's Chat & Dating Profile
Grants Pass, Oregon, US
Jennwnwnwnwnbwheiejjejejeje snake. S s
Squirral's Chat & Dating Profile
Chiloquin, Oregon, US
I'm just a single guy that would love to find a wonderful tgirl that would love to me my girl. I'll treat her as a proper lady unless she wants something else.
Tcat1987's Chat & Dating Profile
Rainier, Oregon, US
Looking for a good time with a shemale
cindy13's Chat & Dating Profile
Redmond, Oregon, US
4/2023...OK literally been 10 years since any empty nesters and the MRS. is OK with the androgynous look around the house, but not pushing it much beyond skinny jeans, top and flats. Still have Covid hair, not had it cut since lockdowns. Got on again for the first time since shockwave died...the people here are still awesome, but having trouble navigating around still. So, if I can remember how I logged on,I'll be back. 7/11/13 Yikes! I'm guessing 2 years since any updates...My Cindy time is down to almost 0 (zero). Thought that when the kids turned 18 or 19 they would move out. WRONG. I do get to keep smooth now (amazing how long a stick of deodorant lasts when applied to skin), but the chest is becoming an area of confrontation. Still on flickr if you have way too much time on your hands. 7/11 Wow, been a while. Still same ol me.. but the Misses has decided that smooth legs are ok, all of the time. I do still stop by for the occasional chat session, but please be nice, and take the half second to spell out most of your words. 11/09 Well my wife surprised me again!! SHE painted my nails and let me shave...Love you Hon!! 6/09 HI again..After 26 years, my wife has maybe not accepted Cindy, but at least realizes that she is not going anywhere (even commented on my hair and clothes!!). Don't give up....if the marriage is strong, it will make it. Love you Hun! 12/07 It has been just about a year since I got up the guts to flaunt myself here. Thanks to those who have left a comment..they have all been nice! If I am in chat, I am there to relax with friends, but I can always use more. Full profile is a BIG help. Not being a guy is a big help too.This should be read I don't date!!!! Where to begin..Closeted long time CD, Shaved my legs (at long last), and surprised my wife. OOOPPPSS!! Love nylon any where on my body. Favorite look is a bit slutty, or Office gal. Best achieved look is 'guy in a dress' (NEVER under estimate the power of PhotoShop). I would like to thank all of you that had the courage(and camera), to post before I did. Been looking at all of you for a LONG time before getting the nerve to post. I am not looking for anyone, or anything, just wanted to get 'out' (OK, show off)
Dothels's Chat & Dating Profile
Medford, Oregon, US
A straight male looking for some deep conversation with a m2f

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