Join TransGenderFriends.com and browse our City Directories for the most popular personals for online dating in the trans community. Why contact an escort when Local transwomen, ladyboys, trans & crossdressers in Chicago are online and eager to meet up now. Whether you are looking for someone to talk to or a casual meetup, our members are discreet and your identity will stay safe.
Check out our Chicago gallery below, filled with the latest horny photos and videos of local trans, non-binary, and crossdressing members.
Nearby to the North West Skokie, Evanston, Harwood Heights, Lincolnwood, Morton Grove. Nearby to the South East Calumet City, South Holland, Dolton, Riverdale, Thornton. Nearby to the South West Elmwood Park, Cicero, Oak Park, River Forest, Glenview Nas.
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I will love to explore more with like-minded people and have some rigorous funAm a very lovely person that you don’t wanna miss out on. Am a transgender with pre-op. Xxx come let evplore. |
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Hey sub! I'm here to explore and teach a submissive male about the lifestyle and also here..I'm sexy and genuine Mistress who is in for all kinky relationship and ready to make it happen.. Also I would love to know my subs willingness to serve while I train him on his fantasies.Seeking a sub with whom I have connection. Any size, age, race .. |
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Big heart, bad jokes, let’s build something real"More about me. The magic happens when I'm surrounded by genuine energy, whether it's dancing to 2000s throwbacks with friends, deep convos over coffee, or getting lost in a good book on a rainy day. I light up around kind people, good music, and spon.. |
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Confident trans . TattedTransTeas e here to flirt, tease, and please Bold vibes, naug..I'm a bold trans radiating confidence I get a thrill from flirty banter, steamy nights, and owning my truth Happiness is sultry vibes, and teasing hearts senseless Catch me living unapologetically, sparking desire, and making every moment a delicious.. |
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I am a trans girl exploring my wildest kinks and fetish lifestyleI am a trans girl exploring my wildest kinks and fetish lifestyle and am really naughty. |
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Exploring Kinks and FetishesI am a trans girl exploring my wildest kinks and fetish lifestyle and am really naughty. |
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I’m a trans female who loves to explore fantasy worlds, love everything naughty and fun, w..I'm 31 years old, living in the Philadelphia region. I'm interested in meeting a couple or a man aged between 32 and 79. |
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Honest and easy going person. Love to exploreSingle and searching. Caring and honest in all I do |
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Trans woman who wants to exploreWhen loved and been taken care of, Also like fun moments |
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I love to have sex with my subSo there you are—draped in control, every glance a command, every whisper a promise. You don’t ask for permission; you give indulgence. Being a mistress isn’t about secrets or shadows—it’s about owning your power, making someone ache just to please y.. |
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A newly transitioning female in needNewly transitioning female in need of some new friends or someone to help me thru my transition |
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I’m a Trans mistress seeking a sub for worship and role play.I hope you know how to serve and treat a Goddess like me.. I am very adventurous. |
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Trans girl looking for a submissive partnerI like pegging and spanking my sub, I like bondage too and I will give you privilege to such my cock if you prove worthy. |
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All My Yummy Stuff AvailableA Girl with a Big Surprise |
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Trans & a topI like topping men who look like they would have bullied me in. It's such a rush of power. |
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Hey how are you doing today are you enjoying the weather todayLooking at your big cocktail turns me on when I see your precum. |
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Subby Pinky pet, without a owner.Someone I'm comfortable and secure with, affirming kinky type. |
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Exploring my wildest kinks and fetishesExploring my wildest kinks and fetishes and meeting new people with the same interest |
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I'm 28 years old, living in the Chicago region.I'm 28 years old, living in the Chicago region. I'm interested in meeting a man aged between 35 and 99. |
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A trans lady looking for her Toy boyI’m a strict mistress who’s in search of my loyal toy boy and not someone who’s coming in to stress me a lot I want loyalty and commitment. I’ll gag you a lot and make sure we explore to the best of limits. |
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Lovely meet with my lovely friendsAm just simply person and kind with lovely heart ♥️ |
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Hot hung man looking for femboys to lustI first wore my Mommy’s panties on my 12th birthday |
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I’m Nat Nat but you can call me natty babyI’m Nathaniella but you can call me Nat. I’m 24 years old, living in the Australia Plains region. I’m interested in meeting a man aged between 18 and 70. Let’s text for any kind of fun. |
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I'm a trans girl available for hookup and BDSMI'm a trans girl available for hookup and BDSM. |
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I just want to live the moment. Enjoy myself.Practice martial arts, Travel, Go to the movies, Dance, sing, play the guitar and play video games. |
