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 am dominatrix am turned on by playmate that value this lifestyle who cares about what pe..I am mistress Queen I am sweet , soft, sexy , hot am in need of a lucky playmate |
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I'm 51 years old, living in the Chicago region.Life goes which am open to know everything that comes my way and looking same thing |
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I am new to this, and am currently looking for a brat tamer who wouldn’t mind showing me t..Music and concerts make me happy an attentive, supporting partner makes me happy. Giving completely into submission and flowing straight into directing orders makes me happy. |
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I'm 27 years old, living in the Chicago region.I'm 27 years old, living in the Chicago region. I'm interested in meeting a transgender person or a couple or a woman or a man aged between 18 and 90. |
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German Sub like to be a Sissy in serve you to the fullestI am a sub, from germany, you can use me for daily task, you need a ride, text me, you need someone to clean, text me, you need someone for grocerys text me….make me your sl*** |
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Want to try something new and exciting want a dominant women or transSeeing trans woman that are hot and sexy and want to be the first one to teach me about my new experience |
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Lookinf for an ownsr exposure sissification feminize humiliationLove to submit cuckold married and in closet want to be exposed |
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Out here to express and enjoy my fantasies.Hello there! I'm Ann a confident and compassionate individual who believes in embracing life to the fullest. I identify as transgender, and my journey has shaped me into someone who values authenticity, resilience, and genuine connections. |
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Hi I’m Laura, a sweet and playful CD.I’ve been dressing several years and it’s been absolutely wonderful. My dressing and meeting others has been in private since I need to be discrete. Looking to meet other CDsTSTG dress with, be feminine and share intimate pleasures. |
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Hey I’m Martha and I’m on here looking to meet and be with someone hopefully! Let’s get i..Meeting people and being around my loved ones makes me very happy. |
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New here looking for someone to have a fun and to try new things likeminded in new people ..I am simple and very fun person, Very friendly. I am oriented on having a serious relationship and i want build my own happy.... |
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hi how are you doing today and what are you looking forhi how are you doing today ad what are you looking |
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I am self-sufficient , Beautiful, happy, secure, self-confident, psychologically aware, e..I'm 48 years old, living in the Chicago region. I'm interested in meeting a transgender person or a man aged between 42 and 99. |
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Hi. I am a CD that dresses fully with makeup. I try to be the complete girlfriend. I would..I love being with men. I am open to most anything. Just ask. |
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Looking forward to meeting other crossdressersI'm 66 years old, living in the Chicago region. I'm interested in meeting a transgender person aged between 56 and 76. |
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Discreet but adventurous...Fetishes really center around brainwashing and mind control, but also porn. Get me in front of some porn I like and you're well on your way to emptying my mind and filling it with, well, whatever you want. I want to be controlled. to worship masculin.. |
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Looking for a submissive man that’s willing to do anything for me I deserve itYoung trans girl looking to explore more most men are not willing to take it far with me I have dark fetish for men wanting them beat and spanked I love it |
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Part time CD looking for fun timesI’m very open to almost anything. I love wearing pantyhosestockings, heels, and having my nails painted |
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I'm 40 years old, living in the Chicago region.I'm 40 years old, living in the Chicago region. I'm interested in meeting a transgender person or a couple or a woman or a man aged between 21 and 51. |
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I'm 28 years old, living in the Chinchón region.I'm interested in meeting a transgender person or a couple or a woman or a man. |
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Looking for 2 bbcs in chicago areaI'm a versatile trans woman just want to experience 2 or 3 bbcs . |
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I’m available for meetup and friendly funI love fun anal fetish hardcore twosome carsex big |
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I am a romantic woman, who wants to be special for only one man. I am not afraid to expres..I'm 40 years old, living in the Chicago region. I'm interested in meeting a transgender person or a man aged between 40 and 90. |
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Just a lonely crossdresser looking for a loving, caring female.I don't like implicit rules. I don't like dressing or acting like what prople would expect from me. I prefer not to be put in a box, and choose to follow my heart. I love the incredulous look I get when I apply red lipstick before every time I go out.. |
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ummm i go by EQ. im just trying to find out what i like. i mainly just want to experiment ..something that makes me happy is people who are respectful towards me and fulfill my fantasies. |
