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.
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new to the community and looking to experience new scenariosI love bad romance novels, music, taking walks, and cooking |
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I am crossdresser and like to meet like mindedI like western and Indian traditional wear, I like to wear jewelry. |
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62 yomwm lookiing for discreet lingerie encountersBeing with other like-minded people turns me on. I like to share the wonderful feeling of being dressed n all sorts of sexy lingerie |
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New here looking for someone to have fun and and exciting new opportunities likeminded....I am simple and single very fun person, love meeting new poeple for exciting great time and fun especially try new things like sexual adventures.... |
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Looking for crossdresser to play with you must host or car play is fine.i like to try different types of thing as long it aint gross! |
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I'm just your typical transgirl. Just had my boob job. But it was all worth it. Now I feel like I had the puberty meant for meI'm a pretty open girl if you know what I mean. I really like black men |
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Hello to all. I am a respectful and devoted guy looking for my last first kiss.Femininity, compassion and caring is what I am looking for. |
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I'm transitioning from male to female I love cleaning houses the cooking I'm attracted to talk black menI would love to be used and and taking advantage of the biopussy |
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I love cock and love eating cumI’m sissy bimbo who lives to suck cock and eat cum |
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Sissy male looking please you and will follow your orders.I enjoy pleasing others sexually. I am open to video chat, and will love to dress up for you and follow your commands. |
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I appreciate little things in life so don’t be afraid to message me.My friends always complain about me talking too much…but that’s not the only thing I can do with my mouth. |
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Hey I’m sissy cd submissive, buttom looking for tops around Chicago I’m also down for hookupsWell I’m also a wanna be trans I’m looking to meet tops on here |
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Still new and I have no Idea if I'm even gonna use this, but I'm here now and ready for... something idk.I like video games, anime, books, and writing. Yeah. |
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simply fun and friendship, looking for good peopleSimple life, nothing special , looking forward for new friends |
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Gorgeous, pretty, Classy, independent, educated and professional woman looking for an older mature and financially insecure and ndependent gentleman for great times and casual relationship..Want to have great times, no head cases, dependency or marital issues. |
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I am seeking some casual fun maybe relationship if we clicked xxI'm not picky person all i want is to be satisfied, Down into subdom too love to explore myself if you are interested just mssg me xxx |
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Simple TS here looking for some fun now..I am open minded person love to explore and learn more things here and love meet new people xx |
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a kinky ts heavily into sph 3i’m looking for a man , come with the cum ;3 |
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I am new here looking for someone to have a great tieme and would like to meet people and have some fun....I am simple and single and im up for almost anything, i am very playful and im always up for horny advntures.... |
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I'm looking for some fun and new experience here and meetups. Still exploring in shape and attractive. Into intelligent, clean with a sense of humor. Open minded and super laid back.Hi. I am seeking for anything and actually I am an experience but I am seeking for someone to explore with |
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Looking for someone to spend quality time with. Want someone to enjoy life with. Be supportive of one another.I am 6'3''and I work on a farm. Like to go dancing fishing and going on walks. Like to go out to eat and watch movies at theater and at home. Looking for a good companion to spend the rest of my life with. |
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Simple TS here looking for some fun now..I am open minded person love to explore and learn more things here and love meet new ppl. |
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I am new here looking for somone to have a great time and meet new people and share sensual ideas with an open mind to anything ...Im simple and very fun trans and I’m down to earth person looking for love and looking for some fun and new experience here and safe meetups. |
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Sweet guy wanting to dress more and more, looking to meet the ideal partner, be it male or female. Very Bi Sexual hereLove Dressing up, not out yet but getting closer and closer |
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Gender fluid and pansexual in Chicago for a dayGender fluid bottom, in Chicago for a day and trying to party. |