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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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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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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I’m a sugar baby who only accepts online-only arrangements. I prefer to keep things online only. I’m a fun and witty person who loves to chat online. I’m also intelligent and well-educated. If you’re interested , then message me.I love cooking from scratch. I travel the world in my kitchen. I'm a medical professional. I take care of the elderly. I'm kind and nurturing but I'm a bit of a brat. I especially enjoy deep conversations. I am a bit of a flirt and some spicy conversations are def appreciated. |
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Dominating and feminzing new studentI'm into Sissyfication, Chastity cage, Bondage, Diaper, Findom, Humilation, Anal, Spanking, Crossdressing, Strapon |
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Mature Closet Cross Dresser Loves Other Crossdressers, Lingerie, Chatting Online.Slips Excite Me! Dressing Up Makes Me Happy, Teasing And Flirting Too Makes Me Happy ☺️ |
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Great older guy admiring. Loves CD, Meetings oral and moreEx CD. The more feminine you are the better life is. Likes Secretary , high heels nylons makeup, wig the works. |
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Hey.. I am a CD fem boy.I'm an Indian. I'm excited to meet people who understands me and utilise me accordingly. I will be happy when a girl orders me to do something for her. |
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Hello! Crossdresser looking for fun!Let's have fun! I am open to almost everything. Drop me a message and let's talk |
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I’m here for the…….show me what you gotI’m just here to make friends, explore and you know……… A bit weird with an interesting personality and deep perspective on life |
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Wanna hang with trans? cuz im looking for fwb or maybe long time relationshipIm excited to meet new people here, also looking for Long term relationship |
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Just me look at me♀️♀️♀️♀️♀️♀️♀ ️❤️❤️❤️❤️❤️❤️❤️❤️❤️ |
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Current college student looking for some fun, my pronouns are theyhe and I’ve been on testosterone for almost two yearsI enjoy getting drinks and dancing, I’ve never been with more than one person before and would love to try |
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Hello???? I am unsure of what to say here you’ll find out stuff out from mostly talking to me!!I’m unapologeticly myself and that includes being a relentless brat, I’m authentic and straightforward. So to sum things up I’m walking fireball |
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Hiya, iam Wendy new here, I would like to meet new friends, iam in transition mtf and new to the areaIam honest, friendly, and considerate of others, just want to make friends and chill |
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I'm available for fun 247 incallHi everyone I'm available for fun text me if you are ready |
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Just a guy who is into crossdressing hoping to find a dominant womanI’m really into crossdressing feminization and role play |
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I wish you gonna have a wonderfull day. Always smile because that helps to make life happier. Always choose to be happy its gonna help us to have a better world.I guess its not to late for me to find someone nice and respectfull to be with on trying some other things . Would love to see and try my luck |
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Hi! good day to everyone! Dtf sweet and horny looking for real meet and fun, I am up for anything and see where it goes.I am open minded person love to explore and learn more things here and love meet new people♥ |
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im new here looking for some funHello there! Im kate, Sweet social and loveable person who loves to have fun. Just hit me up and see what happens. |
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Looking forward to go shopping with a kinky ladyA submissive guy who. will do as he told kinky and fetishes bondage and discipline are fun |
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Live life to the fullest have no regrets ..gym lover and enjoy the outdoors! Love animals and nice cars .. |
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Im not flirty im just being extra friendly to someone who is extra.I promise im extra nice to those extra attractive i need a really nice guys to love me everyday and feel my self every night |
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New Chicago resident, looking to meet some other CD girls or admirers.Love to go out and feel like a woman, they feel of a short dress on, high heels, and the smell of my perfume |
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I like doing things like photography, gaming, dancing, etc. I also like going to new places and trying new things.I'm open to anything, open minded, passionate, adventurous, verse TS here looking for fun or my soulmate . . |
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I'm very simple, pretty and politeSeeking someone to vibe with or maybe more if we click so don't be shy and hit me up |
