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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The difference between me and a mosquito is I don't stop sucking when you slap me lolTrans here looking for some fun and new experiences here and meetups. Still exploring in shape and attractive. Into intelligent, clean with a sense of humor |
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MISTRESS LISA LOOKING FOR A HONEST LOYAL LOVING AND CARING. . .HONEST GOODLOOKING KIND AND RESPECTFUL MISTRESS... LOVES FISHING, COOKING , HIKING, CAMPING |
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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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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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See other sections to find outTransbian for other transwomen nothing more to say |
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sub-leaning switch seeking a committed FLRSerious about wanting to serve the right owner. All of my relationships have been kinky, but this is the first time I’m looking to go all the way. |
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I’m sub bot for dom top. Oh my god i have to typeJust asked me and you’ll be surprised oh my god needs to be 50 msg |
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Current college student looking for some fun, my pronouns are theyhe and I’ve been on test..I enjoy getting drinks and dancing, I’ve never been with more than one person before and would love to try |
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I am a transitioning woman 2 years in looking for a relationship with an attentive man.I am 5'9" tall 140 lbs, long grey hair, small breasts, long legs. Preop |
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Hello???? I am unsure of what to say here you’ll find out stuff out from mostly talking to..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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Sweet Feminine Sissy Seeking A Man For EncounterHi. I am a feminine cougar who enjoys the comfort of a man. I'm 58 & 114 lbs. Totally smooth and a CD for the man I'm with. Enjoy making love & doing what a sissy does, sucking & fucking. Seeking a total top man who enjoys the company of .. |
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Hiya, iam Wendy new here, I would like to meet new friends, iam in transition mtf and new ..Iam honest, friendly, and considerate of others, just want to make friends and chill |
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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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Almost 60 and still looking for my soulmate. I’m hardworking, filled with self love, creat..I’m easy to hug, to hold, and to nurture. I’m pretty good looking at 59 and feel great. I love golf, long walks, great movies, reading, music, honesty, and devotion. |
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I am a crossdresser, I love to go down on men and women, I have had threesomes wife wife a..I dream of sucking ****everyday and eating creampies |
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Hello from Chicago, looking to find femdom and meet!I pretty much live full time as a woman, into Japanese doll fashion |
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Trying to expand my horizons I would like to experience a threesome with some nice well en..Well I've been watching a lot of movies and I've been seeing a lot of Ts enjoying more than one man and I'm a little jealous so I would like to try it too seriously |
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Just me look at me♀️♀️♀️♀️♀️♀️♀ ️❤️❤️❤️❤️❤️❤️❤️❤️❤️ |
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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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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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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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Sweet ts looking to meet a straight man for funLooking for decent guy, who is a total top or bottom and enjoy oral and more. Interested in curious newbies and those guys that don't get enough at home and need to release tension . |
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I’m a sugar baby who only accepts online-only arrangements. I prefer to keep things online..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 conve.. |
