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'm looking for a pretty trans womanAlways up to trying new things. Annie takers out there |
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I'm looking for a Girl that I can have fun being a girl withI like to cross-dress as a girl look proof of that like that |
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I love everything about crossdressers.I'm just a bi-curious person that has an addiction for crossdressing. |
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Hello, i’m a sissy for a LTR with a dom. If you’re interested let’s chatFor feminization pegging and sissygasm with caged clitty |
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Bi-sexual male looking for some funAn older gentleman looking for some fun and open to new things |
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Young sissy looking to be dominated. Bi21I’m looking for a male or female led relationship. Being dominated is my ultimate fantasy. |
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hello dear , i would like to make a friendscooking, traveling, fashion and art, music, cinema, |
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Hiya sexy girls iam Wendy Jean New hereI want a hookup with crossdressers and shemales and trans girls |
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Bi-curious tottally Bottom cock slut wanting to please all men and do EVERYTHING you want ..Would LOVE to walk into a motel room full of hard well hung black studs just knowing im going to let them have they're way with me taking turns filling me full of hot juicy cum & letting me clean all my ass cream off of each & every black cock after .. |
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Just seeing whats out there~~~Dont travel. Host only. Into other sissiesCD as well. |
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I am looking for someone who like to have fun and have good connection withI am looking for good friendship and may be more.I like someone who is honest and caring |
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Looking for hookup but also looking for girlfriends for makeup tips etc.A woman or Gurl gives me makeover for a man, woman,or threesome |
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Sissy slut into being dominated, BBC, getting gang banged, eating cum and asspussies.I love being humiliated and used, sharing my pics and videos |
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Hi, wanting to be a sissy boi!Seeking dominant female to feminize me into a fulltime sissy boi |
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Like to have a good time acting girly and playfulLove to btm party and ppl lay with ithers. Like kink taboo roleplay |
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always in happy mood I love my lifeam very simple woman looking for a nice man to live with |
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Looking for new friends to chill withNaughty gurl fantasy. It would be fun to play dress up with new friends. |
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Sissy bitch in training, shaved and smooth and caged and tiny and limp inferior sissy bitc..I am still deep in the closet. But I watch a great deal of sissy hypnos, and straight porn where I identify with the girl. |
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I'm looking for a dom mastermistress .I'm looking for a dom who's into BDSM, pet play, or sissy play. |
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I'm very sweet and kinky love naughty thingsLooking for naughty mate who loves dirty talk and very down to earth |
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Looking for casual sex On regular basisTranswoman fairly new to Chicago. Love outdoors and pretty kinky |
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Good clean fun in lingerie and high heelsLet me dress for you and be your secret sissy no strings |
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guy who likes to dress as a chick, into anyone who wants to adventurei love to dress like a sissy and take cockdildos ;) |
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Like the Cindy Lawuer's song " girls just wanna have fun"Some one to chat with and enjoy each other's company |
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Simple trans here sweet and horny looking for casual fun right now,BDSMDiscreet MeetsFetishGroup MeetsHookupsLong Term Regular MeetsOnline ChatSex ToysSexual MassageSexual Roleplay |