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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Seeking a lovely person to play withI’m a tall slim, smooth CD gurl mostly a homebody. Enjoy creating a cozy comfortable living environment. I’m a very sensual person that would love to bond with a like minded partner |
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New Versatile CD Looking For Fun!!!Hi! I’m exploring a new side of myself. I’m a versatile CD looking for women, other cdtrans. A drink at the bar, nice dinner and then dancing the night away sounds like the perfect evening. |
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crossdressing for fun and injoymentim 73 biu look like a 40 year old have real breast long hair real and love dressing up very feminent |
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I like anything that isn't disgustingI'm a transvestite, and hopefully sometime soon I can transition. I prefer to go by Abigail. (She, Her, Hers) |
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Sexinsingle looking for a freaky friendI hate filling these out I will write more later. Don't be shy |
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hot and sensual CD looking for fun timesi wd love to be your gurl … |
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VF seeking other crossdresser, transvestites, drag queens, for fun and dressing up as les..Crossdresser fully dressing up seeking like minded others that dress or wear at least a minimum of silky nylon panties and sheer silky thigh highs. |
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shy chicago gal looking for sameI do this every once in a while,Not full time,But would love to find a Full time "Gurl" |
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Love you and love ❤️ you I loveNeed a hook up with any sexy shemale Thanks for your time |
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Going yeehaw in a southern accentI'm looking for another human whose just as weird, if not weirder, than me. Down for anything and everything adventurous! |
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Bottom black non passable seeks topI am a non passable (voice, masculine body type, facial hair) black crossdresser looking for white straight acting tops |
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Firstimer. Curious and ready today36 bi-curious male. Athletic toned. Been paitienly waiting for something to come along |
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I want to have someDiscreet funHi. I sm a narried latino Male and love to dress very sexy |
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A simple girl, inside and out, looking for a friendI am 54, 5'8, 206 and looking for a person to treat me kindly. Find a new way or reason to make me feel special each day, and I will return the affection. |
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Travesti sofia por que soy como quiero serLinda travesti de closet en el area de chicago ... |
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Mature Crossdresser for romanceMature plus size crossdresser looking for gentlemen for romance |
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Boy in a skirt looking for that special galI enjoy nature and taking as many walks through it as often as possible. I also love to read, go to concerts, dabble in art and collect tattoos. Looking for a gal who is adventurous and willing to take risks. Basically someone who loves life and make.. |
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Nice Want to be Female look for nice MalePart time crossdresser, very nice person to get to know |
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femme cd looking to be spoiledhi!(: i’m looking to keep you happy, and be spoiled |
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Looking for dates to eat take walks at nightJust to have nice talks and more see where it goes and see what you like |
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Lifelong Cd looking for friendshipMiddle-age Sexy Cd looking for adventure and friendly chat |
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Bi M 59 looking for connectionMarried guy, Wife has been nonsexual for years now. I am fit, fun. a bit freakykinky, Gentle spiritual. I've been a meditator for years, I would love to explore tantric connection with a woman, man or couple. Something deeper and ongoing would be per.. |
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Just lil crossdressing lingerieCloset lingerie most of my life Love go store and buy new things for wife haha she won’t wear but I love too |
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Looking 4 U Maybe U R Looking 4 MeMarried but in closet. Love to wear my wife’s cloth. When she’s gone ! Lol. Have time during the day to chat and maybe webcam if there’s trust. |
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Looking to have some fun. Play around.I'm white skinny and am up for almost anything. Like to feel sexy. |
