Home > Countries > USA > Illinois > Chicago

Local Chicago GBTQ, transgender, transsexual & trans contacts

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.

Trans contacts for hookups from Chicago, USA

  • zabawana1637
  • TV/TS/CD, Bisexual Male
  • Age: 48

Welcome to my website. I love sex and I am bisexual. I love dressing up as a girl. High heels and stockings are my obsession. As soon as I dress up as a girl, I live in a different world. I am powerless and submissive. I'm turned on by tall men. Then..

  • jazzab803
  • TV/TS/CD, Straight Male
  • Age: 22

I’m new to all this so I need people to be patient and willing to educate

  • SissyslutAmi
  • TV/TS/CD, Bisexual Male
  • Age: 65

From the age of 17 I was molested by a neighbor and loved every moment. Where it may not be for everyone. It's everything to me. And nothing wrong with it. Now years later I'm proud to say I'm still living it. Join me.

  • MandyChi
  • TV/TS/CD, Straight Male
  • Age: 38

Looking for a regular partner that enjoy oral and has a lipstick fetish

  • favoritehuman001
  • TV/TS/CD, Straight Male
  • Age: 28

I'm looking for some fun and new experience here and safe meetups. Still exploring in shape and attractive. Into intelligent,clean with a sense of humor. Open minded and super laid back.

  • russ461
  • TV/TS/CD, Straight Male
  • Age: 42

I am open ask me anything you want I'll tell you later

  • baileybai368
  • TV/TS/CD, Straight Male
  • Age: 68

Love crossdressers men in panties is just the hottest thing in love it

  • kinkybadg936
  • TV/TS/CD, Straight Male
  • Age: 65

I live openly as a trans woman.. So please don't refer to me as a man or a crossdresser. I have many fetish interests, sissy attire, old fashion foundation garments, Bondage, over the knee spanking, humiliation, especially mental ...but that is some..

  • sonjay21
  • TV/TS/CD, Straight Male
  • Age: 25

I don't have a preferred body type or anything tbh. As long as your a good person I'm good. I do prefer punks and metalheads in style n asthethic tho

  • kayleighbor
  • TV/TS/CD, Straight Male
  • Age: 30

Mtf here need a FWB someone who can satisfy me HMU serious only looking now

  • breannaChicago
  • TV/TS/CD, Bisexual Male
  • Age: 51

Single and employed. Various interests carnivals, reading, seeing live music camping etc. Looking primarily for someone open honest and ltr possibly even marriage.

  • Blueznik53
  • TV/TS/CD, Straight Male
  • Age: 55

Creative artist and easy on the eye's. Looking for over the top pleasuring and passionate encounter

  • clowncream
  • TV/TS/CD, Straight Male
  • Age: 25

i like good listeners and more importantly someone who has good vibes and is open minded

  • wra201
  • TV/TS/CD, Straight Male
  • Age: 40

I believe, that man and woman as a couple should be a little similar one to another. I am not about appearance of course and even not about interests and hobbies, but about life position and rhythm. The main is not who you are or who I am but how thi..

  • MaddieHippyChick
  • TV/TS/CD, Bicurious Male
  • Age: 60

I want to find that person or couple that will treat me like a princess, at least for a while. LOL!

  • Chiheather
  • TV/TS/CD, Bicurious Male
  • Age: 66

I'm an old fashioned girl and I like to be spoiled. I like to dress in outfits that I like to see on real females, short skirts stockings and 5" heels. If you want to chat with me I can usually be found in the Hot tub. I'm not the thought police but..

  • JoanDressed
  • TV/TS/CD, Bisexual Male
  • Age: 51

I'm a new gurl vesatile top that would love to meet mature cd playmates that like to bottom ..sooo if you'd like "Kick" me

  • qcc938
  • TV/TS/CD, Bisexual Male
  • Age: 65

Hi, I'm looking for cross dressers and men who I can relax and enjoy the joys of cross dressing.

  • tspeanuttbutters
  • TV/TS/CD, Straight Male
  • Age: 35

i love art fashion film art i can be ur best kept secret

  • sexysenior087
  • TV/TS/CD, Bisexual Male
  • Age: 69

I love to kiss and fondle each other, slowly and sensually... Let us stretch our encounter out.

  • ClingyCelestina
  • TV/TS/CD, Straight Male
  • Age: 30

I'm open for anything.. I'm lovely nice and care 3

  • Sindeedres13
  • TV/TS/CD, Straight Male
  • Age: 56

I need to be controlled and dominated by my playmates.

  • Inamonanaani902
  • TV/TS/CD, Straight Male
  • Age: 31

Im 26 yrs old single, I am looking for long term or just hook ups

  • Peaceful94
  • TV/TS/CD, Straight Male
  • Age: 70

I’m looking for some like minded companionship and friendship

  • ShevanChi
  • TV/TS/CD, Bisexual Male
  • Age: 44

I want to take dressing, which I am very private about, public. I want to dress with another person...

Photos of real tv/ts profiles

Full size photos and videos available to registered members only Join now!