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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.

Trans contacts for hookups from  Chicago, USA

  • TV/TS/CD
  • Straight Male
  • Age: 34
  • USA, Illinois, Chicago

am easy going , a shy type and love someone who is honest and caring about my son and i cause a a single mother and want someone we could build a lasting relationship together .i love swimming ,hiking,and playing tennnis.

 77 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 63
  • USA, Illinois, Chicago

I would much rather it be like a friendship that develops into something bigger. I would like someone who is smart, funny, interesting, open minded with a great smile. When I say open minded I am mostly saying that because I am Wiccan, not as a code for an open relationship (to each their own but not my thing). I

 16 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 27
  • USA, Illinois, Chicago

Hello everyone I'm Linda looking for longtime relationship

 1452 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 35
  • USA, Illinois, Chicago

Opening minded a real freak mad head skills creamy hole

 235 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 25
  • USA, Illinois, Chicago

I'm a quiet, kind, loyal. A great meaning for me is a human's soul. Circle of my interests is various. I like the literature, music, and cinema. personality traits are; calm, honest, kind, loyal, flexible, elegant, sociable, sensitive, gentle, cheerful, optimistic, romantic .My perception of an ideal , I would like to see near me clever, intelligent, and reliable man. Which would require my emotional heat, capable to like and respect the woman.

 136 people like this

  • TV/TS/CD
  • Bi Male
  • Age: 60
  • USA, Illinois, Chicago

Post Op transsexual easy going and loves to have fun. I respect myself and others. Don't care for rude people. I'm a lover not a fighter.

 168 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 30
  • USA, Illinois, Chicago

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

 75 people like this

  • TV/TS/CD
  • Bi Male
  • Age: 46
  • USA, Illinois, Chicago

I'm a new gurl vesatile top that would love to meet mature cd playmates that like to bottom

 63 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 30
  • USA, Illinois, Chicago

I'm 31 years old, living in the Chicago region. I'm interested in meeting a man or a transgender person aged between 40 and 90. I'm 4ft 11in (150 cm) I will travel for hookups

 60 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 34
  • USA, Illinois, Chicago

am lora , am new here. ask me to know more about me

 10 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 30
  • USA, Illinois, Chicago

My name is Thelma . I’m 30 years old, 5 feet tall 150lb. single. So this whole dating thing is new to me. I love to laugh, hardworking, love the beach, hiking, sports, playing & watching, cars, picky eater, dog’s, family means a lot to me, honest & I like helping people any way I can. Call me a hopeless romantic... I’m hoping to find true love again. I do work as an office clerk before i got laid off but i stay with my granny here in Chicago, Illinois .I wanna get married again! I’m looking for someone with similar interest....

 117 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 54
  • USA, Illinois, Chicago

Well am single,with no kids and never been married.whiles looking to find a conscious man to build monogamous relationship and also share good and bad together..possible have Kids with him..So are you willing to have Kids?

 33 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 31
  • USA, Illinois, Chicago

I am cool I don't play with someone attention..love

 171 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 30
  • USA, Illinois, Chicago

I’m looking man that I will spend the rest of my life

 185 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 44
  • USA, Illinois, Chicago

I am pre-op transwoman and willing to try anything

 21 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 26
  • USA, Illinois, Chicago

I'm just here to have fun, meet other crossdressers and guys who are into crossdressers.

 50 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 34
  • USA, Illinois, Chicago

I am young and cool looking for a serious relationship

 459 people like this

  • TV/TS/CD
  • Bi Male
  • Age: 19
  • USA, Illinois, Chicago

So I'm looking for someone to talk to. Preferably a partner, but I'm definitely up for friendships as well

 15 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 39
  • USA, Illinois, Chicago

I am very headsonme person and cuite and outgoing and more

 18 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 27
  • USA, Illinois, Chicago

I’m young transexual . I like bi guy. Would love to have relationship with bi if possible or open for anything :)

 217 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 21
  • USA, Illinois, Chicago

Hey :) im a college sissy looking to explore this side of myself as well as make friends. I love to dress up, especially in costumes, since I was little and I think I'm done keeping it in public. Im working on make up and getting a storage space for a hidden wardrobe, but I want to become confident in all of myself! I love to laugh, I play guitar , i love star wars and scary movies, and I have a huge sweet tooth. I can be very dark with my humor but in general I just like people who are honest and don't take things too seriously.

 92 people like this

  • TV/TS/CD
  • Bi Male
  • Age: 43
  • USA, Illinois, Chicago

40, act 20, love my nylons and miniskirts w heels, . love being touched, . . and held. need lots of attention, . . . like being told what to do, . . would like to be tied up, . . and manhandled, . . I'm a profesional, . w career, . . enjoy, . music, cooking and painting, . . next to drinking and dressingng

 82 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 54
  • USA, Illinois, Chicago

Fun love, full time femmine girl who Loves dating men

 115 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 39
  • USA, Illinois, Chicago

Looking for someone to have a great time with and experience life

 47 people like this

  • TV/TS/CD
  • Straight Male
  • Age: 49
  • USA, Illinois, Chicago

Love to dress up. . love to have my panty covered ass punished, fucked, spanked , ect. . ! ! !

 75 people like this

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