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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.

Top other cities in   Illinois

Springfield Rockford Peoria Illinois City East Saint Louis

Trans contacts for hookups from  Chicago, USA

  • AliyahSissy
  • TV/TS/CD, Straight Male
  • Age: 24
  • USA, Illinois, Chicago

I’m looking for a male or female led relationship. Being dominated is my ultimate fantasy.

  • onego504
  • TV/TS/CD, Straight Male
  • Age: 28
  • USA, Illinois, Chicago

Love is a nutrient that can never be lost in life. Life is because of love, it becomes colorful; in the family, it is because of love, it becomes happy; my life, it will become more exciting because of you.

  • patoote159
  • TV/TS/CD, Straight Male
  • Age: 29
  • USA, Illinois, Chicago

Hard gentle loving ts here looking to have some fun tonight

  • Tiffanyy321
  • TV/TS/CD, Straight Male
  • Age: 29
  • USA, Illinois, Chicago

I would love topping you or letting you top me or both down for kissing

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

I love being humiliated and used, sharing my pics and videos

  • tiffanyke753
  • TV/TS/CD, Straight Male
  • Age: 29
  • USA, Illinois, Chicago

Try this site looking for newfriends and maybe more

  • edhiggin544
  • TV/TS/CD, Straight Male
  • Age: 66
  • USA, Illinois, Chicago

Some one to chat with and enjoy each other's company

  • petoj059
  • TV/TS/CD, Straight Male
  • Age: 45
  • USA, Illinois, Chicago

Love high heel boots, dressing like women, wigs ...

  • Jessica4u2cumin
  • TV/TS/CD, Straight Male
  • Age: 30
  • USA, Illinois, Chicago

I love feel as a gurl love to cd and get spanked by daddy love role play

  • angela1157
  • TV/TS/CD, Straight Male
  • Age: 38
  • USA, Illinois, Chicago

Hi there i will be very happy to get to know more and shear some pics together and see where it goes to

  • ssmtr751
  • TV/TS/CD, Straight Male
  • Age: 41
  • USA, Illinois, Chicago

Fun with others in the chatting room and have fun s

  • stoneydo874
  • TV/TS/CD, Straight Male
  • Age: 64
  • USA, Illinois, Chicago

Looking for men I m a crassdressers live as a wild girl who loves to suck and be fucked alot

  • philipbr942
  • TV/TS/CD, Straight Male
  • Age: 58
  • USA, Illinois, Chicago

I have a fantasy of someone forced me to cross-dress take me out in public treat me like the b**** I am and maybe a little sissy maybe make me a little maid a little sissy b**** man or woman don't matter or couples hope you all

  • femcdgur1l
  • TV/TS/CD, Straight Male
  • Age: 33
  • USA, Illinois, Chicago

like hot chat and showing me hot sexy pics and gifs;)

  • prodigit948
  • TV/TS/CD, Straight Male
  • Age: 62
  • USA, Illinois, Chicago

I LIKE TO ORGANIZE & CLEAN HOUSES ANY TAKERS OUT THERE?

  • ashleyahicsm605
  • TV/TS/CD, Straight Male
  • Age: 34
  • USA, Illinois, Chicago

I'm 31 years old, living in the Chicago region. I'm interested in meeting a man aged between 18 and 39. I will travel for hookups

  • love2bottomforhung
  • TV/TS/CD, Straight Male
  • Age: 56
  • USA, Illinois, Chicago

Im so ready to find someone that can trat me like a lady in publick and a whore in the bedroom

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

Just looking for a girl who loves to hang out and do fun stuff

  • illianae072
  • TV/TS/CD, Straight Male
  • Age: 24
  • USA, Illinois, Chicago

Personal fantasy would be me being the only exotic dancer for a bachelor party of 20 men and ending up giving oral sex and being anally violated by all of them.

  • billy194Chicago
  • TV/TS/CD, Straight Male
  • Age: 63
  • USA, Illinois, Chicago

I am a very romantic guy looking to fall in love again

  • sweetbrat01
  • TV/TS/CD, Straight Male
  • Age: 24
  • USA, Illinois, Chicago

I do well when I have a lot of structure and guidance in my life. Looking for someone who understands tough love to provide that.

  • RoyalCavendish
  • TV/TS/CD, Straight Male
  • Age: 33
  • USA, Illinois, Chicago

During quarantine I put a bunch of people into a trance over the phone and led them to orgasm.

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

Just wanna get fuck or fuck someone I host and travel

  • palmiw846
  • TV/TS/CD, Straight Male
  • Age: 49
  • USA, Illinois, Chicago

looking for dom females and couples into to taboo m

  • Shu689MountLaurel
  • TV/TS/CD, Straight Male
  • Age: 64
  • USA, Illinois, Chicago

Me and another crossdresser being intimate I had a couple dicks in my mouth but that was it. Two guys here swallowed me

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