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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 Glenview Nas

Trans contacts for hookups from  Chicago, USA

  • mourlath279
  • TV/TS/CD, Straight Male
  • Age: 46
  • USA, Illinois, Chicago

Love to btm party and ppl lay with ithers. Like kink taboo roleplay

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

Naughty gurl fantasy. It would be fun to play dress up with new friends.

  • cheekles351
  • TV/TS/CD, Straight Male
  • Age: 67
  • USA, Illinois, Chicago

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.

  • taylor3663
  • TV/TS/CD, Straight Male
  • Age: 21
  • USA, Illinois, Chicago

I'm looking for a dom who's into BDSM, pet play, or sissy play.

  • thre201
  • TV/TS/CD, Straight Male
  • Age: 26
  • USA, Illinois, Chicago

Looking for naughty mate who loves dirty talk and very down to earth

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

Im a transgender and im here to meet and have some fun rightnow

  • Funfun8319
  • TV/TS/CD, Straight Male
  • Age: 36
  • USA, Illinois, Chicago

Looking for newfriends and maybe more but please be good to me Visiting

  • TranSweet
  • TV/TS/CD, Straight Male
  • Age: 36
  • USA, Illinois, Chicago

Sissy for mistress to use me to fulfill your sexy desires and fantasy

  • jokeesm745
  • TV/TS/CD, Gay Male
  • Age: 55
  • USA, Illinois, Chicago

Listen to House, Trance, Hip Hop & Latin Freestyle. Enjoy movies & Long Walks ,Conversations & Laughter

  • rsl483
  • TV/TS/CD, Straight Male
  • Age: 23
  • USA, Illinois, Chicago

Id ont wnts to includ eq things here le pardones skck

  • tsmistressana765
  • TV/TS/CD, Bisexual Male
  • Age: 38
  • USA, Illinois, Chicago

I'm 35 years old, living in the Chicago region. I'm interested in meeting a transgender person aged between 30 and 90. I will travel for hookups

  • muchacho69
  • TV/TS/CD, Bicurious Male
  • Age: 54
  • USA, Illinois, Chicago

I'm 51 years old, living in the Chicago region. I'm interested in meeting a crossdresser for mutual sensual pleasures. 40 and 59 is my preferred age range. I will travel for hookups.

  • a1sex508
  • TV/TS/CD, Straight Male
  • Age: 40
  • USA, Illinois, Chicago

love to party with other cds trans im verse but really love to ride

  • qui186
  • TV/TS/CD, Straight Male
  • Age: 25
  • USA, Illinois, Chicago

If you like anime and just wanna chill come talk...

  • efrac21ya5
  • TV/TS/CD, Straight Male
  • Age: 31
  • USA, Illinois, Chicago

A guy that knows how to tain me put me in my place .

  • elect20
  • TV/TS/CD, Straight Male
  • Age: 53
  • USA, Illinois, Chicago

On hormones and testosterone blockers ready for complete feminization

  • jm6256y
  • TV/TS/CD, Straight Male
  • Age: 30
  • USA, Illinois, Chicago

Am a nice girl I show love to any man that show me love also And the man must take care of me I love my country USA

  • minnesotac896
  • TV/TS/CD, Bisexual Male
  • Age: 56
  • USA, Illinois, Chicago

Love dressing up and playing with other gurl's who love the same thing.

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

Newbie CD here looking for friends and play! Mostly into women and other sissies.

  • morganjusti014
  • TV/TS/CD, Straight Male
  • Age: 36
  • USA, Illinois, Chicago

Ask me i will tell you if you we like to hookup with me

  • fem86Chicago
  • TV/TS/CD, Straight Male
  • Age: 67
  • USA, Illinois, Chicago

I consider myself to be a straight submissive female. I am looking for masculine dominate dudes for intimate encounter. I love wearing the old fashioned nylons, garters and straps. I like men of all races. I fantasize a Muslim dude intimate with me in a burka. Stretch my asspussy I love cream pies! I am looking for a dude who loves to fuck who lives in the Chicago area. I hope to find dudes for regular encounters. I can host in my motel room. I have always needed a vagina. I can still have one.

  • sex523
  • TV/TS/CD, Straight Male
  • Age: 23
  • USA, Illinois, Chicago

Hot cum in my tum I want hot jizz in my mouth. Cum in my ass

  • cloudddan016
  • TV/TS/CD, Bisexual Male
  • Age: 53
  • USA, Illinois, Chicago

I am a warm creative trustworthy male seeking a transgender female or transexual for a possible relationship. Serious replies only within the Chicagoland area

  • nbsea69
  • TV/TS/CD, Straight Male
  • Age: 33
  • USA, Illinois, Chicago

Looking for a Dom female to put me in my place and guid me to their ecstasy. Hopefully allowing some pleasure for this little sissy as well. Possibly interested in meeting with men with my dom present.

  • fhh8888
  • TV/TS/CD, Straight Male
  • Age: 54
  • USA, Illinois, Chicago

Must love dressing Love to play Always safe Have a large collection to share

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