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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.

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

  • harrybarl
  • TV/TS/CD, Straight Male
  • Age: 67

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 ..

  • wendyjean
  • TV/TS/CD, Bisexual Male
  • Age: 68

Iam looking for a discreet domanit well hung crossdresser or trans for dating and sexual kinky sex I love to be submissive and sensual, Love dressing up in a sexy way iam on estrogen patch, and I am starting to get boobs that I love ia so exciting, r..

  • Carina1985
  • TV/TS/CD, Bicurious Male
  • Age: 40

Very submissive cd looking for permanent dominant type long terms looking

  • Samanthad723
  • TV/TS/CD, Straight Male
  • Age: 49

I am pre-op transwoman and willing to try anything

  • lexiwi85
  • TV/TS/CD, Straight Male
  • Age: 30

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

  • brookek004
  • TV/TS/CD, Straight Male
  • Age: 39

I am young and cool looking for a serious relationship

  • colonli088
  • TV/TS/CD, Straight Male
  • Age: 32

Hello everyone I'm Linda looking for longtime relationship

  • Sheila312
  • TV/TS/CD, Straight Male
  • Age: 62

I am originally from the east coast. Love Provincetown.

  • lisaedw721
  • TV/TS/CD, Straight Male
  • Age: 44

I’m a single mom hardworking, honest, loving, caring and straightforward

  • boldytoo
  • TV/TS/CD, Bisexual Male
  • Age: 46

dressing and meeting new people or a group that share the same interests Also really need help on makeup and hair styles... specifically contouring and highlighting... I know there are plenty of people to help me learn, I just can't find anyone out ..

  • Tbusinessman
  • TV/TS/CD, Straight Male
  • Age: 36

NOTE: I'M NOT INTO ALL THAT KINKY, DOMINATRIX, BDSM STUFF. PLZ LEAVE ME ALONE WTHAT. I'M THE MAN. I'M IN CHARGE, I'M NOT SUBMITTING TO ANY WOMAN. 2ND I LIKE CIS - WOMEN I'm a self made businessman, who spends a lot of time either at work, or at home..

  • CATADAM007
  • TV/TS/CD, Straight Male
  • Age: 39

Opening minded a real freak mad head skills creamy hole

  • Jeanette8693
  • TV/TS/CD, Straight Male
  • Age: 34

Looking for a long time relationship that will leads to marriage

  • YukioMustang
  • TV/TS/CD, Bisexual Male
  • Age: 24

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

  • puppet201Ar
  • TV/TS/CD, Straight Male
  • Age: 44

I am very headsonme person and cuite and outgoing and more

  • vatanika
  • TV/TS/CD, Straight Male
  • Age: 32

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

  • masnart65Columbus
  • TV/TS/CD, Straight Male
  • Age: 59

I'm Tammy Lynn 45**** a cup red hair super sexy love it all love to have fun meet new people and Friends

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

Hello I'm a 37yr old transguy looking 4 friends & more.

  • Anna01Dalton
  • TV/TS/CD, Bicurious Male
  • Age: 63

Athletic build, discrete, patient, open minded. Have been fantasizing about this for years.

  • viviantonyah
  • TV/TS/CD, Straight Male
  • Age: 59

I like and enjoy dressing in private. I enjoy taking pictures of myself. I enjoy dressing with other t-girls and cross dressers. I enjoy lingerie and having a man watch me. I always wear high heels and I love being a sissy slut and talk slutty. I onl..

  • missmiley69
  • TV/TS/CD, Straight Male
  • Age: 25

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 ..

  • KOMEANA
  • TV/TS/CD, Bisexual Male
  • Age: 47

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, . musi..

  • EdwinainchiOak
  • TV/TS/CD, Bicurious Male
  • Age: 62

Mature soft shaved CD looking for love very passionate and kind new to this. check me out.

  • EdwinainchiOakPark
  • TV/TS/CD, Bicurious Male
  • Age: 62

New into cross-dressing very fit very slim shaved very curious

  • tslyric37
  • TV/TS/CD, Bisexual Male
  • Age: 41

Couple looking for interesting fun with other down to earth couples.

Photos of real tv/ts profiles

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