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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

  • Sissieslut4Cock
  • TV/TS/CD, Bisexual Male
  • Age: 58

Looking for a connection with a girl who is willing to completely turn me into a girl with full feminization and sissfication training while taking videos of me while she is making me to pleasure very well hung and horny guys with both of my Sissie h..

  • slast30
  • TV/TS/CD, Straight Male
  • Age: 40

I'm 37 mtf TS woman pre-op. I'm open to trying new things. Looking for long term relationship.

  • dril972
  • TV/TS/CD, Straight Male
  • Age: 61

Looking for some interaction with other crossdressers, T-Girls, women and men that will take whatever steps necessary to make me the woman I was meant to be..

  • allca939
  • TV/TS/CD, Straight Male
  • Age: 50

Iam very opine mindied too and bottom and Iwill do any thing fore fun

  • alphaempowerd206
  • TV/TS/CD, Straight Male
  • Age: 58

Slim,size 4,160,30waist,5-9,7 thick.Clean,safe, nicely toned,stamina +! Open able , satisfy your needs and desires and I'm not sure how many more things I want to do!

  • julie6Chicago
  • TV/TS/CD, Straight Male
  • Age: 71

i love being a girl and suck your dick we then fuck each other

  • tracy4400
  • TV/TS/CD, Straight Male
  • Age: 48

I am looking for a female to hang out when I dressed up. I am not really interested in a sexual relationship. My fantasy would be to go with a girl who is pretending to be guy while I am dressed as girl. I am 5'3" without heels. Lol!!

  • iroczChar629
  • TV/TS/CD, Straight Male
  • Age: 78

For a couple to let me entertain them! Sucking, FUCKING, oral and ANAL, and toys!

  • styerjess414
  • TV/TS/CD, Straight Male
  • Age: 36

You can text me on my number any time nice meeting you

  • jennadavid026
  • TV/TS/CD, Straight Male
  • Age: 44

Just want to be myself whoever that is exploring who I am

  • BrownSugar57
  • TV/TS/CD, Straight Male
  • Age: 67

To have excellent missionary sex with a lot of foreplay. To wrap my legs around his butt sometimes as we stroke and explore all fantasies. Black CD 5"11 Average discrete, safe, excellent shape male, dress only behind doors now.

  • rprs874
  • TV/TS/CD, Straight Male
  • Age: 51

I'm 5 9 slim smooth and 150lbs kinky and vers and love anal play

  • Crystal2800
  • TV/TS/CD, Bisexual Male
  • Age: 33

I'm a sissy who would love to meet some black men to have fun with

  • kylieus344
  • TV/TS/CD, Straight Male
  • Age: 30

I'm looking for some fun and new experience here and meetups. Still exploring in shape and attractive.

  • Caprimoon75
  • TV/TS/CD, Bisexual Male
  • Age: 21

All my life I've had a thing for big bellies and burping. I don't know why, I just have. Not looking for sex, just someone who needs their belly worshipped while they burp in my face. Message me and I'll send you a picture of me. Not into farts.

  • trowbridgek956
  • TV/TS/CD, Straight Male
  • Age: 33

I am looking for women that want to dress me up as a woman. And have fun chatting as girls.

  • Gina2BE21
  • TV/TS/CD, Straight Male
  • Age: 57

Would love to meet, get dressed and go out and party!

  • riverstyx
  • TV/TS/CD, Bisexual Male
  • Age: 28

I’m bookish, love a good conversation, and love feeling useful. I’m looking for fun, safe hookups. (theythem)

  • radioh641
  • TV/TS/CD, Straight Male
  • Age: 68

Never had the guts to get my dream for it up my butt

  • isaacsactualem310
  • TV/TS/CD, Straight Male
  • Age: 26

Im an artist! I love trying new kinks and im a masochist

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

I’m career focus always working while putting education first and maintaining my business as a hair stylist. I’m looking for someone to get to know grow build , no rush baby steps

  • mikedamicolove69
  • TV/TS/CD, Straight Male
  • Age: 69

Long term fwb who loves cross dressers to date weekday nights.

  • girlwonder2
  • TV/TS/CD, Straight Male
  • Age: 22

I’m a cute sub and would let you do just about anything to me that you’d want ;)

  • stevenlspace216
  • TV/TS/CD, Straight Male
  • Age: 72

just dress up fun especially with high heels and stockings

  • Ink843
  • TV/TS/CD, Straight Male
  • Age: 54

I like the fact shemales have the best of both worlds

Photos of real tv/ts profiles

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