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.
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Simply Beautiful Trans FilipinaFun, friendly, charming sweet |
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Help my wife turn me in to the cock lusting slut i desire to beMarried bi cd wife very willing to please me she agreed to help me fullfill ally fantisy and lustfull desires |
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FreakySex any where, any time!I LOVE sex! Anyway, anytime! My boyfriend and I love to go to sex and swingers Clubs. He likes to watch me with other women.. He loves his arse rocked. |
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With God all things are possibleCool,loving,caring God fearing I love to meet people ,travel explor |
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I'm a closet boot lover and would be interested in possibly hooking up with someone who shares a complimentary interest.Shiny patent leather or pvc single sole stiletto Boots excites me to no end. To be honest, I don't think I could refuse to give in to anyone wearing a pair of shiny stiletto boots and told me to get on my hands and knees and kiss their Boots no matter where we were. Good honest fun people make me happy. |
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I am a person with many interests, specifically in the art department.I loove cats! I have two — a black one and one that’s gray with white socks. |
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I’m feminine, girly, sexy and hormones have made me crave men. As a girly sissy,my goals are to be a pleaser with my mind and body.I love exploring my femininity. Be it smelling flowers or feeling satin undies. I love being a woman. |
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Looking for some fun. Very new to this, please work with me here… Lol.I like to joke around, but also know when to be serious. I like having mutual conversations. |
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Fantasy Girl thick short soft smooth sexy submissive bottom crossdresser ready to be owned and controlledWhat excite me is a rough aggressive dominating controlling daddy I'm into older heavy set men are a plus, the meaner the daddy the happier the baby |
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Heyo! Names Bear. I'm a female to male transgender puppy looking to start dating!What's gets me excited? I'm not really sure. What makes me happy? Someone that enjoys pizza!! |
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Just being honest, I'm new to this. So please be gentle? I guess.I'll usually be all smiles or occasionally if I feel truly comfortable I can be a bit of a brat. Idk tho |
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Hey I’m new to crossdressing I’m looking for a big man to tak the shyness away from me and make me a submissive slut I prefer black menI'm 28 years old, living in the Chicago region. I'm interested in meeting a man aged between 29 and 57. |
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Ready to fuck all trans thickI love trans they are perfect they do no wrong in my eyes |
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Asian Crossdresser，BD SM，Anal，Enema，e tcFantasies of being tied upspankedstabbed in ass etc makes me horny. Hope to find someone to play with. |
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I raise in 60 generations instead of peace and Love I am looking to explore the more kinky side now I am told I will come extremely much if I can find the r right woman to dominate me allI like building that social bound such as kissing foreplay building a social bond |
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Just a lovely trying to live a good lifeHello there it's Olivia just a normal girl trinmg to be happy |
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Sissy Sub looking for trainingI’m looking for a dom to sissify me. I want to submit to an alpha male |
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Trans soul exploring the dynamics of this world! Seeking open-minded and genuine connectionsA confident trans individual on a journey of self discovery within the captivating world of BDSM. As I embrace my authenticity, I’m excited to connect with open-minded souls who appreciate the beauty of consent, communication, and shared desires. Whether it’s exploring new dimensions of pleasure or building connections founded on trust, let’s embark on this adventure together :) |
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hi love to meet with cd's and geto know themwant to dress in lingerie and cuddle adore nylons and girdles |
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partnered polybrsub who's looking to be topped try bdsm things withI'm 18 years old, living in the Chicago region. I'm interested in meeting a transgender person aged between 18 and 30. |
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I'm looking for a fuck buddy in Chicago. I'm a nonpassable crossdresser.I'm a private crossdresser and I keep it to myself. I wear tights and pantyhose all the time and I might have on a pair of sexy panties to go with them. I only wear the clothes and shoes, but Im willing to try makeup and wigs |
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I’m trying new thing out… I know some rules and willing to try almost! Everything… but yeah I’m here to have fun!!!Well… I like clean cut orders, edging overstimulation, and ruined orgasms are fun, I like to bottom and sub mainly because I tend to be sadistic when I top… |
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I am here for your cock. I love to be fucked by as many dicks as possible. I like two cocks in my ass. I'm willing to meet up or face time.I love lingerie and big cocks. I will do pretty much anything you ask. |
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CD who loves all things girly. Love to chat with other gurls!Dressing up and being feminine. I love makeup, nail polish and being girly. |
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Subby into feminization and promiscuityNot sure what to put here yet. Give me a little time to think about it |
