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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Hey im looking for hookups andor feminizationIm tall and skinny 33-year-old black hair hazel eyes |
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Its me the girl u would want toIm sexy and very sexual love to please and keep my man satisfied and toes curled |
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Girly girl looking to meet others :)Hi :) I’m 25 live in Chicago and would love to chat and meet others |
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Just a crossdresser that's into almost everything heheLiving in Chicago, part time cd, possibly becoming full time |
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Humble, submissive and loyalVery romantic submissive type of man , loyal and strong |
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i am a single guy looking for a serious and honest relationshipMy name is Jim Wallace, i'm 42 years,i am separated and single, i'm waiting for my dream woman and i believe when i have a woman that is honest and caring,that she wouldn't hurt my feelings, I am 5"9 and 185lbs. You care to know more? |
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I'm Interested In Meeting A Nice GuyFirst I Wanna Start By Saying Not Judging What Your Preference Is Me Personally I'm Not Here To Meet And Have Sex With Different Random Guys, What I Am Interested In Is Meeting Someone On Friendship Level And See Where Things Go. I Would Like To Hear From You |
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Chicagostan TS Looking For Others...I am Krystanna, a pre-op male to female transsexual. I am interested in all aspects of transformation, and an erotic enjoyment of each stage as it progresses. I am a switch, and interested primarily in a dominant male to female transsexualtransgen der individual, women, and possibly men. I am into many fetishes, including rubber, latex and leather clothing, a vast spectrum of sexual activities, especially CBT. |
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Looking for a great person to snuggleI'm Bailey. Born and raised in Wisconsin. I love to disc golf read spy novels and shoot porn. I like to crack jokes and break up confrontations. I hate drama unless it's in a movie. |
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I'm 29 years old, living in the Chicago region.I'm 29 years old, living in the Chicago region. I'm interested in meeting a man aged between 26 and 78. |
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Out here to express and enjoy my fantasies.Hello there! I'm Ann a confident and compassionate individual who believes in embracing life to the fullest. I identify as transgender, and my journey has shaped me into someone who values authenticity, resilience, and genuine connections. |
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i hope this just another good place to meet upi new here and would like to share my little secret |
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I'm just a good girl with bad habits ❤️I'm Lingerie lover! I love all things sexy looking to meet like minded girls! |
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Cute and curvy with thick legs and a big assLooking for a real man...don't be shy...come see what these lips can do |
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cd looking to meet another closet cdlong time closet cd looking to meet someone who is the same |
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Very much into lingerie glamdressing!Looking to meet and chat share with like minded gurls |
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I am a little shy but love all things feminine.Would love for a sext CD or couple to ravage me...lol. I am not new to crossdressing but I am new to sex while dressed. I have a passion for nylons and women will always be my first preference but I am expanding sexual horizons to include a crossdresser or two . I just adore feminine clothing and pretty sure I am bottom. Looking forward to chatting and who knows . Would definitely want to start with a girl that isn't well endowed... I am a Virgin. |
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I am a 78 year old Preop Renaissance Woman looking for a relationship with a lesbian woman. I was married for 44 years and came out the day after her death. I live alone In Edgewater.I am very active in the Chicago Queer Community. I love traveling, theater, dining, the ares of all kind. I am looking for someone to share intimacies. |
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Looking for tops only must drive and work and live aloneSexy trans bottom who will blow your mind Love to travel. Enjoy going out clubbing or a night on the town for drinks or cuddle and watch movies |
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I'm a forever gender fluid T Girl.I enjoy the company of like minded Attractive "Girls" |
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Very open and chill. Down to party and have fun.I’m very chill and love to have a good time by all means. Looking for chill people too |
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Looking for regular relations. I love dress up as a girl and by treat this way.Welcome to my website. I love sex and I am bisexual. I love dressing up as a girl. High heels and stockings are my obsession. As soon as I dress up as a girl, I live in a different world. I am powerless and submissive. I'm turned on by tall men. Then I'm a little helpless girl. I enjoy it and feel good about it. Sometimes I think about a threesome. Such a digression. But if you are looking for a great girl, I can be at your disposal. You must respect me and treat me as your property. I will always be faithful and obedient to you. I will always dress nicely for you and adjust my makeup and nails to make you happy with me. I'll even dye my hair any color you want. I'm looking for a man who will treat me like his personal toy. My dream is to have a tall man. 6'4". But it's just a dream. Everyone has a chance. If you don't have a photo and you don't want to show it, there's no chance. I always welcome all CDs and TV. I love women. I dream of a lover who will tolerate and own me. |
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Im 19 Down to try almost anything at least once Just trying to explore and learn but if something ends up coming from this I’m not going to be madI’m new to all this so I need people to be patient and willing to educate |
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Hello, Lets talk about what we want!Looking for someone nearby Available most times with notice |
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Chicago pre-op trans woman seeks women only that are genuinely dominant. I don't want to get into my kinks or dak desires. I don't think I naturally submissive but crave being under the control of a woman that ENJOYS being in charge.I live openly as a trans woman.. So please don't refer to me as a man or a crossdresser. I have many fetish interests, sissy attire, old fashion foundation garments, Bondage, over the knee spanking, humiliation, especially mental ...but that is something that we can discuss at the appropriate time. LET me be very clear .. I am seeking a genuine relationship..I am not interested in sessions or pro d0ms.There is nothing wrong about making a living ... however it is not what what I want...So far it appears to be the only thing available |
