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.
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Part time sissy - Part time studentHey :) 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 .. |
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love to wear my skintight outfits and tuck,most times I feel like I am in a woman's body, ..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.. |
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mature CD looking for love in ChicagoMature soft shaved CD looking for love very passionate and kind new to this. check me out. |
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Edwina crossdresser from ChicagoNew into cross-dressing very fit very slim shaved very curious |
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Post Op transexual looking forPost Op transsexual easy going and loves to have fun. I respect myself and others. Don't care for rude people. I'm a lover not a fighter. |
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Plus size sissy looking to have my hole filledI'm a plus sized inexperienced sissy looking for a mistress to train my sissy pussy |
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Seeking a variety of friends in my areaActive, friendly and outgoing Cali transplant new to ChiTown as of last year |
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Latino male, 38 yrs old, 6"1 , 215 lbs , 8 inch hard and thickLooking for someone to have a great time with and experience life |
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Am here for serious relationshipI believe in getting to know someone first because that's how friendship is built. Friendship is built from a strong foundation first and then it continues to grow from there |
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CD Looking to Meet other CD FriendsHi, I'm Ginny. CD looking to meet like minded CD's for friendship and more. |
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Bubble butt sissy needs black daddyCurvy health concious sissy into working out, cooking, fishing, travel, love dressing up, and modeling for pics. Need black daddy for long term. I am very masculine in public, but in private I am a total submissive fem. I need a black daddy who can g.. |
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Hello im Jennifer just exploringIm a crossdresser who loves lingerie and to dance!. |
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Veronica looking for fun cross dressers or menI’m 42 and love to dress up. I’m a closet CD and looking for fun |
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Part time CD looking for discreet funPart time CD looking for discreet fun. Bisexual and open minded |
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Edwina in Chicago looking for other crossdressersNew crossdresser looki seeng for others completely shaven an extremely good shape very feminine. I'm a bottom. But also versatile. Let's just talk I'm ready for anything |
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Please take me shopping with you.I like to wear ladies clothes. I do not like men. Genetic girls only. |
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Looking for the right girl to spend quality time withI want to express my self with another girl and live out our fanticies |
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Panty worshipper needs her panty punishmentLove to dress up. . love to have my panty covered ass punished, fucked, spanked , ect. . ! ! ! |
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Looking for a good time. Latino maleI am a 45 year old latino male 6"1 in height 215 lbs and 8 inch cock |
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Looking to meet those who appreciate a Real Woman!Fun love, full time femmine girl who Loves dating men |
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A free spirit, a free mind. Just here to have some fun meet some people, see what happens...Just here to have some fun meet some people, see what happens. I life is too short to not have what you want so get what you want when you want it. |
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Looking for open minded couplesCouple looking for interesting fun with other down to earth couples. |
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vivian loves cross dressing and sissy slut playI 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.. |
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hit me up and im looking for local hookuphey there im Alison 27 single im new in this online dating site im looking for fun and local hook up meet new friends and of course love and fun and serious relationship if you are interested to me feel free to hit me,, is that u? or text me |
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Sexy CD looking for fun and pleasureI'm a new CD looking for someone to play with and be your little sissy |
