Chicago, Illinois Sex Ads and Adult Classifieds

Chicago, Illinois sex ads and adult classified listings. Select your location below to find adult dating hookups near you. Browse our listings of straight, gay and lesbian dating ads along with trans and swingers classifieds. Many advertisers desire no strings hookups. Others seek occasional or longer term dating arrangements. Search or post for free in BonePage sex classifieds!

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  • August 6th, 2026
  • ShopinRound38 outgoing, funny, and independent (Please only message me if you live within 50 miles of the Chicago area) . I am winding my career down and am wanting to traveling more and work less. Looking for someone to share intimacy and good times with. It’s getting harder and harder to find someone the old fashion way, so thought ...
  • Amazonian Warrior princess looking for her Xena Tall Woman for Woman in Chicago I'm a soft butch bisexual/pansexual woman. I enjoy cosplay and RPG. You wanna role play with me? My name is Terri and I am 5' 11", medium/athletic build and I have long dark hair. I am fit and muscular from working out regularly. I'm interested in all types of women ...
  • PeeWee's Looking for a BIG Adventure! Hi, I'm Herman, and me and my little friend are looking for some excitement in Chicago tonight. If you are up for an adventure we are too! We aren't too picky, just hope you like Tequila and dancing. Please be motherly and kind. Can you come out and play?. If so click here to come out and see u...
  • European Lady seeks sensual gentleman European Lady in Chicago My name is Karena and would like to meet a kind gentleman for dinner and dating. I am mature and I originate from Europe and moved here recently. Serious callers only and I am willing to please you.  Check my website pics and contact info KarenaXX86...
  • Age 47 Regular Guy with a Lot to Offer!! Man Seeking Woman for Dates in Chicago Hey, Richard here. I just want to say hi to you and hope you might check out my profile and see if you want to go out for a date. I am just a regular guy looking for a regular gal. I've been single too long. I keep busy and have a great life but It's time to m...
  • Lesbian Bombshell - Open Minded in Chicago W4W in Chicago My name is Brooke, age 21 and I am lesbian, open minded and loving. Please message @Brooke4FemXXX with your recent photos for mine. Let's exchange info and meet up to see how things go.  Username: @Brooke4FemXXXLocation: Chicago, IllinoisAge: 21Gender: FemalePhotos: 36Vide...
  • Want to touch my amazing... Wookie? Me, black gay male seeking local men to date, hang with and have some good times. Up for pretty much anything. (love body rubs) 5'10, green/blue eyes, 30 yrs old, well endowed and always ready if you know what I mean.  lived in Chicago for most of my life. I am a city worker so a l...
  • Asian Beauty likes a nice massage My name is Aiko and I am from Japan. I like to meet a girl who likes massage to give and receive. I am attractive and sensual. I want to meet you. I am shy at first but very willing. Please message me online for my photos and more information.  Kisses πŸ‘„ AikoFemme Username: @Aik...
  • Karaoke queen loves singing with her Knight-ess Carmel Karaoke Queen in Chicago You love to sing karaoke? Good!! Me too!! My name is Carmel and I adore singing. I am not shamed to say I am probably not so good but after a drink or two you probably won't care! I love singing modern pop, 60's and 70's disco, and even some modern rap. Message me wi...
  • Hot New Chicago SexBook Member Profiles Added Daily! Meet Chicago Babes for NSA There are over 5,300 sexy women near you seeking NSA hookups in Chicagoland. Visit the world's biggest and most active adult hookup site and get luck tonight! Women are in need of more men right now! These girls want to have fun and maybe even ongoing FWB with someone jus...
  • Spanish Gay Man Needs New Owner... Hi, I'm Shaggy a sub from Madrid, Spain originally and just moved to Chicago about 5 years ago. My English is good, I'm 32 years old, 5'9, 170 pounds, very skilled in bed and very passionate. I need someone to own me, take me, use me and protect me if only for a short time. What do you say amigos? I...
  • Chocolate Mocha Trans Lady Needs That Sweet Vanilla Tonight!... Hey all my sexy Chicago boos I'm Letta a black trans girl seeking a white male in Chicago for some sexy and passionate one on one action. If you are new to the t-girl scene don't be afraid baby. I'll surely take good care of you and rock you nice and gentle for at least the first 5 minutes! I can't ...
  • FtM seeking Princess Bride in Chicago FtM seeking Woman in Chicago Hi, I'm Andy, age 33, FtM mixed-race transgender man living in Chicago. Also, you must love that movie! If you don't get the reference you can still message me anyway! I love that movie and I will watch it with you over and again. View my pics and send me a message...
  • Not exactly out yet. Need discreet NSA... Mixed mexican/white male 29yrs, professional divorced with two kids. I am looking to explore my bi-sexual curiousity in the Chicago area with the right man and see if there is anything there. If you can be discreet and are interested then please come see me by clicking here....
  • Cute Barista Seeking a Fun Regular β˜•πŸ’‹ I'm not really sure how I ended up at this coffee shop, but there you have it. Maybe I needed a break from my trusty at home coffee maker, or maybe I'm still looking for my soul mate barista - you know the guy that actually remembers your coffee order and makes eye contact as they hand it to you, an...
  • Ebony Street King Looking for a Real One πŸ–€πŸ”₯ About me Confident Black Man with street edge look. My friends say that initially everyone notices my looks and all that because of my height, muscles and deep voice but when you actually speak to me, you soon see that there is so much more to me. Friendly, open and the most honest person you could ...
  • Intoxicating-Stacked Blonde Beauty in Chicago... Hello men, I am Korina a single woman seeking a single sexy man for NSA relations in Chicago. About me: Russian born, 25 years old, 5'7, 130 pounds, 38D cups have been here for 10 years and have a small business. Do you live in Chicago? I try different places for finding attractive sexy men, but not...
  • Tall, Dark, Handsome Lesbian My name is Selena and I am tall, dark haired, in my 40s and still in my sexual prime! I have Latin heritage and I am fiery but kind. I do not have a bad temper but I am passionate. Age doesn't matter as much as personality and spirit. Any race, any height/weight. I love all body types as long as you...
  • The One and Only - Chi-town's Own - Chocolate Delight Tonight! Get Some Ebony Sweetness C'mon now every lesbian woman loves Chocolate Delight! I'm decadent, sweet, petite and good enough to eat baby! I'm an English/Social Studies teacher here in Chicago and love what I do, but need my batteries recharged from time to time if you know what I mean.  I don'...
  • TS Sugar Baby πŸ’Ž Femme, Flirty & Looking for the Right Man in Chicago I’m a transgender sugar baby who loves femininity, attention, and being appreciated by a confident man who knows exactly what he wants.. Confidence speaks louder than words. Gentle touches matter more than grand gestures ever could. Let's Link Up Babe - Fond of the sugar dynamic. Getting pamp...
  • Flirty Fun, Endless Kisses & No Judgments πŸ’‹ Chicago  The person I am today is a relaxed yet passionate man who balances his gentlemanly nature with  flirtatious tendencies by sending sweet messages during mornings and provocative messages at night. 😈 I enjoy tasty  food with slow kisses and unexpected plans that typically lead to in...
  • πŸ”₯ Confident Woman Into Pegging πŸ”₯ W4M Dominant Dating Energy 😈 Are strong women a turn on? Good. I’m a pegging-friendly dominant woman seeking man who wants to experience role reversal, trust and playful submission. If you’re looking for some W4M fetish dating, female led relationship, pegging curious man, dominant w...
  • OKAY I Admit It! I'm Feeling a Little Frisky in Chicago Where's My Boy Toy in Chicago Ramona, 22 years old here in Chicago and in need of some male company. I have an itch that only you can scratch. Hmmm, what do I want cause you guys come in all kinds of flavors and sizes. It's like being a kid in a big candy store. I know, why don't you tell me what f...
  • Let's Play Cock, Paper, Scissors!... Gay Man Looking for Fun in Chicago Now that I got your attention. Hi I'm Graham, a gay man here in Chicago and I'm looking for a man who likes to play sexually charged games. I'm 28 years old, black hair, brown eyes, 6'0, well endowed, (8+inches) hispanic, single, love to party, no pets, ...
  • Exotic TS Beauty Seeking a Generous Gentleman πŸ”₯πŸ’Ž Hello lovely, I’m a beautiful trans girl with lots of curves. I’m a confident woman with a beautiful personality. Here I want to meet with the more successful men. Men who can understand that the beauty is also of the feminine kind. Intelligent men, that can realize that we trans girls a...
  • Nerdy Guy Seeking a Cute Dude πŸ€“πŸ’¬ A bit of background I'm usually quite pretty much invisible, but I'll be a bit more noticeable once I'm awake. Tech kind of person among a few other things. Self-proclaimed self-styled pop culture geek and obsessive love of cinema and video games. Wide awake at late hours of the night having empty c...
  • Looking 4 a Man 4 Sex πŸ†πŸ’¦ & Fun😍🀩 I really need to get out and have some fun, maybe a drink, smoke.. Sex -  Message Me❀️ I've been really horny and just stuck at home. I have a few GF's who might want to join us and play too, if you're down Or I'm willing to go out and have fun just us. Will you help me get out and have so...
  • Hey Sexy I'm Gonna Add YOU to My Cart! Shopping Hard in Chicago Hi there I'm Roseanne about 22 years, about 5'5 and brunette with big brown eyes here in Chicago. You know girls love to shop online and I'm no different. I'll just add you to my cart and check you out. Now how long until delivery? Huh? I don't do snail mail, so make it qui...
  • SWINGERS SEX NETWORK Locals Join Free! LOCAL SWINGERS FORUM Swingers, Swaps, Threesomes, Groups & Sex Clubs! Local Swingers | Pic Exchange | Sext with Members  1. Signup Free for instant access2. Chat up hot locals & swap pics 3. Arrange local swing hookups!   KenNKat:&...
  • Successful Sex Genius! Clever Lesbian in Chicago Inventor of the Hindlick Manuever, Jodi here in Chicago. I have impressive credentials such as a sexy vibe, perky tits, great complexion, 24 yrs old, blonde hair, blue eyes, 5'6, 120 pounds, dirty mind, love oral and toys, love kink and fetish, and open minded. You co...
  • Princess Mai Rules Chicago! Cruel to be Kind in Chicago Come bow down before Princess Mai of Chicago and I will rule over you. I will control your life, your comings and goings, and who you can or can't talk to you sneaky little bitch! When I text you better answer and be at my service. It is your duty and pleasure to appease...
  • Don't ever play leap frog with unicorns! Hi I'm Claire, a cougar here in Chicago to show young men that with age comes wisdom like in the headline above. lol I am willing to share my acquired knowledge with eager cubs who want to be shown a better way. Of course most of the knowledge I have would be sexual in nature since that is why I'm h...
  • Phat Booty Lesbian Soul Sister Shakin' it in Chicago Baby!... Hi I'm Lisa a Black BBW lesbian looking for a hot woman in Chicago. Hmm let's see do I want some chocolate, mocha or sweet vanilla tonight? I cant decide! Why don't you get hold of me and help me decide and show me what's up? I'm down for a hookup or maybe a girlfriend long term, we'll see. Please l...
  • Young Female in Chicago is Curious... Chicago Bi-curious Babe I'm Darlene, 26 living here in Chicago all my life and am finding myself bi-curious. I've always wondered what it must be like to be with a woman. I see women who are hot all the time and have certain sexual feelings for them, but I never acted on it. Except maybe a few time...
  • Looking for the bride of my dreams Chicago Contractor Seeks Wife This is Erik and I am a local resident and own a contracting business. I love distressed property rehab and I'm always looking for rehab projects. I am looking for a bright intelligent woman who can make me smile. When not working, I love the outdoors and I am an avid ...
  • Czech Beauty new in Chicago Ahoj, lásko. Rád bych se s vámi setkal a hledal jsem vás. Kdy se s tebou m?ΕΎu setkat? Jsi tam venku? Kontaktujte m?. Hello, my love. I know you are out there somewhere. I would like to meet you and have been looking for you.  I like texting and sharing sexy thought...
  • Looking for my sexy ride or die man Hi gents, Gina here I'm a tatted 26 year old biker chick at heart who is into more mature men, and I live by the biker's code. I am loyal, love the feel and freedom of riding and always give my road king the sex, affection, attention and space he needs. Take me for a ride sometime? A good ride alway...
  • I Need a Sexy Man to Tame Wild Willy! Hung Chicago Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Chicago with a big wild willy that always seems act out in inappropriate ways at the worst times. For instance I'll be relaxed, minding my own business at my favorite Starbucks and see a ...
  • Come Join US!!!! SWINGERS DOWN FOR ANYTHING AT ALL! 😘πŸ”₯ Chicago πŸ’‹ Hello babess... I'm Roxxxy and my Hubby's name is Johnny. We're from J. My hubby and I are a very sexy and adventuruous swinging couple who love to explore our  deepest and nastiest fantasies.. We MUST indulge in the thrill of wife swaps and threesomes. The swingers lifestyle has brought so muc...
  • Hot trans chick with nice boobs Hot trans chick in Chicago. Sheila wants to meet you. Hey guys, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, well endowed and functional, top or bottom. I love oral sex giving, receiving or 69. Want to explore kinks? Me too!! Want to...
  • Earth Momma - Strict Vagitarian... Hi I'm Orla, 29 years old, sort of a new age type lesbian in Chicago looking for a compatible woman who I can share nature's bounty and goodness with. If I start boring you with my star charts, crystals, palm reading or alien theories just shove something yummy and lickable in my mouth. That always ...
  • Tiffany Shelle - Your Chicago Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Chicago It’s Tiffany Shelle your perfect tranny girlfriend πŸ₯° πŸ’• SAFEπŸ’• πŸ’― LEGIT βœ¨πŸ’ž SKILLED, Exotic and Erotic πŸ’¦ πŸ₯° I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% functionin...
  • SEPARATED MOM 🧸 Seeking NSA Hookups in Chicago Separated mom for sex hookup in the Chicago area This is my first time trying adult classifieds. I'm pretty shy at first but I open up quickly after getting to know someone. I have an active imagination and fantasy life. I'm a kinky, naughty girl 😈 looking for some hot fun to let off this sexual...
  • Young, Free and Single but I want to be with Mr. Right. You have got be out there somewhere! I am lonely and I would love to find a funny and happy-go-lucky guy who can be my best friend and lover. I'm hoping you look good in a cowboy hat and jeans! Send me a text to @LonelyinChicago so we can get familiar!  LonelyinChicago...
  • Don't Worry I Bite! Feisty redhead trans in Chicago full of fun and loves it rough on the bottom. I'm 5'9, 170 pounds, 32 years old, well endowed, fully functional, passible and hot to trot. You can take me anywhere, but I can't promise to always behave. I have a dirty mind and when the urge hits it's hard to control m...
  • your place or ours? 🏠 SWINGERS SEEKING SEX PARTNERS in Chicago😘 Hey there, I'm Judie from Chicago. My husband and I are a fun-loving swinging couple who love to explore our fantasies and indulge in the playful side of life. We adore the thrill of wife swaps, threesomes, and all the excitement that comes with the swing lifestyle. View our nudes!What I love m...
  • Hot and kinky MILF looking for some fun in Chicago Chicago MILF For Kinky Hookup! Hi all you sexy Chicago guys, I Georgia and I am an slightly off beat working professional mom of two. MILF. Just looking for some sexy fun and to explore my (and yours?) kinks and fantasies, FWB. I am into men, but possibly women or even a hot couple depending o...
  • Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Chicago? Hey, I am Jasmin, with a great body and busty. Hit me up @SweetJasminT. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for a fun date and see where it goes! I'm preop and functional, very sex positive and love all sorts ...
  • Ohhh Yeah! I'm PHAT AS HELL BABY!!! BBW Wants FWB in Chicago LustyPhatty (Susan) here livin' large in Chicago. I know you are cravin' my curves and big playful funbags, and I got a few cravin's of my own. I want you to play with and massage my huge titties all night. (heaven) I'm a BBW 34, 5'3, 42EE cup, and will tell you the re...
  • Looking for a Smooth Operator in Chicago... Let's See How You Operate! Hi all I'm Arlene a busy surgical nurse here in Chicago looking for a guy who is smooth like Southern Comfort. Not brash and overly cocky and overly sure of himself. I need that silent strong masculine energy in my life that tells me I'm a woman and makes me glad to be so...