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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  • November 6th, 2026
  • 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...
  • Redwingz Looking for Princess Charming Chicago Lesbian For Fun Hi I'm Lucy (Redwingz) here in Chicago looking for a sexy partner who isn't scared to have a little fun. I like the outdoors, walks in the park, the beach, camping, fishing, DIY projects, motorcycle rides and lots of affection. Open to trying new things. To get hold of me re...
  • Hey all my chubby chasin Chicago boos - check out this thick phat booty!!! Tracy here, BBW, 24 years old, 40DD cups, phat as hell, inviting thighs and a big ass booty! Looking for a sexy man who loves big girls. (BBWs) Must live in Chicago or at least no further than Aurora or Elgin or Gary and must have a car. I don't want any long distance relationships, I'm looking for ...
  • INSTANT BANG BUDDIES - Free - Anonymous - Verified Pics INSTANT BANG BUDDIES! Get Your Freak On with Local Bang Buddies   Local Pics / Upload Your Pics SPECIAL: JOIN FREE FOR INSTANT ACCESS! Upload Your Hot Pics Browse Local Hotties Hookup with local bang buddies Signup Free Instant Access! How Many Bang Buddies Are Available In...
  • Bring a toy for Kitty (w/batteries) on our first date!... I'm a bit of a goth and have recently discovered the magic of toys. Bring your favorite toy on our first date and I'll bring mine. This could be our Toy Story. Lesbian in Chicago seeks female companion for erotic encounters and possibly long term relationship. I'm Katzzy and am 33 years old, 5'7, 15...
  • 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 ...
  • 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...
  • Fun Loving Couple in Chicago Seeks Male or Female for Threesomes... Swingers in Chicago Seeks Partner Hi, we are Jordan and Riley, a sort of a younger swinger couple in Chicago looking to explore threesomes with the right guy or girl who is open to sex with a man and a woman at the same time. We look forward to experimenting with some wild fantasies we have and wel...
  • Selena Trans girl cute looking for love Hello boys. I am looking for love. You want meet me? I want meet you too! See my pictures @SelenaIsTrans and send me a message to set up a date. I like going out for food or drinks, having a great time and I especially like great sex! I am preop and can do top or bottom though I kind of prefer top ...
  • Attractive, Dark haired and Slender - Brunette28XChicago Hi, thanks for checking out my classified! I am tall, slender with dark hair and deep brown eyes. My interests include running, hiking, biking and horse riding. I am an account manager and I have just moved here. I am looking for local friends with a view to dating and possibly more. I will add mor...
  • Sexy Honey I am a totally real, down to earth, fun girl! I am looking for open-minded, playful, sweet, tender, fun guy to make me laugh! SEXXXYHONEY Call or PM   Message me and send your recent pic for mine Talk on phone required first before meeting in person No strings...
  • 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...
  • I'm Danish... Eat ME! Been dating most of my life and nothing too serious, but now I'm ready to settle down with the right person. I'm looking for a woman who will complement me. Where I have weaknesses she will have strengths. She must be local in or near Chicago, because I did a long distance relationship once and...
  • Small, smooth body big heart Smooth 19 years old in Chicago Hey guys, I am Jon and I am 19 years old, smooth, slight build but fit. I like to do karaoke, dance and travel. I love to explore the male body and enjoy sex anytime, anywhere! I'm a passionate and attentive bottom only plus I can cook a great meal! Check out my profi...
  • Sexy Sissy Twink Wants to Get Rekt by Power Top Man! Drive it home rough and real hard big boy! I'm Harris a 23 year old twink sissy, Aries, 5'7, 140 pounds, blue eyes dark hair, tight ass who loves alpa type gay men and bisexuals. Please have stamina, strong controlling hands to hold me and help thrust harder. Let me know if you live in the Chicago a...
  • ๐Ÿ–ค Inked Emo Girl Seeking Man ๐Ÿ”ฅ ๐Ÿ–ค๐Ÿ–คEMO Girlie in Chicago๐Ÿ–ค๐Ÿ–ค Dark circles under my eyes from being woken up at the last minute to try and get my eyeliner on point, lipstick that gets wiped away to the bottom of my chin and a mind that never ever switches off. The constant juggle to keep my mouth closed and my mouth off. Y...
  • ๐ŸŒŸ Handsome JOHN Seeking a Spark ๐ŸŒŸ LET'S PLAY SOME Hello there, lovely ladies of Chicago! My name is Johann and I am on the lookout for that special someone who can ignite a fire in my heart. ๐Ÿ’–Swap pics & contact info I have a passion for exploring the great outdoors, whether it's hiking through the mountains or relaxing by the lake. ๏ฟฝ...
  • ๐Ÿ’”๐Ÿน Fresh Start.. Just Out of Relationship, Need a Fun Night Username: @MeganAfterDark Private Meetups: YesPhone Chat: YesVideo Chat: YesPics Available: 17 Chill and have a good time? Message me. ๐Ÿ’ฌ๐Ÿ˜‰ Megan here from Chicago ๐Ÿ’•recently went through a break up and is looking to get out of the house and release some tension. She is looking to meet a re...
  • Italian single girl looking for love Ciao amore mio! Sono nel mercato per trovare un bell'uomo muscoloso e carino. Se sei carino e in forma mandami un testo per una data! (AngelicaXOXO) Hello, my love! I am in the market for finding a handsome man who is muscular and cute. If you are cute and fit send me a text for a date! (Angel...
  • ๐Ÿ’œ Cute TS Girl Looking for the Right Guy ๐Ÿ˜˜ Just moved to Chicago๐Ÿ˜Š Gorgeous, very sweet and easy to get to know. I am a trans girl seeking to meet men that are confident and know what they are looking for, yet are also looking for some friendship with a new person. I enjoy going out for cocktails and having a good time, flirting with the g...
  • Flawlessly gorgeous trans bombshell in Chicago Trans MtF for Man in Chicago I transitioned 6 years ago at the age of 18. I'm still fully functional but live 24/7 as a female. I pass flawlessly so let's go out on the town! I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am short and cute and I have bedroom e...
  • Smokin' Hot and ready for a date! Ok, so maybe Smokin' hot is something you need to decide, buy hey, I have a sense of humor! Seriously though, I do think I am quite attractive and I have certainly been complimented often. My hair, especially, gets a lot of attention because it goes way down my back and I sit on it! It is long and s...
  • Chicago BDSM Master Taking on New Trans Slaves... I am single minded strict, controlling discipline oriented Master in the Chicago area seeking a devoted sub/slave to satisfy all of my whims. I will break you in with proper training protocols starting with, corporal punishment, all kinds of Humiliation, hucow, whips, gags, eletro, medical and much ...
  • ๐Ÿ’‹ Naughty or Nice? I Can Be Both ๐Ÿ˜ˆ KINKY BDSM W4W Woman Seeking a sexy lady in Chicago... I want to know your KINKS๐Ÿ’ฏ๐Ÿ˜ˆ I'm really into fantasy play and BDSM. I love to DOMINATE or be submissive.. I love role playing and have lots of fun!!  I need a beautiful girl for tonight to match my energy ๐Ÿ’– I’m sweet on the  outside, wi...
  • Asian Lilly ๐Ÿ‘ฉโ€โค๏ธโ€๐Ÿ‘จ I'm Horny Tonight Looking for a genuine sexual relationship with a like-minded asian lady? ( Do you want to view my personal profile and my sexy pictures? ) Look no further! As an Asian woman, I value deep sexy connection and meaningful fantasies.. I'm seeking a man who shares those same values and is open to explori...
  • EXPLORE YOUR KINKS WITH THE STRAP-ON QUEEN!!! Chicago Boys Deeply Love My Strap On Fetish Your gonna meet BigBen my favorite strap on! (shown in the pic attached) I'm Sandra a bi-sexual fetish friendly hot bitch who definitely wants to do it freaky and rough to men, women and couples in Chicago tonight. I specialize in strap on, pegging, Bonda...
  • ๐ŸŒŸ Looking for my Queen of Hearts ๐ŸŒŸ Chicago Hey there, lovely ladies of Chicago! My name is Maury and I am on the hunt for that special someone who can make my heart skip a beat. ๐Ÿ’“ You can find me in the dating profiles at Swap pics & contact info , so don't be shy to reach out and say hello! I'm a hopeless romantic at heart...
  • No Boring Guys Allowed... Letโ€™s Make This Exciting๐Ÿ˜‰ The one with the purple hair ๐Ÿ’œHey you… yeah, you ๐Ÿ˜. You better like your women confident, sexy, and  playful – and if you are, you might just be what I am looking for.  I am  fun, adventurous and surprise-packed – the kind of woman who can talk as much or as l...
  • Get Over Here Boy! Single and Sexy in Chicago Baby! Hannah here in Chicago looking for a friend with benefits. Hey just so you know I'm not just another piece of ass. That's not why I'm here, to just add to your body count. At the same time I will not tie you down in a relationship you don't want either. Let's be cas...
  • Chicago - Letโ€™s Make Some Mischiefโ€ฆ And Maybe a Mess ๐Ÿ˜‰  Hey gorgeous ๐Ÿ˜ I’m a 35-year-old guy from Chicago with a cheeky smile, strong  hands, and an even stronger craving for adventure — both in and out of bed. My intention is  to meet a woman who possesses confidence because I seek someone to flirt with and share laughter ...
  • Lookin' for a Playmate? Let's Make a Playdate!... Sexy Chicago Hottie For NSA Busy student wants a hot and sexy man (preferably a little older and mature) to spend some quality time with in Chicago. I'm a 22 year old white female college student studying hospitality management and love to get out and find a release once in a while with more mature...
  • Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Chicago boos out there. I'm a sexy trans woman currently living in large and lovin' every second of it. Hit me up cause I Wanna ROCK too! I'll show you what a real woman can do and everything you don't know now. I'm sex...
  • Super sexy busty woman looking for love and appreciation Super Sexy, Busty Woman in Chicago Hello. My name is Lyla. I am new to this area and looking forward to exploring more. Would like to date genuine, honorable and funny man. I love sexy and being sexy and being admired by a gentleman. View my profile pics BustyLylaX...
  • Filipina Nurse Seeking Good Man for Fun and Romance... Hi I am Amihan just graduated from nursing school and now working in a major hospital here in Chicago. I am 23 years old, 5'3, 110 pounds, 36C, love people, love men and want to find a good man who wants a beautiful family someday. I don't think I want to date people in medicine. It's hard to explai...
  • 27 Yr Old Columbian needs affection 27 Year Old Columbian Hottie Have you got what it takes to please me? I have what it takes to please you, and I know it! If you are serious about being serious and you want love and affection I am the girl for you. View my pics and contact info @Alejandra27...
  • Vivacious Redhead Bi-curious in Chicago... Hey ladies, I'm Bi-curious Lisa and new to this. I am excited and nervous at the same time. I want a hot encounter with another female to see what it's all about. Might have to take it slow at first, so please be patient with me. I am thinking a woman knows what a woman wants better than a man. I co...
  • The Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project Proudly sponsored by Chicago Lesbian, Gay, Bisexual & Trans Dating Community The Trevor Project Donations, by Megan Morrison BonePage.com proudly supports The Trevor Project, an organization dedicated to suicide prevention among lesbian, gay, bisexual...
  • Wanna play threesome? Me and hubby have been together for fifteen years now and are happily married. We live here in Chicago and are adventurous as well as fetish friendly. We want to find a third man or woman to come play with us for some adult fun. Of course we will have to meet to make sure everyone is feeling it. You...
  • 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 ...
  • Latina Beauty needs love in Chicago Hola señoras. Soy Juanita y soy local en esta zona. Tengo un trabajo y tengo mi propio auto. Puedo viajar para conocerte si quieres conocerte a mitad de camino. enviarme un mensaje @Juanita4love.  Hello ladies. I am Juanita and I am local in this area. I have a job and I have my ow...
  • Shy Asian Girl Looking for a Sweet Guy ๐ŸŒธ๐Ÿ’ฌ Hello, my name is Mei. A bit shy at first, but very soon I can become very playful and curious! I like very calm conversations with very wise and nice people especially guys! ( VIEW MY DATING PROFILE ) My friends would describe me as a romantic at heart – I’m all about a good night in, ...
  • 22F - Chicago ๐Ÿ˜ˆloves to get fucked ๐Ÿ’‹Tight Wet Pussy๐Ÿงก๐Ÿ’›๐Ÿ’š๐Ÿ’™ Hey there, I'm Yevette from Chicago. I'm a playful and adventurous woman who loves to explore all kinds of fantasies in the bedroom. When it comes to sex, I enjoy trying out different positions like doggy style and reverse cowgirl. I also have a kinky side and love experimenting with light bondage a...
  • I Melt for Men Who Lead ๐Ÿ–ค Chicago A woman who really needs to be dominated and disciplined!! I move and do whatever you want, I aim to please and do whatever it is that I'm told (NOTHING IS OFF LIMITS FOR YOU). What holds my attention? Peaceful firmness, lively drive, even just the quiet sense that choices slip into place without ef...
  • Gay Russian Bear New to Chicago... My English is not so good yet. I am Vlad from Moscow, Russia and want to find gay young man for sex in Chicago. I am 34 years old, 6'2, 210 lbs, blue eyes, big size penis, not cut, stay in good shape and love good party.  I am here for 3 years, engineer and single, but still no car. If you are...
  • Irresistible woman desiring to be wanted Hello, I am originally from Portugal and would love to meet a handsome, funny guy to do to movies and dinner with. I am new to this online dating scene but hopefully, you will be nice! Please message me @IberianLady1 Olá, sou natural de Portugal e adoraria conhecer um tipo bonito e engra&cce...
  • Confident Domme Seeking a Submissive Woman ๐Ÿ–คโ›“๏ธ Some relationships are all about chemistry. Some are about trust, control and the subtle thrill of giving up control to someone else. I’m a confident lesbian Domme and I adore the dynamic of being the dominant partner to a sweet and lovely female sub who enjoys being guided, disciplined, spank...
  • Lookin for the big one? What a silly question. Of course you are! Well, I got the big one for all you size queens out there in Chicago. I'm Frank part Italian and part many other things. Here looking for the same thing you are really. If you want to find what you are looking for here I am hung like bull. Nothing small abou...
  • Are You Uber Horny? I AM - Maybe We Can Work This Whole Thing Out Together!... Nympho Seeking NSA in Chicago I am Tory, a 24 year old, brunette living in the Chicago area, 5'5, medium build, told that I'm fun, easy to be around, a good conversationalist and have a sexy relaxed vibe. Do you live here locally, find me attractive and love big playful titties? Then I might b...
  • Slovak woman lonely and looking for guy in Chicago Dark, sultry and tall, very well built, Slovak woman is here to please and be pleased. I desire for long term friendship, fun and love. My English is getting better so send photos and message me here @TmavoZmyselná Tmavá, zmyselná a vysoká Slovenka   Tmav&eac...
  • BIG n CUTE BBW for Male in Chicago ๐Ÿ‘๐Ÿ”ฅ Brianna BBW for Chicago Male Cute, flirty and playful BBW seeking a nice man in the Chicago area. ๐Ÿ‘ I'm curvy in all the right places. I like to dress nice and I'm classy in public. But I love getting down and dirty in the bedroom! I'm a hot, naughty girl who wants it all. I love exploring sexua...