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 1st, 2025
  • Discreet meet only in the Chicago area!!! I am Jamali here in Chicago for a while doing some work for a tech company so I can't get too involved with anyone. I'd like to get out and experience this town, the party vibe and the men in it. I'll be going home in a few months. If you are iinterested in an Asian-Indian man then come check me out...
  • INSTA ACCOUNT LOCKED 30 DAYS for TOS violations. Wanna Swap Pics Insta Account Locked for TOS Violations I guess they don't like nude pics anymore or maybe my pics are just too hot for Instagram. Don't worry, the show and free pictures are still going on. What's wrong with nudity and sex anyway All I want is to hear whether you like what I post or not. It helps ...
  • Let's indulge ourselves in something extraordinary... Hello there boys I'm Tawana a 24 year old ebony female seeking a sexy man for some hot NSA in Chicago. I'm actually from here and prefer a man who lives here instead of a long distance thing. Mostly because when I'm hot and ready and I need you I'm gonna need you now, and not whenever you can get he...
  • Help! Single and Got That Tingle! Itchy in Chicago Hey there boys I'm Natalie here in Chicago looking for a handy man to take care of some of my feminine needs. Are you talented enough to scratch my itch? Must be skilled, but might take on the right apprentice who has potential. I'll have to keep you on call, because a girl never k...
  • 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...
  • 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...
  • Lesbian horse lover wants to meet same Hello girls! I am Sammi and I love my horses. I have three equine companions that I love to ride on weekends and evenings. I enjoy sunset rides and one of my horses is waiting for a co-rider to come out with me. Are you my special lesbian cowgirl? Beginners welcome. ๐Ÿ˜‰ Send me a private messa...
  • 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...
  • Chicago Latina beauty wants love Buscando a un hombre que sepa lo que quiere La gente dice que estoy caliente. Buscando a un hombre que sepa lo que quiere y no tenga miedo de conseguirlo. Escríbeme @ belleza_latina...
  • Cunning Linguist... Oral Expert Seeks Woman in Chicago Hi, I'm Calvin a single male in Chicago looking for a single woman who is funloving and passionate. I am orally gifted and speak fluent English and have an accent. My greatest oral talent however is in my long tongue - my whiskers are soft and tickly, but not...
  • Here For The Hot Chicago Girls, No Games, Just Fun! Chicago Lesbian for FWB I'm Kelsey a tatted lesbian female 33 years old, living in Chicago seeking a woman for some FWB fun and no games. They say I have a bit of a hard edge on me, but I am kind until I'm not. Just like anyone I don't like to be pushed and abused, so what more can I say about that...
  • FEELING H0RNY? I'm Your Dirty Little Secret ๐Ÿ˜ˆ CAM SEX BUDDY! ๐Ÿ‘๏ธโ€๐Ÿ—จ๏ธ๐Ÿ’ฆ I'm horny and bored ๐Ÿ˜ˆ so I set up my sex cam ๐Ÿ‘๏ธ‍๐Ÿ—จ๏ธ๐Ÿ’ฆ I specialize in kinky fetishes. Seriously, I like vanilla sex but I also like to taste all the flavors too! ๐Ÿ˜ˆ Join my cam (online now) and tell me your kinky secrets and deepest sexual desires and I'll share mine with you. T...
  • Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Chicago for Man Hello, thanks for looking at my ad! I'm Lara. I am 32 years old and transitioned when I was 24 but no surgery other than breast augmentation and some minor body touchups. I pass exceptionally well, fully functional. I'm feminine and classy so you will be pr...
  • ๐Ÿ’ฏREAL๐Ÿ’ฏHANDSOME๐Ÿ’ฏMANLY You ready for some manly gay sex here in Chicago? I know I am, I made this ad to make a nice BF to fuck or fuck me.. We can even find some other sexy guys to have some sex with too.. I love partyingโœจ and having group sex. Do you like to take it or give it? I will give you something to suck on alri...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Chicago Secret Crossdressing Hookups in Chicago Hey there. I'm Sam (Samantha when dressed up). If you're reading this ad you may be a crossdresser who needs to let your feminine side out to play. Me too! If you're in the closet or married, it's no problem. I live alone, have a nice, home with a private gar...
  • Chicago Paramedic Seeks Playmate, Friend, Lover 32 yr old, female, I'm a Chicago paramedic looking for someone who can understand a wild lifestyle and sometimes erratic hours. I work hard and I play hard. I love passion and exploring new things sexual, if you know what I mean! Kink friendly is putting it mildly. If you are interested in meeting u...
  • 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...
  • July 31st, 2025
  • 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...
  • Chicago Fetish Lover seeking hot, kinky fun! Chicago Fetish Lover for Hot, Kinky Fun! I am a seriously fun woman who has a naughty side. I have never put an advert on here before, so I hope I am doing this right. I just turned 28 and I am about 5' 6" with a curvy body and slender legs that go on forever and look great in stockings. I love ki...
  • 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...
  • Latina TS Dirty Girl Looking for a Gentleman's Dark Side ๐Ÿ”ฅ๐Ÿ‘   Sweet on the surface. Filthy underneath. View My Trassexual Dating Profile Here - As a TS darling I present like a dream while  playing like a fantasy. Stockings. Heels. A tight dress. Soft skin. And a  throbbing surprise you’ll love exploring ๐Ÿ˜˜ I need you to undress me gr...
  • Leather wearing biker chick with Harley Wanna go for a ride? I have a cool Harley motorcycle and I like to take off on weekends just for long rides. I love the feel of wind hitting my face on the open road. If you like bikes, leather and the wind in your face then go ahead and message me @HarleyChick and we can talk about meeting up...
  • ๐ŸŒถ๏ธMale Seeking Male โ€“ โ€œWhat Are You Into?โ€ Everything. Now Come Over. ๐Ÿ‘๐Ÿ–ค  You have me as your hidden secret while I am your deepest sexual desire which will cause you to  have morning soreness and a pleased expression ๐Ÿ˜˜ I enjoy oral fixation while practicing roleplay and light  dom/sub games with an interest in power dynamics and extended filthy nights ...
  • Bi-curious and Want to Try it Out... Hi, I'm Gary, 42 years old, divorced, curious but cautious, well endowed, (I'm told) medium build, 5'10, 180 pounds, ex Navy and need to keep this discreet for now. If you live in Chicago, are patient and know the in's and out's so to speak then I'd like to hear from you.  I don't know why I'v...
  • 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...
  • Shy girl looking for first date Shy girl for lesbian hookup in Chicago It is so hard to meet people at the moment and I am really wanting a date. No strings unless we hit if off. I am careful with socializing, so don't worry about me not being safe. I'm a lipstick lesbian femme, looking for fun chick to hang out with and see wher...
  • Looking for Kinky, Fun, BDSM Sex at Random Times, Must be Discrete!... S&M for Sissys in Chicago I am a gay male, bit of a thugish/bear into all sorts of BDSM, Fetish, Kink and some role play. I host and am seeking sissibois, twinks and queens for some extra sensual and painful fun. Your welcome, my pleasure! I have all the tools necessary in my Chicago dungeon to...
  • Super hot guy waiting for girl of my dreams Black Man for Romantic Woman in Chicago Dark chocolate man with romantic nature. My name is Dwayne and am 6 feet 3 and well built. I am into sports and I love watching football. Life is good and all but I want to meet a beautiful woman for passion and adventure. Check out my profile @DwayneSeekingR...
  • Hey Swingers - Come Give Granny Some Sugar!... Try This Hot Granny For A Threesome! Hi I'm Eva looking for a younger couple for a threesome in Chicago. As they say age is just a number and I'm a young at heart sexy granny still in her sexual prime. I'm Eva, 63, 5'5, 130 pounds, 36D cup, strawberry blonde hair, blue eyes and rarin' to go honey! ...
  • Nice Guy? Yep. Push-Over? Only When Youโ€™re Behind Me ๐Ÿ˜‰๐Ÿ’ฆ I'm a hopeless romantic at heart, always looking for ways to show my affection and make you feel like the queen that you are. ๐Ÿ’– I believe in chivalry and treating a lady right, so get ready for some old-fashioned charm mixed with a modern twist. Swap pics & contact infoSo if you're ready...
  • โœ…๐ŸŒˆPretty Sweet GIRL Seeking Men๐ŸŒˆbbfs๐ŸŒˆanal๐ŸŒˆall holes๐ŸŒˆ Hey there, I'm Cally, and I'm looking for someone who's not afraid to explore their fantasies with me. I love getting adventurous in the bedroom and trying out new things. Whether it's a steamy session in the missionary position or getting wild in doggy style, I'm always up for a good time.Swap Pics...
  • Tranny Cock๐Ÿ†Chicago Transgender HOOKUPSin Chicago, Illinois ๐Ÿ†โค๏ธ๐Ÿ˜‰  Check My Profile and and Dm MeI'm in the Chicago, Illinois.. area. I'm willing to travel. As longas you love TGirls and Shemales..I want to have some sexy hookups..I have some fun things in mind. I would loveto connect and see w...
  • LOCAL LESBIAN NEEDSโค๏ธ Women 4 Women only ( NO MEN ) I want to meet a lesbian tonight! ๐Ÿ‘… Looking for a sexy lady to play with tonight, W4W Women Locally in Chicago only or near by... I'm strickly lesbian. I love pussy, I love boobies. I'm living in Chicago in. I'm willing to travel or I c...
  • Flirty Fun, Endless Kisses & No Judgments ๐Ÿ’‹ 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. ๐Ÿ˜ˆ I enjoy tasty  food with slow kisses and unexpected plans that typically lead to in...
  • ๐Ÿง ๐Ÿฐ Thick BBW: Naughty, & Ready to Please ๐Ÿญ ๐Ÿฌ Letโ€™s Make This Fun! Heya babe do you seek the embrace of a bbw goddess in Chicago? Look no further! With my irresistible curves and insatiable appetite for pleasure, I'll fulfill your deepest desires. Picture running your hands along my soft, chubby frame, reveling in the warmth and sensuality. Let's escape reality tog...
  • Sex Hookup In Chicago Real New York hookup All I want is sex and more sex. This is not Craigslist. You need to link to my profile, so I know you are real and not spam. All I want is to get laid, not have my hopes up, and not hook up  Username: @InNeedOfCock >>> CONTACT ME & MEET ME<<< More F...
  • Vers, Masculine, Muscled, Looking For A Good Fucking - Host Or Travel Looking for a someone who wants to meetup on the regular. I can host or travel. You need to be discreet just like I am. I have a high level job and I don't need my personal life out there. Age is not an issue, prefer confident men who know what they want int he bedroom. Vers here and LOVES to suck c...
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  • Tatted Dad Looking For His Boy Around Chicago 35, hairy, brown hair, brown eyes, 5 ft 10, about 7.5 inches cut. Hippie type guy looking for his "boy" to smoke with. Prefer younger guys but can go older for the right guy. Hey, a hot guy is a hot guy, regardless of age. Mostly top here, but very oral and loves to eat a hot ass. Send me a message ...
  • The Ultimate Swingers' Fantasy - Fuck Me WHEREVER, HOWEVER You Want! ๐Ÿ‘„ Any Fantasy, Anywhere, Any Time - Sexy Couple Wants to Make Your Dreams Cum True- Username: @FantasyWoman54- Location: Chicago- Swingers Profile: Yes - Hotwife Pics: 44TEXT US DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials Baby Tell Me, What's Your Fantasy? Is it...
  • Super Sexy Good Girl Needs Another Cock To Suck, Are You Man Enough?? ๐Ÿ˜˜๐Ÿฅต I'm Just A Good Girl Who Needs A Spanking Sometimes - Username: @BreadNButtaBB- Location: Omaha, Nebraska- Swingers Profile: Yes - Hotwife Pics: 32TEXT US DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials Farris: Hot blonde, skinny physique. I really love having on...
  • 29, Swimmers Build, Looking To Fuck Tonight - Host or Travel Title says it all, looking to host or travel. Looking to fuck all night. I am hung with a 9 inch uncut dick. Verse, but more of a top. But if you have a nice cock, I'd be riding you in a heart beat. More into the vibe of the guy than worried about age or looks. Hit me up and see if we are a match. ...
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