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!

Home / Dating /

Show Ads In: Bloomington-Normal | Carbondale | Champaign-Urbana | Chicago | Decatur | Peoria | Quad Cities, IA/IL | Rockford | Springfield, IL

May 7th, 2025

Bear looking for shaved dude My name is Freddy (FrEEkXX) and I am looking for a guy to love. He has to be shaved because I like the feel of my beard on bare skin. Drop me a text or email @FrEEkXX if you want to hang out. ...

Here to be your sexy little slut.... Slut in Chicago Wants NSA Hey you sexy men in Chicago I'm Jill and I just can't help it when I see a hot guy. I fall in love (or lust) and want him to kiss me, touch me, and squeeze me and be in me. There are lots hot guys around here and I know I can't have em all, so here I am to get at leas...

Hey, any SteamPunkers out there in Chicago?... Hi, I'm Brad T. from Chicago born and raised. I love everything SteamPunk and am searching for a local woman who appreciates the romanticism of the late Victorian era. I'm 30 years old, love sci-fi, SteamPunk, conventions and events, travel and work. I have a dynamite job working with younger autist...

Married But Playing in Chicago Married Woman Playing in Chicago Hey guys. My name is Jessica @Jexxica27, age 27. I'm married but playing around. He don't care. He said so and he cheated on me first so here I am. I just want to have a good time, no strings attached. Can you give me what I haven't had in a long time? I like i...

I'm a Snobby Stuck Up BITCH! I'm AllyCat and I need a sexy AF man to give it to me rough and hard and pound me - use me AGAIN and AGAIN! Have your way with me and put me in my place! Teach me a lesson I won't soon forget baby! Make me tap out and then beg you for more. I'm always ready and you should contact me here if you live...

I Need a Massage... I'm a Sucker For a Good Massage!... Hey any of you fellas in Chicagoland know how to give a girl a body rub? I need a slow long lasting massage by some stong sexy masculine hands. No quickies either! If things work out maybe we could have a mutual more long term thing? You know, a more steady get together? You scratch my back and rel...

Smoke and Leather! Smoke and leather go together. I'm Toby, 32yrs, 6'0, 200 pounds, extra large, living in the Chicago area, a hairy thug, def top gay man wanting to pound gay, bisexual and bi-curious men. Just be ready to pleasure me while I chain smoke. I don't care if you smoke or not just be damned grateful that y...

New to this place, Andrew, 36. Man Seeks Woman in Chicago Ok, what do guys say on these things? I want a kind, friendly and fun lady to hang out with and maybe get to know each other a bit. I am tall and somewhat slim build with dark brown wavy hair and blue eyes. Send me a message @TallManChicago...

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...

!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Chicago Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Chicago to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enjoy 24/7 Online Chat M...

Hey Ya'll Its a 3-Way Booty Call! Try an Ebony Threesome With Me! Vera here in Chicago looking for a few good swingers! Or, at least one good couple. LOL  If you like hot chocolate and a big booty here I am. I got some hefty hooters too that will make your mouth water and hypnotize you so I can take advantage of you. Hit it an...

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...

Totally new to this kind of thing! I use a couple of apps to do dating but I am never tried this site before. I am hoping I came to the right place. Are you my Mr. Right? I hope you are not my Mr. Wrong! My name is Lisette and I am 26 and single and I love to go to the beach and the movies. Check out my profile page and send me a mes...

Hot chick needs female distraction Will you be my distraction? Hello! I am Lucy and I am so wanting to get out and meet someone who can take my mind off things! Are you caring and a good listener and a good kisser? If you are, hit me up with recent pics and a message @JuicyLucyX I look forward to talking with you if you are cu...

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 ...

Chicago Wild Child Looking for a Thrill or Two... Let's Go Wild Baby! Hey boys looking for a party? I'm Jenna ready for life in the fast lane here in the Chicago area. About me - 21 years, 5'5, C cup, smoke, love to hang with the boys. If you are looking for a girly-girl then I'm NOT 4 U! Let's just take things as they come and don't get too hung ...

Sexy hung and big busted Hung and Busty Shemale in Chicago Tammy, 39, 38DD, 9" and so cute!! What more could you want in a gurl?!! How about you message me @Tammy38DD and we can talk and meet! Send your recent pic for mine....

Young, Fun, Perfect body and 36DD looking for nice gent to date Young, Fun, Perfect Body and 36DD 26 yr old looking for fine looking man, with fit physique. Must enjoy sex! I like being active and enjoying life. I'm giving online dating another try. My Pics and Contact Info 36DDblonde Send your photos and mobile# for mine. Tell me a little about yourself...

𝔹𝔹𝔹𝕁 𝔾𝔽𝔼🌮💦 LATINA🌮100% new girl🌈🔞LATINA💖 Chicago Hey there, I'm Rene from  Chicago . I'm a fun-loving girl who's always up for trying new things in the bedroom. I love to explore my fantasies and play with different kinks. Are you ready to join me on a wild ride of pleasure and excitement? 😉 When it comes to sex, I enjoy getting a lit...

Strict Shemale Dominatrix in Chicago - @DesireeTransDomme Powerful African-Queen Dominatrix in Chicago I am full-time professional Domme Desiree. My Chicago area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you will learn to...

New Body New Me M2F post-op in Chicago Hi, I'm Natasha, newly transitioned and ready to date. Gorgeous red head with slender legs and curvy body. Want to come and join me for a drink? I love sex in my new gender!!! Seeking a local area man who will enjoy sex and passion with me. Message me online Natasha...

Intoxicating-Stacked Russian Blonde Beauty... I am a Russain woman coming to America soon I think, and hope someday to meet nice American man, and have beautiful American family. My name is Korina and I am living in Moscow. Maybe find good man in Chicago? I try different places for finding attractive and successful man in the USA, but not yet. ...

Keep Calm And Have A Threesome in Chicago! Swinger Couple in Chicago I'm Daily and my hubby is Don, we are in our 30's, live here in the Chicago area and are swingers looking for a sexy man and or woman. We love role play as you can probably tell from our pics. We can be a little kinky I suppose, but mostly we are into adult role play and N...

Swingers Seek Sexy Man or Woman for Menage a Trois in Chicago How About a Threesome in Chicago? Funloving couple in Chicago would love to meet open minded men and women for casual hookup. We are Dana (26 years old) and Rita (25 years old) and have just about one year in the swinger lifestyle and are having a blast. We have tried wife swapping and foursomes, b...

May 6th, 2025

Looking for Mr. Goodbar... Just out, and just out of the Marines, now a college student and 22 years old gay male living in Chicago Looking for experienced well endowed older man to give it to me. I'm 5'11, 180 pounds, blue eyes, brown hair, 7in cut, and in great shape. This is a little awkward, I'm new so be patient with me....

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....

Dinner, Drinks… and You in the Driver’s Seat? 🍷💋🍑 Chicago Hey there, lovely ladies of Chicago! My name is Baily and I'm on the lookout for that special someone to light up my world. 💫Swap pics & contact info I may not be a prince charming, but I can promise you plenty of laughs, good times, and maybe even a little bit of romance along the way. ...

I will always laugh at screaming goats... Chicago Man Seeks FWB I’m George age 40 here in Chicago and am a bit of a shut-in. I still like going out for drinks and having fun but I find more peace and have more fun just kicking back at home. I love the beach, movies, Disneyland, writing music and poetry, spontaneous trips, and playing...

Deep Throating Is The Game - Wanna Play? 🍆👅 Raw, Uncut and Everything I Want in An Orgy - Username: @SuckkinOnThemDicks- Location: Chicago- Swingers Profile: Yes- Hotwife Pics: 27TEXT US DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials Everytime we post an ad like this we end up completely swamped with messages ...

🌶️Male Seeking Male – “What Are You Into?” Everything. Now Come Over. 🍑🖤  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 😘 I enjoy oral fixation while practicing roleplay and light  dom/sub games with an interest in power dynamics and extended filthy nights ...

Help - Can't Afford a Masseuse in Chicago! Busy Girl Needs Body Rub in Chicago Mmmm... touch me baby! I'm DeeDee a waitress in a very busy restaurant here in Chicago. I work day shift when all the older crowd and construction workers come in and it's hard to meet guys my age. When I get off I'm soooo sore from carrying heavy trays and my fe...

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 terrible but after a drink or two you probably won't care! I love singing 60's and 70's disco and some modern rap. Message me with pics @CarmelK...

Italian hot woman looking for love Adriana Hot Italian Woman i guys!  my name is Adriana and I am from originally from Italy. I moved here recently and want to meet a nice friendly, fun guy. I own my own private cozy place. I am friendly and a fun girl. Message me. See you soon! ~ Adriana in Chicago...

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 ...

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...

Looking for the world's best playmate! Need: One good looking guy who can make me laugh Also: has to like music and movies and be a gamer, not a player. What you get: Me! My name is Patrice and I am 25, 5'6", curvy with dark hair with a blue streak straight down the back of my head, which I love! I am also a pretty good cook, so if we ...

Chicago Cougar Could be a Cubs Delight Tonight!... Cougar on the Prowl in Chicago Hi there you sexy cubs I'm Joan and I'm gonna spoil you tonight! My den or yours, let's get wild in the sheets till I've had my fill. If you are a cub between 18 and 30 and live in the Chicago area then I've got something for you. Maybe you thought school was ou...

Latina TS Dirty Girl Looking for a Gentleman's Dark Side 🔥👠  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 😘 I need you to undress me gr...

YOUNGER COUPLE ( 18+) LOOKING 4 SOME EXTRA FUN 🔥🥵😉 Hey there, I'm CONNIE from Chicago. My hubby and I are a swinging couple who love to explore our sickest fantasies.. Do you want to hear more about what we're down to do? I want to make love with like minded individuals and fuck hard!! The thrill of wife swaps, threesomes, and the swing lifestyle tu...

Amazing kisser looking for lips to practice on Lipstick Lesbian Loves Kissing Do you love kissing? I do! I love it!! It is such a turn on! My favorite parts to kiss are my neck and my face and my lips and my whole body! I am Kimberley, 22 and a part time waitress. I'm eager to meet you!! Send me a private message to @LipstickLesbianKim User...

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...

Confess Your Naughty Kinks to Me! Dirty minded twink 21 years old, well endowed, 5'9, 160 pounds, blue eyes and just out of the closet loves to hear about and play out kinks of all kinds. Blow my mind with your hottest fetish! Better yet let's get together if the mood strikes and fulfill yours and my fantasies. If you live in the Ch...

Swingers - Estella Wants Threesome - Live La Vida Loca! Hi Chicago Swingers I am Estella looking for some real fun - Estoy Muy Caliente muchachos y muchachas! I have a need only you two can fill. You don't have to be super models or anything just come with a sexy attitude and that makes it all good in my book.  I prefer a hispanic or white couple w...

Tom, 42, wants single minded woman Hello ladies, I am Tom, age 42 in Chicago. I have a good job, decent car and own my house. Life is pretty good and I'm ready to take the next step toward finding love. I am not looking for someone who is going to give up stuff for me. I want a woman who is already established. If you are that woman...

Looking for my sexy booty boos in Chicagoland... Shania here waiting for my Chicago superman to take me away tonight. I live in the Des Plaines area and am employed in education. What do I want? Well, I'm open to some NSA or long term if the vibes are happenin. I'm medium height, extra large boobs, 145 pounds with a big booty.  I'm down for ...

Genuine, yoga loving woman looking for physically fit man Busty Vixen in Chicago Area Busty vixen with a love for yoga and running. I am active and stay in good shape.  Serious guys only please. Text now @BustyVixenCarole Let's go out on the town, have some drinks, have dinner, whatever you like. I can have fun doing most anything. I like havin...

Shy guy wants someone to bring him out of his shell Shy guy for male in Chicago Hey, I am Scott and I am 27. I am not an extrovert but once I get comfortable with you I can be funny and a little out there. I am not the sort who like attention too much but I do love clubbing and sports. If you are into jetskiiing it's a plus, otherwise, anything wate...

Handsome Butch looking for Fem Beauty Butch Lesbian for Fem Beauty in Chicago My name is Mikayla but my buddies call me Mikey. I am 26, working full time and love to ride my Harley. I am interested in meeting a beautiful soul who likes to feel the cool breeze in her hair from the pillion seat of a 750 heading into the mountains....Let ...

I'm Top Bitch! Get a Taste of Femdom! I'm Mistress TopBitch here in Chicago, and I'm going to pound and drain your worthless asses of all self-respect, and you're going to fucking love every damn second of it! Strap-ons and pegging lesbians are my speciality. (among other things) If you are all filled with fear a...

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...