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 26th, 2025
Busty chocolate Beauty loves milk chocolate treats Busty Chocolate Bunny in Chicago Hey gals, I am Bunny and I am dark chocolate in complexion and big busted. I am a foodie and I love all foods! I watch all kinds of food shows from all over the world! Hit me up @BustyBunnyXXX Hope to speak to a food/dining loving lady soon!  Username: @...
DESPERATE SEEKING A REVENGE FUCK! 🥒🥯💦 Newly single Chicago 22 y/o female needs a good fuck 💦 Hey there, I'm Trish from Chicago. Let's get right down to it. My husband left me and I need to fuck to make me forget about his sorry ass. I'm tired of being neglected so I'm looking for a nice, attentive man to keep me warm tonight. I'm cl...
Submissive and Need a Dominant Sir in Chicago Our Little Kinky Secret in Chicago Allow me to introduce myself, I am Chelsea here in Chicago looking for a Master to give me what a real woman needs. I am into domination, humiliation, bondage, roleplay, gags, whips, toys and am still exploring my fetishes. I'm a professional woman working in the ...
King of your heart waiting for you in Chicago Abe, 32, local in the Chicago area, own my own business. I work hard and play hard. I am looking for a gentle guy who is understanding and kind. I love to laugh so you have to be funny, plz. Not all the time, but you need a good sense of humor. Life is too fun to be serious all the time. Message me ...
DIVORCED👩MOM/MILF Hey Love I am an older cute girl Horny for sex ,& I love to kiss and suck your dick. Bareback, Anal, Greek, GFe ,bbjs, kiss I love getting my pussy licked while I suck cock. I can host, but, willing to travel. 😘 I have nasty videos for sell💋 I'm 42 Years 🅳🅸🆅�...
Just Got a Delivery of Kinky New Toys! Young lesbian girl Robbie just got some kinky supplies with lots of batteries. If you are into some kinky fun and live in Chicago then HMU for a good time. I'm 21 years old, bit of a butch/tomboy type who is just now getting into fetish play. Got some bondage gear, pumps, whips, gags, electro stimul...
Wife Swap in Chicago Anyone? Swingers Seek Sexy Swap in Chicago Hi we are Dave and Lisette here in Chicago. Admittedly we are pretty new to the swinger lifestyle and don't want to cross any boundaries, but we would really like to find a couple around our age to swap partners with. You don't have to be married like us, just in ...
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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...
6'2 Dark Chocolate in Chicago Hey! I'm Gary, age 27, tall, dark, chocolate, want to meet you. Super ready HIV Negative. Come and play in Chicago at Roscoe's Tavern or Dorothy.  Message me @ChocolateRush for my pictures and #...
Black Circus Dick Looking To Top A Fags Hole In Chicago. 12 inch, uncut, black, monster, circus dick looking for a power bottom that knows how to take it long and hard in {CIty}. I like a nice fat ass that I can watch bounce while I go at it all night long. I can host or travel. I'd love to see you bent over my bed as you watch yourself in my mirror as I ...
🥵🍆SHEMALE COUPLE SEEKING SOMEONE FOR SEX🍆🥵 Hello men and women. We're a TRANS couple seeking someone or multiple sex partners to join us. We have cock and tits.. Does this turn you on? We're willing to let you hop in our bed, or we will come to your place. I really love sharing my partner and being fucked in front of her.. OMG I"M GETTING HA...
A Hot Fucking Game Of Four-Some Roulette. What Kink Will We Choose? HotWife? GangBang? WifeSwap? - Username: @JNDSwingingCouple- Location: Miami, Florida- Ages: 23 & 26- Swingers Profile: Yes- Hotwife Pics: 57TEXT DIRECT FOR BOOKING INFORMATION- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials We are Julia and Derik - I'm a Hotwife and He likes to watch and join in at the ...
Tired of Fakes and Game players? Want hot juicy and tight? Real Chicago Girl, Hot, Juicy & Tight 100% real Chicago girl and very skilled! My tantalizing curves and sexy eyes will have you mesmerized in seconds.  Enjoy my silky skin, luscious legs and sensual breasts.  I love to tend to your needs. I promise a safe, sexy and secure envir...
British T-girl Seeking Classy Gentleman in Chicago... I am Lacy, a white, blonde haired, trans woman, 30 years old, 5'9, 160 pounds, from Manchester, England and need a man who is educated, refined and handsome. I have just relocated to Chicago and am financially independent and looking for a gentleman who is like-minded, equally solvent and has except...
Newly Out Looking for love Newly Out Lesbian in Chicago I have only been out for a few months and I am totally new to the dating scene. I have no idea even what to say or where to start! I will tell you a little about me. I am a youth worker and I have a college education. I am 26 and sort of tomboyish but I do wear make up ...
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...
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...
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...
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...
Tempting BBW in Chicago Ready to Heat Up Your Night 🍰🍰🍰🍰🍰 Are You Ready to Hookup With a BBW Hottie in Chicago Tonight??  Hey there, handsome. I'm a curvy goddess with a craving for some steamy fun in Chicago. With my voluptuous curves and a smile that'll melt your heart, I'm ready to make our time together unforgettable. Imagine running your ha...
I wanna be your friend and lover Mature black man in Chicago Howdy, my name is Samuel and I am a mature gentleman looking for a lady who is smart, funny and outgoing. I am 52, widower after 28 years, no kids. I am into riding my bike, the gym, and fishing on weekends. There is just one thing missing - maybe it's you! Do you like d...
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...
Hot Italian Sugar Baby Wants to Live Her Best Life Now! Hello distinguished gentlemen of Chicago! I'm Alexis, full blooded Italian, 21 years old, 5'6, large boobs, 140 pounds a native of Aurora originally, but moved in to the city when I turned 18. I love the finer things in life and more mature men, so this works out for the both of us really. If you ar...
Lesbian, Bisexual & Bi-curious W4W Heat! JOIN FREE FEMALE ON FEMALE HEAT! Local Lesbians, Bisexuals & Bi-Curious Women!  SIGNUP FREE: INSTANT W4W ACCESS! Uncensored PicsSwap Your PhotosLive Web CamsPrivate MessagesSext & Hook Up! View Females | Upload & Swap Pics | Sext Messages "Because sometimes onl...
Trans Flight Attendant Seeks Man for NSA... Hi I'm Annie, a 32 yr old t-girl, a Chicago trans flight attendant looking for someone who can understand my wild lifestyle and sometimes erratic hours. I work hard and I play hard. Let's wing it tonight baby! I love men, passion and exploring new things sexually. To say that I'm fetish friendly wou...
Come tie me up and let's play.... Tie me up and use me as your sex toy. I love to give you total control of using me in any way you like. I love it rough, in-the-ass, and I will make gang bangs, and I'd love to eat my pussy out of your wife and suck your dick while my cum drips from it. You can dp me. I love more than one dick at on...
Vibrant and Intense 26 year old wants to meet sexy dude Hi! My name is Angelina. My body is in great shape and I like to exercise and stay fit. I am fun-loving and down to earth. Would like to meet same in the perfect guy. I love swapping pictures and sext messages on mobile so don't be shy. I think swapping pics is the perfect way to set the tone for a ...
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...
Chubby Chick looking for guy who can handle me! So, I am a little heavy but more just curvy. I have 44DD boobs and I love, love, love to laugh! You gotta be funny if you are going to date me. Why not text me your favorite joke and we can see how we get along!  Lisa44DDChicago...
Transgender Goddess for Late-Night Escapes & Filthy Fun 🌙💋  It’s late. You’re restless. And you’re craving something… different 😏 - View My Transsexual Dating Profile - As  your TS fantasy girl I offer sultry and smooth vibes while delivering experiences beyond what your ex could have  imagined. My secret between...
Road Head Sally Drivin' Hard in Chicago Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Chicago. Hey, what's the best time for road head? When there's gas in the tank baby! Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or park...
Crystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Chicago area and want to make some new friends! I am a masseuse, hot body, in great shape, and well hung. If you want to get together, Send me a private message Crystal27trans <3  Username: @Crystal27transLocation: Chicago, IllinoisAge: 2...
PENTHOUSE PARTY For Insane Swingers Fun - Cum With Us! GOING FAST - BOOK NOW! 💋🔥😈 Party Favors & All Night Sex Drives- Username: @SwingersBalls2004- Location: Chicago, Illinois- Swingers Profiles: Yes- Party Pics: 27TEXT DIRECT FOR BOOKING INFORMATION- Video Chat: Yes- Messenger: YesPics & Socials We're looking for more swinging couples to join us in a swingers part...
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 ...
WE CAN HOST OR COME OVER 💥Chicago🌟😉 Hey there, I'm Shari from Chicago, and my husband and I are a fun-loving swinging couple looking to connect with like-minded individuals who share our passion for the swing lifestyle. We love the thrill of meeting new people, exploring new experiences, and indulging in our deepest desires together.&...
Secret Lovers ...💍❤️😘 Shhh Don't tell my husband My Husband doesn't like to get wild like I do. I want to have super sexy fun!! 🤩🤩 Discreet Messages - Private Message 💌 I want to do all the things I'm missing out on with you.. I need to have fun and I need to feel a real man again. Want us to make porn together, meet women ...
Black/Ebony Transsexual - Your New Addiction – One Taste and You’ll Beg for More 🍑💋  Warning: I’m addictive 😘 View My Ebony TS Profile here - I possess more than attractive features. I am a complete  TS woman who enjoys teasing and pleasing while taking control of your dreams. My body features long legs and  thick thighs and soft lips and a hidden secret th...
CHICAGO - black🍆crossdresser  EBONY/BLACK CROSSDRESSER  in Chicago Illinois  👅😉🍆  I've been living in Chicago Il, for 2 years now.I love crossdressing and being treated like a lady.I have a nice big cock and I know how to wear sexyclothes really nice for you. I'm thinking about...
Woman looking to swing. I love to swing. NSA sex is the best. Not new to this. I'm married, and my husband lets me do what I want with who I wish to make a regular hookup. I have a few hot wife friends that are bi and would love to join in. Username: @NeedNSA68 >>> CONTACT ME & MEET ME<<< More FREE...
Chicago - Let’s Make Some Mischief… And Maybe a Mess 😉  Hey gorgeous 😏 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 ...
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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GangBang Island - Only It's Your Ottoman and I'm On My Knees Begging For Cum 😘🔥🔥🔥🔥 Let's Make Each Other Cum Over And Over And Over... - Username: @AsiaMay8364- Location: Chicago- Swingers Profile: Yes- Hotwife Pics: 29TEXT US DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials I wanna be your sex slave and bf will stand to the side and watch the games....
Bored Housewives In Chicago Want Your Cum! 🍆💦👅 Bored and Lonely Housewives Looking For People To Do - Username: @Lking4Swingrs- Location: Chicago- Swingers Profile: Yes- Hotwife Pics: 45TEXT US DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials Got married early - Husbands are wealthy and gone often, leaving my best ...
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I want to be your sex toy!!!!!!!!!!!!!!!!!!!!!!!!!!!! I am looking to be used. Like the slut I am. I'll enjoy being your sex toy. All I want is a dick in any way you wish. Do you like to get deep-throated? I have not found a dick; I can't. Username: @SexToys6969 >>> CONTACT ME & MEET ME<<< More FREE Adult Classifieds SitesJoin ...
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Swinging Suburban Housewives of Chicago🔥🔥 Double Penetration And Double Creampies- Username: @GeraSwingersCouple- Location: Chicago, Illinois- Swingers Profile: Yes- Hotwife Pics: 11TEXT DIRECT FOR BOOKING INFORMATION- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials I want two men to cum in my pussy and Ass at one time. C...
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