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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September 15th, 2025
Looking For My Lesbian Cosplaymate in Chicago... Im Bethany into cosplay, roleplay and women, but not necessarily in that order. I need a lesbian, bisexual or bi-curious cosplaymate in Chicago who likes the world of fantasy like I do. By day I'm a mild-mannered beautician, but when my alter ego comes out I'm your super hero, or sexy housemaid or a...
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...
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 ...
Bored and lonely blonde barbie doll Bored Blonde Swap Pics and Numbers I am bored and lonely and I want to meet someone who is funny and kind and really clever. I am no dumb blonde so I will give you a run for your money. Come and meet me (BlondeBarbieDoll) on my personal profile page with pics and my contact info. Let's have s...
Sensual Dating Sensual Dating with Jen Wanting to date sensual caring man. I will do things the way you like. I like super open minded guys who show respect. Kink friendly!!!! Just pm or text please, no calls. My contact info is here SensualChicagoJen Open minded Kinks welcome Femdom  420 frien...
Come Join US!!!! SWINGERS DOWN FOR ANYTHING AT ALL! 😘🔥 Chicago 💋 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...
Join Me for an Episode of The Hung and The Restless! Endowed Chicago Gay Man Seeks Hookup I'm a gay man living in the Chicago area with 10+ thick inches of uncut restless pleasure. I'm Matt 28 years old, 6'0, 200 pounds, muscular, black hair, brown eyes and take care of myself. I'm top, but can be versatile depending on you. You will find me warm and...
Sex and Smokin' Leather... Hi Leona here in Chicago (originally from Rochester, NY) and am looking for a sexy man who smokes and loves sex. Or at least a man who doesn't mind smoking and sex. I wear a lot of leather gear and smoke obviously and have a dirty mind to go with it all. I moved here and work at the Chicago airport ...
Partners in crime, or? Sexy, Slytherin, Aries, ISTP and more, if that gives you a hint about my personality traits. So, I’m a sexy, sensual, tender, animal loving, bookworm. I am a bit of a flirty whore, who loves mystical magical movies and stories, so let’s get that out in the open. If you live in the C...
Looking 4 a Man 4 Sex 🍆💦 & 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...
Tantalizing Tina with a HUGE W33NAH! Chicago Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Chicago men and wnat to show you a time you'll never forget! Do you like them thick, long and uncut? Then I'm the girl for you. Look no further for a passible and functional t girl - HERE I AM!  About me: 2...
Bi-Curious Female in Chicago... I'm Cory, bi-curious, living here in Chicago, young, (23) about 5'7, about 140 pounds depending on the time of year, have perky tits, love sex and want to experiment. As a beginner I need to learn the rules and such. Please be patient cause I might be awkward at least at first. I am curious I think ...
Wanting slightly older gentleman Hello. My name is Sylvia, age 24 and I am pretty done with young guys who mess around. I want a guy who is mature and kind and likes to travel. Please contact me so I can learn more about you!  Send your recent pics for mine. I just took some naughty pics with my girlfriend Brianna. I think yo...
Nigel 56, Chicago new here Male 56 seeks woman in Chicago Howdy gals, I am Nigel and I am back on the market after a settlement with an ex and my subsequent relocation. lol. That's life. Now, to find my true one and only love. I am lighthearted and friendly and I love to laugh and be made to laugh. I've been single over a ye...
HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Chicago! LET'S TAKE CARE OF THAT TRANNY FANTASY! "Experience your secret tranny desires in real life!"  Hot shemale Gia wants to hook up with you in Chicago!  No strings - just great times, so join my page free for instant access! Shemale Gia's Chicago Sexbook @ShemaleGia27 Photos: 42 V...
Hot Girl Wants To Hang Out With Woman in Chicago Are you cute and fun? I'm lonely and looking for good times with someone special. Just send me a message @HotGirl4XXXFun and I will send my recent pictures. 🔥 Please send your pics and contact number. Let's text and go from there. Local fem girl looking for local female friend (butch or fem) to ...
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...
BANNED ON FACEBOOK... Wanna see the pics that got me kicked out? BANNED ON FACEBOOK. WANNA SEE MY PICS? Hey there. I'm Kimberly, my profile is in Facebook jail for posting my hot pictures.  WTF?! So here I am. Want to see the pics that got me kicked out? Look me up: KimberlyX69 My pics and videos are free. No need to pay for anything. Just ...
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 🅳🅸🆅�...
Need My Big Phat Booty Princess... I love big butts and I cannot lie! I'm a red blooded black man, 29 years, 6'0, stays in shape, lives in Chicago and who loves him some bubble butts. More cushion for the pushin baby! If you are a woman living in Chicagoland with an exceptional sexy ass then don't hesitate to get hold of me and show ...
OLDER BABES for YOUNGER MEN!! Older Women for Younger Men Sexy older babes show younger men how to truly please a woman! Women Join Free | Men Join Free | View Photos  1. Join Free for instant access 2. Chat or sext with members 3. Arrange local hook ups! More&nbs...
Help - I'm a Nymphomaniac AND an Insomniac - There is Only One Cure! I'm sort of a reverse Sleeping Beauty story. lol I need lovin to put me to sleep and give me those feel good endorfins. I want to find a sexy man to hookup with when the need strikes me. Of course you can let me know when the need hits you too. This isn't a one way street after all. I'm 29 years old...
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...
Southern belle new to Chicago out for a good time A truly southern belle, born and raised with all the charm and grace a lady should have. I love cooking, pleasing my man and music. I'm open to most anything fun. I am open minded, beautiful, and I have a lovely twang! Ya'll wanna meet me for some fun and good food? Please say yes! Contact me! @Sout...
Italian Goddess Ready for Love in Chicago Parli italiano? If so we can get down and personal and get to know each other. If you don't Parli italiano I can show you some phrases *wink*. Why not private message me for a date? @DonnaSexy27...
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...
Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Chicago Hey! Thanks for looking at my ad. This is the first time I've done this so bear with me plz. I am Jared, FtM trans man. I transitioned at age 25 and I just turned 30. Come and meet me!  Check my personal profile @FtMJared29 and say hi!&nb...
No Strings in Chicago - Hot and Sultry, Looking for Affection Thanks for opening my ad. I've been neglected for far too long and am in need of affection. Things are complicated so no strings only please. That is likely to change at some point in the future. My hair goes down to my lower back and I have soft skin. My height is 5'8" and I am slender but curvy i...
Blue Eyed BDE... Some say I should be in porn, but I have a profession that doesn't mesh with that, (EMT) plus I wouldn't want my future kids to ever see it. Hi ladies I'm Chad, 31 years old, not too serious, blonde hair, blue eyes, 6'0, 190 pounds, size 11" real uncut thick burrito type, I'm very oral both giving a...
Playful Dove Ready to Fulfill Your Wildest Fantasies 😘🔥 Chicago Hey there, sexy! My name is Dove and I'm a flirty little vixen from  Chicago . I love to explore my sexuality and try new things in the bedroom. Are you ready to join me on a wild ride of pleasure and excitement? 😉 Swap Pics & HMU @dovesh47968   I'm seeking a sexy man!! 😍🥰�...
🙌🤝MY BF and I INVITE YOU INTO OUR BED 🛏️ 😍 Hey there, I'm SexySally from Chicago. My husband 💍 and I are a swinging couple who love to explore our fantasies and indulge in some kinky play with like-minded individuals. The thrill of wife swaps, threesomes, and the swing lifestyle gets us both excited and eager for more adventures.&nbs...
Chicago💋 TS Tina – Your Naughty Escape, Anytime, Anywhere 🌎🔥 Hey sexy… Your sweet seductive fully loaded TS dream girl Tina is here to fulfill your deepest desires from anywhere in the world 😘 I possess the right amount of softness while maintaining the perfect playful demeanor and I always welcome men who understand how to treat a genuine wild wom...
Let’s Flip the Script—You Lead, I’ll Moan 😍🎀Chicago Hey there, lovely ladies of Chicago, My name is Wells and I'm on the hunt for someone special to explore this beautiful town with. 💫Swap pics & contact info  I'm a thrill-seeker at heart, always on the lookout for my next adventure. Whether it's hitting the slopes together or enjoyi...
💯REAL💯HANDSOME💯MANLY 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 partying✨ and having group sex. Do you like to take it or give it? I will give you something to suck on alri...
Blond Twink Need My Smooth Ass Fucked I am ass up, face down and looking to be fucked anonyumosly. You walk in, slide it in and spill your load deep inside me. All ages and races welcome. Looking to see how many loads I can collect today. I am 19, 5,9 160lbs with a nice smooth bubble butt that needs your attention. Hit me up. FREE Gay ...
2 ASAINS👭💎bj/gfe/rubs Do you want to feel the soft touch and body of a hot and petite ASIAN girl?? How about two asian ladies, who know how to make you feel good in all the right places.. Let them rub, kiss and lick you. All over your body, check them out here, we're waiting. ❤️ My Profile - Learn more about me. �...
😉💋🔥Raw, Uncut, Dicks and Pussy Everywhere, Good Old Fashioned Orgy 😉💋🔥 Raw, Uncut and Everything I Want in An Orgy - Username: @DaisyJames473- Location: Chicago- Swingers Profile: Yes- Hotwife Pics: 27TEXT US DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials We like role playing, dress up, BDSM (kinda more on the lighter side of things the...
Super Sexy Good Girl Needs Another Cock To Suck, Are You Man Enough?? 😘🥵 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...
Leather, BDSM and Bondage Lovers Wanted. Looking to host a BDSM & Bondage sex party. All shapes, sizes, ages and positions needed. I have a house out in the country with a private yard that we can do this in. Looking to arrange an all night sex fetish fest. Contact me if you are interested. FREE Gay Sex Finder Service! We get you LAI...
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...
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 ...
Frisky Bottom Daddy Looking To Be Plowed Looking to have my ass streached by a guy that knows how to destroy a hole. Prefer men that are aggressive and wants to take his aggrevation out on my ass. Trying to be your sex slave for the night. 5ft 9, 150lbs, 35yo. Pics posted. Hit me up. FREE Gay Sex Finder Service! We get you LAID, gaurunte...
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 ...
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....
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Personal Sex Toy And Cum Bucket For Couples! 😉💋 Personal Sex Toy and Cum Bucket Addie! - Username: @SwingersLink2004- Location: Chicago- Swingers Profile: Yes- Hotwife Pics: 42TEXT US DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials Addie: I'm a bad babe who loves to be taken care of by multipl guys. I love the femi...
Let me be your freak! Let me be your freak. I love to do threesomes with you. Does your wife like pussy, or do you have a friend that would like to join? If so, don't hesitate to get in touch with me now and take care of me. Username on Get An Escort: @FreakSex >>> CONTACT ME & MEET ME<<< More FR...
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College Guy Looking For A Fuck Buddy In Chicago Are you near Chicago? I am looking for a fuck buddy to fuck around with from time to time. It would be great if you had a place, or we can do car stuff. I am 20, fit, 165 lbs and 5ft 8. Prefer men under 45, but men can be hot at any age. Love uncut guys, but it's not required. Send me a message and ...

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