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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  • June 21st, 2025
  • Wanna play threesome?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...
  • Southern belle new to Chicago out for a good timeSouthern 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...
  • hippy_nomad Loves antiques, rescuing stray animals, 420...hippy_nomad Loves antiques, rescuing stray animals, 420... Must be 420 friendly. Currently living in Chicago I am an honest, hardworking and caring woman who is looking for the same. Let’s face it we’re not getting any younger so who wants to play games- NOT ME! I also like going to flea markets, dancing and most of all vacationing! So if you th...
  • Intoxicating-Stacked Russian Blonde Beauty...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. ...
  • Playful Cub Searching for Cougar in Chicago...Playful Cub Searching for Cougar in Chicago... I love mature women and appreciate the skills they've developed over the years. I'm Dana 22 years old, have my own car and apartment and good job, so I'm not looking for a sugar momma situation. I just want a sexy cougar to play with and get to know even if it's for a short time. I would be so grate...
  • II'VE GOT A GLORY HOLE FETISH - CUM 'N GO! Chicago Glory Hole! Hi all you sexy guys in Chicago I'm Riley, and the other girl here is Harper a neighbor who likes to join in the glory hole fun sometimes. We have a club house that has a glory hole set up that's pretty nice actually. Our boyfriends like to watch, but you'll never see them. I we...
  • Black man, 31 needs good boyfriendBlack man, 31 needs good boyfriend Black Daddy in Chicago area Man, I don't know what I am supposed to say here lol....I am Frank and I am 31, clean, fit and single. I am just recently out of a long term relationship with my ex boyfriend. I won't go into detail but we just drifted apart. Anyway, I'm ready to mingle! Locals only in t...
  • King of your heart waiting for you in ChicagoKing 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 ...
  • Crystal, 27 New to the areaCrystal, 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...
  • ๐Ÿ˜‡ ๐Ÿ† ๐Ÿ˜TRANNY COUPLE -Chicago- SHEMALE SWINGERS๐Ÿ˜‡ ๐Ÿ† ๐Ÿ˜๐Ÿ˜‡ ๐Ÿ† ๐Ÿ˜TRANNY COUPLE -Chicago- SHEMALE SWINGERS๐Ÿ˜‡ ๐Ÿ† ๐Ÿ˜ Hey babe, are you interested in Shemale or Transsexual Sex? How about a shemale couple looking for you to join? If you want to have some sex and swing with us.. You MUST be willing to do whatever we say. Do you want to play with our cocks and boobies at the same time?. Swap TS Nudes & Conta...
  • Scads of Ads Here, But IScads of Ads Here, But I'm SPECIAL - That's What Momma ALWAYS Tells Me... Single and Special in Chicago I'm Rhianna still a bit of a goth at heart and trouble always seems to find me somehow. For now I still call Chicago home, but would like to see more of the world and find a hot guy. A guy who is SPECIAL just like me ๐Ÿ˜Š If you are a fun lovin rebel in need of a speci...
  • ๐Ÿ‘๐Ÿ‘๐Ÿ‘ Tight backdoor action ๐Ÿ‘ Deep Anal Sexiness ๐Ÿ‘๐Ÿ‘๐Ÿ‘๐Ÿ‘๐Ÿ‘๐Ÿ‘ Tight backdoor action ๐Ÿ‘ Deep Anal Sexiness ๐Ÿ‘๐Ÿ‘๐Ÿ‘ FREE Sex Finder Service! We get you LAID, gaurunteed. We do all the hard work for you. Getting laid has never been easier. This Is How It Works: 1. You enter your email. 2. You get a FREE list of women in Chicago who are "down to fuck" right now. 3. You contact these horny women and get laid to...
  • Ranch owner and lonely olRanch owner and lonely ol' guy Male Ranch Owner Seeking Woman in Chicago Ok, I ain't that old. Just turned 48. I am a ranch owner with 40 acres and am looking for a gal who is adventurous, outdoorsy, fit and healthy enough for horseback riding, hiking, biking and picnicking on the trails. Enjoy travel and new experiences? Me too...
  • Shy 41 yr old guy Shy 41 yr old guy Shy But Romantic in Chicago Hey ladies, I am Bryan, 41 and I am a little shy when it comes to meeting women. I am romantic and thoughtful and looking for a kind hearted woman. They tell me I'm handsome. I'll let you be the judge of that. what I do know is that I like to have fun and I'd love to mee...
  • Lesbian Biker Babe Seeking Female Travel Companion in Chicago...Lesbian Biker Babe Seeking Female Travel Companion in Chicago... I'm Brit - Hi! If you are like me then you love to ride and travel and experience life to the max. You have passion for the things you love, and you love a lot. You are high on life and can't get enough. You see the positive and don't have time for the negative. If this is you then I REALLY want to ...
  • My body yearns to be the center of your attention...My body yearns to be the center of your attention... Hi all you sexy men out there in Chi-town! I'm a horny White female looking for NSA sexual encounters of the lingering and passionate kind. I don't want just wham-bam thank you m'am type hookups. I want you to worship my body like you mean it and pamper me. Fix your studying gaze upon me when I'm na...
  • Hey, fella: Not getting your needs met? Me neither. LetHey, fella: Not getting your needs met? Me neither. Let's get together. I want to date someone who is equal and wants to please and be pleased. Let's feel the passion again. Sorry, no strings at the moment because my situation is complicated. Within 10 miles of Chicago area please. I have a somewhat flexible schedule but an out-of-town hookup just isn't in the cards.&nb...
  • KINKY KENNY FOR HOT MALE-ON-MALE ๐Ÿ˜ˆKINKY KENNY FOR HOT MALE-ON-MALE ๐Ÿ˜ˆ Horny Man Wanted in Chicago ๐Ÿ˜ˆ I'm Kenny, a horny gay man from Chicago who is on the hunt for some wild and kinky adventures with a local area guy. I love getting down and dirty, exploring all kinds of sexual acts and fetishes. I enjoy giving and receiving blowjobs, rimming, playing with dildos, ...
  • II'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...
  • Secret Lovers ...๐Ÿ’โค๏ธ๐Ÿ˜˜ Shhh DonSecret Lovers ...๐Ÿ’โค๏ธ๐Ÿ˜˜ Shhh Don't tell my husband My Husband doesn't like to get wild like I do. I want to have super sexy fun!! ๐Ÿคฉ๐Ÿคฉ Discreet Messages - Private Message ๐Ÿ’Œ 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 ...
  • Chicago๐Ÿ’• Letโ€™s Grab Drinks & See Where the Night Takes UsChicago๐Ÿ’• Letโ€™s Grab Drinks & See Where the Night Takes Us  Lesbian Lady here, seeking a fun and outgoing lady!!... Oh hey babe, I’m a sweet little flirt, I'm from Chicago and I like cute cocktails, deep convo and  making out in the back seat secretly. So I think we should meet at a cozy lounge or rooftop  bar and get a strong drink or ...
  • Hey YaHey 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...
  • T-Girl Wants No Strings Fun in Chicagoland!T-Girl Wants No Strings Fun in Chicagoland! Hi I'm Mavin, and verybody says I look like Marlo Thomas an actress from the 1960's and 70's. I'm passible, functional, Ive been described as easy to talk to, comfortable to be around, and sweet in demeanor. I'm a good girl with needs though and want some NSA action in Chicago tonight. You...
  • Hey Sexy IHey Sexy I'm Gonna Add YOU to My Cart! Shopping Hard in Chicago Hi there I'm Roseanne about 22 years, about 5'5 and brunette with big brown eyes here in Chicago. You know girls love to shop online and I'm no different. I'll just add you to my cart and check you out. Now how long until delivery? Huh? I don't do snail mail, so make it qui...
  • Spicy and Hot T-Girl from ColombiaSpicy and Hot T-Girl from Colombia Latina T-Girl in Chicago Hey guys, I am Colleen and I am looking for a long term relationship. I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery. Nice surpise waiting for you! Send me a private message! ColleenLatinaT...
  • Hey Swingers - Come Give Granny Some Sugar!...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! ...
  • The Trevor Project Saves Young LGBTQ+ LivesThe 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...
  • I am Caroline and I am lonelyI am Caroline and I am lonely Caroline Seeks Female in Chicago  Hey ladies, I'm Caroline. I have only been living in the Chicago area a couple months and as you can imagine I have not had much chance to meet other women. If you are lesbian, bisexual or bi-curious and want to meet me please send me a message and see my...
  • Here I am! Hookup with a smoking hot grandma in Chicago!Here I am! Hookup with a smoking hot grandma in Chicago! You might not think so but older women still love having sex. Come check me out and see why women get better with age! I'm gonna show you what you don't know now. I'm Sherri a retired teacher and school administrator in Chicago. My friends are all settled down and traveling in their RV's, but NOT ME...
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  • Hey ladies, I am Roger, 49 and looking for real loveHey ladies, I am Roger, 49 and looking for real love Man Seeking Woman for Dating in Chicago Hi, my name is Roger. I'm here seeking a woman for dating and friendship - hopefully a lot more! I am 49, a professional with no kids and no personal entanglements. I am local to this area and have lived here for 22 years. I would love to meet a kind a funny ...
  • I Need an Interesting Man in Chicago...I Need an Interesting Man in Chicago... An active imaginative and educated mind stimulates me. I'm Howie, 37 yrs, 5'11, 180 pounds, shaved head, not so attractive, keep to myself a lot, accountant and lover of all things novel and interesting. The world is full of so many fascinating things that I want to soak it all up. If you feel this ...
  • Jaw Dropping Hot LesbianJaw Dropping Hot Lesbian Hot Lesbian Seeking a Female Lover in Chicago Did that get your attention? I hope so because I am looking for my perfect female partner. Someone fun attractive and intelligent. She should be easy to talk to, fun loving, laid back and attentive to her partner, just as I am. I'm looking forward to ha...
  • Bi-Curious Female in Chicago...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 ...
  • What songs make you dance?What songs make you dance? Are you the Stayin Alive type? the Twerker type? Currently looking for a Chicago girl and I love a girl with rythm and groove who knows how to get down. I am not the shy type and some would say extroverted. I love a good time as much as anyone, but also enjoy chillin and bein with my boo. If this is...
  • Letโ€™s Flip the Scriptโ€”You Lead, Iโ€™ll Moan ๐Ÿ˜๐ŸŽ€ChicagoLetโ€™s Flip the Scriptโ€”You Lead, Iโ€™ll Moan ๐Ÿ˜๐ŸŽ€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. ๐Ÿ’ซSwap 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...
  • Busty curvy 38DD wants to date gorgeous guyBusty curvy 38DD wants to date gorgeous guy Busty, Curvy 38DD W4M Fun, busty, sexy woman looking for an equally sexy guy to make me happy, both physically and spiritually. Discretion assured. Please be fun. I will be your dream girl! Text message me (BustyKateX) for a date....
  • Looking for the real thingLooking for the real thing Sexy Hookup in Chicago I am told I am very sexy, but that is for you to decide. I am short, great body, confident and intelligent and would like to meet a Chicago guy for fun conversation and anything else that happens. I'm an internet junkie, love texting and sexting! I have a lot of pics and vide...
  • Keep Calm And Have A Threesome in Chicago!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...
  • BDSM Master Taking on New Female Slaves...BDSM Master Taking on New Female Slaves... I am single minded strict, controlling discipline oriented Master in Chicago 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 more...
  • Looking 4 a Man 4 Sex ๐Ÿ†๐Ÿ’ฆ & Fun๐Ÿ˜๐ŸคฉLooking 4 a Man 4 Sex ๐Ÿ†๐Ÿ’ฆ & Fun๐Ÿ˜๐Ÿคฉ I really need to get out and have some fun, maybe a drink, smoke.. Sex -  Message Meโค๏ธ 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...
  • Chicago BDSM Master Taking on New Trans Slaves...Chicago BDSM Master Taking on New Trans Slaves... I am single minded strict, controlling discipline oriented Master in Chicago 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 more...
  • Super Hot Barbie for Chicago MaleSuper Hot Barbie for Chicago Male Hello!! My name is Phoebe and my intelligence and charming personality is sure to make you feel comfortable! I am just looking for a cool guy I can date around here and have some fun together! You want to meet me? Send me a message with your pics and number! @HotBarbieChicago...
  • Looking to be your slut all night longLooking to be your slut all night long FREE Sex Finder Service! We get you LAID, gaurunteed. We do all the hard work for you. Getting laid has never been easier. This Is How It Works: 1. You enter your email. 2. You get a FREE list of women in Chicago who are "down to fuck" right now. 3. You contact these horny women and get laid to...
  • Come tie me up and letCome 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...
  • Fun Loving Couple in Chicago Seeks Male or Female for Threesomes...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...
  • Swingers - Estella Wants Threesome - Live La Vida Loca!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...
  • ๐Ÿ”ฅ Savor Sensual Delights with a Curvy Cutie in Chicago! ๐Ÿ”ฅ๐Ÿ”ฅ Savor Sensual Delights with a Curvy Cutie in Chicago! ๐Ÿ”ฅ BBW in Chicago, IL - Looking for Love Tonight!! Seeking a woman who embraces her curves and sets your passions ablaze? Look no further! I'm a BBW beauty in Chicago, overflowing with warmth and sensuality, ready to sweep you off your feet. View My Pix and Message Me - Imagine indulging in tantal...
  • Mixed Race Male Seeks Sexy Female for FWB in Chicago...Mixed Race Male Seeks Sexy Female for FWB in Chicago... Hi there ladies I'm James new to Chicago and I want to meet you. I've been divorced for about a year now. Not really wanting to dive in too deep just yet, but you never know what will happen in the future. I need a sexy more mature woman who can relate to me in terms of life experiences and life les...
  • SUGAR DADDY ๐Ÿญ๐Ÿ‘จโ€๐Ÿฆฐ ๐Ÿ’ฆLooking 4 Play Boy M4M SUGAR DADDY ๐Ÿญ๐Ÿ‘จโ€๐Ÿฆฐ ๐Ÿ’ฆLooking 4 Play Boy M4M Hey there babe, I'm a 25 year old male who is searching for another guy to play with and spoil. I'm strong and muscular, I drive a beautiful car, I can take you to do things you've always desired ๐Ÿค‘ It turns me on so damn much to find a cute little man to play with and take care of. Let me be D*dd...