Chicago, Illinois Sex Ads and Adult Classifieds

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  • May 26th, 2025
  • Mark, 33 Love country music and driving my truckMark, 33 Love country music and driving my truck Hey, the name is Mark and I am a country boy now living in Chicago, age 33, a mechanic and I love to drive my truck out on the open roads. Sometimes I take a blanket and a beer and hang out at my favorite lake a few miles from my house in the Chicago area. I am self sufficient and I am wanting to me...
  • ยฟHablas espaรฑol? Hello good to meet you.ยฟHablas espaรฑol? Hello good to meet you. Dulce amante esperando para probar su piel. ¿Puedes leer esto? ¿Hablas español? Quiero hablar contigo. Envíame un mensaje @DulceXAmante. I speak English, Spanish and some French. I want to meet you my sweet princess. Female or trans women only. No men. Woman for woman in...
  • Hot Angel brand new to Chicago and web dating.Hot Angel brand new to Chicago and web dating. Outdoorsy girl. I can be your hottest fishing buddy! Ok, I guess I am doing this right and I am hoping someone sees this! I am 28 and want to meet a cool guy who likes outdoorsy activities like hiking and (unbelievably) fishing! Yes, I can even hook a worm! Want to meet and hang out with me?  ...
  • Gay Body Rubs - Need Sexual Relief? - Yeah, You Need SAL!...Gay Body Rubs - Need Sexual Relief? - Yeah, You Need SAL!... Sal here in Chicago to melt your stress away and relieve that pent up sexual tension like no other. I host and offer full amenities and services to my gay clients. All men are welcome as well as couples who need to unwind and spice up the day the right way. I serve gay, bixsexual and bi-cu...
  • I Need a Chicago MILF WhoI Need a Chicago MILF Who's Got That Sexpertise! Chicago Man Needs Experienced Woman Hi all you hot mommas out there in Chicago. I'd love to meet someone to hookup with on a regular basis. FWB style. Young women my age seem to be sort of squirrely and awkward in bed. (just my experience) I picture a MILF as being more focused and educated on matt...
  • 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...
  • Russian sweetie looking for sexy loveRussian sweetie looking for sexy love Sweet Russian Woman in Chicago Hello. I am new to Chicago and would like to make some friends and meet nice people. I am looking for a wonderful guy to go to dinner with. I hope you don't mind my accent. I am working on it but I speak good English. Would you like to meet me? If so, text me onl...
  • FEELING H0RNY? IFEELING 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...
  • Roses are Red, Violets are BOOBS!Roses are Red, Violets are BOOBS! Woman Seeking Boob Man in Chicago I'm Violet! Just a girl living here in Chicago all my life except for a short time in Tucson, AZ. I'm 23 years old, big natural titties, redish hair, blue eyes, big sexual appetite and love to have a man treat me to a long blissful booby rub. That gets me hot ...
  • Any Sexy Couples in Chicago Want to Hookup? - Asking for a Friend ๐Ÿ˜„Any Sexy Couples in Chicago Want to Hookup? - Asking for a Friend ๐Ÿ˜„ Inquiring on Threesome in Chicago I'm really horny, I mean I'm really Hannah here in Chicago and you see there's this very close little friend of mine who is bored and lonesome. She wants to know if there are any hot swinging couples around that might be kind enough to service her once in a while. ...
  • Looking for Mr. Goodbar...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....
  • Czech Beauty new in ChicagoCzech Beauty new in Chicago Ahoj, lásko. Rád bych se s vámi setkal a hledal jsem vás. Kdy se s tebou m?ลพu setkat? Jsi tam venku? Kontaktujte m?. Hello, my love. I know you are out there somewhere. I would like to meet you and have been looking for you.  I like texting and sharing sexy thought...
  • II'm Troy in Chicago - Bi-Curious Looking to Experiment... Bi-curious in Chicago Hi guys, I'm Troy here in Chicago divorced after 10 years and am entertaining the idea that I might like the gay lifestyle. So, here I am on this site looking for a special kind of man who isn't going to go too fast with me. (is patient) Woman say I'm well hung, but ...
  • Hungry for Explosive Sex, Fun and Adventure?...Hungry for Explosive Sex, Fun and Adventure?... Yeah, me too honey! I'm Hope, a black trans woman living in Chicago with all the skills to thrill. Vers top or bottom and love hot sex anyway you can get at it. Im curious, smart, free spirited, and funny. I love to travel, eat good food, watch movies and spend intimate time with my man, and no...
  • ShopinRound38 outgoing, funny, and independentShopinRound38 outgoing, funny, and independent (Please only message me if you live within 50 miles of the Chicago area) . I am winding my career down and am wanting to traveling more and work less. Looking for someone to share intimacy and good times with. It’s getting harder and harder to find someone the old fashion way, so thought ...
  • ๐Ÿ’– Sweet, Seductive & Craving Her โ€“ Ebony Babe Looking for a Good Time ๐Ÿ˜˜๐Ÿ’– Sweet, Seductive & Craving Her โ€“ Ebony Babe Looking for a Good Time ๐Ÿ˜˜ Chicago Ebony Lesbian Lover Seeking Woman!!๐Ÿ˜‰ I am a thick, chocolate colour ๐ŸŽ‚๐ŸคŽ  , in my mid-20s, with soft curves and  smooth skin, and a wicked little smile. I am playful, affectionate and very into women,  especially if they know how to tease and please.  It should be ...
  • Sexy young lesbo wanting to date sameSexy young lesbo wanting to date same Hi I'm Melodie! I am 19 and have been out to my family for 3 years. They are so cool and don't care as long as I am happy. My mom suggested I put an ad out online so here goes. Wait a minute... how does my mom know this site?!! hahah, anyway, here goes.  I am into clubbing but also like peace ...
  • THICK AND HARD๐Ÿ†โœ…right nowTHICK AND HARD๐Ÿ†โœ…right now Hi Guys ๐Ÿ˜‰ I'm Super Horny Tonight I'm in Chicago and willing to travel    My Pix and Profile    COCK SIZE -7INCHAge: 29 years oldName: LEXX ๐Ÿ˜ˆ๐ŸฅตGender: MALELocation: Chicago Availability: Incall & Outcall The Kind of Stuff I Want: ...
  • Join Me for an Episode of The Hung and The Restless!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...
  • Tall, Dark, Handsome LesbianTall, Dark, Handsome Lesbian My name is Selena and I am tall, dark haired, in my 40s and still in my sexual prime! I have Latin heritage and I am fiery but kind. I do not have a bad temper but I am passionate. Age doesn't matter as much as personality and spirit. Any race, any height/weight. I love all body types as long as you...
  • Hello guys, looking for a boy friendHello guys, looking for a boy friend So, my name is Talia from the Chicago area and I am completely new to this online hookup stuff. I have never put an ad in a website before so I hope I am doing this right! If you would like to speak with me or arrange a date you can check out my profile @Talia4bf here and let's swap some sexy p...
  • Tall & Peggable ๐Ÿ˜ˆ๐Ÿ’‹ Looking for My Boss BabeTall & Peggable ๐Ÿ˜ˆ๐Ÿ’‹ Looking for My Boss Babe Hi I am a Single 32 years old straight white male.I'm in Chicago and I would love to meet and amazing woman who wants to feel a real man! ๐Ÿ˜‰ I love lots of foreplay, kissing , giving and receiving lots of orgasms. I am very oral i love to give as much as receive. I love to make her cum all ov...
  • WE CAN HOST OR COME OVER ๐Ÿ’ฅChicago๐ŸŒŸ๐Ÿ˜‰WE CAN HOST OR COME OVER ๐Ÿ’ฅChicago๐ŸŒŸ๐Ÿ˜‰ 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.&...
  • Sophisticated Black/White mixed Lady wanting Gentleman friend in ChicagoSophisticated Black/White mixed Lady wanting Gentleman friend in Chicago My name is Janette and I am 32. Some men have been intimidated by my 36D breasts, with big sensitive nipples, but I am hoping there is a man out there who can cope with them! I am passionate and responsive and give pleasure just as freely as I receive. Don't be afraid, I don't bite... too hard! Mes...
  • Ebony Beauty Seeks Her Princess in Shining Armor in ChicagoEbony Beauty Seeks Her Princess in Shining Armor in Chicago Ebony Beauty Seeks Chicago Princess in Shining Armor My name is Cheryl and this is my first time ever posting a dating ad. You can't imagine how nervous I am putting myself out there! It's terrifying! lol.... but here goes. I am medium height and build. I have great tits so if that's your thi...
  • Sex Hookup In ChicagoSex 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...
  • 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...
  • 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 ...
  • Femme looking for FemmeFemme looking for Femme Femme for Femme in Chicago Hi, thanks for looking at my ad. My name is Kari. I'm femme, looking for femme. I love make-up and dresses and I want to share my world with a hot chick who likes the same. I recently upgraded my car, so let's go for a ride! I am currently studying dentistry and work two...
  • Jon Boy seeking Chicago Top Male to Pleasure ๐Ÿ‘…๐Ÿ†๐Ÿ’ฆJon Boy seeking Chicago Top Male to Pleasure ๐Ÿ‘…๐Ÿ†๐Ÿ’ฆ Kink friendly bottom male Hey, thanks for checking my ad. I'm Jon Boy, looking for a hot gay man who's ready to play with me and let me explore all kinds of naughty fun as I pleasure you. Recently out gay male, age 21, seeking other gay, bisexual or bi-curious guys for some wild male-on-male action...
  • DIVORCED๐Ÿ‘ฉMOM/MILFDIVORCED๐Ÿ‘ฉMOM/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. ๐Ÿ˜˜ I have nasty videos for sell๐Ÿ’‹ I'm 42 Years ๐Ÿ…ณ๐Ÿ…ธ๐Ÿ†…๐Ÿ...
  • LetLet's Play Cock, Paper, Scissors!... Gay Man Looking for Fun in Chicago Now that I got your attention. Hi I'm Graham, a gay man here in Chicago and I'm looking for a man who likes to play sexually charged games. I'm 28 years old, black hair, brown eyes, 6'0, well endowed, (8+inches) hispanic, single, love to party, no pets, ...
  • Chicago Gamer Seeks Female Gamer for Dating and Fun...Chicago Gamer Seeks Female Gamer for Dating and Fun... Hey let's join forces and level up together. I'm a bit of a nerd and have an outgoing personality. (very social) I'm Denny, 23 years old, 6'0, 200 pounds, blonde hair, blue eyes, love gaming and my cat Sam. About my girl: She should be from Chicago, love gaming or at least be okay with it, be smart,...
  • WhereWhere's My Sexy Marlboro Man?!... To me a sexy man who smokes is hot AF. Hi, I'm Hannah living in the Chicago area wanting to meet a single male smoker. I'm 24 years old, Auburn hair, 5'7, curvy with 36C boobs, blue eyes, smoker and want to smoke when you are eating me. You may have figured out that I have a fetish for smoking, beca...
  • Italian sweetie looking to taste your fruitItalian sweetie looking to taste your fruit Woman seeking woman in Chicago Amante dolce in attesa di assaggiare la vostra pelle. Riesci a leggerlo? Parli italiano? Voglio parlare con te. Inviami un messaggio @DolceAmante. I speak English too! Sweet lover waiting to taste your skin. I want to talk with you. Send me a message @DolceAmante. S...
  • Girls on The Goth Side Get My Blood Pumping...Girls on The Goth Side Get My Blood Pumping... Hi I'm Derek, 24 years old, 5'11, 180 pounds, black hair, hazel eyes, as it stands, I'm a bit anti-social. I have broad sexual tastes ranging from the vanilla to BDSM and enjoy fantasy play and trying new things. I need a dark Chicago girl who knows what the Goth scene is all about. Bloodsuckas...
  • Looking for some fun ๐Ÿ’ฆ๐Ÿ’ฆ๐Ÿ’ฆLooking for some fun ๐Ÿ’ฆ๐Ÿ’ฆ๐Ÿ’ฆ 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...
  • ChicagoChicago's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Chicago Hi you sexy man! I'm Toni a trans woman from here in Chicago. Looking forward to a fun, sexy evening with you tonight. Let's make some memories that we'll never forget! I'm a 28 year old redhead tgirl who's passionate, warm, funny, hung, functional and loves...
  • Lesbian horse lover wants to meet sameLesbian 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...
  • ๐Ÿ’ŽPARTY & SEXX๐Ÿ’Ž๐Ÿ’ŽPARTY & SEXX๐Ÿ’Ž So I really need someone to take me out and show me the ropes. I do want to have some fun and let loose. Will you help me celebrate? ๐Ÿ“ธ My Pictures - I hope you like what you see. If you do let's meet up and have some sexy fun! HOT GIRL NEEDS OUT ๐ŸŽ‰๐Ÿฅณ Let's drink, party and hookup&n...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Chicago My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. This feels right and I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and oth...
  • ๐Ÿ’Ž Adorable Sugar Baby ๐Ÿ’Ž Seeking his Generous King ๐Ÿ‘‘๐Ÿ’Ž Adorable Sugar Baby ๐Ÿ’Ž Seeking his Generous King ๐Ÿ‘‘ ๐Ÿ“  Location: Chicago    Seeking: A kind/dominant daddy๐Ÿ‘‘  A Little about Me: Hello everyone! I am a sweet, fit blonde with a flirty nature  and an appreciation for the good things in life. I enjoy being pampered, looked after and treated  like a king. If you a...
  • Asian Lilly ๐Ÿ‘ฉโ€โค๏ธโ€๐Ÿ‘จ IAsian Lilly ๐Ÿ‘ฉโ€โค๏ธโ€๐Ÿ‘จ I'm Horny Tonight Looking for a genuine sexual relationship with a like-minded asian lady? ( Do you want to view my personal profile and my sexy pictures? ) Look no further! As an Asian woman, I value deep sexy connection and meaningful fantasies.. I'm seeking a man who shares those same values and is open to explori...
  • ๐Ÿ’‹ Naughty or Nice? I Can Be Both ๐Ÿ˜ˆ KINKY BDSM W4W๐Ÿ’‹ Naughty or Nice? I Can Be Both ๐Ÿ˜ˆ KINKY BDSM W4W Woman Seeking a sexy lady in Chicago... I want to know your KINKS๐Ÿ’ฏ๐Ÿ˜ˆ I'm really into fantasy play and BDSM. I love to DOMINATE or be submissive.. I love role playing and have lots of fun!!  I need a beautiful girl for tonight to match my energy ๐Ÿ’– I’m sweet on the  outside, wi...
  • LookinLookin' for a Playmate? Let's Make a Playdate!... Sexy Chicago Hottie For NSA Busy student wants a hot and sexy man (preferably a little older and mature) to spend some quality time with in Chicago. I'm a 22 year old white female college student studying hospitality management and love to get out and find a release once in a while with more mature...
  • 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...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in ChicagoSECRET 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...
  • ๐Ÿ’ฏreal gfe service๐ŸŽ€kiss๐ŸŽ€bbbj๐ŸŽ€squirting๐ŸŽ€rim๐ŸŽ€cim๐ŸŽ€b2b๐Ÿ’Ž Chicago ๐Ÿ’Ž๐Ÿ’ฏreal gfe service๐ŸŽ€kiss๐ŸŽ€bbbj๐ŸŽ€squirting๐ŸŽ€rim๐ŸŽ€cim๐ŸŽ€b2b๐Ÿ’Ž Chicago ๐Ÿ’Ž Hey there, I'm Cher from Chicago, and I am looking for a sexy and adventurous playmate to explore all of our kinks together. I love nothing more than getting down and dirty in the bedroom, trying out new positions and pushing boundaries. If you want to see more of me before our encounter, check out ...
  • No strings fun - my place preferredNo strings fun - my place preferred 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...
  • I will always laugh at screaming goats...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...