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  • October 25th, 2025
  • Looking for a local woman who loves to fuck, suck, and playLooking for a local woman who loves to fuck, suck, and play I never thought I'd be writing one of these ads, but here I am. My name is Ian and I'm a man seeking a local woman in Chicago, Illinois for great sex, adventure, and fun. You can find me in the FreeSexAds.com dating profiles under username ianchic49223. I love exploring all kinds of sexual acts a...
  • Looking for a Connection in the Windy City! 🌬️ Hey there, fellow Chicagoans! My name is Bearnard and I'm on the lookout for someone special to share some amazing moments with. 🌈 So, let me tell you a bit about myself. I'm an easygoing guy who loves to embrace life's adventures. 💪🏼 Despite not being built like a bodybuilder, I've got ...
  • Lindsey 💋💋💋 EARLY morning Sex Sessions 💋💋 SEXY MILF ❌❤ HOT MILFLindsey 💋💋💋 EARLY morning Sex Sessions 💋💋 SEXY MILF ❌❤ HOT MILF HOT MILF FOR EARLY MORNING SESSIONS 💋💋  Have you ever felt a sensation that makes your whole body shudder? Would you like to experience this feeling again and again? Me too!! Touch is the most incredible gift you can give or receive from someone. You need it, and I need it too, come and ...
  • Brandon the Stud for Sex on the SideBrandon the Stud for Sex on the Side Male for Male in Chicago, Illinois Hi guys. I'm Brandon. I work out regularly and take good care of my body. I'm active and STD free. Looking for M4M fun. I do stripping, lap dances and offer full service to make you feel good all over. Top or bottom. 9" cut. Hot bod.  Check out my featured C...
  • Fuck me like you mean itFuck me like you mean it I'm a man seeking a local woman for great sex, adventure, and fun. I love to explore all kinds of naughty things in the bedroom. From passionate kissing to rough play, I enjoy it all. I'm not afraid to get a little wild and try new things. Whether it's giving or receiving blowjobs, playing with t...
  • Fuck Me Hard and Make Me Cum ErwinFuck Me Hard and Make Me Cum Erwin Hey ladies, I'm Erwin from Chicago, Illinois. I'm a man seeking a local woman for some great sex, adventure, and fun. I love to get down and dirty in the bedroom and explore all kinds of kinky fetishes. From giving sloppy blowjobs to getting my tight ass pounded, I'm up for anything that brings us b...
  • Lipstick lesbian 💋 looking for lips to practice on   Lipstick lesbian 💋 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 ...
  • Fuck Me Hard and Make Me Squirt EverywhereFuck Me Hard and Make Me Squirt Everywhere I'm a naughty girl from Chicago who loves to get down and dirty. My name is Ida , and I can't wait to explore all your wildest fantasies with you. When it comes to sex, I'm open-minded and always up for trying new things. I love giving sloppy blowjobs and feeling your cock deep in my tight pussy...
  • Chubby Chick looking for guy who can handle me!Chubby Chick looking for guy who can handle me! Chubby Looking for Dates in Chicago So, I am a little heavy but mostly 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 message me your favorite joke and we can see how we get along!  Send your pics and contact # for mine. ...
  • Looking for a Woman to Fulfill My Wildest FantasiesLooking for a Woman to Fulfill My Wildest Fantasies I'm Torre, a man seeking a local woman in Chicago, Illinois for some mind-blowing sex, adventure, and fun. I love exploring all kinds of sexual acts and fetishes with the right partner. From passionate kissing to rough fucking, I enjoy it all. I love giving and receiving blowjobs, eating pussy unt...
  • 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. Not all the time, but you need a good sense of humor. Life is too fun to be serious all the time. Message me ...
  • Hot Chicago guy waiting for girl of my dreamsHot Chicago guy waiting for girl of my dreams Black Man in Chicago for Romantic Woman Dark cholocate 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 @DwayneS...
  • 🌷 Absolutely A Doll 🌷 Your Perfect Asian Princess 🌷🌷🌷🌷 Absolutely A Doll 🌷 Your Perfect Asian Princess 🌷🌷🌷 Sexy Asian Girl Available in Chicago I am Choko @ChokoSexyBusty (my profile and pics), age 21. I am Asian girl Sexy Busty girl with 36D-25-35, 108 lbs, amazing body with silk smooth skin, absolutely charming stunning... Time to relax ..... Time to unwind ..... Let me pamper you let me spoil yo...
  • Looking for a Naughty Girl to Fulfill My Wildest FantasiesLooking for a Naughty Girl to Fulfill My Wildest Fantasies Hey ladies, I'm Monty from Chicago and I'm on the hunt for a local woman who can handle all my dirty desires. When it comes to sex, I don't hold back. I love getting my cock sucked until I explode in your mouth 🍆💦, giving you multiple orgasms as you ride me like there's no tomorrow 🎢, and m...
  • 💕💕 SEXY 💋 PLAYFUL 💋 BLOND 💋 125Lbs💌 PAYMENT UPON ARRIVAL 💌💕💕 SEXY 💋 PLAYFUL 💋 BLOND 💋 125Lbs💌 PAYMENT UPON ARRIVAL 💌 Summer, Independent Escort in Chicago, Illinois Hey guys! I'm Summer, age 30, blond hair, green eyes, I'm hwp and I love to have a good time. Not down with the games & BS so let's have some fun and get you off. I know that's what you came here for! PM or text me @SummerIndependent let's get nak...
  • Fuck me hard and make me scream for more <br> Chryste from Chicago wants to play dirtyFuck me hard and make me scream for more
    Chryste from Chicago wants to play dirty
    I'm a naughty girl looking for some hot and steamy fun in the Windy City. I love getting down and dirty, exploring all kinds of kinky fantasies. From rough sex to sensual massages, I'm up for anything that will leave us both satisfied. When it comes to sex, I enjoy being on top, riding you like t...
  • Passionate Lesbian Seeks Orgasms, Oral Sex, and Tight Ass PlayPassionate Lesbian Seeks Orgasms, Oral Sex, and Tight Ass Play I'm Rayna from Chicago, and I'm looking for a local lesbian, bisexual or bi-curious woman who wants to have some hot and steamy fun with me. I love exploring all kinds of sexual acts and fetishes with another woman. From passionate kissing to intense orgasms, I want to experience it all with you....
  • Get Lost in Love with Murial from Chicago!Get Lost in Love with Murial from Chicago! Hey there! I'm Murial, a fun-loving gal from the Windy City looking to meet someone special. I may not be a supermodel, but my curves will definitely catch your eye. I'm a mix of Italian and Irish, so you know I've got that fiery passion and luck of the Irish on my side 😉 I love exploring new ...
  • Passionate Lesbian Seeking Orgasms, Oral Sex, and Tight Ass PlayPassionate Lesbian Seeking Orgasms, Oral Sex, and Tight Ass Play Are you a woman who craves hot and steamy encounters with another woman? Do you fantasize about exploring every inch of a woman's body, making her scream with pleasure? Well, look no further because I'm Krissie from Chicago, Illinois, and I'm here to fulfill all your wildest desires. I'm on the h...
  • Super Hot Barbie for Chicago MaleSuper Hot Barbie for Chicago Male Hot Barbie in Chicago, Illinois 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! @Ho...
  • Charming Chicago Guy Looking for a Fun Date!Charming Chicago Guy Looking for a Fun Date! Hey there! I'm Manuel from the Windy City, and I'm on the lookout for someone special to spend some quality time with. Whether it's grabbing a slice of deep-dish pizza at Lou Malnati's, catching a Cubs game at Wrigley Field, or taking a stroll along the beautiful Lake Michigan waterfront, I'm up f...
  • Passionate Lesbian Seeks Orgasmic EncountersPassionate Lesbian Seeks Orgasmic Encounters Are you a woman who loves exploring every inch of another woman's body? Do you crave the taste of sweet, wet pussy on your lips? Well, look no further because I'm Gwennie from Chicago, Illinois, and I'm here to fulfill all your wildest fantasies. I'm looking for a local lesbian, bisexual, or bi-c...
  • Passionate Lesbian Seeking Orgasmic EncountersPassionate Lesbian Seeking Orgasmic Encounters Are you a lesbian or bisexual woman in Chicago looking for some hot and steamy fun? Look no further, because Harmony is here to fulfill all your wildest fantasies. I love exploring every inch of a woman's body, from sensual massages to toe-curling orgasms. I'm into everything from oral sex to an...
  • Unleash Your Inner Fire with Julianna from ChicagoUnleash Your Inner Fire with Julianna from Chicago Hey there, potential flame! My name is Julianna, and I'm on the hunt for someone who can handle my sizzling personality. 🔥 Living in the heart of Chicago, Illinois, I bring a unique blend of passion and excitement to every date. Now, let's get one thing straight: I'm not your average girl-next...
  • Exploring Chicago with a Dash of RomanceExploring Chicago with a Dash of Romance Hey there, I'm Wilton from Chicago! I'm a fun-loving guy who enjoys exploring the local art scene and trying out new restaurants. Whether it's checking out the latest exhibit at the Art Institute or grabbing a slice of deep dish pizza at Lou Malnati's, I'm always up for an adventure. If you're l...
  • Looking for a Tight Pussy to Ride and Gag on My Huge CockLooking for a Tight Pussy to Ride and Gag on My Huge Cock I'm a man seeking a local woman in Chicago, Illinois for some great sex, adventure, and fun. I love all kinds of kinky stuff like anal play, sloppy blowjobs, and deep throating. I get off on making a woman cum over and over again until she can't take it anymore. I want to explore your wildest fan...
  • Unleash Your Wild Side with Theresa from ChicagoUnleash Your Wild Side with Theresa from Chicago Hey there! I'm Theresa, a fun-loving gal from the Windy City looking to spice up my love life. I may not be a supermodel, but I've got curves in all the right places and a smile that can light up a room. If you're into trying new things and exploring the city, then I'm your girl! I love checking ...
  • Spanish Gigolo for hireSpanish Gigolo for hire Hola, I am waiting for you to want to date me. You see my pictures and you like me, so call me for date. Juan Carlo, 28, handsome....
  • Fuck Me Hard and Deep in ChicagoFuck Me Hard and Deep in Chicago I'm a horny gay man looking for some hot male-on-male action. My name is Shawn and I want to find guys who are into all things dirty and kinky. I love getting my cock sucked and my ass played with. I enjoy rimming, anal, role play, bondage, and using toys like dildos. I'm also open to trying new ...
  • Young, Free and Single in ChicagoYoung, Free and Single in Chicago Lonely in Chicago You have got be out there somewhere! I am lonely and I would love to find a funny and happy-go-lucky guy who can be my best friend and lover. I'm hoping you look good in a cowboy hat and jeans! View my profile and private pics @LonelyinChicago so we can at least swap pics and get ...
  • Nice but Naughty 30 year old seeking affection and a good timeNice but Naughty 30 year old seeking affection and a good time Naughty30luv in Chicago, Illinois Hey, I'm Monica. I am half Latina and half European and moved here recently. I am lonely and would like to meet a nice man who wants to play and enjoy life together. Message me @Naughty30luv for pics and to book a date! (Naughty30luv) I'm naughty but nice, love a ...
  • Looking for Love in the Windy City Hey there! My name is Kelsey and I'm on the hunt for a special someone to share some amazing moments with. 🌈❤️ I'm a proud gay man living right here in Chicago, Illinois. Let me tell you a little bit about myself! Physically, I have a body that's as unique as my personality. You'll find me...
  • Get to Know Bernie from Chicago!Get to Know Bernie from Chicago! Hey there! I'm Bernie, a straight guy from the Windy City looking for someone special to hang out with. I love trying new restaurants in Wicker Park, catching a game at Wrigley Field, or grabbing coffee at one of the cute cafes in Lincoln Park. If you're into exploring the city and having fun, the...
  • Get Lost in the Windy City with KrissyGet Lost in the Windy City with Krissy Hey there! I'm Krissy, a fun-loving gal from Chicago, Illinois. I may not be your typical girl next door, but I guarantee you'll have a blast hanging out with me. Whether we're grabbing deep dish pizza at Lou Malnati's, sipping cocktails at The Aviary, or catching a Cubs game at Wrigley Field, I'l...
  • October 24th, 2025
  • Looking for a Local Woman to Fulfill My Wildest FantasiesLooking for a Local Woman to Fulfill My Wildest Fantasies I'm a man seeking a local woman in Chicago, Illinois for some mind-blowing sex, adventure, and fun. You can call me Jethro. I'm not looking for anything serious, just someone who's down to get dirty and have a good time. I love exploring all kinds of sexual acts and fetishes. From passionate kiss...
  • Fuck Me Hard and Deep - VaughanFuck Me Hard and Deep - Vaughan's Raunchy Gay Male Ad Looking for a hot gay man who loves to get down and dirty in the bedroom? Well, look no further because I'm your guy! My name is Vaughan and I'm a horny gay man from Chicago, Illinois who is seeking other gay, bisexual or bi-curious guys for some steamy male-on-male fun. I love everything from s...
  • Fuck Me Hard and Deep - SpenserFuck Me Hard and Deep - Spenser Are you a horny gay man looking for some hot male-on-male action in Chicago? Well, look no further because I'm your guy! My name is Spenser and I'm a kinky dude who loves to suck cock, get my tight ass pounded, and explore all kinds of wild fetishes. 🍆👅💦 I'm into everything from sloppy b...
  • Passionate Lesbian Seeks Tight Ass for Orgasms and Oral Play<br>Passionate Lesbian Seeks Tight Ass for Orgasms and Oral Play
    I'm Shena, a hot and horny lesbian from Chicago looking for a local woman who's ready to get down and dirty with me. I love exploring all kinds of kinky fetishes and sexual acts with other lesbian and bisexual women. From sensual oral sex to intense ass play, I'm always up for some fun in the bedr...
  • 24 y/o Bartender for No Strings Fling24 y/o Bartender for No Strings Fling No Strings Fling in Chicago Hi! I am Kimberly and I am 24! I have a loveless marriage. My job is fun and I love my customers. Some of them flirt but they are just my customers. I want to meet a sexy guy who will be kind and attentive and loving! You must be out there somewhere! Contact me me if yo...
  • Cum Ride My Tight AssholeCum Ride My Tight Asshole I'm Vonni, a naughty girl from Chicago who loves to play with toys and get down and dirty. I enjoy being on top, riding cock until I cum all over it. I also love giving sloppy blowjobs and getting my pussy licked until I squirt all over your face. If you're into some kinky fun, I'm your girl. I ...
  • Fuck Me Hard and Cum in My Tight AssFuck Me Hard and Cum in My Tight Ass I'm a horny gay man from Chicago looking for some hot male-on-male action. I love getting my ass pounded and feeling a throbbing cock deep inside me. I also enjoy giving sloppy blowjobs and gagging on a huge dick. If you're into playing with dildos, I'm all for it. Let's explore our wildest fanta...
  • Chicago Man Seeking Woman for Wild and Raunchy FunChicago Man Seeking Woman for Wild and Raunchy Fun I'm a guy who loves to get down and dirty in the bedroom. I'm looking for a local woman who can keep up with my insatiable appetite for sex and adventure. My name is Stevie, and I can be found on FreeSexAds.com under the username steviech46803. I enjoy all kinds of sexual acts, from giving and re...
  • LetLet's Explore Chicago Together Hey there, I'm Woodie from Chicago! I love exploring the city by going on long walks along Lake Michigan or checking out the latest exhibit at the Art Institute. If you're into trying new restaurants, we could grab a bite at Lou Malnati's for some deep dish pizza or head to The Violet Hour for cra...
  • Fuck My Tight Ass and Make Me Squirt - JosephineFuck My Tight Ass and Make Me Squirt - Josephine I'm a naughty little slut from Chicago who loves to get down and dirty in the bedroom. I can't get enough of sucking cock, riding it like a pro, and taking it deep in my tight pussy. I'm always up for trying new positions and experimenting with kinky toys to spice things up. When it comes to mee...
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  • Lesbian horse lover wants to meet same in ChicagoLesbian horse lover wants to meet same in Chicago Lesbian Horse Lover in Chicago Hello girls! I am Sammi and I am nuts about my horses and about my woman! I have three horses and 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 that girl? Does that sound like...
  • Passionate Lesbian Seeking Orgasms, Oral Sex, and Ass PlayPassionate Lesbian Seeking Orgasms, Oral Sex, and Ass Play Hey ladies! I'm Della, a wild and adventurous lesbian from Chicago looking for some hot and steamy fun with another woman. I love exploring all kinds of sexual acts and fetishes with other lesbian and bisexual women who are just as eager to play as I am. From passionate kissing to mind-blowing orgas...
  • Attractive 48 yr old for younger man in Chicago, IllinoisAttractive 48 yr old for younger man in Chicago, Illinois Older Woman for Younger Man in Chicago Hi, my name is Brandy, age 48, fit and attractive. I am willing to travel for the right guy but I prefer within 50 miles of the Chicago area. I am blonde (Yes, natural!) and I am cute, with a small frame and long legs. I love music and dancing and sex! Hit me ...
  • Widower seeking female affection in ChicagoWidower seeking female affection in Chicago Chicago Widower Seeking Affection Hello there, my name is Jon and I'm seeking some female company for fun times and affectionate days. It has been a while and I have to face that I'm lonely. I am 52 and still look in my late thirties (I am told) and I am fit and healthy. I love riding horses, trav...
  • Always horny. Available for fetishes 24/7Always horny. Available for fetishes 24/7 Wet Pussy Lady in Chicago, Illinois I am hot, naughty and my pussy is wet! 😈 My independent sex services include wet pussy sex with kissing, blow jobs, 🍆 anal sex, 69 and all fetishes etc. I’m always hot and ready for sex so hmu. Message me: @WetPussyLady Send your pics for mine. ...