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February 24th, 2026

Tall, fit Butch... Butch for Femme in Chicago Butch for Femme in Chicago. I've been single too long and would love some intimate female company. Not sure about how this is supposed to go, so here I am just saying I am looking for a date. I am romantic and thoughtful and I will bring you your favorite flowers and take...

Let's Get Lost in the Windy City Together Hey there! I'm Adelle, a fun-loving gal from Chicago, Illinois. I may not be your typical girl next door, but I guarantee you won't be able to resist my charm. Whether we're grabbing deep dish pizza at Lou Malnati's or sipping on craft cocktails at The Aviary, I know we'll have a great time togeth...

FB Banned Me For These Pics. WTF!! Chicago M4M Male for Male in Chicago for Pic Swaps Hey guys, I'm Sebastian. I'm fairly new to the Chicago area. I'm interested in meeting a man for male companionship and fun. I am fit and love to show off my body. I apparently got in trouble with Facebook for posting my pics. Message me online for special acc...

Smokin' Hot and ready for a date! Hot Girl for Man in Chicago Ok, so maybe Smokin' hot is something you need to decide, but 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 ...

Shy 41 yr old guy in Chicago, Illinois Shy Romantic Guy 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. If you would like to swap photos and contact info just message me @ShyRomanticBryan and I will respond as soon as...

Let's Explore the Windy City Together Hey there, I'm Wesley from Chicago, Illinois. I'm a fun-loving guy who enjoys exploring all that this city has to offer. 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. I'm looking for some...

Ready for an Unforgettable Adventure? Hey there! I'm Kelsey, a fun-loving and adventurous gal from the beautiful city of Chicago, Illinois. Looking to meet someone special who can keep up with my zest for life? Well, look no further! I may not fit into society's cookie-cutter mold, but trust me, that's what makes me unique. My bubbly...

Widower 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...

Naughty Joane from Chicago Wants to Play I'm a wild one, ready to get down and dirty with you. I love getting fucked hard and deep in every position imaginable. Doggy style, reverse cowgirl, you name it - I'm game for it all. 💦🍑🍆 When it comes to kinks, I can be a bit of a freak. I enjoy being tied up, blindfolded, and teased...

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...

Explore My Sensual Side with Alyson Hey there! I'm Alyson, a fun-loving gal from Chicago who's looking to meet someone special. I may not be a supermodel, but I've got curves in all the right places. My friends would describe me as adventurous, spontaneous, and always up for trying new things. I love exploring the city and checking o...

Unleash 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...

Elegantly Seductive Chicago Gal Seeking Adventurous Date Hey there! I'm Ginnifer, a sassy Chicago gal looking for some excitement in the dating scene. I may not be your average girl-next-door, but that's what makes me stand out from the crowd. If you're into unique and intriguing individuals, then I'm your girl! 💋 I love exploring new places around ...

Fuck Me Hard and Make Me Squirt All Over Your Cock I'm a naughty girl from Chicago who loves to get down and dirty in the bedroom. My name is Selle, and I'm always looking for someone to satisfy my insatiable sexual appetite. Whether you want to give me a sloppy blowjob or make me scream with pleasure as you pound my tight pussy, I'm game for anyt...

Looking 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...

34 yr old Lonely businesswoman seeking female in Chicago Successful Business Woman for Female in Chicago I am Julia, 34 and a successful business owner but I work too hard. I have a flexible schedule so I've decided it is time to begin dating again after a long time being single and focused on work. I have my own money so I don't need anything but your t...

Still unpacking but looking for a date in Chicago New Girl in Chicago My name is Charlene and I literally just move here last week. I have barely unpacked yet and I am so wanting to get out and meet people! I love the movies and popcorn and music and dancing and having fun! Go ahead and hit me up for a date, or a drink or something! Message m...

Ill make you want to leave your girlfriend 😂😋💋💕😜😏💦💦 Hi baby if you're looking for a night to remember, then a sexy man like you should not have to wait any longer‼️... Im really craving you and I promise I won't dissapoint you! I know EXACTLY what you need‼️ but believe me, I can show you better than I can tell you!Wanna find out? i don...

Baby Face Hot Dude waiting for the ladies Male Escort in Chicago I am Howie and I am waiting for you. I am 37, hung and it. I focus entirely on your pleasure and will do what you want. Your satisfaction is my top priority and guaranteed! Message or call @BabyFaceHowie...

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. Not all the time, but you need a good sense of humor. Life is too fun to be serious all the time. Message me ...

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 ...

No Strings - Hot and Sultry, Looking for Affection in Chicago No Strings Hookup in Chicago 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...

Passionate Lesbian Seeking Orgasms, Oral Sex, and Tight Ass Play Are you a woman who loves to explore your wildest desires with another woman? I'm Selina from Chicago, Illinois, and I'm looking for a local lesbian, bisexual or bi-curious woman for some great sex and fun. Let's get down and dirty together! 😈 I love everything from passionate kisses to intens...

Eager to Meet You in Chicago! Hey there! I'm Alexia, a fun-loving gal from Chicago looking to meet someone special. I may not be your typical girl-next-door, but I promise you won't be disappointed. Let's grab a coffee at the trendy Intelligentsia Coffee or enjoy a romantic dinner at the iconic Girl & the Goat. If you're feeling...

Passionate 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 Orgasms, Oral Sex, and Ass Play I'm Vicki, a hot lesbian from Chicago looking for some steamy fun with other lesbian and bisexual women. I love exploring all kinds of sexual acts and fetishes, from oral sex to ass play. I want someone who isn't afraid to get down and dirty with me in the bedroom. If you're into passionate encou...

Hot and Ready for a Chicago Adventure!
Hey there, fellow Chicagoans! My name is Gere, and I'm on the lookout for someone special to share some incredible moments with. 🌈 If you're wondering what I look like, picture this: I've got a unique body type that's perfect for cuddling up on the couch during a cozy movie night or exploring ...

34 years old Man seeking Woman in Chicago Man seeking Woman in Chicago, Illinois Hi there ladies, I'm Brandon, age 34, 6' tall, 220 lbs,. I am excited to meet a sexy woman who would like to explore greater depths of passion. If you would like to say hi, come and see my profile @Brandon34M and message me for pics and contact info.  xo...

Let's Fuck, Suck, and Play All Night Long! I'm Rick from Chicago, Illinois, and I'm looking for a local woman who's ready for some wild and raunchy fun. I can be found on FreeSexAds.com under the username rickchic15185. I love everything from passionate lovemaking to kinky role play. I enjoy giving and receiving blowjobs, exploring differ...

Looking for a Connection in the Windy City!
Hey there! My name is Renaud, and I'm on the hunt for someone special here in Chicago, Illinois. 🌆 I may not have the body of a Greek god, but trust me, I've got a personality that will make you swoon! 💪🏼 And let's be real, who needs six-pack abs when you can have six-pack laughter? 😄...

Italian/American Gigolo to make you feel good Italian Stud for Woman in Chicago Hi, I'm Alex, an Italian man, age 34, in Chicago. Italians really are the best lovers and we know what to do to please our ladies. I am an independent escort who can serenade you, cook you a beautiful meal in your own kitchen and spend the evening with you until yo...

Irresistible Yolande from Chicago Hey there, I'm Yolande from Chicago! Are you looking for a fun and adventurous date? Well, look no further because I'm here to sweep you off your feet. I may not be a supermodel, but my curves will definitely catch your eye. I have a mix of European and Latina roots that give me a fiery personalit...

Discover the Spark with Elizabet from Chicago! Hey there! It's Elizabet, and I'm on the lookout for someone special to share some amazing moments with. So, let me tell you a little bit about myself and what makes me unique. I'm a fun-loving lady who enjoys exploring all that Chicago has to offer. Whether it's strolling through Millennium Park...

💋 Sexy Spinner Ready To Play Sexy Spinner Amanda I am Amanda, age 32, brunette, fit with a model's tight body and a nice booty if I do say so myself! I aim to please and promise that you'll leave satisfied and wanting to come back for more.  Ask for BrunetteAmanda69 Social media verification is available. Send your photo...

24 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...

W4W - Artistic Soul Looking for a museum-hopping companion W4W Art Lover in Omaha Username: @ArtisticSoulAge: 25Gender: FemaleSeeking: FemalePhotos: 29Videos: 2Text: Yes I'm a 25 year old woman living near downtown Omaha. I enjoy visiting the Joslyn Art Museum and wandering through the galleries at the Bemis Center for Contemporary Arts. If you're an art ...

I'm Alexis & I'm Everything Ur Looking 4! Alexis in Chicago: Everything You're Looking For! Hi..... I'm Alexis, a new but independent and experienced escort/provider in Chicago! I'm Looking to meet some new people and hopefully repeat clients. I am a laid back and open-minded professional lady, but I have a wild side. I will leave you smi...

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!   xoxo SylviaM24Chicago...

Hot and Horny Guy Seeking Local Woman for Wild Fun Are you a naughty girl who loves to get down and dirty in the bedroom? Do you enjoy exploring your wildest fantasies with a man who knows how to please you in every way possible? Well, look no further because I am here to fulfill all your desires and more. My name is Garwin, and I am a man seeking...

Eager to Meet You Hey there! I'm Meggan from Chicago, Illinois. I may not know you yet, but I'm excited to change that 😉. I'm a fun-loving gal who enjoys trying new things and exploring the city. Whether it's grabbing a slice of deep-dish pizza at Lou Malnati's or taking a stroll along the Riverwalk, I'm always ...

Erotic Adventures Await with Lianne79578 Hey there! I'm Lianne from Chicago, Illinois. I have long brown hair, piercing blue eyes, and a smile that can light up a room. What I love most about being lesbian is the deep connection and understanding that comes with dating another woman. I'm looking to meet a lovely lady for some fun and ex...

Brandon 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...

Lesbian Fitness Freak with Sporty Body in Chicago Lesbian Fitness Freak in Chicago Hi ladies! This is your girl Teri! I love to work out. I run, I lift weights and I am fit and tanned. My height is 5'8" and I have brown eyes and blonde hair. I want a woman who is her own person and financially responsible.  If you are a fun type who loves fi...

Male for Male: I can please you here or at your home. [Male for Male] Bradley M4M Escort in Chicago Area Hey guys, M4M escort in the Chicago area. I am Bradley, 31, fit, European by birth and waiting for you to call me so I can show you a great time. 5' 10" and 8 inches. View my online profile and message me BradleyKM4M. Send your photo for mine.  No hard ...

Baby faced 22 year old male in Chicago Male for Male in Chicago, Illinois Hey there! I'm new to Chicago and looking to meet somebody fun. I am funny and intelligent and well versed in pleasing a man. I'm fun and love to have a good time. If you like to talk I like to listen. I enjoy good conversation, dining out and fine wine. I give go...

Passionate Lesbian Seeks Orgasmic Encounters I never thought I'd be the type to post an ad like this, but here I am, looking for a sexy lady to have some wild fun with. My name is Myranda and I'm on the hunt for a local lesbian, bisexual or bi-curious woman who's down for some hot and steamy action. I love exploring all kinds of sexual acts ...

Elegantly Erotic Glory from Chicago Hey there, I'm Glory, a sultry lady from the Windy City looking for someone to sweep me off my feet. I may not be your typical girl next door, but I guarantee you won't be able to resist my charm and wit. Let's meet up at Millennium Park for a romantic stroll or grab some deep-dish pizza at Lou Ma...

Get Lost in the Windy City with Me Hey there, I'm Karel from Chicago! I may not be your typical girl-next-door, but I guarantee you won't be able to resist my charm. Whether we're grabbing deep dish pizza at Lou Malnati's, catching a show at The Second City, or taking a stroll along the Lakefront Trail, I promise we'll have a great...

Looking for a Wild Woman to Fulfill My Wildest Fantasies Are you a kinky girl who loves to get down and dirty in the bedroom? Do you enjoy exploring new sexual experiences and pushing your boundaries? Well, look no further because I'm Kirk, a man seeking a local woman for great sex, adventure, and fun. You can find me on FreeSexAds.com under the usernam...

Looking 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...