Chicago, Illinois Sex Ads and Adult Classifieds

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June 23rd, 2025

Looking for some action. need a plumber late nights 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'm a Steamroller Baby! Hi ladies, James here nice to meet you! Let's hop on my bike, put our knees to the breeze and do whatever the hell we please! I'm good with my hands, still a bit of an outlaw at heart, 35 years old, lived here most of my life, blonde hair, blue eyes, 6'1, around 220 pounds, muscular, love women, hug...

Divorced College Lecturer Looking for Excitement! College professor and divorcee, age 42, looking for someone loving, intelligent and fun. I live in the Chicago area and I am happy to meet at a neutral place or entertain at my place. I own my own home and I am not expecting you to pay for everything. Looking for someone who loves history and books,...

Great kisser, looking for same Did I get your attention? If you are reading this, I must have! So, there is more to me that just great kissing, but I wanted a hook! Here goes...I am 32, a manager in a store and I just relocated to Chicago because of my job. I don't really know many people yet, except my roommates and I am kind of...

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...

BIG n CUTE BBW for Male in Chicago 🍑🔥 Brianna BBW for Chicago Male Cute, flirty and playful BBW seeking a nice man in the Chicago area. 🍑 I'm curvy in all the right places. I like to dress nice and I'm classy in public. But I love getting down and dirty in the bedroom! I'm a hot, naughty girl who wants it all. I love exploring sexua...

🔥Gay Hookups – Bedroom Eyes & No Bullsh*t Vibes 💋🍆  Your mama warned you about me yet your dad would secretly appreciate my nature 😈 34,  toned, tattooed, and nasty in the best way possible. I seek a genuine male partner who  understands my body type through strong hand usage and dominant presence and filthy sexual thoughts. Your ...

Alex's Huge Throbbing Cock in Chicago 💦💦 New to the scene, willing to try anything! Thanks for checking my ad. I'm new to this. My name is Alex (hmu @AlexThrobbingCock4u) and I love fucking and getting my huge throbbing cock stroked and sucked to completion. I'm single but not totally out yet so please be discreet. At the same time, I'm a...

Latina chick looking for the love of my life. Isabel Para Mujero Por favor, dime que estás ahí fuera. Me llamo Isabel y soy una lesbiana solitaria que busca su amor. Ven a buscarme. Sabes que te estoy esperando. Hablo bien inglés, pero necesito mejorar un poco más. Ayúdame a que te ayude. Envíame un mensaje a IsabelParaMu...

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 ...

Are You Uber Horny? I AM - Maybe We Can Work This Whole Thing Out Together!... Nympho Seeking NSA in Chicago I am Tory, a 24 year old, brunette living in the Chicago area, 5'5, medium build, told that I'm fun, easy to be around, a good conversationalist and have a sexy relaxed vibe. Do you live here locally, find me attractive and love big playful titties? Then I might b...

Caught My Boyfriend Cheating... Now it's MY TURN! Looking for some hot NSA revenge sex with the right guy in Chicago. Must be STD free and have your own place or arrange for a room. I will not give you my real name or address here. I'm a 24 year old, 5'7, slender, blonde haired, blue eyed female seeking a sexy man. We'll have to chat first and meet...

Free Illinois Transexuals Guide Illinois Transexuals Guide The Illinois Transexuals Guide was prepared by our trans experts at AmericanTransexuals.com. We bring trans women and admirers together for friendship, dating and sex hookups. View our free Illinois Transexuals Guide online.  Where to Meet Transexuals in Illi...

Any Irishmen Here in Chicago? Well, step right up then gentlemen I'm from Ireland and live here in Chicago for two years now. I am awaiting my naturalization papers to go through so I can become a US citizen. Currently I work in catering mostly for weddings. It's a good enough job, but I'm not here to tell you all about my life ...

Love to Make Love! Grab hold of my big titties baby, spank me, and just do me already! I am here in Chicago scoping out this site looking to meet new people and have some NSA fun. Some of my interests include music, sports, and fashion. If you are interested and want to talk don't be afraid to approach me. Click ...

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...

I 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...

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...

Nature Boy Seeks Hot Natural Man... I am Ira and love being out in nature when weather permits. I'm looking for a natural gay man (such as a bear or thug) who by his nature will take me and have his way without restraint. I'm a gay twink 22 years old and love to be ravished by force by a strong man. If you live in Chicago and fit this...

Holy Capped Crusaders! - We'd Make a Hot Dynamic Duo! Bottom Boy Wonder searching for his BAT-man. Twink 24 years old, 5'9, 160 pounds in Chicago seeks cosplay leading man to form a dynamic duo. We may not exactly fight crime, but we will have lots of sexy roleplay fun. Let's travel and go to conventions and events and contests! We'll take the world by...

Find Big Love With This Well Endowed Lesbian BBW in Chicago!... Hey girls I'm Boobylicious a Chicago born BBW lesbian with the most. I need my huge titties ravished and admired by a woman who appreciates them. Bite them, slap them, squeeze them suck them and tie them up if you must. Then spank my phat ass and bring me over and over again with your tongue. As you...

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...

Mature Latvian lady seeking mature fun gentleman 🐈🐈 Mature Latvian Lady in Chicago Hello there. I am Rada and I am a sexy mature woman from Latvia, now in Chicago. I am very independent and charming and looking for a guy I can talk with and laugh with and just hang out with on weekends. Please contact me online or text....

Ebony W4W - 🌙 Movie Night or Makeout Session? You Decide 😘 📍 Chicago Ebony Lesbian Seeks her Queen, or Princess 👸😉 A soft playful cutie like me is looking for a girl to play with tonight. Netflix and  chill? More like kiss and thrill👄 .  I can meet up with you to watch a late night  movie, buy some extra snacks and maybe sneak som...

Looking for the bride of my dreams Chicago Contractor Seeks Wife This is Erik and I am a local resident and own a contracting business. I love distressed property rehab and I'm always looking for rehab projects. I am looking for a bright intelligent woman who can make me smile. When not working, I love the outdoors and I am an avid ...

I Need a Sexy Man to Tame Wild Willy! Hung Chicago Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Chicago with a big wild willy that always seems act out in inappropriate ways at the worst times. For instance I'll be relaxed, minding my own business at my favorite Starbucks and see a ...

💎 Adorable Sugar Baby 💎 Seeking his Generous King 👑 📍  Location: Chicago    Seeking: A kind/dominant daddy👑  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...

🔥🔥🔥 WANT TO JOIN US IN SOME SWINGING SEX??? 🔥🔥🔥 Hey there, I'm Heidi from the beautiful Chicago. My husband and I are a fun-loving swinging couple who love exploring our fantasies with like-minded individuals. Swap Pics & Contact Info There's something so exhilarating about the swing lifestyle - the thrill of meeting new people, the exci...

Worship My Ebony Feet🦶🏿 Sexy Ebony/Black Woman With Soft, Sexy Feet For You To Kiss Chicago Ebony Date Hey gentlemen,I'm Queen Lisa 👋🏾💋 I'm sexy, I have a nice thick ass 🍑 for you to grab on to. I want us to play and have some sexy fun. I want you to bow down to me and k...

Chill Dude Needs His BBW Queen... Hi ladies I'm Mike from here in Chicago, age 30, 6'0, 190 pounds, Italian, French, Norwegian mix, tatted, well endowed, muscular, journeyman plumber, who loves lots of curves and passion in his woman. I don't meet many women in my line of work and bar pickups are not usually the right way to find a ...

Fitness Freak has sporty body Hi, this is Teri! I love to work out. I run, I lift weights and I am fit. I am medium height and weight, toned and tan. 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 an athletic female partner, take a look at my o...

Looking for Older Gentleman 🍭 Chicago Area Seeking Chicago Sugar Daddy Exclusive Arrangement I am 24 and looking for mature. I have a good sense of fun and a smooth, hot body. My long hair is chocolate brown and my skin is very soft! I want to meet a cool guy who likes to have fun. Send me a private message for my pics and contact...

I'LL DO ANYTHING YOU WANT ME TO...😈😈😈 Hey babe, I'm Julie and I'm new here. I need a fun man to have some naughty fun with. I love to 🎉 PARTY 🎉.. maybe drink and more 😉 Then while we're having fun partying, we should fuck and fantasize. I love dressing up 👗💄 I love pretending to be whatever you want me to be. I want us to...

ShopinRound38 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 ...

Intense, vibrant and dark haired beauty, WLTM handsome fun guy Intense Dark Haired Beauty in Chicago Hey, I'm Janey and I'm still looking. I'm kind of bored and need new friends and maybe some romance. I have dark hair, soft skin, sultry eyes and a great smile to make you happy. How about you? Why not call and let's see where things go? Message me now #J...

Earth Momma - Strict Vagitarian... Hi I'm Orla, 29 years old, sort of a new age type lesbian in Chicago looking for a compatible woman who I can share nature's bounty and goodness with. If I start boring you with my star charts, crystals, palm reading or alien theories just shove something yummy and lickable in my mouth. That always ...

💪🍆 I'm All Tha Chocolate You Could Need 💪🍆 Hey I'm new to dating sites but I'm ready to give it a try and see who might message me. I'm wanting to get out and have some fun. Yes I'm black and yes I have a thick 🍆 but I'm so much more than that. Also I want you to know that I love all shapes and sizes of men, I just want someone I can conn...

Fabulous Filipina woman wants wonderful man Filipina Woman Seeking Passionate Man Hey guys, my name is Amina and I am full Filipina, just moved here to Chicago. I want to meet a kind and passionate man so please only message me if you are serious and fun and want pleasure! I am open minded. Hit me up @Amina4Passion to chat online and ar...

Bring a toy for Kitty (w/batteries) on our first date!... I'm a bit of a goth and have recently discovered the magic of toys. Bring your favorite toy on our first date and I'll bring mine. This could be our Toy Story. Lesbian in Chicago seeks female companion for erotic encounters and possibly long term relationship. I'm Katzzy and am 33 years old, 5'7, 15...

Widower seeking affection in Chicago Chicago Widower Seeking Affection Hello ladies, my name is Jonathan and I am 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...

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...

Oil Me Up and Rub Me Down Baby! Desperate - Need Massage in Chicago! Cindy here in the Chicago area waiting anxiously for your next shippment of oil to arrive so I can come over for a body rub. Hope you ordered enough to get us through the night! Well, that's ok cause I ordered some of my own for insurance. lol I have a few probl...

Italian single girl looking for love Ciao amore mio! Sono nel mercato per trovare un bell'uomo muscoloso e carino. Se sei carino e in forma mandami un testo per una data! (AngelicaXOXO) Hello, my love! I am in the market for finding a handsome man who is muscular and cute. If you are cute and fit send me a text for a date! (Angel...

Older woman seeking mature gentleman for long term relationship Older Woman Seeks Mature Man Seeking gentle fun, soft cuddles and long walks in the park. I am a romantic at heart and love a good laugh. Prefer relationship. Go ahead, don't be shy, message me or call @OlderSexySuzie. We can enjoy life together! ...

RATE MY PICS XXX Let's Swap Pics and Sext Online! Let's Swap X-Rated Pics Online I wanna play a game. Here it is: I really just wanna send you my dirty pics. I love it when men get off to me and all I want in return is a rate of my pics and how good your orgasm is. Wanna play Look me up: RateMyPicsX  It's free and I do reply to fre...

I'm Sexy And I'm Nona!... Hello girls I'm Nona a tatted, 24 year old, brunette, 5'8, 150 pound lesbian originally from right here in Chicago. What makes me sexy you might ask? Because - I'm NONA! - and you'll get the rest of the answer later when I show you. So, talk dirty to me and send me naughty private pics. If it makes ...

Ken, 42, lonely for you Male for Female Chicago Hi there! My name is Ken and I am 42 and looking for a real nice woman in the Chicago area. Send me a message and check my profile @Ken42seeksWoman for my recent pictures and contact info. Let me know about you. I enjoy skiing, hiking, boating, travel, gaming and reading. Ac...

Sexy Sissy Twink Wants to Get Rekt by Power Top Man! Drive it home rough and real hard big boy! I'm Harris a 22 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 Chicago, are ...

Hey 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 ...

Open Minded Woman seeking Open Minded Man When I say open minded, I mean in every aspect. I like a mass debate ;-) and I enjoy a good intelligent conversation. I like uninhibited romance and sex!! I am looking for same in a partner. If you enjoy giving great sex just as much as you enjoy receiving, we might be a great match!  Let's sw...