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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February 6th, 2025

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...

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 ...

Don't ever play leap frog with unicorns! Hi I'm Claire, a cougar here in Chicago to show young men that with age comes wisdom like in the headline above. lol I am willing to share my acquired knowledge with eager cubs who want to be shown a better way. Of course most of the knowledge I have would be sexual in nature since that is why I'm h...

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...

Italian Couple Wants Single Man For Threesome in Chicago Couple Seeks Male Companion in Chicago Buonjourno we are Mario and Gabriella new here in Chicago. Not only are we Italian, but we are from Italy. From a small town of Livorno near to Pisa. We are in the swinger lifestyle and lately have need of a man to join in with us for some adult fun. Our engli...

I usually root for villains... BadBetty big boobs here in Chicago with a sailors mouth and a dirty mind to match. I'm a lesbian female 32 years old, mixed races, 38D cup, big nipples, brown hair and eyes, 5'7, 150 pounds, little salty and horny AF. I want you to swab the deck tonight and then do it again till everything is ship-s...

BBW's - Heavy Hotties With Huge Sexual Appetites!... BBW's for Men in Chicago There are thousands of local chubby cherubs looking for men just like you in the Chicago area. They want fun, romance and want to meet you. Come check out their naughty pics and profiles. Click Here for More!       Other Sites of Interest: BBW's -...

Bosnian Beauty looking for American chick Bosnian Beauty Looking for Woman in Chicago Hello. I am Lulu and I am 27 years of age. I speak fluent English and I now live in Chicago. I am able to travel within a reasonable distance meet the woman of my dreams. Please send me a message @LuluLynn27 to swap photos and chat....

New Body New Me M2F post-op in Chicago Hi, I'm Natasha, newly transitioned and ready to date. Gorgeous red head with slender legs and curvy body. Want to come and join me for a drink? I love sex in my new gender!!! Seeking a local area man who will enjoy sex and passion with me. Message me online Natasha...

Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Chicago who doesn't smoke, but has a thing for sexy men smoking cigarettes. Call it a fetish or a kink if you will, but I love it. If done right it is soo sexy and inviting to my senses and gets my motor running every time. Truth is that it's erotic all in it's...

HEY BOY - Tap into THIS Phat Booty! I ain't playin, I need a man to plunge into my juicy juice and give it to me hard! I got a phat booty and cannot lie cause we need a real man, and only a real man will do. I'm Natalie, 5'6, mixed race, 36D cup, 42 hips and a phat ass baby! If you live in Chicago and need a booty call like I do then ...

Amazonian Warrior princess looking for her Xena Tall Woman for Woman in Chicago I enjoy cosplay and RPG. You wanna role play with me? My name is Terri and I am 5' 11", 160lbs and have long dark hair. I am fit and lightly muscular but not ripped. Just toned. Wanna meet me just message me @AmazonianFem4X Send your recent photos for mine. No guys...

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....

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Come 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...

💯REAL💯HANDSOME💯MANLY Gay MANLY - SEX You like cock?? 🍆  You ready for some manly gay sex here in Chicago? I know I am, I made this ad to make a nice BF to fuck or fuck me.. We can even find some other sexy guys to have some sex with too.. I love partying✨ and having group sex. Do you like to take it or g...

Love Giving Head!!! Hey all you hot men in Chicago! I'm OralAimie the best at giving mind-blowing head because I love it so much. But then who doesn't love it right? (if we're being honest) Lots of girls say they don't love it, but they are liars! There is nothing like it and every one is different. Long ones, fat...

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...

Trans Flight Attendant Seeks Man for NSA... Hi I'm Annie, a 32 yr old t-girl, a Chicago trans flight attendant looking for someone who can understand my wild lifestyle and sometimes erratic hours. I work hard and I play hard. Let's wing it tonight baby! I love men, passion and exploring new things sexually. To say that I'm fetish friendly wou...

Latina Beauty needs love in Chicago Hola señoras. Soy Juanita y soy local en esta zona. Tengo un trabajo y tengo mi propio auto. Puedo viajar para conocerte si quieres conocerte a mitad de camino. enviarme un mensaje @Juanita4love. Yo soy 5'4" y tengo 29 y alrededor de 140 libras.   Hello ladies. I am Juanita and I ...

Hungry for Explosive Sex, Food, Fun and Adventure!... Im curious, smart, free, and funny. I like to travel, eat good food, watch movies and spend intimate time with my man. With you I will be my best self and grow as a person. If you are fun, adventurous, Sexy and happy go lucky then contact me by clicking here. I'm TessyM and you won't be disappointed...

Trans Playmate Sex Kitten... Ebony trans woman in Chicago wants to be your sex kitten and playmate so let's make a playdate! I love all men so any race or body type or political side is fine with me. I can get along with anyone and we're gonna have a great time. I do all men, gay, bisexual, bicurious, swingers and groups. I am ...

Super sexy busty woman looking for love and appreciation Super Sexy, Busty Woman in Chicago Hello. My name is Lyla. I am new to this area and originally from New Zealand. Would like to date genuine, honorable and funny man. I love sexy and being sexy and being admired by a gentleman. View my profile pics BustyLylaX...

24 y/o Bartender Wants No Strings Fling 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 you think you are a good fit.&n...

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 with no kids and I own my home. I am local to this area and have lived here for 22 years. I want to meet a kind a funny lady for fun times. Come and say h...

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...

SECRET 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...

I Need a Massage... I'm a Sucker For a Good Massage!... Hey any of you fellas in Chicagoland know how to give a girl a body rub? I need a slow long lasting massage by some stong sexy masculine hands. No quickies either! If things work out maybe we could have a mutual more long term thing? You know, a more steady get together? You scratch my back and rel...

Crystal, 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 masseur, hot body and hung. If you want to get together, Send me a private message Crystal27trans <3 ...

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 ...

🌹 Seeking My Juliet 🌹Chicago Hey there, lovely ladies of Chicago! My name is Romeo and I'm on the hunt for my very own Juliet. Are you ready to be swept off your feet by a modern-day romantic? Look no further because I'm right here waiting for you. Swap pics & contact info ChicagoI may not have a balcony to profess my ...

Gay Lawyer seeks Male Soul Mate Hello, I am a 38 year old lawyer in Chicago looking for a handsome and intelligent man to share weekend fun and outings with. I am reasonably handsome, but that is all about perspective. I am 6'2'' and have short brown hair. I like to dress nicely. I enjoy coffee, great conversations, travel, sports...

Here For The Hot Chicago Girls, No Games, Just Fun! Chicago Lesbian for FWB I'm Kelsey a tatted lesbian female 33 years old, living in Chicago seeking a woman for some FWB fun and no games. They say I have a bit of a hard edge on me, but I am kind until I'm not. Just like anyone I don't like to be pushed and abused, so what more can I say about that...

INSTA ACCOUNT LOCKED 30 DAYS for TOS violations. Wanna Swap Pics Insta Account Locked for TOS Violations I guess they don't like nude pics anymore or maybe my pics are just too hot for Instagram. Don't worry, the show and free pictures are still going on. What's wrong with nudity and sex anyway All I want is to hear whether you like what I post or not. It helps ...

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Busty chocolate Beauty loves milk chocolate treats Busty Chocolate Bunny in Chicago Hey gals, I am Dolores and I am a dark cholocate in complexion and big busted. I am a foodie and I love all foods! I watch all kinds of food shows from all over the world! Hit me up @BustyBunnyXXX Hope to speak to a food/dining loving lady soon! ...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Chicago I will help you unwind and create a cozy environment for you! I am 36DD, 7" and can give you so much pleasure. View my Transgender World profile and message me for my pics! @GayleTGirl Gayle <3    Transgender World Profile Username: GayleTGi...

Tantalizing Tina with a HUGE W33NAH! Chicago Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Chicago men and wnat to show you a time you'll never forget! Do you like them thick, long and uncut? Then I'm the girl for you. Look no further for a passible and functional t girl - HERE I AM!  About me: 2...

Submissive and Need a Dominant Sir in Chicago Our Little Kinky Secret in Chicago Allow me to introduce myself, I am Chelsea here in Chicago looking for a Master to give me what a real woman needs. I am into domination, humiliation, bondage, roleplay, gags, whips, toys and am still exploring my fetishes. I'm a professional woman working in the ...

No Beer Goggles Required! Renee 4 NSA in Chicago Hi guys I'm Renee from here in Chicago looking for a no strings situation. Don't go out to the bars looking for a hookup when you can actually see what you're getting when you come visit my profile page. Those bars are so dark and with a few drinks we tend to make bad ch...

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 BREAK TWINKS and turn them into MY SEX PUPPETS! Big top bone thug gonna wreck you and make you twinks tap out! Looking for sissie boi to use and abuse here in the Chicago area. All is fair and shit as they say. Needless to say I'm the dominant and controlling type in any situation. Your gonna get the big one rough and deep honey! No screamers ple...

Sailing nut wants to meet lady sailor Male for Female Date Wanted in Chicago Do you like going out on boats and sailing into the sunset? If you do, give me a call and we can check out my boat together. My name is Lewis and I love the water. Contact Me @CaptainLewis....

Beautiful Krystale 25 Chicago visiting now Beautiful Shemale Visiting Chicago Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me.  Krystale25shemale Age: 25 Location: Chicago Sex: Shemale Seeking: Man ...

Asian Twink for Big Hairy Bears... Bottom Asian Twink wants to have hot encounter with big hairy bear tonight! I am new to Chicago and work in marketing for a large real estate firm. I don't get out much and would like to meet the man of my dreams and have wild sexy nights. I'm 24 years old, Asian gay male, hairless, tight ass, lots ...

I want to worship your sexy sweet feet... I'm a passionate Italian man looking for sexy feet to pamper in Chicago. Just the sight of a pair of angel feet leaves me breathless. I can't even go near a beach for the over-stimulation it brings. I do like it in the spring when women start wearing strapped sandals though because it usually leaves...

Need a Dirty Sexting Buddy in Chicago... Hi guys I'm Cathy in Chicago and My fantasy is to sext NSFW naughty pics and short videos to a kinky man while I'm at work. Upblouse when I'm braless, upskirt w/o panties, toy play etc. I get really horny in my office and need you to send dirty comments back. After a while you send me nasty pics of ...

Naughty but nice girl next door Naughty Girl Next Door I want you! At least I want someone like you...I want love, and friendship and fun dates and mystery drives. Please don't be shy. Come and say hello! Send me a message @NaughtyGirlTrish69  I'm a naughty girl of many interests. Internet junkie, social mediaholic, pa...

Hot Italian Sugar Baby Wants to Live Her Best Life Now! Hello distinguished gentlemen of Chicago! I'm Alexis, full blooded Italian, 21 years old, 5'6, large boobs, 140 pounds a native of Aurora originally, but moved in to the city when I turned 18. I love the finer things in life and more mature men, so this works out for the both of us really. If you ar...

Looking for the world's best playmate! Need: One good looking guy who can make me laugh Also: has to like music and movies and be a gamer, not a player. What you get: Me! My name is Patrice and I am 25, 5'6", curvy with dark hair with a blue streak straight down the back of my head, which I love! I am also a pretty good cook, so if we ...