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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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December 1st, 2025
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,...
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...
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...
Spicy and Hot T-Girl from Colombia Latina T-Girl in Chicago Hey guys, I am Colleen and I am looking for a long term relationship. I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery. Nice surpise waiting for you! Send me a private message! ColleenLatinaT...
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 ...
Nervous and new to this! It's my first time posting an ad of this sort. Not even sure what you want to know. I can start with my name, which is Rose. I love to travel and have been all over the place! I have a wall in my home which is dedicated to all the postcards I have sent myself from all the places I have been to. Una...
Jaw Dropping Hot Lesbian Desires to meet her Princess in Shining armor I am tall and light chocolate. I am elegant and slender with short afro hair. I look like a Bond Villain but I am truly very sweet.  Why not give me a chance? I am also fun. Message me @MilkChocolateFemme if you like a taste of hot chocolate! MilkChocolateFem in Chicago Username: @MilkChocola...
Fun Loving Couple in Chicago Seeks Female for Threesomes... Swingers in Chicago Seeks Female Hi, we are Jordan and Riley, a sort of a younger swinger couple in Chicago looking to explore threesomes with the right girl who is open to sex with a man and a woman at the same time. We look forward to experimenting with some wild fantasies we have and welcome any...
Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Chicago for Man Hello, thanks for looking at my ad! I'm Lara. I am 32 years old and transitioned when I was 24 but no surgery other than breast augmentation and some minor body touchups. I pass exceptionally well, fully functional. I'm feminine and classy so you will be pr...
BANNED ON FACEBOOK... Wanna see the pics that got me kicked out? BANNED ON FACEBOOK. WANNA SEE MY PICS? Hey there. I'm Kimberly, my profile is in Facebook jail for posting my hot pictures.  WTF?! So here I am. Want to see the pics that got me kicked out? Look me up: KimberlyX69 My pics and videos are free. No need to pay for anything. Just ...
Vibrant and Intense 26 year old wants to meet sexy dude Hi! My name is Angelina. My body is in great shape and I like to exercise and stay fit. I am fun-loving and down to earth. Would like to meet same in the perfect guy. I love swapping pictures and sext messages on mobile so don't be shy. I think swapping pics is the perfect way to set the tone for a ...
Stop Buffin Your Muffin Without ME! Latina lesbian 28 years old, 5'7, 140 pounds, 38C, tatted, pierced and always ready for some hot action in Chicago. I don't want to miss out on anything so let me flick the bean for you for twice the fun! I'm good with my hands and tongue ladies. I'm Lena and I'm just here for the sexy gurls, I cann...
Bite Me Butches! Chicago Lesbian for Butches Deena here in Chicago daring all you bad butches to come get me! I'm fiesty and kitty has claws. You aint gonna get this easy like you think. Yeah sure, I'm a little sarcastic, brutally honest and sexually hostile, but that sort of foreplay leads to explosive sex and you...
Hot stuff hoping for her sugar daddy Hot Stuff for Sugar Daddy in Chicago Hello gentlemen, I'm Kayte. I’m sexy, flirtatious, sweet & fun loving with a very wild edge. I am 5'4" with silky black hair. I am your ultimate hot girl next door, but with a very down to earth vibe. Let me spoil and mesmerize you!  Exclusive su...
VirginAss88, Never Been With a Man... I like having fun. I'm very honest perosn, very brave and interilligent. Love it here in Chicago and all the possibilities it offers for a guy like me. don't like the idea of bar pickups and would rather ease into this thing. Must be descreet and honest. Message me here. VirginAss88...
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 ...
Slovak woman lonely and looking for guy in Chicago Dark, sultry and tall, very well built, Slovak woman is here to please and be pleased. I desire for long term friendship, fun and love. My English is getting better so send photos and message me here @TmavoZmyselná Tmavá, zmyselná a vysoká Slovenka   Tmav&eac...
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, plz. Not all the time, but you need a good sense of humor. Life is too fun to be serious all the time. Message me ...
Mixed Race Male Seeks Sexy couple in Chicago... Hi there I'm James new to Chicago and I want to meet you. I've been divorced for about a year now. Not really wanting to dive in too deep just yet into anything serious, but you never know what will happen in the future. I need a sexy more mature couple from mid thirties to forties who can relate to...
Black man, 31 needs good boyfriend Black Daddy in Chicago area Man, I don't know what I am supposed to say here lol....I am Frank and I am 31, clean, fit and single. I am just recently out of a long term relationship with my ex boyfriend. I won't go into detail but we just drifted apart. Anyway, I'm ready to mingle! Locals only in t...
Looking for the real thing Sexy Hookup in Chicago I am told I am very sexy, but that is for you to decide. I am short, great body, confident and intelligent and would like to meet a Chicago guy for fun conversation and anything else that happens. I'm an internet junkie, love texting and sexting! I have a lot of pics and vide...
Anyone Here Interested in a Long Term Relationship? Hello, I'm Nora a lesbian living in Chicago my whole life. I'm 23 years old, 5'7, 130 pounds, athletic build, butch, dominant, love to party, loyal and don't really want hookups. Sex is important, but it's not my whole life. I want adventures and experiences and memories with the right woman of my c...
Latina Therapist to help you Latina Sex Therapist in Chicago Rest and relax under my gentle hands and feel the tensions leave your body. Latina woman, a caring sex therapist, seeking genuine adult conversation and romance.  Text or message me online! TherapybyMaria   Sexy Therapy by Maria Send your photos ...
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 ...
Amazonian Warrior princess looking for her Xena Tall Woman for Woman in Chicago I'm a soft butch bisexual/pansexual woman. I enjoy cosplay and RPG. You wanna role play with me? My name is Terri and I am 5' 11", medium/athletic build and I have long dark hair. I am fit and muscular from working out regularly. I'm interested in all types of women ...
Lesbian 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. 😉 Send me a private messa...
Chicago Wild Child Looking for a Thrill or Two... Let's Go Wild Baby! Hey boys looking for a party? I'm Jenna ready for life in the fast lane here in the Chicago area. About me - 21 years, 5'5, C cup, smoke, love to hang with the boys. If you are looking for a girly-girl then I'm NOT 4 U! Let's just take things as they come and don't get too hung ...
Chubby Chick looking for guy who can handle me! So, I am a little heavy but more 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 text me your favorite joke and we can see how we get along!  Lisa44DDChicago...
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...
Ranch owner and lonely ol' guy Male Ranch Owner Seeking Woman in Chicago Ok, I ain't that old. Just turned 48. I am a ranch owner with 40 acres and am looking for a gal who is adventurous, outdoorsy, fit and healthy enough for horseback riding, hiking, biking and picnicking on the trails. Enjoy travel and new experiences? Me too...
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...
SciFi lovin' guy getting lonely in Chicago I love SciFi TV and movies. I am Will. I am 31, tall and muscular with light brown hair, grey eyes and tan skin. I work and I have a nice home and car. I never seem to have time to get out and mingle. I need a friend with benefits! Send me a private message to @WillSciFiFan if you want to swap ...
PeeWee's Looking for a BIG Adventure! Hi, I'm Herman, and me and my little friend are looking for some excitement in Chicago tonight. If you are up for an adventure we are too! We aren't too picky, just hope you like Tequila and dancing. Please be motherly and kind. Can you come out and play?. If so click here to come out and see u...
Smokin' Hot Lesbian in Chicago... I'm Kat, 27yrs old, 140 pounds, black hair, brown eyes, dirty minded, tatted, love to smoke and I don't care what they say about smoking here in Chicago or anywhere. If you are a single lesbian or bisexual OK with smoking or are a smoker yourself then maybe we should chat. I love sex and smoking, a ...
Inviting eyes and seductive thighs wanting to find loving guy in Chicago I advertised here in the past and thought I found my true love. Well, I guess not so here I am again.  I recently moved, so I am new in Chicago and have no local friends to hang out with. I would love to meet fun, down to earth guy to explore passion and hot sex. I just need to have some fun an...
Chicago Cougar Could be a Cubs Delight Tonight!... Cougar on the Prowl in Chicago Hi there you sexy cubs I'm Joan and I'm gonna spoil you tonight! My den or yours, let's get wild in the sheets till I've had my fill. If you are a cub between 18 and 30 and live in the Chicago area then I've got something for you. Maybe you thought school was ou...
I'm Danish... Eat ME! Been dating most of my life and nothing too serious, but now I'm ready to settle down with the right person. I'm looking for a woman who will complement me. Where I have weaknesses she will have strengths. She must be local in or near Chicago, because I did a long distance relationship once and...
6'2 Dark Chocolate in Chicago Hey! I'm Gary, age 27, tall, dark, chocolate, want to meet you. Super ready HIV Negative. Come and play in Chicago at Roscoe's Tavern or Dorothy.  Message me @ChocolateRush for my pictures and #...
Single Female Wants to Explore Fetishes... I'm Dani, a sexually adventurous woman who is looking for a fetish playmate in Chicago who is able and willing to go with me on this kinky journey. In past non-kinky relationships I have always played a more dominant role (for some reason) however I have changed my mind and I am keen to switch to mo...
Take Me to a Strip Club!.... Female for NSA in Chicago I'm Diana, and I want to go to a strip club with you here in Chicago. It's sort of a kinky fantasy I have going on right now. I have other dirty fantasies, but this is one of those I've never tried before. I'll even buy you a lap dance! I love to see a man get turned ...
DESPERATE SEEKING A REVENGE FUCK! 🥒🥯💦 Newly single Chicago 22 y/o female needs a good fuck 💦 Hey there, I'm Trish from Chicago. Let's get right down to it. My husband left me and I need to fuck to make me forget about his sorry ass. I'm tired of being neglected so I'm looking for a nice, attentive man to keep me warm tonight. I'm cl...
Married But Playing in Chicago Married Woman Playing in Chicago Hey guys. My name is Jessica @Jexxica27, age 27. I'm married but playing around. He don't care. He said so and he cheated on me first so here I am. I just want to have a good time, no strings attached. Can you give me what I haven't had in a long time? I like i...
Any Sexy Couples in Chicago Want to Hookup? - Asking for a Friend 😄 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. ...
Hot and horny 4 Threesome in Chicago... Woman For Swinger FWB Hi boys I'm Sarah here in Chicago seeking the right couple for a threesome. It feels like I'm wasting away and not getting MY share. I'm looking for a sexy older couple with experience to show me true passion and skill. Someone who will teach me and attend to all my primal sex...
Lets Go Playah! Chicago Boys Come Out and Play! Mindy here in Chicago ready to play with a man who has skills. This game ain't for sissies or mommas boys. I know what I want and you know what you want so this whole thing should be uncomplicated and simple. You know the game, it's straight forward and goes as follo...
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...
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...
Totally new to this kind of thing! I use a couple of apps to do dating but I am never tried this site before. I am hoping I came to the right place. Are you my Mr. Right? I hope you are not my Mr. Wrong! My name is Lisette and I am 26 and single and I love to go to the beach and the movies. Check out my profile page and send me a mes...
🌟 Handsome JOHN Seeking a Spark 🌟 LET'S PLAY SOME Hello there, lovely ladies of Chicago! My name is Johann and I am on the lookout for that special someone who can ignite a fire in my heart. 💖Swap pics & contact info I have a passion for exploring the great outdoors, whether it's hiking through the mountains or relaxing by the lake. �...
I'm Your Sexy Guy... ALSO BI 🍆💦 Chicago I am here to rub you down to a state of complete relaxation and release from all your stress. I am a student of somatic massage and would love to use my techniques all over you. I only do out-call at the moment. I am located in Chicago but I am happy to travel anywhere,,,   Gay M4M - Deep Rub...

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