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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March 4th, 2025
Chicago Fetish Lover seeking hot, kinky fun! Chicago Fetish Lover for Hot, Kinky Fun!
I am a seriously fun woman who has a naughty side. I have never put an advert on here before, so I hope I am doing this right. I just turned 28 and I am about 5' 6" with a curvy body and slender legs that go on forever and look great in stockings.
I love ki...
I'm Top Bitch! Get a Taste of Femdom!
I'm Mistress TopBitch here in Chicago, and I'm going to pound and drain your worthless asses of all self-respect, and you're going to fucking love every damn second of it! Strap-ons and pegging lesbians are my speciality. (among other things) If you are all filled with fear a...
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 ...
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...
🌺Ebony Godess🔥TIME TO PLAY! Your Ebony Sex Doll - Chicago😈
I am affectionate, classy, mature, independent 420 friendly, Super Cute💋 Ebony Woman seeking.
My Profile and Pix Here 💌 I love Kissing and Making out.🔹♦🔹 Nice and Sloppy. I want a secret Fuck. I can host or come to your place&...
🔥 Savor Sensual Delights with a Curvy Cutie in Chicago! 🔥 BBW in Chicago, IL - Looking for Love Tonight!! Seeking a woman who embraces her curves and sets your passions ablaze? Look no further! I'm a BBW beauty in Chicago, overflowing with warmth and sensuality, ready to sweep you off your feet. View My Pix and Message Me - Imagine indulging in tantal...
DoobieSisters Looking for Smoke Buds... DoobieSisters we are hot, sexy and are here seeking generous gentlemen with weed for girls in need. You won't need anyone else to smoke your blunt from now on ;) Come check out our new improved Chicago profile and lets cut out the middleman if you know what we mean! Click here to introduce yourself ...
Newly Out Looking for love Newly Out Lesbian in Chicago
I have only been out for a few months and I am totally new to the dating scene. I have no idea even what to say or where to start! I will tell you a little about me. I am a youth worker and I have a college education. I am 26 and sort of tomboyish but I do wear make up ...
Mature Retail Manager looking for Serious Relationship Retail manager seeks serious relationship in Chicago
My lifestyle doesn't make it easy for me to meet people. I have recently moved here from Montana and I would love to meet someone who is light-hearted, fun, carefree but also responsible and intelligent. My name is Mandi.
I'm 41 years old and I ...
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 @MilkChocolateFem me if you like a taste of hot chocolate!
MilkChocolateFem in Chicago...
Shy femme needs love from butch woman in Chicago Femme for Butch in Chicago
Hello. I am Jemma and I am 24 and very shy. I work Tuesday through Saturday and so my weekends might not be the same as yours. I hope you can accommodate me.
I would like to meet a butch lady who looks so handsome, has short hair and long fingers. Please send me a messag...
Englishman Without His Butler... It's a hard life for an Englishman not to have his butler in America, but I have learned to adjust. The really hard adjustment is not having a good woman and best friend. Moved here to Chicago about 3 years ago from London to work in the tech industry and do rather well despite the sky-high prices a...
exciting black guy waiting for you Exciting black guy in Chicago
I am Herman. I am an active and fit, age 32, black male and I am excited to meet you! Looking for lovely lady of any age but not too old to keep up ;) I am fit and fast to run with and muscular. Tall and attractive. Want to work out? Travel? Coffee and lets see where i...
Caramel Complexion male seeking night of pleasure Hey guys! I'm a gay man, looking for someone to discreetly play with. Hookups are great but an ongoing FWB would be even better. I'm age 31, 6'2 and have a thick.. well, you'll find out ;)
Let's swap pics first and then meet up in Chicago.
CaramelSurprise31...
You want to date me, right? Man seeking Woman in Chicago
This is Noel and I am here to let you know that you don't want to miss out on dating me. i am a joker but not a smoker but I love to laugh and make you laugh too. I am a music fan and I love going to live gigs. Shoot a message to me @Noel4Fun if you are on the same...
Joker and a Smoker... I'm a 30 year old, 6'1, 200 pound hardcore biker living in Chicago and I go by the handle of Joker. Looking for my sexy road queen who preferably smokes too, or at least doesn't mind that I do. All this anti-smoking shit brings out the rebel in me, and if you're like me then we'll get along gre...
Flirty thirty-something Lesbian wants party goer Flirty Feminine Lesbian to Party in Chicago
Ok, maybe not always partying but I do love dancing so much. I can dance for you if you like! My name is Selina and I am half Spanish. I speak both English and Espanol and love to travel when possible! I work from home, even at the moment and I love the p...
Gay Russian Bear New to Chicago... My English is not so good yet. I am Vlad from Moscow, Russia and want to find gay young man for sex in Chicago. I am 34 years old, 6'2, 210 lbs, blue eyes, big size penis, not cut, stay in good shape and love good party.
I am here for 3 years, engineer and single, but still no car. If you are...
Lesbian horse lover wants to meet same Hello girls! I am Sammi and I am nuts about my horses. I have three altogether 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? Send me a private message or text! "SammiCowGirlx"...
Maybe YOU could be teacher's pet?! Chicago Lesbian Seeking Life Companion
Hi, I'm Jen, mixed race lesbian female 34-years-old, 5'7, 150 pounds, working in the Chicago School District and am looking for something more stable and long term. I love kids, (have 2 of my own three days a week) I teach 5th grade english and social stu...
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RuPaul Step Aside! Fashionista looking for my model boyfriend! Drag Queen Extraordinaire Silvia
My name is Silvino but on weekends my name is Silvia! I love dressing up and I do drag shows. I am not totally flamboyant but I do like being noticed. I love classical music but I also love, love love dancing the night away at clubs!
How about you? Check my pr...March 3rd, 2025
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. ...
Chicago 💓full service+bbj, european girl 📲HMU Swap Pics & HMU and Check Out My Profile
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💎I provide a very erotic, sensual massage session.
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F/M seeking love and fun Female to Male Trans Man in Chicago
My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and other times I let it gro...
How do I look? / M4W in Chicago Man for Woman in Chicago
Check out my profile and tell me how I look. I am Sam. I'm a model, age 32 and told I am darn hot looking. Hit me up and check out my profile @SamChicago. Send your pics for mine. I'm available evenings and weekends.
Sorry guys, no men.
I appreciate femin...
Young, Fun, Perfect body and 36DD looking for nice gent to date Young, Fun, Perfect Body and 36DD
26 yr old looking for fine looking man, with fit physique. Must enjoy sex! I like being active and enjoying life. I'm giving online dating another try.
My Pics and Contact Info 36DDblonde
Send your photos and mobile# for mine. Tell me a little about yourself...
Long and hung Wants night of fun and more Long and hung... Now that I have your attention, my name is Luke! I am a 28 year old Barista and I moved to this area 3 months ago. It's a weird time and I want to meet people I can hang with. I want a guy who will listen, make me laugh and generally be an all round good dude. Not fussy on appearanc...
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...
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 a Sexy and Naughty T-Girl Here in Chicago. Chicago T-Girl 4 NSA
Fabulous Fanny here boys! I'm a trans woman living in the Chicago area. Sweet, sexy, friendly and outgoing. I will definitely make you feel happy/sexy vibes and relaxed. I have an amazing body boys. I'm a pretty t-girl with a big present! So forget all your worries and st...
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...
Sophisticated Black/White mixed Lady wanting Gentleman friend in Chicago My name is Janette and I am 32. Some men have been intimidated by my 36D breasts, with big sensitive nipples, but I am hoping there is a man out there who can cope with them! I am passionate and responsive and give pleasure just as freely as I receive. Don't be afraid, I don't bite... too hard!
Mes...
Not exactly out yet. Need discreet NSA... Mixed mexican/white male 29yrs, professional divorced with two kids. I am looking to explore my bi-sexual curiousity in the Chicago area with the right man and see if there is anything there. If you can be discreet and are interested then please come see me by clicking here....
Wife Swap in Chicago Anyone? Swingers Seek Sexy Swap in Chicago
Hi we are Dave and Lisette here in Chicago. Admittedly we are pretty new to the swinger lifestyle and don't want to cross any boundaries, but we would really like to find a couple around our age to swap partners with. You don't have to be married like us, just in ...
Looking for a Smooth Operator in Chicago... Let's See How You Operate!
Hi all I'm Arlene a busy surgical nurse here in Chicago looking for a guy who is smooth like Southern Comfort. Not brash and overly cocky and overly sure of himself. I need that silent strong masculine energy in my life that tells me I'm a woman and makes me glad to be so...
Wanna play threesome? Me and hubby have been together for fifteen years now and are happily married. We live here in Chicago and are adventurous as well as fetish friendly. We want to find a third man or woman to come play with us for some adult fun. Of course we will have to meet to make sure everyone is feeling it. You...
LOCAL LESBIAN NEEDS❤️ Women 4 Women only ( NO MEN ) I want to meet a lesbian tonight! 👅
Looking for a sexy lady to play with tonight, W4W Women Locally in Chicago only or near by... I'm strickly lesbian. I love pussy, I love boobies. I'm living in Chicago in. I'm willing to travel or I c...
TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Chicago
Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
Wild and Crazy Girls Looking for Some Man Meat in Chicago Bi Girls Want Threesome in Chicago
Hello boys we are two bi girls (Linda and Emmy) looking for a sexy man in Chicago to join us in some hot fun. We tend to be a little kinky so you'll have to get to know us a bit first. You check us out, and we check you out sort of thing. Come on, it'll ...
Looking for a 420 Friendly Girl Tonight... Come on over and smoke my blunt baby! This will be an NSA boobies for doobies exchange. If things go right we could be steady smoke buds. I got the weed if you got the need. I'm Mario a Latino man, 25 years old, great shape, love the bud and women. This works out for the both of us. If you're jonesi...
47, 6' 2 Man Seeking Woman for Dates in Chicago
Hey, Richard here. I just want to say hi to you and hope you might check out my profile and see if you want to date me. I am just a regular guy looking for a regular gal. I've been single too long. It's time to meet someone special to enjoy the fun things in l...
Flawlessly gorgeous trans bombshell in Chicago Trans MtF for Man in Chicago
I transitioned 6 years ago at the age of 18. I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am short and cute and I have bedroom eyes and luscious lips. Check my profile pics @TransFaye24 pics and prepare to be stunned!
Send ...
Half Asian female wanting affection in Chicago I am half Asian with a dark complexion. I am here studying and I am lonely. I would like to meet a nice lady I can be friends with and hang out for fun and hopefully sex. Send me a private message to MelodySingF...
Your Ultimate Erotic Experience!! Don't Miss Out!! I am very honest, sweet, and loving young woman, I am a Christian, that is my background, religious and I believe in real love, I am here looking for real love and a man that I believe I deserve, I love cooking, dancing, cleaning, watching movies, I am down to earth outgoing woman. I have been in an...
Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice!
Hey boys, my name is LethaWeapon here in Chicago and I got a BIG love gun to whip and pound you with until you scream! I'm def top and alpha and don't take no shit! Imma make you suck me first just for foreplay then I'll throw you back for some hard insertion,...
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 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! ...
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 ...
Czech Beauty new in Chicago Ahoj, lásko. Rád bych se s vámi setkal a hledal jsem vás. Kdy se s tebou m?žu setkat? Jsi tam venku? Kontaktujte m?.
Hello, my love. I know you are out there somewhere. I would like to meet you and have been looking for you. I like texting and sharing sexy thought...