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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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January 22nd, 2026
Hot chick looking for more than a good time I am told I am hot. That's up to you to decide, but I would definitely agree to some extent! I am fun (I think) and I love good food and a good time.  I love intimacy and good sex! 😈 I like to take pics and do sexy videos. Wanna swap your hottest pics for mine?  Text me at SherryS...
Well Endowed Shemale is beautiful Chicago 32 Well Endowed Shemale in Chicago I am Blanca. I am ready to eat your manhood now. Top or bottom. Bareback if you're clean. Come say hello. I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me @BlancaShemale32 with your recent pic or selfie for my latest pictures and pr...
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...
We’re a couple (male female) looking for a male in Chicago... Try a Kinky Threesome With Us! Bill and Maria here looking for a man who would like to explore some kink and fetish here in the Chicago area. We are both bisexual and want to try out some new things with a man who is sexy, open minded, well groomed and around our age (21 - 32 or so) Of course this ...
Swingers With a Glory Hole Fetish in Chicago Join Our Glory Hole Parties! We are Milo and Ashley here in Chicago looking for other swinger couples and single men to join us for some glory hole action tonight. It is a big fetish of ours. We have a large home with a room renovated and dedicated to those who want to try it out. Usually what we d...
T-Girl New to Chicago and lonesome! I Christina and am a trans woman, 33 years old, 5'9, highly skilled and new here in Chicago. I would like to meet a handsome gentleman to go to dinner with. Not only am I lonesome, but I'm horny too so buckle up and hold on tight! After dinner just ride me hard and don't hold back big boy! Message m...
Luscious Lesbian With Angel Arches and Princess Toes... I'm Nina 25 years old and my sweet feet really turn me on. (as they will you) I need a lesbian, bisexual or bi-curious woman living in Chicago to worship my feet at least as much as I do. (and that's a lot) Access to these sexy feet is a privilege to die for. To see them fully naked would make you s...
!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Chicago Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Chicago to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enjoy 24/7 Online Chat M...
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...
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 ...
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...
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,...
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...
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 ...
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...
I'm the Girl Your Mum Never Warned You About!... But then, how could your mother have known? I'm Dirty Diana corrupting good decent honest men like yourself here in Chicago for many moons. I got a big secret and it's show and tell time baby! It's easier to show you than to tell you. I'm fully functional and passible. I need a sexy man who lives ne...
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-curious clie...
I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Chicago I'm queen Delilah a trans woman here in Chicago searching for her king. You'll get the royal treatment when you're with me honey! Just grab hold of my magic scepter and his majesty can have anything he desires. Imagine the intrigue and scandalous position...
Just Give Me a Man - Any Nationality Will Do! Mina Needs a Man in Chicago! I'm Willamina here in the Chicago area, but go by Mina with friends and family. If you are a fun loving, passionate, stable, sexy guy with morals then you have my attention! I find all types of men attractive, so I can't tell you what kind of man I am looking for exactl...
Half Asian female wanting affection in Chicago I am half Asian with a dark complexion. I am here with my sister 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. I am from a conservative family so please be discreet. Send me a private message to MelodySingF Usernam...
Here I am! Hookup with a smoking hot grandma in Chicago! You might not think so but older women still love having sex. Come check me out and see why women get better with age! I'm gonna show you what you don't know now. I'm Sherri a retired teacher and school administrator in Chicago. My friends are all settled down and traveling in their RV's, but NOT ME...
Smoke and Leather! Smoke and leather go together. I'm Toby, 32yrs, 6'0, 200 pounds, extra large, living in the Chicago area, a hairy thug, def top gay man wanting to pound gay, bisexual and bi-curious men. Just be ready to pleasure me while I chain smoke. I don't care if you smoke or not just be damned grateful that y...
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...
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 or couples. I appreci...
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 ...
Superb Shemale in Chicago... T-Girl for NSA Encounters in Chicago When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Chicago. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle, f#ck and ...
I Need a Body Rub Followed by a Naughty Rub! Hey gents I'm Lauren, 24, hard worker, large boobs, brown hair, blue eyes and 5'5, and I want a full body massage if you live in the Chicago area. About me: Sucker for a good long massage, a major turn on! About you: sensual stong hands, stamina, know the female anatomy and be a quick learner of toy...
Hello! My name is Alexis in Chicago Sex Hookup in Chicago If you are looking for someone to entertain you and be your ultimate fantasy girl, that is me. I am hot and sexy and want to hook up with someone with warm feelings and a bright personality.  Send your pic for mine.  AlexisXoXoXo If this ad is online then I'm availa...
Say BootyJuice Three Times and I'll Be There for a Threesome! Ebony Babe Wants Threesome in Chicago Sataay here in Chicago lookin to freak it with a white swinging couple who need some hot chocolate. I will make an exception for mixed couples as long as one is white. It's a fantasy thing. I got big boobs, big booty and a big ol dirty mind! So come on by and s...
Selena, mujer latina solitaria en Chicago Selena, mujer latina solitaria Hola, mi nombre es Selena y vivo en el centro. Me gusta pasar el rato y relajarme y quiero conocer a un tipo genial con el que jugar. Golpéame (SelenaSexyDivertido29)...
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Tall & Peggable 😈💋 Looking for My Boss Babe Hi I am a Single 32 years old straight white male.I'm in Chicago and I would love to meet and amazing woman who wants to feel a real man! 😉 I love lots of foreplay, kissing , giving and receiving lots of orgasms. I am very oral i love to give as much as receive. I love to make her cum all ov...
💦 Midwest Heat, Let’s Link & Sweat 😈 – Illinois Edition What’s up, Illinois? I’m a laid-back, masculine guy lookin’ to connect with another man who’s down to get into something real, raw, and ridiculously hot.I’m into chemistry, dirty talk, deep kisses, and deeper strokes. Whether you’re curious, experienced, or just i...
TS Sugar Baby💎 Your Perfect Trans Fantasy – Let’s Make It a Reality 💋  📍 Location: Chicago 💖 Seeking: Fun, Exciting, &  Discreet Connections Some about me.. Trans SugarBaby: Hey there! I belive I'm a stunning, sweet, and playful trans beauty who loves good  vibes, great chemistry, and unforgettable nights.. I'm in my early 20's and I'm...
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Looks Innocent. Absolutely Isn’t. 😇😈 Sweet in Public, Unfiltered in Private A grin slips out, then comes the quiet reply - thank you, yes, and sweetness stays visible here 💕Still, once the curtains shut, I refuse to trim who I am. Message Me Here 💬  Something about quiet sparks, long stares, one talk that grows soft then j...
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College Guy Looking For A Fuck Buddy In Chicago Are you near Chicago? I am looking for a fuck buddy to fuck around with from time to time. It would be great if you had a place, or we can do car stuff. I am 20, fit, 165 lbs and 5ft 8. Prefer men under 45, but men can be hot at any age. Love uncut guys, but it's not required. Send me a message and ...
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I need some sex. I'm looking for a sex date. It's been too long without it. Suppose you want an NSA sex date. Come check out my profile here and link up. I love to take care of you. Username: @SexyFuck >>> CONTACT ME & MEET ME<<< More FREE Adult Classifieds SitesJoin them all in 30 seconds e...
Fuck Me Like Your Bitch Won't Let You. (Ass Up/ Face Down/ Anon) I'm not looking for small talk. I'll be ass up, face down, and ready for you to fuck my brains out. Looking for someone that knows how to destroy an asshole. 100% anonymous, I don't care to see your face. All I want is a deep hard fucking until you blow your load all over my guts. The deeper and har...
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29, Swimmers Build, Looking To Fuck Tonight - Host or Travel Title says it all, looking to host or travel. Looking to fuck all night. I am hung with a 9 inch uncut dick. Verse, but more of a top. But if you have a nice cock, I'd be riding you in a heart beat. More into the vibe of the guy than worried about age or looks. Hit me up and see if we are a match. ...
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