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

Tranny Cock🍆Chicago Transgender HOOKUPSin Chicago, Illinois 🍆❤️😉  Check My Profile and and Dm MeI'm in the Chicago, Illinois.. area. I'm willing to travel. As longas you love TGirls and Shemales..I want to have some sexy hookups..I have some fun things in mind. I would loveto connect and see w...

I'm just here for the MEN! I'm Gina, 30 years old, 5'5, 130 pounds, 36D and here to pick up on a sexy man. Sorry no great pickup line or anything and not a very good ad, but I love men and am not afraid to say it. Just broke up and don't want a full time relationship just yet. I am looking to have my needs met just like ...

Star Wars fan looking for his Obi-Wan Rudy seeks man in Chicago  Name is Rudy and I'm looking for a man in Chicago. Are you out there somewhere? I am looking for you. I love Star Wars. Possibly a little nerdy ;) Would like to have light saber fight with the right guy. Private message me @GayNerd4m...

Hot Girl Wants To Hang Out With Woman in Chicago Are you cute and fun? I'm lonely and looking for good times with someone special. Just send me a message @HotGirl4XXXFun and I will send my recent pictures. Please send your pics and contact number. Let's text and go from there. Local girl looking for local female friend to hang out with and m...

🌹 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 ...

Do you know the difference between a dick and a bucket of popcorn? You don't know? Well then take me to the movies baby! Mmmm think of all that creamy, buttery, salty goodness! Talk about a double feature. lol Hope you have the munchies for this hot Chicago tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer than...

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...

31 Years Old in Chicago, Sugar Daddy Arrangement!! Seeks a Sugar Daddy Arrangment in Chicago I don't care so much about your age but you must be fit and healthy and able to swim and snorkel! I love anything in the water and usually maintain a tan! I am active, fun loving and they say I am attractive! My name is Phillip and I am 31 and I have a dema...

Dr Freakin'furter - Mine's Bigger Than Yours! White T-girl here and I'd bet mine is bigger than yours. We'll just let it be our little intimate surprise when the time comes. No one needs to know our business, Let's just keep it discreet. If you live in the Chicago area come see if you measure up! Click here for explicit photos. Look f...

Attractive, Dark haired and Slender - Brunette28XChicago I am tall, slender with dark hair and deep brown eyes. My interests include running, hiking, biking and horse riding. I am an account manager and I have just moved here. I am looking for local friends with a view to dating and possibly more. Send your photo for mine. Hit me up for a date and send m...

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 ...

Asian Lilly 👩‍❤️‍👨 I'm Horny Tonight Asian Lilly - Looking For Man!I'm Local in Chicago  Sex😘 Looking for a genuine sexual relationship with a like-minded asian lady? ( Do you want to view my personal profile and my sexy pictures? ) Look no further! As an Asian woman, I value deep sexy connection and meaningful fantasies....

Hot and kinky MILF looking for some fun in Chicago Chicago MILF For Kinky Hookup! Hi all you sexy Chicago guys, I Georgia and I am an slightly off beat working professional mom of two. MILF. Just looking for some sexy fun and to explore my (and yours?) kinks and fantasies, FWB. I am into men, but possibly women or even a hot couple depending o...

Hey Boys The Show is Over Here! Diva Seeks NSA in Chicago Sure I'm a diva, who isn't? I'm London here in Chicago looking for a sexy guy who gets me. Not looking for anything serious right now, just a NSA hookup with a handsome guy who knows how to please a woman. Hey, it's not a one way street I know that. I'll take goo...

you+me=😈Sex Buddies😈 Fit Man Looking For Fun!! (M4F)😉 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! 😉- My ProfileI love lots of foreplay, kissing , giving and receiving lots of orgasms. I am very oral i love...

Tiffany Shelle - Your Chicago Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Chicago It’s Tiffany Shelle your perfect tranny girlfriend 🥰 💕 SAFE💕 💯 LEGIT ✨💞 SKILLED, Exotic and Erotic 💦 🥰 I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% functionin...

Wanna play threesome? Illinois Couple 4 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 sur...

Cerco signore americano di lingua italiana a Chicago Bellezza italiana Cerco uomo di lingua italiana a Chicago Mi chiamo Erina e vengo da Roma. Se si può nder stand questo si prega di testo me così possiamo incontrare. Voglio un gentiluomo americano di lingua italiana per amore a lungo termine. Sono nuovo a questo, quindi per favore sii...

Short but fast runner likes to meet fitness partner in Chicago Hello. I am Justin and I am a fitness freak. I love all gym workouts and I pump iron almost every day. I have to work from home right now and my outlet is my home gym. I am 42 but look pretty young. I guess I need something fun to do besides working out. Let me work on you! Check my pictures and se...

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...

Here to be your sexy little slut.... Slut in Chicago Wants NSA Hey you sexy men in Chicago I'm Jill and I just can't help it when I see a hot guy. I fall in love (or lust) and want him to kiss me, touch me, and squeeze me and be in me. There are lots hot guys around here and I know I can't have em all, so here I am to get at leas...

🔥 Looking for My Partner in Crime 🔥 Hey there, lovely ladies of Chicago! My name is Kip and I'm on the hunt for someone special to join me on some exciting adventures. 🌟 I'm a hopeless romantic at heart, always looking for ways to show my affection and make you feel like the queen that you are. 💖 I believe in chivalry and treat...

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...

Cunning Linguist... Oral Expert Seeks Woman in Chicago Hi, I'm Calvin a single male in Chicago looking for a single woman who is funloving and passionate. I am orally gifted and speak fluent English and have an accent. My greatest oral talent however is in my long tongue - my whiskers are soft and tickly, but not...

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 ...

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...

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...

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...

!!!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...

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. ...

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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...