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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May 14th, 2025

Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Chicago Look no further honey, I'm Franny an Ebony trans woman here in Chicago to fulfill your wildest fantasies. Dreams really do come true when you are with Fabulous Franny. I'm all about the frills and the thrills baby! We can freak it and they don't have to ...

Italian sweetie looking to taste your fruit Woman seeking woman in Chicago Amante dolce in attesa di assaggiare la vostra pelle. Riesci a leggerlo? Parli italiano? Voglio parlare con te. Inviami un messaggio @DolceAmante. I speak English too! Sweet lover waiting to taste your skin. I want to talk with you. Send me a message @DolceAmante. S...

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 ...

Shiny blue eyes and 34 years old. Man for Woman Dating in Chicago Hi, I am Brandon and I am 34. I am excited to meet a loyal and loving woman who can complete my world. If you would like to say hi, come and see my proflie and message me for pics and contact info @BRANDON34M....

Just Got a Delivery of Kinky New Toys! Young lesbian girl Robbie just got some kinky supplies with lots of batteries. If you are into some kinky fun and live in Chicago then HMU for a good time. I'm 21 years old, bit of a butch/tomboy type who is just now getting into fetish play. Got some bondage gear, pumps, whips, gags, electro stimul...

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....

May 13th, 2025

A Hot Fucking Game Of Four-Some Roulette. What Kink Will We Choose? HotWife? GangBang? WifeSwap? - Username: @JNDSwingingCouple- Location: Miami, Florida- Ages: 23 & 26- Swingers Profile: Yes- Hotwife Pics: 57TEXT DIRECT FOR BOOKING INFORMATION- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials We are Julia and Derik - I'm a Hotwife and He likes to watch and join in at the ...

Bosnian Beauty wants a date I am new here in town and I would like to meet a cute man to go to dinner with. If you are interested please send a message to me. @BosnianBarbie Bosanska ljepotica želi spoj Ja sam nov u gradu i želeo bih da upoznam slatkog muškarca sa kojim ću da idem na večeru. Ako ste zain...

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...

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...

Jaw Dropping Hot Lesbian Hot Lesbian Seeking a Female Lover in Chicago Did that get your attention? I hope so. I am looking for my perfect partner. Someone fun attractive and intelligent. She should to be neat and clean and not untidy around the house, easy to talk to, laid back and attentive to her partner just as I am. ...

TS m/f switch 28 new here TS m/f Switch in Chicago Sandi wants to meet hot guy for fun and hot sex. Age 28, nice build. Non op functional. Love oral sex, anal sex and kinks of all sorts. View my profile and message me here @SandiSwitchTS...

Discreet meet only in the Chicago area!!! I am Jamali here in Chicago for a while doing some work for a tech company so I can't get too involved with anyone. I'd like to get out and experience this town, the party vibe and the men in it. I'll be going home in a few months. If you are iinterested in an Asian-Indian man then come check me out...

I've Been Naughty and Need a Spanking!... If you are a sexy disciplinarian man in the Chicago area and have a strong hand I NEED a spanking to get my juices flowing. (oops! I meant to say to pay for the bad things I've done!)  I'm an Italian/French girl 22 years old w medium build, and an appetite for punishment and erotic NSA encounte...

Holy Capped Crusaders! - We'd Make a Hot Dynamic Duo! Bottom Boy Wonder searching for his BAT-man. Twink 24 years old, 5'9, 160 pounds in Chicago seeks cosplay leading man to form a dynamic duo. We may not exactly fight crime, but we will have lots of sexy roleplay fun. Let's travel and go to conventions and events and contests! We'll take the world by...

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...

Lookin for the big one? What a silly question. Of course you are! Well, I got the big one for all you size queens out there in Chicago. I'm Frank part Italian and part many other things. Here looking for the same thing you are really. If you want to find what you are looking for here I am hung like bull. Nothing small abou...

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...

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 ...

New in Chicago. Lesbian Bondage Anyone? My name is Michelle and I am ready to meet the girl of my dreams to explore the world of bondage and light BDSM in a safe and erotic setting. Send me a private message if you would like to swap pictures, chat and meet up. Attractive, fun, slim build, light hair. Let's see where this leads us!! Us...

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...

Hey guys, I am looking for someone exciting and funny! Is that you? Cassie seeks charming and manly guy! I want someone sexy and fun. Clever and sweet seeking charming and manly guy. Please text me if you fit this description, or just hit me up me if you like my pics! Cassie89ooh I enjoy dining out, movies, hiking, travel, other cultures and sports. Did I mention ...

Italian hot woman looking for love Adriana Hot Italian Woman i guys!  my name is Adriana and I am from originally from Italy. I moved here recently and want to meet a nice friendly, fun guy. I own my own private cozy place. I am friendly and a fun girl. Message me. See you soon! ~ Adriana in Chicago...

I'm Sexy and I'm Noah!... Single Black Man 4 No Strings in Chicago Black male, 33, 5'11, 180 pounds, with a good education and positive attitude from Jamaica originally. I have lived here in Chicago for about 10 years and love it. There is always something to do. I am looking for an original woman. What I mean is some...

SUGAR DADDY 🍭👨‍🦰 💦Looking 4 Play Boy M4M Hey there babe, I'm a 25 year old male who is searching for another guy to play with and spoil. I'm strong and muscular, I drive a beautiful car, I can take you to do things you've always desired 🤑 It turns me on so damn much to find a cute little man to play with and take care of. Let me be D*dd...

Caught My Boyfriend Cheating... Now it's MY TURN! Looking for some hot NSA revenge sex with the right guy in Chicago. Must be STD free and have your own place or arrange for a room. I will not give you my real name or address here. I'm a 24 year old, 5'7, slender, blonde haired, blue eyed female seeking a sexy man. We'll have to chat first and meet...

European Lady seeks sensual gentleman European Lady in Chicago My name is Karena and would like to meet a kind gentleman for dinner and dating. I am mature and I originate from Europe and moved here recently. Serious callers only and I am willing to please you.  Check my website pics and contact info KarenaXX86...

Cheating on my BF🤫Discreet I'm Here to Have a Discreet/Cheating Profiles 🤫 My bf and I fight so much, It sucks. I want out of therelationship but first I thought I would try to play thefield and see what's out there. I want to cheat and have some wild sex tonight. Are you man enough?Going out an...

Flirty Fun, Endless Kisses & No Judgments 💋 Chicago  The person I am today is a relaxed yet passionate man who balances his gentlemanly nature with  flirtatious tendencies by sending sweet messages during mornings and provocative messages at night. 😈 I enjoy tasty  food with slow kisses and unexpected plans that typically lead to in...

Hot sexy shemale doll visiting Chicago now Shemale Visiting Chicago Very hot sevy and curvy shemale chick with big delicious lady stick. Message me on my profile page @TaylaShemale1. Seeking kind gentleman for romance and fun. Possible long term with the right man. ...

TS Temptress Ready to Ruin You (In the Best Way) 😈💦 Chicago  Hey lover 😘 I’m a high-femme TS bombshell — curves for days, lips  made for kissing (and more), and a hunger that doesn’t quit. After dinner I appear sweet  but I transform into a woman who crawls to the bed naked while wearing only a mischievous  expression...

Spanish Gay Man Needs New Owner... Hi, I'm Shaggy a sub from Madrid, Spain originally and just moved to Chicago about 5 years ago. My English is good, I'm 32 years old, 5'9, 170 pounds, very skilled in bed and very passionate. I need someone to own me, take me, use me and protect me if only for a short time. What do you say amigos? I...

Super hot guy waiting for girl of my dreams Black Man for Romantic Woman in Chicago Dark chocolate man with romantic nature. My name is Dwayne and am 6 feet 3 and well built. I am into sports and I love watching football. Life is good and all but I want to meet a beautiful woman for passion and adventure. Check out my profile @DwayneSeekingR...

GangBang Island - Only It's Your Ottoman and I'm On My Knees Begging For Cum 😘🔥🔥🔥🔥 Let's Make Each Other Cum Over And Over And Over... - Username: @AsiaMay8364- Location: Chicago- Swingers Profile: Yes- Hotwife Pics: 29TEXT US DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials I wanna be your sex slave and bf will stand to the side and watch the games....

Widower seeking affection in Chicago Chicago Widower Seeking Affection Hello ladies, my name is Jonathan and I am seeking some female company for fun times and affectionate days. It has been a while and I have to face that I'm lonely. I am 52 and still look in my late thirties (I am told) and I am fit and healthy. I love riding horses...

Irresistible woman desiring to be wanted Hello, I am originally from Portugal and would love to meet a handsome, funny guy to do to movies and dinner with. I am new to this online dating scene but hopefully, you will be nice! Please message me!  IberianLady1 Olá, sou natural de Portugal e adoraria conhecer um tipo bonito e eng...

Looking For My Lesbian Cosplaymate in Chicago... Im Bethany into cosplay, roleplay and women, but not necessarily in that order. I need a lesbian, bisexual or bi-curious cosplaymate in Chicago who likes the world of fantasy like I do. By day I'm a mild-mannered beautician, but when my alter ego comes out I'm your super hero, or sexy housemaid or a...

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...

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...

Princess Mai Rules Chicago! Cruel to be Kind in Chicago Come bow down before Princess Mai of Chicago and I will rule over you. I will control your life, your comings and goings, and who you can or can't talk to you sneaky little bitch! When I text you better answer and be at my service. It is your duty and pleasure to appease...

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...

I'm a Steamroller Baby! Hi ladies, James here nice to meet you! Let's hop on my bike, put our knees to the breeze and do whatever the hell we please! I'm good with my hands, still a bit of an outlaw at heart, 35 years old, lived here most of my life, blonde hair, blue eyes, 6'1, around 220 pounds, muscular, love women, hug...

💎 Adorable Sugar Baby 💎 Seeking his Generous King 👑 📍  Location: Chicago    Seeking: A kind/dominant daddy👑  A Little about Me: Hello everyone! I am a sweet, fit blonde with a flirty nature  and an appreciation for the good things in life. I enjoy being pampered, looked after and treated  like a king. If you a...

Let's indulge ourselves in something extraordinary... Hello there boys I'm Tawana a 24 year old ebony female seeking a sexy man for some hot NSA in Chicago. I'm actually from here and prefer a man who lives here instead of a long distance thing. Mostly because when I'm hot and ready and I need you I'm gonna need you now, and not whenever you can get he...

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 ...

Deep Throating Is The Game - Wanna Play? 🍆👅 Raw, Uncut and Everything I Want in An Orgy - Username: @SuckkinOnThemDicks- Location: Chicago- Swingers Profile: Yes- Hotwife Pics: 27TEXT US DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials Everytime we post an ad like this we end up completely swamped with messages ...

Erotic exotic Asian queen in Chicago now (25) Asian Transexual in Chicago Stunning TS - Talia 25. 5' 8" 140lbs, non op, loves sex. Long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information....

I am a hot lil sissy living in Chicago - HMU!... Black Sissy Boi in Chicago Checking this out online, never been at this before. I'm Charles a black male, 155, five foot 5, w long and skinny as you can see in my hot profile pics. Just looking for a little sexy adventure here in the Chicago vicinity. Click here for more of me......

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...

Let me be your freak! Let me be your freak. I love to do threesomes with you. Does your wife like pussy, or do you have a friend that would like to join? If so, don't hesitate to get in touch with me now and take care of me. Username on Get An Escort: @FreakSex >>> CONTACT ME & MEET ME<<< More FR...