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 5th, 2025

The Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project Proudly sponsored by Chicago Lesbian, Gay, Bisexual & Trans Dating Community The Trevor Project Donations, by Megan Morrison BonePage.com proudly supports The Trevor Project, an organization dedicated to suicide prevention among lesbian, gay, bisexual...

Intense, vibrant and dark haired beauty, WLTM handsome fun guy Intense Dark Haired Beauty in Chicago Hey, I'm Janey and I'm still looking. I'm kind of bored and need new friends and maybe some romance. I have dark hair, soft skin, sultry eyes and a great smile to make you happy. How about you? Why not call and let's see where things go? Message me now #J...

Asian Lilly 👩‍❤️‍👨 I'm Horny Tonight 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.. I'm seeking a man who shares those same values and is open to explori...

Keep Calm And Have A Threesome in Chicago! Swinger Couple in Chicago I'm Daily and my hubby is Don, we are in our 30's, live here in the Chicago area and are swingers looking for a sexy man and or woman. We love role play as you can probably tell from our pics. We can be a little kinky I suppose, but mostly we are into adult role play and N...

Jon Boy seeking Chicago Top Male to Pleasure 👅🍆💦 Kink friendly bottom male Hey, thanks for checking my ad. I'm Jon Boy, looking for a hot gay man who's ready to play with me and let me explore all kinds of naughty fun as I pleasure you. Recently out gay male, age 21, seeking other gay, bisexual or bi-curious guys for some wild male-on-male action...

I'm a Snobby Stuck Up BITCH! I'm AllyCat and I need a sexy AF man to give it to me rough and hard and pound me - use me AGAIN and AGAIN! Have your way with me and put me in my place! Teach me a lesson I won't soon forget baby! Make me tap out and then beg you for more. I'm always ready and you should contact me here if you live...

DIVORCED👩MOTHER-MILF?? I am available Every day. Make me CUM and this could be a regular thing. If you want test me in SLIM mom try today now anyone.100% real and legit 🚫NO GAMES 🚫TIME WASTERS 🚫NO DRAM Respect me and I will respect you! I just need some oral hookup all day/night .I can host or come to your p...

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...

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...

I Need an Interesting Man in Chicago... An active imaginative and educated mind stimulates me. I'm Howie, 37 yrs, 5'11, 180 pounds, shaved head, not so attractive, keep to myself a lot, accountant and lover of all things novel and interesting. The world is full of so many fascinating things that I want to soak it all up. If you feel this ...

Naughty boys check me out... good thing I LOVE naughty boys! Kara here, I will make your fantasies come true in Chicago! I have a bubbly personality, enjoy intimate dinners, shopping, and I love as much as I receive. I dress to impress, love to snuggle, STD free, classy, and ready to satisfy the needs of my man anytime. People who know me would say that I hav...

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 ...

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...

Puss N Boots Sexy Puss N Boots Fetish Hi I'm Linda (PussNBoots) here in Chicago looking for a man who has a boot fetish like me. Boots are a symbol of power and that's why serious bikers and Armies wear them. If you love a woman in boots then maybe we should see about a FWB situation. I want you to take me boot...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Chicago I will help you unwind and create a cozy environment for you! I am hot and sweet and can give you so much pleasure. View my Transgender World profile and message me for my pics! @GayleTGirl Gayle 😍 Transgender World Profile Username: GayleTGirl Locati...

Chicago Musician wants to funk you up! Gay Musician 4 Fun in Chicago! I'm Gig (real name) living and working here in Chicago. I'm a cross between Little Richard and Prince baby! Not the serious type and love to party. (music, sex, 420 and drinks) I'm always down for some music playin and singing. But, I'm really here for the men. L...

Hung Black Male Chicago for male action Wants hot male for male sex in Chicago. All races welcome. Want some hot male-on-male action? Well, look no further because DeAndre is here to satisfy all your dirty desires. Private message me @DeAndreXXX24. I love hot dates with hot guys, any race. Pretty much top because I prefer being in charge...

Exotic and Erotic Orlando From Tuscany Italy... For More Than Just a Hookup Ladies I am Orlando visiting in Chicago. Let me take you on an erotic journey of passion and delight tonight. I know how to treat a woman and bring out the sensual romantic in you. Just let yourself go and forget all about your cares for the evening. You will be in good ...

🍑 Thick & Tempting 🍯 Seeking a King to Devour Me 👑🔥 Hey there! My name is  Chelsey and I'm a Curvy Cutie..  I am a 26 year old BBW thick girl looking to meet a hot man for some sexy hookups and dating 💋💋💋 If you are into bigger women like myself, then we might have something special. I enjoy being dominant in bed and taking c...

Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Chicago who doesn't smoke, but has a thing for sexy men smoking cigarettes. Call it a fetish or a kink if you will, but I love it. If done right it is soo sexy and inviting to my senses and gets my motor running every time. Truth is that it's erotic all in it's...

Help! Single and Got That Tingle! Itchy in Chicago Hey there boys I'm Natalie here in Chicago looking for a handy man to take care of some of my feminine needs. Are you talented enough to scratch my itch? Must be skilled, but might take on the right apprentice who has potential. I'll have to keep you on call, because a girl never k...

I’m willing to lie about how we meet... I am a 32yr old half Hawaiian, Samoan, and half German. Born and raised right here in Chicago. I'm 5'11" 190 pounds and have brown hair and hazel eyes. I’m a Disney obsessed, official Netflix movie rater. I’m also a cereal connoisseur and to top it all off I'm an 80’s pop music Lov...

Just a girl from Vietnam in Chicago... Hi I'm Xuan I am Vietnamese living in Chicago looking for a honorable man who might want to settle down. I work at my family shop and am 21 years old with a no boyfriend now. If you not Vietnamese I will teach you, I am good teacher 🙂 I like american food better than vietnamese so we can go anywh...

I just want to enjoy life and practice safe sex Hot Woman for Great Sex @KaycieMaine Check my profile KaycieMaine I am a very good woman and I just want a man who can hold down a good conversation and make me laugh. I have integrity and I am looking for true, real love, passion, transparency and honesty. Please respond only if you are look...

Get Over Here Boy! Single and Sexy in Chicago Baby! Hannah here in Chicago looking for a friend with benefits. Hey just so you know I'm not just another piece of ass. That's not why I'm here, to just add to your body count. At the same time I will not tie you down in a relationship you don't want either. Let's be cas...

Fem Lesbian Seeks Dominant Female for Explosive Encounters!... Hi I'm Eliza from here in Chicago seeking a stong lesbian woman for NSA. Are you uber horny like me? Are you dirty minded like me? Are you into fem girls? If so then contact me and take a look at my profile and naughty pics.  I'm full blooded Italian so you're gonna get lots of passion, good f...

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...

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. ...

I'm a Good Girl, But When I'm Bad I'm Great! White trans woman wants NSA with suitable sexy man for erotic encounters in the Chicago area. Good girls don't, but I DO! About me: 5'8 160 pounds, 27 yrs old, red hair, blue eyes, big D, bottom and 36C cups. I am clean, dress up well and disease free. Don't be shy, if you live in Chicago then hit m...

Navy Vet wants to meet partner for life I am a Navy vet currently on reserve duty. I live in Chicago and I love it here. I wanna meet a guy who is appreciative of my service career but also likes to travel and have adventures. My name is Tom and I am African-American, age 29. Message me to exchange photos and to meet up. Willing to t...

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BBW Lesbian in Chicago Sucker for love BBW Lesbian in Chicago Hey ladies, My name is Joanne and I suck at love! Ok, what I mean is, I love to suck. Definitely a 'boob' woman and if you got em I like em. Message me @JoanneBBWfemChicago. Serious dates only please. Send your photos for my recent selfies. ...

Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Chicago? Hey, I am Jasmin, with a great body and busty. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for hot dates and see where it goes!  Hit me up @SweetJasminT...

GAMER GIRL TO TAKE CONTROL OF YOUR JOYSTICK 💋🍆💦 Gamer Girl for Chicago Guy I'm Sofie, and I'm a naughty gaming girl looking for some hot and steamy gaming fun in the Chicago area. When it comes to gaming I am very competitive. I enjoy WOW, Elden Ring, Hogwarts Legacy, Minecraft, Visions of Mana and more!  When it comes to sex, I love gettin...

Anything Goes Kinky Swinger Couple in Chicago Wants to Meet You!... Chicago Swingers 4 Kinky Play Hi kink fans in the Chicago area we are Josh and Eileen (in our early 30's)  looking for men, women or couples interested in exploring the world of BDSM with us. We have our own fetishes, and would especially love to hear about any of yours that you may have. Not...

Hot chick needs female distraction Will you be my distraction? Hello! I am Lucy and I am so wanting to get out and meet someone who can take my mind off things! Are you caring and a good listener and a good kisser? If you are, hit me up with recent pics and a message @JuicyLucyX I look forward to talking with you if you are cu...

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...

DIVORCED👩MOM/MILF Hey Love I am an older cute girl Horny for sex ,& I love to kiss and suck your dick. Bareback, Anal, Greek, GFe ,bbjs, kiss I love getting my pussy licked while I suck cock. I can host, but, willing to travel. 😘 I have nasty videos for sell💋 I'm 42 Years 🅳🅸🆅�...

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The Ultimate Swingers' Fantasy - Fuck Me WHEREVER, HOWEVER You Want! 👄 Any Fantasy, Anywhere, Any Time - Sexy Couple Wants to Make Your Dreams Cum True- Username: @FantasyWoman54- Location: Chicago- Swingers Profile: Yes - Hotwife Pics: 44TEXT US DIRECTLY!!- Video Chat: Yes- Messenger: YesMy Hotwife Pics & Socials Baby Tell Me, What's Your Fantasy? Is it...

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 ...

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, here I am again.  I recently moved, so I am new in Chicago and have no local friends to hang out with. Would love to meet fun, down to earth guy to explore passion and hot sex. I just need to have some fun and make new friend...

Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Chicago boos out there. I'm a sexy trans woman currently living in large and lovin' every second of it. Hit me up cause I Wanna ROCK too! I'll show you what a real woman can do and everything you don't know now. I'm sex...

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...

James is My Name and F#cking Your Brains Out is My Game! Don't underestimate this Italian/Lebanese twink from Queens. Well endowed top boy (and bottom) will make you tap out and take you to the limit tonight or any other night! I got the endurance to back up my claim and a whole lot of tricks up my sleeve for the right guy. I prefer older bears, but if yo...

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 ...

CHICAGO - black🍆crossdresser  EBONY/BLACK CROSSDRESSER  in Chicago Illinois  👅😉🍆  I've been living in Chicago Il, for 2 years now.I love crossdressing and being treated like a lady.I have a nice big cock and I know how to wear sexyclothes really nice for you. I'm thinking about...

Big Tits, Looking for Real Fun in Chicago Big Tits, Seeks Fun Guy in the Chicago Area I can entertain you and make you laugh! I have a bubbly personality, big tits that love to be touched and I like to show off. I just like to kick back and have fun. I am light hearted and fun, intelligent and also street smart. Would like to meet similar...

INTERACTIVE MAP: Transexual Tracker in the Chicago Area! Local Transexual Hookups Meet local transexuals in the Chicago area. View our interactive map below to meet local trans hookup members who are seeking dating or sex hook ups. Click any thumbnail below to begin your search. Interactive Chicago Trans Hookups Map ...

I WANT TO CHEAT-ONLINE NOW 🟢 I'm tired of my husband. He just doesn't make me happy anymore. I really want to get out and see what kind of sneaky fun I can have. Do youlike the idea of us getting out together and not telling anyone? I know I do, I'm wet right now even just writing this. I want us to have som...