Post Ad My Account

Chicago, Illinois

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!

Home / Dating

>>>

<<<

January 24th, 2026
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...
Trans Flight Attendant Seeks Man for NSA... Hi I'm Annie, a 32 yr old t-girl, a Chicago trans flight attendant looking for someone who can understand my wild lifestyle and sometimes erratic hours. I work hard and I play hard. Let's wing it tonight baby! I love men, passion and exploring new things sexually. To say that I'm fetish friendly wou...
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...
HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Chicago! LET'S TAKE CARE OF THAT TRANNY FANTASY! "Experience your secret tranny desires in real life!"  Hot shemale Gia wants to hook up with you in Chicago!  No strings - just great times, so join my page free for instant access! Shemale Gia's Chicago Sexbook @ShemaleGia27 Photos: 42 V...
Fun Loving Couple in Chicago Seeks Male or Female for Threesomes... Swingers in Chicago Seeks Partner Hi, we are Jordan and Riley, a sort of a younger swinger couple in Chicago looking to explore threesomes with the right guy or girl who is open to sex with a man and a woman at the same time. We look forward to experimenting with some wild fantasies we have and wel...
ShopinRound38 outgoing, funny, and independent (Please only message me if you live within 50 miles of the Chicago area) . I am winding my career down and am wanting to traveling more and work less. Looking for someone to share intimacy and good times with. It’s getting harder and harder to find someone the old fashion way, so thought ...
No Strings in Chicago - Hot and Sultry, Looking for Affection Thanks for opening my ad. I've been neglected for far too long and am in need of affection. Things are complicated so no strings only please. That is likely to change at some point in the future. My hair goes down to my lower back and I have soft skin. My height is 5'8" and I am slender but curvy i...
Hey Sexy I'm Gonna Add YOU to My Cart! Shopping Hard in Chicago Hi there I'm Roseanne about 22 years, about 5'5 and brunette with big brown eyes here in Chicago. You know girls love to shop online and I'm no different. I'll just add you to my cart and check you out. Now how long until delivery? Huh? I don't do snail mail, so make it qui...
Looking for the bride of my dreams Chicago Contractor Seeks Wife This is Erik and I am a local resident and own a contracting business. I love distressed property rehab and I'm always looking for rehab projects. I am looking for a bright intelligent woman who can make me smile. When not working, I love the outdoors and I am an avid ...
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 ...
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...
INSTA ACCOUNT LOCKED 30 DAYS for TOS violations. Wanna Swap Pics Insta Account Locked for TOS Violations I guess they don't like nude pics anymore or maybe my pics are just too hot for Instagram. Don't worry, the show and free pictures are still going on. What's wrong with nudity and sex anyway All I want is to hear whether you like what I post or not. It helps ...
Nature Boy Seeks Hot Natural Man... I am Ira and love being out in nature when weather permits. I'm looking for a natural gay man (such as a bear or thug) who by his nature will take me and have his way without restraint. I'm a gay twink 22 years old and love to be ravished by force by a strong man. If you live in Chicago and fit this...
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...
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’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...
Looking for a Chicago MILF Who's Hot as Hell! Yo, all you hot mommas out there in Chicagoland. I'd really love to meet someone to hookup with on the regular - you know, FWB style. I'm Chris, 22 years old, 5'11, 180 pounds and stay in good shape. Young girls in my age bracket seem to be squirrely, unappreciative and awkward in bed. (my experienc...
Ohhh Yeah! I'm PHAT AS HELL BABY!!! BBW Wants FWB in Chicago LustyPhatty (Susan) here livin' large in Chicago. I know you are cravin' my curves and big playful funbags, and I got a few cravin's of my own. I want you to play with and massage my huge titties all night. (heaven) I'm a BBW 34, 5'3, 42EE cup, and will tell you the re...
Curvy Babe Needs a Naughty Massage in Chicago!... Can't afford a masseuse, and they don't exactly do what I really need anyways. I'm Brenda a 29 year old white female in Chicago w thick thighs and playful big tits that need a sexy man's touch. (sorry, only a man will do for this sort of thing) I work long hard hours, and at the end of my shift at t...
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...
Let's Play Cock, Paper, Scissors!... Gay Man Looking for Fun in Chicago Now that I got your attention. Hi I'm Graham, a gay man here in Chicago and I'm looking for a man who likes to play sexually charged games. I'm 28 years old, black hair, brown eyes, 6'0, well endowed, (8+inches) hispanic, single, love to party, no pets, ...
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,...
The One and Only - Chi-town's Own - Chocolate Delight Tonight! Get Some Ebony Sweetness C'mon now every lesbian woman loves Chocolate Delight! I'm decadent, sweet, petite and good enough to eat baby! I'm an English/Social Studies teacher here in Chicago and love what I do, but need my batteries recharged from time to time if you know what I mean.  I don'...
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...
January 23rd, 2026
Lonely Latina is New Here in Chicago Hola, soy nuevo en los Estados Unidos y estoy buscando el amor verdadero. Si estás solo como yo y quieres reunirte, por favor envíame un mensaje de texto y avísame. Maria28Chicago Hello, I am new to the United States and I am looking for true love. If you are lonely like me and...
VirginAss88, Never Been With a Man... I like having fun. I'm very honest perosn, very brave and interilligent. Love it here in Chicago and all the possibilities it offers for a guy like me. don't like the idea of bar pickups and would rather ease into this thing. Must be descreet and honest. Message me here. VirginAss88...
Black Female Seeks Sexy Couple in Chicago for Friends with Benefits Situation... Hey fellas, I'm Sheena, 29 years old and I'm a professional in Chicago who works long hours. I need a couple to take care of my needs and sex fantasies. When it gets urgent, it gets urgent - what can I say? I am a little picky and will not settle for just anyone. I need a couple who is sexually exc...
Need a Sex Buddy! After a long relationship I just want a sex buddy who is good with hooking up and being friends. I'm picky since I don't want to just hookup with any Tom, Dick or Harry. About me: Gay male, attractive, 31 years old, clothing purchaser, 5'10, blue eyes, well endowed, laid back, not much of a temper,...
Phat Booty Lesbian Soul Sister Shakin' it in Chicago Baby!... Hi I'm Lisa a Black BBW lesbian looking for a hot woman in Chicago. Hmm let's see do I want some chocolate, mocha or sweet vanilla tonight? I cant decide! Why don't you get hold of me and help me decide and show me what's up? I'm down for a hookup or maybe a girlfriend long term, we'll see. Please l...
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 ...
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 ...
Hot chick needs female distraction Will you be my much needed 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 y...
Help - Can't Afford a Masseuse in Chicago! Busy Girl Needs Body Rub in Chicago Mmmm... touch me baby! I'm DeeDee a waitress in a very busy restaurant here in Chicago. I work day shift when all the older crowd and construction workers come in and it's hard to meet guys my age. When I get off I'm soooo sore from carrying heavy trays and my fe...
Black T-girl Sub Bottom Wants Her Backdoor Man! Come on over baby! I'm Annie, an intense sexual t-girl living in Chicago who loves it doggy style and any way I can get it. I'm 29 years old, 5'9 in heels, tight as hell, horny as hell and pack a big surprise for my unsuspecting man. Let's spend the night together and make it last. If you need some ...
I am a hot black b#tch living and lusting in Chicago... Ebony Babe 4 NSA in Chicago Hi I'm Shayla here in Chicago checking this out online, never been at this before. Black female, 145, five foot 5, w extra large titties as you can see in my hot pics. (see more at my page) Just looking for a little NSA fun with the right sexy guy here in my area. I...
Shy 41 yr old guy Shy But Romantic in Chicago Hey ladies, I am Bryan, 41 and I am a little shy when it comes to meeting women. I am romantic and thoughtful and looking for a kind hearted woman. They tell me I'm handsome. I'll let you be the judge of that. what I do know is that I like to have fun and I'd love to mee...
Help - I'm a Nymphomaniac AND an Insomniac - There is Only One Cure! I'm sort of a reverse Sleeping Beauty story. lol I need lovin to put me to sleep and give me those feel good endorfins. I want to find a sexy man to hookup with when the need strikes me. Of course you can let me know when the need hits you too. This isn't a one way street after all. I'm 29 years old...
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 wanna be your friend and lover Mature black man in Chicago Howdy, my name is Samuel and I am a mature gentleman looking for a lady who is smart, funny and outgoing. I am 52, widower after 28 years, no kids. I am into riding my bike, the gym, and fishing on weekends. There is just one thing missing - maybe it's you! Do you like d...
Filipina Nurse Seeking Good Man for Fun and Romance... Hi I am Amihan just graduated from nursing school and now working in a major hospital here in Chicago. I am 23 years old, 5'3, 110 pounds, 36C, love people, love men and want to find a good man who wants a beautiful family someday. I don't think I want to date people in medicine. It's hard to explai...
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. Big, small or medium, it doesn't matter. I'm ready to spoil your body! Message me @JoanneBBWfem. Serious dates only please. Send y...
Sexy Honey I am a totally real, down to earth, fun girl! I am looking for open-minded, playful, sweet, tender, fun guy to make me laugh! SEXXXYHONEY Call or PM   Message me and send your recent pic for mine Talk on phone required first before meeting in person No strings...
I Need a Massage... I'm a Sucker For a Good Massage!... Hey any of you fellas in Chicagoland know how to give a girl a body rub? I need a slow long lasting massage by some stong sexy masculine hands. No quickies either! If things work out maybe we could have a mutual more long term thing? You know, a more steady get together? You scratch my back and rel...
Wanting slightly older gentleman Hello. My name is Sylvia, age 24 and I am pretty done with young guys who mess around. I want a guy who is mature and kind and likes to travel. Please contact me so I can learn more about you!  Send your recent pics for mine. I just took some naughty pics with my girlfriend Brianna. I think yo...
Fit Swinging Couple in Chicago, New to the Swingers Lifestyle & Ready to Explore! Swinging Couple in the Chicago, Illinois Area Hello sexy people! We are a swinging couple in the Chicago area. We are new to the swingers lifestyle but eager to learn and experience the passion! We assure we can give passion as well as we receive it! About Jeff Jeff is former military, stocky, fi...
King of your heart waiting for you in Chicago Abe, 32, local in the Chicago area, own my own business. I work hard and play hard. I am looking for a gentle guy who is understanding and kind. I love to laugh so you have to be funny, plz. Not all the time, but you need a good sense of humor. Life is too fun to be serious all the time. Message me ...
British T-girl Seeking Classy Gentleman in Chicago... I am Lacy, a white, blonde haired, trans woman, 30 years old, 5'9, 160 pounds, from Manchester, England and need a man who is educated, refined and handsome. I have just relocated to Chicago and am financially independent and looking for a gentleman who is like-minded, equally solvent and has except...
Sexy hung and big busted Hung and Busty Shemale in Chicago Tammy, 39, big tits!! Well hung, everything works, clean and so cute!! What more could you want in a gurl?!! How about you message me @Tammy39T and we can talk and meet! Send your recent pic for mine. Username: @Tammy39TLocation: Chicago, IllinoisAge: 39...
Single Black Female Seeks Sexy Man for Friends with Benefits Situation... Hey fellas, I'm Sheena, 29 years old and I'm a professional who works long hours. I need someone to take care of my needs sometimes at odd hours of the day. When it gets urgent, it gets urgent - what can I say? I am a little picky and will not settle for just any man. I need a man who is sexually e...
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 ...

>>>

<<<