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
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...
¿Hablas español? Hello good to meet you. Dulce amante esperando para probar su piel. ¿Puedes leer esto? ¿Hablas español? Quiero hablar contigo. Envíame un mensaje @DulceXAmante. I speak English, Spanish and some French. I want to meet you my sweet princess. Female or trans women only. No men.
Woman for woman in...
New to the Chicago area and lonesome! I am new here in this town and I would like to meet handsome gentleman to go to dinner and on date with. You are interested in me please send message to me. @RagazzaSexyX
Sono nuovo qui a Chicago
Sono nuovo qui in questa città e mi piacerebbe incontrare un bel gentiluomo per andar...
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...
27 Yr Old Columbian needs affection 27 Year Old Columbian Hottie
Have you got what it takes to please me? I have what it takes to please you, and I know it! If you are serious about being serious and you want love and affection I am the girl for you. View my pics and contact info @Alejandra27...
SciFi lovin' guy getting lonely in Chicago I love SciFi TV and movies. I am Will. I am 31, tall and muscular with light brown hair, grey eyes and tan skin. I work and I have a nice home and car. I never seem to have time to get out and mingle. I need a friend with benefits! Send me a private message to @WillSciFiFan if you want to swap ...
Love Giving Head!!! Hey all you hot men in Chicago! I'm OralAimie the best at giving mind-blowing head because I love it so much. But then who doesn't love it right? (if we're being honest) Lots of girls say they don't love it, but they are liars! There is nothing like it and every one is different. Long ones, fat...
Short and Sweet and New to the Area Hey guys! I will keep it short just like me! I am new in the Chicago area and I am single and looking for some dating fun! Send me a message @ShortnSweetKellie if you want to know more! ...
Blue Eyed BDE... Some say I should be in porn, but I have a profession that doesn't mesh with that, (EMT) plus I wouldn't want my future kids to ever see it. Hi ladies I'm Chad, 31 years old, not too serious, blonde hair, blue eyes, 6'0, 190 pounds, size 11" real uncut thick burrito type, I'm very oral both giving a...
Naughty but nice girl next door Naughty Girl Next Door
I want you! At least I want someone like you...I want love, and friendship and fun dates and mystery drives. Please don't be shy. Come and say hello! Send me a message @NaughtyGirlTrish69
I'm a naughty girl of many interests. Internet junkie, social mediaholic, pa...
Wife Swap! Let's Swing in Chicago Attention Swingers in Chicago!
Adventurous, attractive, athletic swinging couple in the Chicago area seeks swinger hookups for social activities and to explore the local swinging lifestyle. Let's go to the clubs and spend time socializing for fun and passionate sex. Kinks are welcome with us!
He i...
You want to date me, right? Man seeking Woman in Chicago
Hey, thanks for checking out my ad. I am Noel and I am here to let you know that you don't want to miss out on dating me. I am a joker and I love to laugh and make you laugh too. I am a music fan and I love going to live gigs. Who are your favorite musicians? I have ecl...
Hot Brunette Mature Woman Hot Brunette Woman in Chicago
Hi, I'm Angel. I'm seeking hot man who knows his way around the female body. I enjoy dinner, dancing and fun and frolics in the bed.
Send me a secure message! BrunetteAngel41XX...
Hey, any SteamPunkers out there in Chicago?... Hi, I'm Brad T. from Chicago born and raised. I love everything SteamPunk and am searching for a local woman who appreciates the romanticism of the late Victorian era. I'm 30 years old, love sci-fi, SteamPunk, conventions and events, travel and work. I have a dynamite job working with younger autist...
Shania Needs Some Sexy Masculine Energy in Chicago! Want a Real Man in Chicago!
Shania here and I'm looking for a certain type of energy to make me feel like a woman. I'm old school in many ways and love to be feminine and treated like a lady. But I'm a lady with needs like anyother and only you can satisfy those needs.
I live here in Chicago...
Karaoke queen loves singing with her Knight-ess Carmel Karaoke Queen in Chicago
You love to sing karaoke? Good!! Me too!! My name is Carmel and I adore singing. I am not shamed to say I am probably not so good but after a drink or two you probably won't care! I love singing modern pop, 60's and 70's disco, and even some modern rap. Message me wi...
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...
I'm the Girl Your Mother Warned You About!... Ok, but I'm not All bad! What? Just because I want some fun and sexy playtime riding the weenie? Well then just spank me already and give it to me hard and teach me a lesson I'll never forget! Punish me and pound me like you mean it. Is it hot in here, or is it just me? Your mother was right and I n...
Chill Dude Needs His BBW Queen... Hi ladies I'm Mike from here in Chicago, age 30, 6'0, 190 pounds, Italian, French, Norwegian mix, tatted, well endowed, muscular, journeyman plumber, who loves lots of curves and passion in his woman. I don't meet many women in my line of work and bar pickups are not usually the right way to find a ...
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...
Are You Hot for Teacher?... Hi, I'm Darlene a teacher here in the Chicago district. I'm 34 years old, teaching 4th grade for 10 years, 5'5, 130 pounds, 36C, blonde, blue eyes, divorced with no kids of my own, and lonely. Not ready for a serious relationship just yet, but more of a fun companion if you know what I mean.
Come s...
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...
Free Illinois Transexuals Guide Illinois Transexuals Guide
The Illinois Transexuals Guide was prepared by our trans experts at AmericanTransexuals.com. We bring trans women and admirers together for friendship, dating and sex hookups. View our free Illinois Transexuals Guide online.
Where to Meet Transexuals in Illi...
Girls on The Goth Side Get My Blood Pumping... Hi I'm Derek, 24 years old, 5'11, 180 pounds, black hair, hazel eyes, as it stands, I'm a bit anti-social. I have broad sexual tastes ranging from the vanilla to BDSM and enjoy fantasy play and trying new things. I need a dark Chicago girl who knows what the Goth scene is all about. Bloodsuckas...
A monster in the sheets, but a lady in the streets... Hello men, I'm Lilith a 27 year old sexy femme, fully functional, passible, sexy and hot to trot trans. I can be a bit racy and dirty when it's appropriate, but always maintain my poise in public. If you live in the Chicago area and are interested then drop me a line and introduce yourself. You can ...
Looking for Kinky, Fun, BDSM Sex at Random Times, Must be Discrete!... S&M for Sissys in Chicago
I am a gay male, bit of a thugish/bear into all sorts of BDSM, Fetish, Kink and some role play. I host and am seeking sissibois, twinks and queens for some extra sensual and painful fun. Your welcome, my pleasure! I have all the tools necessary in my Chicago dungeon to...
Wanna play 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 sure everyone is feeling it. You...
Sexy young lesbo wanting to date same Hi I'm Melodie! I am 19 and have been out to my family for 3 years. They are so cool and don't care as long as I am happy. My mom suggested I put an ad out online so here goes. Wait a minute... how does my mom know this site?!! hahah, anyway, here goes.
I am into clubbing but also like peace ...
Hot Italian Sugar Baby Wants to Live Her Best Life Now! Hello distinguished gentlemen of Chicago! I'm Alexis, full blooded Italian, 21 years old, 5'6, large boobs, 140 pounds a native of Aurora originally, but moved in to the city when I turned 18. I love the finer things in life and more mature men, so this works out for the both of us really. If you ar...- January 21st, 2026
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...
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 engra&cce...
Great kisser, looking for same Did I get your attention? If you are reading this, I must have! So, there is more to me that just great kissing, but I wanted a hook! Here goes...I am 32, a manager in a store and I just relocated to Chicago because of my job. I don't really know many people yet, except my roommates and I am kind of...
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...
Strict Shemale Dominatrix in Chicago - @DesireeTransDomme Powerful African-Queen Dominatrix in Chicago
I am full-time professional Domme Desiree. My Chicago area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you will learn to...
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...
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...
Minnie the Muff Diver... Chicago's Minnie Loves Oral
I'm Minnie a petite lesbian single girl living here in Chicago. Wanting to find a woman who is either lesbian, bisexual, or bi-curious for a steady hookup. Preferably a woman who loves oral since I love oral. (giving and recieving) I'm 21 years old, 4'11, 100 pounds wet;...
Mixed Race Male Seeks Sexy couple in Chicago... Hi there I'm James new to Chicago and I want to meet you. I've been divorced for about a year now. Not really wanting to dive in too deep just yet into anything serious, but you never know what will happen in the future. I need a sexy more mature couple from mid thirties to forties who can relate to...
Petite Chicago spinner girl for threesome... Little Bombshell in Chicago for Threeway
Hi ladies and gents I'm Jamie and I'm looking for a FWB situation with a hot couple who lives in the Chicago area. (willing to travel) As the title implies I am petite; only 5'1 and about 100 pounds. I am 22 years old, Italian, hot blooded and love to ride. ...
Amazing kisser looking for lips to practice on Lipstick Lesbian Loves Kissing
Do you love kissing? I do! I love it!! It is such a turn on! My favorite parts to kiss are my neck and my face and my lips and my whole body!
I am Kimberley, 22 and a part time waitress. I'm eager to meet you!! Send me a private message to @LipstickLesbianKim
User...
Latina Chica New in town New in Chicago age 28 Latina Chica just moved here. Wants to meet sexy chick for dating and fun. I've never done this before but new location, new me!! I would love some experienced woman to teach me how things work with lesbian and bisexual women. Don't worry, I am a fast learner and I already have...
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...
Alex's Huge Throbbing Cock in Chicago 💦💦 New to the scene, willing to try anything!
Thanks for checking my ad. I'm new to this. My name is Alex (hmu @AlexThrobbingCock4u) and I love fucking and getting my huge throbbing cock stroked and sucked to completion. I'm single but not totally out yet so please be discreet. At the same time, I'm a...
New to this place, Andrew, 36. Man Seeks Woman in Chicago
Ok, what do guys say on these things? I want to meet a kind, friendly and fun lady to hang out with and have fun with, and maybe more. I am tall and somewhat muscular build with dark brown hair and brown eyes. I enjoy my work as a business analyst. Want to know more? I'll...
Wanna touch my amazing?... Hi, LadyV living here in Chicago and I have need for a hot woman who appreciates my particular anatomy. I have a large butterfly and a BIG button if you know what I mean. I would love to have someone play with them all night and bring me again and again. My record in one session is 21 full O's, I am...
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...
Naughty & Nice Rubs... She's Naughty and I'm Nice! Chicago Massage Girls
Here in the Chicago area we have formed a team to please even the most demanding men of taste. We are Naughty and Nice or Carine and Inga. Sort of like the good cop/bad cop routine except we are here to make you feel good. We apperciate how life can wear on you guys and so we ...
29 Year old lady seeking secret rendezvous I am presently separated but I need to keep things discreet. If you don't mind, we should keep things secret and naughty. I like fantasy play and will try fetish stuff. I haven't put an ad on here before, but, hey, if you don't try, you never know! Send me a message! @Rendezvous29Chicago
Send me yo...
Erotic exotic Asian queen in Chicago now (25) Asian Transexual in Chicago
Stunning TS - Talia 25. Asian mixed race, non op, loves sex. Nice build with long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information. Classy in public but trashy in the bedroom. Versatile and attentive to your needs. Longte...
Intoxicating-Stacked Russian Blonde Beauty... I am a Russain woman coming to America soon I think, and hope someday to meet nice American man, and have beautiful American family. My name is Korina and I am living in Moscow. Maybe find good man in Chicago? I try different places for finding attractive and successful man in the USA, but not yet. ...