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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- December 1st, 2025
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 ...
Need My Big Phat Booty Princess... I love big butts and I cannot lie! I'm a red blooded black man, 29 years, 6'0, stays in shape, lives in Chicago and who loves him some bubble butts. More cushion for the pushin baby! If you are a woman living in Chicagoland with an exceptional sexy ass then don't hesitate to get hold of me and show ...
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 ...
Tiffany Shelle - Your Chicago Tranny Girlfriend! π Tranny Escort - Top/Bottom/GFE in Chicago
It’s Tiffany Shelle your perfect tranny girlfriend π₯° π SAFEπ π― LEGIT β¨π SKILLED, Exotic and Erotic π¦ π₯° I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!
I'm 100% functionin...
Fabulous Filipina woman wants wonderful man Filipina Woman Seeking Passionate Man
Hey guys, my name is Amina and I am full Filipina, just moved here to Chicago. I want to meet a kind and passionate man so please only message me if you are serious and fun and want pleasure! I am open minded. Hit me up @Amina4Passion to chat online and ar...
Young at Heart Grandma Seeking Fun and Adventure in Chicago... Hey boys I'm Doris, 63 yrs old, 40EE+, blue eyes, retired dispatcher from right here in the Chicago area. I've decided to put away the knitting needles and gardening tools and craft supplies to have some real fun! I need a sexy man who knows what a woman really wants ;) The best feature about me is ...
Busty chocolate Beauty loves milk chocolate treats Busty Chocolate Bunny in Chicago
Hey gals, I am Bunny and I am dark chocolate in complexion and big busted. I am a foodie and I love all foods! I watch all kinds of food shows from all over the world! Hit me up @BustyBunnyXXX
Hope to speak to a food/dining loving lady soon!
Username: @...
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...
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 ...
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...
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...
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 BDSM Master Taking on New Trans Slaves... I am single minded strict, controlling discipline oriented Master in the Chicago area seeking a devoted sub/slave to satisfy all of my whims. I will break you in with proper training protocols starting with, corporal punishment, all kinds of Humiliation, hucow, whips, gags, eletro, medical and much ...
Independent Woman in early 40's seeking independent guy Independent Woman 40's for Man in Chicago
I am in my early 40's and I am looking for a cheeky, intelligent man who can make me laugh. He should be in reasonably good physical condition and have a job. Contact me @LizzieBethK if you think you fit this description and we can arrange a date. Chic...
I will never ghost you! I’m Tommy age 37 and am sort of a home body. But, I still like going out for dinners, drinks, movies and having fun now and then. I live in Chicago and my hobbies are: writing music and poetry, spontaneous trips, and playing my piano. I work in tech, so in this crazy world, let’s be craz...
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...
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...
Hot trans chick with nice boobs Hot trans chick in Chicago. Sheila wants to meet you. Hey guys, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, well endowed and functional, top or bottom. I love oral sex giving, receiving or 69. Want to explore kinks? Me too!! Want to...
Iβm 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...
Your den or mine? Chicago cougar looking for wild young cubs to tame! I'm a more mature woman in search of a younger man for NSA companionship in Chicago. My name is Nora, 5'5, brunette, blue eyes, large breasted, insatiable in appetite and need a man with stamina and drive to get me off. If you are under 30 years old and over 20 then let's talk and see where things l...
I'm a Chubby Chaser in Search of My BBW Queen... I'm Charles a black man about 6'0, 200 pounds, in good shape, 27 years old, in college and am an admirer of large women. I'm open to any race and any size be it BBW or SSBBW. I love a phat booty and big boobs. If you live in Chicago and have large assets then I'm your man!
Hoping for more than a ho...
Sex and Smokin' Leather... Hi Leona here in Chicago (originally from Rochester, NY) and am looking for a sexy man who smokes and loves sex. Or at least a man who doesn't mind smoking and sex. I wear a lot of leather gear and smoke obviously and have a dirty mind to go with it all. I moved here and work at the Chicago airport ...
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, ...
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...
Quirky Fun Loving Lesbian Couple in Chicago... Lesbian Couple Seeks Equal Partner
Hi out there in Chicago we are Tori and Joni a lesbian couple looking for a third to join us for some sexy fun and antics. This is a proposal for a long term relationship with an open minded couple who can't resist the idea of bringing in another woman for extra f...
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...
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...
Mixed Race Male Seeks Sexy Shemale for FWB in Chicago... Hi there all you hot trans ladies 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, but you never know what will happen in the future. I need a sexy more mature woman who can relate to me in terms of life experi...
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...
Looking for a Smooth Operator in Chicago... Let's See How You Operate!
Hi all I'm Arlene a busy surgical nurse here in Chicago looking for a guy who is smooth like Southern Comfort. Not brash and overly cocky and overly sure of himself. I need that silent strong masculine energy in my life that tells me I'm a woman and makes me glad to be so...
Are You Uber Horny? I AM - Maybe We Can Work This Whole Thing Out Together!... Nympho Seeking NSA in Chicago
I am Tory, a 24 year old, brunette living in the Chicago area, 5'5, medium build, told that I'm fun, easy to be around, a good conversationalist and have a sexy relaxed vibe. Do you live here locally, find me attractive and love big playful titties? Then I might b...
Attractive 48 yr old seeking younger man in Chicago for fun and excitement Older Woman (age 48) for Younger Man in Chicago Area
Thanks for looking at my ad. I am willing to travel for the right guy but I prefer within 25-50 miles of the Chicago area. I am blonde (Yes, natural!) and I am cute, with a small frame and long legs. I love music and dancing and sex! Hit me up wi...
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...
Not exactly out yet. Need discreet NSA... Mixed mexican/white male 29yrs, professional divorced with two kids. I am looking to explore my bi-sexual curiousity in the Chicago area with the right man and see if there is anything there. If you can be discreet and are interested then please come see me by clicking here....- November 30th, 2025
Sexy Asian Girl Sayo for American Guy in Chicago Hello. I am Sayo. I am a hot and sexy Asian girl. I would like to meet an American guy for relationship and dating. I am a great cook so why not get your appetite up and come for dinner? I give good massages and like romance. Send me your pictures for mine also. Message me @SayoYung to chat or for a...
Super Barbie T-Girl Wants Hot Men in Chicago... Hey sexy boys, I'm a trans woman looking for a man, forget about my intelligence, talent and great personality, I have something better to spring on you when the time is right. I aim to show you the time of your life and ride the weenie all night! Honestly I'm so horny I could do hand, oral, top or ...
Hello guys, looking for a boy friend So, my name is Talia from the Chicago area and I am completely new to this online hookup stuff. I have never put an ad in a website before so I hope I am doing this right! If you would like to speak with me or arrange a date you can check out my profile @Talia4bf here and let's swap some sexy p...
Join Me in This Carnival of Doom... I'm Joann a goth white female living in Chicago and single. If you are alone like me then join me as the whole world continues to sink into the dark abyss. We will embrace it's negative energies together. If you live in Chicago then contact me here and let's connect before the hour grows too late. -...
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,...
Divorcee looking for exclusive arrangement with generous gentleman Divorcee Seeks Exclusive Arrangement with Sugar Daddy
Hi, I'm a recent divorcee seeking an exclusive arrangement with a Chicago sugar daddy! I am am 26 years old, love sex and pleasing my partner. I am looking for someone open to all types of fun and adventure! I'm classy enough to take to a busine...
π³οΈβπMale for Male β Letβs Skip the Small Talk & Get to the Moaning πποΈ We should avoid pretending about our friendship intentions because I am looking for something more. As a 30-year-old man with a fit body I understand my desires which include a dominant confident partner who takes control without hesitation. View My Sexy Gay Profile -
We will hav...
πPARTY & SEXXπ So I really need someone to take me out and show me the ropes. I do want to have some fun and let loose. Will you help me celebrate? πΈ My Pictures - I hope you like what you see. If you do let's meet up and have some sexy fun!
HOT GIRL NEEDS OUT ππ₯³ Let's drink, party and hookup&n...
π Windy City. Wild Nights. TS Tina is Waiting πβοΈ Hey sexy… I’m Tina, your thick & tempting TS babe right here in Chicago, and I’m ready to turn up the heat on your cold night π Whether you’re looking for soft touches, deep pleasure, or just a naughty escape — I’ve got you covered. ( View My Sexy Profile ...
Chivalry Isnβt DeadβBut I Might Be After One Good Ride ππ an looking for a hot woman to be my eye candy and trophy woman. Let me pamper you and take you out. I love lots of foreplay, kissing , giving and receiving lots of orgasms. I am very into oral and eating that kitty. I'm a damn good lover and know how to use my cock! I want us both to use each o...
πΆοΈMale Seeking Male β βWhat Are You Into?β Everything. Now Come Over. ππ€ You have me as your hidden secret while I am your deepest sexual desire which will cause you to have morning soreness and a pleased expression π I enjoy oral fixation while practicing roleplay and light dom/sub games with an interest in power dynamics and extended filthy nights ...
π Looking for my Queen of Hearts π Chicago Hey there, lovely ladies of Chicago! My name is Maury and I am on the hunt for that special someone who can make my heart skip a beat. π You can find me in the dating profiles at Swap pics & contact info , so don't be shy to reach out and say hello!
I'm a hopeless romantic at heart...
2 ASAINSππbj/gfe/rubs Do you want to feel the soft touch and body of a hot and petite ASIAN girl?? How about two asian ladies, who know how to make you feel good in all the right places.. Let them rub, kiss and lick you. All over your body, check them out here, we're waiting.
β€οΈ My Profile - Learn more about me.
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π Sweet, Seductive & Craving Her β Ebony Babe Looking for a Good Time π Chicago Ebony Lesbian Lover Seeking Woman!!π I am a thick, chocolate colour ππ€ , in my mid-20s, with soft curves and smooth skin, and a wicked little smile. I am playful, affectionate and very into women, especially if they know how to tease and please. It should be ...
MASSAGE/BJ/NURU - VERIFIEDβ
I'm JENNY LOVE β€οΈ, an exotic & rare bombshell that is the perfect mixture of sweet and sassy. I have stunning long legs, soft glowing skin & seductively mesmerizing eyes. You will love my petite body and nice smooth skin. Let me Massage you and make you cum! πIf yo...
I'LL DO ANYTHING YOU WANT ME TO...πππ Hey babe, I'm Julie and I'm new here. I need a fun man to have some naughty fun with. I love to π PARTY π.. maybe drink and more π Then while we're having fun partying, we should fuck and fantasize. I love dressing up ππ I love pretending to be whatever you want me to be. I want us to...