Chicago, Illinois Sex Ads and Adult Classifieds

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  • June 16th, 2025
  • Looking for My Chicago Cosplay Queen...Looking for My Chicago Cosplay Queen... By day I'm a 29 year old mild mannered architect, but I can transform into a super hero master of the Universe. Together we will vanquish cosmic villans and travel to conventions, and enter contests and such. It's sort of addicting and a lot of fun. The best part is meeting the people. I'm very soci...
  • June 15th, 2025
  • Wife Swap in Chicago Anyone?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 ...
  • Bored and lonely blonde barbie dollBored and lonely blonde barbie doll Bored Blonde Swap Pics and Numbers I am bored and lonely and I want to meet someone who is funny and kind and really clever. I am no dumb blonde so I will give you a run for your money. Come and meet me (BlondeBarbieDoll) on my personal profile page with pics and my contact info. Let's have s...
  • I Need a Massage... II 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...
  • hippy_nomad Loves antiques, rescuing stray animals, 420...hippy_nomad Loves antiques, rescuing stray animals, 420... Must be 420 friendly. Currently living in Chicago I am an honest, hardworking and caring woman who is looking for the same. Let’s face it we’re not getting any younger so who wants to play games- NOT ME! I also like going to flea markets, dancing and most of all vacationing! So if you th...
  • Need Insane Orgasms!Need Insane Orgasms! I got a big sensitive love button if you know what I mean. Hi Shaylah here in Chicago with a problem and the only cure to that problem is having multiple insane and intense orgasms. I'm a screamer and a squirter so be warned. The intense multiple orgasms help me to keep calm during the day. Otherwis...
  • πŸ˜‡ πŸ† 😍TRANNY COUPLE -Chicago- SHEMALE SWINGERSπŸ˜‡ πŸ† πŸ˜πŸ˜‡ πŸ† 😍TRANNY COUPLE -Chicago- SHEMALE SWINGERSπŸ˜‡ πŸ† 😍 Hey babe, are you interested in Shemale or Transsexual Sex? How about a shemale couple looking for you to join? If you want to have some sex and swing with us.. You MUST be willing to do whatever we say. Do you want to play with our cocks and boobies at the same time?. Swap TS Nudes & Conta...
  • Jon Boy seeking Chicago Top Male to Pleasure πŸ‘…πŸ†πŸ’¦Jon Boy seeking Chicago Top Male to Pleasure πŸ‘…πŸ†πŸ’¦ 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...
  • CHICAGO - blackπŸ†crossdresser CHICAGO - blackπŸ†crossdresser  EBONY/BLACK CROSSDRESSER  in Chicago Illinois  πŸ‘…πŸ˜‰πŸ†  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...
  • Open Minded Woman seeking Open Minded ManOpen Minded Woman seeking Open Minded Man When I say open minded, I mean in every aspect. I like a mass debate ;-) and I enjoy a good intelligent conversation. I like uninhibited romance and sex!! I am looking for same in a partner. If you enjoy giving great sex just as much as you enjoy receiving, we might be a great match!  Let's sw...
  • Artzee Fartzee in Chicago Here for Men and Inspiration!...Artzee Fartzee in Chicago Here for Men and Inspiration!... I'm, Art, (or Arthur) 25 years old, 5'8, 160 pounds, black hair, hazel eyes don't get out much because I'm so into my art, but I'm here to maybe find some inspiration. You never know where it will come from. Could be mind blowing sex with a hot just out gay man. Mmmmm! Bring it on, and hit me like y...
  • Femme looking for FemmeFemme looking for Femme Femme for Femme in Chicago Hi, thanks for looking at my ad. My name is Kari. I'm femme, looking for femme. I love make-up and dresses and I want to share my world with a hot chick who likes the same. I recently upgraded my car, so let's go for a ride! I am currently studying dentistry and work two...
  • I WANT TO CHEAT-ONLINE NOW 🟒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...
  • Filipina Nurse Seeking Good Man for Fun and Romance...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...
  • FEELING H0RNY? IFEELING H0RNY? I'm Your Dirty Little Secret 😈 CAM SEX BUDDY! πŸ‘οΈβ€πŸ—¨οΈπŸ’¦ I'm horny and bored 😈 so I set up my sex cam πŸ‘οΈ‍πŸ—¨οΈπŸ’¦ I specialize in kinky fetishes. Seriously, I like vanilla sex but I also like to taste all the flavors too! 😈 Join my cam (online now) and tell me your kinky secrets and deepest sexual desires and I'll share mine with you. T...
  • Do you know the difference between a dick and a bucket of popcorn?Do you know the difference between a dick and a bucket of popcorn? You don't know? Well then take me to the movies baby! Mmmm think of all that creamy, buttery, salty goodness! Talk about a double feature. lol Hope you have the munchies for this hot Chicago tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer than...
  • RATE MY PICS XXX  LetRATE MY PICS XXX Let's Swap Pics and Sext Online! Let's Swap X-Rated Pics Online I wanna play a game. Here it is: I really just wanna send you my dirty pics. I love it when men get off to me and all I want in return is a rate of my pics and how good your orgasm is. Wanna play Look me up: RateMyPicsX  It's free and I do reply to fre...
  • Twisted Sister - Loves to Ride.... and be Ridden!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...
  • YOUNGER COUPLE ( 18+) LOOKING 4 SOME EXTRA FUN πŸ”₯πŸ₯΅πŸ˜‰YOUNGER COUPLE ( 18+) LOOKING 4 SOME EXTRA FUN πŸ”₯πŸ₯΅πŸ˜‰ Hey there, I'm CONNIE from Chicago. My hubby and I are a swinging couple who love to explore our sickest fantasies.. Do you want to hear more about what we're down to do? I want to make love with like minded individuals and fuck hard!! The thrill of wife swaps, threesomes, and the swing lifestyle tu...
  • Black Female Seeks Sexy Couple in Chicago for Friends with Benefits Situation...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...
  • DONDON'T MASTURBATE ALONE! Let Me Get You Off! LET'S GO CAM-TO-CAM! Don't Masturbate Alone... Get Off With Me! Want to chat live cam to cam before you hook up? Talk about anything. Share your wildest fantasy! Ask me anything. Me and my girlfriends are home alone and we enjoy getting naughty on cam. Join My Cam Free! Avai...
  • Fit Swinging Couple in Chicago, New to the Swingers Lifestyle & Ready to Explore!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...
  • Widower seeking affection in ChicagoWidower 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...
  • Lookin for the big one?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...
  • I just want to enjoy life and practice safe sexI 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...
  • Single White Trans Woman Wants FWB in the Windy City..Single White Trans Woman Wants FWB in the Windy City.. I'm Hora looking for love in all the wrong places and lovin' every second of it! So here I am single and on this site looking for a sexy man to take me to loveland on a regular basis. (NSA) I expect you to be: not afraid to party, not afraid to go top, not afraid to go bottom, not afraid to take me ...
  • Naughty boys check me out... good thing I LOVE naughty boys!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...
  • New to this place, Andrew, 36.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...
  • My body yearns to be the center of your attention...My body yearns to be the center of your attention... Hi all you sexy men out there in Chi-town! I'm a horny White female looking for NSA sexual encounters of the lingering and passionate kind. I don't want just wham-bam thank you m'am type hookups. I want you to worship my body like you mean it and pamper me. Fix your studying gaze upon me when I'm na...
  • Email Chicago Shemales Now! πŸ’ŒEmail Chicago Shemales Now! πŸ’Œ Want to Hookup and Find Chicago Shemales? RADE PIX - MESSAGE - BROWSE PROFILES This Website Helps you find local shemales and TGirls meet local men. It's the perfect place to find what you're interested in πŸ˜‰.. Do you want to meet local shemales who want to fuck and have some sexy fun? I dar...
  • Hello! My name is Alexis in ChicagoHello! My name is Alexis in Chicago Sex Hookup in Chicago If you are looking for someone to entertain you and be your ultimate fantasy girl, that is me. I am hot and sexy and want to hook up with someone with warm feelings and a bright personality.  Send your pic for mine.  AlexisXoXoXo If this ad is online then I'm availa...
  • Roses are Red, Violets are BOOBS!Roses are Red, Violets are BOOBS! Woman Seeking Boob Man in Chicago I'm Violet! Just a girl living here in Chicago all my life except for a short time in Tucson, AZ. I'm 23 years old, big natural titties, redish hair, blue eyes, big sexual appetite and love to have a man treat me to a long blissful booby rub. That gets me hot ...
  • Big Tits, Looking for Real Fun in ChicagoBig 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...
  • Superb Shemale in Chicago...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 ...
  • Czech Beauty new in ChicagoCzech Beauty new in Chicago Ahoj, lásko. Rád bych se s vámi setkal a hledal jsem vás. Kdy se s tebou m?ΕΎu setkat? Jsi tam venku? Kontaktujte m?. Hello, my love. I know you are out there somewhere. I would like to meet you and have been looking for you.  I like texting and sharing sexy thought...
  • Great kisser, looking for sameGreat 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...
  • Here I am! Hookup with a smoking hot grandma in Chicago!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...
  • Inviting eyes and seductive thighs wanting to find loving guy in ChicagoInviting 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, I guess not so here I am again.  I recently moved, so I am new in Chicago and have no local friends to hang out with. I would love to meet fun, down to earth guy to explore passion and hot sex. I just need to have some fun an...
  • Simple FunSimple Fun FREE Sex Finder Service! We get you LAID, gaurunteed. We do all the hard work for you. Getting laid has never been easier. This Is How It Works: 1. You enter your email. 2. You get a FREE list of women in Chicago who are "down to fuck" right now. 3. You contact these horny women and get laid to...
  • Ebony sister in need of bullEbony sister in need of bull Hot ass ebony chick looking for a big dick to fill me up. I'm a three-hole slut; I love dick. Contact my profile and get me off. I need your dick like yesterday. I haven't got off in weeks. Help me link up, and have a fun time. I'll let you do anything you want. I have not found anything that I don'...
  • BDSM Master Taking on New Female Slaves...BDSM Master Taking on New Female Slaves... I am single minded strict, controlling discipline oriented Master in Chicago 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 more...
  • Hot Girl Wants To Hang Out With Woman in ChicagoHot Girl Wants To Hang Out With Woman in Chicago Are you cute and fun? I'm lonely and looking for good times with someone special. Just send me a message @HotGirl4XXXFun and I will send my recent pictures. πŸ”₯ Please send your pics and contact number. Let's text and go from there. Local fem girl looking for local female friend (butch or fem) to ...
  • Just Got a Delivery of Kinky New Toys!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...
  • Any Irishmen Here in Chicago?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 ...
  • Black T-girl Sub Bottom Wants Her Backdoor Man!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 ...
  • Lesbians in Chicago Message Me πŸ˜»πŸ’¦πŸ‘…Lesbians in Chicago Message Me πŸ˜»πŸ’¦πŸ‘… (W4W) Ladies whowant lesbian sex NO MEN Please.. Looking for a sexy lady to play with tonight, W4W Women only please, I'm strickly lesbian. I love pussy. i'm local and ready to play.. So if you're a lady who wants to play with another sexy lady, hit me up.  ...
  • 🏩🏩🏩 Sexy Sluts Looking For Discreet NSA In Chicago 🏩🏩🏩🏩🏩🏩 Sexy Sluts Looking For Discreet NSA In Chicago 🏩🏩🏩 FREE Sex Finder Service! We get you LAID, gaurunteed. We do all the hard work for you. Getting laid has never been easier. This Is How It Works: 1. You enter your email. 2. You get a FREE list of women in Chicago who are "down to fuck" right now. 3. You contact these horny women and get laid to...
  • My Husband and I are Into Cuckhold and Need a Bull in Chicago...My Husband and I are Into Cuckhold and Need a Bull in Chicago... We are professionals here in Chicago and are looking for a man who can rise to the occasion and fill me up while hubby watches from another adjoining room. We are easy-going and discreet and need you to be also. We should necessarily meet first to discuss some things and get to know each other first...
  • Fun Loving Couple in Chicago Seeks Male or Female for Threesomes...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...
  • Searching for My Sexy Care Free Biker Babe!...Searching for My Sexy Care Free Biker Babe!... Hi ladies I'm Tommy from right here in Chicago born and raised. I'm 32 years old, 6'1, 200 pounds, dark hair, blue eyes, Fire Department/EMT, take good care of myself, but do love to party once in a while. I'm a pretty good cook I'm told by the guys, so if you're not no biggie.  I get quite a ...