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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- November 6th, 2026
Still unpacking but looking for a date New Girl in Chicago Looking to Date
My name is Charlene and I literally just moved here last week. I am barely unpacked yet and I am so wanting to get out and meet people! I love the movies and popcorn and music and dancing and having fun! Go ahead and hit me up for a date, or a drink or something!...
Hot Angel brand new to Chicago and web dating. Outdoorsy girl. I can be your hottest fishing buddy!
Ok, I guess I am doing this right and I am hoping someone sees this! I am 28 and want to meet a cool guy who likes outdoorsy activities like hiking and (unbelievably) fishing! Yes, I can even hook a worm! Want to meet and hang out with me?
...
Hey Swingers - Come Give Granny Some Sugar!... Try This Hot Granny For A Threesome!
Hi I'm Eva looking for a younger couple for a threesome in Chicago. As they say age is just a number and I'm a young at heart sexy granny still in her sexual prime. I'm Eva, 63, 5'5, 130 pounds, 36D cup, strawberry blonde hair, blue eyes and rarin' to go honey! ...
I'm as Pure as The Driven Slush!... Carmine here in Chicago looking for a fem lesbian who needs it rough and dirty. Imma spank that gurly girl and make you quiver with pain and delight. You'll cum in ways you never imagined! I'll get you home and your ass is mine! Don't play games with ME! You said yes when you walked through my front...
Fun Loving Couple in Chicago Seeks Female for Threesomes... Swingers in Chicago Seeks Female
Hi, we are Jordan and Riley, a sort of a younger swinger couple in Chicago looking to explore threesomes with the right 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 welcome any...
Englishman Without His Butler... It's a hard life for an Englishman not to have his butler in America, but I have learned to adjust. The really hard adjustment is not having a good woman and best friend. Moved here to Chicago about 3 years ago from London to work in the tech industry and do rather well despite the sky-high prices a...
Shiny blue eyes and 34 years old. Man for Woman Dating in Chicago
Hi, I am Brandon and I am 34. I am excited to meet a loyal and loving woman who can complete my world. If you would like to say hi, come and see my proflie and message m @BRANDON34M me for pics and contact info.
Username: @BRANDON34MLocation: Chicago, IllinoisAge: 3...
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 ...
Don't Worry I Bite! Feisty redhead trans in Chicago full of fun and loves it rough on the bottom. I'm 5'9, 170 pounds, 32 years old, well endowed, fully functional, passible and hot to trot. You can take me anywhere, but I can't promise to always behave. I have a dirty mind and when the urge hits it's hard to control m...
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...
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...
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...
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. Hit me up @SweetJasminT. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for a fun date and see where it goes! I'm preop and functional, very sex positive and love all sorts ...
FtM seeking Princess Bride in Chicago FtM seeking Woman in Chicago
Hi, I'm Andy, age 33, FtM mixed-race transgender man living in Chicago. Also, you must love that movie! If you don't get the reference you can still message me anyway! I love that movie and I will watch it with you over and again. View my pics and send me a message...
Married But Playing in Chicago Married Woman Playing in Chicago
Hey guys. My name is Jessica @Jexxica27, age 27. I'm married but playing around. He don't care. He said so and he cheated on me first so here I am. I just want to have a good time, no strings attached. Can you give me what I haven't had in a long time? I like i...
Sexy business owner wants to date sexy man Business owner for dating in Chicago
I am 43 and own a successful business. I am fully independent. I am looking for a sexy gentleman to date. He must be sexy, intelligent and solvent. Please private message me with a picture if you are interested in taking this further.
xoxo, Kim43fem...
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...
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, 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...
Chocolate D'Light Body Rubs in Chicago... Chicago's Black Lesbian Masseuse
Hi ladies I'm Lola an ebony masseuse in Chicago offering both erotic and theraputic body rubs for women. Just tell me which one you want, happy ending or not. I'll be pleased to go either way. I want you to be satisfied and come back for more. I host and have f...
Beautiful Krystale 25 Chicago visiting now Beautiful Preop Shemale Visiting Chicago
Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me @Krystale25shemale.
Krystale25shemale
Username: @Krystale25shemale
Age: 25
Location: Chicago, Illinois
Sex: MtF Trans
Seeking: Man
...
Young Female in Chicago is Curious... Chicago Bi-curious Babe
I'm Darlene, 26 living here in Chicago all my life and am finding myself bi-curious. I've always wondered what it must be like to be with a woman. I see women who are hot all the time and have certain sexual feelings for them, but I never acted on it. Except maybe a few time...
Chunky Monkey looking for Hunky Tomboy Chunky Monkey Fem for Hunky Tomboy
I am nice and curvy but not heavily overweight. I am looking for a chick who is handsome and butch but with some feminine qualities. Like it's ok if you cry at a movie! lol. I am 21, work full time and drive my own vehicle. I am looking for the right gal to make m...
Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Chicago
Hey! Thanks for looking at my ad. This is the first time I've done this so bear with me plz. I am Jared, FtM trans man. I transitioned at age 25 and I just turned 30. Come and meet me! Check my personal profile @FtMJared29 and say hi!&nb...
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: 44
V...
How do I look? / M4W in Chicago Man for Woman in Chicago
Check out my profile and tell me how I look. I am Sam. I'm a model, age 32 and told I am darn hot looking. Hit me up and check out my profile @SamChicago. Send your pics for mine. I'm available evenings and weekends.
Sorry guys, no men or couples. I appreci...
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. ...
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...
I'm a Steamroller Baby! Hi ladies, James here nice to meet you! Let's hop on my bike, put our knees to the breeze and do whatever the hell we please! I'm good with my hands, still a bit of an outlaw at heart, 35 years old, lived here most of my life, blonde hair, blue eyes, 6'1, around 220 pounds, muscular, love women, hug...
My name is Shey and I am a goddess of love Black Woman for Sex in Chicago
I am an African American with a hot body and a clear and quick mind. I want to meet a man who has a quick wit, an intelligent demeanor and a smart mouth. Go ahead and chat with me @EbonyQueenX to see if we hit it off....
Bored 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...
Bi-Curious Female in Chicago... I'm Cory, bi-curious, living here in Chicago, young, (23) about 5'7, about 140 pounds depending on the time of year, have perky tits, love sex and want to experiment. As a beginner I need to learn the rules and such. Please be patient cause I might be awkward at least at first. I am curious I think ...
Nice but Naughty 30 year old seeking affection and a good time I am half Latina and half European and have moved here recently. I am lonely, trying to assimilate and I would like to meet a very nice man who wants to play and enjoy life together. Text me for a date! (Naughty30luv)
I'm naughty but nice, love a good time, party friendly, have recent pics to share...
Jaw Dropping Hot Lesbian Desires to meet her Princess in Shining armor I am tall and light chocolate. I am elegant and slender with short afro hair. I look like a Bond Villain but I am truly very sweet. Why not give me a chance? I am also fun. Message me @MilkChocolateFemme if you like a taste of hot chocolate!
MilkChocolateFem in Chicago
Username: @MilkChocola...
Say BootyJuice Three Times and I'll Be There for a Threesome! Ebony Babe Wants Threesome in Chicago
Sataay here in Chicago lookin to freak it with a white swinging couple who need some hot chocolate. I will make an exception for mixed couples as long as one is white. It's a fantasy thing. I got big boobs, big booty and a big ol dirty mind! So come on by and s...
Lesbian Biker Babe Seeking Female Travel Companion in Chicago... I'm Brit - Hi! If you are like me then you love to ride and travel and experience life to the max. You have passion for the things you love, and you love a lot. You are high on life and can't get enough. You see the positive and don't have time for the negative. If this is you then I REALLY want to ...
Chicago Lipstick Lesbian, Hot 'n' Ready for Butch Woman Lipstick Lesbian for Butch Woman in Chicago
Lipstick lesbian wants to meet an awesome butch woman to share love and laughs. I am 25 and definitely femme. Long strawberry blonde hair, on the shorter side, fit and curves in the right places, but not overweight.
Come and Private send me a ...
Looking for the world's best playmate! Need: One good looking guy who can make me laugh
Also: has to like music and movies and be a gamer, not a player.
What you get: Me! My name is Patrice and I am 25, 5'6", curvy with dark hair with a blue streak straight down the back of my head, which I love! I am also a pretty good cook, so if we ...
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...
Down to earth mamma with dirty sense of humor Ok, so this is my first time doing this. Yeah I know, everyone has to have a first time, so here goes: My name is Sue and I love movies, food from around the world and traveling. I have only be living here in the Chicago area for 3 months and have not had a chance to meet many people yet. I want to ...
Calling all Swingers and Boobsters in Chicago Cali Needs Threesome in Chicago
Hi I'm Cali a single girl 24 years old with extra large boobs here in Chicago looking for the right kinky couple who will love'em. You might be boobsters if you know what motorboating is. You might be boobsters if you know more that 7 words for breasts. You might be ...
Late Night Wine & Trouble? 🍷😉 Looking for a Fun Guy Tonight Chicago Girlie Seeking Man or couple.. let's go have fun!
Sometimes nights can be so quiet. I'm 28yo girlie and love to live life, be fun, flirt and always be up for a laugh. I want chemistry, lots of fun, excitement and lots of conversation with playing involved. Love the initial spark and lust of...
Sexy and Flirty Terina Ready to Play 😘 Chicago 💋 Hey there, I'm Terina from Chicago.. I'm a playful and adventurous woman who loves exploring all kinds of fantasies. When it comes to sex, I enjoy trying out different positions like doggy style and cowgirl - the thrill of new experiences always gets me going. 😉Swap Pics & HMU @terina61947 I ...
Sweet Guy with a Naughty Side 😇➡️😈 Searching for My Queen Chicago Hey there, lovely ladies of Chicago! My name is Romeo and I'm on the hunt for my very own Juliet. Are you ready to be swept off your feet by a modern-day romantic? Look no further because I'm right here waiting for you. Swap pics & contact info ChicagoI may not have a balcony to profess my ...
😈😈 WANT TO HAVE GROUP SEX???? 😈😈 Howdy y'all! My name is LINDA, and my husband and I are a swinging couple based in Chicago.. We love the thrill and excitement of the swinging lifestyle - meeting new friends, exploring our fantasies, and indulging in all kinds of kinky play. 💋 Let's Have Some Group SexI am a playful and adventur...
💕🔥 Double the Trouble With Hailey & Jade What the poster wants you to know:
Take a break from the stress of everyday life… and come enjoy fun, flirtation, laughter, and unforgettable chemistry with two sexy women 😘✨
Hailey and Jade are two friends who are looking for someone to have a good time with. They're a brunette and a ...
Low-Key TS Sugar Baby 🌙 Soft Vibes, Selective Energy in Chicago I’m a TS sugar baby who keeps things calm, classy, and intentional. Evenings without noise, talks that flow naturally - these mean something to me. Confidence shows in stillness, not noise. Soft in manner, sharp in choices. Comfortable standing out, never trying too hard. 😌💄Let's Link Up...
CHICAGO GIRL NEEDS A HOT NIGHT OUT ❄️🔥🍷 I have spent too much time indoors so I need to experience some genuine fun by drinking and smoking while engaging in rough late-night activities 😈📸 I have pictures available for those who prove their authenticity and readiness.
I feel extremely sexual and I want to escape my current situatio...
Tattooed Sexy brunette, new in town & craving some fun 🔥Chicago 📍Chicago GIRLIE SEEKING MALE ATTENTION!!ABOUT ME: A 20-year-old brunette woman who has multiple tattoos across my sexy body... wanting to find someone in Chicago to spend time with a special someone while I'm in college. I'm currently studying to be a teacher.. I recently arrived here from ...
🎶 Concert Vibes & Bedside Rides - Chicago Cute Lesbian Girl in Chicago seeks her lovely playmate!! Oh beautiful 💖 I would love to meet at a local show, dance a little too close and make out in the parking lot like teenagers? In reply I'm 28, femme leaning switch and I like high energy chemistry. It's about time someone ...
💪🍆 I'm All Tha Chocolate You Could Need 💪🍆 Hey I'm new to dating sites but I'm ready to give it a try and see who might message me. I'm wanting to get out and have some fun. Yes I'm black and yes I have a thick 🍆 but I'm so much more than that. Also I want you to know that I love all shapes and sizes of men, I just want someone I can conn...