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 31st, 2026
Ebony Beauty Seeks Her Princess in Shining Armor in Chicago Ebony Beauty Seeks Chicago Princess in Shining Armor
My name is Cheryl and this is my first time ever posting a dating ad. You can't imagine how nervous I am putting myself out there! It's terrifying! lol.... but here goes.
I am medium height and build. I have great tits so if that's your thi...
Nascar fan looking for lady to have fun with Nascar Fan for Lady in Chicago
If you are looking for someone legit, hit me up for a date. I am a down to earth guy who likes to chill on weekends and do fun stuff. I enjoy dining out, concerts, live theater, strolls at the park, hiking, movies, sports and much more. I hope you have a good sense of...
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...
Chicago Paramedic Seeks Playmate, Friend, Lover 32 yr old, female, I'm a Chicago paramedic looking for someone who can understand a wild lifestyle and sometimes erratic hours. I work hard and I play hard. I love passion and exploring new things sexual, if you know what I mean! Kink friendly is putting it mildly. If you are interested in meeting u...
Italian single girl looking for love Ciao amore mio! Sono nel mercato per trovare un bell'uomo muscoloso e carino. Se sei carino e in forma mandami un testo per una data! (AngelicaXOXO)
Hello, my love! I am in the market for finding a handsome man who is muscular and cute. If you are cute and fit send me a text for a date! (Angel...
Italian sweetie looking to taste your fruit Woman seeking woman in Chicago
Amante dolce in attesa di assaggiare la vostra pelle. Riesci a leggerlo? Parli italiano? Voglio parlare con te. Inviami un messaggio @DolceAmante.
I speak English too! Sweet lover waiting to taste your skin. I want to talk with you. Send me a message @DolceAmante.
S...
Butch tomboy looking for beautiful femme Butch Tomboy for Femme in Chicago
My name is Toni and I am tall with short hair in a sort of spike and I work out regular. I love running and hiking and biking and photography. Dog lover, mom to 2 bulldogs, Smiley and Ranger. When I go out into nature I find myself at peace and I want a partner who...
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 ...
Jaw Dropping Hot Lesbian Hot Lesbian Seeking a Female Lover in Chicago
Did that get your attention? I hope so because I am looking for my perfect female partner. Someone fun attractive and intelligent. She should be easy to talk to, fun loving, laid back and attentive to her partner, just as I am. I'm looking forward to ha...
Anyone Here Interested in a Long Term Relationship? Hello, I'm Nora a lesbian living in Chicago my whole life. I'm 23 years old, 5'7, 130 pounds, athletic build, butch, dominant, love to party, loyal and don't really want hookups. Sex is important, but it's not my whole life. I want adventures and experiences and memories with the right woman of my c...
Lesbian Bombshell - Open Minded in Chicago W4W in Chicago
My name is Brooke, age 21 and I am lesbian, open minded and loving. Please message @Brooke4FemXXX with your recent photos for mine. Let's exchange info and meet up to see how things go.
Username: @Brooke4FemXXXLocation: Chicago, IllinoisAge: 21Gender: FemalePhotos: 36Vide...
Shy girl looking for first date Shy girl for lesbian hookup in Chicago
It is so hard to meet people at the moment and I am really wanting a date. No strings unless we hit if off. I am careful with socializing, so don't worry about me not being safe. I'm a lipstick lesbian femme, looking for fun chick to hang out with and see wher...
F/M seeking love and fun Female to Male Trans Man in Chicago
My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. This feels right and I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and oth...
Vivacious Redhead Bi-curious in Chicago... Hey ladies, I'm Bi-curious Lisa and new to this. I am excited and nervous at the same time. I want a hot encounter with another female to see what it's all about. Might have to take it slow at first, so please be patient with me. I am thinking a woman knows what a woman wants better than a man. I co...
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...
Having fun and Staying Young Young-ish trans fem looking for nice date with lady. I am kind and thoughtful and you will have a very good evening if I take you out. Let me know what you want to do or where you want to go. View profile @SherryTransFem33 and message me. Send your pics for mine. I'm hoping to find real chemistry an...
I'm Danish... Eat ME! Been dating most of my life and nothing too serious, but now I'm ready to settle down with the right person. I'm looking for a woman who will complement me. Where I have weaknesses she will have strengths. She must be local in or near Chicago, because I did a long distance relationship once and...
Sofia es Nueva en Chicago y sola Nueva en Chicago y sola
Nuevo en la ciudad y solo. Me gustaría conocer y salir con alguien que me plazca. Envíame un mensaje @SofíaSexy28
Mujeres solo por diversión o relación a largo plazo.
Username: @SofíaSexy28Location: Chicago, IllinoisAge:...
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...
Looking For My Lesbian Cosplaymate in Chicago... Im Bethany into cosplay, roleplay and women, but not necessarily in that order. I need a lesbian, bisexual or bi-curious cosplaymate in Chicago who likes the world of fantasy like I do. By day I'm a mild-mannered beautician, but when my alter ego comes out I'm your super hero, or sexy housemaid or a...
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 ...
Big 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...
Hung Black Male Chicago for male action Wants hot male for male sex in Chicago. All races welcome.
Want some hot male-on-male action? Well, look no further because DeAndre is here to satisfy all your dirty desires. Private message me @DeAndreXXX24. I love hot dates with hot guys, any race. Pretty much top because I prefer being in charge...
OLDER BABES for YOUNGER MEN!! Older Women for Younger Men
Sexy older babes show younger men how to truly please a woman!
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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...
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;...
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...
Totally new to this kind of thing! I use a couple of apps to do dating but I am never tried this site before. I am hoping I came to the right place. Are you my Mr. Right? I hope you are not my Mr. Wrong! My name is Lisette and I am 26 and single and I love to go to the beach and the movies. Check out my profile page and send me a mes...
Asian Beauty likes a nice massage My name is Aiko and I am from Japan. I like to meet a girl who likes massage to give and receive. I am attractive and sensual. I want to meet you. I am shy at first but very willing.
Please message me online for my photos and more information.
Kisses ๐
AikoFemme
Username: @Aik...
Love to Make Love! Grab hold of my big titties baby, spank me, and just do me already! I am here in Chicago scoping out this site looking to meet new people and have some NSA fun. Some of my interests include music, sports, and fashion. If you are interested and want to talk don't be afraid to approach me. Click ...
Genuine, yoga and jogging woman seeks limber man Woman Enjoys Yoga and Jogging, Seeks Man
I am Joy. I really am! It's my real name and I love meeting new people. I am currently single and looking for a real chill guy to hang with and have fun. Send me a Private Message! @ItsPureJoy31 Include your pics for mine. ...
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...
Young, Fun, Perfect body and 36DD looking for nice gent to date Young, Fun, Perfect Body and 36DD
26 yr old looking for fine looking man, with fit physique. Must enjoy sex! I like being active and enjoying life. I'm giving online dating another try.
My Pics and Contact Info 36DDblonde
Send your photos and mobile# for mine. Tell me a little about yourself...
Handsome, tall and tanned guy wants to meet shy woman Shy Guy for Shy Gal in Chicago
Male, 34 looking for gal, 26+ age. I'm a bit on the shy side so if you are also, that's a plus. I warm up once I start to feel comfortable. I have many interests and like new experiences. I want to meet a mature woman for fun, laughter and more. Check out my profile f...
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...
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...
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,...
Swingers Seek Sexy Man or Woman for Menage a Trois in Chicago How About a Threesome in Chicago?
Funloving couple in Chicago would love to meet open minded men and women for casual hookup. We are Dana (26 years old) and Rita (25 years old) and have just about one year in the swinger lifestyle and are having a blast. We have tried wife swapping and foursomes, b...
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 ...
Tall, Dark, Handsome Lesbian My name is Selena and I am tall, dark haired, in my 40s and still in my sexual prime! I have Latin heritage and I am fiery but kind. I do not have a bad temper but I am passionate. Age doesn't matter as much as personality and spirit. Any race, any height/weight. I love all body types as long as you...
๐ฅGay Hookups โ Bedroom Eyes & No Bullsh*t Vibes ๐๐ Your mama warned you about me yet your dad would secretly appreciate my nature ๐ 34, toned, tattooed, and nasty in the best way possible. I seek a genuine male partner who understands my body type through strong hand usage and dominant presence and filthy sexual thoughts.
Your ...
Sexy and Flirty Terina Ready to Play ๐ Chicagoย ๐ 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. ๐Swap Pics & HMU @terina61947 I ...
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๐ฅ๐ฅ๐ฅ WANT TO JOIN US IN SOME SWINGING SEX??? ๐ฅ๐ฅ๐ฅ Hey there, I'm Heidi from the beautiful Chicago. My husband and I are a fun-loving swinging couple who love exploring our fantasies with like-minded individuals. Swap Pics & Contact Info There's something so exhilarating about the swing lifestyle - the thrill of meeting new people, the exci...
I WANT TO CHEAT-ONLINE NOW ๐ข 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...
๐ณ๏ธโ๐Male for Male โ Letโs Skip the Small Talk & Get to the Moaning ๐๐๏ธ 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...
Dinner, Drinksโฆ and You in the Driverโs Seat? ๐ท๐๐ Chicago Hey there, lovely ladies of Chicago! My name is Baily and I'm on the lookout for that special someone to light up my world. ๐ซSwap pics & contact info I may not be a prince charming, but I can promise you plenty of laughs, good times, and maybe even a little bit of romance along the way. ...
CHICAGO - black๐crossdresser EBONY/BLACK CROSSDRESSER in Chicago Illinois ๐
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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...
๐บEbony Godess๐ฅTIME TO PLAY! I am affectionate, classy, mature, independent 420 friendly, Super Cute๐ Ebony Woman seeking. I love Kissing and Making out.๐น♦๐น Nice and Sloppy. I want a secret Fuck. I can host or come to your place thats your choice!Age & Size doesn't matter ๐๐๐My Profile and Pix Here ๏ฟฝ...
Tall & Peggable ๐๐ Looking for My Boss Babe Hi I am a Single 32 years old straight white male.I'm in Chicago and I would love to meet and amazing woman who wants to feel a real man! ๐ I love lots of foreplay, kissing , giving and receiving lots of orgasms. I am very oral i love to give as much as receive. I love to make her cum all ov...