Chicago Men Seeking Women Sex Ads

Browse Chicago men seeking women sex ads and adult classifieds to find local men for dating or sex hookups. Contact any of these men to swap pics and contact info. Chat online or text and arrange real-time sex hookups if you feel a connection. It's free to search all men for women classifieds, or post your own adult ad!

Home / Dating / Men > Women

>>>

December 5th, 2025
Daniel 28, Plumber, recently new to area 28 y/o Man New to the Chicago Area For Dating I am fairly a plumber by trade. I am looking for new people to meet in the Chicago area and I would love to meet a nice lady I can talk to and listen to and maybe more. What do you enjoy doing? I like trying new things so don't be shy. I like camping, d...
Sugar Magnet Looking for His Sugarbaby in Chicago... Hi, I'm Matthew a semi-retired Real estate developer recently divorced seeking my sugarbaby for sexy good times and companionship. I have a yacht, penthouse and nice cars, but still something BIG is missing... YOU! I admit, I'm not the best looking guy, but you could do worse. Do you like to travel?...
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...
George, 31, long beard to tickle you with Bearded Man for Non-Bearded Lady in Chicago Hey ladies, I am George and I am 31. I have been growing my beard for 3 years and it is nice and long. If you like bearded dude let me know and send me a private message @BeardedGeorge. I'm fun loving, athletic, Alpha type guy, comfortable in my skin, ass...
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 ...
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...
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...
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...
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 ...
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...
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...
exciting black guy waiting for you Exciting black guy in Chicago I am Herman. I am an active and fit, age 32, black male and I am excited to meet you! Looking for lovely lady of any age but not too young to understand my humor and not too old to keep up ;) I am fit and fast to run with and muscular. Tall and attractive. Want to work...
🌟 Handsome JOHN Seeking a Spark 🌟 LET'S PLAY SOME Hello there, lovely ladies of Chicago! My name is Johann and I am on the lookout for that special someone who can ignite a fire in my heart. 💖Swap pics & contact info I have a passion for exploring the great outdoors, whether it's hiking through the mountains or relaxing by the lake. �...
Playful Cub Searching for Cougar in Chicago... I love mature women and appreciate the skills they've developed over the years. I'm Dana 22 years old, have my own car and apartment and good job, so I'm not looking for a sugar momma situation. I just want a sexy cougar to play with and get to know even if it's for a short time. I would be so grate...
Let’s Flip the Script—You Lead, I’ll Moan 😍🎀Chicago Hey there, lovely ladies of Chicago, My name is Wells and I'm on the hunt for someone special to explore this beautiful town with. 💫Swap pics & contact info  I'm a thrill-seeker at heart, always on the lookout for my next adventure. Whether it's hitting the slopes together or enjoyi...
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 ...
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...
Cunning Linguist... Oral Expert Seeks Woman in Chicago Hi, I'm Calvin a single male in Chicago looking for a single woman who is funloving and passionate. I am orally gifted and speak fluent English and have an accent. My greatest oral talent however is in my long tongue - my whiskers are soft and tickly, but not...
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...
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...
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...
Tom, 42, wants single minded woman Hello ladies, I am Tom, age 42 in Chicago. I have a good job, a new truck and I own my house. Life is pretty good and I'm ready to take the next step toward finding love. Could you be who I'm looking for? We'll never know unless you message me.  I am not looking for someone who is going to giv...
Click here - Add to Cart. Chicago Single Dad for Fun That's my mom in the pic with me BTW. I'm Jonah here in Chicago a single working dad age 31 with a three legged cat and hope to find a woman for some NSA fun who has a big purse to get lots of snacks into the movie theatres. I'm not afraid to talk about Bruno, or yell Yab...
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...
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 ...
I wanna be your friend and lover Mature black man in Chicago Howdy, my name is Samuel and I am a mature gentleman looking for a lady who is smart, funny and outgoing. I am 52, widower after 28 years, no kids. I am into riding my bike, the gym, and fishing on weekends. There is just one thing missing - maybe it's you! Do you like d...
Let's Get it Out of Our System... Henry in Chicago looking for nsa with a woman around my age. (25 yrs) I'm a fun and sexy sort of guy who is looking for the same in a girl who is local. If you get the need I can help when it gets urgent, and vis-versa. Hopefully this will turn into an on going thing for us. Don't really want a full...
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...
December 4th, 2025
I want to worship your sexy sweet feet... I'm a passionate Italian man looking for sexy feet to pamper in Chicago. Just the sight of a pair of angel feet leaves me breathless. I can't even go near a beach for the over-stimulation it brings. I do like it in the spring when women start wearing strapped sandals though because it usually leaves...
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...
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...
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...
Exotic and Erotic Orlando From Tuscany Italy... For More Than Just a Hookup Ladies I am Orlando visiting in Chicago. Let me take you on an erotic journey of passion and delight tonight. I know how to treat a woman and bring out the sensual romantic in you. Just let yourself go and forget all about your cares for the evening. You will be in good ...
Chicago - Let’s Make Some Mischief… And Maybe a Mess 😉  Hey gorgeous 😏 I’m a 35-year-old guy from Chicago with a cheeky smile, strong  hands, and an even stronger craving for adventure — both in and out of bed. My intention is  to meet a woman who possesses confidence because I seek someone to flirt with and share laughter ...
PeeWee's Looking for a BIG Adventure! Hi, I'm Herman, and me and my little friend are looking for some excitement in Chicago tonight. If you are up for an adventure we are too! We aren't too picky, just hope you like Tequila and dancing. Please be motherly and kind. Can you come out and play?. If so click here to come out and see u...
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...
December 3rd, 2025
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...
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...
Widower 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...
Chicago's Sex Ninja Has Come to Your Rescue... Single Guy 4 FWB in Chicago Hi I'm Carl, and maybe the part about being a ninja isn't quite true, but I do have a yellow belt in Karate or was it Judo? Anyhow, I'm living in Chicago and am looking for something more long term with the right lady. Me, I'm a black male, 31 years old, 5'10, 180 p...
Looking for a 420 Friendly Girl Tonight... Come on over and smoke my blunt baby! This will be an NSA boobies for doobies exchange. If things go right we could be steady smoke buds. I got the weed if you got the need. I'm Mario a Latino man, 25 years old, great shape, love the bud and women. This works out for the both of us. If you're jonesi...
Ken, 42, lonely for you Male for Female Chicago Hi there! My name is Ken and I am 42 and looking for a real nice woman in the Chicago area. Send me a message and check my profile @Ken42seeksWoman for my recent pictures and contact info. Let me know about you. I enjoy skiing, hiking, boating, travel, gaming and reading. Ac...
Looking for the bride of my dreams Chicago Contractor Seeks Wife This is Erik and I am a local resident and own a contracting business. I love distressed property rehab and I'm always looking for rehab projects. I am looking for a bright intelligent woman who can make me smile. When not working, I love the outdoors and I am an avid ...
Cuckhold Bull in Chicago Available for Couples... Hello, I'm Ryan and live in Chicago offering my unique service as a Cuckhold bull. I have the physical credentials and am attractive. I stand 6'0, good shape, 9"+ inches, thick and uncut, single, black hair, blue eyes and I am a very easy going guy.  Respect and attentiveness are my watchwords...
🌟 Looking for my Queen of Hearts 🌟 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. 💓 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...
Chivalry Isn’t Dead—But I Might Be After One Good Ride 😏🍑 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...
Dinner, Drinks… and You in the Driver’s Seat? 🍷💋🍑 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. 💫Swap 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. ...
Sweet Guy, Dirty Mind, Zero Pressure 😇Chicago😈  Hi beautiful. At twenty-nine years old I maintain my fitness while being humorous and charming yet slightly  mischievous. When I look at you my eyes show weakness while my laughter makes your stomach ache  😏 View My Dating Profile and Pictures - My approach to romance includes p...
Tall & Peggable 😈💋 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! 😉 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...
Nice Guy? Yep. Push-Over? Only When You’re Behind Me 😉💦 I'm a hopeless romantic at heart, always looking for ways to show my affection and make you feel like the queen that you are. 💖 I believe in chivalry and treating a lady right, so get ready for some old-fashioned charm mixed with a modern twist. Swap pics & contact infoSo if you're ready...

>>>