Chicago Men Seeking Women Sex Ads
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March 4th, 2025
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....
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...
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...
๐ Seeking a Spark With A Hot Lady ;) ๐Chicago 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. ...
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...
you+me=๐Sex Buddies๐ Fit Man Looking For Fun!! (M4F)๐
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- My ProfileI love lots of foreplay, kissing , giving and receiving lots of orgasms. I am very oral i love...
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...
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...
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...March 3rd, 2025
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.
I appreciate femin...
I will always laugh at screaming goats... Chicago Man Seeks FWB
I’m George age 40 here in Chicago and am a bit of a shut-in. I still like going out for drinks and having fun but I find more peace and have more fun just kicking back at home. I love the beach, movies, Disneyland, writing music and poetry, spontaneous trips, and playing...
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...
47, 6' 2 Man Seeking Woman for Dates in Chicago
Hey, Richard here. I just want to say hi to you and hope you might check out my profile and see if you want to date me. I am just a regular guy looking for a regular gal. I've been single too long. It's time to meet someone special to enjoy the fun things in l...
I Need a Chicago MILF Who's Got That Sexpertise! Chicago Man Needs Experienced Woman
Hi all you hot mommas out there in Chicago. I'd love to meet someone to hookup with on a regular basis. FWB style. Young women my age seem to be sort of squirrely and awkward in bed. (just my experience) I picture a MILF as being more focused and educated on matt...
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 am looking for a bright intelligent woman who can make me smile. When not working, I love the outdoors and I am an avid hiker and biker. Send me a message @ErikBachman. ...
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...
Super hot guy waiting for girl of my dreams Black Man for Romantic Woman in Chicago
Dark chocolate man with romantic nature. My name is Dwayne and am 6 feet 3 and well built. I am into sports and I love watching football. Life is good and all but I want to meet a beautiful woman for passion and adventure. Check out my profile @DwayneSeekingR...
Nascar fan looking for lady to have fun with Nascar Fan for Lady in Chicago
If you like watching Nascar or motor racing, hit me up for a date. I am a down to earth guy who likes to chill on weekends and do fun stuff. You must have a good sense of humor because I do like to laugh! There is nothing more sexy than a woman who can make me laugh.
...
Hey ladies, I am Roger, 49 and looking for real love Man Seeking Woman for Dating in Chicago
Hi, my name is Roger. I'm here seeking a woman for dating and friendship - hopefully a lot more! I am 49 with no kids and I own my home. I am local to this area and have lived here for 22 years. I want to meet a kind a funny lady for fun times. Come and say h...
Nigel 56, Chicago new here Male 56 seeks woman in Chicago
Howdy gals, I am Nigel and I am back on the market after a dailed buy out with an ex. lol. That's life. I am lighthearted and friendly and I love to laugh and be made to laugh. If you want to know more, just out my bio page @FunNigel56. ...
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 but gentle and passionate in...
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...
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...
Sailing nut wants to meet lady sailor Male for Female Date Wanted in Chicago
Do you like going out on boats and sailing into the sunset? If you do, give me a call and we can check out my boat together. My name is Lewis and I love the water. Contact Me @CaptainLewis....
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, 26 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...
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?...
Ranch owner and lonely ol' guy Male Ranch Owner Seeking Woman in Chicago
Ok, I ain't that old. Just turned 47 in July. I am a ranch owner with 40 acres and am looking for a gal who is adventurous, outdoorsy, fit and healthy enough to hike, bike and picnic on the trails. Enjoy travel and new experiences? Me too! Hit me up with a ...
Looking for a Chicago MILF Who's Hot as Hell! Yo, all you hot mommas out there in Chicagoland. I'd really love to meet someone to hookup with on the regular - you know, FWB style. I'm Chris, 22 years old, 5'11, 180 pounds and stay in good shape. Young girls in my age bracket seem to be squirrely, unappreciative and awkward in bed. (my experienc...March 2nd, 2025
๐ Handsome Johann Seeking a Spark ๐ 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. ๐Swap pics & contact info I have a passion for exploring the great outdoors, whether it's hiking through the mountains or relaxing by the lake. ๐...
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 ...
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 ...
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...
What songs make you dance? Are you the Stayin Alive type? the Twerker type? Currently looking for a Chicago girl and I love a girl with rythm and groove who knows how to get down. I am not the shy type and some would say extroverted. I love a good time as much as anyone, but also enjoy chillin and bein with my boo. If this is...
Chicago Gamer Seeks Female Gamer for Dating and Fun... Hey let's join forces and level up together. I'm a bit of a nerd and have an outgoing personality. (very social) I'm Denny, 23 years old, 6'0, 200 pounds, blonde hair, blue eyes, love gaming and my cat Sam. About my girl: She should be from Chicago, love gaming or at least be okay with it, be smart,...
Girls on The Goth Side Get My Blood Pumping... Hi I'm Derek, 24 years old, 5'11, 180 pounds, black hair, hazel eyes, as it stands, I'm a bit anti-social. I have broad sexual tastes ranging from the vanilla to BDSM and enjoy fantasy play and trying new things. I need a dark Chicago girl who knows what the Goth scene is all about. Bloodsuckas...
I'm Sexy and I'm Noah!... Single Black Man 4 No Strings in Chicago
Black male, 33, 5'11, 180 pounds, with a good education and positive attitude from Jamaica originally. I have lived here in Chicago for about 10 years and love it. There is always something to do.
I am looking for an original woman. What I mean is some...
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. Want a mature woman for fun, laughter and more. Message @TallEric34m in Chicago....
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 old to keep up ;) I am fit and fast to run with and muscular. Tall and attractive. Want to work out? Travel? Coffee and lets see where i...
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...
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 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...
Daniel 28, Plumber, recently new to area UK Man New to the Chicago Area For Dating
I am from the UK and I am 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. If you would like to say hello send me a message @PipeManLee....
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 ...
New to this place, Andrew, 36. Man Seeks Woman in Chicago
Ok, what do guys say on these things? I want a kind, friendly and fun lady to hang out with and maybe get to know each other a bit. I am tall and somewhat slim build with dark brown wavy hair and blue eyes. Send me a message @TallManChicago...
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...March 1st, 2025
๐ Seeking my Whistler Wonderland ๐Chicago 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. ๐ซSwap 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...
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. If you would like to swap photos and contact info just message me @ShyRomanticBryan and I will respond as soon as...
Tom, 42, wants single minded woman Hello ladies, I am Tom, age 42 in Chicago. I have a good job, decent car and own my house. Life is pretty good and I'm ready to take the next step toward finding love.
I am not looking for someone who is going to give up stuff for me. I want a woman who is already established. If you are that woman...
Breast Obsessed Little Booby Boy... Need Mezmerizing Mammaries in Chicago
Controlled by Cleavage, nipples, areolas, breasts, boobies, tits, hypno, highly suggestible, kinks, fetishes all types. I'm Lenny a 5'9, about 160 pounds, 22 year old single male in Chicago here for magic milk bag fantasies. If you have boobies I'm interested! ...
I wanna be your friend and lover Mature black man in Chicago
Howdy, the name is Samuel and I am a mature gentleman looking for a lady who is smart, funny and outgoing. I am 52, divorced, no kids and I am into riding my bike and fishing on weekends. There is just one thing missing - maybe it's you! How about you message me and...